Process for making polyglycerol ethers of fatty alcohols

Patent metadata

Field	Value
Publication number	US-9035104-B2
Application number	US-201113374192-A
Country	US
Kind code	B2
Filing date	Dec 15, 2011
Priority date	Dec 16, 2010
Publication date	May 19, 2015
Grant date	May 19, 2015

Abstract

Disclosed are processes relating to the production of polyglycerol ethers of fatty alcohols, in particular, one step process using fatty alcohol and glycerine to synthesize polyglycerides of fatty alcohols will provide a 100% renewable surfactant that is cost effective efficient and CMR free. The synthetic methods mentioned in prior art uses hazardous chemicals as glycidyl ethers, epichlorohydrin that are listed as CMR and known carcinogens and hazardous to handle.

First claim

What is claimed is:

1. A process for preparing a polyglycerol ether of fatty alcohol comprising the steps of:
a) contacting a fatty alcohol with glycerine, in the presence of an:
(i) acid catalyst,
(ii) a solvent, and
(iii) a short chain alcohol, emulsifier or a combination thereof.

2. The process of claim 1 further comprising the step of b) distilling off the short chain alcohol, emulsifier or combination thereof at reduced pressure.

3. The process of claim 2 wherein step b) is performed under an inert gas.

4. The process of claim 1 wherein the fatty alcohol has from 8 to 22 carbon atoms.

5. The process of claim 1 wherein the fatty alcohol has from 8 to 40 carbon atoms.

6. The process of claim 1 wherein the short chain alcohol has from 1 to 5 carbon atoms.

7. The process of claim 1 wherein the short chain alcohol has from 1 to 7 carbon atoms.

8. The process of claim 1 wherein the solvent is a dibasic ester, water or a combination thereof.

9. A process for preparing a polyglycerol monoether of formula:
R 1 O—(C 3 H 6 O 2 ) n —H   (1)

wherein R 1 is a C 8 -C 22 alkyl group or hydrogen and —n— is an integer greater than 1, the process comprising the steps of:
a) contacting a C 8 -C 22 fatty alcohol with glycerine, in the presence of an:
(i) acid catalyst,
(ii) a solvent, and
(iii) a short chain alcohol, emulsifier or a combination thereof;

b) distilling off the short chain alcohol, emulsifier or combination thereof at reduced pressure.

10. The process of claim 9 wherein step b) is performed under an inert gas.

11. The process of claim 9 wherein the fatty alcohol has from 8 to 22 carbon atoms.

12. The process of claim 9 wherein the short chain alcohol has from 1 to 5 carbon atoms.

13. The process of claim 9 wherein the solvent is a dibasic ester, water or a combination thereof.

14. A process for preparing a polyglycerol polyether of formula:
R 1 O—(C 3 H 5 O 2 R 2 )n—H   (2)

wherein R 1 and R 2 are individually a C 8 -C 22 alkyl group or hydrogen and —n— is an integer greater than 1, the process comprising the steps of:
a) contacting a C 8 -C 22 fatty alcohol with glycerine, in the presence of an:
(i) acid catalyst,
(ii) a solvent, and
(iii) a short chain alcohol or emulsifier or both;

b) distilling off the short chain alcohol, emulsifier or combination thereof at reduced pressure.

15. The process of claim 14 wherein step b) is performed under an inert gas.

16. The process of claim 14 wherein the fatty alcohol has from 8 to 22 carbon atoms.

17. The process of claim 14 wherein the short chain alcohol has from 1 to 5 carbon atoms.

18. The process of claim 14 wherein the solvent is a dibasic ester, water or a combination thereof.

19. The process of claim 1 wherein the acid catalyst comprises stannic chloride or boron trifluoride.

Assignees

• Dahanayake Manilal S
• Douglass Andrew
• Reierson Robert Lee
• Rhodia Operations

Inventors

• Dahanayake Manilal S
• Douglass Andrew
• Reierson Robert Lee

Classifications

• C07C41/09 Primary

  by dehydration of compounds containing hydroxy groups · CPC title

• C08G65/34

  from hydroxy compounds or their metallic derivatives {(C08G65/26 takes precedence)} · CPC title

• C07C43/135

  having more than one ether bond · CPC title