Uses of vanadium to oxidize aldehydes and ozonides

Patent metadata

Field	Value
Publication number	US-10696605-B2
Application number	US-201716333677-A
Country	US
Kind code	B2
Filing date	Sep 15, 2017
Priority date	Sep 16, 2016
Publication date	Jun 30, 2020
Grant date	Jun 30, 2020

Abstract

The present invention relates to uses of vanadium to convert aldehydes and ozonides into their respective acids and/or ketones. More particularly, this invention relates to the oxidative work-ups following ozonolysis using vanadium during ozonolysis, and using vanadium to oxidize aldehydes in general. The invention also relates to methods comprising the ozonolysis of oleyl alcohol in the presence of either an acid or an alcohol.

First claim

The invention claimed is:

1. A method of oxidizing aldehydes to acids, comprising the steps of:
providing vanadium to oxidize aldehydes to carboxylic acids in the presence of air or oxygen at a predetermined temperature range in an acidic solvent, wherein the aldehydes are aliphatic alkyl aldehydes or oxo analogs thereof, aromatic aldehydes, or terpene aldehydes, and wherein the oxidant is air or oxygen gas.

2. The method of claim 1 , wherein said acidic solvent comprises acetic acid.

3. The method of claim 1 , wherein said acidic solvent comprises a carboxylic acid selected from formic, propanoic, butanoic, pentanoic, hexanoic, heptanoic, octanoic, nonanoic, decanoic, dodecanoic, palmitic, and stearic acid.

4. The method of claim 1 , wherein said vanadium comprises vanadium pentoxide.

5. The method of claim 1 , wherein said aldehydes comprise C3 to C15 optionally functionalized linear alkyl aldehydes and said carboxylic acids comprise C3 to C15 optionally functionalized linear alkyl carboxylic acids.

6. The method of claim 1 , wherein said aldehyde is hydroxycitronellal and said carboxylic acid is hydroxycitronellic acid.

7. The method of claim 1 , wherein said aldehyde is methoxymelonal and said carboxylic acid is methoxymelonic acid.

8. The method of claim 1 , wherein said aldehyde is hydroxymelonal and said carboxylic acid is hydroxymelonic acid.

9. The method of claim 1 , wherein said aldehyde is methoxycitronellal and said carboxylic acid is methoxycitronellic acid.

10. The method of claim 1 , wherein said aldehydes are aromatic aldehydes and said carboxylic acids are aromatic carboxylic acids.

11. The method of claim 1 , wherein said aldehyde is 9-oxononanol and said acid is 9-hydroxynonanoic acid.

12. A method of oxidizing a mixture of ozonides and aldehydes, comprising the steps of:
providing vanadium to oxidize mixtures of ozonides and aldehydes to carboxylic acids in the presence of air or oxygen at a predetermined temperature range in an acidic solvent, wherein said ozonides are derived by ozonolysis from an unsaturated fatty monoacid, diacid, monoester, diester, diol, or alcohol, wherein the oxidant is air or oxygen gas.

13. A method of oxidizing an ozonide mixture, comprising the steps of:
providing vanadium to oxidize mixtures of ozonides to ketones, carboxylic acids, or mixtures thereof in the presence of air or oxygen at a predetermined temperature range in an acidic solvent, wherein said ozonides are derived by ozonolysis from an unsaturated fatty monoacid, diacid, monoester, diester, diol, or alcohol, and wherein the oxidant is air or oxygen gas.

14. The method according to claim 13 , wherein the method comprises the steps of reacting oleyl alcohol with ozone to form the ozonides, and oxidizing the ozonides with vanadium to provide 9-hydroxynonanoic acid.

15. The method of claim 14 wherein the vanadium is vanadium pentoxide.

16. The method of claim 14 , wherein the vanadium is used to quench the ozonides and/or any peroxides, and is used to oxidize initially formed aldehydes to the 9-hydroxynonanoic acid.

17. The method according to claim 1 , wherein the aldehyde is nonanal, and the nonanal is oxidized to nonanoic acid using vanadium and air or oxygen.

18. The method according to claim 13 , wherein said ozonides are derived by ozonolysis from an unsaturated fatty alcohol.

19. The method according to claim 13 , wherein the ozonide mixture is continuously passed through a structured reactor or packed tube containing the vanadium.

20. The method according to claim 11 , wherein the method further comprises the oxidation the 9-hydroxynonanoic acid to form the diacid azelaic acid.

21. The method according to claim 14 , wherein the method further comprises the oxidation the 9-hydroxynonanoic acid to form the diacid azelaic acid.

Assignees

• P2 Science Inc

Inventors

• Foley Patrick
• Yang Yonghua
• Salam Tania

Classifications

• B01J23/22 Primary

  Vanadium · CPC title

• C07C51/235

  of —CHO groups or primary alcohol groups · CPC title

• Y02P20/10

  Process efficiency · CPC title

• C07C51/34

  by oxidation with ozone; by hydrolysis of ozonides · CPC title

• C07C45/40

  by oxidation with ozone; by ozonolysis · CPC title