Abstract: The present invention relates to a process for the manufacture of a tocopheryl acylate which comprises reacting a tocopherol with an acylating agent in the presence of a solid basic catalyst comprising, an alkali metal and/or alkaline earth metal preferably on a solid carrier and to the use of such catalysts in the acylation of tocopherols.

Abstract: The present invention relates to a novel process for the manufacture of Grewe-diamine comprising the following step: hydrolyzing a compound of formula (II), wherein R is hydrogen or straight- or branched chain C1-4 alkyl, with an aqueous alkali or alkaline-earth metal hydroxide solution, characterized in that the hydrolysis is carried out in the presence of an organic solvent.

Abstract: Saturated aliphatic ketones, e.g. hexahydropseudoionone, may be prepared by hydrogenating an olefinically unsaturated ketone, e.g. pseudoionone in a continuous fixed-bed mode in the absence of a solvent in the presence of a catalyst comprising a noble metal deposited on a carrier.

Abstract: The invention relates to the (stereoselective) hydrogenation of carbon-carbon double bonds in compounds having at least one such bond, e.g., isoprenoids, non-cyclic sesquiterpenes, tocomonoenols, tocodienols, tocotrienols or derivatives thereof, as well as to the (stereoselective) hydrogenation of parts/extracts of plant oils containing such tocotrienols or derivatives thereof, in the presence of a chiral Ir complex as the catalyst, whereby preferably one stereoisomer is manufactured in an excess.

Abstract: A process for the manufacture of a tocyl acylate or a tocopheryl acylate comprises reacting tocol or a tocopherol with an acylating agent in the presence of a solid heterogeneous Brönsted acid catalyst, said catalyst being an inorganic Brönsted acid on a solid carrier material which comprises silicon dioxide, titanium dioxide or both silicon dioxide and titanium dioxide, or being an organofunctional polysilonaxe featuring sulpho groups, the solid heterogeneous Brönsted acid catalyst further featuring a BET surface area from about 10 m2/g to about 800 m2/g and a pore volume from about 0.1 ml/g to about 2.0 ml/g. The main commercial form of vitamin E, being (all-rac)-?-tocopheryl acetate, can be manufactured by acylation of (all-rac)-?-tocopherol according to this process.

Abstract: Methylheptenone (2-methyl-2-hepten-6-one) is prepared by reacting 2-methyl-3-buten-2-ol with isopropenyl methyl ether in the presence of hydrogen tris(oxalato)phosphate or hydrogen bis(oxalato)borate.

Abstract: The present invention relates to a process for the manufacture of a tocopheryl acylate which comprises reacting a tocopherol with an acylating agent in the presence of a solid basic catalyst comprising, an alkali metal and/or alkaline earth metal preferably on a solid carrier and to the use of such catalysts in the acylation of tocopherols.

Abstract: Methylheptenone (2-methyl-2-hepten-6-one) is prepared by reacting 2-methyl-3-buten-2-ol with isopropenyl methyl ether in the presence of hydrogen tris(oxalato)phosphate or hydrogen bis(oxalato)borate.

Abstract: A process for the manufacture of 3-phytyl-2,5,6-trimethylhydroquinone-1-acetate, and optionally therefrom tocopheryl acetate, comprises either C-alkylating 2,3,6-trimethylhydroquinone-1-acetate with isophytol or phytol in the presence of a sulphur(VI) containing catalyst of the formula R1SO2OH, wherein R1 signifies hydroxy, halogen, lower alkyl, halogenated lower alkyl or aryl, in an aprotic organic solvent, or O-alkylating 2,3,6-trimethylhydroquinone-1-acetate with a phytyl halide in a polar aprotic organic solvent in the presence of a base, and subjecting the so-obtained 4-O-phytyl-2,3,6-trimethylhydro-quinone-1-acetate to a rearrangement reaction, and in each case optionally submitting the so-obtained 3-phytyl-2,5,6-trimethylhydroquinone-1-acetate to a ring closure reaction to produce tocopheryl acetate.

Abstract: The present invention is directed to a process for the manufacture of a 2,3,5-trimethyl-hydroquinone dialkanoate comprising reacting ketoisophorone with an acylating agent in the presence of an indium salt as the catalyst. Preferred are indium(III) salts such as indium trichloride or indium tris(trifluoromethanesulfonate). Further aspects of the present invention are a process for the manufacture of 2,3,5-tri-methylhydroquinone using 2,3,5-trimethylhydroquinone dialkanoate as the starting mate-rial, especially a process for the manufacture of 2,3,5-trimethylhydroquinone by trans-esterification of 2,3,5-trimethylhydroquinone dialkanoate, as well as a process for the manufacture of a-tocopherol and its alkanoates, especially of (all-rac)-a-tocopherol and its acetate, comprising the reaction of ketoisophorone to 2,3,5-trimethylhydroquinone dialka-noate according to the present invention.

Abstract: The present invention is concerned with a novel process for the manufacture of 4alkanoyloxy-2,3,5-trimethylphenyl (E/Z)-phytyl ethers, precursors of ?-tocopheryl alkanoates, by cross-metathesis reaction of alkenyl ethers of 1-alkanoyloxy-2,3,6-trimethylhydroquinone with 2,6,10,14-tetramethylpentadecene or a phytol derivative, e.g. an ester, an ether or a silyl ether, in the presence of a cross-metathesis catalyst. As the crossmetathesis catalyst especially ruthenium metal carbene complexes are suitable which possess (a) ruthenium metal center(s), have an electron count of 16 or 18 and are penta- or hexa-coordinated. A further object of the invention is a process for the manufacture of atocopheryl alkanoates comprising this reaction.

Abstract: A process for the manufacture of 3-phytyl-2,5,6-trimethylhydroquinone-1-acetate, and optionally therefrom tocopheryl acetate, comprises either C-alkylating 2,3,6-trimethylhydroquinone-1-acetate with isophytol or phytol in the presence of a sulphur(VI) containing catalyst of the formula R1SO2OH, wherein R1 signifies hydroxy, halogen, lower alkyl, halogenated lower alkyl or aryl, in an aprotic organic solvent, or O-alkylating 2,3,6-trimethylhydroquinone-1-acetate with a phytyl halide in a polar aprotic organic solvent in the presence of a base, and subjecting the so-obtained 4-O-phytyl-2,3,6-trimethylhydroquinone-1-acetate to a rearrangement reaction, and in each case optionally submitting the so-obtained 3-phytyl-2,5,6-trimethylhydroquinone-1-acetate to a ring closure reaction to produce tocopheryl acetate.

Abstract: A process for the manufacture of a tocyl acylate or a tocopheryl acylate comprises reacting tocol or a tocopherol with an acylating agent in the presence of a solid heterogeneous Brönsted acid catalyst, said catalyst being an inorganic Brönsted acid on a solid carrier material which comprises silicon dioxide, titanium dioxide or both silicon dioxide and titanium dioxide, or being an organofunctional polysilonaxe featuring sulpho groups, the solid heterogeneous Brönsted acid catalyst further featuring a BET surface area from about 10 m2/g to about 800 m2/g and a pore volume from about 0.1 ml/g to about 2.0 ml/g. The main commercial form of vitamin E, being (all-rac)-?-tocopheryl acetate, can be manufactured by acylation of (all-rac)-?-tocopherol according to this process.

Abstract: A process for the manufacture of (all-rac)-?-tocopherol by the acid-catalyzed reaction of trimethylhydroquinone with isophytol or phytol is characterized by carrying out the reaction in the presence of methane trisulphonate as the catalyst in an organic solvent. The product of the process is the most active and industrially most important member of the vitamin E group.

Abstract: A process for the manufacture of 2,3,5-trimethylhydroquinone diacylate comprising reacting ketoisophorone with an acylating agent in the presence of a NH- or CH-acidic catalyst, particularly certain bis(perfluorinated hydrocarbyl sulphonyl) imides and metal salts thereof and, respectively, certain tris(perfluoroalkanesulphonyl or pentafluorobenzenesulphonyl) methanes and metal salts thereof. The acylating agent is particularly an acid anhydride, an acyl halide or an enol ester. The so-obtained 2,3,5-trimethylhydroquinone diacylate can be converted into (all-rac)-?-tocopherol by transesterification to yield 2,3,5-trimethylhydroquinone and reaction of the latter with isophytol. (all-rac)-?-Tocopherol itself is the most active member of the vitamin E group.

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+.

Abstract: The present invention is concerned with a novel process for the manufacture of (E/Z)-4-alkanoyloxy-3,5,6-trimethyl-2-phytylphenyl esters and silyl ethers, precursors of ?-tocopherol and ?-tocopheryl alkanoates, by cross-metathesis reaction of 2-alkenyl-3,5,6-trimethylhydroquinone dialkanoates or 4-alkanoyloxy-2-alkenyl-3,5,6-trimethylphenyl silylethers with 2,6,10,14-tetramethylpentadecene or a phytol derivative, e.g. phytyl acetate, in the presence of a cross-metathesis catalyst. As the cross-metathesis catalyst especially ruthenium metal carbene complexes are suitable which possess (a) ruthenium metal center(s), have an electron count of 16 or 18 and are penta- or hexa-coordinated. A further object of the invention is a process for the manufacture of ?-tocopherol and ?-tocopheryl alkanoates comprising this reaction.

Abstract: The present invention is concerned with a novel process for the manufacture of tocol, tocol derivatives and tocopherols, especially ?-tocopherol, by the reaction of a hydroquinone featuring 0 to 3 methyl groups, especially 2,3,5-trimethylhydroquinone, with isophytol, phytol or a(n) (iso)phytol derivative, most preferably with isophytol, in the presence of gadolinium trifluoromethanesulfonate, Gd(OSO2CF3)3, as the catalyst in a biphasic solvent system. This biphasic solvent system consists essentially of a polar organic solvent and a non-polar organic solvent. The polar organic solvent is preferably ethylene carbonate and/or propylene carbonate. The non-polar solvent is preferably at least a solvent selected from the group consisting of hexane, heptane, octane, cyclohexane and methylcyclohexane.

Abstract: A process for the manufacture of 3-phytyl-2,5,6-trimethylhydroquinone-1-acetate, and optionally therefrom tocopheryl acetate, comprises either C-alkylating 2,3,6-trimethylhydroquinone-1-acetate with isophytol or phytol in the presence of a sulphur(VI) containing catalyst of the formula R1SO2OH, wherein R1 signifies hydroxy, halogen, lower alkyl, halogenated lower alkyl or aryl, in an aprotic organic solvent, or O-alkylating 2,3,6-trimethylhydroquinone-1-acetate with a phytyl halide in a polar aprotic organic solvent in the presence of a base, and subjecting the so-obtained 4-O-phytyl-2,3,6-trimethylhydroquinone-1-acetate to a rearrangement reaction, and in each case optionally submitting the so-obtained 3-phytyl-2,5,6-trimethylhydroquinone-1-acetate to a ring closure reaction to produce tocopheryl acetate.

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+.