Patent number: 7135580
Abstract: The present invention is concerned with a novel process for the manufacture of ?-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 ?-tocopheryl acetate. In the catalyst Mn+ is preferably Ag+, Cu+, Ga3+, Sc3+, Lu3+, Ho3+, Tm3+, Yb3+ or Hf4+.
Type:
Grant
Filed:
December 22, 2003
Date of Patent:
November 14, 2006
Assignee:
DSM IP Assets B.V.
Inventors:
Werner Bonrath, Claus Dittel, Lisa Giraudi, Thomas Netscher, Thomas Pabst
Publication number: 20060052618
Abstract: The present invention is concerned with a novel process for the manufacture of ?-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 ?-tocopheryl acetate. In the catalyst Mn+ is preferably Ag+, Cu+, Ga3+, Sc3+, Lu3+, Ho3+, Tm3+, Yb3+ or Hf4+.
Type:
Application
Filed:
December 22, 2003
Publication date:
March 9, 2006
Inventors:
Werner Bonrath, Claus Dittel, Lisa Giraudi, Thomas Netscher, Thomas Pabst