Haloalkyl Containing Compound Patents (Class 570/144)
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Patent number: 4849557Abstract: Trifluoromethyltoluene is obtained from a halomethylbenzotrifluoride, which is a relatively inexpensive material, by hydrogenating the halomethyl group of the starting compound to methyl group with hydrogen gas in the presence of a hydrogenation catalyst and an acid acceptor. Suitable examples of the halomethyl group to be hydrogenated are --CH.sub.2 Cl, --CH.sub.2 F, --CHClF, --CClF.sub.2 and --CF.sub.3. When the starting compound is bis(trifluromethyl)benzene, addition of either an alcohol or an alkali metal fluoride to the reaction system is effective for suppression of formation of xylene as a by-product, and xylene still contained in the reaction product can completely be removed by treatment with a sulfonating agent such as fuming sulfuric acid.Type: GrantFiled: May 12, 1988Date of Patent: July 18, 1989Assignee: Central Glass Company, LimitedInventors: Takeshi Kondo, Junji Negishi, Yoshihiko Goto, Matsue Minezaki, Toshikazu Kawai
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Patent number: 4825014Abstract: Chlorotrifluoromethylbenzene is prepared with a good yield by reacting chlorotoluene, hydrogen fluoride and chlorine in a gaseous phase in the presence of a catalyst selected from the group consisting of .alpha.-aluminum fluoride, .alpha.-aluminum fluoride carrying one or more salts of iron, bismuth, tin and lead, and chromium(III) oxide or partially fluorinated chromium(III) oxide carrying alkali metal fluoride.Type: GrantFiled: June 15, 1988Date of Patent: April 25, 1989Assignee: Daikin Kogyo Co., Ltd.Inventors: Yohnosuke Ohsaka, Heikitsu Sonoyama
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Patent number: 4822904Abstract: Perfluoroalkylaromatic compounds containing at least two carbons in the perfluoroalkyl group are prepared by reacting an aromatic bromide or iodide with a potassium perfluoroalkanoate corresponding to the formula KOOC(CF.sub.2).sub.n CF.sub.3 wherein n is an integer of at least one in the presence of cuprous iodide and a dipolar aprotic solvent.Type: GrantFiled: December 12, 1985Date of Patent: April 18, 1989Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4814482Abstract: Trifluoromethylaromatic compounds are prepared by reacting the corresponding aromatic bromide or iodide with potassium trifluoroacetate in the presence of cuprous iodide, a phase transfer agent, and a dipolar aprotic solvent.Type: GrantFiled: April 21, 1986Date of Patent: March 21, 1989Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4814522Abstract: Catalyzed halogen exchange between perhaloolefins to form products of the formulas:R.sup.1 R.sup.2 C=CR.sup.3 R.sup.8andR.sup.5 R.sup.6 C=CR.sup.7 R.sup.4wherein R.sup.1, R.sup.2, R.sup.3, R.sup.5, Rhu 6l , and R.sup.7 are individually selected from the group F, Cl, Br, C.sub.1 to C.sub.4 perfluoroalkyl, and pentafluorophenyl; or R.sup.1 and R.sup.3, R.sup.2 and R.sup.3, R.sup.5 and R.sup.7, R.sup.6 and R.sup.7 together, with the proviso that both groups are in the cis configuration, are selected from the group perfluoroalkylene of 2 to 4 carbons ando--C.sub.6 F.sub.4 (--)CF.sub.2 --,R.sup.8 =F, R.sup.4 =Cl or Br; and wherein none of the fluoroolefins simultaneously contains both Cl and Br.Type: GrantFiled: January 11, 1988Date of Patent: March 21, 1989Assignee: E. I. DuPont DeNemours and CompanyInventor: Frank J. Weigert
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Patent number: 4814480Abstract: Trifluoromethylaromatic compounds are prepared by reacting the corresponding aromatic bromide or iodide with a tetraalkylammonium trifluoroacetate in the presence of cuprous iodide and a dipolar aprotic solvent.Type: GrantFiled: April 21, 1986Date of Patent: March 21, 1989Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4808748Abstract: Trifluoromethylaromatic compounds are prepared by reacting the corresponding aromatic bromide or iodide with potassium trifluoroacetate in the presence of cuprous iodide and a dipolar aprotic solvent.Type: GrantFiled: December 12, 1985Date of Patent: February 28, 1989Assignee: Ethyl CorporationInventors: Ronny W. Lin, Robert I. Davidson
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Patent number: 4769503Abstract: A process for the preparation of 3,4-dichlorobenzotrihalides of the formula I ##STR1## where X is fluorine or chlorine, by reacting the corresponding 4-monochlorobenzotrihalides with chlorine gas in the presence of a catalytic amount of a Lewis acid, wherein the reaction mixture is recycled by means of a pump in a circulatory apparatus with static mixers and the amount of chlorine equivalent to the conversion of the corresponding 4-monochlorobenzotrihalide is introduced at 20.degree.-120.degree. C.Type: GrantFiled: August 30, 1984Date of Patent: September 6, 1988Assignee: BASF AktiengesellschaftInventors: Adolf Parg, Gerd Husslein, Gerhard Hamprecht
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Patent number: 4754084Abstract: Substituted fluorobenzenes are produced by pyrolyzing vinylfluorocyclobutanes at a temperature of 250.degree.-450.degree. C. in the presence of activated carbon or certain metal oxides or mixtures of metal oxides.Type: GrantFiled: April 1, 1987Date of Patent: June 28, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventor: Frank J. Weigert
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Patent number: 4734503Abstract: Catalytic transhalogenation of haloaromatics according to the equation:C.sub.z F.sub.a X.sub.b N.sub.e L.sub.1 +C.sub.z F.sub.c X.sub.d N.sub.e L.sub.2 .fwdarw.C.sub.z F.sub.a+1 X.sub.b-1 N.sub.e L.sub.1 +C.sub.z F.sub.c-1 X.sub.d+1 N.sub.e L.sub.2wherein:when C.sub.z is a benzene derivative, a+b=5; e=0; c+d=5; z=6;when C.sub.z is a pyridine derivative, a+b=4; e=1; c+d=4; z=5;when C.sub.z is a naphthalene derivative, a+b=7; e=0; c+d=7; z=10; andwhen C.sub.z is a biphenyl derivative, a+b=9; e=0; c+d=9; z=12;L.sub.1 and L.sub.2, alike or different, are selected from F, Cl, Br, H, CN, C.sub.n F.sub.2n+1, and C.sub.6 F.sub.5 ;X is Cl, Br, or I when C.sub.z is a benzene derivative; andn is 1 to 12. This method is a novel route to known haloaromatic compounds.Type: GrantFiled: February 7, 1986Date of Patent: March 29, 1988Assignee: E. I. Du Pont De Nemours and CompanyInventor: Frank J. Weigert
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Patent number: 4704483Abstract: A process for the preparation of 3-chloro-4-fluoro-5-nitrobenzotrifluoride and 3,4-difluoro-5-nitrobenzotrifluoride by reaction of 3,4-di-chloro-5-nitrobenzotrifluoride and 4-chloro-3,5-dinitrobenzotrifluoride, respectively, with an alkali metal fluoride.Type: GrantFiled: December 9, 1985Date of Patent: November 3, 1987Assignee: Occidental Chemical CorporationInventors: David Y. Tang, Byron R. Cotter, Fredrick J. Goetz
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Patent number: 4691066Abstract: In the preparation of m-chlorobenzotrifluoride (m-CBTF) by reaction between benzotrifluoride and chlorine gas, a combination of a chloride of a metal having a valence of 3 to 6 and a small amount of iodine is used as catalyst. Alternative to iodine use can be made of an iodide that liberates iodine in the presence of chlorine. The catalyst exhibits high selectivity for m-CBTF and is effective for increasing the ratio of m-CBTF to p-CBTF in the reaction product.Type: GrantFiled: March 11, 1985Date of Patent: September 1, 1987Assignee: Central Glass Company, LimitedInventors: Fumio Inoue, Yutaka Katsuhara, Koshi Okazaki
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Patent number: 4680406Abstract: A novel apparatus and a process for fluorinating organic compounds from halogen-containing organic compounds is disclosed.Type: GrantFiled: October 15, 1985Date of Patent: July 14, 1987Assignee: The Dow Chemical CompanyInventor: George S. Fujioka
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Patent number: 4650913Abstract: Reaction of a perfluorinated iodide with an olefin initiated by a sulfinate salt to prepare fluorinated iodide and diiodide monomers and surface active agents.Type: GrantFiled: November 29, 1984Date of Patent: March 17, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Andrew E. Feiring
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Patent number: 4649207Abstract: Derivatives of diphenylhexafluoropropane having the formula: ##STR1## where R is an unsubstituted or substituted alkylene, an epoxy, a silyl or alkoxysilyl group; and where X and Y are hydrogen or halogen. The derivatives are useful in formulating polymer structures.Type: GrantFiled: May 13, 1986Date of Patent: March 10, 1987Assignee: Hughes Aircraft CompanyInventors: Kreisler S. Y. Lau, William J. Kelleghan
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Patent number: 4631151Abstract: A fluorine-containing aromatic derivative is produced by causing a di(haloacyl)peroxide to react upon benzene, a mono-substituted benzene, naphthalene, or a mono-substituted naphthalene thereby introducing an X(CF.sub.2).sub.n -group into the benzene ring or the naphthalene ring.Type: GrantFiled: February 19, 1985Date of Patent: December 23, 1986Assignee: Nippon Oil & Fars Co., Ltd.Inventors: Michio Kobayashi, Masato Yoshida, Hideo Sawada, Hidehiko Hagii, Kazuyoshi Aoshima
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Patent number: 4607116Abstract: Provided is a process for preparing a diaryl or a mixture of diaryls represented by any or a combination of the following formulae (II), (III) and (V), characterized in that a diaryliodonium salt represented by the following formula (I) is reacted in a solvent in the presence of a transition metal catalyst and a reducing metal at a temperature in the range of room temperature to 100.degree. C.:[Ar.sub.1 -I.sup..sym. -Ar.sub.2 ]X.sup..crclbar. (I)Ar.sub.1 -Ar.sub.1 (II)Ar.sub.1 -Ar.sub.2 (III)Ar.sub.2 -Ar.sub.2 (IV)wherein Ar.sub.1 and Ar.sub.2, which may be alike or different, are each an aryl group which may have a substituent group or groups and X.sup..crclbar. is a counter ion which is inert to said reaction.Type: GrantFiled: March 8, 1984Date of Patent: August 19, 1986Assignee: Nippon Petrochemicals Company LimitedInventors: Yasuo Yamazaki, Takehiko Suzuki, Masaharu Uchiyama
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Patent number: 4587366Abstract: A process is described for preparing fluoroalkyl-substituted iodoalkanes by reacting a fluorinated alkyl iodide with a substituted or unsubstituted alkene under heat in the presence of a catalyst. The catalyst is at least one metal which, in the periodic table of the elements, has one of the atomic numbers 24 to 30, 42 to 48 or 74 to 79 and is in finely divided form. The products of the process according to the invention are addition compounds of the fluorinated alkyl iodide with the substituted or unsubstituted alkene and, in known processes, can be used as useful intermediates for preparing fluorine-containing polymers, textile finishes, fire-extinguishing agents or surfactants.Type: GrantFiled: October 19, 1984Date of Patent: May 6, 1986Assignee: Hoechst AktiengesellschaftInventor: Konrad von Werner
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Patent number: 4582948Abstract: Chloro-aromatic compounds of the formula ##STR1## wherein R is CF.sub.3, OCF.sub.3, OC.sub.2 F.sub.5, CN, NCO, or COCl, m is 0, 1 or 2; n is 0, 1 or 2; q is 1 or 2; q+m+n is less than 6; and when q is 1, m is 2; are prepared by the vapor phase chloro-denitration reaction of a chlorinating agent with a nitro-aromatic compound of the formula ##STR2## where R, m, n and q are as defined above.Type: GrantFiled: April 27, 1984Date of Patent: April 15, 1986Assignee: Occidental Chemical CorporationInventors: David Y. Tang, Byron R. Cotter, Fredrick J. Goetz
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Patent number: 4568700Abstract: There is provided a process for the production of halomethylating agents which are of low volatility; and a process for the halomethylation of aromatic substrates and aromatic polymeric substances. Among products produced from the halomethylaryl polymers there are anion exchange resins.Type: GrantFiled: August 22, 1983Date of Patent: February 4, 1986Assignee: Yeda Research and Development Co. Ltd.Inventors: Abraham Warshawsky, Abraham Deshe
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Patent number: 4560814Abstract: Disclosed is a process for alkylating halogenated and trifluoromethylated benzene compounds. In that process, an alkyl halide is reacted with a benzene compound having two or three substituents selected from the group consisting of the halogens and the trifluoromethyl group, and also having a hydrogen atom whose two ortho positions are occupied by two of the said substituents. The reaction is carried out in the presence of at least one alkali metal amide and at least one agent that complexes with the cation of the alkali metal amide.Type: GrantFiled: January 31, 1984Date of Patent: December 24, 1985Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Gerard Soula
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Patent number: 4558166Abstract: Process for the preparation of benzal chlorides from benzotrichlorides, according to which benzotrichlorides are reacted with thiols in the presence of metal salts at elevated temperatures.Type: GrantFiled: March 21, 1984Date of Patent: December 10, 1985Assignee: Bayer AktiengesellschaftInventors: Bernd Baasner, Erich Klauke
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Patent number: 4533777Abstract: A process for the preparation of an aromatic trifluoromethyl compound which comprises contacting an aromatic compound of the formula ##STR1## wherein R.sup.1 denotes hydrogen, alkyl, aryl, aralkyl, aryloxy, arylthio, polyhalogenoalkoxy or polyhalogenoalkylthio and the aromatic substituents R.sup.1 can in turn be substituted by halogen, alkyl, polyhalogenoalkyl, polyhalogenoalkoxy, polyhalogenoalkylthio, nitro, chlorocarbonyl or chlorosulfonyl, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently hydrogen, halogen or alkyl and two adjacent radicals of the group R.sup.1 to R.sup.5 can conjointly form a three-membered to five-membered alkylene radical, with carbon tetrachloride and hydrogen fluoride at a temperature in the range of 50.degree. C. to 140.degree. C. Certain new aromatic trifluoromethyl compounds which can prepared by such a process are also disclosed.Type: GrantFiled: August 13, 1979Date of Patent: August 6, 1985Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Erich Klauke
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Patent number: 4503254Abstract: A new process for preparing diphenyl derivatives of hexafluoropropane containing halogen substituents on the phenyl rings and new halogen-substituted diphenyl derivatives of hexafluoropropane prepared thereby are disclosed. The new compounds of this invention are useful as intermediates for the synthesis of high temperature polymer systems.Type: GrantFiled: March 24, 1982Date of Patent: March 5, 1985Assignee: Hughes Aircraft CompanyInventor: William J. Kelleghan
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Patent number: 4489212Abstract: Arenes are reacted with allyl chloride to produce allylarenes and 2-chloropropyl- or propenylarenes using a catalyst comprising a metal oxide substrate having tantalum (V) halide/oxide bound to the surface of the substrate.Type: GrantFiled: October 25, 1983Date of Patent: December 18, 1984Assignee: Shell Oil CompanyInventor: Thomas H. Johnson
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Patent number: 4438088Abstract: The invention disclosed herein is a method for preparing antimony trifluorodichloride whereby antimony trifluoride is dispersed in a liquid organic medium to form a slurry and contacted with chlorine. The invention further comprises a process for fluorinating a fluorinatable hydrocarbon or halocarbon whereby a fluorinatable hydrocarbon or halocarbon is contacted with the antimony trifluorodichloride prepared in the above process, and the fluorinated product is distilled off.Type: GrantFiled: March 11, 1982Date of Patent: March 20, 1984Assignee: The Dow Chemical CompanyInventor: John D. Weaver
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Patent number: 4436941Abstract: Alkylbenzotrifluorides can be isomerized in the presence of hydrogen fluoride.Type: GrantFiled: December 13, 1982Date of Patent: March 13, 1984Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Erich Klauke
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Patent number: 4423259Abstract: Novel trifluoropropyl-substituted aryl- or aralkylbenzene of the formula: ##STR1## wherein R is a not-substituted or ring-substituted phenyl-, benzyl-, phenethyl- or alpha-methylbenzyl group by one 3,3,3-trifluoropropyl group, and n is an integer of 1,2 or 3, provided that the total number of 3,3,3-trifluoropropyl group of the above-mentioned trifluoropropyl-substituted aryl- or aralkylbenzene is at most 3, and a process for producing thereof are disclosed.Type: GrantFiled: February 10, 1982Date of Patent: December 27, 1983Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Yoshiro Kobayashi, Itsumaro Kumadaki, Masaaki Takahashi, Takashi Yamauchi
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Patent number: 4405824Abstract: Novel trifluoropropyl-substituted aryl- or aralkylbenzenes of the formula: ##STR1## wherein R is a not-substituted or ring-substituted phenyl-, benzyl-, phenethyl- or alpha-methylbenzyl group by one 3,3,3-trifluoropropyl group, and n is an integer of 1, 2 or 3, provided that the total number of 3,3,3-trifluoropropyl group of the above-mentioned trifluoropropyl-substituted aryl- or aralkylbenzene is at most 3, and a process for the production thereof are disclosed.Type: GrantFiled: February 10, 1982Date of Patent: September 20, 1983Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Yoshiro Kobayashi, Itsumaro Kumadaki, Masaaki Takahashi, Takashi Yamauchi
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Patent number: 4400563Abstract: A process for preparing perfluoro(lower)alkylbenzenes and derivatives thereof which comprises contacting a lower alkylbenzene or the corresponding derivative with hydrogen fluoride in the presence of chlorine in the gaseous phase at an elevated temperature to give the corresponding perfluoro(lower)alkylbenzene or its derivative thereof.Type: GrantFiled: June 20, 1979Date of Patent: August 23, 1983Assignee: Daikin Kogyo Co., Ltd.Inventors: Yohnosuke Ohsaka, Uji Hiramatsu, Toshihide Honda
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Patent number: 4396785Abstract: Novel 3,3,3-trifluoropropyl derivatives of naphthalene or methylnaphthalene of the general formula ##STR1## wherein R.sup.1 and R.sup.2 respectively represent hydrogen atom or methyl group, with the proviso that R.sup.1 and R.sup.2 do not simultaneously represent methyl group; m and n respectively represent zero or 1, with the proviso that the sum of m and n is 1, and a process for preparing the derivatives are disclosed. The derivatives are suitable as a dielectric material.Type: GrantFiled: August 7, 1981Date of Patent: August 2, 1983Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Yoshiro Kobayashi, Itsumaro Kumadaki, Masaaki Takahashi, Takashi Yamauchi
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Patent number: 4374291Abstract: Bis(ethynylphenyl) compounds are prepared by an improved synthesis process which increases yield and is suitable for large scale synthesis operations. Aromatic dianilines are diazotized to form aromatic halides that are subsequently coupled with an end-protecting group having acetylenic moieties. The end-protecting groups are subsequently removed leaving the desired diethynyl derivative in quantitative yields.Type: GrantFiled: November 6, 1981Date of Patent: February 15, 1983Assignee: Hughes Aircraft CompanyInventor: Kreisler S. Y. Lau
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Patent number: 4367350Abstract: A process for preparing perfluoro(lower)alkylbenzenes and derivatives thereof which comprises contacting a lower alkylbenzene or the corresponding derivative with hydrogen fluoride in the presence of chlorine in a gaseous phase at an elevated temperature to give the corresponding perfluoro(lower)alkylbenzene or its derivative.Type: GrantFiled: December 27, 1977Date of Patent: January 4, 1983Assignee: Daikin Kogyo Co., Ltd.Inventors: Uji Hiramatsu, Toshihide Honda, Yohnosuke Ohsaka
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Patent number: 4351975Abstract: A process for the preparation of monochlorinated and dichlorinated bis-(perhalomethyl)-benzenes of the formula (I) by reacting bis-(perhalomethyl)-benzenes of the formula (II) with elementary chlorine in chlorosulfonic acid as the reaction medium, at a temperature of, preferably, 0.degree. to 10.degree. C. The present invention makes it possible to obtain pure compounds of the formula (I), in high yields, in a single process step.Type: GrantFiled: March 24, 1981Date of Patent: September 28, 1982Assignee: Ciba-Geigy AGInventor: Athanassios Tzikas
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Patent number: 4334111Abstract: Benzotrihalides are prepared by pyrolyzing a substituted phenyl trihaloacetate of the formula ##STR1## wherein each X is halo, nitro, alkyloxy, aryloxy, aralkyoxy, cyano, lower alkyl, haloalkyl, haloalkyloxy, alkenyl, haloalkenyl, carbamoyl, N,N-dialkylcarbamoyl, N,N-diarylcarbamoyl, or N,N-diaralkyloxy;Y is halo; andn is an integer of from 1 to 5. As an example, 4-chlorophenyl trichloroacetate is pyrolyzed at 550.degree. C. to 4-chlorobenzotrichloride.Type: GrantFiled: February 17, 1978Date of Patent: June 8, 1982Assignee: The Dow Chemical CompanyInventors: Ralph A. Davis, R. Garth Pews
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Patent number: 4331613Abstract: A process for the preparation of an optionally substituted trifluoromethyl-naphthalene which comprises contacting a compound of the formula ##STR1## in which R.sup.1 denotes hydrogen, alkyl, aralkyl, aryl, aryloxy, arylthio, polyhalogenoalkoxy, polyhalogenoalkylthio, halogen, nitro, halogenocarbonyl, halogenosulphonyl, alkylsulphonyl or arylsulphonyl, it being possible for the aromatic nuclei contained in the substituents R.sup.1 to be in turn substituted by halogen, alkyl, polyhalogenoalkoxy or polyhalogenoalkylthio,R.sup.2 represents hydrogen, halogen or alkyl andR.sup.3, R.sup.4, R.sup.5 and R.sup.6 denote hydrogen, orR.sup.3 and R.sup.4 or R.sup.4 and R.sup.5 in each case together denote a fused-on aromatic ring, and wherein, in the case where R.sup.3 and R.sup.4 together form a fused-on aromatic ring,R.sup.5 and R.sup.6 independently of one another can also denote, in addition to hydrogen, halogen, nitro, halogenocarbonyl or halogenosulphonyl, and wherein, in the case where R.sup.4 and R.sup.Type: GrantFiled: June 23, 1980Date of Patent: May 25, 1982Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Erich Klauke
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Patent number: 4327036Abstract: Process for nuclear chlorination of non-phenolic aromatic compounds, said process comprising contacting and reacting a non-phenolic aromatic compound having a net Hammett .sigma. value of about -0.1 to about 2.0 with chlorine monoxide in the presence of at least one-half an equivalent amount, based on the chlorine monoxide, of an acid having a pK.sub.a no greater than that of trichloroacetic acid, provided, however, when the net Hammett .sigma. value is about 0.7 to about 2.0, the acid has a pK.sub.a no greater than that of trifluoroacetic acid.Type: GrantFiled: May 8, 1980Date of Patent: April 27, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Frank D. Marsh
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Patent number: 4324929Abstract: A process for producing mono, bis or tris(3,3,3-trifluoropropyl)benzene, which comprises bringing benzene into reaction with 3,3,3-trifluoropropylene in the presence of an acid catalyst selected from the group consisting of hydrogen fluoride, boron trifluoride and a mixture thereof, is disclosed.Type: GrantFiled: February 12, 1981Date of Patent: April 13, 1982Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Yoshiro Kobayashi, Itsumaro Kumadaki, Masaaki Takahashi, Takashi Yamauchi
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Patent number: 4226783Abstract: A process for .alpha.-chlorination of side chains of electronegatively substituted aromatic compounds with dichlorine monoxide.Type: GrantFiled: July 3, 1978Date of Patent: October 7, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: Frank D. Marsh