IP Library Granted Patent US 9,975,116
Granted Patent B2
US 9,975,116 · App. 15/531,114 · Granted May 22, 2018

Process for the manufacture of alcohol and/or ketone

Inventors: Sandra Chouzier (Lyons, FR); Luis Fernando Rascon Cruz (Woluwe-Saint-Lambert, BE); Bert Weckhuysen (BV Houten, NL); Sergio Mastroianni (Lyons, FR)
Assignee: Rhodia Operations
B01J37/086B01J23/26B01J27/24B01J37/0018B01J37/06C07C45/53C07C2523/24C07C2523/26C07C2601/14
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Quick Facts
Patent No.
US 9,975,116
App. No.
15/531,114
Granted
May 22, 2018
Kind
B2
Abstract

Process for the manufacture of at least one alcohol and/or at least one ketone, which comprises a step during which at least one organic peroxide compound is put into contact with at least one catalyst responding to formula (I) CrN x O y Formula (I) in which x is a number varying from 0.10 to 1.00 and y is a number varying from 0.00 to 1.50, in order to produce the at least one alcohol and/or at least one ketone.

Claims (24)

1. A process for the manufacture of at least one alcohol and/or at least one ketone, comprising contacting at least one organic peroxide compound with at least one catalyst responding to formula I:

CrN x O y   (formula I)

wherein x is a number from 0.10 to 1.00 and y is a number from 0.00 to 1.50.

2. The process according to claim 1 , wherein x is a number from 0.50 to 1.00 and y is a number from 0.00 to 1.00.

3. The process according to claim 1 , wherein x is a number from 0.50 to 1.00 and y is a number from 0.00 to 0.60.

4. The process according to claim 1 , wherein the catalyst is chosen among:

chromium nitrides of formula CrN x in which x is a number from 0.50 to 1.00;

mixtures comprising such chromium nitrides;

chromium oxynitrides of formula CrN x O y in which x is a number from 0.50 to 1.00 and y is a number from 0.40 to 0.60; and

mixtures comprising such oxynitrides.

5. The process according to claim 1 , wherein the organic peroxide compound is a hydroperoxide compound responding to formula II:

R—O—O—H  (formula II)

in which R is a hydrocarbon group comprising from 1 to 15 carbon atoms.

6. The process according to claim 1 , wherein the organic peroxide compound is a hydroperoxide compound responding to formula II:

R—O—O—H  (formula II)

in which R is a hydrocarbon group comprising from 4 to 9 carbon atoms.

7. The process according to claim 1 , wherein the hydroperoxide compound is chosen in the group consisting of tert-butyl hydroperoxide, tert-amyl hydroperoxide, cumene hydroperoxide, ethylbenzene hydroperoxide, cyclohexyl hydroperoxide and methylcyclohexyl hydroperoxide.

8. The process according to claim 1 , wherein the hydroperoxide compound is chosen in the group consisting of tert-butyl hydroperoxide, cumene hydroperoxide and cyclohexyl hydroperoxide.

9. The process according to claim 1 , wherein the hydroperoxide compound is cyclohexyl hydroperoxide.

10. The process according to claim 9 , wherein the at least one alcohol and/or at least one ketone is cyclohexanol and/or cyclohexanone.

11. The process according to claim 9 , wherein the cyclohexyl hydroperoxide is generated by reaction of a cyclohexane with an oxygen generator.

12. The process according to claim 11 , wherein the oxygen generator is air.

13. The process according to claim 1 , wherein the contact between the peroxide and the catalyst is performed at a temperature from 20° C. to 200° C.

14. The process according to claim 1 , wherein the contact between the peroxide and the catalyst is performed at a pressure from 0.1 MPa to 1.5 MPa.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2020
From: RHODIA OPERATIONS
To: PERFORMANCE POLYAMIDES S.A.S
Reel/Frame 051735/0114 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 4, 2018
From: CHOUZIER, SANDRA; RASCON CRUZ, LUIS FERNANDO; WECKHUYSEN, BERT; MASTROIANNI, SERGIO
To: RHODIA OPERATIONS
Reel/Frame 045431/0168 →
Priority Claims (1)
EP 14306924 · Nov 28, 2014 · regional
Continuity (1)
Related Publication 20170266651A1 · Sep 21, 2017