Catalytic oxidation of 3,5,5-trimethylcyclohexa-3-ene-1-one (β-isophorone) with hydrogen peroxide to afford 2,6,6-trimethyl-2-cyclohexene-1,4-dione (keto-isophorone)

US10093605B2 · kind B2 · utility

Assignee

• EVONIK DEGUSSA GMBH · DE

Inventors

• Stephanie Bajus · Hanau, DE
• Jan Caßens · Recklinghausen, DE
• Jens Döring · Dortmund, DE
• Jörg-Joachim Nitz · Essen, DE
• Stephan Kohlstruk · Marl, DE
• Robert Jansen · Collinsville, US

Key dates

• Filing date: Nov 27, 2017
• Grant date: Oct 9, 2018
• Expiry date: Nov 27, 2037

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2601/16
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention provides a novel process for producing 2,6,6-trimethyl-2-cyclohexene-1,4-dione (keto-isophorone) by catalytic oxidation of 3,5,5-trimethylcyclohexa-3-ene-1-one (β-isophorone) with hydrogen peroxide as the oxidant. In particular, the novel process includes phase transfer reagent in a biphasic system including an organic phase and an aqueous phase wherein the biphasic system includes 1) a tungsten polyoxyometallate as catalyst and hydrogen peroxide, and/or 2) a mixture of a) a mineral acid, b) hydrogen peroxide, and c) a metal tungstate.