- SYNTHESIS OF CHROMANOL AND 2-METHYL-1,4-NAPHTHOQUINONE DERIVATIVES
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The present invention relates to a process for the production of chromanol and 2-methyl-1,4-naphthoquinone derivatives, more specifically to a process for preparing a compound of the general formula (I) or (II) wherein the variables are as defined in the claims and the description.
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Page/Page column 49-50; 61-62; 68-69
(2020/03/05)
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- Method for preparing vitamin E acetate
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The invention provides a method for preparing vitamin E acetate. The method has the characteristic of high product selectivity; a catalyst used in the method provided by the invention facilitates recovery and reutilization and has less corrosion to equipment; and a product has good stability. The method for preparing the vitamin E acetate provided by the invention prepares the vitamin E acetate through a reaction of 2,3,5-trimethylhydroquinone diester and isophytol, wherein the reaction is carried out in the presence of the catalyst; and with a molecular sieve as a carrier, the catalyst is prepared by loading Bronsted acid, metal halide, metallocene and a metal element onto the molecular sieve.
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Paragraph 0068; 0069; 0070; 0071; 0073
(2019/05/15)
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- Vitamin E acetate preparation method (by machine translation)
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The invention relates to a technical field of chemical synthesis, in particular relates to a vitamin E acetate preparation method, in order to trimethyl [...][...] as raw materials, innovative in a sulfuric acid and paratoluene sulfonic acid under acidic conditions, using magnesium sulfate as a catalyst, greatly improves the catalytic efficiency; in addition, in concentrated hydrochloric acid and ethyl acetate under the reaction environment, esterification synthetic vitamin E acetate efficiency is higher; and, synthetic route of this invention relates to the reaction of the routine chemical reaction, mild reaction conditions, simple operation, is suitable for industrial. (by machine translation)
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Paragraph 0013
(2019/01/06)
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- Method for preparing d1-alpha tocopheryl acetate
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The invention relates to a method for preparing d1-alpha tocopheryl acetate. According to the method, d1-alpha tocopherol or a mixture of d1-alpha tocopherol and d1-alpha tocopheryl acetate serves as a raw material, nitrogen-containing alkaline matter is adopted as a catalyst, acetic acid or acetic anhydride or a mixture of acetic acid and acetic anhydride serves as an acylating agent, and a d1-alpha tocopheryl acetate product is obtained through an esterification reaction. The preparation method is simple as a whole, operability is good, the yield is high, product quality is good, and besides risks in the aspects of the environment and safety are small.
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Paragraph 0033; 0034
(2016/11/14)
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- dl-alpha tocopherol acetate preparation method
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The present invention relates to a dl-alpha tocopherol acetate preparation method, wherein trimethyl hydroquinone diethyl ester or trimethyl hydroquinone-4-ethyl ester is adopted as a raw material, Bronsted acid and Lewis acid are adopted as catalysts, the raw material and phytol or isophytol or a phytol derivative are directly subjected to a condensation reaction in an ester solvent to obtain the product dl-alpha tocopherol acetate or an intermediate dl-alpha tocopherol, wherein the intermediate dl-alpha tocopherol is subjected to further esterification to obtain the product dl-alpha tocopherol acetate. According to the present invention, the process route is simple, the production cost is reduced, the quality of the obtained product is good, the yield is high, and the method is suitable for large-scale industrial production.
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Paragraph 0040; 0041; 0042; 0043; 0044; 0045
(2016/10/24)
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- ACYLATIONS IN MICRO REACTION SYSTEMS
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A method for acylating tertiary alcohols and phenolic compounds with carboxylic acids or their anhydrides in micro-reaction systems wherein the acylation is effected in the absence of any catalyst including water at residence times of at most 30 minutes.
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Page/Page column 8-9
(2011/08/04)
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- A Convenient access to (All-rac)-α-tocopherol acetate from linalool and dihydromyrcene
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Refluxing trimethylhydroquinone 2 in 10:1 dodecane/CH2Cl 2 with linalool 3b (two-fold excess) and camphorsulfonic acid, then treating the crude condensation product (consisting of a mixture of the chromanols 1b and 1c, alongside the tricyclic compounds 9 and 10) sequentially with Ac2O and m-CPBA afforded, after removal by column chromatography of the 9/10 acetates, a mixture of the regioisomeric epoxides 1jOAc and 1kOAc (ratio 9:1, total 60%). Treatment of this mixture with Al(O-i-Pr)3 followed by CuI-catalysed Wurtz coupling of the acetates of the resulting allylic alcohols with citronellylmagnesium chloride 12a, and finally hydrogenation then provided the title acetate (overall 46% from 2).
- Gembus, Vincent,Sala-Jung, Nathalie,Uguen, Daniel
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experimental part
p. 829 - 842
(2009/12/25)
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- PROCESS FOR THE ACYLATION OF ORGANIC HYDROXY COMPOUNDS
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A process for acylating organic hydroxy compounds, characterized in that the acylation is effected in the presence of a metal oxide which does not carry a catalyst and the use of such metal oxides for acylating organic hydroxy compounds.
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Page/Page column 6-8
(2008/12/06)
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- METHOD OF MAKING PURIFIED ODOR FREE TOCOPHEROL ACETATE
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A process for producing odor free tocopherol acetate is disclosed. This process comprises forming a solution of tocopherol acetate in a suitable solvent, e.g., isopropyl alcohol, subjecting said solution to a sufficient amount of low pressure and heat to remove said solvent and sparging sufficient amount of an inert gas through said solution to remove traces of remaining solvent.
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Page/Page column 1-2
(2008/12/06)
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- PROCESS FOR THE MANUFACTURE OF TOCOPHERYL ACYLATES
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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.
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Page/Page column 8-9; 11
(2008/06/13)
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- PROCESS FOR THE MANUFACTURE OF ALKENYLATED HYDROXYLATED AROMATIC COMPOUNDS, OF CHROMAN COMPOUNDS AND OF THEIR ACYLATED DERIVATIVES
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The present invention relates to a novel process for the manufacture of alkenylated aro-matic compounds featuring at least one hydroxy group, their ring-closure reactions to chroman derivatives, as well as the acylation of the latter and the aromatic compounds featuring at least one hydroxy group themselves. The present invention relates especially to a process for the manufacture of tocol, tocopherols and their alkanoates such as α-tocopherol (TCP) and alkanoates (TCPA) thereof, preferably α-tocopheryl acetate (TCPAc). The processes of the present invention are characterized in that at least one step of the processes is carried out in the presence of an indium salt as the catalyst. Thus, an object of the present invention is the use of an indium salt as the catalyst in Friedel-Crafts alkylation reactions of aromatic compounds featuring at least one hydroxy group and ring-closure reactions of the latter to produce chroman-ring compounds in organic solvents. According to another aspect of the invention indium salts can be used as the catalyst in processes for the manufacture of tocyl alkanoates, tocopheryl alkanoates and alkanoates of aromatic compounds featuring at least one hydroxy group by reacting tocols, tocopherol and aromatic compounds featuring at least one hydroxy group, respectively, with an acylating agent. Suitable indium salts are indium(III) salts, especially indium trichloride, indium tribromide or indium triiodide, indium(III) triflate, indium(III) bis(trifluoromethanesulfonamide) and indium(III) acetate. In preferred embodiments of the invention the processes are carried out at a pressure of at least 0.96 bar, whereby the acylation can be carried out at an absolute pressure of at least 0.02 bar.
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Page/Page column 38-39
(2008/06/13)
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- MANUFACTURE OF TOCOPHEROLS USING A BISMUTH CATALYST
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The present invention is concerned with a novel process for the manufacture of tocols and tocopherols, especially α-tocopherol, and cc-tocopheryl acetate by the reaction of a hydroquinone comprising 0 to 3 methyl groups, especially 2,3,5-trimethylhydroquinone, or 2,3,6--trimethylhydroquinone- 1 -acetate, respectively, with isophytol, phytol or a(n) (iso)phytol derivative, most preferably with isophytol, in the presence of bismuth trifluoromethanesulphonate, Bi(OS02CF3)3, as the catalyst in an organic solvent or a biphasic solvent system. A further object of the invention is the use of bismuth trifluoromethanesulphonate, Bi(OS02CF3)3, as the catalyst in Friedel-Crafts type alkylation reactions and ring-closure reactions in organic solvents.
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Page/Page column 14-15
(2008/06/13)
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- MANUFACTURE OF TOCOPHERYL ACETATE
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A process for the manufacture of 3-phytyl-2,5,6-trimethylhydroquinone-l-acetate, and optionally therefrom tocopheryl acetate, comprises either C-alkylating 2,3,6-trimethylhydroquinone-l-acetate with isophytol or phytol in the presence of a sulphur(VI) containing catalyst of the formulaR1SO2OH, wherein Rl signifies hydroxy, halogen, lower alkyl, halogenated lower alkyl or aryl, in an aprotic organic solvent, or O-alkylating 2,3,6-trimethylhydroquinone-l-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-l-acetate to a rearrangement reaction, and in each case optionally submitting the so-obtained 3-phytyl-2,5,6-trimethylhydroquinone-l-acetate to a ring closure reaction to produce tocopheryl acetate. The invention also includes the novel compound 3-phytyl-2,5,6-trimethylhydroquinone-l-acetate and certain stereoisomers thereof, and also the further novel compound 4-hydroxy-2,3,6-trimethyl-5-[3-(4,8,12-trimethyltridecyl)-but-3enyl]phenyl acetate which itself is one of several isomers of 3-phytyl-2,5,6- trimethylhydroquinone-l-acetate formed by isomerization under the influence of heating, e.g. during its distillation as part of the isolation and purification procedure following its manufacture as indicated above. (All-rac)-α -tocopherol, which may be derived from its acetate, is known to be the most active industrially important member of the vitamin E group.
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- Method for continuously acylating chromanol ester derivatives
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A process is described for continuously preparing chromanol ester derivatives, in particular for continuously preparing carboxylic esters of tocopherols and tocotrienols by continuous acylation with carboxylic acids or carboxylic anhydrides.
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- PROCESS FOR THE MANUFACTURE OF α-TOCOPHERYL ACETATE
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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, benzenesul-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+.
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- Intermediates for use in the preparation of vitamin E
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Novel intermediate compounds which can be used in the preparation of phytone and Vitamin E and a process for the preparation thereof. A process for the preparation of phytone and Vitamin E from these compounds is also claimed.
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- Rhodium(I)-catalyzed addition of phenols to dienes. A new convergent synthesis of vitamin E
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A highly convergent and atom-economical synthesis of (dl)-[α]- tocopherol (vitamin E) is proposed, the realization of which was made possible by the discovery of the regioselective Rh(I)-catalyzed arylation of β-springene with trimethylhydroquinone. Other phenolic compounds and 2- substituted-1,3-dienes were shown to undergo this transformation. (C) 2000 Elsevier Science Ltd.
- Bienaymé, Hugues,Ancel, Jean-Erick,Meilland, Pierre,Simonato, Jean-Pierre
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p. 3339 - 3343
(2007/10/03)
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- Process for producing DL-tocopherols and intermediates therefor
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The present invention relates to a process for producing dl-tocopherols and intermediates for the production. dl-Tocopherols obtained by the present invention are useful compounds that are used as food additives, feed and medicaments.
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