Organofluorine chemistry:
science, technologies, manufacture since 1987
Our Patents

RU2558147 (C1) 2015-07-27


Invention relates to chemistry of organofluoric compounds, in particular to method of obtaining methyl-2-fluoroacrylate (methyl ether of 2-fluoroacrylic acid). Methyl-2-fluoroacrylate is obtained by interaction of methyl ether of fluorodichloracetic acid, chloromethyl ether of trifluoroacetic acid and zinc in polar aprotic solvent such as dimethylformamide, N-methylpyrrolidone, N,N-dimethylurea or N,N-dimethylpropyleneurea, with simultaneous distillation of target product under reduced pressure.EFFECT: output of target product constitutes 50-60%.

RU2550139 (C1) 2015-05-10


What is presented is producing trimethyl(trifluoromethyl)silane by a reaction of trimethyl(trichloromethyl)silane with a fluorinating agent specified in: bromine activated antimony trifluoride, or antimony pentachloride activated antimony trifluoride, or gaseous hydrogen fluoride in the presence of antimony pentachloride; the reaction is carried out at heating in an inert fluorinated solvent, such as n-chlorbenzotrifluoride, or solvent-free.EFFECT: possibility to produce the high-yield compound with using no ozone-damaging freon gases and complex instrumentation.

RU2547654 (C1) 2015-04-10


Мethod consists in the reduction of hexafluoroacetone with formic acid derivatives. Hexafluoroacetone is applied in the form of its sesquihydrate and reduction is realised by the interaction of the claimed sesquihydrate with salts of formic acid at boiling and the following ratio of reagents (CFCOCF1.6HO):M(HCOO) 1:1.5-4, where M=NH, Na, K.Мethod makes it possible to obtain hexafluoroisopropanol with high output.

RU2536872 (C1) 2014-12-27


Method includes obtaining trimethylsilyl ether or bis-trimethylsilyl ether from respective fluorine-containing mono- or bi-basic aromatic acid by its interaction with trimethylchlorosilane, its conversion into respective zinc derivative resulting from reaction with zinc salt or zinc oxide in polar aprotic solvent, such as dimethylformamide, dimethylacetamide, acetonitrile, N-methylpyrollidone, oxidation of obtained zinc derivative in the same solvent with peroxy compound in presence of salts of monovalent copper CuX, where X=Cl, Br, I, and further processing with concentrated hydrochloric acid, after which target mono- or dihtdroxypolyfluorobenzene is separated by known methods. Method makes it possible to obtain target compounds with outputs.

RU2528427 (C1) 2014-09-20


Invention relates to a method of producing bromodifluoromethyl(trimethyl)silane via bromation of difluoromethyl(trimethyl)silane while illuminating with an incandescent lamp in the temperature range of 50-85°C with molar ratio of difluoromethyl(trimethyl) silane to Br2 of 1:0.7-1. The end product is separated from the reaction mixture by distillation. Output is equal to 90-95% with conversion of the starting difluoromethyl(trimethyl)silane of 60-90%. EFFECT: industrially suitable method of producing said compound with high output and easy separation of the end product.

RU2528334(C1) 2014-08-27


Invention relates to a method of obtaining 6,6,7,7,8,8,8-heptafluoro-5,5-bis(trifluoro-methyl)octadiene-1,3 from 1,1,1,3,4,4,5,5,5-nonafluoro-2-(trifluoromethyl)-pentene-2 (1) by its interaction with 1,4-dibrom-2-ene or 1,4-dichloro-2-ene with obtaining 1-bromo-6,6,7,7,8,8,8-heptafluoro-5,5-bis(trifluoromethyl)octane-2 (2a) or 1-chloro-6,6,7,7,8,8,8-heptafluoro-5,5-bis-(trifluoromethyl)octane-2 (2b). Intermediate (2a,2b) is dehydrohalogenated directly during heating with KOH in sulpholane, obtaining target 6,6,7,7,8,8,8-heptafluoro-5,5-bis(trifluoro-methyl)octadiene-1,3, separating it by distillation from the reaction mixture and fractioning with outputs of 80-85%. Application of the claimed method makes it possible to simplify the synthesis scheme and make production of the target product cheaper.

RU2527046(C1) 2014-08-27


Method comprises reacting bromopentaflurobenzene with zinc in molar ratio 1:1 in a polar aprotic solvent selected from a group comprising dimethyl formamide, dimethyl acetamide, N-methylpyrrolidone, acetonitrile in the temperature range of 30-70°C; the obtained entafluorophenyl zinc bromide solution is reacted with tert-butyl ether of peroxy acid, such as tert-butylperoxybenzoate, tertbutylperoxyacetate, tert-butylperoxytrifluoroacetate, in the presence of monovalent copper salts CuX, where X=Cl, Br, I, in molar ratio bromopentaflurobenzene : tert-butyl ether of peroxy acid : CuX of 1:1:0,1; the formed tert-butyl ether of pentafluorophenol is separated and hydrolysed by heating with concentrated hydrochloric acid; the desired pentafluorophenol is separated using known techniques with output of 75- 91%.

RU2521168 (C1) 2014-06-27

Invention relates to a method of producing polyfluoroaryl(t rimethyl)silanes of formula (I):


R = F, H, Si(CH3)3 , CH3,

by reacting fluorinated aromatic acids with trimethylchlorosilane to obtain corresponding silyl esters and then heating said esters with alkali metal halides in polar aprotic solvents to obtain fluoroaryl(trimethyl)silanes and extraction there of using known methods. Method is easy to carry out and enables to obtain various said compounds with high output from affordable industrially manufactured raw materials.

RU2497801 (C1) ― 2013-11-10


Invention relates to novel derivatives of oxaperfluoroalkylbromides of formula 1: CFO-[CFCF(CF)O]-CFCFBr, where n has values from 1 to 5. Invention also relates to method of obtaining claimed compounds.EFFECT: claimed compounds are characterised by specific density 1,79-1,81 g/cm, have high dissolving ability with respect to oxygen and can be applied as base for gas-transport compositions.

RU2503659 (C1) ― 2014-01-10


Invention relates to a method of producing oxaperfluoroalkane sulphonic acids and salts thereof of general formula CFO[CFCF(CF)O]CFCFSOR (1), where n = 0, 1 and R = H, alkali metal or ammonium cation, involving reaction of bromodifluoroacetyl fluoride with hexafluoropropylene oxide in a polar aprotic solvent to obtain a mixture of ?-bromo-oxaperfluoroacetyl fluorides of general formula BrCFCFO[CF(CF)CFO]CF(CF)COF, followed by decarbonylation thereof under the action of catalytic amounts of SbFto form oxaperfluoroalkyl bromides CFO[CFCF(CF)O]CFCFBr, where n = 0, 1, further reductive sulphodioxidation of the obtained oxaperfluoroalkyl bromides under the action of either dithionites of alkali metals or under the action of zinc and sulphur dioxide in a polar aprotic solvent, chlorination of the reaction mixture and alkaline hydrolysis of the obtained compounds to salts of oxaperfluoroalkane sulphonic acids and separation of said oxaperfluoroalkane sulphonic acids from salts thereof by reacting the latter with sulphuric acid with separation of hydrates of oxaperfluoroalkane sulphonic acids and subsequent dehydration thereof with thionyl chloride.

RU (11) 2475477 (13) C1 - 2011-12-09


Invention relates to a method of producing 2-fluorosulphonyl tetrafluoroethyl trifluorovinyl ester by reacting 2-bromotetrafluoroethyl trifluorovinyl ester with sulphur dioxide and zinc dust in an aprotic polar solvent, followed by chlorination with chlorine gas, extraction of the intermediate product - 2-chlorosulphonyl tetrafluoroethyl trifluorovinyl ester by simple layer separation. The process is carried out in molar ratio of reagents 2-bromotetrafluoroethyl trifluorovinyl ester : SO2 : Zn: Cl2 equal to 1:2-2.2:1:1.3-1.8. Fluorination of the obtained 2-chlorosulphonyl tetrafluoroethyl trifluorovinyl ester is carried out with potassium fluoride in a polar solvent at molar ratio of reagents 2-chlorosulphonyl tetrafluoroethyl trifluorovinyl ester: KF equal to 1:1.1-1.2 and at temperature of 25-30°C. Novel method of producing 2-fluorosulphonyl tetrafluoroethyl trifluorovinyl esterwith high output and purity, which can be used asmonomers for producing polymers.

RU2399624 (C1) - 2010-09-20


Invention relates to a novel method for synthesis of trimethylsilyl compounds of silicon which contain fluorinated substitutes, which are used in the pharmaceutical industry to produce different biologically active substances. The invention discloses a method for synthesis of fluorine-containing trimethylsilanes of general formula (CH3)3SiRf, where Rt=CF3, C2F5, C3F7, C4F9, EtOCCF2, MeOOCCF2, through reaction of a fluorinated halide of general formula RfX, where X=I, Br, Rf=CF3, C2F5, C3F7, C4F9, EtOCCF2, MeOOCCF2, with trimethylsilyl trifluoroacetate of general formula CF3CO2Si(CH3)3 in dimethyl formamide or dimethyl acetamide in the presence of zinc activated by copper bromide or trifluoroacetic acid. ^ EFFECT: obtaining different trimethylsilyl derivatives with a fluorinated group using technology which is simpler than existing technologies, which does not require high or very low temperature, has high rate of obtaining products and high output of products, does not require expensive additives and electrolysis conditions, and cheaper bromine derivatives of fluorine-compounds can be used.

RU2378246 (C1) - 2010-01-10


Present invention relates to a method for synthesis of 3,3,3-trifluoropropanal, which is used in production of herbicides, various pharmaceutical preparations and fluorine-containing polymers. The method involves a stage where alcohol reacts with halogenated hydrocarbon in the presence of a base, obtaining 3,3,3-trifluoromethylvinyl ether at temperature not above 50C, and a stage for hydrolysis of 3,3,3-trifluoromethylvinyl ether in the presence of sulphuric acid as a catalyst at high temperature. The halogenated hydrocarbon used at the first stage is 1,2-dibromo-3,3,3-trifluoropropane, and the alcohol used is isopropyl alcohol to obtain isopropyl-3,3,3-trifluoromethylvinyl ether, which is subjected to hydrolysis at the second stage. As a rule, the catalyst used at the second stage is concentrated sulphuric acid, and the base used at the first stage is a hydroxide of an alkali metal, selected from potassium or sodium hydroxide. ^ EFFECT: obtaining an end product with high output using cheaper starting compounds and the method does not require additional stages for purifying starting compounds.

RU2372331 (C1) - 2009-11-10


Invention relates to a method of producing di(C1-C6alkyl)aminotrifluorosulfuranes, which are thermally stable fluorinating agents and are used for substituting hydroxyl or carbonyl groups with fluorine in different organic compounds. The method involves carrying out the process in two steps. At the first step sulphur, bromine and fluoride of alkali metal are reacted in an organic solvent medium, for example acetonitrile, while heating to temperature not exceeding 60C, preferably at temperature between 50 and 55C thereby obtaining sulphur tetrafluoride, which is reacted with bis[di(C1-C6alkyl)amino]methane in chlorinated hydrocarbon medium at the second stage, while maintaining mixing temperature not exceeding 15C. ^ EFFECT: proposed method allows for high output of product and quality using a simple technique, using easily accessible reagents with low energy consumption and low labour input due to elimination of the purification step and extraction of intermediate products.

RU2368597 (C2) - 2009-09-27


Invention relates to a two-stage method of obtaining 2-(fluromethoxy)- 1,1,1,3,3,3-hexafluoroisopropane (sevoflurane) by reacting 1,1,1,3,3,3-hexafluoroisopropanol-2 with 1,3,5-trioxane or paraformaldehyde and chlorosulphonic acid, with subsequent extraction of 2-(chloromethoxy)- 1,1,1,3,3,3-hexafluoroisopropane (sevoflurane) and its treatment with a fluoride of an alkali metal (aqueous potassium fluoride solution) or ammonium in the presence of triethylamine. The process is carried out at molar ratio of reagents trioxane : 1,1,1,3,3,3-hexafluoroisopropanol-2 : chlorosulphonic acid 1 : 1.8-2.5 : 3-3.5, while stirring at temperature +5-20C, with subsequent separation and distillation of an organic layer.; Treatment with potassium fluoride is done at 72-75C, with molar ratio of components : sevochlorane : potassium fluoride : triethylamine 1 : 1 : 0.15. ^ EFFECT: simplification of the process due to prevention of formation of an intermediate aluminium hydrochloride polymer, stable output of products.

RU2359953 (C1) - 2009-06-27


Invention refers to the method for preparation of perfluoro-C4-C8alcyl halides of general formula Rf X, where Rf - perfluoro-C4-C8alcyl, X - bromine, iodine, fluorine. The process includes the following stages: a) interreaction of the corresponding perfluoro-C4-C8alcane sulphonic-acid fluoride of general formula RfSO2F with hydrazine in the medium of organic solvent at temperature not less than 50C with obtaining of the corresponding perfluoro-C4-C8alcyl sulphonyl hydrazide with formula RfSO2NHNH2 and b) interreaction of the product obtained in the stage a) with corresponding elemental halogen at heating in the medium of organic solvent at temperature range 90-120C. The preferential solvent for stages a) and b) is N-methylpirrolidone; the elemental halogen used in the stages b) is bromine or iodine. In latter case the reaction is carried out in the presence of potassium iodate. EFFECT: high yield and quality of the target product.

RU2470005 C1 - 2011-12-09


3PO3 : NH3 (1:1.2-1.3:3), with catalysis by transition metal salts. Invention enables to obtain the end product in a single step using cheap and nontoxic reactants.

RU2346924 (C1) - 2009-02-20


Invention concerns method of obtaining hexafluorisopropanol applied as solvent for some polymer materials, as valuable emulsifier and as raw material for obtaining sevoflurane, a new generation anesthetic. Method involves recovery of hexafluoroacetone by reducer. Hexafluoroacetone trihydrate is recovered by using hydrazine-hydrate as reducer at mol ration of hexafluoroacetone trihydrate to hydrazine-hydrate of 1:(1.1-1.5), with further addition of hydrogen peroxide in the form of 36-50% solution. EFFECT: obtaining pure target product at high output rate by cost-effective and simple method.

RU2230057 (C1) - 2004-06-10


Polyfluorinated alkoxypropionyl fluorides having general formula 1

where Rf represents linear or branched C1-C9,-perfluoroalkyl or C1-C9-perfluoroalkoxyalkyl, or hydrogen atom, are prepared by reaction of hexafluoropropene oxide with appropriate polyfluorocarboxyl fluoride in organic medium consisting of two components, from which one is a polar aprotic solvent, in presence of catalyst. Second component, constituting 80-90 wt % of the organic medium, is perfluorinated nonpolar solvent selected from perfluorinated cyclic C7-C11-hydrocarbons or aliphatic C6-C9-hydrocarbons capable of extracting acid fluorides I formed in reaction. Catalyst is N,N,N',N'-tetrasubstituted diaminomethane of formula:

гwhere R1-R4 represent linear or branched C1-C6-alkyl or C1-C6,-perfluoroalkyl, or radical -C2H4OH, or pairs R1 and R2 and R3 and R4, together with nitrogen atom to which they are attached, may form heterocyclic residue optionally containing one more heteroatom (oxygen) and substituted by one or several alkyl radicals. EFFECT: enabled selective preparation of desired products with high yields and enabled carrying out process under atmospheric pressure.

RU2189966 (C1) - 2002-09-27

Process for producing fluorinated aliphatic compounds. The present invention relates to a process for producing fluorinated aliphatic compounds by pyrolysis of perfluorocarboxylic acids and their derivatives-halides and esters. The pyrolysis is carried out in the presence of a catalyst consisting of a carrier most preferably selected from the series comprising active carbon, magnesium oxide, calcium oxide, barium oxide, zinc oxide, aluminum oxide, nickel oxide, oxides of silicon promoted with alkali metal halides, selected from the series comprising fluorides, chlorides bromides, iodides of sodium, potassium, rubidium, cesium, at a temperature in the range of from about 100 DEG C. to about 450 DEG C.; with producing fluorinated aliphatic compounds selected from the series comprising perfluoroolefins, polyfluoroolefins and their derivatives; ; and also in the presence additionally of hydrogen fluoride with the formation of fluorinated aliphatic compounds selected from the series comprising polyfluoroalkanes and their derivatives.

RU2189966 (C1) - 2002-09-27


Invention relates to a method of synthesis of fluorosubstituted hydrocarbons. Method is performed by catalytic pyrolysis of perfluoro- and polyfluorocarboxylic acids and their derivatives in the presence of hydrogen fluoride and a catalyst. Catalyst consists of a carrier promoted with alkaline metal halides. Activated carbon, magnesium, calcium, barium, zinc, aluminum, nickel oxide, silicon oxides are used as a carrier. Sodium, potassium, cesium or rubidium fluorides, iodides, bromides or chlorides are used as promoters. The content of alkaline metal halides in catalyst is from 20 to 50 % by weight. Pyrolysis is carried out at temperature 100-350 C. Hydrogen fluoride is taken in (1.5-2)-fold excess as measured for the parent component. EFFECT: improved method of synthesis, increased yield of polyfluoroalkanes.

RU2188187 (C2) - 2002-08-27


Invention relates to a method of decarboxylation of halide anhydrides or perfluorinated carboxylic acids esters to synthesize the corresponding perfluoroolefins or perfluoroalkylvinyl esters that are used as the parent raw for synthesis of polymeric materials with improved exploitation properties. Decarboxylation reaction of acids is carried out at temperature 100-300 C in the presence of a catalyst comprising of a carrier taken among an order including coal, magnesium oxide, calcium oxide, barium oxide, zinc oxide, aluminium oxide, nickel oxide or silicon oxide promoted with an alkaline metal halide. The content of an alkaline metal halide in the catalyst is from 20 to 50 weight %. The yield of synthesized perfluoroolefins or perfluoroalkylvinyl esters is up to 95%. Method ensures to carry out the stable process at a lower temperature. EFFECT: improved method of decarboxylation, increased yield, simplified process.

RU2182570 (C2) - 2002-05-20


Compounds synthesized in reaction of hydrodefluorination are used as intermediate substances. Hydrodefluorination reaction of CF3-group is carried out with aluminium chloride and cyclic-C5- C6 or aliphatic-C5- C12 hydrocarbon in medium of chloroorganic solvent at heating from 30 to 80 C. Method provides the selective hydrodefluorination of CF3-group in polyfluoroalkylbenzenes using low-priced and available raw. EFFECT: improved method of hydrodefluorination, decreased cost.

RU2206499 (C1) - 2003-06-20


Gaseous nitrogen trifluoride is freed of carbon tetrachloride impurities via selective adsorption of the former by dehydrated erionite at temperature between -30 and 30 C followed by displacement of carbon tetrachloride with inert gas, desorption and condensation of thus purified nitrogen trifluoride. Purity of product is 99.99% and content of CF4 is no higher than 10 ppm. EFFECT: enhanced economical efficiency and achieved easy industrial realization. Also published as EP1338558 (A2) EP1338558 (A3) US2003221556 (A1) US7022160 (B2) JP2003286013 (A) CN1459323 (A) CN1268412 (C)

RU2179548 (C2) - 2002-02-20


Invention relates to method of synthesis of perfluorinated ethers with terminal functional groups of the formula: RfO[CF(CF3)-CF2O]n-CF(CF3)-COX where Rf is C1-C8-perfluoroalkyl; n = 0-3; X is F or OH which are used as intermediate compounds for synthesis of perfluoroalkylvinyl esters, surface- active substances, chemically and thermally stable liquids, polymers. Method involves interaction of hexafluoropropene oxide with perfluorocarboxylic acid fluoroanhydride or with perfluoroketone or by oligomerization of hexafluoropropene oxide in medium of polar organic solvent in the presence of N,N',N''- hexaalkyl-substituted guanidium halogenide as a catalyst of the formula A where R-R3 means C1-C7-alkyl; X means Cl or F or its mixture with alkaline metal fluoride. The yield of synthesized perfluoroalkoxypropionyl fluorides is 87- 92%. If necessary, the latter can be converted to the corresponding carboxylic acids by interaction with water. The yield of perfluoroalkoxypropionic acids is 94-95%. EFFECT: improved method of synthesis, increased yield.

RU2164508 (C1) - 2001-03-27


Polyfluoroaromatic compounds are prepared by heating corresponding halogenated aromatics with alkali metal fluorides in presence of catalyst, in particular N,N',N"-hexasubstituted guanidinium halide. Reaction is carried out in medium composed of products of partial fluorination of initial halogenated aromatics, while desired products are continuously withdrawn. EFFECT: increased yield of desired products.

Also published as US6265627 (B1)

RU2134257 (C1) - 1999-08-10


Method is carried out using hydrogen fluoride at elevated temperature in the presence of catalyst. Catalyst is activated carbon promoted by alkali metal fluorides. Promoter is potassium or sodium or cesium or rubidium fluoride. Content of promoters varies from 0.05 to 0.5 kg per 1 of catalyst. EFFECT: increased yield of products and general purpose technology for preparing coolants.