Aroma Composition Having a Grill-Type Flavour Profile

Information

  • Patent Application
  • 20230363431
  • Publication Number
    20230363431
  • Date Filed
    October 01, 2020
    3 years ago
  • Date Published
    November 16, 2023
    6 months ago
  • CPC
    • A23L27/27
    • A23L27/70
  • International Classifications
    • A23L27/27
    • A23L27/00
Abstract
The present invention relates to a method for preparing an aroma composition having a grill-type flavour profile. The present invention also relates to an aroma composition obtainable using said method and to the use of said aroma composition for providing or enhancing a grill-type flavour and for preparing a foodstuff, food supplement or animal feed. The present invention also relates to food or animal feed products as such which comprise the aroma composition having a grill-type flavour profile. Finally, the present invention relates to an apparatus for preparing said aroma composition.
Description
TECHNICAL FIELD

The present invention relates to a method for preparing an aroma composition having a grill-type flavour profile. The present invention also relates to an aroma composition obtainable by said method and to the use of said aroma composition for providing or enhancing a grill-type flavour and for preparing a foodstuff, food supplement or animal feed. The present invention also relates to foodstuff, food supplement or animal feed products as such which comprise the aroma composition having a grill-type flavour profile. Finally, the present invention relates to an apparatus for preparing said aroma composition.


BACKGROUND ART

Flavours of various types are widely used in the food processing industry. In savoury food products, aroma compositions having a grill-type flavour profile are widely used to impart a grill note or barbeque note flavour to food products for taste purposes.


Grill flavours that mimic or evoke grilled foods are popular in the food industry for inclusion in a wide range of products and are referred to generally as “grill flavour” or “grill-type flavour”. The aroma compositions having a grill-type flavour profile are adapted to mimic the flavours normally created by grilling meat products, which are made of meat protein, meat carbohydrates and animal fat, when typically exposed to temperatures by so-called Maillard reactions. Maillard reactions can produce hundreds of different flavour compounds depending on the chemical constituents in the food, the temperature, the cooking time and the presence of air. These compounds often in turn break down to form yet more new flavour compounds.


Grill-type flavours serve to impart a highly flavoured grill note to prepared foods without requiring actual grilling of the food. Grill flavours also facilitate the inner incorporation of a grill flavour in numerous foods which cannot otherwise be grilled and therefore serve to facilitate grill flavours without burning or carbonisation.


Typical grilled flavours include those used for the preparation of products in which the meat content is reduced or non-existent, for example in sauces, snack foods, meat substitutes, pet foods and the like. Such flavouring compositions can be sprayed onto the foodstuff, or foods can be dipped in a solution of the flavouring, or the flavouring can be applied in a variety of other manners.


Grill-type flavours and methods for producing the same which are obtained by pyrolysis reactions are known from the prior art.


GB 2 363 967 (Colm Declan Menton) describes a process for the preparation of a grill flavour comprising the steps of thermally treating a sunflower oil, to prepare a flavour concentrate, and mixing the flavour concentrate with a sunflower oil.


A known grill flavouring described in EP 0 867 122 A1 (Ensyn Technologies Inc.) is obtained by heating a spray or atomised droplets of a saturated or partially saturated vegetable oil to a temperature of at least 480° C. in an oxygen-starved atmosphere in a fast pyrolysis reactor.


WO 2019/141357 A1 (Symrise AG) discloses a flavouring substance composition having barbecue-type aroma profiles containing (a) at least five linear or branched, saturated aliphatic C5-to-C16 monocarboxylic acids and (b) at least two α,β-unsaturated C10 aldehydes, and a method for their production. In the method for preparing the flavouring, a vegetable or animal oil or fat or mixtures thereof is/are heated to a temperature of 80° C. to 300° C. at a pressure of 0 to 5 bars for 0.1 to 6 seconds, the resulting product is cooled, and the liquid flavour composition obtained is collected.


A common characteristic feature of most of the methods described in the prior art is that pyrolysis or thermolysis is performed either in an inert atmosphere or in the presence of oxygen or air, for example by purging air.


However, the products obtained using such methods generally have a limited aroma profile and a limited level of flavour concentration. In particular, the methods described in the prior art are characterised by the fact that the aroma or flavour composition is prepared at high temperatures, usually at least 350° C., and in the presence of oxygen. Under such drastic conditions, the flavouring oils or fats undergo severe physicochemical changes, such as oxidation of double bonds in fatty acids, or condensation of glycerol with fatty acid decomposition fragments, to name but a few. Thus, the resulting oils and fats have a dark, yellowish-brown to dark brown colour and an aroma and taste resembling that of exhausted deep-frying oils. These aromas and tastes are undesirable, since on the one hand they impart an aroma composition with petrol, tarry or tart notes and on the other hand pose a health hazard. Deep-frying fats have been identified as a source of toxic products such as for example polycyclic aromatic hydrocarbons which may be formed during pyrolysis or the combustion of fats at temperatures above 400° C. For this reason, prior-art methods require additional and complex purification steps to separate or eliminate these undesirable substances.


There is therefore an ongoing need to provide a new production process for an aroma composition having a grill-type aroma profile. Another aim of the present invention is to provide new aroma composition products that mimic or evoke grill-type flavours. There is also a strong need to provide a new aroma composition having an improved grill-type flavour profile. Yet another aim is to ameliorate and/or overcome deficiencies identified in known grill flavourings. Finally, one more aim is to provide products with an improved grill-type flavour profile.


The primary object of the present invention is thus to provide a method for producing an aroma composition which exhibits a novel, intensified, harmonious and well-balanced grill-type flavour profile and which prevents or reduces the formation of undesirable flavour compounds such as undecane, heptane, 2E-octene, 1-nonene, cyclooctene, and nonadecane, etc.


Another object of the present invention is thus to provide an aroma composition which exhibits a novel, intensified, harmonious and well-balanced grill-type flavour profile. In particular, the aroma composition should generate and/or enhance a fatty/oily and/or smoky and/or roasted and/or burnt and/or animalic flavour and at the same time suppress and/or reduce a waxy flavour.


Another aim of the present invention is to provide an apparatus for preparing the aroma composition having a grill-type flavour profile of the present invention.


It has been unexpectedly observed that a method in which vegetable or animal oil or fat or mixtures thereof is/are heated to a temperature of 310° C. to 400° C. at a pressure of 2 to 5 bars in the absence of air or oxygen in the reaction zone, i.e. without air or oxygen supply, and the heated oil stream is subsequently atomised through a nozzle, results in a new and improved aroma composition having a uniquely distinct grill-type flavour profile. The grill-type flavour profile is dominated by grill-type flavour notes characterised by extremely fatty/oily and/or smoky and/or roasted and/or burnt and/or animalic flavour notes and reduced amounts of waxy flavour notes which are distinctive from the flavour notes or characteristics of aroma compositions achieved using the methods according to the prior art, even when using the same feedstock.


According to the present invention, “flavour note” means a compound or compounds that gives rise to a flavour component of the aroma composition according to the present invention.


The distinctive differences in flavour and enhanced, i.e. higher, concentrations of said grill-type flavour notes indicate that a new and different composition results from the present method. Such an unique grill-type flavouring is highly desirable for use in the food-flavouring industry, since a reduced amount of flavouring (additive) can then be used to achieve the desired flavouring. In addition, more pronounced flavouring can be achieved by using equivalent amounts, as compared to other grill-type flavourings.


It has also surprisingly been found that the method according to the present invention prevents or reduces the formation of undesirable flavour compounds such as undecane, heptane, 2E-octene, 1-nonene, cyclooctene, and nonadecane, etc., which are harmful to the sensory properties of the aroma composition, such that the aroma composition manufactured can be directly used without preceding additional purification steps.


SUMMARY OF THE INVENTION

In a first aspect, the present invention relates to a method for preparing an aroma composition having a grill-type flavour profile, comprising or consisting of the following sequence of steps:

    • (a) providing a vegetable or animal oil or fat or a mixture thereof;
    • (b) transferring the product of step (a) to a reactor and heating the product to a temperature in the range of 310° C. to 400° C., in particular 350° C. to 380° C., and a pressure in the range of 2 to 6 bars, to obtain an oil stream;
    • (c) atomising the oil stream, thereby fragmenting the oil stream into a liquid oil phase and an aerosol comprising an aroma composition having a grill-type flavour profile, by an atomising device, preferably by a nozzle;
    • (d) transferring the aerosol containing the aroma to a second line and transferring the liquid oil phase to a third line;
    • (e) discharging the aerosol containing the aroma by collecting the aerosol or absorbing the aerosol on a solid carrier or in a liquid carrier; and
    • (f) optionally returning the liquid oil phase from step (d) to the reactor.


In a second aspect, the present invention relates to an aroma composition having a grill-type flavour profile obtainable using the method according to the present invention.


In a third aspect, the present invention relates to the use of the aroma composition having a grill-type flavour composition for providing or enhancing a fatty/oily and/or smoky and/or roasted and/or burnt and/or animalic flavour and for simultaneously suppressing and/or reducing a waxy flavour in a foodstuff, food supplement or animal feed and/or for preparing a foodstuff, food supplement or animal feed.


In a fourth aspect, the present invention relates to consumer products, food supplements or animal feed to which the aroma composition according to the present invention has been applied.


Finally, the present invention relates to an apparatus for producing an aroma composition having a grill-type flavour profile, with a reactor 1 comprising:

    • (i) a reservoir 2 for the vegetable or animal oil or fat or a mixture thereof, a pump 3, and a heater 4 adapted to heat the vegetable or animal oil or fat or mixture thereof to generate a heated oil stream;
    • (ii) an atomizing device, preferably a nozzle 6, adapted to atomise the heated oil stream in order to fragment the oil stream into a liquid oil phase and an aerosol comprising the aroma composition having a grill-type flavour profile;
    • (iii) optionally an inlet 7 adapted to inject a fluid or gas adjacent to the nozzle exit or to apply a vacuum adjacent to the nozzle exit;
    • (iv) a second line 9 adapted to discharge the aerosol containing the grill-type flavour;
    • (v) a third line 10 adapted to return the liquid oil phase to the reactor;
    • (vi) a container 11 adapted to collect the aerosol; and
    • (vii) a collection vessel 12 adapted to collect the liquid oil phase.





DESCRIPTION OF THE FIGURES


FIG. 1 is a schematic view of the apparatus according to the present invention.



FIGS. 2a and 2b are each a schematic cross-section of a preferred embodiment of a nozzle of the apparatus according to the present invention, describing single component type nozzles without additive gases and the like—an straight-forward orifice.



FIG. 3 is a schematic cross-section of another preferred embodiment of a nozzle of the apparatus according to the present invention, using an additive, usually an inert atomiser gas.



FIG. 4 is a schematic cross-section of another preferred embodiment of a nozzle of the apparatus according to the present invention, which is an internal mix nozzle, where the atomiser gas is supplied in the interior of the nozzle.



FIG. 5 is a schematic cross-section of another preferred embodiment of a nozzle of the apparatus according to the present invention, which describes effervescent atomisation, which is a special type of atomisation.



FIG. 6 is a schematic cross-section of a preferred embodiment of a Venturi nozzle of the apparatus according to the present invention.



FIG. 7 is a schematic cross-section of another preferred embodiment of a nozzle of the apparatus according to the present invention.



FIG. 8 is a spider diagram showing the flavour profile of the grill-type flavour according to the present invention in comparison with the flavour profile of a grill-type flavour according to the prior art. The comparison is shown for the flavour profile of the grill-type flavour obtained according to WO 2019/141357 A1 and a flavour profile obtained according to the present invention after 4 intakes.





The invention is specified in the appended claims. The invention itself, and its preferred variants, other objects and advantages, are however also apparent from the following detailed description in conjunction with the accompanying examples and figures.


DETAILED DESCRIPTION OF THE INVENTION

The present invention will now be described by referring to the accompanying figures. In the following description, corresponding elements as shown in each figure of the drawings are given the same reference sign.


In a first aspect, the present invention relates to a method for preparing an aroma composition having a grill-type flavour profile, comprising or consisting of the following sequence of steps:

    • (a) providing a vegetable or animal oil or fat or a mixture thereof;
    • (b) transferring the product of step (a) to a reactor and heating the product to a temperature in the range of 310° C. to 400° C., in particular 350° C. to 380° C., and a pressure in the range of 2 to 6 bars, to obtain an oil stream;
    • (c) atomising the oil stream, thereby fragmenting the oil stream into a liquid oil phase and an aerosol comprising an aroma composition having a grill-type flavour profile, by an atomizing device, preferably by a nozzle;
    • (d) transferring the aerosol containing the aroma to a second line and transferring the liquid oil phase to a third line;
    • (e) discharging the aerosol containing the aroma by collecting the aerosol or absorbing the aerosol on a solid carrier or in a liquid carrier; and
    • (f) optionally returning the liquid oil phase from step (d) to the reactor.



FIG. 1 depicts a schematic view of the apparatus according to the present invention. The apparatus comprises a reactor 1 of the type that can be utilised to make an aroma composition having a grill-type flavour profile. The reactor 1 comprises a reservoir 2 in which a vegetable or animal oil or a fat or a mixture thereof is provided, a pump 3 and a heater 4. The reactor 1 also comprises a first line 5, an atomizing device which is preferably a nozzle 6, a second line 9, a third line 10, a container 11 for the aroma discharged and finally a collection vessel 12 for the liquid oil phase.


One of the features of the process according to the invention is that the aroma composition can be produced in a continuous reactor, which enables the flavour composition to be produced continuously. The composition can, however, alternatively be produced in batches.


In a first step (a) of the method according to the present invention, a vegetable or animal oil or vegetable or animal fat or a mixture thereof is provided as a starting product for producing the aroma composition according to the present invention. For the purposes of the present application, this means that a single vegetable oil or a single animal oil or a single vegetable fat or a single animal fat or a mixture of two or more of a vegetable oil, animal oil, vegetable fat or animal fat may be used.


Vegetable oils and fats are biological mixtures of plant origin consisting of ester mixtures derived from glycerol with chain of fatty acids. Both, the physical and the chemical characteristics of oils and fats are greatly influenced by the kind and proportion of the fatty acids on the triacylglycerol. Fatty acids can be classified in classes of saturated, mono-unsaturated (MUFA) and poly-unsaturated (PUFA) fatty acids. The predominant fatty acids present in vegetable oils and fats are saturated and unsaturated compounds with straight aliphatic chains. An even number of carbon atoms, from 16 to 18 with a single carboxyl group, is the most common. A number of minor fatty acids may be present in same vegetable sources, including a small amount of branched chain, cyclic and odd number straight chain acids. An important feature common to most plant origin oils and fats is the high percentage of unsaturated fatty acids in the triacylglycerols. In general, the higher degree of unsaturation of fatty acids in vegetable oils is, the more susceptible they are to oxidative deterioration. Therefore, it is essential to know the composition of fatty acids of an oil or fat, to identify their characteristics and to know the physical and the chemical properties. The fatty acid composition of safflower and sunflower oil contains a healthy mixture of all the types of saturated and unsaturated fatty acid. The value of P/S index which is associated to the impact in the human health is also high for safflower and sunflower oil.


The appropriate vegetable oils that are utilized in the method according to the present invention are those having a high stability, namely, those vegetable oils, that are saturated or are partially unsaturated.


Examples of appropriate vegetable oils used in the method according to the present invention include unsaturated, saturated or partially saturated palm oil, palm kernel oil, soybean oil, sunflower oil, peanut oil, olive oil, rapeseed oil, grapeseed oil, canola oil, corn oil, coconut oil, sesame oil, poppyseed oil, safflower oil, pumpkin seed oil, rice bran oil, almond oil, pecan oil, macadamia oil, cottonseed oil, linseed oil, or mixtures of two or more of these vegetable oils. Alternative feedstocks include animal fats such as pig fat (lard), beef fat (tallow), mutton fat (tallow), bacon dripping, chicken fat, turkey fat, butter or mixtures of two or more of these animal fats.


According to Vesna Kostik et al., Fatty acid composition of edible oils and fats, HEDJ Journal of Hygienic Engineering and Design, original scientific paper, UDC 664.3:577.115.3, the content of the following saturated and unsaturated fatty acids caproic acid (C6:0), caprylic acid (C8:0), capric acid (C10:0), lauric acid (C12:0), myristic acid (C14:0), palmitic acid (C16:0), stearic acid (C18:0), arachidic acid (C20:0), behenic acid (C22:0), lignoceric acid (C24:0) oleic acid (C18:1), linoleic acid (C18:2) and linolenic acid (C18:3) of the following tested oil samples is as shown in Table 1 and Table 2. respectively:









TABLE 1







Saturated fatty acid (SFA) composition of different vegetable oils and fats (% w/w)









Mean ± SD















Type of
C6:0
C8:8
C10:0
C12:0
C14:0
C16:0
C18:0
C20:0


oil/fat
(%)
(%)
(%)
(%)
(%)
(%)
(%)
(%)





Coconut
0.04 ± 0.2
7 ± 2.0
8 ± 2.0
48 ± 4
16 ± 3 
9.2 ± 1.5

2 ± 1.0

0.25 ± 0.2 


Corn

4 ± 0.8
7 ± 1.2

0.6 ± 0.4
10 ± 2 
3.5 ± 1.5



Cottonseed




0.4 ± 0.2
 20 ± 2.5

2 ± 0.6




Linseed





5.5 ± 1.5
3.5 ± 1.2
0.65 ± 0.3 


Palm

4 ± 1
5 ± 2
41 ± 5
16 ± 2 

8 ± 0.0


2 ± 0.8




kernel


Olive




0.65 ± 0.2 
11.5 ± 4  

2 ± 0.5

0.22 ± 0.12


Soybean




0.5 ± 0.2
9 ± 2
4 ± 1



Sunflower





3.7 ± 1.5

2 ± 0.8

2.3 ± 1.2


Peanut





7.5 ± 1.5
4.5 ± 1.8

3 ± 1.2



Safflower




0.5 ± 0.2
4.0 ± 1.8
2.5 ± 0.1
0.2 ± 0.1


Canola





5.2 ± 0.6
4.4 ± 1.4



Type 1


Canola





10.5 ± 2.5 
6.9 ± 1.6



Type 2
















TABLE 2







Unsaturated fatty acid (UFA) composition of


different vegetable oils and fats (% w/w)










Mean ± SD











Type of oil/fat
C18:1 (%)
C18:2 (%)
C18:3 (%)





Coconut
 8.8 ± 0.85
 0.5 ± 0.2



Corn
26.8 ± 1.2

48 ± 4.5




Cottonseed
35.4 ± 2.4

42 ± 4.8




Linseed
22.1 ± 1.5
20.5 ± 1.5
47.5 ± 5.6


Palm kernel
22.5 ± 2.2
 1.25 ± 0.55



Olive
78.4 ± 4.3
 7.0 ± 3.3



Soybean
28.5 ± 1.2
49.5 ± 6.5
  8 ± 3.4


Sunflower
31.5 ± 4.5
59.5 ± 7.5



Peanut
58.5 ± 5.8

20 ± 2.7




Safflower
16.6 ± 4.5
76 ± 3



Canola Type 1
 59.5 ± 1.907
18.8 ± 3.5
11.9 ± 1.1


Canola Type 2
23.2 ± 2.9
15.2 ± 3.6
  44 ± 2.02









The content of total saturated fatty acid (SFA), monounsaturated fatty acid (MFA), polyunsaturated fatty acids (PUFA) and the relationship between saturated and poly-unsaturated fatty acid content is expressed as P/S index. The P/S index is an important parameter for determination of nutritional value of certain oil. Oils and fats with a higher P/S index value that 1 are considered to have nutritional value. The highest P/S index value was found for safflower oil.









TABLE 3







The content of saturated fatty acids (SFA),


monounsaturated fatty acids (MUFA), polyunsaturated


fatty acids (PUFA (% w/w) and the values of P/S


indexes (poly-unsaturated/saturated index)


of different types of vegetable oils









Type of
Mean ± SD
P/S











oil/fat
SFA (%)
MUFA (%)
PUFA (%)
index














Coconut
 90.5 ± 2.95
 8.8 ± 0.85
 0.5 ± 0.02
0.005


Corn
 25.1 ± 1.8
26.8 ± 1.2
  48 ± 4.5
1.91


Cottonseed
 22.4 ± 1.22
35.4 ± 2.4
  42 ± 4.8
1.87


Linseed
 9.65 ± 1.05
22.1 ± 1.5
  68 ± 2.9
7.05


Palm
   76 ± 1.95
22.5 ± 2.2
1.25 ± 0.55
0.016


kernel






Olive
14.35 ± 1.9
78.4 ± 4.3
 7.0 ± 0.33
0.49


Soybean
 13.5 ± 0.93
28.5 ± 1.2
57.5 ± 2.2
4.26


Sunflower
 8.8 ± 0.8
31.5 ± 4.5
59.5 ± 7.5
6.76


Peanut
 19.2 ± 0.37
58.5 ± 5.8
  20 ± 2.7
1.04


Safflower
 7.2 ± 0.3
16.6 ± 4.5
  76 ± 3
10.55


Canola
 9.6 ± 0.56
59.5 ± 1.907
30.7 ± 1.7
3.2


Type 1






Canola
 17.4 ± 0.67
23.2 ± 2.9
59.2 ± 1.1
3.4


Type 2













Sunflower oil seed oil showed high PUFA content (59.5%±7.5) with the predominant presence of linoleic acid (C18:2). The highest content of total unsaturated fatty acids was found for safflower (92.6%±1.0) and sunflower oil (91%±2.12).


The above fatty acid contents and results are in line with the data obtained from the literature (see Zambiazi R. C. et al., Fatty acid composition of vegetable oils and fats (2007), B.CEPPA, Curitiba (25(1), pages 111-120 and Daniewski M., et al., Fatty acids content in selected edible oils (2003), Roczniki-Pastwowego-Zaklad-Higieny 54(3), pages 263-267). However, the data can vary due to the plant variety, season, origin etc. where the plant was cultivated.


It has been found that flavouring compositions with particularly advantageous sensory grill-type flavour properties are produced if the oil or fat starting product provided in step (a) comprises the following fatty acid spectrum:

    • 3 to 14.0% by weight of palmitic acid (C16:0);
    • 0.8 to 12.5% by weight of stearic acid (C18:0);
    • 18.0 to 87.0% by weight of oleic acid (C18:1);
    • 2.0 to 30.0% by weight of linoleic acid (C18:2);
    • 0.2 to 2.2% by weight of arachidic acid (C20:0); and
    • 0.6 to 4.0% by weight of behenic acid (C22:0);


      and optionally one or more or all of the fatty acids from the group consisting of:
    • 0 to 6.0% by weight of butyric acid (C4:0);
    • 0 to 2.9% by weight of caproic acid (C6:0);
    • 0 to 65.0% by weight of caprylic acid 8:0);
    • 0 to 45.0% by weight of capric acid C10:0);
    • 0 to 4.5% by weight of lauric acid (C12:0);
    • 0 to 11.5% by weight of myristic acid (C14:0);
    • 0 to 74.0% by weight of linolenic acid C18:3);
    • 0 to 4.3% by weight of eicosenoic acid (C20:1);
    • 0 to 2.5% by weight of cetoleic acid (C22:1);
    • 0 to 2.9% by weight of myristoleic acid (C14:1); and
    • 0 to 3.9% by weight of palmitoleic acid (C16:1);


      based on the total fatty acid content, providing that the quantities indicated add up to 100% by weight.


In a preferred variant, the oil or fat starting product provided in step (a) comprises the following fatty acid spectrum:

    • 4.0 to 8.0% by weight of palmitic acid (C16:0);
    • 3.0 to 11.0% by weight of stearic acid (C18:0);
    • 72.0 to 85.0% by weight of oleic acid (C18:1);
    • 4.0 to 17.0% by weight of linoleic acid (C18:2);
    • 1.5 to 2.0% by weight of arachidic acid (C20:0); and
    • 2.5 to 3.5% by weight of behenic acid (C22:0);


      based on the total fatty acid content, providing that the quantities indicated add up to 100% by weight.


From the above specified vegetable oils vegetable oils with a particular high oleic and/or linoleic acid content are preferred as starting product in the method according to the present invention. Particularly preferred from the above specified vegetable oils are sunflower oil, rapeseed oil, corn oil, linseed oil and safflower oil, due to their oleic acid (18:1) and linoleic acid (18:2) content. Especially preferred as starting product is sunflower oil with a high oleic acid content. One known sunflower oil high in oleic acid has about 82% oleic acid.


The oil or fat starting material or feedstock is provided in the reservoir 2.


In the following step (b) of the method according to the present invention, the feed stream of the oil or fat starting product is introduced via the pump 3 along the first line 5 towards a heater 4 provided as a heating or reaction zone. The oil or fat starting product or feedstock can be fed to the heating or reaction zone continuously or in batches.


In the heating or reaction zone, thorough and rapid mixing occurs, and conductive heat is transferred from the heater to the oil or fat starting product or feedstock.


In the heating or reaction zone, the oil or fat starting product or feedstock is subjected to a heat treatment in which it is heated to a temperature in the range of 310° C. to 400° C. In a preferred variant of the method according to the present invention, the oil or fat starting product is heated to a temperature in the range of 350° C. to 380° C. and particularly preferably 360° C. to 370° C. Objectionable flavours develop at contact temperatures above 400° C., while at contact temperatures below 310° C., the desired flavour profile and desired concentration of flavour compound do not develop. The best contact temperature is above 360° C., but below 370° C.


The step (b) of heating the oil or fat starting product is performed at a pressure in the range of 2 to 6 bars and particularly preferably 3 to 4 bars. This improves the flow properties and acts to control the aroma.


The dwelling time of the oil or fat starting product in the heating zone is 10 to 30 seconds, preferably 12 to 28 seconds and particularly preferably 15 to 25 seconds. The dwelling time is defined as the period from the time when the feedstock comes into contact with the heater to the time when it exits the heating zone.


Aroma compositions with particularly favourable sensory properties result when the oil or fat starting product is heated in step (b) to a temperature in the range of 360° C. to 370° C. at a pressure in the range of 3 to 4 bars for 10 to 30 seconds.


It has been found that the temperature in step (b) is crucial to obtaining a harmonious and balanced grill-type flavour profile with a high impact, i.e. flavour intensity, in particular a flavour profile in which the fatty/oily and/or smoky and/or roasted and/or burnt and/or animalic flavour notes are accentuated and the waxy flavour notes are suppressed or reduced.


Using the process parameters specified above, compounds which contribute to fatty/oily and/or smoky and/or roasted and/or burnt and/or animalic flavour notes are advantageously generated in the oil or fat starting material during the heating step (b) of the method according to the present invention, namely compounds such as capric acid, oleic acid, 2E-decenal, 2E-undecenal, 2E,4E-decadienal, and 1-dodecene, while the formation of undecane, heptane, 2E-octene, 1-nonene, cyclooctene, and nonadecane, etc., which are harmful to the sensory properties, is suppressed or greatly reduced. The latter compounds may contribute to an undesired waxy flavour note.


The method according to the present invention, in particular the heating step (b), is performed in a reducing atmosphere which is either at a reduced oxygen level or substantially free of oxygen or air. No air or oxygen is supplied in the pyrolysis or thermolysis step (b). The only oxygen present is that which is necessary for purging the pressure tap, or any residual amounts of oxygen in the feedstock or that enter the system due to system limitations or leaks.


In a preferred variant, the heating step (b), i.e. pyrolysis or thermolysis is performed in the absence of oxygen or air in the reaction zone. Preferably, the process is performed without purging air.


It is preferred that the generated oil stream in the first line 5 exiting the reservoir 2 and passing the heating zone 4 is in laminar flow. Avoiding turbulences decreases friction and provides a consistent source for the atomizing device and thus predictable aroma concentrations.


Due to the absence or near-absence of oxygen in the heating or reaction zone, the process of the present invention is an endothermic pyrolysis or thermolysis and is a non-combustion process. This leads to a completely different series of chemical reactions, resulting in an aroma composition that differs from those obtained using the methods according to the prior art, as exemplified in Table 4 below.


In the heating or reaction zone 4 of the reactor 1, the oil or fat starting product or feedstock is preferably raised to the desired approach temperature by means of electrical resistance heating, indirect combustion, direct combustion or a combination of these.


In a preferred variant, the oil or fat starting product or feedstock is subjected to the high-temperature treatment in the heating zone in the form of a film (i.e. a thin layer, sheet or droplets) which maximises the exposure of the oil or fat starting product to the required temperature in order to obtain an aroma composition having the desired grill-type flavour profile. A preferred method of subjecting the oil or fat starting product to this high-temperature treatment is to employ a continuous-feed, thin-film and/or high-temperature cooking process. Alternatively, rods which are heated to within the required temperature range can be inserted into a bath of oil or fat in order to perform the high-temperature treatment.


In a preferred variant of the method according to the present invention, the oil or fat starting product or feedstock is heated by electromagnetic induction.


The process of induction heating has been used in industry for a long time and is well known to those skilled in the art. The most common applications are for melting, hardening, sintering and/or heat-treating alloys. Processes such as bonding, shrinking or joining components are however also well-known applications of this heating technology.


The principle of induction heating and the design of induction heating devices are described in the technical literature, for example in: Elektrotechnologie, edited by H Conrad, R Krampitz, VEB Verlag Technik Berlin, 1983, pages 58-114; Induktionserwärmung, G Benkowski, Berlin Verlag Technik, 1990; Practical Induction Heat Treating, R E Haimbaugh, ASM International, December 2001; Handbook of Induction Heating, V Rudnev, D Loveless, R Cook, M Black, Marcel Dekker Inc, New York and Basel, 2003.


Document DE 10 2005 051 637 describes a reactor system with a micro-structured reactor and a method for performing a chemical reaction in such a reactor. The reactor itself is heated by electromagnetic induction. The heat is transferred into the reaction medium via the heated reactor walls.


It is known from the journal article Inductive heating in organic synthesis by using functionalised magnetic nanoparticles in microreactors by S Ceylan, C Friese, Ch Lam mel, K Mazac and A Kirschning, in: Angewandte Chemie [Applied Chemistry] 2008 (129), pages 9083-9086, Angewandte Chemie international edition 2008 (47), pages 8950-8953, that chemical reactions can be performed by heating a medium with the aid of electromagnetic induction.


The principle of induction heating and the design of induction heating devices are for example described in the above-mentioned technical literature, such that the person skilled in the art who consults the available technical literature and applies their general knowledge in the art will be quite capable of installing the device for performing the method, without unreasonable effort and without performing an inventive step, and determining the optimum parameters for induction heating (for example, choosing the frequency of the reactor and inductor) in order to perform the process within the entire range under consideration.


In a preferred variant of the present application, the walls of the reactor itself are heated. The reactor therefore consists of an electrically conductive and/or magnetisable material which heats up under the influence of an alternating electromagnetic field. Preferred reactor materials include electrically conductive ceramics, such as SiC (silicon carbide), or refractory metals preferably selected from the group comprising titanium, tantalum, niobium, molybdenum, tungsten, alloys of these metals as well as nickel-based, cobalt-based and chromium-based alloys and high-temperature steels.


Heat transfer elements such as heating coils or heat exchanger tubes or plates can however also be incorporated into the reactor within the scope of the present invention.


It goes without saying that the nature of the heating medium and the design of the inductor must be adapted to each other such that the desired heating of the reaction mixture can be achieved. Critical parameters for this are on the one hand the power of the inductor expressed in watts and on the other hand the frequency of the alternating field generated by the inductor. In principle, the greater the mass of the heating medium to be inductively heated, the higher the power selected needs to be. In practice, the power which can be achieved is limited in particular by the capacity for cooling the generator which is required in order to supply the inductor.


Inductors which generate an alternating field with a frequency in the range of about 1 to about 100 kHz, preferably about 10 to about 80 kHz and particularly preferred about 10 to about 30 kHz, are particularly suitable. Such inductors and the associated generators are commercially available, for example from IFF GmbH of Ismaning, Germany.


Induction heating is thus preferably performed with an alternating field in the medium frequency range. As compared to excitation at higher frequencies, for example those in the high-frequency range (above 0.5 MHz and in particular above 1 MHz), this has the advantage that the energy input into the heating medium can be better controlled. Within the context of the present invention, it is therefore preferable to use inductors which generate an alternating field in the aforementioned medium frequency range. This allows economical and easy control of the reaction.


In order to prevent the thermal energy transferred to the reactor from being lost to convection or heat conduction through the air, the reactor can be arranged in a housing which can be evacuated. This applies to all types of reactor which can be used in the process of the present invention. An evacuated housing offers the additional advantage that any leakage in the reactor can be easily detected analytically or can be quickly detected due to a pressure increase inside the housing. It also prevents toxic chemical compounds, escaping through a leak, from emerging directly into the atmosphere.


The reactor housing can for example be an elongated glass, quartz glass or ceramic housing. This housing can be provided with a heat-reflecting cover on the inside to minimise losses due to heat radiation. This coating preferably does not consist of an electrically conductive material, in order to prevent it from heating up while induction heating is performed using the energy field. Additionally, or alternatively, a heat-reflecting internal coating can also be provided in the evacuated zone and can be made of the same materials as the heat-reflecting coating of the reactor housing. The housing can also be self-cooled, for example using water or air.


Once the oil or fat starting material has been heated under the aforementioned conditions, a heated and pressurised oil stream containing pyrolysis products is obtained and leaves the heating or reaction zone.


In the process step (c), the heated and pressurised oil stream containing pyrolysis or thermolysis products is then piped through the first line 5 to an atomizing device, which can be a nozzle 6, for atomising or vaporising the heated oil stream and fragmenting the oil stream into a liquid oil phase and an aerosol comprising an aroma composition having a grill-type flavour profile.


It is preferred that the generated oil stream piped through the first line 5 and exiting the heating zone 4 is in laminar flow. Avoiding turbulences decreases friction and provides a consistent source for the atomizing device and thus predictable aroma concentrations.


The term “atomisation” refers to separating substances into fine particles; it is a process of breaking bulk liquids into small droplets, thus producing an aerosol. An aerosol is defined as a suspension system of solid or liquid particles in a gas. An aerosol includes both the particles and the suspending gas, which is usually air. The atomizing device is preferably a nozzle.


A nozzle is a mechanical device such as a pipe or tube exhibiting a variable cross-sectional area wherein the change in cross-sectional area affects an exchange of pressure and ejection velocity.


Thus, in a nozzle, the velocity of the fluid increases rapidly at the expense of its pressure energy. When a nozzle is placed on a pipe, the flow nozzle causes a drop in pressure which varies with the flow rate. This can be used to atomize a fluid, such as with a spray nozzle.


Typically, the diameter of the nozzle tube gradually decreases from a starting point to the end of the nozzle. Other designs are possible, but a release of fluids or gases from a confined tube into a free airspace is conventional. At the starting point, where the cross-sectional area is high, the pressure is high and the velocity is low, but towards the end of the nozzle, when the cross-sectional area decreases, the pressure decrease and the velocity increases. After leaving the nozzle, the ejected driving fluid or motive (steam, pressurised liquid or air) has a considerably higher velocity. When the heated and pressurized fluid is passed through the body of the nozzle into a free airspace, a partial drop in pressure occurs. Once the vapour pressure is reached, evaporation occurs. Due to the difference in pressure which exists, the bubbles burst outside the nozzle, fuelling the disintegration of the heated and pressurised oil stream. This results in two phases: a vapour phase (aerosol) enriched in the more volatile components, and a liquid oil phase, enriched in the less volatile components. The vapour phase (aerosol) and the liquid oil phase are separated by gravimetry. The vapour is taken off overhead, while the liquid drains to the bottom, where it is withdrawn.


Spray nozzles can be categorized based on the energy input used to cause atomization, which is the breakup of the fluid into drops. Spray nozzles can have one or more outlets; a multiple outlet nozzle is known as a compound nozzle. Single-fluid or hydraulic spray nozzles utilize the kinetic energy of the liquid to break it up into droplets.


When a fast liquid stream is injected into the atmosphere through a nozzle, it causes a pressure difference between the liquid in the pipe and the lower pressure in the gas stream, in accordance with Bernoulli's principle. The difference between the reduced pressure outside the nozzle and the higher pressure inside the nozzle pushes the liquid from the first line 5 through the nozzle 6 and into the moving stream of air, where it is broken up into small droplets (though not individual atoms, as the term may suggest) or atomised. Presently, the atomizer used can be a simple plain orifice nozzle. Such a plain orifice nozzle is shown in FIGS. 2a and 2b.


Different types of atomiser or nozzle can be used to generate aerosols. Atomisers or nozzles are classified as mechanical or pneumatic atomisers or nozzles depending on their energy supply. Rotary or ultrasonic sprayers are classified into the first group. The disintegration of a liquid by pneumatic atomisers or nozzles is caused by aerodynamic interactions between the gas and liquid phase. Jet nozzles, turbulence nozzles and lamellar nozzles are distinguished according to the primary liquid structure at the back of the atomiser or nozzle. The aerodynamic interaction characteristics of two-component nozzles are enhanced by using an additional gas.


Nozzles which are based on atomising a fluid without using an additive are called single-component nozzles. They are characterised by their simple construction. Pressure energy is converted into kinetic energy. Turbulence nozzles are similarly the geometrically simplest atomisers. The formation of turbulence in the nozzle is specifically stimulated by guiding the flow of the liquid in the nozzle. The difference in velocity between the environment and the liquid jet leaving the nozzle causes interactions between the phases. Inhomogeneities in the jet, caused by the turbulence generated in the nozzles, are amplified and result in the liquid disintegrating. Hole-type nozzles or elbow nozzles are examples of the aforesaid nozzles (see FIGS. 2a and 2b). Single-component and turbulent nozzles can afford different aroma profiles due to higher mixing rates in the stream.


Lamellar nozzles are used to generate finer sprays using moderate pressures. Unlike turbulence nozzles, in which the liquid is shaped into a jet, lamellar nozzles are distinguished by the fact that the nozzle shape used forms the liquid into a lamella, which ultimately disintegrates into droplets. Examples include flat-jet nozzles and hollow-cone nozzles. These are also preferred presently to afford a higher distribution of aerosol vs. liquid oil phase that is recycled.


In the airless atomisation process, high pressure forces fluid through a small nozzle. The fluid emerges as a solid stream or sheet at high speed. The friction between the fluid and the air disrupts the stream, breaking it up initially into fragments and ultimately into droplets. The energy source for this form of atomisation is fluid pressure which is converted into momentum as the fluid leaves the nozzle. Three factors that affect an airless spray include the diameter of the atomiser orifice, the atmosphere and the relative velocity between the fluid and the air. With respect to the orifice diameter, the general rule is that the larger the diameter or size of the atomiser orifice, the larger the average droplet size in the spray. The atmosphere provides resistance and tends to break up the stream of fluid. This resistance tends to partially overcome the fluid's properties of surface tension, viscosity and density. The air temperature can also affect atomisation. The relative velocity between the fluid and the air also affects droplet size. The fluid's velocity is created by pressure in the nozzle. As the fluid pressure increases, the velocity increases and the average droplet size decreases; conversely, as the fluid pressure decreases, the velocity is lower and the average droplet size is greater. Airless nozzles are possible to use in the present invention.


Another preferred way of influencing the size distribution of droplets is to use an additive, usually an inert atomiser gas. The relative velocity between the liquid phase and gas phase, which is increased by the additive gas component, increases the momentum exchange and leads to more intense turbulence in the liquid jet to be atomised. The geometry of the nozzles is dependent on the type of gas supply. If the gas and the liquid to be atomised come into contact outside the nozzle, this is called external mix atomisation (see FIGS. 3a and 3b). In the simplest case, the liquid is fed centrally into a jet of gas. The liquid and the gas flow out of the nozzle at different velocities. Momentum exchange between the more slowly flowing liquid and the more quickly flowing gas accelerates the liquid. These types of nozzles with additive gases can be used to atomize the oil stream.


In the case of internal mix nozzles, the atomiser gas is supplied in the interior of the nozzle (see FIG. 4). The introduced gas component generates turbulence in the multi-phase flow, which promotes instability and thus the disintegration of the liquid. These types are preferred to generate fine aerosol distributions and greater output of the reactor.


In air-spray atomisation, fluid emerging from a nozzle at low speed is surrounded by a high-speed stream of air. Friction between the liquid and the air accelerates and disrupts the fluid stream, causing atomisation. The energy source for air atomisation is the air pressure. The operator can regulate the flow rate of fluid independently of the energy source. FIG. 4 shows a stream of fluid passing through an orifice; as it emerges, a high-speed stream of air surrounds the fluid stream.


Effervescent atomisation is a special type of atomisation in which gas is guided internally. The essential structure of the nozzle is shown in FIG. 5. The gas phase is added in a mixing chamber. The resultant two-phase flow exists as a bubbly flow in the mixing chamber. A slug flow or annular flow is generated at the nozzle exit. Outside the nozzle, the thin annular lamella of liquid is disintegrated into droplets by the gas phase flowing at high speed at the centre of the nozzle. Thus, this nozzle arrangement is also preferred for greater mixing.


Superheated or flash atomisation is a special way of generating aerosols. Simple pressure nozzle geometries are used. A liquid stream containing several components is partially vaporised in a flash drum at a certain pressure and temperature. This results in two phases: a vapour phase (aerosol) enriched in the more volatile components, and a liquid phase, enriched in the less volatile components. The fluid is heated and pressurized and is then passed through a nozzle into the flash drum. A partial drop in pressure occurs as the fluid flows through the body of the nozzle. Once the vapour pressure is reached, evaporation occurs. Due to the difference in pressure which exists, the bubbles burst outside the nozzle, fuelling the disintegration of the liquid stream. The vapour is taken off overhead, while the liquid drains to the bottom of the drum, where it is withdrawn. An additional gas additive is not needed for disintegrating the liquid, since the gas and/or vapour phase comes directly from the atomiser liquid. The high temperatures of the atomiser liquid reduce the viscosity and surface tension of the liquid. This promotes the generation of small droplets. As superheating increases, a finer spray is generated. Again, this is a preferred method as finer droplets are generated by such atomisation.


In a more preferred variant of the method according to the present invention, the heated oil stream is atomised or vaporised and thereby fragmented into a liquid oil phase and an aerosol comprising an aroma composition having a grill-type flavour profile using a Venturi nozzle (see FIG. 6).


A Venturi nozzle consists of three parts: a nozzle, a body and a diffuser or a constriction point. The Venturi nozzle is a mechanical device such as a pipe or tube exhibiting a variable cross-sectional area wherein the change in cross-sectional area effects an exchange of pressure and temperature for ejection velocity. Typically, the diameter of the nozzle tube gradually decreases from a starting point to a constriction point of the nozzle after which the diameter increases again rapidly towards the end of the nozzle (see FIG. 6). That construction builds backpressure up-stream and effects a negative pressure down-stream of the constriction. As the volume of fluid is forced through the reduced diameter fluid dynamic laws determine that the increased flow velocity be accompanied by a pressure drop. Thus, the ejection speeds are high which coincides with a fast drop in pressure and temperature. This process leads to a particularisation of the ejected fluid.


Of the above types of nozzle, flash atomisation or Venturi nozzles are particularly preferred used in the method according to the present invention.


The properties of the aerosol generated depend significantly on the nozzle geometry and the fluid properties of the atomiser liquid. These factors influence both the flow through the nozzle and the behaviour of the clusters of droplets after they exit the nozzle. In the capillary, the hydrodynamics are determined by changes in cross-section (flow constriction, loss of pressure), unevenness (friction) and the properties of the atomiser liquid. Additionally, a variety of factors affect droplet size and the ease with which a stream of liquid atomises after emerging from an orifice. These factors including the fluid properties of surface tension, viscosity and density.


The diameter of the nozzle tube in the method according to the present invention is preferably 1.2 to 3.0 mm, more preferably 1.5 to 2.8 mm and most preferably 2.0 to 2.3 mm.


Through atomisation or vaporisation by a nozzle, the heated and pressurised oil stream is fragmented into two inhomogeneous phases: a vapour phase with finer droplets (aerosol) enriched in the more volatile components constituting the aroma composition having a grill-type flavour profile, and a liquid phase, enriched in the less volatile components. In the fragmented bigger droplets of the liquid oil phase however, less volatile compounds are contained. The aerosol with the finer droplets and the phase with the bigger oil droplets are separated by gravimetry. The vapour is taken off overhead, while the liquid drains to the bottom of the drum, where it is withdrawn.


In order to improve the atomisation of the oil stream and thereby the fragmentation of the oil stream into a liquid oil phase and an aerosol comprising the aroma composition having a grill-type flavour profile, and/or to increase the velocity of the aerosol stream and, thus, to accelerate the transport of the aerosol stream to the container 11, the body of the nozzle, preferably the Venturi nozzle, is preferably provided with an inlet 7, as it is schematically depicted in FIG. 7.


Via this inlet, gas or fluid is injected or sucked via a suction chamber adjacent to the nozzle exit, creating suction flow. The driving fluid or motive (steam, pressurised liquid or air) passes through the nozzle of the ejector. By increasing the velocity of the fluid as it passes through the nozzle, a low-pressure region or suction flow at the exit of the nozzle is created within the ejector. This low pressure region entrains and compresses the secondary gas or fluid, i. e. the suction gas or fluid stream. The motive stream (steam, pressurised liquid or air) and the suctioned gas or fluid stream are mixed. As the combined driving fluid and secondary gas or fluid streams pass through an ejector's diffuser section, the velocity decreases and the pressure is regained, so that the fluid is discharged from the ejector with a backpressure.


In a preferred variant of the method, atomisation is performed using as injection gas an inert gas, such as nitrogen, or air.


Alternatively, a vacuum is applied to the nozzle or adjacent to the nozzle exit, creating a suction flow, via this inlet 7 and controlled by a vacuum control unit 8. Applying a vacuum, preferably at a pressure of 200 to 800 mbar, more preferably at a pressure of 300 to 600 mbar, most preferably at a pressure of 450 to 500 mbar, increases the velocity of the motive stream (steam, pressurised liquid or air) through a drop in pressure.


Both of the described configurations of the nozzle promote atomisation of the (preferably laminar) oil stream on the one hand and improve the transport or evacuation of aerosol charged with the aroma composition on the other hand.


Therefore, in preferred variants of the method according to the present invention the atomizing device is characterised by injecting a fluid or gas adjacent to the nozzle exit or applying a vacuum at a pressure of 200 to 800 mbar adjacent to the nozzle exit.


Driving the heated and pressurised (preferably laminar) oil stream containing pyrolysis products, produced in method step (b), through any of the nozzles described above, atomises or vaporises it by virtue of the nozzle and thus fragments it into a liquid oil phase and an aerosol comprising the aroma composition having a grill-type flavour profile.


Due to the ejection of the heated and pressurised fluid into a free airspace, and the thus resulting partial drop in pressure, the temperature of the aerosol decreases compared to the contact temperature of the oil stream in the heating zone of the reactor. The temperature of the aerosol close to the nozzle exit is in a range from 180 to 230° C., preferably in a range from 200 to 210° C.


In the following step (d), the resultant aerosol comprising the aroma composition having a grill-type flavour profile is discharged with the stream and transferred to a second line 9. The liquid oil phase separated from the aerosol is transferred to a third line 10.


In a further preferred variant of the method according to the present invention, a vacuum can be applied to the discharge line 9, creating a suction flow or low pressure, in order to accelerate the transport of the aerosol comprising the aroma composition having a grill-type flavour profile to the container 11, and controlled by a vacuum control unit. Applying a vacuum, preferably at a pressure of 200 to 800 mbar, more preferably at a pressure of 300 to 600 mbar, most preferably at a pressure of 450 to 500 mbar, increases the velocity of the aerosol.


In the following method step (e), the aerosol comprising the aroma composition having a grill-type flavour profile is discharged from the reactor and either collected in a collection vessel or absorbed on a solid carrier or liquid carrier.


A solid carrier is preferably used in a finely granulated or powder form which is preferably dry. Examples of materials suitable for the food industry include saccharides, polysaccharides and starches such as potato starch, rice starch, corn starch, etc., for example maltodextrin. Other powdered, finely divided food additives/ingredients may be used, such as for example silicas. Salts, sugar and/or spices or spice extracts are also particularly suitable. The carrier is suitably a liquid carrier. Oil-based or water-based carriers are preferred, depending on the ultimate use of the food ingredients. Water is a preferred carrier. Oils and mixtures of oils are particularly preferred.


A long shelf life is desirable in food products; to this end, dry solid carriers in powder form are preferred, as are stable oils. The latter are usually relatively low in polyunsaturated and monounsaturated fats/fatty acids and high in saturated fats/fatty acids. The oils preferably have a low level of oxidation.


Carrier oils suitable for the present invention include high-stability vegetable oils, i.e. saturated or partially saturated vegetable oils. Preferred oils include palm oil, soybean oil, peanut oil, olive oil, rapeseed oil, grapeseed oil, canola oil, corn oil, coconut oil, sesame oil, poppyseed oil, safflower oil, pumpkin seed oil, rice bran oil, almond oil, pecan oil, macadamia oil, pig fat (lard), beef fat (tallow), mutton fat (tallow), bacon dripping, chicken fat, turkey fat, butter or mixtures of two or more of these oils and/or fats.


More specifically, the carrier is preferably an oil having a high saturated fat content: high saturated fatty acid levels improve stability. Known saturated fat levels are: approximately 86 to 92% saturated fat for coconut; approximately 50 to 68% saturated fat for butter; approximately 39% saturated fat for lard; approximately 14% saturated fat for olive oil; and approximately 14% saturated fat for sesame. High levels are those which are 10% and above, preferably 30% and above. All of these oils can also be used as the oil or fat starting product or as part of the oil or fat starting product. The quality of the sunflower oil may also specifically be assessed on the basis of its ratio of oleic to linoleic acid. The fatty acid composition of sunflower oil is commonly 55 to 65% linoleic acid and 20 to 30% oleic acid, the remainder including other fatty acids, primarily palmitic acid and stearic acid. Sunflower oil is regarded as a stable oil, and most versions of it can be used in the invention. Particular versions used in the invention preferably contain even higher levels of oleic acid, particularly at least 50% oleic acid, more preferably at least 60% and even more preferably at least 70%. One known sunflower oil high in oleic acid has about 82% oleic acid.


Oils with lower levels of saturates, which are generally less useful as stable carrier oils but may be acceptable if stability is less of a required feature, include avocado oil, fish oil, linseed oil and some nut oils, including peanut oil.


Examples of preferred stable carrier oils include oils with a high oleic acid content, such as sunflower oil, lard, tallow and olive oil, and oils with a saturated fatty acid content of 20% or more, preferably 35% or more.


In the collection vessel or through absorption of the aerosol on a solid carrier or liquid carrier, the temperature of the aerosol further decreases, so that the aerosol condenses, and, thus liquefies. Thus, an active cooling of the aerosol in the method according to the present invention is not required.


The concentration of the aerosol in the solid carrier or liquid carrier is at least 0.5% by weight, based on the total weight of the aerosol/carrier composition. Preferably, the content of the aerosol in the solid carrier or liquid carrier is 1.0 to 10% by weight or more, based on the total weight of the aerosol/carrier-composition. The above ranges relate to an aerosol content preferably after 4 cycles.


The excess flowback liquid oil phase obtained by atomising and fragmenting the (preferably laminar) oil stream flows along the third line 10 and is collected in a process oil collection vessel 12. The excess flowback liquid oil phase can be recycled to the process oil reservoir 2 several times by means of pumps.


The reactor can also be run continuously, which is more efficient.


It has surprisingly been found that an aroma composition having a grill-type flavour profile with a pronounced impact and enhanced fatty/oily and/or smoky and/or roasted and/or burnt and/or animalic flavour notes but with a reduced waxy flavour note is achieved if the flowback liquid oil phase is subjected to the method according to the present invention several times. 2 to 25 cycles are possible with 2 to 6 being better.


In a more preferred variant of the method according to the present invention, the excess flowback liquid oil phase is recycled in an undiluted form, two to five times. In a particularly preferred variant, the flowback liquid oil phase is subjected to the method according to the present invention two to four times. In a most preferred variant, the flowback liquid oil phase is subjected to the method according to the present invention three or four times.


In a continuous operation of the method according to the present invention, the cycle time is calculated based on the time period required for one passage, dependent on the pumping speed.


It has surprisingly been found that if two to four cycles of the liquid oil phase are performed in the method according to the present invention, a significant increase of the compounds which contribute to a grill-type flavour profile with fatty/oily and/or smoky and/or roasted and/or burnt and/or animalic flavour notes is advantageously obtained, namely compounds such as capric acid, oleic acid, 2E-decenal, 2E-undecenal, 2E,4E-decadienal, and 1-dodecene, as shown in Table 4. However, if the liquid phase is subjected to the method according to the present invention four to six times, only a negligent increase of the compounds which contribute to a grill-type flavour profile is obtained.


This has also been confirmed in a comparative taste test panel, in which it was noted that the flavour profile of the aroma composition of the present invention was more enhanced and richer and higher in concentration. As shown in FIG. 7, the impact and fatty/oily and/or smoky and/or roasted and/or burnt and/or animalic flavour notes in particular are enhanced, while the waxy flavour note is significantly reduced as compared to the aroma composition of WO 2019/141357.


By contrast, in the method according to WO 2019/141357, the pyrolised or thermolised oil feedstock is not separated by atomization and, thus, fragmented but used as such. By the method according to the present invention, however, atomization and, thus, fragmentation of the pyrolised or thermolised oil feedstock into two phases is obtained. This results in an aerosol, which is more enhanced and richer in volatile compounds and which is advantageously not diluted with the oily phase, resulting in a higher flavour concentration and, thus, intensity.


The ratio of the amount of educt (aerosol), enriched in the more volatile components constituting the aroma composition having a grill-type flavour profile to the amount of the (recycled) liquid oil phase amounts 1:99, preferably 1:95.


In a second aspect, the present invention relates to an aroma composition having a grill-type flavour profile obtainable using the method according to the present invention, as described above.


The present invention thus relates to an aroma composition having a grill-type flavour profile obtainable by a method comprising or consisting of the following sequence of steps:

    • (a) providing a vegetable or animal oil or fat or a mixture thereof;
    • (b) transferring the product of step (a) to a reactor and heating the product to a temperature in the range of 310° C. to 400° C., in particular in the range of 350° C. to 380° C., and a pressure in the range of 2 to 6 bars, to obtain an oil stream;
    • (c) atomising the oil stream, thereby fragmenting the oil stream into a liquid oil phase and an aerosol comprising an aroma composition having a grill-type flavour profile, by an atomising device, preferably by a nozzle;
    • (d) transferring the aerosol containing the aroma to a second line and transferring the liquid oil phase to a third line;
    • (e) discharging the aerosol containing the aroma by collecting the aerosol or absorbing the aerosol on a solid carrier or in a liquid carrier; and
    • (f) optionally returning the liquid oil phase from step (d) to the reactor.


Preferably, the aroma composition obtained can be in combination with a solid or liquid carrier and/or other suitable food additive.


The aroma compositions having a grill-type flavour profile produced using the present invention have a high impact and marked characteristics. It has surprisingly been found that the aroma compositions according to the invention have a harmonious and balanced grill-like aroma profile. The aroma compositions according to the invention have improved sensory properties and are characterised by the fact that they provide and/or enhance fatty/oily and/or smoky and/or roasted and/or burnt and/or animalic flavour notes and suppress or reduce waxy flavour notes.


It has also surprisingly been found that the manufacturing process according to the invention prevents or suppresses or greatly reduces the formation of undecane, heptane, 2E-octene, 1-nonene, cyclooctene, and nonadecane, etc., which are harmful to the sensory properties.


The aroma composition described in the present application has flavouring notes which are markedly different from those obtained using the process described in WO 2019/141357, as can be seen from Table 4, even when using the same feedstock. In a comparative test in particular, the formation of compounds which contribute to a grill-type flavour profile, namely fatty/oily and/or smoky and/or roasted and/or burnt and/or animalic flavour notes, is enhanced; such compounds include capric acid, oleic acid, 2E-decenal, 2E-undecenal, 2E,4E-decadienal, and 1-dodecene, as can also be seen from Table 4. In comparison thereto, the aroma composition obtained using the process described in WO 2017/141357, however, comprises less grill-type flavours, such as fatty/oily, smoky, roasted and burnt, while the waxy and soapy aroma components are enhanced.


The aroma composition produced by the method described above can be determined using a standard analytic method such as gas chromatography.


In a comparative taste test panel in particular, it was noted that the flavour profile of the aroma composition of the present invention was more enhanced and richer and higher in concentration. As shown by the spider diagram in FIG. 8, the impact and fatty/oily and/or smoky and/or roasted and/or burnt and/or animalic flavour notes in particular are enhanced, while the waxy flavour note is significantly reduced, as compared to the aroma composition of WO 2019/141357.


The aroma composition according to the present invention having an improved grill-type flavour preferably comprises:

    • (a) at least one, preferably two, type(s) of linear or branched, saturated or unsaturated aliphatic C8 to C20 monocarboxylic acids;
    • (b) at least one, preferably two, type(s) of α,β-unsaturated C6 to C14 aldehydes; and
    • (c) at least one, preferably two, type(s) of α,β-unsaturated C6 to C14 alkenes.


The at least one type of linear of branched, saturated or unsaturated aliphatic C8 to C20 monocarboxylic acids is preferably selected from the group consisting of octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dedecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoid acid, nonadecanoic acid and eicosanoic acid.


The at least one type of α,β-unsaturated C6 to C14 aldehydes is preferably selected from the group consisting of C6-aldehyde, C7-aldehyde, C8-aldehyde, C9-aldehyde, C10-aldehyde, C11-aldehyde, C12-aldehyde, C13-aldehyde and C14-aldehyde.


The at least one type of α,β-unsaturated C6 to C14 alkenes is preferably selected from the group consisting of hexene, heptene, octene, nonene, decene, undecene, dodecene, tridecene and tetradecene.


In a more preferred variant of the present invention, component (a) in the aroma composition according to the present invention is selected from the group consisting of capric acid and oleic acid, and/or component (b) is selected from the group consisting of 2E-decenal, 2E-undecenal and 2E,4E-decadienal, and/or component (c) is selected from the group consisting of 1-dodecene. These compounds mainly contribute to fatty/oily and/or smoky and/or roasted and/or burnt and/or animalic flavour notes.


In another preferred variant, the components (a) and (b) and (c) are present in the aroma composition of the present invention in a weight ratio of 4.5 to 6.5:6.5 to 8.5:4.5 to 6.5, preferably in a weight ratio of 5.0 to 6.0:6.0 to 8.0:5.0 to 6.0.


In a more preferred variant, the aroma composition of the present invention comprises the following components:

    • capric acid at ≥150 ppm, in particular ≥230 ppm;
    • oleic acid at ≥250 ppm; in particular ≥350 ppm;
    • 2E-decenal at ≥30 ppm, in particular ≥400 ppm; and
    • 1-dodecene at ≥50 ppm, in particular ≥120 ppm.


In a particular preferred variant, the aroma composition of the present invention comprises the following components:

    • capric acid at ≥200 ppm, in particular ≥230 ppm;
    • oleic acid at ≥250 ppm; in particular ≥350 ppm;
    • 2E-decenal at ≥400 ppm, in particular ≥650 ppm;
    • 2E-undecenal at ≥220 ppm, in particular ≥400 ppm;
    • 2E,4E-decadienal at ≥20 ppm, in particular ≥100 ppm; and
    • 1-dodecene at ≥50 ppm, in particular ≥120 ppm.


As can be seen from Table 4, the aroma profile of the aroma composition having a grill-type flavour profile according to the present invention, is distinguished by the content of at least one type of linear or branched, saturated or unsaturated aliphatic C8 to C20 monocarboxylic acids, such as capric acid and oleic acid; at least one type of α,β-unsaturated C6 to C14 aldehydes, such as C6-aldehyde, C7-aldehyde, C8-aldehyde, 2E-heptenal, C9-aldehyde, 2E-oxtenal, 2E-nonenal, 2E-decenal, 2E-undecenal, 2E,4E-decadienal and 8Z-Heptadecenal; and at least one type of α,β-unsaturated C6 to C14 alkenes, such as 2E-hexen, 11-hexen, 1-hepten, 1-octene, 4E-decen, 1-dodecene, 1,3E-undecadiene and 8Z-heptadecene.


In a preferred variant, the grill-type flavour profile of the aroma composition is characterised by a significant content of capric acid, oleic acid, 2E-decenal, 2E-undecenal, 2E,4E-decadienal, and 1-dodecene, as described above. The concentration of said aldehydes and alkenes in the aroma composition is by a factor of at least 10 considerably higher compared to the aroma composition according to WO 2019/141357 A1, as can be derived from Table 4. This also applies to the concentration for capric acid and oleic acid, where the factor is at least 2.


The aroma composition produced using the present invention is very strong and distinctive. Due to its distinguishing properties and grill-type flavour profile, another aspect of the present invention relates to the use of the aroma composition for providing or enhancing a grill-type flavour and in particular imparting fatty/oily and/or smoky and/or roasted and/or burnt and/or animalic flavour notes and for simultaneously suppressing and/or reducing waxy flavour notes in a foodstuff, food supplement or animal feed and/or for preparing a foodstuff, food supplement or animal feed.


The aroma composition can be used in its own right or in combination with other flavourings, resulting in a blended product. The aroma composition of the present invention can also be used together with an appropriate liquid or solid carrier such as maltodextrin, starches or other carriers described in detail above or with one or more other suitable food additives as a flavouring agent. This flavouring agent may take the form of a liquid, solid, sauce, cream, pare or powder.


The aroma composition according to the present invention, or blended products or flavouring agents containing said aroma composition, can then be applied to meat, poultry, fish/seafood and/or other foodstuffs, including but not limited to dairy products, vegetables, deep-fried, surface-fried, baked, microwaved, barbequed, grilled or snack foods, in which it is desirable to impart or enhance a grill-type flavour.


Another aspect of the present invention therefore relates to a foodstuff, food supplement or animal feed comprising the aroma composition according to the present invention. The foodstuff is selected from, but not limited to, meat, poultry, fish/seafood, dairy products, vegetables, deep-fried, surface-fried, baked, microwaved, barbequed, grilled or snack foods. The aroma composition, or blended products or flavouring agents containing said aroma composition, are added to the foodstuff, food supplement or animal feed in a concentration sufficient to impart a grill-type flavour to said products. The aroma composition, or blended products containing said aroma composition, is/are in particular added to said consumer products in an amount of 0.01 to 0.3% by weight, preferably in an amount of 0.02 to 0.2% by weight, most preferably in an amount of 0.1%, based on the total weight of the formulation.


Finally, the present invention relates to an apparatus for producing an aroma composition having a grill-type flavour profile, with a reactor 1 comprising:

    • (i) a reservoir 2 for the vegetable or animal oil or fat or a mixture thereof, a pump 3, and a heater 4 adapted to heat the vegetable or animal oil or fat or mixture thereof to generate a heated oil stream;
    • (ii) an atomizing device, preferably a nozzle 6, adapted to atomise the heated oil stream in order to fragment the oil stream into a liquid oil phase and an aerosol comprising the aroma composition having a grill-type flavour profile;
    • (iii) optionally an inlet 7 adapted to inject a fluid or gas adjacent to the nozzle exit or to apply a vacuum adjacent to the nozzle exit;
    • (iv) a second line 9 adapted to discharge the aerosol containing the grill-type flavour;
    • (v) a third line 10 adapted to return the liquid oil phase to the reactor;
    • (vi) a container 11 adapted to collect the aerosol; and
    • (vii) a collection vessel 12 adapted to collect the liquid oil phase.


In a preferred variant of this apparatus, the heater 4 is an induction heater. This provides a smoother heating profile.


In a more preferred variant of the apparatus, the nozzle 6 is a Venturi nozzle, an example of which is depicted in FIG. 6.


Additional preferred variants and configurations of the apparatus according to the present invention are described in connection with the method according to the present invention.


LIST OF REFERENCE SIGNS






    • 1 reactor


    • 2 reservoir


    • 3 pump


    • 4 heater


    • 5 first line


    • 6 nozzle


    • 7 inlet


    • 8 vacuum control unit


    • 9 second line


    • 10 third line


    • 11 container


    • 12 collection vessel


    • 13 exhaust air/partial vacuum





Example 1: Characterisation of the Reaction Product

Each 0.5 g samples of the product (sunflower oil with a high oleic acid content) were extracted in 2 g water with 100 ppm 2-nonanol as internal standard, 1 h by SBSE (Stir Bar Sorptive Extraction) (Twister) and analysed using GS/MS.


One sample relates to an aroma composition prepared according to the present invention in which the liquid oil phase was recycled two times; another sample relates to an aroma composition prepared according to the present invention in which the liquid oil phase was recycled four times; and yet another sample relates to an aroma composition prepared according to the present invention in which the liquid oil phase was recycled six times.


For comparison, a sample of an aroma composition prepared according to the method of WO 2019/141357 A1 using the same feedstock, was prepared.















Instruments:



Mass spectrometer:
Aglient MSD 5977B


Gaschromatograph:
GC Agilent 8890


Autosampler:
MPS Robotic with TDU Option


Application system:
Gerstel TDU2 (Twister Desorption Unit)



with Cooled Injection System (CIS)







TDU_40_3_230_S10_150° C. M:


40° C. (1 min isotherm)-3° C./min-230° C. (25 min isotherm)


Split: 1:10 (TDU max temperature: 150° C.)








GC:



Oven Temperature
-> 40° C.


(Initial)



Program



#1 Rate
3° C./min


#1 Value
230° C.


#1 Hold Time
30 min


Front PTV Inlet He



Mode
Solvent Vent


Pressure
On 19.024 psi


Total Flow
On 29.4 mL/min


Septum Purge Flow
On 3 mL/min


Gas Saver
On 15 after 2 min mL/min


Purge Flow to Split Vent
24 mL/min at 0.03 min


(split 1:10)



Column Information
Agilent CP9205 VF-WAXms


Temperature Range
20-250° C. (260° C.)


Dimensions
30 m × 250 μm x 0.25 μm


In
Front PTV Inlet He


Out
MSD


(Initial)
40° C.


Flow
2.4 mL/min


Control Mode
Constant Flow


Front Detector FID



Makeup
N2


Heater
On 300° C.


H2 Flow
On 35 mL/min


Air Flow
On 350 mL/min


Makeup Flow
On 25 mL/min


Carrier Gas Flow Correction
Constant Makeup and Fuel Flow


Flame
On


MSD Transfer Line



Temperature
280° C.


(Initial)



FID Signals



Signal #1
Front Signal (FID)


Data Rate
20 Hz


GERSTEL CIS



Temperature program:



Initial Temperature
−20° C.


Equilibration Time
1.00 min


Initial Time
0.10 min


Ramp 1



Rate
12.00° C./s


End Temperature
250° C.


Hold Time
10.00 min


GERSTEL TDU



Temperature program:



Initial Temperature
30° C.


Delay Time
1.00 min


Initial Time
0.00 min


Ramp 1



Rate 1
60.0° C./min


End Temp 1
150° C.


Hold Time 1
8.00 min


TDU SETTINGS



Transfer Temperature
260° C.


Transfer Temp. Mode
Fixed


Desorption Mode
Splitless


Sample Mode
Remove Tube-no Standby Cooling


Standby Temperature
50° C.


General Information



Scan Parameters:



Low Mass
 25


High Mass
370


MSZones:



MS Source
230° C., maximum 250° C.


MS Quad
150° C., maximum 200° C.









The results of the gas chromatography are indicated in Table 4 below.



















TABLE 4












Grill-type
according to
according to
according to









aroma
invention,
invention,
invention,









according to
recycled
recycled
recycled


sorted according to






WO2019/141357 A1
2 times
4 times
6 times


order of elution (index)
Threshold
MS
Index
Index


SBSE
SBSE
SBSE
SBSE


Name MI
[ppb]
No.
L
DA
Scan
Time
[ppm]
[ppm]
[ppm]
[ppm]

























1-Pentene

E2860
1
499
82
2.354
0.000
7.805
0.000
0.000


2E-Hexene

E2776
1
510
104
2.327
0.000
0.000
114.498
0.000


1-Hexene

E2802
1
542
112
2.354
0.000
69.022
113.003
23.352


1,3E-Pentadiene

E7857
1
595
125
2.354
0.000
14.164
0.000
0.000


Heptane

E15342
700
687
159
2.551
11.607
0.000
0.000
23.352


1-Heptene

E2908
1
726
188
2.665
18.393
65.796
580.147
149.653


Propionaldehyde
170
E2800
1
753
213
2.753
0.000
0.241
0.000
0.000


Octane

E15343
800
787
244
2.897
8.973
0.000
61.638
6.529


Acrolein



821
293
3.092
0.000
40.397
0.000
0.000


1-Octene

E2806
823
826
303
3.134
8.527
0.000
298.479
205.146


1,3-Cyclohexadiene

E7600
868
843
332
3.332
0.000
4.116
0.000
0.000


2-Methyltetrahydrofuran

E5951
878
848
341
3.332
0.000
18.595
0.000
0.000


C4 Aldehyde
37.3
E2877
876
854
352
3.332
0.000
19.021
0.000
3.766


2E-Octene

E9866
854
855
354
3.345
2.188
0.000
0.000
0.000


2-Butanone
50000


887
410
3.573
0.000
0.426
0.000
0.000


Nonane

E196
900
888
412
3.576
8.795
0.593
82.371
49.717


2-Methylbutyraldehyde
0.9
E2910
911
911
471
3.868
0.000
2.503
0.000
0.000


Benzene

E2818
949
926
523
4.018
0.000
34.465
0.000
0.000


1-Nonene

E2803
946
927
525
4.037
18.103
0.000
0.000
0.000


Isopropylcyclohexane

E10041
985
959
631
4.466
1.027
0.000
0.000
0.000


C5 Aldehyde
76
E850
985
966
655
4.567
0.000
45.218
159.326
169.490


1,8-Nonadiene

E9955
988
974
681
4.67
2.009
0.000
0.000
0.000


Decane

E197
1000
987
724
4.842
2.121
0.000
25.216
41.682


1-Ethylcyclohexene



988
727
4.86
0.000
0.000
43.334
0.000


I Diethyltetrahydrofuran

E1436
1034
1009
820
5.246
0.000
12.199
30.446
62.272


Cyclooctene

E5247
1085
1020
877
5.47
20.067
0.000
0.000
0.000


1-Octine

E10043
1023
1025
903
5.586
0.000
0.000
147.932
0.000


4E-Decene

E9187
1031
1025
906
5.586
0.000
0.000
255.705
0.000


1-Decene



1025
906
5.586
0.000
0.000
0.000
188.573


Toluene

E2819
1043
1026
912
5.586
0.000
0.000
0.000
15.568


Diethyltetrahydrofuran P.2

E9625
1052
1028
922
5.651
0.000
23.082
0.000
0.000


3-Isopropylcyclohexene

E17990
1047
1045
1014
6.024
1.942
0.000
0.000
0.000


Butylcyclohexane

E4278
1
1057
1083
6.303
0.424
0.000
0.000
41.431


2-Hexanone
400
E739
1082
1070
1151
6.63
0.000
2.651
0.000
46.955


C6 Aldehyde
16
E188
1094
1072
1162
6.629
7.098
107.158
506.36
529.311


Undecane

E198
110
1088
1249
6.984
2.589
0.000
0.000
0.000


1-Hexen-3-one

E6968
1095
1090
1259
7.116
0.000
0.000
0.000
36.911


Ethylbenzene

E2813
1129
1116
1436
7.707
0.000
0.946
0.000
0.000


2E-Pentenal
1500
E1212
1129
1121
1474
7.898
0.000
2.651
0.000
0.000


5-Hexenal

E1108
1134
1123
1494
7.987
0.000
3.337
0.000
0.000


1-Undecene

E860
1141
1131
1549
8.203
42.232
16.185
393.73
479.594


3-Heptanone

E1481
1163
1142
1634
8.549
0.000
5.080
0.000
0.000


2-Heptanone
140
E778
1185
1172
1860
9.468
0.000
12.644
0.000
0.000


C7 Aldehyde
5.8
E189
1195
1175
1883
9.56
2.522
89.786
714.25
810.539


Limonene
162
E259
1201
1185
1965
9.894
13.839
5.376
87.788
0.000


Dodecane

E199
1200
1188
1985
9.977
3.125
0.000
43.147
0.000


1-Hepten-3-one

E1481
1196
1190
2001
10.039
0.000
5.061
39.224
78.342


Furfural
31
E174
1452
1194
2030
10.173
0.000
0.000
0.000
25.361


Prenyl formate

E1334
1190
1194
2033
10.173
0.000
0.000
0.000
87.884


Propylbenzene

E2820
1204
1198
2060
10.173
0.000
0.000
0.000
17.828


2E-Hexenal
27.2
E1953
1215
1209
2158
10.68
0.000
7.546
69.110
73.320


3,4-Heptanedione



1216
2221
10.998
0.000
0.000
28.951
0.000


6-Dodecene

E12203
1231
1221
2269
11.133
0.000
0.000
38.104
10.546


1-Dodecene

E4226
1240
1231
2355
11.483
6.808
0.000
146.998
153.922


6-Heptenal

E11087
1245
1233
2379
11.579
0.000
3.893
0.000
70.809


3-Octanone
1000
E223
1255
1243
2465
11.94
0.000
4.227
0.000
60.263


1,3E-Undecadiene

E7640
1255
1245
2479
11.987
57.567
6.785
700.622
587.817


Styrene
22
E5821
1248
1245
2487
12.014
0.000
2.614
9.339
12.806


2-Octanone
211
E257
1296
1273
2740
13.05
0.000
7.434
90.029
174.512


C8 Aldehyde
8
E190
1297
1278
2779
13.204
0.000
19.522
311.367
470.052


Tridecane

E200
1300
1288
2875
13.602
3.348
0.000
17.744
0.000


1,3-Octenone
0.01
E3038
1296
1290
2894
13.668
0.000
15.369
28.578
137.601


Butylbenzene

E2839
1306
1300
2982
14.01
0.000
0.000
19.425
112.993


2E-Heptenal
77
E1480
1334
1313
3106
14.532
3.371
36.819
221.711
304.078


1-Pentyl-1,3-

E11748
1347
1318
3153
14.726
11.875
0.000
29.512
0.000


Cyclohexadiene


6,5,2-Methylheptenone
50
E947
1334
1334
3260
15.162
0.000
1.798
0.000
0.000


Trans-4-Heptenoic acid

E21598
1322
1322
3272
15.212
0.000
2.688
30.072
0.000


methyl ester


1-Tridecene

E10111
1343
1331
3282
15.254
4.710
0.000
77.328
77.840


7-Octenal

E11081
1345
1335
3314
15.38
0.000
2.058
0.000
59.259


4-Methyl-3-cyclohexanone



1356
3522
16.227
0.000
0.000
0.000
78.091


Allyl capronate

E656
1372
1362
3577
16.458
0.000
0.000
0.000
93.910


2-Nonanone
7700
E1006
1399
1376
3716
17.021
0.000
2.633
0.000
0.000


2-Formyl-5-norbornene P.1

E1736
1393
1380
3751
17.209
0.000
1.372
0.000
0.000


C9 Aldehyde
18
E191
1383
1381
3763
17.209
0.000
29.366
765.995
888.630


Tetradecane

E10930
1400
1388
3827
17.471
3.214
0.000
0.000
0.000


1,3E,5E-Undecatriene

E2689
1391
1393
3876
17.619
5.826
6.155
11.954
7.282


Pentylbenzene

E2902
1423
1399
3932
17.893
5.134
0.000
99.555
152.667


2E-Octenal
90
E2560
1437
1420
4097
18.569
0.000
14.127
147.932
286.752


2-Formyl-5-norbornene

E1737
1435
1429
4165
18.848
0.000
7.267
0.000
0.000


Peak 2


2-Phenylpentane

E2836
1
1430
4168
18.835
0.000
0.000
0.000
37.162


1-Tetradecene

E20779
1443
1441
4251
19.196
10.246
2.596
0.000
166.979


2-Cyclohexyl-propanal

E10384
1444
1441
4255
19.214
0.000
0.000
0.000
53.232


5Z-Tetradecene

E8597
1443
1446
4289
19.349
0.000
0.000
123.463
0.000


1,3-Octenol
1
E2080
1446
1450
4325
19.499
0.000
1.780
15.503
43.440


1,13-Tetradecadiene

E7674
1488
1482
4565
20.471
0.000
0.000
0.000
176.72


Indene

E269
1464
1483
4575
20.51
0.000
0.482
0.000
0.000


2-Decanone
250
E1132
1488
1501
4712
21.072
0.000
2.225
110.05
159.46


2E,4E-Heptadienal
49
E5236
1482
1502
4728
21.072
0.000
0.519
0.000
0.000


C10 Aldehyde
6
E192
1502
1505
4762
21.27
0.000
1.409
96.006
160.93


Pentadecane

E15344
1500
1508
4795
21.41
8.348
1.187
97.127
0.000


Hexylbenzene

E1798
1515
1518
4916
21.899
1.116
0.000
0.000
35.656


Benzaldehyde
72
E239
1530
1524
4984
22.188
0.000
0.000
0.000
47.206


1-Pentadecene

E10539
1545
1528
5031
22.37
17.255
0.000
21.667
37.413


2E-Nonenal
6
E4839
1529
1534
5102
22.657
0.000
6.915
116.19
321.96


2-Octylfuran

E4141
1518
1535
5116
22.657
0.000
1.724
43.894
0.000


C8 Alcohol
130
E183
1550
1554
5349
23.663
0.000
1.594
0.000
85.373


3-Undecanone

E8468
1565
1558
5396
23.849
0.000
0.000
15.129
0.000


2E,4E-Octadienal

E2919
1574
1577
5619
24.76
0.000
0.426
0.000
40.175


2-Undecanone
91
E365
1608
1584
5700
25.084
0.000
0.612
50.805
94.663


1-Hexadecene

E4227
1645
1601
5898
25.902
4.063
0.000
57.342
76.835


2Z-Decenal

E5008
1606
1605
5934
26.041
0.000
0.000
33.434
100.49


2E-Decenal
17
E4567
1636
1623
6098
26.71
4.420
11.216
439.499
681.77


Pentacosadiene



1658
6405
27.956
0.000
0.000
232.544
0.000


2E,4E-Nonadienal
0.09
E4545
1687
1682
6623
28.844
0.000
0.723
22.787
57.501


Heptadecane

E15346
1700
1686
6655
28.976
5.603
0.000
0.000
42.435


2Z-Undecenal

E5009
1708
1701
6792
29.54
0.000
0.000
0.000
85.373


8Z-Heptadecene

E10194
1715
1702
6800
29.585
62.523
2.410
314.542
215.44


1-Heptadecene

E10543
1746
1705
6825
29.663
16.786
0.000
0.000
146.13


2E-Undecenal
20
E1761
1739
1730
7059
30.618
4.888
3.745
278.306
429.37


1-Undecen-3-ol



1736
7110
30.819
0.000
1.706
61.451
88.637


2E,4Z-Decadienal

E7706
1761
1745
7194
31.166
0.000
0.000
21.667
60.514


2E,4E-Decadienal
2.7
E4546
1809
1786
7563
32.668
4.018
1.947
53.980
119.02


1-Octadecene

E4229
1845
1796
7653
33.038
45.268
0.000
50.431
35.907


Capronic acid
3944


1825
7895
34.018
0.000
0.797
10.833
46.453


2E-Dodecenal
14
E1762
1844
1835
7982
34.373
0.000
0.000
20.359
46.453


Nonadecane

E15348
1900
1881
8358
35.898
0.737
0.000
0.000
0.000


γ-Octalactone
30


1887
8410
36.117
0.000
0.000
0.000
34.149


2E,4E-Undecadienal
1
E1750
1898
1893
8463
36.33
0.000
0.000
12.141
49.215


C14 Aldehyde
67
E959
1904
1899
8514
36.538
0.000
0.000
10.647
35.907


Neophytadiene

E14689
1924
1904
8550
36.682
8.103
0.000
0.000
0.000


Heptanoic acid
640
E4872
1947
1931
8767
37.562
0.000
2.929
52.673
92.655


Hept-6-enoic acid



1994
9286
39.672
0.000
2.243
41.839
84.117


Pentadecanal
430
E6200
2011
2003
9356
39.963
0.000
0.000
25.402
46.704


Caprylic acid
100
E1420
2038
2035
9606
40.976
1.027
1.428
25.963
56.246


Oct-7-enoic acid



2095
10074
42.88
0.000
0.000
20.173
55.743


1-Heneicosene

E18556
2148
2102
10128
43.096
2.165
0.000
0.000
0.000


Pelargonic acid
3000


2139
10402
44.216
0.000
1.298
19.239
50.973


2-Decen-1,4-olide



2154
10512
44.69
0.000
0.000
0.000
39.924


Non-8-enoic acid



2199
10845
46.019
0.000
0.000
16.250
43.942


Ethyl palmitate
2000


2228
11051
46.85
0.246
0.000
0.000
0.000


8Z-Heptadecenal

E11071
2256
2234
11094
47.031
20.826
2.095
156.71
139.358


Capric acid
3500
E2660
2253
2245
11173
47.353
56.541
26.103
259.44
255.114


8Z,11Z-Heptadecadienal



2281
11434
48.415
2.656
0.000
0.000
0.000


Dec-4-enoic acid



2295
11533
48.82
0.000
0.000
0.000
32.140


9-Decenoic acid

E5340
2341
2296
11534
48.818
2.723
2.447
22.040
24.356


3-Decenoic acid

E14316
2365
2304
11592
49.054
0.000
0.000
8.966
0.000


Benzoic acid

E2515
2432
2394
12208
51.555
2.879
0.575
0.000
12.806


10-Undecylenic acid

E5773
2436
2409
12305
51.957
0.000
0.000
7.845
20.088


Methyl oleate

E1635
2439
2414
12339
52.091
1.406
0.000
6.351
0.000


Ethyl oleate
867
E2259
2481
2450
12575
53.048
3.237
0.000
13.448
0.000


Lauric acid
10000
E3250
2473
2455
12609
53.188
5.848
0.649
0.000
0.000


Myristic acid
10000
E4873
2711
2665
13943
58.618
19.621
0.000
10.460
0.000


Palmitic acid

E4875
2
2880
15193
63.704
57.612
11.235
82.371
79.346


Stearic acid
20000
E4238
2

16748
70.014
11.094
0.000
0.000
0.000


Oleic acid

E14320
2

17039
71.213
140.090
28.718
290.821
389.450


Linolic acid

E13879
1

17576
73.381
18.706
0.000
0.000
0.000









817
904
9911
12141









Example 2: Characterisation of the Reaction Product

0.5 g rapeseed oil was extracted in 2 g water with 100 ppm 2-nonanol as internal standard, 1 h by SBSE (Stir Bar Sorptive Extraction) (Twister) and analysed using GS/MS.


The sample relates to an aroma composition prepared according to the present invention in which the liquid oil phase was recycled four times.


The sample was analysed under the same MS/GC analysis conditions as described in Example 1.


The results of the gas chromatography are indicated in Table 5 below and compared to the results of the high oleic sunflower oil sample according to Example 1. Table 5 is merely an excerpt of the main ingredients of the flavour profile but does not comprise all ingredients of the flavour profile.














TABLE 5









High oleic







sunflower oil
Rapeseed oil






recycled 4
recycled 4






times
times



Threshold


SBSE
SBSE


Name MI
[ppb]
Index L
Time
[ppm]
[ppm]




















HEXEN, 2E-

1
2.327
114.498
0.000


HEXEN, 1-

1
2.327
113.003
165.583


HEPTEN, 1-

1
2.554
580.147
368.869


OCTANE

800
2.758
61.638
177.710


OCTENE, 1-

823
3.017
298.479
251.020


CYCLOHEXADIEN, 1,3-

868
3.137
0.000
119.392


NONANE

900
3.418
82.371
95.139


ETHYLFURAN, 2-

943
3.594
0.000
0.000


CYCLOHEXENE, 1-

900
3.601
0.000
34.065


METHYL-


NONENE, 1-

946
3.79
0.000
152.244


BENZENE

949
3.79
0.000
102.745


ALCOHOL
13000
934
3.867
198.176
873.004


ALDEHYDE C 5
76
985
4.531
159.326
0.000


DECANE

1000
4.768
25.216
0.000


ETHYLCYCLOHEXEN, 1-


4.86
43.334
0.000


DIETHYL

1034
5.202
30.446
0.000


TETRAHYDROFURAN I


CYCLOHEXADIENE, 1-

1013
5.226
0.000
12.898


METHYL-1,4-


TOLUENE

1043
5.429
0.000
96.021


OCTIN, 1-

1023
5.586
147.932
0.000


DECEN, 4E-

1031
5.586
255.705
0.000


DECENE, 1-

1040
5.839
0.000
16.095


DECENE, 1-

1040
6.037
0.000
113.659


ISOAMYL FORMATE

1073
6.404
0.000
0.000


ALDEHYDE C 6
16
1094
6.622
506.368
43.215


ETHYLBENZENE

1129
7.436
0.000
55.011


UNDECEN, 1-

1141
8.309
393.738
342.190


ALDEHYDE C 7
5.8
1195
9.65
714.257
44.758


BENZENE, PROPYL-

1204
9.897
0.000
60.743


LIMONENE
162
1201
9.914
87.788
30.096


HEPTEN-3-ON, 1-

1196
10.053
39.224
0.000


DODECANE

1200
10.135
43.147
0.000


HEXENAL, 2E-
27.2
1215
10.681
69.110
0.000


HEPTANEDIONE, 3,4-


10.998
28.951
0.000


DODECENE, 6-

1231
11.133
38.104
68.129


DODECENE, 1-

1240
11.674
146.998
69.232


STYRENE
22
1248
12.157
9.339
13.670


UNDECADIENE, 1,3E-

1255
12.157
700.622
395.988


OCTANONE, 2-
211
1296
13.093
90.029
0.000


ALDEHYDE C 8
8
1297
13.299
311.367
0.000


OCTENONE, 1,3-
0.01
1296
13.823
28.578
0.000


TRIDECANE

1300
13.823
17.744
0.000


CYCLOHEXADIENE, 1-

1347
14.01
29.512
109.580


PENTYL-1,3-


BENZENE, BUTYL-

1306
14.01
19.425
34.175


HEPTENAL, 2E-
77
1334
14.569
221.711
22.379


HEPTENSAEUREMETHYLESTER,


15.232
30.072
0.000


TRANS-4-


TRIDECENE, 1-

1343
15.476
77.328
0.000


NONANONE, 2-
7700

16.659
0.000
0.000


UNDECATRIENE, 1,3,5-

1378
17.197
0.000
149.708


UNDECATRIEN, 1,3E,5E-

1391
17.392
11.954
0.000


ALDEHYDE C 9
18
1383
17.392
765.995
0.000


BENZENE, PENTYL-

1423
17.985
99.555
39.136


OCTENAL, 2E-
90
1437
18.641
147.932
0.000


TETRADECENE, 5Z-

1443
19.349
123.463
62.287


OCTENOL, 1,3-
1
1446
19.528
15.503
0.000


INDENE

1464
20.029
0.000
6.284


DECANONE, 2-
250
1488
21.149
110.015
0.000


ALDEHYDE C10
6
1502
21.366
96.006
0.000


BENZENE, HEXYL-

1515
21.377
0.000
10.804


PENTADECANE

1500
21.56
97.127
69.232


NONENAL, 2E-
6
1529
22.412
116.179
0.000


PENTADECENE, 1-

1545
22.567
21.667
94.808


FURAN, 2-OCTYL-

1518
22.721
43.894
0.000


UNDECANONE, 3-

1565
23.849
15.129
0.000


UNDECANONE-2
91
1608
25.149
50.805
0.000


DECENAL, 2Z-

1606
26.041
33.434
0.000


DECENAL, 2E-
17
1636
26.85
439.499
31.529


HEXADECENE, 1-

1645
27.061
57.342
62.507


HEPTADECANE

1700
28.522
0.000
0.000


NONADIENAL, 2E,4E-
0.09
1687
28.864
22.787
0.000


HEPTADECENE, 1-

1746
29.258
0.000
70.775


HEPTADECENE, 8Z-

1715
29.715
314.542
341.749


UNDECENAL 2E-
20
1739
30.727
278.306
0.000


UNDECEN-3-OL, 1-

1747
30.866
61.451
0.000


DECADIENAL, 2E,4Z

1761
31.166
21.667
0.000


DECADIENAL, 2E,4E-
2.7
1809
32.691
53.980
27.560


OCTADECENE, 1-

1845
33.036
50.431
0.000


CAPRONIC ACID
3944
1840
34.023
10.833
11.245


DODECENAL, 2E-
14
1844
34.373
20.359
0.000


UNDECADIENAL, 2E,4E-
1
1898
36.33
12.141
0.000


ALDEHYDE C 14
67
1904
36.538
10.647
0.000


HEPTANOIC ACID
640
1947
37.564
52.673
49.609


PENTADECANAL
430
2011
39.963
25.402
0.000


CAPRYLIC ACID
100
2038
40.971
25.963
31.750


PELARGONIC ACID
3000
2149
44.22
19.239
16.206


HEPTADECENAL, 8Z-

2256
47.095
156.711
36.710


CAPRIC ACID
3500
2253
47.384
259.441
169.001


DECENOIC ACID 9-

2341
48.814
22.040
26.017


DECENOIC ACID-3

2365
49.054
8.966
0.000


10-UNDECYLENIC ACID

2436
51.957
7.845
0.000


METHYL OLEATE

2439
52.097
6.351
0.000


ETHYL OLEATE
867
2481
53.054
13.448
0.000


MYRISTIC ACID
10000
2711
58.599
10.460
0.000


PALMITIC ACID

2
63.689
82.371
121.927


STEARIC ACID
20000

68.895
0.000
30.427


OLEIC ACID

2
71.226
290.821
288.503






17594
10191









As can be derived from Table 5, the grill-type flavour profile of the rapeseed oil is also characterised by a significant content of capric acid, oleic acid, 2E-decenal, and 1-dodecene, despite differences in the fatty acid composition of the starting material, and, thus, resulting in a grill-type flavour profile that is dominated by grill-type flavour notes characterised by extremely fatty/oily and/or smoky and/or roasted and/or burnt and/or animalic flavour notes.


Example 3: Sensory Evaluation

A sample of an aroma composition according to the present invention as obtained in Example 1 (4 cycles) was subjected to a sensory evaluation.


For comparison, a sample of an aroma composition prepared according to WO 2019/141357 A1 as obtained in Example 1 was used.


The odours of the aroma composition (0.1% in water) and their intensities were evaluated and compared by an expert panel of 4 persons (flavorists) on a scale of 1 to 8. 30 ml of the test solution was presented in a 80 ml plastic cup for the sensory evaluation.


The flavour notes used as parameters were: fatty/oily, soapy, waxy, burnt, roasted, phenolic, smoky, animalic, green, and impact.


As can be seen from the spider diagram in FIG. 7, the aroma composition according to the present invention has a higher impact, and the fatty/oily and/or smoky and/or roasted and/or burnt and/or animalic flavour notes are considerably enhanced, whereas the waxy flavour notes are suppressed compared to the aroma composition according to the prior art WO 2019/141357.

Claims
  • 1. A method for preparing an aroma composition having a grill-type flavour profile, comprising the following sequence of steps: (a) providing a vegetable or animal oil or fat or a mixture thereof;(b) transferring the product of step (a) to a reactor and heating the product to a temperature in the range of 310° C. to 400° C., and a pressure in the range of 2 to 6 bars, to obtain an oil stream;(c) atomising the oil stream, thereby fragmenting the oil stream into a liquid oil phase and an aerosol comprising an aroma composition having a grill-type flavour profile, by an atomising device;(d) transferring the aerosol containing the aroma to a second line and transferring the liquid oil phase to a third line;(e) discharging the aerosol containing the aroma by collecting the aerosol or absorbing the aerosol on a solid carrier or in a liquid carrier; and(f) optionally returning the liquid oil phase from step (d) to the reactor.
  • 2. The method according to claim 1, wherein the product of step (a) is heated in step (b) to a temperature in the range of 360° C. to 370° C. and/or a pressure in the range of 3 to 4 bars, and/or for 10 to 30 seconds.
  • 3. The method according to claim 1, wherein the method comprises two to five cycles.
  • 4. The method according to claim 1, wherein the process is performed without purging air.
  • 5. The method according to claim 1, wherein the atomising step is performed by flash evaporation and/or by a Venturi nozzle.
  • 6. The method according to claim 1, wherein step (c) further comprises injecting a fluid or gas adjacent to the nozzle exit or applying a vacuum at a pressure in the range of 200 to 800 mbar adjacent to the nozzle exit.
  • 7. The method according to claim 1, wherein the vegetable or animal oil or fat of step (a) is selected from the group consisting of unsaturated, saturated or partially saturated palm oil, palm kernel oil, soybean oil, sunflower oil, peanut oil, olive oil, rapeseed oil, grapeseed oil, canola oil, corn oil, coconut oil, sesame oil, poppyseed oil, safflower oil, pumpkin seed oil, rice bran oil, almond oil, pecan oil, macadamia oil, cottonseed oil, linseed oil, pig fat (lard), beef fat (tallow), mutton fat (tallow), bacon dripping, chicken fat, turkey fat, butter and mixtures of two or more of these oil and/or fats.
  • 8. An aroma composition obtainable using the method according to claim 1, optionally in combination with a solid or liquid carrier and/or other suitable food additives.
  • 9. The aroma composition according to claim 8, comprising: (a) at least one type(s) of linear or branched, saturated or unsaturated aliphatic C8 to C20 monocarboxylic acids;(b) at least one type(s) of α,β-unsaturated C6 to C14 aldehydes; and(c) at least one type(s) of α,β-unsaturated C6 to C14 alkenes.
  • 10. The aroma composition according to claim 9, wherein: component (a) is selected from the group consisting of capric acid and oleic acid; and/orcomponent (b) is selected from the group consisting of 2E-decenal, 2E-undecanal and 2E,4E-decadienal; and/orcomponent (c) is selected from the group consisting of 1-dodecene.
  • 11. The aroma composition according to claim 10, wherein the components (a) and (b) and (c) are present in a weight ratio of 4.5 to 6.5:6.5 to 8.5:4.5 to 6.5.
  • 12. The aroma composition according to claim 10, comprising the following components: capric acid at ≥150 ppm, in particular ≥230 ppm;oleic acid at ≥250 ppm, in particular ≥350 ppm;2E-decenal at ≥30 ppm, in particular ≥400 ppm; and1-dodecene at ≥50 ppm, in particular ≥120 ppm.
  • 13. A method of providing or enhancing a grill-type flavour profile in a foodstuff, food supplement, or animal feed comprising applying or adding the aroma composition according to claim 8 to the foodstuff, food supplement or animal feed.
  • 14. A foodstuff, food supplement or animal feed comprising the aroma composition according to claim 8.
  • 15. Apparatus for producing an aroma composition having a grill-type flavour profile, with a reactor comprising: (i) a reservoir for vegetable or animal oil or fat or a mixture thereof, a pump, and a heater adapted to heat the vegetable or animal oil or fat or mixture thereof to generate a heated oil stream;(ii) an atomizing device adapted to atomise the heated oil stream in order to fragment the oil stream into a liquid oil phase and an aerosol comprising an aroma composition having a grill-type flavour profile;(iii) optionally an inlet adapted to inject a fluid or gas adjacent to the exit of the atomizing device or to apply a vacuum adjacent to the exit of the atomizing device;(iv) a second line adapted to discharge the aerosol containing the grill-type flavour;(v) a third line adapted to return the liquid oil phase to the reactor;(vi) a container adapted to collect the aerosol; and(vii) a collection vessel adapted to collect the liquid oil phase.
  • 16. The apparatus according to claim 15, wherein the heater is an induction heater.
  • 17. The apparatus according to claim 15, wherein the atomizing device is a nozzle.
  • 18. The method according to claim 1, wherein the atomising device is a nozzle.
  • 19. The apparatus according to claim 15, wherein the nozzle is a Venturi nozzle.
  • 20. The method according to claim 13, wherein the providing or enhancing a grill-type flavour profile comprises providing or enhancing a fatty/oily and/or smoky and/or roasted and/or burnt and/or animalic flavour and simultaneously suppressing and/or reducing a waxy flavour in the foodstuff, food supplement or animal feed.
PCT Information
Filing Document Filing Date Country Kind
PCT/EP2020/077596 10/1/2020 WO