Process for the preparation of polyalkenyl succinic anhydrides

• US 7,897,696 B2
• Filed: 02/01/2007
• Issued: 03/01/2011
• Est. Priority Date: 02/01/2007
• Status: Active Grant

• Current Assignee: Afton Chemical Corporation
• Original Assignee: Afton Chemical Corporation
• Inventors: Huang, Chente, Loper, John T.
• Primary Examiner(s): Rabago; Roberto
• Application Number:
  US11/670,256
• Publication Number:
  US 20080188385A1
• Time in Patent Office: 1,489 Days
• Field of Search: 508/232, 508/235, 525/333.7, 525/356, 525/357, 525/375, 525/379, 525/381, 525/382, 525/386, 528/486
• US Class Current: 525/333.7
• CPC Class Codes: C08F 110/10 Isobutene
• CPC Class Codes: C08F 8/22 by reaction with free halogens
• CPC Class Codes: C08F 8/46 Reaction with unsaturated dicarboxylic acids or anhydrides thereof, e.g. maleinisation
• CPC Class Codes: C10M 133/56 Amides; Imides
• CPC Class Codes: C10M 2215/28 Amides; Imides
• CPC Class Codes: C10N 2030/04 Detergent property or dispersant property

Abstract

A polyalkenyl succinic anhydride is prepared with low amounts of resinous or chlorinated byproducts in a two-step process whereby a polyalkene is first reacted with an unsaturated organic acid in a thermal ene reaction, followed with exposure to a gaseous halogen in presence of an additional amount of the unsaturated organic acidic reagent. The foregoing process produces a polyisobutenyl succinic anhydride having a high ratio of succinic anhydride functional groups to polyisobutenyl backbone groups. Such a polyisobutenyl succinic anhydride is particular suitable for the production of oil-soluble hydrocarbyl succinimides that have good dispersant properties when added to lubricating oil compositions.

Claims

1. A process for the preparation of a polyalkenyl succinic acid or anhydride comprising:

heating a mixture of a highly reactive polyalkene compound and an unsaturated acidic reagent to a thermal ene reaction temperature until about 50 weight percent of the polyalkene compound has reacted; and

subsequently, contacting the mixture with an additional amount of the unsaturated acidic reagent in the presence of a halogen gas to convert at least a portion of unreacted polyalkene compound in the mixture to the polyalkenyl succinic acid or anhydride;

wherein the highly reactive polyalkene compound comprises a polyalkene having greater than 50 mole % terminal double bond content.

2. The process of claim 1 wherein the highly reactive polyalkene compound comprises a polyalkene having a number average molecular weight ranging from about 800 to about 5000.

3. The process of claim 1 wherein the highly reactive polyalkene compound comprises a polyisobutene having a number average molecular weight ranging from about 1000 to about 3000.

4. The process of claim 1 wherein the unsaturated acidic reagent is selected from the group consisting of:

maleic anhydride, monophenyl maleic anhydride, monomethyl maleic anhydride, dimethyl maleic anhydride, N-phenyl maleimide, a substituted maleimide, an isomaleimide, fumaric acid, maleic acid, an alkyl hydrogen maleate, an alkyl hydrogen fumarate, a dialkyl fumarate, a dialkyl maleate, fumaronilic acid, maleanic acid, maleonitrile, and fumaronitrile.

5. The process of claim 1 wherein the step of heating further comprises adding a Lewis acid selected from the group consisting of aluminum chloride, boron trifluoride, and iron (III) chloride.

6. The process of claim 5 wherein the Lewis acid is present in a concentration ranging from about 20 ppm to about 200 ppm.

7. The process of claim 1 wherein the temperature ranges from about 150°

C. to about 250°

C.

8. The process of claim 1 wherein the mixture comprises unreacted polyalkene, unreacted unsaturated acidic reagent, and a polyalkenyl derivative of the unsaturated acidic reagent.

9. The process of claim 1 wherein the halogen gas is selected from the group consisting of fluorine, chlorine, bromine, and iodine.

10. The process of claim 1 wherein the halogen gas is present in a molar range from about 0.25 moles to about 1.5 moles per mole of highly reactive polyalkene compound.

11. A method for making a hydrocarbyl succinimide from the polyisobutenyl succinic anhydride of claim 1 comprising reacting the polyisobutenyl succinic anhydride with a polyamine having at least one basic nitrogen atom.

12. A method for making a dispersant lubricant additive comprising:

heating a mixture of a highly reactive polyalkene compound and an unsaturated acidic reagent to a thermal ene reaction temperature until about 50 weight percent of the polyalkene compound has reacted; and

subsequently, contacting the mixture with an additional amount of the unsaturated acidic reagent in the presence of a halogen gas to convert at least a portion of unreacted polyalkene compound in the mixture to the polyalkenyl succinic acid or anhydride;

reacting the polyisobutenyl succinic acid or anhydride with a polyamine having at least one basic nitrogen atom, forming a hydrocarbyl succinimide;

wherein the highly reactive polyalkene compound comprises a polyalkene having greater than 50 mole % terminal double bond content.

13. The method of claim 12 wherein the highly reactive polyalkene compound comprises a polyalkene having a number average molecular weight ranging from about 800 to about 5000.

14. The method of claim 12 wherein the highly reactive polyalkene compound comprises a polyisobutene having a number average molecular weight ranging from about 1000 to about 3000.

15. The method of claim 12 wherein the unsaturated acidic reagent is selected from the group consisting of:

maleic anhydride, monophenyl maleic anhydride, monomethyl maleic anhydride, dimethyl maleic anhydride, N-phenyl maleimide, a substituted maleimide, an isomaleimide, fumaric acid, maleic acid, an alkyl hydrogen maleate, an alkyl hydrogen fumarate, a dialkyl fumarate, a dialkyl maleate, fumaronilic acid, maleanic acid, maleonitrile, and fumaronitrile.

16. The method of claim 12 wherein the step of heating further comprises adding a Lewis acid selected from the group consisting of aluminum chloride, boron trifluoride, and iron (III) chloride.

17. The method of claim 16 wherein the Lewis acid is present in a concentration ranging from about 20 ppm to about 200 ppm.

18. The method of claim 12 wherein the temperature ranges from about 150°

C. to about 250°

C.

19. The method of claim 12 wherein the mixture comprises unreacted polyalkene, unreacted unsaturated acidic reagent, and a polyalkenyl derivative of the unsaturated acidic reagent.

20. The method of claim 12 wherein the halogen gas is selected from the group consisting of fluorine, chlorine, bromine, and iodine.

21. The method of claim 12 wherein the halogen gas is present in a molar range from about 0.25 moles to about 1.5 moles per mole of highly reactive polyalkene compound.