Specific dehydrogenation process (I)

Patent metadata

Field	Value
Publication number	US-11851402-B2
Application number	US-202017603114-A
Country	US
Kind code	B2
Filing date	Apr 3, 2020
Priority date	Apr 15, 2019
Publication date	Dec 26, 2023
Grant date	Dec 26, 2023

Abstract

The present invention relates to a new dehydrogenation process of specific compounds.

First claim

The invention claimed is:

1. A process for the production of a compound of formula (II):

wherein
R is —CH═O or —CH 2 OCOR′, wherein R′ is a —C 1 -C 16 alkyl group,
wherein

the process comprises conducting in the presence of at least one oxidative reactant and in the presence of at least one additive compound a selective dehydrogenation of a compound of formula (I):

wherein
R has the same meanings as in the compound of formula (II), wherein
the at least one oxidative reactant is a compound of formula (III):

wherein
R 1 is —CN, —Cl or —F,
R 2 is —CN, —Cl or —F,
R 3 is —H, —CH 3 , —Cl or —F, and
R 4 is —H, —CH 3 , —Cl or —F.

2. The process according to claim 1 , wherein the at least one oxidative reactant is selected from the group consisting of compounds of formulas (IIIa), (IIIb) and (IIIc):

3. The process according to claim 1 , wherein the at least one oxidative reactant is a compound of formula (IIIc):

4. The process according to claim 1 , wherein the at least one oxidative reactant of formula (III) is present in an amount of from 0.5 mol-equivalent up to 5 mol-equivalent in relation to the compound of formula (II).

5. The process according to claim 1 , wherein the at least one additive compound is selected from the group consisting of pyridine, butylhydroxyltoluol, hydroquinone and triethoxyamine.

6. The process according to claim 1 , wherein the at least one additive compound is present in an amount of 0.001—1 mol-equivalent in relation to the compound of formula (II).

7. The process according to claim 1 , wherein the process comprises conducting the selective dehydrogenation in the presence of at least one inert solvent.

8. The process according to claim 7 , wherein the at least one inert solvent is an aromatic hydrocarbon solvent.

9. The process according to anyone of the preceding claims, wherein the process comprises conducting the selective dehydrogenation at a temperature of 0° C.—120° C.

10. The process according to claim 1 , wherein R′ is —CH 3 , —CH 2 CH 3 or —C 15 H 31 .

11. A compound of formula (Ia):

12. A compound of formula (Ib):

Assignees

• Dsm Ip Assets Bv

Inventors

• Bonrath Werner
• Mueller Marc-André
• Wuestenberg Bettina

Classifications

• C07C5/327 Primary

  Formation of non-aromatic carbon-to-carbon double bonds only · CPC title

• C07C5/44

  with halogen or a halogen-containing compound as an acceptor · CPC title

• C07C67/02

  by interreacting ester groups, i.e. transesterification · CPC title

• C07C67/44

  by oxidation-reduction of aldehydes, e.g. Tishchenko reaction · CPC title

• C07C69/145

  of unsaturated alcohols · CPC title