354-14-3Relevant academic research and scientific papers
Catalytic Liquid-phase Fluorination of Tetrachlorethene (PCE) with Titanium Antimony Mixed Halides
Batiot, Catherine,Brunet, Sylvette,Barrault, Joel,Blanchard, Michel
, p. 867 - 868 (1994)
A new catalyst consisting of a TiCl4-SbCl5 mixture with a molar composition Sb : Ti = 4 : 1 makes possible the fluorination of tetrachlorethene with liquid HF at 90 deg C.
METHOD FOR PRODUCING 1,1,2-TRICHLORO-2-FLUOROETHENE (TCFE) AND APPLICATION THEREOF
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Paragraph 0015; 0017-0018, (2021/02/19)
To provide a novel method capable of efficiently producing 1,1,2-trichloro-2-fluoroethene (TCFE) and to provide a novel application of TCFE.SOLUTION: There are provided: a method for producing 1,1,2-trichloro-2-fluoroethene (TCFE) which comprises a) a step of fluorinating pentachloroethane at a temperature of 0 to 80°C to generate monofluoropentachloroethane and b) a step of reacting the monofluoropentachloroethane obtained in the step a) with zinc to generate TCFE; and a use of a composition comprising TCFE as a solvent or a detergent.SELECTED DRAWING: None
Examples of catalytic and selective routes for fluorinated building blocks
Brunet, Sylvette
, p. 1067 - 1071 (2014/11/27)
Examples are presented for the catalytic fluorination of chlorinated starting materials in order to produce building blocks or HFCs. The fluorination of CF3CH2Cl, of CCl2=CCl2, of trichloromethoxylbenzenes and trichloromethoxybenzene involving nucleophilic substitution are reported. In all cases, HF was the fluorinating agent. Depending on the chlorinated substrate and the degree of fluorination required, liquid- or gas-phase processes were involved. Usually, catalysts were SbCl 5 in liquid phase and chromium oxide in gas phase. In the presence of SbCl5, at 90 °C under an initial pressure of 10 bar, the fluorination of CCl2=CCl2 leads mainly to the formation of CClF2CHCl2, and the active catalyst is an antimony mixed halide (SbCl3F2). In the same way, the presence of SbCl5 favored the formation of 1-trifluoromethyl-3- trichloromethylbenzene from bis-1,3-trichloromethylbenzene at low temperature (50 °C) and in the presence of a low amount of HF. Moreover, trichloromethoxybenzene was totally transformed into trifluoromethoxybenzene. At 380 °C and at atmospheric pressure, the transformation of CF 3CH2Cl into CF3CH2F was favored over chromium oxide-based catalyst modified by zinc (corresponding to a (Zn/Zn + Cr) molar ratio of 0.22).
PROCESS FOR PRODUCING PENTAFLUOROETHANE
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Page/Page column 2-3, (2010/08/22)
The present invention relates to a process for producing pentafluoroethane. More particularly, the subject of the invention is a continuous process for producing pentafluoroethane comprising (i) a step of fluorinating perchloroethylene (PER) with hydrofluoric acid, in the gas phase, in the presence of a catalyst, (ii) a step of separating the products issuing from step (i) in order to give a fraction of light products and a fraction of heavy products, comprising hydrofluoric acid, unreacted perchloroethylene and under-fluorinated products, and (iii) a step of pretreating the fraction of heavy products before recycling to step (i).
PROCESS FOR THE PRODUCTION OF FLUORINATED HYDROCARBONS
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Page column 10, (2008/06/13)
A process of exchanging at least one heavier halogen in a halogenated hydrocarbon is described. It comprises reacting a perhaloethylene or pentahaloethane, with at most three fluorine atoms with anhydrous hydrofluoric acid in the liquid phase in the presence of an antimony halogenide, the reaction being carried out in a substantially inert vessel.
Synthesis of 1,1,1-trifluoroethane by fluorination of 1-chloro-1, 1-difluoroethane
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Example 1, (2008/06/13)
The subject of the invention is the manufacture of 1,1,1-trifluoroethane by fluorination or 1-chloro-1,1-difluoroethane with anhydrous hydrofluoric acid. The reaction is carried out in the liquid phase and in the presence of a fluorination catalyst.
NUCLEOPHILIC REACTIONS AT A VINYLIC CENTER. XXVIII. FLUOROCHLOROETHENES AND FLUOROBROMOETHENES IN REACTIONS WITH SODIUM ALCOHOLATES AND ARENETHIOLATES
Shainyan, B. A.,Vereshchagin, A. L.
, p. 1981 - 1988 (2007/10/02)
During the reaction of halogenoethenes (Z+E)-CHX=CFX with sodium methoxide and with sodium p-thiocresolate in methanol initial attack by the nucleophilic takes place at the carbon atom attached to the fluorine atom.In the reactions with sodium methoxide the intermediate monosubstitution products are more reactive than the initial halogenoethenes, and the main reaction products are the ortho esters CHXYC(OMe)3.An "element effect", i.e., concurrent substitution of F and Cl(Br) in the reaction with sodium methoxide, was discovered.With sodium p-thiocresolate trifluorochloroethene gives the product from substitution of the chlorine atom and a small amount of the addition product as impurity.The other ethenes give substitution, addition, and halogenophilic reduction products and also the products from further transformations (hydrolysis and decarboxylation).
REACTION OF ORGANIC COMPOUNDS WITH SF4-HF-HALOGENATING SYSTEM VII. REACTIONS OF OLEFINS WITH THE SF4-HF-Cl2(Br2) SYSTEM
Kunshenko, B. V.,Mokhamed, Nagib Mukhtar,Omarov, V. O.,Muratov, N. N.,Yagupol'skii, L. M.
, p. 511 - 518 (2007/10/02)
Under the influence of the SF4-HF-Cl2(Br2) system halogen-containing olefins undergo conjugate halogenofluorination.It was shown for the case of (Z)- and (E)- 1,2-dichloroethenes that these reactions take place anti-stereospecifically through the formation of the bromonium ions.The accumulation of chlorine atoms in the olefin molecule hinders electrophilic addition of stoichiometric equivalents of ClF and BrF at the double bond.The SF4-HF-Br2 system is an effective agent for substitutive fluorination of organic compounds containing bromine.Only the bromine atoms situated at the secondary carbon atom are substituted by fluorine.
REACTIONS OF CHLORINE MONOFLUORIDE. IV. ADDITION OF CHLORINE MONOFLUORIDE TO HALOGEN-SUBSTITUTED ALKENES
Boguslavskaya, L. S.,Chuvatkin, N. N.,Panteleeva, I. Yu.
, p. 1832 - 1842 (2007/10/02)
The reactions of chlorine monofluoride with halogenoethylenes (1,1-dichloro-, 1,2-dichloro-, trichloro-, and tetrachloroethylenes) and halogenopropenes ( 3-bromo-, 3,3,3-trichloro-, E- and Z-1,3-dichloro-, 3-chloro-2-methyl-, and perfluoropropenes) were investigated in inert solvents in the presence of ethyl acetate as external nucleophile.In all cases chloroacyloxy adducts were isolated and identified in addition to the chlorofluorination products, and this indicates an electrophilic mechanism for the chlorofluorination of polyhalogenoalkenes.Methyl chloromaleate, chlorofumarate, chlorofluoroethylenedicarboxylate, α,β-difluoroacrylate, and perfluoromethacrylate in anhydrous hydrogen fluoride form the corresponding chlorofluoro adducts with satisfactory yields, whereas the reaction takes place with difficulty in inert solvents.
REACTIONS OF CHLORINE MONOFLUORIDE. SUBSTITUTION OF CHLORINE ATOMS BY FLUORINE IN CHLORINE-SUBSTITUTED ALKANES AND ESTERS
Chuvatkin, N. N.,Panteleeva, I. Yu.,Boguslavskaya, L. S.
, p. 821 - 827 (2007/10/02)
In anhydrous hydrogen fluoride under mild conditions chlorine monofluoride selectively substitutes the chlorine atoms in chlorine-substituted alkanes and esters by fluorine with the formation of high yields of the corresponding fluorides.The presence of an alkoxycarbonyl group or difluoromethylene group at the α position to the CHCl group deactivates the chlorine atom, and substitution by fluorine does not occur.In chloroalkanes, from which elimination of the chloride ion leads to sufficiently stable carbocations, substitution by fluorine can be realized in the absence of hydrogen fluoride at temperatures between -20 and -60 deg C.The fluorinating capacity of chlorine monofluoride is increased in the presence of catalytic amounts (3-5percent) of antimony pentachloride.Here the reaction is less selective than in hydrogen fluoride.In certain cases substitution is accompanied by hydride transfers.
