Process for the manufacture of chroman derivatives, especially α-tocopherol and alka-noates thereof

US8431727B2 · kind B2 · utility

Assignee

• DSM ASSETS B.V. · NL

Inventors

• Werner Bonrath · Kaiseraugst, CH
• Yann Foricher · Riedisheim, FR
• Thomas Netscher · Bad Krozingen, DE
• Angela Wildermann · Kaiseraugst, CH

Key dates

• Filing date: Mar 6, 2009
• Grant date: Apr 30, 2013
• Expiry date: May 30, 2031

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P3/02
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention relates to novel processes for the manufacture of chroman derivatives such as α-tocopherol (TCP) and alkanoates thereof, especially α-tocopheryl acetate (TCPA), whereby at least one step of the processes is carried out in the presence of a Lewis acid or a mixture of a Lewis acid with a Bronsted acid as the catalyst under pressure, preferably at an absolute pressure of at least 1.1 bar.As starting materials for the manufacture of TCP and its alkanoates either a mixture of 2,3,5-trimethylhydroquinone (TMHQ) or 2,3,6-trimethylhydroquinone-1-alkanoate (TMHQA) and a compound selected from the group consisting of phytol (PH), isophytol (IP) and (iso)phytol derivatives or 2-phytyl-3,5,6-trimethyl-hydroquinone (PTMHQ)/3-phytyl-2,5,6-trimethylhydroquinone-1-alkanoate (PTMHQA) and/or an isomer thereof are used.Suitable Lewis acids are indium(III) salts and scandium(III) salts. Suitable acid mixtures are iron/iron(II) chloride/hydrogen chloride and zinc(II) chloride/hydrogen chloride.