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