Patent Application
20080040968
Exact quantities of the starting materials were pre-determined and calculated based upon a mole ratio of 2:1:2 of 2-methyl-4-polyisobutyl phenol, dimethylaminepropylamine (DMAPA), and formaldehyde, respectfully. The 2-methyl-4-polyisobutyl phenol was added to a round bottom flask, followed by the addition of approximately 75% of the total calculated amount of Aromatic 100 solvent to be used during the process. The mixture was stirred under a nitrogen blanket. Once the mixture was homogeneous, the calculated amount of DMAPA was added. The temperature of the mixture was about 40 to 45° C. Formaldehyde was added, and the temperature of the mixture increased to about 45 to 50° C. The mixture was heated and distilled under nitrogen using a Dean Stark trap set to 150° C. During distillation, the temperature of 150° C. was maintained for about 2 to 2.5 hours. After distillation, sufficient Aromatic 100 solvent was added to the intermediate product to bring the final package composition to 25% solvent, taking into consideration the loss of water.
The above procedure theoretically resulted in the BIS product shown in the reaction below:
Using the intermediate BIS product of Example 1 as a starting material, 1,2-diaminocyloohexane (DACH) was added at a 1:1 molar ratio while stirring at room temperature under a nitrogen blanket. The temperature was set to 90° C. and held for 2 hours. The temperature was then set to 145° C. with increased nitrogen flow and held for 2.5 hours. The process theoretically resulted in the following reaction.
Gasoline fuel compositions employing the final product of Example 2 were subjected to engine tests whereby the substantial effectiveness of these compositions in reducing intake valve deposit weight was demonstrated. The above reaction products of Example 2 were compared with several other detergent compounds, including a first comparative compound formed by a mannich reaction of a 1:1:1 mole ratio of 2-methyl-4-polyisobutyl phenol, dibutylamine, and formaldehyde (“Mannich 1 additive”); a second comparative compound formed by a mannich reaction of a 1:1:1 mole ratio of 2-methyl-4-polyisobutyl phenol, DMAPA, and formaldehyde (“Mannich 2 additive”); and a third comparative compound that was a PIB Amine. The compounds of example 2 and the comparative compounds were each blended with a base fuel to form fuel compositions that are referred to in Table 1 and Table 2 by the additive compound employed (Example 2 Compounds, Mannich 1, Mannich 2, and PIB Amine).
A first comparative IVD Engine test of the compounds of Example 1, Mannich 1, Mannich 2 and the base fuel without additive was run using a Ford 2.3-liter engine operated on a test stand under standard operating conditions for determination of deposit formation on intake valves. The results are reported in Table 1 below.
A second comparative IVD Engine test of the compounds of Example 2; Mannich 1, Mannich 2, PIB Amine and the base fuel without additive was run using an IVD Bench Simulator (Model L-2), which can be used to test gasoline detergent IVD performance. The test simulates the IVD deposition in an engine. During the test, the fuel compositions with detergent additives were run through an injector. A separate air flow was run through an air flow line to the injector. The air flow and gasoline flow were mixed at the tip of the injector, and the mixture was directed against a heated metal plate. Plate temperatures were controlled at around 174° C. Gasoline evaporated on the surface of the hot plate, leaving a deposit and stain behind.
At the end of the IVD Bench Simulator test, the deposit on the metal plate was weighted. The results are reported in Table 2 below.
It is clear, upon examination of the above Tables 1 and 2, that the reaction products of Example 2 exhibit improved performance over the base fuel without additive, and comparable performance to the additives of Comparative Examples 1 and 2, as demonstrated by the reduced amount of deposits in the Ford 2.3L Test. In addition, the reaction product of Example 2 exhibits improved performance over the base fuel without additive and the additives of Comparative Examples 1 and 2, as demonstrated by the reduced amount of deposits in the IVD Bench Test From China.
For the purposes of this specification and appended claims, unless otherwise indicated, all numbers expressing quantities, percentages or proportions, and other numerical values used in the specification and claims, are to be understood as being modified in all instances by the term “about.” Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following specification and attached claims are approximations that can vary depending upon the desired properties sought to be obtained by the present disclosure. At the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.
It is noted that, as used in this specification and the appended claims, the singular forms “a,” “an,” and “the,” include plural referents unless expressly and unequivocally limited to one referent. Thus, for example, reference to “an acid” includes two or more different acids. As used herein, the term “include” and its grammatical variants are intended to be non-limiting, such that recitation of items in a list is not to the exclusion of other like items that can be substituted or added to the listed items.
While particular embodiments have been described, alternatives, modifications, variations, improvements, and substantial equivalents that are or can be presently unforeseen can arise to applicants or others skilled in the art. Accordingly, the appended claims as filed and as they can be amended are intended to embrace all such alternatives, modifications variations, improvements, and substantial equivalents.
