Guerbet alcohols and methods for preparing and using same

Patent metadata

Field	Value
Publication number	US-9840449-B2
Application number	US-201313801209-A
Country	US
Kind code	B2
Filing date	Mar 13, 2013
Priority date	Mar 21, 2012
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

The invention relates to Guerbet alcohol precursors and Guerbet alcohols, as well as to processes for synthesizing them.

First claim

What is claimed is:

1. A method of producing a compound of formula I:

or a salt thereof, wherein each R independently is hydrogen or unsubstituted or substituted C1-C20 alkyl, wherein the alkyl is linear or branched and optionally contains a carbonyl moiety (C═O) within or at the terminus of the alkyl chain, the method comprising:
ozonolysis of a triglyceride, a fatty acid, or a fatty acid ester to obtain a mono-aldehyde having the formula R—CH2CHO; and
dimerizing the mono-aldehyde to obtain the compound of formula I, wherein the dimerization reaction is performed in an alcohol aqueous solution.

2. The method of claim 1 , further comprising, between ozonolysis and dimerization steps, isolating the mono-aldehyde from other ozonolysis products by distillation.

3. The method of claim 2 , wherein the distillation is performed under vacuum.

4. The method of claim 1 , wherein each R independently is alkyl having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, or 16 carbon atoms.

5. The method of claim 1 , wherein each R independently is alkyl having 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms.

6. The method of claim 1 , wherein the dimerization reaction is performed in the presence of an acid or base.

7. The method of claim 1 , wherein the volume ratio between the alcohol and water in the alcohol aqueous solution ranges from 10:1 to 1:10.

8. The method of claim 7 , wherein the alcohol is ethanol.

9. The method of claim 1 , wherein the ozone used in the ozonolysis step is generated by electrolyzing water.

10. The method of claim 9 , wherein hydrogen generated by electrolyzing water is used in the reduction of the compound of formula I to produce a compound of formula II:

or a salt thereof.

11. The method of claim 1 , wherein each R independently is hydrogen, unsubstituted C1-C20 alkyl, or substituted C1-C20 alkyl containing —COOH at the terminus of the alkyl chain.

12. The method of claim 1 , wherein each R independently is alkyl having 4, 5, 6, 7, 8, 9, or 10 carbon atoms.

Assignees

• P2 Science Inc

Inventors

• Foley Patrick
• Yang Yonghua

Classifications

• C07C45/74

  combined with dehydration · CPC title

• C07C31/125

  containing five to twenty-two carbon atoms · CPC title

• C07C29/141 Primary

  with hydrogen or hydrogen-containing gases · CPC title

• C07C59/245

  containing hydroxy or O-metal groups · CPC title

• C07C45/40

  by oxidation with ozone; by ozonolysis · CPC title