Patent Grant
7674365
This invention relates generally to a composition useful in processing and handling petroleum products containing asphaltenes, including crude oil.
Certain petroleum products, including, e.g., heavy crude oils and residual fuel oils, which include materials referred to as “tars,” “petroleum tars” or “tar sands,” are rich in asphaltenes, metals and resins. The presence of these types of compounds can lead to various problems in the recovery, transportation, treatment and refining of petroleum hydrocarbons, including increased viscosity, formation of stable emulsions, fouling and corrosion. Residual fuel oils are prone to formation of asphaltene-containing precipitates during storage, or when fuel oils from different sources are mixed, especially when one of the oils has a high paraffin content. U.S. Pat. No. 6,402,934 discloses stabilization of asphaltenes in petroleum products using amine-chelate complexes. However, there is a need for improved additives to further enhance stabilization of asphaltenes.
The problem addressed by this invention is to find an improved composition suitable for stabilization of asphaltenes in petroleum products containing asphaltenes.
The present invention is directed to a composition comprising: (i) a chelating aminocarboxylic acid-C8-C22 amine complex; (ii) a C15-C21 bis(2-hydroxyethyl)amide; and (iii) a C15-C44 imidazoline compound.
All percentages are weight percentages based on the entire composition, unless otherwise indicated. An “alkyl” group is a hydrocarbyl group having from one to twenty-two carbon atoms in a linear, branched or cyclic arrangement. Substitution on alkyl groups of one or more of halo, cyano, alkyl, or alkoxy is permitted; alkoxy groups may in turn be substituted by one or more halo substituents. Preferably, alkyl groups are unsubstituted. An “alkenyl” group is an alkyl group having at least one carbon-carbon double bond. A “heteroalkyl” group is an alkyl group in which at least one carbon has been replaced by O, NR, or S, wherein R is hydrogen, alkyl, heteroalkyl, aryl or aralkyl. An “aryl” group is a substituent derived from an aromatic hydrocarbon compound. An aryl group has a total of from six to twenty ring atoms, and has one or more rings which are separate or fused. An “aralkyl” group is an “alkyl” group substituted by an “aryl” group. A “heterocyclic” group is a substituent derived from a heterocyclic compound having from five to twenty ring atoms, at least one of which is nitrogen, oxygen or sulfur. Preferably, heterocyclic groups do not contain sulfur. Substitution on aryl or heterocyclic groups of one or more of halo, cyano, alkyl, heteroalkyl, alkoxy or the aforementioned polar groups is permitted, with substitution by one or more halo groups being possible on alkyl, heteroalkyl or alkoxy groups. An “aromatic heterocyclic” group is a heterocyclic group derived from an aromatic heterocyclic compound. Preferably, heterocyclic groups in compounds used in this invention are aromatic heterocyclic groups.
The chelating aminocarboxylic acid-C8-C22 amine complexes of the present invention are generally formed by heating the C8-C22 amine with the chelating aminocarboxylic acid. The amounts of amine and chelating aminocarboxylic acid used to form the complexes can vary greatly, depending on several factors such as the particular application, and the composition and physical properties of the heavy crude oil (HCO) or other petroleum product; however, in general the molar equivalent ratio of amine to acid equivalent of chelating aminocarboxylic acid will be in the range of 10:1 to 1:2. It is preferred that the ratio is 6:1 to 1:1. Most preferred is a ratio of 5:1 to 4.5:1.
A chelating aminocarboxylic acid is a compound having an amine group, and having at least two carboxylic acid groups that can form coordinate bonds to a single metal atom. Preferred chelating aminocarboxylic acids useful in the present invention include, e.g., ethylenediaminetetraacetic acid (EDTA), hydroxyethylethylenediaminetriacetic acid, nitrilotriacetic acid (NTA), N-dihydroxyethylglycine and ethylenebishydroxyphenyglycine. Particularly preferred chelating aminocarboxylic acids are EDTA and NTA, and EDTA is most preferred.
Preferred C8-C22 amines useful in the present invention are n-octylamine, 2-ethylhexylamine, t-octylamine, n-decylamine, tertiary-alkyl primary amines (either singly or in any combinations thereof), tridecylamine, n-undecylamine, lauryl amine, hexadecylamine, heptadecylamine, octadecylamine, decenylamine, dodecenylamine, palmitoleylamine, oleylamine, linoleylamine, eicosenylamine and polyetheramine; and polyalkylamines such as polyisobutyleneamine. Commercially available mixtures of suitable primary aliphatic amines in the C12-C18 range include ARMEEN O and ARMEEN OD (Akzo Nobel; Stratford, Conn.). It is preferred to use oil-soluble aliphatic amines in which the aliphatic group is a tertiary aliphatic group, most preferably a tertiary alkyl group, e.g., tertiary-alkyl primary amines. Commercially available mixtures of tertiary-alkyl primary amines include 1,1,3,3-tetramethylbutylamine (PRIMENE TOA); an isomeric mixture of C16 to C22 tertiary alkyl primary amines (PRIMENE JM-T); an isomeric mixture of C8 to C10 tertiary alkyl primary amines (PRIMENE BC-9); an isomeric mixture of C10 to C15 tertiary alkyl primary amines (PRIMENE 81-R); or mixtures thereof. (Rohm and Haas Company; Philadelphia, Pa.).
Preferably, the C15-C21 bis(2-hydroxyethyl)amide has the following formula
wherein R is C15-C21 alkyl, C15-C21 alkenyl, or a mixture thereof. Preferably, R is C15-C17 alkyl, C15-C17 alkenyl, or a mixture thereof, most preferably R is acyclic linear alkyl and/or alkenyl, including, but not limited to the alkenyl group of oleic acid (heptadec-8(Z)-ene-1-yl), n-heptadecyl, and mixtures of C15-C17 acyclic linear alkyl and/or alkenyl groups, e.g., those alkyl/alkenyl mixtures existing in naturally-occurring C16-C18 fatty acids.
Preferably, in a C15-C44 imidazoline compound useful in the present invention, the imidazoline ring has at least one C15-C22 alkyl or alkenyl side chain. In one embodiment of the invention, the imidazoline ring also has an alkenylamide side chain having from 10 to 24 carbon atoms. Preferably, the C15-C44 imidazoline compound is a C30-C44 imidazoline compound. In one preferred embodiment, the imidazoline compound is a reaction product of a fatty acid and a polyamine. Preferred polyamines include, e.g., ethylenediamine, diethylenetriamine, and hydroxyethyl ethylenediamine. Preferred fatty acids include, e.g., C12-C20 alkyl and/or alkenyl carboxylic acids, including polyunsaturated acids. Particularly preferred fatty acids are oleic, linoleic and fatty acid mixtures derived from tall oil, soybean or palm oils. Preparation of fatty acid-polyamine reaction products is known, and is disclosed, e.g., in WO 01/25214.
In one preferred embodiment in which the imidazoline compound is a reaction product of a fatty acid and a polyamine, the imidazoline is derived from oleic acid and diethylenetriamine, and has the following structure
Preferably, the composition of the present invention comprises 10-80% of a chelating aminocarboxylic acid-C8-C22 amine complex, 10-80% of a C15-C21 bis(2-hydroxyethyl)amide, and 15-80% of a C15-C44 imidazoline compound, with all amounts being exclusive of solvents; more preferably 10-70% of a chelating aminocarboxylic acid-C8-C22 amine complex, 10-70% of a C15-C21 bis(2-hydroxyethyl)amide, and 15-70% of a C15-C44 imidazoline compound. Most preferably, the composition comprises 12-65% of a chelating aminocarboxylic acid-C8-C22 amine complex, 12-65% of a C15-C21 bis(2-hydroxyethyl)amide, and 20-65% of a C15-C44 imidazoline compound. In one preferred embodiment of the invention, the composition comprises 14-30% of a chelating aminocarboxylic acid-C8-C22 amine complex, 14-30% of a C15-C21 bis(2-hydroxyethyl)amide, and 50-65% of a C15-C44 imidazoline compound.
For the purposes of this invention petroleum products containing asphaltenes can be any crude or refined product derived from petroleum, wherein the product contains asphaltenes. Preferably, the petroleum product containing asphaltenes is heavy crude oil or residual fuel oil. Residual fuel oil is the heavier fuel oil that remains after distilling light hydrocarbons and distillate fuel oils in refinery operations. Residual fuel oils typically are designated as number 5 or number 6 fuel oil, and conform to ASTM Specifications D 396 and D 975, and Federal Specification VV-F-815C. Number 6 fuel oil for marine applications is also known as Bunker C fuel oil.
In addition to dispersing asphaltenes, the composition of the present invention typically also increases demulsibility, reduces viscosity, reduces sediment formation, reduces surface fouling and reduces corrosion. For crude oil recovery, the composition of the present invention can be injected directly into an injection well, or preferably diluted with solvent prior to injection. Suitable solvents include but are not limited to: petroleum distillates such as kerosene and gas oil; linear and branched aliphatic solvents such as pentane, hexanes, mixtures of nonanes and 2-ethylhexanes; cycloaliphatic mixtures commonly known as naphtha; aromatic solvents such as toluene, xylenes and commercial aromatic solvent mixtures; esters; ethers; alcohols such as ethanol, isopropanol, octanol and dodecanol; ketones such as acetone, cyclohexanone and acetophenone; and other polar solvents. Two preferred solvents are AROMATIC 150 solvent, a mixture with a boiling range of 184-204° C. which contains xylene isomers; and AROMATIC 100 solvent, a mixture with a boiling range of 160-171° C. which comprises >99% of various aromatic hydrocarbons, both of which are available from Exxon Mobil Chemical Co., Houston Tex. Preferred dilutions are 0.01 to 50 wt % of the compound in the solvent, more preferred dilutions being 0.01 to 20 wt %, more preferred dilutions being 0.1 to 10%, and most preferred dilutions being 1 to 10 wt %.
To a 3-necked round bottom flask equipped with a mechanical stirrer, heating mantle, addition funnel and reflux condenser was added 18.4 by wt % of an isomeric mixture of C10 to C15 tertiary alkyl primary amines. The mixture was heated to about 60° C., at which time 1.6 by wt % of EDTA was slowly added to the amine mixture through the additional funnel, with stirring, to maintain the temperature between 80 and 100° C. When addition was completed, the reaction temperature was raised to 120-140° C. and maintained for about an hour (or until the EDTA was completely dissolved). The pH of the mixture was checked, and if below 8.5, additional amine was added. The reaction mixture was then allowed to cool to room temperature. Upon cooling, this mixture was diluted to 20 wt % with Aromatic 100 solvent (63 wt %), isopropanol (2 wt %), 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-(10 wt %) and surfactant (nonylphenol ethoxylate, 4 moles, 5 wt %), and mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, heating mantle, addition funnel and reflux condenser was added 7.5 by wt % of an isomeric mixture of C10 to C15 tertiary alkyl primary amines that was heated to about 60° C. at which time 2.5 wt % of EDTA was slowly added to the amine mixture through the addition funnel, with stirring. When addition was completed, the reaction temperature was maintained at 100° C. for about four hours, or until the EDTA was completely dissolved.
To a 3-necked round bottom flask equipped with a mechanical stirrer, heating mantle, addition funnel and reflux condenser was added 5 wt % of the product of Example 2, 45 wt % of toluene, and 50 wt % of aromatic 100 solvent were mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, heating mantle, addition funnel and reflux condenser was added 5 wt % of the product of Example 2, 45 wt % of heavy aromatic naphtha solvent, and 50 wt % of Aromatic 100 solvent were mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, heating mantle, addition funnel and reflux condenser was added 4.5 wt % of the product of Example 2, 40.5 wt % of toluene, 44 wt % of Aromatic 100 solvent, 10 wt % of 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-, and 1 wt % of nonylphenol ethoxylate (4 mol) were mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, heating mantle, addition funnel and reflux condenser was added 4 wt % of the product of Example 2, 36 wt % of toluene, 44 wt % of aromatic 100 solvent, 15 wt % of 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-, and 1 wt % of nonylphenol ethoxylate (4 mol) were mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, heating mantle, addition funnel and reflux condenser was added 4 wt % of the product of Example 2, 36 wt % of toluene, 39 wt % of solvent light diesel, 10 wt % of xylene, 10 wt % of 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-, and 1 wt % of nonylphenol ethoxylate (4 mol) were mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, heating mantle, addition funnel and reflux condenser was added 4.5 wt % of the product of Example 2, 40.5 wt % of toluene, 34 wt % of light diesel, 10 wt % of xylene, 10 wt % of 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-, and 1 wt % of nonylphenol ethoxylate (4 mol) were mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, heating mantle, addition funnel and reflux condenser was added 4 wt % of the product of Example 2, 36 wt % of toluene, 34 wt % of light diesel, 10 wt % of xylene, 15 wt % of 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-, and 1 wt % of nonylphenol ethoxylate (4 mol) were mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, heating mantle, addition funnel and reflux condenser was added 4 wt % of the product of Example 2, 36 wt % of heavy aromatic naphtha solvent, 49 wt % of Aromatic 100 solvent, 10 wt % of 9-octadecenamide, N-{2-[2-(8-heptadecenyl) 4,5-dihydro-1H-imidazol-1-yl]ethyl}-, and 1 wt % of nonylphenol ethoxylate (4 mol) were mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, heating mantle, addition funnel and reflux condenser was added 4.5 wt % of the product of Example 2, 40.5 wt % of heavy aromatic naphtha solvent, 44 wt % of Aromatic 100 solvent, 10 wt % of 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-, and 1 wt % of nonylphenol ethoxylate (4 mol) were mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, addition funnel and reflux condenser was added 10 wt % of the product of Example 2, 90 wt % of toluene, were mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, heating mantle, addition funnel and reflux condenser was added 7 wt % of the product of Example 2, 63 wt % of toluene, 15 wt % of Aromatic 100 solvent, 10 wt % of 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-, 2 wt % of isopropanol, and 5 wt % of nonylphenol ethoxylate (6 mol) were mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, heating mantle, addition funnel and reflux condenser was added 6 wt % of the product of Example 2, 54 wt % of toluene, 23 wt % of Aromatic 100 solvent, 10 wt % of 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-, 2 wt % of isopropanol, and 5 wt % of nonylphenol ethoxylate (6 mol) were mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, addition funnel and reflux condenser was added 10 wt % of N,N-bis-(2-hydroxyethyl)oleamide, 90 wt % of hexanes. The mixture was mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser was added 50 wt % of Example 15, and 50 wt % of Aromatic 100 solvent. The mixture was mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser was added 40 wt % of Example 15, 49 wt % of Aromatic 100 solvent, 10 wt % of 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-, and 1 wt % of surfactant. The mixture was mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser was added 40 wt % of Example 15, 44 wt % of Aromatic 100 solvent, 15 wt % of 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-, and 1 wt % of surfactant. The mixture was mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser was added 70 wt % of Example 15, 13 wt % of Aromatic 100 solvent, 10 wt % of 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-, 2 wt % of isopropanol, and 5 wt % of surfactant. The mixture was mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser was added 20 wt % of Example 15, 63 wt % of Aromatic 100 solvent, 2 wt % of 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-, 10 wt % isopropanol, and 5 wt % of surfactant. The mixture was mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser was added 27 wt % of Example 14, 63 wt % of Aromatic 100 solvent, 5 wt % of 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-, and 5 wt % of surfactant. The mixture was mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser was added 1.6 wt % of Example 2, 1.6 wt % of N,N-bis-(2-hydroxyethyl)oleamide, 14.4 wt % of toluene, 14.4 wt % of hexanes, 63 wt % of Aromatic 100 solvent, and 5 wt % of 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-. The mixture was mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser was added 3.5 wt % of Example 2, 3.5 wt % of N,N-bis-(2-hydroxyethyl)oleamide, 31.5 wt % of toluene, 31.5 wt % of hexanes, 13 wt % of Aromatic 100 solvent, 2 wt % of isopropanol, and 5 wt % of 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-. The mixture was mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser was added 5 wt % of Example 2, 5 wt % of N,N-bis-(2-hydroxyethyl)oleamide, 45 wt % of toluene, and 45 wt % of hexanes. The mixture was mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, addition funnel, heating mental, and a reflux condenser was added 4.6 wt % of C16 to C22 tertiary alkyl primary amines. The mixture was heated to about 60° C., at which time 0.4 wt % of EDTA was slowly added to the amine mixture through the addition funnel, with stirring, to maintain the temperature between 80 and 100° C. When the addition was completed, the reaction temperature was raised to 120-140° C. and maintained for about an hour (or until the EDTA was completely dissolved). The reaction mixture was then cooled to room temperature. Upon cooling, to this mixture was added, 20 wt % of Example 2, 75 wt % of Aromatic 150 solvent. The mixture was mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser was added 12.5 wt % of Example 25, 50 wt % of example 24, and 37.5 wt % of Aromatic 150 solvent. The mixture was mixed until homogeneous.
To a 3-necked round bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser was added 20.97 wt % of tertiary alkyl nonyl amine. The mixture was heated to 60° C. at which time 1.49 wt % of EDTA was slowly added to the amine mixture through the addition funnel, with stirring, to maintain the temperature between 80 and 100° C. When the addition was completed, the reaction temperature was raised to 120-140° C. and maintained for about an hour (or until the EDTA was completely dissolved). The reaction mixture was then cool to room temperature. To this mixture, 25.48 wt % of toluene, 50 wt % of Aromatic 100 solvent, and 2 wt % of nonylphenol ethoxylate (4 moles) was added. The mixture was mixed until homogeneous.
Viscosity Measurements
The viscosity determinations were done on a Brookfield™ model DV-III viscometer equipped with a Thermosel™ system (Brookfield Engineering Labs. Inc., Stoughton, Mass.) and a temperature controller with a remote temperature detector probe. The Thermosel™ system consists of a heating chamber, a removable sample chamber, an SC4 spindle and an insulating cap. As the Thermosel™ system requires only 8 mL of sample, the sample temperature is readily controlled and the viscosity measurements are more accurate.
API Measurements
API measurement was carried out following the ASTM D 1298 test method using an appropriate hydrometer, a glass cylinder and a thermometer. Hydrometer scale readings were corrected to API gravity using the Petroleum Measurement Tables in Guide D 1250.
Results of viscosity and API measurements are displayed in Table 1, below, which displays viscosity at 120° F. (48.9° C.) in centipoise, percent viscosity reduction due to the additive (“% Red.”), API density at 60° F. (15.6° C.), and the percent increase in API density due to the additive (“% Inc.”), for various additives, with concentrations in ppm of the additive “as is,” i.e., not on an active ingredient basis. “Amide 1” is N,N-bis-(2-hydroxyethyl)oleamide; “Imidazoline 1” is 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-; “NP” is nonylphenol; “Amine 1” is an isomeric mixture of C10 to C15 tertiary alkyl primary amines (PRIMENE 81-R).
The results in Table 1 demonstrate that the formulation containing EDTA-Amine 1 complex, Amide 1 and Imidazoline 1 produces a much greater percent increase in API density than any other formulation tested. Such an increase is desirable to improve oil processing throughput. This formulation is an example of a composition comprising: (i) a chelating aminocarboxylic acid-C8-C22 amine complex; (ii) a C15-C21 bis(2-hydroxyethyl)amide; and (iii) a C15-C44 imidazoline compound, according to the present invention.
Asphaltene Dispersancy Test Methods:
This test requires a previously made dispersion of asphaltene in xylenes (Aromatic 150 solvent) or asphaltenic heavy crude diluted in xylenes (Aromatic 150 solvent) at a known concentration. A solution of an additive formulation (0.1 mL, the active ingredient was typically at 5-10 wt %, making the treat rate 500-1000 ppm) was taken in to a 15.0 mL graduated glass centrifuge tube, and hexanes added such that the total volume in the tube became 10.0 mL. To this mixture of additive and hexanes, asphaltenic stock solution (0.1 mL) was added. The test tube was then capped, shaken vigorously for about a minute or 40-60 times by hand and allowed to stand. The volume of any precipitated asphaltenes settled at the bottom of the tube was recorded at 10, 30, 60, 90 and 1440 (24 h) min intervals. When no additive was used, the volume of asphaltenes precipitated in the first 0.5-1 h was 0.4-0.5 mL (4-5%); in fact, it was important to initially adjust the concentration of the asphaltene stock in such a way that under these conditions of dilution with paraffinic solvents, a 4-5 vol % of asphaltenic precipitation occurred. When the additive was an effective dispersant of asphaltene, then no precipitate was formed up to 24 h (Rating=2; good). In some cases, no precipitation was observed in over 24 h to several days (Rating=2+; excellent). If the additive was not a dispersant, then an almost immediate precipitation of asphaltenes occurred (Rating=0; poor).
Results for asphaltene dispersancy rating (“ADR”) are displayed in Table 2, below. “Amide 1” is N,N-bis-(2-hydroxyethyl)oleamide; “Imidazoline 1” is 9-octadecenamide, N-{2-[2-(8-heptadecenyl)4,5-dihydro-1H-imidazol-1-yl]ethyl}-; “NP” is nonylphenol; “Amine 1” is an isomeric mixture of C10 to C15 tertiary alkyl primary amines (PRIMENE 81-R).
The results in Table 2 demonstrate that several formulations containing EDTA-Amine 1 complex, Amide 1 and Imidazoline 1 (see the last portion of Table 2, above) provide superior asphaltene dispersancy compared with any of the three ingredients at the same total level (see the first portion of Table 2). This formulation is an example of a composition comprising: (i) a chelating aminocarboxylic acid-C8-C22 amine complex; (ii) a C15-C21 bis(2-hydroxyethyl)amide; and (iii) a C15-C44 imidazoline compound, according to the present invention.
Compatibility Testing in Residual Fuel Oils
For this experiment, asphaltenic and paraffinic heavy fuels were blended at 1:0.1, 1:0.25, and 1:1 ratio (by volume) respectively following the test procedure listed below which is modified based on ASTM D 4740 (old test ASTM D 2781) test method:
This is a non-provisional application of prior pending U.S. Provisional Application Ser. No. 60/616,747 filed on Oct. 7, 2004.
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| Number | Date | Country | |
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| 20060079434 A1 | Apr 2006 | US |
| Number | Date | Country | |
|---|---|---|---|
| 60616747 | Oct 2004 | US |
