Process for the oxidation of mesitol

Patent metadata

Field	Value
Publication number	US-8957260-B2
Application number	US-201213364532-A
Country	US
Kind code	B2
Filing date	Feb 2, 2012
Priority date	Feb 7, 2011
Publication date	Feb 17, 2015
Grant date	Feb 17, 2015

Abstract

The invention relates to a process for the oxidation of mesitol with singlet oxygen, which is released from hydrogen peroxide, this release taking place in the presence of a bismuth compound as catalyst. In the process, 2,4,6-trimethylquinol is formed in high yield and selectivity as product, which can be used in further reactions for the synthesis of vitamins and in particular of vitamin A and vitamin E.

First claim

We claim:

1. A process for the oxidation of mesitol with singlet oxygen, which is released from H 2 O 2 , wherein the release is effected with a bismuth compound as catalyst wherein, the bismuth compound is selected from the group of bismuth oxides and/or bismuth nitrates and/or bismuth nitrate oxides and/or bismuth cobalt zinc oxide (Bi—Co—Zn—O) and/or bismuth citrate and/or from a mixture of these compound groups or compounds.

2. The process according to claim 1 , wherein the mesitol is introduced as initial charge in a water-miscible solvent.

3. The process according to claim 2 , wherein the mesitol is introduced as initial charge in a lower alcohol having 1 to 6 carbon atoms as solvent.

4. The process according to claim 2 , wherein the solvent is rendered alkaline with a base.

5. The process according to claim 4 , wherein the solvent is rendered alkaline with the base, comprising an aqueous solution of an alkali metal or alkaline earth metal hydroxide and/or an alcoholate and/or a hydride.

6. The process according to claim 4 , wherein the solvent is rendered alkaline with the base, where further reactants are only added after the base has completely dissolved.

7. The process according to claim 4 , wherein the base is added in a molar ratio which corresponds to 0.1 to 10-fold the molar amount of the mesitol.

8. The process according to claim 4 , wherein the base is brought into solution mechanically.

9. The process according to claim 4 , wherein the bismuth compound is added to the alkaline solvent comprising mesitol.

10. The process according to claim 1 , wherein, per mole equivalent of bismuth compound, between 1 and 50 molar equivalents of mesitol are used.

11. The process according to claim 4 , wherein H 2 O 2 is added to the alkaline solvent comprising mesitol and bismuth compound.

12. The process according to claim 4 , wherein, per mole equivalent of mesitol, a 2 to 70-fold molar excess of H 2 O 2 is added to the alkaline solvent.

13. The process according to claim 1 , wherein the H 2 O 2 has a concentration of 5 to 60 wt % in water.

14. The process according to claim 4 , wherein the H 2 O 2 is added to the alkaline solvent comprising mesitol and bismuth compound over a period of from 30minutes to 14 hours.

15. The process according to claim 4 , wherein the H 2 O 2 is added to the alkaline solvent continuously.

16. The process according to claim 2 , wherein the H 2 O 2 is added at a temperature of the solvent of from 0 to 90° C.

17. The process according to claim 1 , wherein the molar ratio between bismuth compound and H 2 O 2 is between 1:20 and 1:400.

18. The process of claim 1 , wherein the oxidized mesitol is used for the production of 2,3,6-trimethylhydroquinone.

19. The process of claim 1 , wherein the oxidized mesitol is used for the production of vitamin E.

Assignees

• Weis Martine
• Teles Joaquim Henrique
• Ebel Klaus
• Deglmann Peter
• Weyrauch Vivien Ellinor
• Weyrauch Gunhild
• Basf Se

Inventors

• Weyrauch Jan Philipp
• Weis Martine
• Teles Joaquim Henrique
• Ebel Klaus
• Deglmann Peter

Classifications

• C07C49/713

  a keto group being part of a six-membered ring · CPC title

• C07C39/08

  Dihydroxy benzenes; Alkylated derivatives thereof · CPC title

• C07C2101/16

  Chemistry & Metallurgy · mapped topic

• C07C37/07 Primary

  with simultaneous reduction of C=O group in that ring · CPC title

• C07C45/28

  of CHx-moieties · CPC title