Process for the manufacture of TMHQ

US8809591B2 · kind B2 · utility

Assignee

• DSM IP ASSETS B.V. · NL

Inventors

• Werner Bonrath · Kaiseraugst, CH
• Thomas Netscher · Bad Krozingen, DE
• Jan Schütz · Bad Kötzting, DE
• Bettina Wüstenberg · Basel, CH

Key dates

• Filing date: Aug 25, 2011
• Grant date: Aug 19, 2014
• Expiry date: Aug 25, 2031

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D311/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention is directed to a process for the manufacture of 2,3,5-trimethyl-hydro-p-benzoquinone comprising the following steps: a) hydrogenating 2,6-dimethyl-p-benzoquinone with hydrogen in the presence of a hydrogenation catalyst in an organic solvent to obtain 2,6-dimethyl-hydro-p-benzoquinone; b) reacting 2,6-dimethyl-hydro-p-benzoquinone with a secondary amine and formal-dehyde in an organic solvent to obtain 2,6-dimethyl-3-(N,N-disubstituted aminomethyl)-hydro-p-benzoquinone; c) reacting 2,6-dimethyl-3-(N,N-disubstituted aminomethyl)-hydro-p-benzoquinone with hydrogen in the presence of a hydrogenolysis catalyst in an organic solvent to obtain 2,3,5-trimethylhydro-p-benzoquinone; wherein the organic solvent in all steps a), b) and c) is independently selected from the group consisting of methyl tert.-butyl ether, ethyl tert.-butyl ether, methyl tert.-amyl ether, methoxycyclopentane and any mixtures thereof. Preferably the organic solvent used in all steps a), b) and c) is the same.