Method for producing 2,3,5-trimethyl benzoquinone by oxidation of 2,3,6-trimethylphenol

Patent metadata

Field	Value
Publication number	US-10364231-B2
Application number	US-201715676398-A
Country	US
Kind code	B2
Filing date	Aug 14, 2017
Priority date	Jul 2, 2013
Publication date	Jul 30, 2019
Grant date	Jul 30, 2019

Abstract

The invention relates to a method for producing 2,3,5-trimethyl benzoquinone or a compound containing 2,3,5-trimethyl benzoquinone, the method comprising the following steps: Oxidation of 2,3,6-trimethylphenol with oxygen or an oxygen-containing gas in a two-or multi-phase reaction medium in the presence of a catalyst or catalyst system containing at least one copper (II)-halide to a mixture containing 2,3,5-trimethyl benzoquinone, characterized in that the reaction medium contains water and at least one secondary aliphatic acyclic alcohol having 6 or more, preferably 7 or more, carbon atoms.

First claim

The invention claimed is:

1. A mixture consisting essentially of 2,3,5-trimethylbenzoquinone, the mixture being prepared by a process consisting essentially of the following step:
(i) oxidizing 2,3,6-trimethylphenol to 2,3,5-trimethylbenzoquinone with oxygen or an oxygen-containing gas in a two-phase or multiphase reaction medium in the presence of a catalyst or catalyst system at least comprising a copper(II) halide, to give a mixture comprising 2,3,5-trimethylbenzoquinone,

wherein the reaction medium comprises water and at least one secondary aliphatic acyclic alcohol having 6 or more carbon atoms.

2. The mixture according to claim 1 , wherein the mixture has a chlorine content of less than 0.5 g/100 g.

3. The mixture according to claim 1 , wherein the mixture has a lithium content of less than 0.3 g/100 g.

4. The mixture according to claim 1 , wherein the mixture has a copper content of less than 240 mg/kg.

5. The mixture according to claim 2 , wherein the mixture has a lithium content of less than 0.3 g/100 g.

6. The mixture according to claim 5 , wherein the mixture has a copper content from 210 to 240 mg/kg.

7. A mixture comprising 2,3,5-trimethylbenzoquinone, the mixture being prepared by a process consisting essentially of the following step:
(i) oxidizing 2,3,6-trimethylphenol to 2,3,5-trimethylbenzoquinone with oxygen or an oxygen-containing gas in a two-phase or multiphase reaction medium in the presence of a catalyst or catalyst system at least comprising a copper(II) halide, to give a mixture comprising 2,3,5-trimethylbenzoquinone,

wherein the reaction medium comprises water and at least one secondary aliphatic acyclic alcohol having 6 or more carbon atoms wherein the mixture has a copper content from 210 to 220 mg/kg.

8. The mixture as claimed in claim 5 wherein the mixture has a copper content from 210 to 220 mg/kg.

Assignees

• Basf Se

Inventors

• Dehn Richard
• Kraus Michael
• Dehn Martine
• Danz Manuel
• Teles Joaquim Henrique

Classifications

• C07C46/08 Primary

  with molecular oxygen · CPC title

• Y02P20/584

  Recycling of catalysts · CPC title

• C07C50/02

  with monocyclic quinoid structure · CPC title

• C07D311/72 Primary

  3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols · CPC title

• C07C50/04

  Benzoquinones, i.e. C6H4O2 · CPC title