Seal swell agent and process therefor

• US 7,485,734 B2
• Filed: 01/28/2005
• Issued: 02/03/2009
• Est. Priority Date: 01/28/2005
• Status: Active Grant

• Current Assignee: Afton Chemical Corporation
• Original Assignee: Afton Chemical Corporation
• Inventors: Ozbalik, Nubar, Kadkhodayan, Abbas
• Primary Examiner(s): Dentz; Bernard
• Assistant Examiner(s): Gallis; David E
• Application Number:
  US11/046,073
• Publication Number:
  US 20060173217A1
• Time in Patent Office: 1,467 Days
• Field of Search: 568/32, 252/72, 252/78.1, 549/78, 549/67, 508/303
• US Class Current: 549/67
• CPC Class Codes: C07D 333/48 by oxygen atoms
• CPC Class Codes: C10M 135/34 the ring containing sulfur and carbon only
• CPC Class Codes: C10M 2219/102 containing sulfur and carbon only in the ring
• CPC Class Codes: C10N 2030/36 Seal compatibility, e.g. with rubber
• CPC Class Codes: C10N 2040/042 for automatic transmissions

Abstract

A method of making 3-alkoxytetraalkylene sulfone. The method includes mixing an alcohol and a catalyst to form a first mixture. Alkadiene sulfone is reacted with the first mixture to form a reaction product. The reaction product is contacted with water at conditions sufficient to provide an organic phase and an inorganic phase. Subsequent to contacting the reaction product with water, the organic phase and inorganic phase are separated from one another.

Claims

1. A method of making 3-alkoxytetraalkylene sulfone comprising:

mixing an alcohol and a catalyst to form a first mixture;

reacting alkadiene sulfone with the first mixture to form a reaction product;

contacting the reaction product with water and heating the reaction product and water to a temperature sufficient to provide an organic phase and an inorganic phase; and

separating the organic phase and inorganic phase from one another,

wherein the organic phase contains less than about 2000 ppm water.

2. The method of claim 1, wherein the organic phase contains less than about 0.75 percent weight of unreacted alkadiene sulfone.

3. The method of claim 1, wherein the organic phase contains less than about 1 ppm SO₂.

4. The method of claim 1, wherein the organic phase contains less than about 12 percent weight of sulfur.

5. The method of claim 1, wherein the contacting step comprises:

contacting the reaction product with water at a temperature ranging from about 80°

C. to about 85°

C. to provide the organic phase and the inorganic phase.

6. The method of claim 1, wherein the contacting step comprises:

contacting the reaction product with water at a temperature ranging from about 80°

C. to about 85°

C. to provide a first organic phase and a first inorganic phase;

separating the first inorganic phase and first organic phase from one another;

contacting the first organic phase with water at a temperature ranging from about 80°

C. to about 85°

C. to provide a second organic phase and a second inorganic phase; and

separating the second organic phase and second inorganic phase from one another to provide a purified 3-alkoxytetraalkylene sulfone product.

7. The method of claim 6, wherein the sulfone product has a potassium content of form about 0 to about 2 ppm.

8. The method of claim 1, wherein the alkadiene sulfone comprises butadiene sulfone.

9. The method of claim 1, wherein the alkadiene sulfone comprises sulfolene.

10. The method of claim 9, wherein the 3-alkoxytetraalkylene sulfone comprises 3-alkoxytetramethylene sulfone.

11. The method of claim 10, wherein the alkoxy groups of the 3-alkoxytetramethylene sulfone contain from about 4 to about 30 carbon atoms.

12. The method of claim 1, wherein the alcohol contains from about 4 to about 30 carbon atoms.

13. The method of claim 12, wherein the alcohol contains from about 8 to about 16 carbon atoms.

14. The method of claim 1, wherein the alcohol is selected from the group consisting of butyl, amyl, hexyl, octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, triacontanyl, butenyl, dodecenyl, phenyl, naphthyl, tolyl, dodecylphenyl, tetrapropene-alkylated phenyl, phenylethyl, cyclohexyl, methylcyclohexyl alcohols and isomers thereof.

15. The method of claim 1, wherein the alcohol is iso-decyl alcohol.

16. The method of claim 1, wherein the ratio of alcohol to sulfone ranges from about 0.5:

1 to about 2;

1 on a mole basis.

17. The method of claim 16, wherein the ratio of alcohol to sulfone ranges from about 0.01:

1 to about 0.1;

1 on a mole basis.

18. In a process of making 3-alkoxytetraalkylene sulfone wherein an alcohol and alkadiene sulfone are reacted in the presence of a catalyst to form a reaction product, an improvement comprising:

adding water to the reaction product to form a first mixture;

heating the first mixture to a sufficient temperature to form a first organic phase and a first inorganic phase;

separating the first organic phase and first inorganic phase from one another to provide a 3-alkoxytetraalkylene sulfone product having a reduced impurity level.

19. The improvement of claim 18, wherein the heating step comprises:

heating the first mixture to a temperature ranging from about 80°

C. to about 85°

C. to form the first organic phase and the first inorganic phase.

20. The improvement of claim 18, further comprising adding water to the first organic phase to form a second mixture;

heating the second mixture to a sufficient temperature to provide a second organic phase and a second inorganic phase; and

separating the second inorganic phase and second organic phase from one another, wherein the impurity level of catalyst in the organic phase ranges from about 0 to about 5 ppm.

21. The improvement of claim 20, wherein the heating step comprises:

heating the second mixture to a temperature ranging from about 80°

C. to about 85°

C. to provide the second organic phase and the second inorganic phase.

22. The improvement of claim 18, wherein the second organic phase contains less than about 2000 ppm water.

23. The improvement of claim 18, wherein the second organic phase contains less than about 0.75 percent weight of unreacted alkadiene sulfone.

24. The improvement of claim 18, wherein the second organic phase contains less than about 1 ppm SO₂.

25. The improvement of claim 18, wherein the second organic phase contains less than about 12 percent weight of sulfur.

26. The improvement of claim 18, further comprising:

adding water to the 3-alkoxytetraalkylene sulfone product to form a second mixture;

heating the second mixture to a sufficient temperature to provide a second organic phase and a second inorganic phase; and

separating the second organic phase and second inorganic phase from one another.

27. The improvement of claim 26, wherein the heating step comprises:

heating the second mixture to a temperature ranging from about 80°

C. to about 85°

C. to provide the second organic phase and the second inorganic phase.

28. The improvement of claim 18, wherein the alkadiene sulfone comprises butadiene sulfone.

29. The improvement of claim 18, wherein the alkadiene sulfone comprises sulfolene.

30. The improvement of claim 29, wherein the 3-alkoxytetraalkylene sulfone comprises 3-alkoxytetramethylene sulfone.

31. The improvement of claim 30, wherein the alkoxy groups of the 3-alkoxytetramethylene sulfone contain from about 4 to about 30 carbon atoms.

32. The improvement of claim 18, wherein the alcohol contains from about 4 to about 30 carbon atoms.

33. The improvement of claim 32, wherein the alcohol contains from about 8 to about 16 carbon atoms.

34. The improvement of claim 18, wherein the alcohol is selected from the group consisting of butyl, amyl, hexyl, octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, triacontanyl, butenyl, dodecenyl, phenyl, naphthyl, tolyl, dodecylphenyl, tetrapropene-alkylated phenyl, phenylethyl, cyclohexyl, methylcyclohexyl alcohols and isomers thereof.

35. The improvement of claim 18, wherein the alcohol is iso-decyl alcohol.

36. The improvement of claim 18, wherein the ratio of alcohol to sulfone ranges from about 0.5:

1 to about 2;

1 on a mole basis.

37. The improvement of claim 36, wherein the ratio of alcohol to sulfone ranges from about 0.01:

1 to about 0.1;

1 on a mole basis.

38. A lubricant composition comprising a base oil and the sulfone product of claim 18 wherein the sulfone product, as made, contains less than 2000 ppm water.

39. The lubricant composition of claim 38, wherein the sulfone product is present in the composition in an amount ranging from about 0.1 to about 10.0 percent by weight.

40. A vehicle transmission fluid comprising the sulfone product of claim 18 wherein the sulfone product, as made, contains less than 2000 ppm water.

41. An additive concentrate for a transmission fluid, the additive concentrate comprising from about 0.1 to about 10.0 percent by weight of the sulfone product of claim 18.

42. A lubricant additive concentrate comprising a seal swelling agent of the formula:

43. The additive concentrate of claim 42, wherein the seal swelling agent contains less than about 0.75 percent weight of unreacted alkadiene sulfone.

44. The additive concentrate of claim 42, wherein the seal swelling agent contains less than about 1 ppm SO₂.

45. The additive concentrate of claim 42, wherein the seal swelling agent contains less than about 12 percent weight of sulfur.