Processes for converting glycerol to glycerol ethers

• US 20070238905A1
• Filed: 03/30/2007
• Published: 10/11/2007
• Est. Priority Date: 04/05/2006
• Status: Abandoned Application

• Current Assignee: The Procter & Gamble Company
• Original Assignee: The Procter & Gamble Company
• Inventors: Arredondo, Victor Manuel, Corrigan, Patrick Joseph, Back, Deborah Jean, Cearley, Angella Christine, Kreuzer, David Patrick
• Application Number:
  US11/731,616
• Publication Number:
  US 20070238905A1
• Time in Patent Office: Days
• US Class Current: 568/672
• CPC Class Codes: C07C 41/09 by dehydration of compounds containing hydroxy groups
• CPC Class Codes: C07C 43/13 containing hydroxy or O-metal groups C07C43/11 takes precedence
• CPC Class Codes: C07C 43/135 having more than one ether bond
• CPC Class Codes: Y02P 20/10 Process efficiency

Abstract

Processes for converting glycerol to alkyl glycerol ethers that involve providing glycerol, alkyl alcohol and an etherification catalyst, providing an etherification reactor and, adding the glycerol, alkyl alcohol and etherification catalyst to the etherification reactor and reacting the glycerol, alkyl alcohol and etherification catalyst in the etherification reactor to obtain a reaction product comprising alkyl glycerol ethers.

Claims

1. A process for converting glycerol to alkyl glycerol ethers comprising:

a) providing glycerol, alkyl alcohol and an etherification catalyst;

b) providing an etherification reactor;

c) adding the glycerol, alkyl alcohol and etherification catalyst to the etherification reactor; and

d) reacting the glycerol, alkyl alcohol and etherification catalyst in the etherification reactor to obtain a reaction product comprising alkyl glycerol ethers.

2. The process of claim 1 wherein the glycerol and alkyl alcohol are added to the etherification reactor in molar ratio of glycerol to alkyl alcohol of from about 1:

30 to about 1;

0.5.

3. The process of claim 1 wherein reacting the glycerol, alkyl alcohol and etherification catalyst occurs at a temperature of from about 70°

C. to about 250°

C.

4. The process of claim 1 wherein the reaction product comprises a liquid reaction product comprising alkyl glycerol ethers and a vapor reaction product comprising volatile components.

5. The process of claim 4 comprising separating the liquid reaction product comprising alkyl glycerol ethers from the vapor reaction product.

6. The process of claim 1 further comprising:

providing an inert gas; and

adding the glycerol, alkyl alcohol and etherification catalyst to the etherification reactor and reacting the glycerol, alkyl alcohol and etherification catalyst in the etherification reactor in the presence of the inert gas to obtain a liquid reaction product comprising alkyl glycerol ethers and a vapor reaction product comprising volatile components and the inert gas.

7. The process of claim 6 further comprising removing the volatile components from the inert gas.

8. The process of claim 7 further comprising recycling the inert gas.

9. The process of claim 1 wherein the etherification reactor is a fixed bed column reactor, a continuous stir tank reactor, a reactive distillation reactor or a batch reactor.

10. The process of claim 6 wherein the inert gas comprises nitrogen.

11. The process of claim 1 wherein the etherification catalyst is selected from the group consisting of Bronsted acids, Lewis acids and combinations thereof.

12. The process of claim 1 further comprising treating the glycerol to obtain a treated glycerol and adding the treated glycerol, alkyl alcohol and etherification catalyst to the etherification reactor.

13. The process of claim 12 wherein treating the glycerol comprises a method selected from the group consisting of neutralization, precipitation, filtration, evaporation, steam stripping, ion-exchange, adsorption and combinations thereof.

14. The process of claim 2 wherein the molar ratio of glycerol to alkyl alcohol of from about 1:

5 to about 1;

1.

15. A process for converting glycerol to alkyl glycerol ethers comprising:

a) providing crude glycerol, alkyl alcohol and an etherification catalyst;

b) providing an inert gas;

c) providing an etherification reactor;

d) providing a vaporizer;

e) adding the crude glycerol and the inert gas to the vaporizer to obtain a glycerol vapor;

f) transferring the glycerol vapor and inert gas to the etherification reactor; and

g) adding the alkyl alcohol and etherification catalyst to the glycerol vapor in the etherification reactor in the presence of the inert gas; and

h) reacting the glycerol vapor, alkyl alcohol and etherification catalyst in the etherification reactor to obtain a vapor reaction product comprising glycerol alkyl ethers.

16. The process of claim 15 wherein the reacting the glycerol vapor, alkyl alcohol and etherification catalyst occurs at a temperature of from about 70°

C. to about 250°

C.

17. The process of claim 15 wherein the glycerol and alkyl alcohol are added to the etherification reactor in molar ratio of glycerol to alkyl alcohol of from about 1:

30 to about 1;

0.5.

18. The process of claim 15 further comprising recycling unreacted glycerol to the evaporator.

19. The process of claim 15 wherein the vaporizer is a flash tank evaporator or a wiped film evaporator.

20. A process for converting glycerol to alkyl glycerol ethers comprising:

a) providing crude glycerol, alkyl alcohol and an etherification catalyst;

b) providing an etherification reactor;

c) treating the crude glycerol to obtain a treated glycerol;

d) adding the treated glycerol, alkyl alcohol and etherification catalyst to the etherification reactor;

e) reacting the treated glycerol, alkyl alcohol and etherification catalyst in the etherification reactor to obtain a reaction product comprising at least one of mono-alkyl glycerol ethers, di-alkyl glycerol ethers, unreacted alkyl alcohol, unreacted glycerol, diglycerols, di-alkyl ethers, alkenes, water etherification catalyst and combinations thereof;

f) separating mono-alkyl glycerol ether from the di-alkyl glycerol ether, unreacted alkyl alcohol, unreacted glycerol, diglycerols, di-alkyl ethers, alkenes, water, and etherification catalyst; and

collecting the mono-alkyl glycerol ether.