Oxygen Containing Patents (Class 570/142)
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Patent number: 5744657Abstract: Tetrafluoroethylene and other valuable 2-carbon atom fluorocarbon is made by reacting fluorine-containing compound such metal fluoride with CO in an energized state, e.g. plasma excitation, to form a gaseous reaction mixture which is a precursor to COF.sub.2, followed by reacting this reaction mixture with carbon and quenching to obtain the desired fluorocarbon.Type: GrantFiled: December 18, 1995Date of Patent: April 28, 1998Assignee: E. I. du Pont de Nemours and CompanyInventor: James Lang Webster
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Patent number: 5728902Abstract: A method for manufacturing 1,1,1,3,3-pentafluoropropene comprises the steps of adding 2-trifluoromethyl-3,3,3-trifluoropropionic acid under the presence of metal carbonate and/or metal hydrogencarbonate in an aprotic solvent at reaction temperature particularly from 40.degree. C. to 80.degree. C., of refining resulting reaction products to obtain 1,1,1,3,3-pentafluoropropene, and further of coexisting a desiccating agent therein.According to the method, 1,1,1,3,3-pentafluoropropene can be manufactured through industrially efficient and cost-effective way using 2-trifluoromethyl-3,3,3-trifluoropropionic acid as a raw material.Type: GrantFiled: August 14, 1996Date of Patent: March 17, 1998Assignee: Daikin Industries Ltd.Inventors: Hirokazu Aoyama, Akinori Yamamoto, Noriaki Shibata
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Patent number: 5696308Abstract: A process for the production of a hydro(halo)fluorocarbon which comprises heating an .alpha.-fluoroether in the vapor phase at elevated temperature. .alpha.-fluoroethers are obtained by reacting a non-enolisable aldehyde with hydrogen fluoride to form an intermediate and reacting the intermediate with an alcohol or a halogenating agent. Novel .alpha.-fluoroethers are also provided.Type: GrantFiled: November 30, 1995Date of Patent: December 9, 1997Assignee: Imperial Chemical Industries PLCInventors: Leslie Burgess, Jane Lesley Butcher, Thomas Anthony Ryan, Peter Paul Clayton
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Patent number: 5648560Abstract: A process for preparing perhaloethers from perhaloolefins by reacting at least one fluorooxy compound R.sub.x --OF, wherein R.sub.x is a perhaloalkyl radical, with a perfluoroolefin in a liquid phase, optionally containing an organic solvent inert to the perfluoroolefin, while maintaining the temperature of the liquid phase in the range of -30.degree. to -120.degree. C. The process includes continuously feeding to the liquid phase a stream of an inert gas and a gaseous stream of the fluorooxy compound.Type: GrantFiled: December 9, 1994Date of Patent: July 15, 1997Assignee: Ausimont S.p.A.Inventors: Antonio Marraccini, Antonio Pasquale, Tiziana Fiorani, Walter Navarrini
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Patent number: 5618986Abstract: A method for producing a hydrofluorocarbon of the formula a H.sub.n R.sub.f H wherein n is 0 or 1, and when n is 0, R.sub.f is a C.sub.2-12 linear or branched polyfluoroalkyl group, and when n is 1, R.sub.f is a C.sub.2-12 linear or branched polyfluoroalkylene group, which comprises reacting an iodofluorocarbon of the formula I.sub.n R.sub.f I wherein n and R.sub.f are as defined above, with an alkali metal hydroxide under action of an alcohol mixture comprising a primary alcohol and a secondary alcohol.Type: GrantFiled: May 3, 1996Date of Patent: April 8, 1997Assignee: Asahi Glass Company Ltd.Inventors: Kazuya Oharu, Ryuji Seki, Seisaku Kumai
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Patent number: 5594159Abstract: A process is disclosed for producing 1,1,1,3,3,3-hexafluoropropane and/or 1,1,1,3,3-pentafluoropropene from (CF.sub.3).sub.2 CHCOOH and/or its water soluble salts. The process involves providing a mixture containing water and such carboxy compound(s) which has a pH of less than about 4, and reacting the mixture at a temperature of at least about 75.degree. C. Certain ether compounds may be included in the mixture along with (CF.sub.3)2 CHCOOH and/or its water soluble salts. The reaction of the carboxy (and optionally ether) compound(s) with water may be employed in connection with a process for producing tetrafluoroethylene and/or hexafluoropropylene by pyrolysis, where by-product perfluoroisobutylene is reacted with water (and optionally an alkanol) to produce (CF.sub.3).sub.2 CHCOOH (and optionally one or more ether compounds).Type: GrantFiled: April 13, 1995Date of Patent: January 14, 1997Assignee: E I Du Pont De Nemours and CompanyInventors: Scott C. Jackson, Paul R. Resnick, Steven H. Swearingen
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Patent number: 5589102Abstract: Benzene derivatives of the formula I ##STR1## in which R, A.sup.1, A.sup.2 X, L.sup.1, L.sup.2 m and n are as defined in claim are suitable as components of liquid-crystalline media.Type: GrantFiled: September 5, 1995Date of Patent: December 31, 1996Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Kazuaki Tarumi
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Patent number: 5573654Abstract: Perfluoroisobutene-MeOH adduct (2H-octafluororisobutyl methyl ether) is converted to hexafluoropropane by reaction with trialkyl amine (eg. triethyl amine) and H.sub.2 O. 1,1,1,3,3-Pentafluoropropene is also produced in lesser amounts. The electrolysis of the reaction product in anhydrous HF (at 10.degree.-50.degree. C., 0-140 kPa, and 50-300 amps/m.sup.2 anode area) yields C.sub.3 F.sub.8 and some CF.sub.3 CFHCF.sub.3 which is condensed out of a gas stream from the electrolysis cell.Type: GrantFiled: March 4, 1994Date of Patent: November 12, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: Yuri Cheburkov, John C. Hansen
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Patent number: 5557008Abstract: A one pot process for the perfluoroalkylation and/or perfluoroacyloxylation of organic substrates is provided. The process comprises contacting a substrate with a perfluoroalkanoic anhydride in the presence of an inorganic peroxygen compound at a temperature of greater than 10.degree. C. Substrates that can be perfluoroalkylated and/or perfluoroacyloxylated include alkylbenzenes, halogenated aromatic compounds, alkoxybenzenes, aryl benzenes, and aromatic and aliphatic disulphides. Preferably, the perfluoroalkanoic anhydride is trifluoroacetic anhydride and the inorganic peroxygen compound is sodium percarbonate.Type: GrantFiled: September 6, 1995Date of Patent: September 17, 1996Assignee: Solvay Interox LimitedInventors: Craig W. Jones, William R. Sanderson, John P. Sankey
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Patent number: 5545768Abstract: A process for the preparation of chlorofluoronitrobenzenes and difluoronitrobenzenes, which comprises heating dichloronitrobenzene to not more than 200.degree. C. in excess with an alkali metal fluoride having a total water content of about 0.2 to about 2.5% by weight in the presence of a quaternary ammonium and/or phosphonium salt, crown ether and/or polyethylene glycol dimethyl ether as catalyst in the absence of a solvent.Type: GrantFiled: December 22, 1992Date of Patent: August 13, 1996Assignee: Hoechet AGInventors: Theodor Papenfhus, Andreas Kanschik-Conradsen, Wilfried Pressler
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Patent number: 5506364Abstract: A process for the production of bis(fluoromethyl)ether by contacting formaldehyde with hydrogen fluoride in a reaction/distillation vessel. The reaction/distillation vessel is preferably a reaction/distillation column through which formaldehyde and hydrogen fluoride preferably flow in counter current.The bis(fluoromethyl)ether may be converted to difluoromethane, preferably by heating the bis(fluoromethyl)ether to elevated temperature in the presence of a metal, metal oxide, metal fluoride or metal oxyfluoride catalyst.Type: GrantFiled: May 5, 1994Date of Patent: April 9, 1996Assignee: Imperial Chemical Industries PLCInventors: John S. Martin, Thomas A. Ryan, Rachel A. Spooncer
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Patent number: 5504263Abstract: A process for the production of a hydro(halo)fluorocarbon which comprises heating an .alpha.-fluoroether in the vapor phase at elevated temperature. .alpha.-fluoroethers are obtained by reacting a non-enolizable aldehyde with hydrogen fluoride to form an intermediate and reacting the intermediate with an alcohol or a halogenating agent. Novel .alpha.-fluoroethers are also provided.Type: GrantFiled: May 16, 1995Date of Patent: April 2, 1996Assignee: Imperial Chemical Industries PLCInventors: Leslie Burgess, Jane L. Butcher, Thomas A. Ryan, Peter P. Clayton
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Patent number: 5495056Abstract: A process for the production of hydrofluorocarbons, in particular hydrofluoroalkanes such as difluoromethane, which comprises contacting an .alpha.-fluoro-ether, in particular a fluorinated dialkyl ether such as bis(fluoromethyl)ether in the liquid phase with a Lewis acid such as a fluoride of Nb, Sb, B, Ta, Al or Ti.Type: GrantFiled: December 12, 1994Date of Patent: February 27, 1996Assignee: Imperial Chemical Industries PLCInventors: Leslie Burgess, Thomas A. Ryan, Richard L. Powell
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Patent number: 5475165Abstract: Aryl halide, such as idodobenzene, is reacted with perfluoromethoxycarboxylate, such as CF.sub.3 OCF.sub.2 CO.sub.2 K, in the presence of CuI and an inert aprotic polar solvent to obtain trifluoromethylaryl.Type: GrantFiled: January 18, 1995Date of Patent: December 12, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Keith W. Palmer, Paul R. Resnick
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Patent number: 5463139Abstract: A composition comprising bis(fluoromethyl)ether and less than an equimolar amount of water, a process for the production of the composition comprising contacting formaldehyde with hydrogen fluoride and separating at least some of the by-product water from bis(fluoromethyl)ether, and use of the composition for the production of difluoromethane.Type: GrantFiled: June 29, 1994Date of Patent: October 31, 1995Assignee: Imperial Chemical Industries PLCInventors: Jane L. Butcher, Thomas A. Ryan, Leslie Burgess
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Patent number: 5446215Abstract: A process for the production of a hydro(halo)fluorocarbon which comprises contacting an .alpha.-fluoroether in the vapour phase at an elevated temperature with a catalyst and wherein the catalyst is treated whereby to maintain and/or restore its activity.The catalyst treatment comprises either: (i) heating the catalyst to an elevated temperature above about 250.degree. C. in the absence of an .alpha.-fluoro ether, or (ii) contacting the catalyst at an elevated temperature with an oxidising agent whilst or between the times when the .alpha.-fluoro ether is contacted with the catalyst. The catalyst may be an oxidation promoting metal, for example zinc, iron or copper, carried on a metal oxide, fluoride or oxyfluoride support.Type: GrantFiled: June 4, 1993Date of Patent: August 29, 1995Assignee: Imperial Chemical Industries PLCInventors: Malcolm R. Cook, John D. Scott
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Patent number: 5420364Abstract: Halogenated aromatic compounds are prepared by passing esters of halogenoformic acid at temperatures in the range 150.degree. to 600.degree. C. and pressures from 0.1 to 3 bar over a catalyst containing chromium, magnesium, iron, silicon and/or aluminium, wherein if Al.sub.2 O.sub.3 catalysts are used these have been activated with hydrogen halide.Type: GrantFiled: July 2, 1993Date of Patent: May 30, 1995Assignee: Bayer AktiengesellschaftInventors: Norbert Lui, Albrecht Marhold
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Patent number: 5420368Abstract: A process is disclosed for producing CF.sub.3 CH.sub.2 CF.sub.3 and/or CF.sub.3 CH.dbd.CF.sub.2 from at least one ether compound selected from the group consisting of compounds having the formula (CF.sub.3).sub.2 CHCF.sub.2 OR and compounds having the formula (CF.sub.3).sub.2 C.dbd.CFOR (wherein R is an alkyl group of the formula C.sub.n H.sub.2n+1 and n is an integer from 1 to 6) by contacting the ether compound(s) with water at an elevated temperature of at least about 75.degree. C. The reaction of ether compound(s) with water may be employed in connection with a process for producing tetrafluoroethylene and/or hexafluoropropylene by pyrolysis, where by-product perfluoroisobutylene is reacted with an alkanol to produce the ether compound (s).Type: GrantFiled: June 29, 1994Date of Patent: May 30, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Scott C. Jackson, Paul R. Resnick, Steven H. Swearingen
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Patent number: 5409625Abstract: Linear hydrofluorocarbons of the formula XCF.sub.2 (CF.sub.2).sub.n CH.sub.2 F where X is H or F, and n is 1 to 7 when X is H and 0 to 7 when X is F, are produced by a vapor phase catalytic reaction of HF with corresponding compounds of the formula XCF.sub.2 (CF.sub.2).sub.n CH.sub.2 OY where Y is --(CO)Cl or --SO.sub.2 Cl. Azeotropic compositions with HF (e.g., an azeotrope of CHF.sub.2 CF.sub.2 CH.sub.2 F and HF) are provided, and a portion of the linear hydrofluorocarbon product (e.g., a portion of the CHF.sub.2 CF.sub.2 CH.sub.2 F) may be recovered as an azeotropic composition and recycled.Type: GrantFiled: October 21, 1993Date of Patent: April 25, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Mario J. Nappa, V. N. Mallikarjuna Rao, Allen C. Sievert
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Patent number: 5386064Abstract: A process for the production of bis(fluoromethyl)ether which comprises contacting formaldehyde with hydrogen fluoride in the presence of an essentially water-immiscible solvent for the ether. The bis(fluoromethyl)ether may be converted to difluoromethane, optionally after separation from the solvent, preferably by heating the bis(fluoromethyl)ether to elevated temperature in the presence of a metal, metal oxide, metal fluoride or metal oxyfluoride catalyst.Type: GrantFiled: April 19, 1993Date of Patent: January 31, 1995Assignee: Imperial Chemical Industries PLCInventors: Duncan C. Woodcock, Brian T. Grady
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Patent number: 5354926Abstract: This invention provides a mixture of fluoroalkylated fullerene compounds, preferably perfluoroalkylated fullerene compounds, comprising the formula, (C.sub.60+2n)R.sup.1.sub.m R.sup.2.sub.b Z.sub.y, wherein R.sup.1 is a branched or straight chain hydrocarbon or aromatic hydrocarbon of from 1 to about 100 carbon atoms; R.sup.2 is a branched or straight chain fluoroalkyl group of from 1 to about 100 carbon atoms; Z is one or more selected from H, F and Cl; n is an integer from 0 to about 470; m is an integer from 0 to about 24+n; b is an integer from 1 to about 24+n; and y is an integer from 0 to about 35+n.Type: GrantFiled: February 23, 1993Date of Patent: October 11, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Paul J. Fagan, Paul J. Krusic, Edel Wasserman
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Patent number: 5349099Abstract: Disclosed is a process for preparing allylic halides of the formula I ##STR1## wherein X is Cl, Br or I, for use as intermediates in the synthesis of substituted tetrahydrofuran azole anti-fungal agents.Type: GrantFiled: December 13, 1993Date of Patent: September 20, 1994Assignee: Schering CorporationInventors: Shen-Chun Kuo, Donald Hou, Zheng-Yun Zhan
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Patent number: 5347058Abstract: Fluorinated olefins are produced by thermolysis of a silyl ester of a fluorinated aliphatic carboxylic acid in the presence of a catalyst which provides fluoride ion, such as potassium fluoride. The fluorinated olefins are useful as monomers and chemical intermediates.Type: GrantFiled: December 7, 1993Date of Patent: September 13, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventor: William B. Farnham
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Patent number: 5344998Abstract: A process for the production of bis(fluoromethyl)ether by contacting formaldehyde with hydrogen fluoride in a reaction/distillation vessel. The reaction/distillation vessel is preferably a reaction/distillation column through which formaldehyde and hydrogen fluoride preferably flow in counter current.The bis(fluoromethyl)ether may be converted to difluoromethane, preferably by heating the bis(fluoromethyl)ether to elevated temperature in the presence of a metal, metal oxide, metal fluoride or metal oxyfluoride catalyst.Type: GrantFiled: November 4, 1993Date of Patent: September 6, 1994Assignee: Imperial Chemical Industries PLCInventors: John S. Martin, Thomas A. Ryan, Rachel A. Spooncer
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Patent number: 5329054Abstract: Activated carboxylic acids and esters such as pentafluorobenzoic acid are rapidly decarboxylated in high yields by reacting the acid or ester with an alkanolamine reagent which catalyzes the reaction.Type: GrantFiled: July 19, 1993Date of Patent: July 12, 1994Assignee: Albemarle CorporationInventors: Kevin J. Theriot, Niomi L. Krzystowczyk, Yueh-Dong Chen, Edward A. Burt, Lawrence H. Shepherd, Jr.
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Patent number: 5288908Abstract: Compounds of the formula ##STR1## in which X represents hydrogen, --NO.sub.2 or --NH.sub.2 and Y represents --CH.sub.3, --COOH, --CONH.sub.2, --NH.sub.2 or --N.dbd.N--Z, in which the group --Z is ##STR2## with the proviso that if Y represents the group --N.dbd.N--Z, X is only --NO.sub.2, and if Y represents the group --CH.sub.3, X is only hydrogen, are described. A compound of the formula ##STR3## the preparation of which in a multi-stage process, in which the compounds of the general formula (I) are also obtained, is described, is preferred.The resulting 3,4'-diamino compound is suitable for the preparation of polycondensates and shaped articles, films and fibers of high heat resistance.Type: GrantFiled: July 19, 1993Date of Patent: February 22, 1994Assignee: Hoechst AktiengesellschaftInventors: Jurgen Lau, Gunter Siegemund, Freimund Rohrscheid
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Patent number: 5274190Abstract: Linear hydrofluorocarbons of the formula XCF.sub.2 (CF.sub.2).sub.n CH.sub.2 F where X is H or F, and n is 1 to 7 when X is H and 0 to 7 when X is F, are produced by a vapor phase catalytic reaction of HF with corresponding compounds of the formula XCF.sub.2 (CF.sub.2).sub.n CH.sub.2 OY where Y is --(CO)Cl or --SO.sub.2 Cl.Type: GrantFiled: May 24, 1993Date of Patent: December 28, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Mario J. Nappa, Allen C. Sievert
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Patent number: 5274189Abstract: This invention relates to a process for producing linear hydrofluorocarbons of the formula XCF.sub.2 (CF.sub.2).sub.n CH.sub.2 F, where X is H or F, and n is 1 to 7 when X is H, and n is 0 to 7 when X is F, by a vapor phase catalytic reaction of HF and phosgene or sulfuryl chloride with corresponding compounds of the formula XCF.sub.2 (CF.sub.2).sub.n CH.sub.2 OZ where Z is H or --C(O)OCH.sub.2 (CF.sub.2).sub.n CF.sub.2 X.Type: GrantFiled: May 24, 1993Date of Patent: December 28, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Mario J. Nappa, Allen C. Sievert
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Patent number: 5264094Abstract: Process for the preparation of fluorobenzenes having at least one hydrogen atom as ring substituent and, optionally, further substituents, which, independently of each other, can be chlorine, bromine, nitro, hydroxyl, C.sub.1 -C.sub.3 -alkoxy or C.sub.1 -C.sub.3 -alkyl, the number of nitro groups being not more than 2 and the number of hydroxyl groups and alkoxy groups being not more than 3 in each case, by heating the corresponding benzaldehydes, substituted by at least one flourine atom, in the presence of a catalyst, characterized in that the reaction product is immediately removed from the reaction zone.Type: GrantFiled: April 24, 1992Date of Patent: November 23, 1993Assignee: Hoechst AktiengesellschaftInventors: Frank P. Sistig, Ernst I. Leupold, Heinz Litterer
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Patent number: 5087765Abstract: In the process for preparing chlorotrifluoroethylene telomers by reaction of chlorotrifluoroethylene with CF.sub.3 CF or R.sub.x --CF.sub.2 OF (wherein R.sub.x may be also a perfluoroalkyl radical having 1 to 10 carbon atoms), the content of telomers with end groups --F is increased or mixtures of telomers containing species with end groups --Cl are obtained by adding F.sub.2, according to particular modalities, to the reaction medium.Type: GrantFiled: January 11, 1990Date of Patent: February 11, 1992Assignee: Ausimont S.r.L.Inventors: Antonio Marraccini, Antonio Pasquale, Marco Vincenti
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Patent number: 5087777Abstract: Novel partially fluorinated alkenes having the Formula: ##STR1## wherein each R is the same or different and is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, and CH.sub.3 CF.sub.2, and R' is an alkenyl or fluoroalkenyl group having 1 to 6 carbon atoms have utility as solvents in a variety of industrial cleaning applications including cold cleaning, dry cleaning, and defluxing of printed circuit boards.Type: GrantFiled: December 4, 1990Date of Patent: February 11, 1992Assignee: Allied-Signal Inc.Inventors: Chien C. Li, Kane D. Cook, Rajat S. Basu
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Patent number: 5059728Abstract: Novel partially fluorinated alkanes having the Formula: ##STR1## wherein each R is the same or different and is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, and CH.sub.3 CF.sub.2, and R' is an alkyl or fluoroalkyl group having 1 to 6 carbon atoms with the proviso that when each R is CF.sub.3, R' is not CF.sub.3 (CF.sub.2).sub.2 -, CH.sub.3 CF.sub.2 -, or CF.sub.3 have utility as solvents in a variety of industrial cleaning applications including cold cleaning, dry cleaning, and defluxing of printed circuit boards.Type: GrantFiled: June 29, 1990Date of Patent: October 22, 1991Assignee: Allied-Signal Inc.Inventors: Chien C. Li, Bernard Sukornick
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Patent number: 5057633Abstract: The invention relates to the preparation of perfluoroalkyl bromides or bromoperfluoroalkanes C.sub.n F.sub.2n+1 -Br (n=1 to 20).A perfluoroalkanesulphonyl chloride C.sub.n F.sub.2n+1 -SO.sub.2 Cl is reacted with a compound of formula: ##STR1## in which X represents a nitrogen or phosphorus atom and R.sup.1, R.sup.2, R.sup.3 and R.sup.4, which may be identical or different, each represent an optionally substituted hydrocarbon radical, it also being possible for one of these symbols to be a hydrogen atom.Type: GrantFiled: November 21, 1990Date of Patent: October 15, 1991Assignee: Societe AtochemInventors: Gilles Drivon, Pierre Durual, Elie Ghenassia
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Patent number: 5013472Abstract: New chlorotrifluoroethylene telomers and process for preparing them. Chlorotrifluoroethylene is reacted, at a temperature ranging from -100.degree. to +40.degree. C., with a fluoroxy compound of formula R.sub.x --CF.sub.2 OF, wherein R.sub.x represents among others a perhalogenated alkyl radical containing from 1 to 10 carbon atoms. There are obtained telomer mixtures having, among others, the following formulae: R.sub.x --CF.sub.2 --O--(M).sub.n --F; R.sub.x --CF.sub.2 --O--(M).sub.n --O--CF.sub.2 --R.sub.x ; R.sub.x --(M).sub.n --F; R.sub.x (M).sub.n --R.sub.x ; R.sub.x --CF.sub.2 --O--(M).sub.n --R.sub.x and F--(M).sub.n --F; wherein M is CF.sub.2 --CFCL and "N" ranges from 2 to 20. Most of these telomers are new compounds.Type: GrantFiled: December 23, 1988Date of Patent: May 7, 1991Assignee: Ausimont S.R.L.Inventors: Antonio Marraccini, Gabriele Perego, Giovanni Guastalla
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Patent number: 4996371Abstract: The present invention is directed to a method for replacing a carboxylic acid group with a fluorine group in a halogenated aliphatic carboxylic acid compound having the formula, R-COOH, to prepare a fluorinated product having the formula, R-F, wherein R is a halogenated aliphatic group including straight- and branched-chain aliphatic groups selected from the group consisting of halogenated aliphatic and alkoxy-substituted halogenated aliphatic groups, wherein the method comprises the steps of (a) reacting the halogenated aliphatic carboxylic acid compound with bromine trifluoride, and (b) recovering the fluorinated product.Type: GrantFiled: January 16, 1990Date of Patent: February 26, 1991Assignee: BOC, Inc.Inventors: Donald F. Halpern, Mark L. Robin
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Patent number: 4973762Abstract: A polyfluoroiodide is produced by reacting an acid halide of a polyfluorocarbon in a perhalogenated solvent with I.sub.2 and at least one salt selected from the group consisting of an alkali metal carbonate and an alkaline earth metal carbonate.Type: GrantFiled: June 27, 1989Date of Patent: November 27, 1990Assignee: Daikin Industries Ltd.Inventors: Takashi Tohzuka, Koji Fujiwara
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Patent number: 4968852Abstract: A novel compound, trifluoromethylbenzoyl bromide, is formed by bromination of trifluoromethylbenzoic acid with, e.g., phosphorus tribromide or by halogen exchange reaction of trifluoromethylbenzoyl chloride with bromine in the presence of a metal bromide. Decarbonylation of 2-, 3- or 4-trifluoromethylbenozyl bromide using a catalyst such as a phosphine-rhodium complex gives 2-, 3- or 4-bromobenzotrifluoride without forming isomers.Type: GrantFiled: December 28, 1989Date of Patent: November 6, 1990Assignee: Central Glass Company, LimitedInventors: Toshikazu Kawai, Hideki Oshio
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Patent number: 4956123Abstract: Fluorine-containing aromatic derivatives are produced by the reaction of di(haloacyl)peroxide represented by the general formula: ##STR1## (wherein X stands for a fluorine, chlorine, or hydrogen atom and n for an integer of the value of 1 to 10) with aromatic unsaturated monomers represented by the general formula: ##STR2## (wherein Y stands for hydrogen atom, methyl, ethyl, propyl, acetyl, propionyl, acetyloxy, propionyloxy, methoxy, ethoxy, propoxy, vinyl, isopropenyl, or nitro group, or a halogen atom, R.sup.1 for hydrogen atom, methyl, ethyl, propyl, or butyl group, R.sup.2 for hydrogen atom, methyl or phenyl group, and m for an integer of the value of 1 to 5).Type: GrantFiled: September 14, 1988Date of Patent: September 11, 1990Assignee: Nippon Oils & Fats Company, Ltd.Inventors: Hideo Sawada, Michio Kobayashi, Masato Yoshida
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Patent number: 4952708Abstract: An improved method for making biaryl compounds is disclosed, in which an aromatic acid halide having at least one strong electron-withdrawing group attached to or within the aromatic ring is reacted with at least one polysilane in the presence of an effective amount of a transition metal catalyst.Type: GrantFiled: April 3, 1989Date of Patent: August 28, 1990Assignee: General Electric CompanyInventors: Jonathan D. Rich, Terry E. Krafft, Philip J. McDermott, Tony C. Chang
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Patent number: 4937395Abstract: A process for the preparation of fluorobenzenes of the formula I ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are equal or different and represent H, F, Cl or alkyl having from 1 to 3 carbon atoms, at least one of these radicals being fluorine, and S.sup.1 and S.sup.2 being equal or different and represent H or a group reducing the electron density at the benzene nucleus, which comprises subjecting a compound of the formula II ##STR2## in which R.sup.1, R.sup.2, R.sup.3, S.sup.1 and S.sup.2 have the aforementioned meaning to a decarbonylation at a zeolite catalyst.Type: GrantFiled: July 14, 1989Date of Patent: June 26, 1990Assignee: Hoechst AktiengesellschaftInventors: Heinz Litterer, Hans J. Metz, Theodor Papenfuhs, Frank P. Sistig, Ernst I. Leupold
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Patent number: 4935564Abstract: A process for preparation of an alkyl halide, RX, from reaction between the corresponding alcohol, ROH, and a hydrogen halide, HX, which improves conversion of the hydrogen halide to the alkyl halide in a single pass through a reactor. The process comprises (A) contacting and reacting the hydrogen halide with a stoichiometric excess of the alcohol in a plug-flow reactor in which flow of a mixture comprising unreacted alcohol, unreacted hydrogen halide, the alkyl halide, and water is co-current; and (B) isolating and separating the alkyl halide.Type: GrantFiled: July 28, 1988Date of Patent: June 19, 1990Assignee: Dow Corning CorporationInventors: Timothy R. Bunce, Ronald S. Evanko, Timothy G. Hueston
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Patent number: 4922041Abstract: A method for producing trifluoroiodomethane in which a metal Mt selected from the group magnesium, zinc, cadmium, bismuth and tin is reacted in a first step (a) with a trifluorohalomethane, and the resulting reaction mixture is further reacted in a second step (b) with a component containing iodine to produce CF.sub.3 I. Compounds corresponding to the formula CF.sub.3.Zn.X.nL are also described.Type: GrantFiled: May 19, 1988Date of Patent: May 1, 1990Assignee: Kali-Chemie AGInventors: Dieter Naumann, Wieland Tyrra, Birgit Kock, Werner Rudolph, Bernd Wilkes
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Patent number: 4912269Abstract: The invention relates to the preparation of perfluoroalkyl bromides or bromoperfluoroalkanes, CnF.sub.2n+1 -Br (n=1 to 20).Gaseous hydrogen bromide is reacted with a perfluoroalkanesulphonyl chloride, C.sub.n F.sub.2n+1 -SO.sub.2 Cl, in the presence of a catalyst consisting of a tertiary amine or phosphine or a quaternary ammonium or phosphonium salt, at a temperature ranging from 80.degree. to 200.degree. C.Type: GrantFiled: June 28, 1988Date of Patent: March 27, 1990Assignee: AtochemInventors: Gilles Drivon, Pierre Durual, Bernard Gurtner, Andre Lantz
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Patent number: 4900874Abstract: A method for producing a fluorine-containing olefin represented by formula (I):Ch.sub.2 .dbd.CFR.sub.f (I)wherein R.sub.f represents a perfluoroalkyl group or a fluoroalkyl group comprising the step of contacting, at a high temperature, hydrogen gas with a 1,1-dihydro-2,2-difluoro alcohol represented by formula (II):HOCH.sub.2 CF.sub.2 R.sub.f (II)wherein R.sub.f represents a perfluoroalkyl group or a fluoroalkyl group.Type: GrantFiled: February 13, 1989Date of Patent: February 13, 1990Assignee: Daikin Industries, Ltd.Inventors: Kiyohiko Ihara, Fumihiko Yamaguchi, Shinichi Yamane
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Patent number: 4898997Abstract: These compounds have the general formula: ##STR1## wherein R and R.sup.1, which may be the same or different, are hydrogen or alkyl, preferably C.sub.1 -C.sub.4 alkyl, and X, Y and Z are each independently hydrogen, chlorine or fluorine, provided that when R, R.sup.1 and Z are hydrogen, X and Y are not both hydrogen or both fluorine, and are prepared by dehydrating an alcohol of the formula: ##STR2## by, for example, heating the alcohol in the presence of a catalytic amount of a strong acid such as p-toluenesulphonic acid and preferably in the presence of an inert solvent.The compounds are intermediate for the preparation of fungicidal compounds.Type: GrantFiled: December 20, 1988Date of Patent: February 6, 1990Assignee: Imperial Chemical Industries PLCInventors: Raymond V. H. Jones, Ian G. C. Fleming
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Patent number: 4879068Abstract: Preparation of alkyl fluoride by replacement of an aliphatic hydroxy group with fluorine. The reaction is performed by treating a sulfonyl derivative of an aliphatic hydroxy group with an inorganic fluoride in a polyglycol.Type: GrantFiled: September 30, 1986Date of Patent: November 7, 1989Inventors: Dario Chiarino, Davide Della Bella, Giancarlo Jommi, Domenico Badone, Roberto Pagliarin, Paolo Tavecchia
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Patent number: 4847442Abstract: Difluorobenzene is prepared by a multistep process involving fluorination of dichlorobenzoyl chloride to provide difluorobenzoyl fluoride, conversion thereof to difluorobenzoyl chloride, hydrogenation of this to difluorobenzaldehyde and decarbonylation of the aldehyde to difluorobenzene.Type: GrantFiled: July 18, 1988Date of Patent: July 11, 1989Assignee: Allied-Signal Inc.Inventors: David Nalelwajek, Michael Van Der Puy
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Patent number: 4751307Abstract: Disclosed are improved Wittig reaction processes wherein the Wittig reaction is conducted in an anisole containing solvent.Type: GrantFiled: February 27, 1987Date of Patent: June 14, 1988Assignee: Mallinckrodt, Inc.Inventor: Carl R. White
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Patent number: H992Abstract: Polyfluorobenzenes are prepared by the decarboxylation of polyfluorophthalic acids or polyfluorobenzoic acids, in the presence of a Cu, CuO or Cu.sub.2 O catalyst in either quinoline or N-methyl-2-pyrrolidone as a solvent.Type: GrantFiled: August 30, 1990Date of Patent: November 5, 1991Assignee: Occidental Chemical CorporationInventors: Lawrence B. Fertel, Henry C. Lin
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Patent number: RE35568Abstract: The present invention is directed to a method for replacing a carboxylic acid group with a fluorine .[.group.]. in a halogenated aliphatic carboxylic acid compound having the formula, R-COOH, to prepare a fluorinated product having the formula, R-F, wherein R is a halogenated aliphatic group including straight- and branched-chain aliphatic groups selected from the group consisting of halogenated aliphatic and .Iadd.halogenated .Iaddend.alkoxy-substituted .[.halogenated.]. aliphatic groups, wherein the method comprises the step of (a) reacting the halogenated aliphatic carboxylic acid compound with bromine trifluoride, and (b) recovering the fluorinated product.Type: GrantFiled: November 16, 1994Date of Patent: July 22, 1997Assignee: Ohmeda Pharmaceutical Products Division Inc.Inventors: Donald F. Halpern, Mark L. Robin