Haloalkyl Containing Compound Patents (Class 570/144)
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Patent number: 5763699Abstract: 2,2-diphenylhexafluoropropanes are prepared by condensation reaction of benzene or benzenes substituted with a halogen atom or atoms, a lower alkyl group or groups or a hydroxyl group or groups with hexafluoroacetone in the presence of trifluoromethane sulfonic acid. Among the 2,2-diphenylhexafluoropropanes, 2,2-diphenylhexafluoropropane and 2,2-bis(p-chlorophenyl)hexafluoropropane are novel compounds.Type: GrantFiled: November 27, 1996Date of Patent: June 9, 1998Assignee: Nippon Mektron, LimitedInventors: Lev Solomonovich German, deceased, Valerii Romanovich Polishchuk, deceased, Riichi Iwa, Haruyoshi Tatsu
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Patent number: 5730904Abstract: Partially fluorinated benzene derivatives of the formula I ##STR1## in which R, A.sup.1, A.sup.2, Q, Y, L.sup.1, L.sup.2, L.sup.3 and m are as defined in claim 1,are suitable as components of liquid-crystalline media.Type: GrantFiled: July 21, 1997Date of Patent: March 24, 1998Assignee: Merck Patent Gesellschaft MIT Beschrankter HaftungInventors: Ekkehard Bartmann, Sabine Schoen, Kazuaki Tarumi
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Patent number: 5723613Abstract: Methyl aromatic compounds of the formula (I) ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 have the meaning given in the description,can be reacted in an advantageous manner using free-radicals to give the associated trichloromethyl or tribromomethyl aromatic compounds, if the reaction is carried out in the presence of one or more chlorides or bromides of the heavy alkali metals.Type: GrantFiled: October 2, 1992Date of Patent: March 3, 1998Assignee: Bayer AktiengesellschaftInventor: Guido Steffan
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Patent number: 5702637Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion containing at least one methylene group and optionally containing at least one catenary ether oxygen atom; (b) a saturated, chiral or achiral, hydrocarbon terminal portion; and (c) a central core connecting the terminal portions. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.Type: GrantFiled: April 19, 1995Date of Patent: December 30, 1997Assignee: Minnesota Mining and Manufacturing CompanyInventors: Gilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
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Patent number: 5698136Abstract: A novel liquid crystalline compound having a high elastic constant ratio, K.sub.33 /K.sub.11, a superior compatibility with other liquid crystal compounds, particularly a low temperature compatibility therewith, and chemical stability; a liquid crystal composition containing such a liquid crystalline compound; and a liquid crystal display element, are provided,which liquid crystalline compound is expressed by the formula (1) ##STR1## wherein R.sub.1 is an alkyl group or an alkyloxy group of 1 to 10C or a halogenated alkyl group, a halogenated alkyloxy group of 1 to 4C, halogen atom or cyano group; R.sub.2 is H atom or an alkyl group of 1 to 3C; rings A and B each independently are 1,4-phenylene ring or trans-1,4-cyclohexylene group, which may be substituted by halogen atom; Z is single bond, 1,4-phenylene ring, trans-1,4-cyclohexylene ring or 1,2-ethylene group; p is 2 to 4; and q is 0 or 1.Type: GrantFiled: February 22, 1996Date of Patent: December 16, 1997Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Shuichi Matsui, Norihisa Hachiya, Etsuo Nakagawa
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Patent number: 5643495Abstract: 1,2,2,2-Tetrafluoroethyl ethers of the formula IR--(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --Z.sup.2 A.sup.3 --O--CHF--CF.sub.3(I)are suitable as components of liquid-crystalline media whereinR is H, a substituted or unsubstituted alkyl or alkenyl radical having 1 to 15 carbon atoms,A.sup.1 and A.sup.2 are each, independently of one another, a(a) trans-1,4-cyclohexylene radicals and derivatives thereof in which, in addition, one or more non-adjacent CH.sub.2 groups is optionally replaced by --O-- and/or --S--,(b) 1,4-phenylene radicals and derivatives thereof in which, in addition, one or two CH groups is optionally replaced by N, or(c) radical from the group consisting of 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl,wherein radicals (a) and (b) are optionally substituted by one or two fluorine atoms,Z.sup.1 and Z.sup.2 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.Type: GrantFiled: September 12, 1995Date of Patent: July 1, 1997Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Ekkehard Bartmann, Ulrich Finkenzeller
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Patent number: 5626793Abstract: A nematic liquid crystalline medium having at least two liquid crystalline components with at least one being of formula I ##STR1## wherein R is H, a straight-chain alkyl or alkenyl radical having 1 to 15 carbon atoms, it also being possible to replace one or more CH.sub.2 groups in these radicals, independently of one another, by --O--, --S--, ##STR2## --CO--, --CO--O--, --O--CO-- or --O--CO--O-- in such a way that oxygen atoms are not linked directly to one another,Z.sub.1 and Z are each, independently of one another, --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or a single bond, and one of the radicals Z.sup.1 and Z is alternatively --(CH.sub.2).sub.4 -- or --CH.dbd.CH--CH.sub.2 CH.sub.2 --,A and A.sup.1 are each, independently of one another, trans-1,4-cyclohexylene in which, in addition, one or two non-adjacent CH.sub.Type: GrantFiled: June 5, 1995Date of Patent: May 6, 1997Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Volker Reiffenrath, Herbert Plach, Detlef Pauluth, Reinhard Hittich, Eike Poetsch, Thomas Geelhaar, Georg Weber, Ekkehard Bartmann
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Patent number: 5621147Abstract: A 1,1,2-trifluoro-2-(trans-4-substituted cyclohexyl)ethylene of the formula (1):R--(A).sub.m --Cy--CF=CF.sub.2 (1)wherein R is a C.sub.1-10 alkyl group, a halogen atom or a cyano group, provided that in the case of the alkyl group, an oxygen atom may be interposed in a carbon-carbon bond of the alkyl group or in a carbon-carbon bond between this alkyl group and A, some of carbon-carbon bonds in the alkyl group may be triple bonds or double bonds, one --CH.sub.2 -- group in the alkyl group may be substituted by a carbonyl group, and some or all of hydrogen atoms in the alkyl group may be substituted by fluorine atoms;Cy is an unsubstituted trans-1,4-cyclohexylene group;A is a trans-1,4-cyclohexylene group, a 1,4-phenylene group or a 1,4-cyclohexenylene group, wherein each of such cyclic groups is unsubstituted or substituted by one or more halogen atoms or cyano groups, one or more =CH-- groups constituting rings of such cyclic groups may be substituted by nitrogen atoms, and one or more --CH.sub.Type: GrantFiled: May 4, 1995Date of Patent: April 15, 1997Assignee: Asahi Glass Company Ltd.Inventors: Osamu Yokokoji, Tamaki Simizu, Seisaku Kumai
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Patent number: 5600036Abstract: 2-Trifluoromethyl-4-chloro-benzalchloride and 2-methyl-3-nitro-5-chlorobenzotrifluoride, are intermediates in a process of preparing 2-methyl-3-aminobenzo-trifluoride. In this process, 2-trifluoromethyl-4-chlorobenzal-chloride is prepared by chlorinating o-trifluoromethylbenzalhalide, and 2-methyl-3-nitro-5-chlorobenzotrifluoride is prepared at first by hydrogenating the 2-trifluoro-methyl-4-chlorobenzalhalide to form a 2-methyl-5-monochlorobenzotrifluoride and then by nitrating the 2-methyl-5-monochlorobenzotrifluoride. Following this process, 2-methyl-3-aminobenzotrifluoride (MA-BTF) is prepared by hydrogenating the 2-methyl-3-nitro-5-chlorobenzotrifluoride. The thus prepared 2-methyl-3-aminobenzotrifluoride is useful as an intermediate in preparing medicines, agricultural chemicals and other chemical products.Type: GrantFiled: June 6, 1995Date of Patent: February 4, 1997Assignee: Central Glass Company, LimitedInventors: Takayuki Nishimiya, Masatomi Kanai, Toshikazu Kawai
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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: 5582767Abstract: The invention relates to liquid crystalline, multiply-substituted fluorinated tolane derivatives, their preparation, liquid crystalline mixtures which comprise such compounds and the use of these compounds and mixtures for electro-optical purposes.Type: GrantFiled: November 8, 1993Date of Patent: December 10, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Martin Schadt
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Patent number: 5571449Abstract: Partially fluorinated benzene derivatives of the formula I ##STR1## in which R, A.sup.1, A.sup.2, Z.sup.1, Z.sup.2, L.sup.1, L.sup.2 and m are as defined in claim 1, are suitable as components of liquid-crystalline media.Type: GrantFiled: January 19, 1995Date of Patent: November 5, 1996Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Herbert Plach, Rudolf Eidenschink
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Patent number: 5536892Abstract: A process for the preparation of octafluoro-[2,2]paracyclophane includes contacting a reactant selected from the group consisting of 1,4-bis (bromodifluoromethyl)benzene (dibromide), 1,4-bis (chlorodifluoromethyl)benzene (dichloride), and 1,4-bis (iododifluoromethyl)benzene (diiodide) with trimethylsilyltributyltin (TMSTBT) (a reducing agent) and fluoride ions in a refluxing solution of hexamethylphosphoramide (HMPA) or dimethylsulfoxide (DMSO) in tetrahydrofuran (THF) at conditions effective to promote a reaction product comprising octafluoro-[2,2]paracyclophane.Type: GrantFiled: October 18, 1995Date of Patent: July 16, 1996Assignee: Specialty Coating Systems, Inc.Inventors: William R. Dolbier, Jr., Xiao X. Rong
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Patent number: 5525258Abstract: Trifluorophenylene compounds of the formula (I) ##STR1## in which ##STR2## are mesogenic radicals, are useful components for liquid-crystal mixtures.Type: GrantFiled: April 18, 1995Date of Patent: June 11, 1996Assignee: Hoechst AktiengesellschaftInventors: Rainer Wingen, Ralf Pfirmann
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Patent number: 5484932Abstract: Compounds such as ##STR1## wherein R is F, CF.sub.3, CF.sub.2 H, CHF CF.sub.3 or CF.sub.2 CF.sub.3, as well as related compounds containing chlorine, are used as solvents in halogenation processes.Type: GrantFiled: June 2, 1994Date of Patent: January 16, 1996Assignee: Bayer AktiengesellschaftInventor: Albrecht Marhold
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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: 5475164Abstract: 3-Fluoro-4,6-dichlorotoluene is prepared with reduced formation of 3-fluoro-2,6-dichlorotoluene by chlorinating 3-fluorotoluene in the presence of a catalyst system to give a mixture containing 3-fluoro-6-chlorotoluene and 3-fluoro-4-chlorotoluene and chlorinating this in the presence of another catalyst system to give 3-fluoro-4,6-dichlorotoluene.Type: GrantFiled: November 22, 1994Date of Patent: December 12, 1995Assignee: Bayer AktiengesellschaftInventor: Werner Bussmann
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Patent number: 5458806Abstract: Fluoromethyl ketones of the formula I ##STR1## are suitable as components of liquid-crystalline media wherein R is H, a substituted or unsubstituted alkyl or alkenyl radical having 1 to 15 carbon atoms,A.sup.1 and A.sup.2 are each, independently of one another, a(a) trans-1,4-cyclohexylene radicals and derivatives thereof in which, in addition, one or more non-adjacent CH.sub.2 groups is optionally replaced by --O-- and/or --S--,(b) 1,4-phenylene radicals and derivatives thereof in which, in addition, one or two CH groups is optionally replaced by N, or(c) radical from the group consisting of 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl,wherein radicals (a) and (b) are optionally substituted by one or two fluorine atoms,Z.sup.1 and Z.sup.2 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.Type: GrantFiled: May 4, 1994Date of Patent: October 17, 1995Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Herbert Plach
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Patent number: 5416243Abstract: Cyclofluoralkylated fullerene compounds are prepared by reacting the fullerenes with a fluoroalkene as exemplified by tetrafluoroethylene or perfluoromethyl vinyl ether under thermolysis conditions as exemplified by temperatures of 200.degree. C., pressure and a halocarbon solvent, the products being useful as lubricants or additive thereto as well as in cooling systems, adhesives and polymers.Type: GrantFiled: August 29, 1994Date of Patent: May 16, 1995Assignee: E. I. DuPont de Nemours and CompanyInventors: Paul G. Bekiarian, Paul J. Fagan, Paul J. Krusic
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Patent number: 5382719Abstract: 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: April 19, 1994Date of Patent: January 17, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Paul J. Fagan
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Patent number: 5382718Abstract: Mixtures of cyclofluoroalkylated fullerenes are provided by the thermal 2+2 cycloaddition of fluoroalkenes to a solution or slurry of a fullerene. The cyclofluoroalkylated fullerene mixtures are useful as lubricants or additives to lubricants; in fluorocarbon and/or chlorofluorocarbon based cooling systems; in adhesives for fluorocarbon based polymers and in gas separation membranes.Type: GrantFiled: September 16, 1993Date of Patent: January 17, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Paul G. Bekiarian, Paul J. Fagan, Paul J. Krusic
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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: 5334788Abstract: Substrate compounds are reacted by passing them through an eductor with fluorine gas optionally in the presence of a liquid medium and preferably in a loop reactor with cooling means thereby providing rapid but controlled reaction suitable for industrial scale production. Vinylidene chloride, for example, smoothly produces dichlorodifluoroethane and dichlorotrifluoroethane in good yield.Type: GrantFiled: May 1, 1992Date of Patent: August 2, 1994Assignee: PCR Group, Inc.Inventors: Keith B. Baucom, Adam C. Alty, Earl J. Kimmel
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Patent number: 5315043Abstract: A process for halogen exchange fluorination or fluoro-denitration of aromatic compounds having at least one replaceable non-fluorine halogen or nitro substituent with an anhydrous substantially molten alkali metal acid fluoride composition wherein the alkali metal is potassium, rubidium or cesium.Type: GrantFiled: February 5, 1992Date of Patent: May 24, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Richard E. Fernandez, Mark H. Krackov
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Patent number: 5298188Abstract: The disclosure relates to fluorinated chiral liquid crystals that incorporate a cyclohexyl grouping in their structure. They can be used as dopants and lead to mixtures of ferroelectric liquid crystals that have an application in display systems. They meet the following chemical formula. ##STR1## with 1.ltoreq.n.ltoreq.14 if X=CH.sub.2 Y=--CH.sub.2 -- with R=CmH.sub.2m+1 and 5.ltoreq.m.ltoreq.Type: GrantFiled: February 24, 1992Date of Patent: March 29, 1994Assignee: Thomson-CSFInventors: Marie Vergnolle, Francoise Soyer, Pierre Le Barny, Jean-Claude Dudois
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Patent number: 5283378Abstract: Fluorine- and chlorine- and/or bromine-containing aromatic compounds are dechlorinated and/or debrominated with hydrogen in an industrially advantageous and selective manner, if the palladium catalyst is present in stationary phase and the aromatic compound in gas phase.Type: GrantFiled: September 29, 1992Date of Patent: February 1, 1994Assignee: Bayer AktiengesellschaftInventors: Dietmar Bielefeldt, Albrecht Marhold
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Patent number: 5276194Abstract: A process is provided for the catalytic perfluoroalkylation of aromatic compounds, wherein a perfluoroalkyl iodide or mixture of iodides is reacted with an aromatic compound in the presence of an aqueous base, such as an alkali metal hydroxide or carbonate. The use of an aqueous strong base increases the rate of reaction. Further improvements in rate and yield are secured by employing, as the catalyst, a noble metal supported on porous silica microspheres.Type: GrantFiled: May 7, 1993Date of Patent: January 4, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventor: Donald D. May
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Patent number: 5268517Abstract: The preparation of Z-1,2-diarylallyl chlorides of the general formula I ##STR1## in which R.sup.1 and R.sup.2, independently of one another, are hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or a substituted aromatic radical, and n and m are 1, 2 or 3, by dehydrating chlorohydrins of the formula II ##STR2## in which the radicals are as defined above, at up to 50.degree. C. in an inert ether or carboxylic acid ester as solvent and in the presence of a carboxylic anhydride and an organic or inorganic acid, the conversion thereof into azolylmethyloxiranes, and novel intermediates are described.Type: GrantFiled: December 7, 1992Date of Patent: December 7, 1993Assignee: BASF AktiengesellschaftInventors: Reiner Kober, Rainer Seele, Heinz Isak, Eckhard Hichmann, Norbert Goetz, Thomas Zierke
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Patent number: 5254747Abstract: Compounds are provided which comprise a fluorocarbon terminal portion and a chiral hydrocarbon terminal portion, said terminal portions being connected by a central core, said compounds having tilted smectic mesophases or having latent tilted smectic mesophases which develop when said compounds having said latent mesophases are in admixture with said compounds having tilted smectic mesophases or said compounds having latent tilted smectic mesophases.Type: GrantFiled: May 21, 1991Date of Patent: October 19, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventor: Eugene P. Janulis
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Patent number: 5233074Abstract: The invention describes a process for selectively preparing ortho-fluorinated substituted aromatic compounds wherein an aromatic compound containing a substituent capable of directing ortho metalation is contacted with a metalating reagent under reaction conditions sufficient to form an ortho-metalated substituted aromatic compound. The ortho-metalated substituted aromatic compound is reacted with an electrophilic fluorinating reagent under reaction conditions sufficient to form the desired ortho-fluorinated substituted aromatic compound which is then recovered from the reaction mixture. The process which utilizes a metalation intermediate prior to effecting the electrophilic fluorination step overcomes problems associated with prior art electrophilic fluorination processes which do not proceed through a regiospecifically controlled intermediate.Type: GrantFiled: June 1, 1992Date of Patent: August 3, 1993Assignee: Air Products and Chemicals, Inc.Inventor: Gauri S. Lal
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Patent number: 5233104Abstract: Aromatic compound are trifluoromethylated by reaction in the vapor phase with a dihalodifluoromethane in the presence of a copper/copper fluoride catalyst.Type: GrantFiled: August 27, 1992Date of Patent: August 3, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Donald D. May
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Patent number: 5213710Abstract: The invention relates to novel benzene derivatives of the formula I ##STR1## in which n is 0, 1, 2, 3, 4, 5, 6 or 7,Q is --O--, --CH.dbd.CH-- or a single bond,r is 0, 1, 2, 3, 4 or 5,s is 0, 1 or 2,X is F, Cl, OCHF.sub.2 or CF.sub.3,L is H or F, andA is ##STR2## Z, Z-Ar, Ar-Z, Z-Cyc in which Z is a single bond, --(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.4 --, Ar is 1,4-phenylene or biphenyl-4,4'-diyl and Cyc is trans-1,4-cyclohexylene.Type: GrantFiled: September 26, 1991Date of Patent: May 25, 1993Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Volker Reiffenrath, Reinhard Hittich, Herbert Plach
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Patent number: 5212301Abstract: Introduction of a fluoro substituent into an aromatic ring adjacent an electron donating group is difficult producing mixed isomers and low yields of desired products.A process for the introduction of a fluoro substituent into a substantially adjacent position to an electron-donating group into an aromatic compound in high yield is disclosed.The fluoroaromatic compounds are useful as synthetic intermediates for example in the manufacture of agrochemicals, pharmaceuticals and dyestuffs.Type: GrantFiled: May 8, 1992Date of Patent: May 18, 1993Assignee: Imperial Chemical Industries PLCInventors: John S. Moilliet, Richard D. Chambers, Michael H. Rock
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Patent number: 5210341Abstract: Processes are disclosed for the preparation of octafluoro-[2,2]paracyclophane which utilize a low temperature, e.g., less than about 200.degree. C., and a reducing agent comprising titanium to promote the dimerization of dihalo-tetrafluoro-p-xylenes. One suitable reducing agent is prepared by combining TiCl.sub.4 with LiAlH.sub.4 in an organic solvent.Type: GrantFiled: December 20, 1991Date of Patent: May 11, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: William R. Dolbier, Jr., M. A. Asghar, He-Qi Pan
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Patent number: 5177275Abstract: Substrate compounds are reacted by passing them through an eductor with fluorine gas optionally in the presence of a liquid medium and preferably in a loop reactor with cooling means thereby providing rapid but controlled reaction suitable for industrial scale production. Vinylidene chloride, for example, smoothly produces dichlorodifluoroethane and dichlorotrifluoroethane in good yield.Type: GrantFiled: May 1, 1989Date of Patent: January 5, 1993Assignee: PCR Group, Inc.Inventors: Keith B. Baucom, Adam C. Alty, Earl J. Kimmel
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Patent number: 5166365Abstract: A novel fluorine-containing aromatic compound of the formula: ##STR1## wherein X is ##STR2## in which R.sub.f is a perfluoroalkyl group having 1 to 10 carbon atoms,R.sub.f ' is a perfluoroalkyl group having 1 to 12 carbon atoms,p is an integer of 1 to 3,q is an integer of 0 to 3,r is 0 or 1,s is an integer of 0 to 5and t is an integer of 0 to 5,Y is X, a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a fluoroalkyl group having 1 to 8 carbon atoms, andeach A is independently ##STR3## in which D is an amino, carboxyl, hydroxyl, methyl or haloformyl group, and n is an integer of 1 or 2, or ##STR4## can be used to derive various compounds, some of which are useful for preparing a fluorine-containing epoxy compound of polyimide with good properties.Type: GrantFiled: May 10, 1990Date of Patent: November 24, 1992Assignee: Daikin Industries Ltd.Inventors: Yohnosuke Ohsaka, Tsutomu Kobayashhi, Motonobu Kubo
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Patent number: 5162577Abstract: A novel process for the lithiation of 1,3-bis(trifluoro-methyl)benzene in a solvent is described, said process comprising carrying out the lithiation with the lithium salt of an amine of the general formulaR.sup.1 R.sup.2 NH Iwherein R.sup.1 and R.sup.2 are secondary or tertiary lower alkyl or secondary or tertiary lower alkyl substituted by a lower alkyl or lower cycloalkyl or lower cycloaklyl substituted by a lower alkyl, or R.sup.1 and R.sup.2 taken together form a C.sub.6-14 -alkylene group in which the two carbon atoms linked with the nitrogen atom are secondary or tertiary and are separated from each other by 2 to 4 carbon atoms.The solution of the lithiated 1,3-bis(trifluoromethyl)-benzene obtained can be reacted with an electrophile which is suitable for the substitution of lethiated benzene derivatives, whereby a compound of the formula ##STR1## wherein R.sup.3 signifies the residue of an electrophile which is suitable for the substitution of lithiated benzene derivatives, is obtained.Type: GrantFiled: February 1, 1991Date of Patent: November 10, 1992Assignee: Hoffmann-La Roche Inc.Inventor: Raffaello Masciadri
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Patent number: 5126497Abstract: A partially deactivated reduction catalyst is prepared by reacting palladium on alumina catalyst with benzotrifluoride in an amount of 0.1 to 10.0 millimoles of benzotrifluoride per gram of alumina and hydrogen in an amount ranging from 10 to 2000 moles of hydrogen per mole of benzotrifluoride at a temperature of 200.degree. C. to 300.degree. C. for 30 minutes to 2 hours. The catalyst is useful for the reduction of trifluoromethylbenzonitriles and trifluoromethylbenzylamines to produce the corresponding trifluoromethyltoluenes in high yields. The catalyst is also useful in other hydrogen reduction reactions, e.g., for conversion of o-chlorobenzonitrile, o-chlorobenzylamine and mandelonitrile to toluene and for conversion of phenethylamine to ethylbenzene.Type: GrantFiled: June 21, 1991Date of Patent: June 30, 1992Assignee: Occidental Chemical CorporationInventors: Ronald F. Spohn, Raymond T. Olczak
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Patent number: 5118879Abstract: Fluoroalkyl derivatives which are novel compounds represented by the following general formula (I) or (II) of: ##STR1## orR.sub.1 --CH.dbd.CR.sub.2 (CF.sub.2).sub.n F (II)(wherein R.sub.1 stands for ##STR2## (where X stands for a hydrogen atom, a chlorine atom, a bromine atom, a fluorine atom, an iodine atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group or a nitro group), an aroyloxy group, or an alkyl or alkoxycarbonyl group having 1 to 20 carbon atoms, and R.sub.2 stands for a hydrogen atom or a methyl group; and n stands for an integer of from 1 to 20.) A process for the preparation of the derivative is a process comprising reacting an olefin compound and a fluoroalkanesulfonyl chloride in the presence of a metal catalyst, or a process comprising an additional alkali treatment step which follows the aforementioned process.Type: GrantFiled: October 25, 1990Date of Patent: June 2, 1992Assignee: Nippon Oil and Fats Co., Ltd.Inventors: Nobumasa Kamigata, Masato Yoshida, Hideo Sawada, Masaharu Nakayama
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Patent number: 5045229Abstract: Difluoromethylene compounds of the formula IR.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --Q--CF.sub.2 --(A.sup.3 --Z.sup.2).sub.n --A.sup.4 --R.sup.2 Iin which R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, A.sup.4, Z.sup.1, Z.sup.2, m and n are as defined herein and Q is --CO--, --O-- or --S--, can be used as components of liquid-crystalline media for liquid-crystal and electrooptical display elements.Type: GrantFiled: March 16, 1990Date of Patent: September 3, 1991Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Reinhard Hittich, Hans-Adolf Kurmeier, Eike Poetsch, Herbert Plach
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Patent number: 4978798Abstract: Disclosed is a method of making a bisphenyl dihalomethane by reacting a trihalomethylbenzene with a halobenzene and a Lewis acid. The bisphenyl dihalomethane can than be reacted with water to form a halobenzophenone. In an optical third step ring chlorines that are present can be replaced with fluorines and, in a final step, any remaining chlorines can be removed to leave a fluorobenzophenone. The process is particularly useful in making 4,4'-difluorobenzophenone, which is in turn useful in making polyetheretherketones.Type: GrantFiled: November 13, 1989Date of Patent: December 18, 1990Assignee: Occidental Chemical CorporationInventor: Jeffrey S. Stults
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Patent number: 4968830Abstract: Halogen substituted aromatic compounds of the formula ##STR1## wherein Y is selected from the group CO.sub.2 H, COF, COCl, COBr, CF.sub.3, CN, NCO, or F, and X and X' are independently hydrogen or a halogen selected from the group F-, Cl- and Br-, at least one of X and X' being halogen; may be prepared by the liquid phase reaction of a brominating agent, at temperatures below about 190.degree. Celsius, with a correspondingly substituted cyclohexene or cyclohexadiene.Type: GrantFiled: September 11, 1989Date of Patent: November 6, 1990Assignee: Occidental Chemical CorporationInventor: David Y. Tang
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Patent number: 4962246Abstract: Benzotrifluorides substituted by fluorine and optionally in addition by chlorine, some of which are new, are prepared by hydrogenating benzotrifluorides which are substituted by fluorine and chlorine, in the presence of a catalyst and a hydrogen chloride acceptor.Type: GrantFiled: July 7, 1989Date of Patent: October 9, 1990Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Rudolf Braden
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Patent number: 4937396Abstract: 3,4-Difluorobenzotrifluoride is prepared by contacting a 3,4-dihalobenzotrifluoride with an effective amount of KF or CsF in a polar aprotic solvent at an elevated temperature under substantially anhydrous conditions. The product can be removed as it is formed or the reaction may be run at the autogenous pressures generated by the reaction mixture in a sealed reactor.Type: GrantFiled: November 28, 1988Date of Patent: June 26, 1990Assignee: The Dow Chemical CompanyInventors: R. Garth Pews, Jack C. Little, James A. Gall
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Patent number: 4910351Abstract: A process for preparing (polyfluoroalkyl)polyfluoroarenes comprising contacting a polyfluoroalkyl or perfluoroalkylene of specified formulae with a polyfluoroaromatic in the presence of at least one specified metal reagent is disclosed.Type: GrantFiled: March 16, 1987Date of Patent: March 20, 1990Assignee: E. I. Du Pont de Nemours and CompanyInventor: Frank J. Weigert
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Patent number: 4895991Abstract: The process of direct synthesis of trifluoromethyl copper and trifluoromethyl aromatics, both intermediate reagents useful in direct synthesis of certain perfluoroalkyl compounds. The process involves a direct reaction between on the one hand an aromatic halide and a difluorodihalomethane and on the other hand copper and a difluorodihalomethane.Type: GrantFiled: January 25, 1989Date of Patent: January 23, 1990Assignee: University of Iowa Research FoundationInventors: Donald J. Burton, Denise M. Wiemers, Jerome C. Easdon
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Patent number: 4885415Abstract: Benzotrifluorides substituted by fluorine and optionally in addition by chlorine, some of which are new, are prepared by hydrogenating benzotrifluorides which are substituted by fluorine and chlorine, in the presence of a catalyst and a hydrogen chloride acceptor.Type: GrantFiled: July 15, 1988Date of Patent: December 5, 1989Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Rudolf Braden
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Patent number: 4868202Abstract: Novel 3-phenylpyrrole derivatives of the formula I ##STR1## wherein R.sup.1 is cyano, trifluoromethyl or C.sub.1 -C.sub.4 -alkoxycarbonyl, R.sup.2 is vinyl or a group --CH.sub.2 --CH.sub.2 --X, in which X is chlorine or bromine, or is cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenylsulfonyl, 4-bromophenylsulfonyl or 4-methylphenylsulfonyl, R is halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl, and n is zero, one or two, have valuable microbicidal properties for controlling phytopathogenic plant pests, particularly phytopathogenic fungi.Type: GrantFiled: December 22, 1987Date of Patent: September 19, 1989Assignee: Ciba-Geigy CorporationInventors: Pierre Martin, Robert W. Lang
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Patent number: 4861927Abstract: A process for preparing ring-halogenated .alpha.-methylstyrenes from the corresponding .alpha.-halocumenes is disclosed. The dehydrohalogenation is accomplished using only water and optionally an organic solvent. The process eliminates the need for added base and a phase-transfer catalyst.Type: GrantFiled: October 5, 1988Date of Patent: August 29, 1989Assignee: The Dow Chemical CompanyInventor: Mark R. Johnson
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Patent number: 4855517Abstract: Aromatic bromine compounds are prepared by reacting aromatic nitro compounds with elemental bromine in the gas phase at temperatures between about 310.degree. to 550.degree. C. In this reaction, the nitro groups are selectively replaced by bromine; further bromination of the aromatic system beyond that does not take place.Type: GrantFiled: September 21, 1987Date of Patent: August 8, 1989Assignee: Hoechst AktiengesellschaftInventors: Hans J. Metz, Klaus Warning