Process for preparing choline hydroxide from trimethylamine and ethylene oxide

Patent metadata

Field	Value
Publication number	US-9353045-B2
Application number	US-201313743616-A
Country	US
Kind code	B2
Filing date	Jan 17, 2013
Priority date	Jan 19, 2012
Publication date	May 31, 2016
Grant date	May 31, 2016

Abstract

Processes for preparing N,N,N-trimethylethanolammonium hydroxide (choline hydroxide) and the choline hydroxide produced are described. These processes minimize the production of byproduct mono-ethoxylated and di-ethyoxylated choline in the product choline hydroxide. The processes generally include feeding ethylene oxide, trimethylamine, and water into a first reactor to create a first reactor product under temperature controlled conditions. The product of the first reactor is fed into a second reactor to form a second reactor product under uncontrolled, adiabatic, conditions. Finally, any unreacted trimethylamine in the second reactor product is removed to form a final product comprising choline hydroxide. Additional reactors can be used for the ethylene oxide and trimethylamine reaction.

First claim

What is claimed is:

1. A process for preparing choline hydroxide comprising: feeding ethylene oxide, trimethylamine, and water into a first reactor to create a first reactor product, wherein the first reactor temperature is maintained between 5° C. and 35° C. and the molar ratio of ethylene oxide to trimethylamine fed to the first reactor is equal to or less than one; feeding the first reactor product into a second reactor to form a second reactor product, wherein the second reactor is insulated; and removing any unreacted trimethylamine from the second reactor product to form a final product comprising choline hydroxide.

2. The process of claim 1 , wherein the choline hydroxide final product comprises less than 10 weight percent mono-ethoxylated choline and/or di-ethyoxylated choline.

3. The process of claim 1 , wherein the trimethylamine and water are fed into the first reactor as a mixture.

4. The process of claim 1 , wherein the residence time in the second reactor is sufficient for any unreacted ethylene oxide present in the first reactor product to react.

5. The process of claim 1 , wherein adiabatic heating in the second reactor raises the temperature of the second reactor product to between 15° and 45° C.

6. The process of claim 1 , wherein the first reactor is a continuously stirred tank reactor.

7. The process of claim 1 , wherein the first reactor is a loop reactor with a high internal recycle ratio provided by a pump.

8. The process of claim 1 , wherein the first reactor is maintained at 20° C.

9. The process of claim 1 , wherein the unreacted trimethylamine is added to the trimethylamine fed into the first reactor.

10. A process for preparing choline hydroxide comprising: feeding trimethylamine, water, and ethylene oxide into a first reactor to create a first reactor product, wherein the first reactor temperature is maintained between 5° and 35° C.; feeding the first reactor product and a second amount of ethylene oxide into a second reactor to form a second reactor product, wherein the second reactor temperature is maintained between 5° and 35° C.; feeding the second reactor product into a third reactor to form a third reactor product, wherein the third reactor is insulated; and removing any unreacted trimethylamine from the third reactor product to form a final product comprising choline hydroxide.

11. The process of claim 10 , wherein the choline hydroxide final product comprises less than 10 weight percent mono-ethoxylated choline and/or di-ethyoxylated choline.

12. The process of claim 10 , wherein the trimethylamine and water are fed into the first reactor as a mixture.

13. The process of claim 10 , wherein the residence time in the third reactor is sufficient for any unreacted ethylene oxide present in the second reactor product to react.

14. The process of claim 10 , wherein adiabatic heating in the third reactor raises the temperature of the third reactor product to between 15° and 45° C.

15. The process of claim 10 , wherein the second amount of ethylene oxide fed into the second reactor is split from the ethylene oxide fed into the first reactor.

16. The process of claim 10 , wherein the ratio of amount of ethylene oxide fed into the first reactor to the second amount of ethylene oxide fed into the second reactor is between 50:50 and 99:1.

17. The process of claim 10 , wherein the ratio of amount of ethylene oxide fed into the first reactor to the second amount of ethylene oxide fed into the second reactor is 90:10.

18. The process of claim 10 , wherein the first reactor and second reactor are continuously stirred tank reactors.

19. The process of claim 10 , wherein the first reactor and second reactor are loop reactors with high internal recycle ratios provided by a pump.

20. The process of claim 10 , wherein the first reactor and second reactor are maintained at 20° C.

21. The process of claim 10 , wherein the unreacted trimethylamine is added to the trimethylamine fed into the first reactor.

22. The method of claim 1 , wherein the second reactor allows for uncontrolled adiabatic heating.

Assignees

• Dow Agrosciences Llc

Inventors

• Li Ruokang
• Dixit Ravindra S
• Patel Avani M
• Chen Xiaoyun
• Pell Randy J
• Pendergast Jr John G

Classifications

• C07C213/04 Primary

  by reaction of ammonia or amines with olefin oxides or halohydrins · CPC title

• C07C227/02

  Formation of carboxyl groups in compounds containing amino groups, e.g. by oxidation of amino alcohols · CPC title

• B01J19/00 Primary

  Chemical, physical or physico-chemical processes in general; Their relevant apparatus · CPC title

• A01N33/12 Primary

  Quaternary ammonium compounds · CPC title

• C07C215/40

  with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton · CPC title