Assignee - Roche Vitamins Inc.
April 16, 2002
U.S. Patents: Abstract: A method of making (all-rac.)-.alpha.-tocopherol by the acid-catalyzed condensation of trimethylhydroquinone with isophytol or phytol wherein the condensation is carried out in the presence of a tris(perfluoroalkanesulphonyl or pentafluorobenzenesulphonyl)methane or a metal salt thereof as the catalyst in an organic solvent. In addition to the metal salt, a Bronsted acid, e.g. sulfuric acid, phosphoric acid or p-toluenesulphonic acid, may be used as a co-catalyst. The product of the method of making is the most active member of the vitamin E group.
Ex Claim Text: A method of making (all-rac.)-.alpha.-tocopherol comprising: a) reacting trimethylhydroquinone (TMHQ) with isophytol (IP) or phytol (PH) in an organic solvent and in the presence of a tris(perfluoroalkanesulphonyl)methane, a tris(pentafluorobenzenesulphonyl)methane, a metal tris(perfluoroalkanesulphonyl)methide, or a metal tris(pentafluorobenzenesulphonyl)methide catalyst of formula I: [R.sup.1 SO.sub.2).sub.3 C].sub.x R.sup.2 I wherein R.sup.1 is a perfluoroalkyl group C.sub.n F.sub.2n+1 or pentafluorophenyl, R.sup.2 is a proton or a metal cation selected from the group consisting of boron, magnesium, aluminium, silicon, scandium, titanium, vanadium, vanadyl, manganese, iron, cobalt, nickel, copper, zinc, yttrium, zirconium, rhodium, palladium, silver, tin, lanthanum, cerium, praseodymium, neodymium, europium, dysprosium, ytterbium, hafnium, platinum, and gold, n is an integer from 1 to 10, and x is the corresponding valency of the proton (1) or metal cation (1, 2, 3, or 4); and b) isolating the (all-rac.)-.alpha.-tocopherol.
Patent Number: 6369242
Issue Date: 2002 04 09
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