Process for the manufacture of α-tocopheryl acetate

US7135580B2 · kind B2 · utility

Assignee

• DSM IP ASSETS B.V. · NL

Inventors

• Werner Bonrath · Kaiseraugst, CH
• Claus Dittel · Solothurn, CH
• Lisa Giraudi · Huningue, FR
• Thomas Netscher · Bad Krozingen, DE
• Thomas Pabst · Mintraching, DE

Key dates

• Filing date: Dec 22, 2003
• Grant date: Nov 14, 2006
• Expiry date: Dec 22, 2023

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D311/72
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention is concerned with a novel process for the manufacture of α-tocopheryl acetate which comprises reacting 2,3,6-trimethylhydroquinone-1-acetate with a compound selected from the group consisting of phytol (formula IV with R═OH), iso-phytol (formula III with R═OH), and (iso) phytol derivatives represented by the following formulae III and IV with R═C2-to C5-alkonoyloxy, benzoyloxy, mesyloxy, bezenesul-fonyloxy or tosyloxy,(IV) in the presence of a catalyst of the formula Mn+(R1SO3−)n, wherein Mn+ is a silver, copper, gallium, hafnium or rare earth metal cation, n is the valence of the cation Mn+, and R1 is fluorine, C1-8-perfluoroalkyl or perfluoroaryl, and, if required, cyclizing any 3-phytyl-2,5,6-trimethylhydroquinone-1-acetate or a double bond isomer thereof obtained as an intermediate reaction product, to produce α-tocopheryl acetate. In the catalyst Mn+ is preferably Ag+, Cu+, Ga3+, Sc3+, Lu3+, Ho3+, Tm3+, Yb3+ or Hf4+.