- PROCESS IMPROVEMENTS IN THE ELECTROCHEMICAL FLUORINATION OF OCTANOYL CHLORIDE
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The electrochemical fluorination of octanoyl chloride to produce perfluorooctanoyl fluoride in anhydrous hydrogen fluoride was investigated.The study was carried out in a microprocessor-aided modified Simons reactor system using a Cu/CuF2 reference electrode.The formation of polymeric tar at the anode surface was limited by the addition of a mercaptan compound and by constant current density operation.Continuous operation was achieved through frequent additions of a solution of hydrogen fluoride and reactant.Conversion of reactant to perfluorinated products was improved to 80 percent with good selectivity.Experimetnal results of this investigation are presented and discussed.
- Prokop, H. W.,Zhou, H-J.,Xu, S-Q.,Wu, C-H.,Chuey, S. R.,Liu, C. C.
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- EINSTUFIGE HERSTELLUNG HALOGENIERTER CARBONSAUREFLUORIDE AUS DEN FREIEN SAUREN
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The reaction of per- or polyhalogenated carboxylic acids with trifluoromethyl or difluorochloromethyl substituted aromatics takes place in the presence of Lewis-acid-catalysts and forms the corresponding acid fluorides in good to very good yields.
- Schwertfeger, W.,Siegemund, G.
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- A full-fluorine octanoyl fluorine preparation method (by machine translation)
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The invention relates to a preparation method of the whole fluorine octanoyl fluorine, fluorine gas diluted by inert gas under low temperature conditions with the caprylyl chloride reaction to prepare the full fluorine octanoyl fluorine. The method of the invention through the inert gas dilution, reduce the reaction temperature, by adding the agitation or filler such as fluorine gas with the technical means caprylyl chloride reaction is more moderate, uniform, easy to control, and greatly improves the yield of the whole fluorine octanoyl fluorine, and prevents the use of the metal anode of the electrolytic cell, substantially eliminates the generation of solid waste material. Fluorine gas with the caprylyl chloride direct reaction can have to avoid the waste of energy, and improve the yield of the fluorine octanoyl fluorine, reduce long chain carbon atom chain reaction produces by-products such as low fluorine carbon, ensure the quality of the product fluorine octanoyl fluorine, perfluorooctanoic acid production enterprises for a significant meaning. (by machine translation)
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Paragraph 0021-0034
(2017/08/19)
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- PROCESSES FOR PRODUCTION OF FLUORINE-CONTAINING COMPOUNDS
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This process for producing fluorine-containing compounds includes liquid-phase fluorination by introducing a raw material compound and fluorine gas into a solvent to replace hydrogen atoms in the raw material compound with fluorine atoms. More specifically, the process for producing fluorine-containing compounds includes (1) promoting fluorination by dissolving the raw material compound in anhydrous hydrofluoric acid and introducing into a liquid-phase fluorination solvent, or (2) promoting fluorination by dissolving the raw material compound in a perfluoro compound having a plurality of polar groups in a molecule thereof and introducing into a liquid-phase fluorination solvent. According to these processes, a fluorination reaction can be carried out at high yield and without containing hardly any isomers while using a hydrocarbon compound as is for the raw material.
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Page/Page column 12
(2010/09/05)
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- A Lewis acid catalytic process for preparing fluorocarboxylic acid halides
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Selected Group III and Group V Lewis acids were found to catalyze the isomerization and rearrangement of halosulfonyldifluoromethyl group (Rf-CF2SO2X, where X is either chlorine or fluorine) to form fluorocarboxylic acid halides (RfCOX). Fluorodesulfoxylation of the halosulfonyldifluoromethyl group yielded SOF2 as one of the two sulfur-containing oxides. Product analysis would suggest that both Lewis acid catalyzed and halogen exchange reactions are occurring and are dependent upon the starting halosulfonyldifluoromethyl material and Lewis acid.
- Behr,Cheburkov
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p. 369 - 372
(2007/10/03)
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- 1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine: A new selective fluorinating agent
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The title compound has been prepared in 96-98% yield by the reaction of tetrafluoroethylene and dimethylamine. 1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine (1) is found to be an effective reagent for the conversion of alcohols into alkyl fluorides. Reaction of 1 and primary alcohols proceeds with high yield formation of the corresponding alkyl fluorides at elevated temperature. However, the reaction of secondary and tertiary alcohols rapidly takes place at 0-10°C, producing corresponding alkyl fluorides as major product along with some olefins.
- Petrov,Swearingen,Hong,Chris Petersen
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- Ozonides of perfluorooct-1-ene and perfluorooct-2-ene
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Ozonides of higher perfluoroalkenes were prepared for the first time by ozonation of perfluorooct-1-and -2-enes in Freon-113. The structures of the resulting compounds were confirmed by 13C NMR spectroscopy and GLC-mass spectrometry.
- Odinokov,Akhmetova,Savchenko,Bazunova,Paramonov,Khalilov
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p. 1103 - 1105
(2007/10/03)
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- Yield improvement in the electrochemical production of pefluorooctanoic acid
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The possibility of obtaining real yield improvements in the industrial electrochemical production of perfluorooctanoic acid is discussed on the basis of recent experimental data obtained using perfluorohexyl acetyl chloride in place of octanoyl chloride as a starting material.In particular, the effect of the non-formation of cyclic byproducts on the yield of perfluoro-octanoic acid has been examined, as well as considering previous results obtained starting from a different partially fluorinated precursor, 4-perfluorobutyl butanoyl chloride.The yield of perfluoro-octanoic acid from perfluorohexyl acetyl chloride was less than expected, because of an accompanying increase in perfluoro-n-heptane formation.
- Napoli, M.,Scipioni, A.,Gambaretto, G. P.,Carlini, F. M.,Bertola, M.
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p. 261 - 264
(2007/10/02)
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- AMINE(POLYFLUOROALKOXYACYL)IMIDE SURFACTANTS
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Twenty-one examples (10a-d, 11a-l and 12a-e) of a new class of surfactants, the amine(polyfluoroalkoxyacyl)imides, were prepared by the reaction of esters containing polyfluoroalkoxy groups with tertiary alkylaminimides and hydroxyalkylaminimides.Included are five examples of difunctional aminacylimides that contain the hydrophilic portion of the molecule in the middle.These new surfactants are among the most potent known in their ability to form aqueous solutions with very low surface tensions and can be used to prepare stable emulsions of perfluorodecalin in water.Two new esters (ethyl perfluorooctyloxyacetate, 7, and ethyl 1H,1H-perfluorooctyloxyacetate, 9) used as intermediates to the surfactants were prepared by the alkylation of perfluoro- and 1H,1H-perfluorooctanol salts with ethyl bromoacetate.Other esters used in the preparation of the surfactants were derived from oligomers of hexafluoropropene oxide.
- Haywood, Lisa,McKee, Sean,Middleton, W. J.
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p. 419 - 431
(2007/10/02)
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- ELECTROCHEMICAL FLUORINATION OF 4-(PERFLUORO-n-BUTYL)-n-BUTANOYL CHLORIDE
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Electrochemical fluorination of 4-(perfluoro-n-butyl)-n-butanoyl chloride produces perfluorooctanoyl fluoride in higher yields than those obtained from n-octanoyl chloride, which is the usual starting material.In particular, one of the by-products of the industrial process, the cyclic perfluoroether perfluoro-2-propyl-tetrahydropyran, is not formed.Also the other by-products, except fluorocarbon perfluoro-n-heptane, are produced in lower amounts.These results are discussed and a mechanism is suggested.
- Napoli, M.,Conte, L.,Gambaretto, G. P.,Carlini, F. M.
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p. 213 - 224
(2007/10/02)
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- ANALYSIS OF THE PRODUCTS FROM THE ELECTROCHEMICAL FLUORINATION OF OCTANOYL CHLORIDE
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The perfluorinated products from the electrochemical fluorination of octanoyl chloride were analyzed using several techniques.Cappillary gas chromatography was used for quantitative analysis of the desired product, perfluorooctanoyl fluoride, and for perfluorinated cyclic ether by-products.Isopropyl ether was an effective solvent, and ethylbenzene served as an internal standard.Acidimetric titration was used to qualify the amount of acid derivative products present in the sample.Since the products have limited solubility in water, alternative solvents were developed.Taking advantage of the facile hydrolysis of the acyl fluoride product, the perfluorinated acid was isolated.Details of the application of these chemical techniques to perfluorinated products and the corresponding results will be discussed.
- Prokop, H.W.,Zhou, H-J,Xu, S-Q,Wu, C-H,Liu, C. C.
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p. 277 - 290
(2007/10/02)
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- ELECTROCHEMICAL FLUORINATION USING POROUS NICKEL AND FOAM NICKEL ANODES
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This work set out to examine the reasons behind some of the problems associated with ECF, namely, lack of reproducibility, low chemical yields, poor selectivity and low current densities, with a view to ameliorating these shortcomings and making the process more attractive to the chemical industry.The approach was to study the chemistry under controlled conditions of potential, reactant concentration, temperature, etc., and to analyse the results in terms of product structure, distribution and yield.Two distinct stages in the process were identified, i) the conditioning of the electrode, and, ii) the fluorination of the organic substrate.These stages are described in detail in relation to two model systems investigated, the fluorination of propene using porous and foam nickel anodes, and the fluorination of the octanoyl chloride using nickel foam anodes.The scales of experiments ranged from 100 ml to 100 l cell capacities.General conclusions are derived and recommendations made for the more efficient operation of the process.
- Drakesmith, F. G.,Hughes, D. A.
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p. 103 - 134
(2007/10/02)
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- THE FACILE PREPARATION OF HF FREE POLYFLUORINATED ACYL FLUORIDES
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The reaction of polyfluorinated acids with the Ishikawa Reagent (FAR) in the presence of NaF gives 59 - 91 percent isolated yields of HF free polyfluorinated acyl fluorides.The reaction is rapid, safe, easily scaled up, and amenable to a one-pot procedure.
- Cox, Daryl G.,Sprague, Lee G.,Burton, Donald J.
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p. 383 - 388
(2007/10/02)
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- THE ELECTROCHEMICAL FLUORINATION OF OCTANOYL FLUORIDE WITH ELECTROLYTE CIRCULATION
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A modification to the standard method of electrochemical fluorination is described which embodies a forced flow of electrolyte through the electrode pack.A preliminary study of flow characteristics through an electrode pack was carried out.Good yields of perfluorooctanoyl fluoride and associated perfluorinated products are reported.The nature of the anode surface was studied before and after fluorination by scanning electron microscopy.
- Lines, D.,Sutcliffe, H.
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p. 423 - 440
(2007/10/02)
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