Claims
- 1. A method of preparing a quaternary ammonium methocarbonate having the formula
- 2. The method of claim 1, wherein R1 and R2 are independently C1-C20 alkyl and R3 is a C8-C20 alkyl.
- 3. The method of claim 1, wherein R1 and R2 are independently C1-C16 alkyl and R3 is a C8-C16 alkyl.
- 4. The method of claim 3, wherein R1 is methyl.
- 5. The method of claim 1, wherein R2 is C1-C20 alkyl.
- 6. The method of claim 5, wherein R2 is methyl.
- 7. The method of claim 5, wherein R2 is C8-C12 alkyl.
- 8. The method of claim 7, wherein R2 is C10 alkyl.
- 9. The method of claim 1, wherein R3 is C8-C20 alkyl.
- 10. The method of claim 9, wherein R3 is C8-C12 alkyl.
- 11. The method of claim 10, wherein R3 is C10 alkyl.
- 12. The method of claim 1, wherein R1 is methyl and R2 and R3 are independently C8-C12 alkyl.
- 13. The method of claim 12, wherein R2 and R3 are C10 alkyl.
- 14. The method of claim 1, wherein R1 and R2 are methyl and R3 is C8-C20 alkyl.
- 15. The method of claim 1, wherein the amine is selected from the group consisting of didecylmethylamine, dodecyldimethylamine, dioctylmethylamine, octadecyldimethylamine, dioctadecylmethylamine, trioctylamine, and any combination of any of the foregoing.
- 16. The method of claim 1, wherein R4 is hydrogen or methyl.
- 17. The method of claim 16, wherein the cyclic carbonate is ethylene carbonate.
- 18. The method of claim 16, wherein the cyclic carbonate is propylene carbonate.
- 19. The method of claim 1, wherein R5, R6, R7, and R8 are independently hydrogen or C1-C4 alkyl.
- 20. The method of claim 19, wherein R5, R6, R7, and R8 are independently hydrogen or methyl.
- 21. The method of claim 1, wherein R5 is methyl and R6, R7, and R8 are hydrogen.
- 22. The method of claim 1, wherein m ranges from 1 to 100.
- 23. The method of claim 1, wherein the molar ratio of amine to component (b) ranges from about 1:1 to about 1:10.
- 24. The method of claim 23, wherein the molar ratio of amine to component (b) ranges from about 1:2 to about 1:3.
- 25. The method of claim 1, wherein the molar ratio of amine to methanol ranges from about 1:2 to about 1:20.
- 26. The method of claim 1, wherein the reaction step is performed at from about 120 to about 160° C.
- 27. The method of claim 26, wherein the reaction step is performed at from about 120 to about 150° C.
- 28. The method of claim 27, wherein the reaction step is performed at from about 120 to about 140° C.
- 29. The method of claim 1, further comprising the step of recovering the dimethyl carbonate.
- 30. The method of claim 1, wherein the reaction step comprises reacting
(a) the amine; (b) (i) the cyclic carbonate,
(ii) the aliphatic polyester, or (iii) a mixture thereof; (c) methanol; and (d) dimethylcarbonate.
- 31. The method of claim 30, wherein the molar ratio of amine to dimethylcarbonate ranges from about 2:1 to about 1:3.
- 32. A method of preparing didecyldimethyl ammonium methocarbonate comprising reacting
(a) didecylmethylamine; (b) a cyclic carbonate selected from the group consisting of ethylene carbonate, propylene carbonate, and mixtures thereof; and (c) methanol to form didecyldimethyl ammonium methocarbonate.
- 33. The method of claim 32, wherein the reaction step comprises reacting
(a) didecylmethylamine; (b) a cyclic carbonate selected from the group consisting of ethylene carbonate, propylene carbonate, and mixtures thereof; (c) methanol; and (d) dimethylcarbonate.
- 34. The method of claim 32, wherein the cyclic carbonate is propylene carbonate.
- 35. A method of preparing a quaternary ammonium bicarbonate having the formula
- 36. A method of preparing didecyldimethyl ammonium bicarbonate comprising
(a) reacting
(i) didecylmethylamine, (ii) a cyclic carbonate selected from the group consisting of ethylene carbonate, propylene carbonate, and mixtures thereof, and (iii) methanol to form didecyldimethyl ammonium methocarbonate; and (b) converting the didecyldimethyl ammonium methocarbonate to didecyldimethyl ammonium bicarbonate.
- 37. The method of claim 36, wherein step (a) comprises reacting
(i) didecylmethylamine, (ii) a cyclic carbonate selected from the group consisting of ethylene carbonate, propylene carbonate, and mixtures thereof, (iii) methanol, and (iv) dimethylcarbonate to form didecyldimethyl ammonium methocarbonate.
- 38. A method of preparing a mixture of quaternary ammonium bicarbonate and quaternary ammonium carbonate wherein the quaternary ammonium cation has the formula N+(CH3)R1R2R3 and R1, R2, and R3 are independently C1-C30 alkyl, the method comprising
(a) preparing a quaternary ammonium methocarbonate by the method of claim 1; and (b) converting the quaternary ammonium methocarbonate to a mixture of quaternary ammonium bicarbonate and quaternary ammonium carbonate.
- 39. A method of preparing a quaternary ammonium alkylcarbonate having the formula
- 40. The method of claim 39, wherein R1 is methyl and R2 and R3 are independently C8-C12 alkyl.
- 41. The method of claim 39, wherein the amine is selected from the group consisting of didecylmethylamine, dodecyldimethylamine, dioctylmethylamine, octadecyldimethylamine, dioctadecylmethylamine, trioctylamine, and any combination of any of the foregoing.
- 42. The method of claim 39, wherein the molar ratio of amine to ester ranges from about 1:1 to about 1:10.
- 43. The method of claim 42, wherein the molar ratio of amine to ester ranges from about 1:2 to about 1:3.
- 44. The method of claim 39, wherein the molar ratio of amine to methanol ranges from about 1:2 to about 1:20.
- 45. The method of claim 39, wherein the reaction step is performed at from about 120 to about 160° C.
- 46. The method of claim 45, wherein the reaction step is performed at from about 120 to about 150° C.
- 47. The method of claim 46, wherein the reaction step is performed at from about 120 to about 140° C.
- 48. The method of claim 39, further comprising the step of recovering alkanol having the formula R9OH.
- 49. The method of claim 39, wherein the reaction step comprises reacting
(a) the amine; (b) the ester; (c) methanol; and (d) alkyl methyl carbonate having the formula CH3OC(O)OR9.
- 50. A method of preparing a quaternary ammonium bicarbonate having the formula
- 51. A method of preparing a quaternary ammonium methocarbonate having the formula
- 52. The method of claim 51, wherein the carbonate ester has the formula
Parent Case Info
[0001] This application claims the benefit of U.S. Provisional Application No. 60/303,971, filed Jul. 9, 2001, which is hereby incorporated by reference.
Provisional Applications (1)
|
Number |
Date |
Country |
|
60303971 |
Jul 2001 |
US |
Divisions (1)
|
Number |
Date |
Country |
Parent |
10188692 |
Jul 2002 |
US |
Child |
10776368 |
Feb 2004 |
US |