Process for oxidation of alcohols using oxygen-containing gases

Patent metadata

Field	Value
Publication number	US-10179756-B2
Application number	US-201515574524-A
Country	US
Kind code	B2
Filing date	May 18, 2015
Priority date	May 18, 2015
Publication date	Jan 15, 2019
Grant date	Jan 15, 2019

Abstract

A process of oxidizing an alcohol for the production of its corresponding carbonyl compounds is disclosed, wherein the oxidation is performed with oxygen or gases containing oxygen in the presence of a catalyst comprising at least a gold compound and a copper compound. Said alcohol oxidation by gaseous oxidant can achieve a high yield and selectivity with minimized degradation products or waste organic solvents.

First claim

The invention claimed is:

1. A process of oxidizing an alcohol of formula (I) for the production of its corresponding carbonyl compounds
R—OH  (I)

wherein R represents a saturated or unsaturated, linear, branched or cyclic C 7 -C 50 hydrocarbon group which optionally comprises a heteroatom and which optionally comprises a substituent, the process comprising oxidizing an alcohol of formula (I) with oxygen or gases containing oxygen, in the presence of a catalyst comprising at least a gold compound and a copper compound.

2. The process according to claim 1 , wherein R represents a saturated or unsaturated, linear, branched or cyclic C 7 -C 50 hydrocarbon group which optionally comprises a heteroatom, and comprises a substituent selected from the group consisting of: alkyl, alkenyl, aryl, oxygen-containing group and nitrogen containing group.

3. The process of claim 1 , wherein the alcohol is an ethoxylated alcohol of formula (II)
R 1 (OCH 2 CHR 2 ) n OCH 2 CH 2 OH  (II)

wherein: R 1 represents an alkyl radical having 1 to 22 carbon atoms or a monounsaturated or polyunsaturated linear or branched alkenyl radical having 2 to 22 carbon atoms, optionally comprising at least a substituent and/or a heteroatom; R 2 represents a hydrogen atom or a methyl group or a mixture thereof in the individual molecule; and n has an average number between 2 and 20.

4. The process of claim 3 , wherein R 1 is selected from a group consisting of methyl, butyl and lauryl.

5. The process of claim 3 , wherein R 1 is an alkyl group substituted with at least one substituent selected from a group consisting of —OR 3 , —CH 3 , —CH 2 CH 3 , —COOH, —CONH 2 and —COOR 3 , wherein R 3 represents an alkyl or aryl group.

6. The process of claim 3 , wherein one or more ethoxylated alcohols of formula (II) are oxidized to produce compounds of formula (III)
R 1 (OCH 2 CHR 2 ) n OCH 2 COOB  (III)

with B being a cation, and/or of the corresponding protonated carboxylic acids.

7. The process of claim 6 , further comprising reacting the compounds of formula (III) with acids.

8. The process of claim 1 , wherein the alcohol is an acid monoethanolamide of formula (IV)

wherein R′ represents a saturated, linear or branched alkyl radical having from 4 to 25 carbon atoms or a monounsaturated or polyunsaturated linear or branched alkenyl radical having from 4 to 25 carbon atoms.

9. The process of claim 8 , wherein the acid monoethanolamide of formula (IV) is lauric acid monoethanolamide.

10. The process of claim 8 , wherein one or more fatty acid monoethanolamides of formula (IV) are oxidized to produce compounds of formula (V)

with B being a cation, and/or of the corresponding protonated acylglycine acids.

11. The process of claim 1 , wherein the catalyst is applied to a support selected from the group consisting of activated carbon and oxide supports.

12. The process of claim 11 , wherein the support is an oxide support selected from the group consisting of zinc oxide, magnesium oxide, cerium dioxide and aluminium oxide.

13. The process of claim 1 , wherein the pH during the oxidation reaction is between 9 and 15.

14. The process of claim 1 , wherein the oxidation reaction occurs at a temperature between 30° C. and 100° C.

Assignees

• Rhodia Operations
• Centre Nat Rech Scient

Inventors

• Zhou Wenjuan
• Fang Wenhao
• Liebens Armin T

Classifications

• C07C231/14

  by formation of carboxamide groups together with reactions not involving the carboxamide groups · CPC title

• C07C51/245

  of keto groups or secondary alcohol groups · CPC title

• C07C51/235 Primary

  of —CHO groups or primary alcohol groups · CPC title

• C07C51/23

  of oxygen-containing groups to carboxyl groups · CPC title

• B01J37/16

  Reducing · CPC title