Process of producing 2,3-dimethoxy-5-methyl-1,4-benzoquinone

FIELD: chemistry.

SUBSTANCE: invention relates to the method of producing 2,3-dimethoxy-5-methyl-1,4-benzoquinone, a key intermediate in the synthesis of ubiquinones (coenzymes of the Qn series), in particular of coenzyme Q10, widely used in medical practice and cosmetology, as well as its synthetic analogue - idebenone - a drug for the treatment of Alzheimer's disease. The method consists in oxidizing 3,4,5-trimethoxytoluene with hydrogen peroxide in an organic solvent medium. Herewith the acid tetrabutylammonium salts of the vanadium-containing polyoxo-tungstate (C4H9)4N)5-nHn[γ-PV2W10O40], where the number of protons n in the cationic part of the polyox-tungstate varies from 1 to 2, as co-catalyst, HClO4 with respect to the catalyst, 0.5-1 equivalents, as the organic solvent, preferably acetonitrile is used, the process is carried out at the temperature of, at least, 30°C, at the molar ratio of 3,4,5-trimethoxytoluene: the catalyst is not lower than 40 and the concentration of 3,4,5-trimethoxytoluene is not higher than 0.4M, an aqueous solution of hydrogen peroxide with a peroxide content of, at least, 30 wt %, the process is carried out at the molar ratio of hydrogen peroxide: 3,4,5-trimethoxyphenol not less than 2.

EFFECT: desired product in high yield without the formation of a large amount of by-products.

2 cl, 1 tbl, 23 ex

 



 

Same patents:

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to new polyprenylated 1,4-benzoquinones of formula 1 or formula 3 or polyprenylated 1,4-hydroquinones of formula 2 or formula 4, or to their pharmaceutically acceptable salts exhibiting anticarcinogenic activity 1, 2, 3, 4. In formulae 1-4 each of R1 and R2, irrespectively of others, can be a hydrogen radical or (C1-C6)-alkoxy-group; each of R3 and R4 irrespectively of others, can be a hydrogen radical or (C1-C6)-alkyl group; n can be equal to 2 or 3.

EFFECT: provided application of new compounds and some common 1,4-benzoqunones and 1,4-hydroqunones for preparing a drug, a based pharmaceutical composition, development of a method of oncotherapy, a method of inducing AP-1-dependent or NF-kB-independent transcription activity or both activities simultaneously in a cell and a method of inducing apoptosis in a cell, as well as separating glabruquinones.

21 cl, 3 tbl, 28 dwg, 26 ex

The invention relates to organic chemistry and can be used in the synthesis of 4-alkyl-ortho-benzoquinoines and 3-bromo-5-alkyl-ortho-benzoquinoines

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing 2,6-diisobornylbenzoquinone. The field of use of quinones has been widening lately. Quinones are uses as reactants in organic synthesis, as stabilisers and antioxidants of polymers and organic materials and as catalysts for chemical reactions. The method involves oxidation of olefins in form of 2,6-diisobornylphenol or 3,5-diisobornyl-4-hydroxybenzaldehyde, chlorine dioxide with molar ratio of reactants equal to 1:1-5, respectively, in an organic solvent by bubbling chlorine dioxide with air at temperature from -10 to 40°C.

EFFECT: efficient method of producing 2,6-diisobornylbenzoquinone.

11 cl, 17 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing pentacyclo[7.5.0.02.8.05.14.07.11]tetradeca-3,12-diene of formula The method is characterised by catalytic dimerisation of 1,3,5-cycloheptatriene (CHT). The catalyst system used is NbCl5-Et2AlCl. The reaction is carried out with molar ratio CHT:NbCl5:Et2AlCl=10:(0.1-0.3):4, in argon atmosphere, at 20-100°C, in benzene for 8-48 hours.

EFFECT: method enables to separately obtain the end product.

1 tbl, 7 ex

FIELD: chemistry.

SUBSTANCE: invention relates to field of catalyst. Described is method of obtaining catalyst for ethylene polymerization and copolimerisation of ethylene with alpha-olefins, containing vanadium compound on magnesium-containing carrier, which is obtained by interaction of solution of magnesium-organic compound with composition Mg(C6H5)2nMgCl2mR2O, where; n=0.37-0.7, m=2, R2O is ether with R=i-Am, n-Bu with chlorinating agent phenyltrichloromethane PhCCl3 with mole ratio PhCCl3/MgR2≥1.0, with further processing of carrier with alkylaluminium chloride and application of vanadium compound, with alkylaromatic ether being preliminarily introduced into magnesium organic compound at temperature 20-40°C with molar ratio alkylaromatic ether/Mg=0.05-0.2.

EFFECT: obtained catalyst makes it possible to obtain polymers with wide molecular-weight distribution, increased bulk density and high output.

1 tbl, 5 ex

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The invention relates to methods for applied catalyst ziperovich type containing as an active ingredient a compound of vanadium deposited on a magnesium-containing carrier, and used in combination with an alkyl aluminum as acetalization

The invention relates to a method for producing a catalyst-type Ziegler-Natta based on the precipitation of vanadium compounds on MgCl2spherical media

FIELD: chemistry.

SUBSTANCE: disclosed is a catalyst system for highly selective trimerisation of ethylene into 1-hexene, which consists of a chromium (III) complex with a branched structure, having one or more substitutes in a hydrocarbon SNS skeleton, and an activator which is a mixture of trimethylaluminium and methylaluminoxane, wherein the molar ratio of the components of the catalyst system [Cr]:TMA:MAO is equal to 0.4%:49.8%:49.8%.

EFFECT: catalyst provides high selectivity of the process of trimerising ethylene into 1-hexene while minimising formation of a polymer by-product.

2 cl, 1 tbl, 4 ex

FIELD: chemistry.

SUBSTANCE: disclosed catalyst systems include a chromium complex of general formula [(Ph2PXPPh2)Cr(H2O)Cl3], where X is a hydrocarbon biradical or a substituted hydrocarbon biradical, or [Ph2P(1,2-C6H4)PPh (1,2-C6H4)CH3]CrCl3 together with an activator/co-activator - methylaluminoxane/trimethylaluminium system. Components of the system are in the following molar ratio: chromium complex:MAO:TMA = 0.1%:21.4%:78.5%.

EFFECT: high selectivity of the catalyst with respect to 1-hexene while maintaining high efficiency of the catalyst system and reducing the amount of ethylene polymerisation by-products.

2 cl, 2 tbl, 8 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing aliphatic carboxylic acids C7 (n-C6H13COOH, n-heptanoic (enanthic) acid), C9 (n-C8H17COOH, n-nonanoic (pelargonic) acid) and C11 (n-C10H21COOH, n-undecanoic (undecylic) acid) via catalytic oxidation of corresponding alpha-alkenes. The method of producing aliphatic carboxylic acids is carried out by oxidising the corresponding alkenes with hydrogen peroxide solution in a two-phase system in the presence of a catalyst. The process is carried out in the presence of a metal complex catalyst of general formula Q3{PO4[W(O)(O2)2]4}, where: Q is quaternary ammonium cation [(R1)3NR2]+, where: R1, R2 contain 1 to 16 carbon atoms, or of formula [C5H5N(n-C16H33)]3{PO4[W(O)(O2)2]4}.

EFFECT: high output and selectivity of the desired aliphatic carboxylic acid.

6 cl, 12 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: catalytic system of ethylene in 1-hexene trimerisation includes a chromium (III) complex with a diphosphoric ligand of the general formula [CrCl3[(Ph2P(1,2-C6H4)P(Ph)(1,2-C6H4)(R)](THF)], where R is a hydrocarbon radical or a heteroatom-containing hydrocarbon group, which is in a phenyl substituent in the ortho-position relative to one of the phosphorus atoms. A source of chromium (III) is represented by tris(tetrahydrofuran)chromium chloride, and an activator, representing a mixture of solutions of trimethylaluminium and partially hydrolysed trimethylaluminium in toluene or methylcyclohexane. The molar ratio of the catalytic system components [Cr] : partially hydrolysed trimethylaluminium : trimethylaluminium constitutes 0.03-1.09%:6.95-31.92%:67.39-92.81%.

EFFECT: obtaining high selectivity by 1-hexene with the simultaneous reduction of the quantity of ethylene polymerisation byproducts in the process of trimerisation.

2 cl, 2 tbl, 19 ex

FIELD: chemistry.

SUBSTANCE: catalytic complex of selective ethylene in 1-hexene trimerisation includes: a chromium (III) compound with a diphosphine ligand of the general formula [CrCl3((Ph2P(1,2-C6H4)P(Ph)(1,2-C6H4)CH=CH2)-(L)], where L - tetrahydrofuran or water, chloride of tris(tetrahydrofuran)chromium is applied as a chromium (III) source, a solution of methylalumoxane is applied as an activator, with the complex components being in the following molar ratio: chromium compounds: activator= 0.02-0.12%:99.88-99.98%.

EFFECT: high productivity of selective ethylene trimerisation.

2 tbl, 11 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing an ethylene trimerisation catalyst ligand. Described is a method of producing a ligand of a catalyst for trimerisation of ethylene to 1-hexene of general formula: where R is alkyl, R1-7 is hydrogen and/or alkyl, involving a reaction for synthesis of 2-(alkylthio)alkylamine and 2-(alkylthio)alkylketone or alkylthioalkanal, where the alkyl in the alkylthio substitute is octyl, and the alkyl in alkylamine and alkylketone is CH3, C2H5, in the presence of titanium tetraisopropoxide in toluene medium at temperature of 50-80°C, with subsequent addition of ethanol and tetrahydrofuran, cooling the obtained solution to 2-0°C, subsequent addition of sodium borohydride and hydrochloric acid using the following formula: wherein alkylthioalkanal is selected from a group comprising: 2-(octylthio)-2-methylpropanal, 2-(octylthio)butanal, 2-(octylthio)pentanal, 2-(octylthio)hexanal, 2-(octylthio)heptanal, 2-(octylthio)octanal, 2-(octylthio)nonanal, 2-(octylthio)decanal.

EFFECT: method provides toxic and environmental safety when producing the ligands.

1 tbl, 14 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of maintaining stable catalytic activity during tetramerisation of ethylene and a method of producing 1-octene via tetramerisation of ethylene. Tetramerisation is carried out in the presence of a catalyst system containing chromium or a chromium precursor, alkylaluminoxane and a ligand with the backbone structure P-C-C-P, of formula 1, where R1, R2, R3 and R4 each independently denotes phenyl or substituted phenyl and R1, R2, R3 and R4 each does not have substitutes on atoms neighbouring atoms bonded with P atoms, and R5, R6 denote a methyl group.

EFFECT: disclosed methods enable stable sustenance of catalytic activity compared to ordinary catalyst systems.

2 cl, 2 dwg, 2 tbl, 17 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to a catalyst composition and a method for di-, tri- and/or tetramerisation of ethylene. The catalyst composition contains a chromium compound, a ligand of general formula (A) R1R2P-N(R3)-P(R4)-N(R5)-H or any cyclic derivatives (A). At least one of P or N atoms in the PNPN group is a member of a ring system, where that ring system is formed from one or more component compounds of structures (A) through substitution, and a cocatalyst or activator. The method and composition enable to produce 1-hexene with a long cycle of active operation of the catalyst and high selectivity. No broad distribution of the obtained LAO is observed and formation of polymers is well suppressed.

EFFECT: ensuring high purity of the product without additional purification steps at the extraction line.

17 cl, 2 ex, 1 tbl, 1 dwg

FIELD: chemistry.

SUBSTANCE: catalyst system for selective oligomerisation of ethylene, which contains a ligand in a P-C-C-P skeleton of formula 1, 2, 3 or 4, a chromium or molybdenum or tungsten compound and a promoter. Described also are a method of producing 1-hexene via selective trimerisation of ethylene and a method of producing 1-octene via selective tetramerisation of ethylene using said catalyst system. Catalyst activity is stable for a period of time sufficient for maintaining reaction rate constant. [Formula 1] (S,S)-enantiomer, [Formula 2] (R,R)-enantiomer, [Formula 3] (R,R)-1,2-trans-diphosphine enantiomer, [Formula 4] (S,S)-1,2-trans-diphosphine enantiomer.

EFFECT: method of producing 1-octene via selective tetramerisation of ethylene.

7 cl, 4 tbl, 50 ex

FIELD: chemistry.

SUBSTANCE: method relates to production of acetic acid ether (methyl acetate) via carbonylation of dimethyl ether in gas phase in presence of catalyst and may be used in chemical industry. Invention covers catalyst for carbonylation of dimethyl ether that comprises acid cesium salt of phosphor-tungsten heteropoly acid CsxHyPW12O40, where 1.3≤x≤2.2, y=3-x with platinum additive in amount of 0.25-1.0 wt %. Catalyst in prepared on adding cesium soluble salt to mix of solutions of phosphor-tungsten heteropoly acid and platinum-hydrochloric acid, both taken in required ratio, evaporating, drying, tabletting and grinding to required size. Invention covers also production of methyl acetate in presence of above described catalyst.

EFFECT: higher catalytic activity.

5 cl, 9 ex, 1 tbl

FIELD: polymerization catalysts.

SUBSTANCE: supported olefin trimerization and oligomerization catalyst is characterized by molar productivity equal to 50% of that shown by the same but non-supported catalyst. Catalyst comprises: source of transition group 6 metal; ligand depicted by formula (R1)(R2)X-Y-X(R3)(R4) or X(R1)(R2)(R3), wherein X represents phosphorus, arsenic, or antimony atom, Y is linking group, and each of R1, R2, R3, R4, independently of each other, represents optionally substituted hydrocarbon group, optionally substituted heterohydrocarbon group, wherein each of the formulas has polar substituent, which is other than phosphane, arsane, or stibane group; and optionally activator. Polymerization of olefins or olefin blends is an integrated process in one or different reactors, in particular olefin monomer or olefin blend is brought into contact with above-described catalyst under trimerization conditions and then with additional catalyst suitable for olefin polymerization, which results in that trimerization products are incorporated into higher-molecular weight polymer. Process may be accomplished in a reaction circuit. Invention also claims supported α-olefin trimerization and polymerization catalyst comprising above-indicated components and optionally one or several olefin polymerization suitable catalysts.

EFFECT: excluded loss of catalyst activity in supported form.

36 cl, 25 ex

FIELD: chemistry.

SUBSTANCE: method relates to production of acetic acid ether (methyl acetate) via carbonylation of dimethyl ether in gas phase in presence of catalyst and may be used in chemical industry. Invention covers catalyst for carbonylation of dimethyl ether that comprises acid cesium salt of phosphor-tungsten heteropoly acid CsxHyPW12O40, where 1.3≤x≤2.2, y=3-x with platinum additive in amount of 0.25-1.0 wt %. Catalyst in prepared on adding cesium soluble salt to mix of solutions of phosphor-tungsten heteropoly acid and platinum-hydrochloric acid, both taken in required ratio, evaporating, drying, tabletting and grinding to required size. Invention covers also production of methyl acetate in presence of above described catalyst.

EFFECT: higher catalytic activity.

5 cl, 9 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: catalyst system for selective oligomerisation of ethylene, which contains a ligand in a P-C-C-P skeleton of formula 1, 2, 3 or 4, a chromium or molybdenum or tungsten compound and a promoter. Described also are a method of producing 1-hexene via selective trimerisation of ethylene and a method of producing 1-octene via selective tetramerisation of ethylene using said catalyst system. Catalyst activity is stable for a period of time sufficient for maintaining reaction rate constant. [Formula 1] (S,S)-enantiomer, [Formula 2] (R,R)-enantiomer, [Formula 3] (R,R)-1,2-trans-diphosphine enantiomer, [Formula 4] (S,S)-1,2-trans-diphosphine enantiomer.

EFFECT: method of producing 1-octene via selective tetramerisation of ethylene.

7 cl, 4 tbl, 50 ex

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