PRODUCTS PRODUCED BY POST-TREATING OIL-SOLUBLE ESTERS OF MONO- OR POLYCARBOXYLIC ACIDS AND POLYHYDRIC ALCOHOLS WITH EPOXIDES
First Claim
1. AN OIL-SOLUBLE REACTION PRODUCT PRODUCED BY A PROCESS COMPRISING CONTACTING AT A TEMPERATURE OF FROM ABOUT 25*C. UP TO ABOUT THE DECOMPOSITION TEMPERATURE (A) AT LEAST ONE OIL-SOLUBLE ESTER OF A MONO- OR POLYCARBOXYLIC ACID AND A POLYHYDRIC ALCOHOL HAVING AT LEAST THREE HYDROXYL GROUPS WHEREIN THE CARBOXYLIC ACID MOIETY OF THE ESTER IS CHARACTERIZED BY A SUBSTANTIALLY SATURATED, ALIPHATIC HYDROCARBON RADICAL, WHICH IS SUBSTANTIALLY FREE OF OIL-SOLUBILIZING PENDENT GROUPS AND HAS AT LEAST ABOUT 50 ALIPHATIC CARBON ATOMS EXCLUSIVE OF THE CARBOXYL CARBON ATOMS, AND THE ALCOHOL MOIETY CONTAINS UP TO ABOUT 40 ALIPHATIC CARBON ATOMS;
- WITH (B) AT LEAST ONE ORGANIC EPOXIDE HAVING UP TO ABOUT 40 CARBON ATOMS AND CORRESPONDING TO THE FORMULA
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Abstract
A process for post-treating oil-soluble esters of mono- or polycarboxylic acids and polyhydric alcohols with organic epoxides. The acyl moiety of the esters is derived from mono- or polycarboxylic acids containing at least about fifty aliphatic carbon atoms exlusive of the carboxyl carbon atoms. The products are useful as lubricant and fuel additives. A typical example of the process would be the post-treatment of a diester of polyisobutenyl1-substituted succinic acid and sorbitol with propylene oxide.
68 Citations
19 Claims
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1. AN OIL-SOLUBLE REACTION PRODUCT PRODUCED BY A PROCESS COMPRISING CONTACTING AT A TEMPERATURE OF FROM ABOUT 25*C. UP TO ABOUT THE DECOMPOSITION TEMPERATURE (A) AT LEAST ONE OIL-SOLUBLE ESTER OF A MONO- OR POLYCARBOXYLIC ACID AND A POLYHYDRIC ALCOHOL HAVING AT LEAST THREE HYDROXYL GROUPS WHEREIN THE CARBOXYLIC ACID MOIETY OF THE ESTER IS CHARACTERIZED BY A SUBSTANTIALLY SATURATED, ALIPHATIC HYDROCARBON RADICAL, WHICH IS SUBSTANTIALLY FREE OF OIL-SOLUBILIZING PENDENT GROUPS AND HAS AT LEAST ABOUT 50 ALIPHATIC CARBON ATOMS EXCLUSIVE OF THE CARBOXYL CARBON ATOMS, AND THE ALCOHOL MOIETY CONTAINS UP TO ABOUT 40 ALIPHATIC CARBON ATOMS;
- WITH (B) AT LEAST ONE ORGANIC EPOXIDE HAVING UP TO ABOUT 40 CARBON ATOMS AND CORRESPONDING TO THE FORMULA
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2. An oil-soluble reaction product according to claim 1 where (A) and (B) are contacted at a temperature within the range of about 50*-250*C. and (B) is at least one organic epoxide wherein each R is independently hydrogen, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, aryl, haloaryl where the haloalkyl, halocycloalkyl, and haloaryl groups have no more than one halogen radical for every 3 carbon atoms.
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3. An oil-soluble reaction product according to claim 2 where (B) is at least one aliphatic epoxide containing 2 to 8 carbon atoms.
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4. An oil-soluble reaction product according to claim 3 where (B) is at least one terminal aliphatic epoxide.
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5. An oil-soluble reaction product according to claim 4 where (A) is at least one ester of a monocarboxylic acid and (A) and (B) are contacted at a temperature of about 70*-200*C.
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6. An oil-soluble reaction product according to claim 5 where (A) is an ester of a polyhydric aliphatic alcohol of up to 10 carbon atoms, and characterized by the presence of at least three hydroxyl groups.
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7. An oil-soluble reaction product according to claim 6 wherein the polyhydric aliphatic alcohol is a polyhydric alkanol of up to 6 carbon atoms, the aliphatic epoxide is ethylene oxide or propylene oxide, and said ratio of equivalents is about 1:
- 0.1 to about 1;
2.
- 0.1 to about 1;
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8. An oil-soluble reaction product according to claim 7 wherein the polyhydric aliphatic alcohol is selected from the class comprising glycerol, erythritol, pentaerythritol, manniTol, and sorbitol.
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9. An oil-soluble reaction product according to claim 4 where (A) is at least one ester of a dicarboxylic acid and (A) and (B) are contacted at a temperature of about 70*-200*C.
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10. An oil-soluble reaction product according to claim 9 where (A) is an ester of a hydrocarbon-substituted or chlorinated hydrocarbon-substituted succinic acid wherein the substituent is substantially saturated and contains at least about fifty aliphatic carbon atoms.
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11. An oil-soluble reaction product according to claim 10 where (A) is a diester of a polyolefin-substituted succinic acid wherein the polyolefin substituent has a molecular weight of about 700 to about 5000 and not more than about 5% of the carbon-to-carbon covalent linkages in this substituent are unsaturated linkages.
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12. An oil-soluble reaction product according to claim 11 where (A) is a diester of a polyhydric aliphatic alcohol up to 10 carbon atoms which alcohol is characterized by the presence of at least three hydroxyl groups.
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13. An oil-soluble reaction product according to claim 12 wherein the polyhydric aliphatic alcohol is a polyhydric alkanol of up to 6 carbon atoms, the aliphatic epoxide is ethylene oxide or propylene oxide, and said ratio of equivalents is about 1:
- 0.1 to about 1;
2.
- 0.1 to about 1;
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14. An oil-soluble reaction product according to claim 13 where (A) is a diester of polyisobutene-substituted succinic acid with a polyhydric alkanol selected from the class consisting of glycerol, erythritol, pentaerythritol, mannitol, and sorbitol.
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15. An oil-soluble reaction product according to claim 4 produced by contacting (A) with (B) where (A) is at least one ester of a mono- or polycarboxylic acid where the acyl moiety of said mono- or polycarboxylic acid corresponds to the acyl moiety derived from the reaction at a temperature within the range of about 100*-300*C. of (1) an unsaturated carboxylic acid of the formula Ro-(COOH)n or the corresponding acyl halides or anhydrides where Ro is characterized by the presence of at least one ethylenically unsaturated carbon-to-carbon covalent bond in an Alpha , Beta -position with respect to at least one carboxyl function and n is an integer of one to six with (2) an ethylenically unsaturated hydrocarbon containing at least about fifty aliphatic carbon atoms or a chlorinated hydrocarbon containing at least about 50 aliphatic carbon atoms, wherein (A) and (B) are contacted at a temperature of about 70*-200*C.
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16. An oil-soluble reaction product according to claim 15 where the acyl moiety is derived from the reaction of (1) an unsaturated carboxylic acid of the formula Ro-(COOH)n or its corresponding acyl halides or anhydrides where Ro is characterized by the presence of at least one ethylenically unsaturated carbon-to-carbon covalent bond in an Alpha , Beta -position with respect to at least one carboxyl function, n is one or two and the total number of carbon atoms in Ro-(COOH)n does not exceed 10 with (2) polymerized 1-monoolefins or chlorinated polymerized 1-monoolefins.
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17. An oil-soluble reaction product according to claim 16 where (A) is at least one ester of a polyhydric aliphatic alcohol of up to 10 carbon atoms characterized by the presence of at least three hydroxyl groups.
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18. An oil-soluble reaction product according to claim 17 containing about 0.5% to about 10% by weight of the composition produced by contacting (A) with (B) wherein the total number of carbon atoms in Ro-(COOH)n does not exceed six and where (2) is polyisobutylene or chlorinated polyisobutylene.
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19. An oil-soluble reaction reaction product according to claim 18 where (A) is at least one ester of a polyhydric alkanol of up to 6 carbon atoms and (B) is selected from the group consiSting of ethylene oxide or propylene oxide, the ratio of equivalents of (A) to (B) being about 1:
- 0.1 to about 1;
2.
- 0.1 to about 1;
Specification