Halogen Bonded Directly To The Benzene Ring Patents (Class 568/656)
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Patent number: 6235949Abstract: A process for the preparation of halide compounds, preferably aryl halides, by contacting a gaseous mixture of hydrohalic acid and a compound selected from an aryl halogen formate, an aryl carbonate and equivalents thereof with a Lewis acid catalyst.Type: GrantFiled: March 10, 1997Date of Patent: May 22, 2001Assignee: Rhodia ChimieInventors: Herve Garcia, Laurent Gilbert, Serge Ratton, Christophe Rochin
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Patent number: 6211399Abstract: Disclosed is a method of adding 1 to 4 chlorine or bromine atoms to an aromatic ring of compound that has at least one electron-withdrawing groups on that ring. The aromatic compound is reacted with a chlorinating agent or a brominating agent in the presence of about 0.1 to about 10 mole % of a Lewis acid catalyst at a temperature of ambient to about 100° C. and a pressure of about 10 to about 100 psig.Type: GrantFiled: October 5, 1999Date of Patent: April 3, 2001Assignee: Occidental Chemical CorporationInventors: Michael C. Savidakis, David C. Johnson
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Patent number: 6172268Abstract: A method for producing an optically active 1-substituted 2-propanol of the following formula 1, which comprises reacting a hydroxy aromatic compound of the following formula 2 with an optically active propylene oxide in the presence of a catalyst: AOH Formula 2 CH3C*H(OH)CH2OA Formula 1 wherein A is a univalent aromatic group, and C* is an asymmetric carbon atom.Type: GrantFiled: January 28, 2000Date of Patent: January 9, 2001Assignee: Asahi Glass Company, LimitedInventors: Toshihiko Tohma, Tomoyuki Asai
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Patent number: 6166273Abstract: A process is provided for increasing the fluorine content of benzene or pyridine rings which are optionally substituted with from 1 to 3 inert substituents. The process involves (a) contacting the ring with a metal fluoride composition comprising cupric fluoride (CuF.sub.2) at a temperature above 250.degree. C. sufficient to transfer F from cupric fluoride to the optionally substituted ring, thereby chemically reducing the metal fluoride composition; (b) oxidizing the reduced metal fluoride composition from (a) in the presence of HF to regenerate a metal fluoride composition comprising cupric fluoride; and (c) employing regenerated metal fluoride composition of (b) in (a).Type: GrantFiled: July 27, 1999Date of Patent: December 26, 2000Assignee: E.I. du Pont de Nemours and CompanyInventor: Munirpallam A. Subramanian
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Patent number: 6124507Abstract: Novel compositions of the structure ##STR1## wherein R.sup.1 and R.sup.2 are each an alkoxy group which may be the same or different and have from one to ten carbon atoms, and R.sup.3 -R.sup.6 are each individually, hydrogen, hydrocarbyl, hydrocarboxy, nitro, a silyl group or a halogen, with the provisos that if either R.sup.1 or R.sup.2 are methoxy, then at least one of R.sup.3 -R.sup.6 is not hydrogen, if R.sup.1 and R.sup.2 are both ethoxy, then at least one of R.sup.3 -R.sup.6 is not hydrogen, and R.sup.1 and R.sup.2 cannot both be methoxy, are taught herein, which may be used as electron donors, either internal or external, for catalysts used in the polymerization of olefins.Type: GrantFiled: December 10, 1997Date of Patent: September 26, 2000Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stanley Edward Wilson, Robert Converse Brady, III
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Patent number: 6118018Abstract: Disclosed is a method of adding 1 to 4 chlorine or bromine atoms to an aromatic ring of compound that has at least one electron-withdrawing groups on that ring. The aromatic compound is reacted with a chlorinating agent or a brominating agent in the presence of about 0.1 to about 10 mole % of a Lewis acid catalyst and about 0.001 to about 0.1 equivalents of an iodine-containing cocatalyst at a temperature of ambient to about 100.degree. C.Type: GrantFiled: December 6, 1999Date of Patent: September 12, 2000Assignee: Occidental Chemical CorporationInventors: Michael C. Savidakis, Michael J. Fifolt, Daniel R. Thielen, Ronald Spohn, David C. Johnson, William S. Derwin
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Patent number: 5981789Abstract: Disclosed is a method of preparing an aromatic compound having the general formula ##STR1## where 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, and q+m+n is an integer from 1 to 5. A vapor is prepared of a substrate having the general formula ##STR2## and a chlorinating agent. The mixture is reacted at a temperature above the boiling point of the substrate but below its decomposition temperature. The amount of chlorinating agent is about 0.5 to about 2 times the amount stoichiometrically required to replace the nitro groups on the substrate with chlorine. Unreacted substrate and partially reacted substrate are condensed from the product mixture and are recycled. The substrate is preferably in contact with the chlorinating agent before it is vaporized.Type: GrantFiled: December 30, 1998Date of Patent: November 9, 1999Assignee: Occidental Chemical CorporationInventors: John Hickey, Robert L. Bell, George Piotrowski
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Patent number: 5907063Abstract: Activated aromatic compounds are more economically ring brominated by reacting the compounds with a sulfoxide/HBr brominating agent while removing water from the reaction mixture. The water removal provides high conversions and yields when employing stoichiometric quantities of reactants.Type: GrantFiled: March 24, 1998Date of Patent: May 25, 1999Assignee: Albemarle CorporationInventor: Kevin J. Theriot
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Patent number: 5874656Abstract: o-Alkylfluorobenzenes are advantageously prepared by heating the corresponding chloroformates to from 70.degree. to 200.degree. C. in the liquid phase in the presence of hydrogen fluoride and in the presence of an inert diluent other than a halogenated alkane.Type: GrantFiled: October 7, 1997Date of Patent: February 23, 1999Assignee: Bayer AktiengesellschaftInventors: Norbert Lui, Michael-Harold Rock
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Patent number: 5849959Abstract: The present invention relates to compounds of the formula (1) ##STR1## where R is H, a straight-chain or branched alkyl radical with 1 to 6 carbons, a fluorinated straight-chain or branched alkyl radical with 1 to 6 carbons, a benzyl radical, or a benzyl radical substituted by an alkyl group or alkoxy group with 1 to 4 carbons each, or by halogen, X is H, Cl, Br or I, and X is different from R, and a process for their preparation.Type: GrantFiled: December 11, 1996Date of Patent: December 15, 1998Assignee: Clariant GmbHInventors: Ralf Pfirmann, Rainer Wingen
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Patent number: 5817888Abstract: A bromination process for organic compounds employs stabilized bromine chloride solutions as the brominating agent. Activated aromatic compounds such as anisole can be selectively monobrominated in the para-position in high purity and yield.Type: GrantFiled: June 9, 1997Date of Patent: October 6, 1998Assignee: Albemarle CorporationInventors: Hassan Y. Elnagar, Robert L. Davis, Mahmood Sabahi
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Patent number: 5773668Abstract: Disclosed is a method of making trichloromethoxybenzene. A mixture is prepared of anisole and a source of chlorine free radicals, such as chlorine or sulfuryl chloride. The reaction is performed in a solvent, which can be either benzotrifluoride, orthochlorobenzotrifluoride, metachlorobenzotrifluoride, parachlorobenzotrifluoride, or dichlorobenzotrifluoride. The mixture is exposed to actinic radiation, such as ultraviolet light, which generates the chlorine free radicals.Type: GrantFiled: February 24, 1997Date of Patent: June 30, 1998Assignee: Occidental Chemical CorporationInventors: Lawrence Fertel, Michael Fifolt, Mary Cocoman, Walter Opalinski, William Derwin
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Patent number: 5654493Abstract: The present invention relates to a process for preparing 4-bromophenyl alkyl ethers by reacting phenyl alkyl ethers with bromine in a water-miscible solvent in the presence of an oxidizing agent which is able to oxidize hydrogen bromide to bromine.Type: GrantFiled: August 26, 1996Date of Patent: August 5, 1997Assignee: Hoechst AktiengesellschaftInventor: Thomas Wessel
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Patent number: 5606084Abstract: The present invention relates to the preparation and uses of 1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts, specifically 1-hydroxyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts as reagents for the introduction of fluorine in organic compounds.Type: GrantFiled: June 7, 1995Date of Patent: February 25, 1997Assignee: AlliedSignal Inc.Inventors: Andrew J. Poss, George Shia
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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: 5478964Abstract: The invention describes N-fluorosulfonimides which are useful as fluorinating agents. The N-fluorosulfonimides are stable, easily synthesized, and allow the introduction of fluorine into organic compounds under mild conditions.Type: GrantFiled: December 10, 1992Date of Patent: December 26, 1995Assignee: Allied-Signal Inc.Inventor: Edmond Differding
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Patent number: 5476646Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a nonionic x-ray producing agent in combination with a pharmaceutically acceptable clay in a pharmaceutically acceptable carrier; and methods for their use in diagnostic radiology of the gastrointestinal tract.Type: GrantFiled: April 21, 1994Date of Patent: December 19, 1995Assignee: Sterling Winthrop Inc.Inventors: Stephen B. Ruddy, Gregory L. McIntire, Mary E. Roberts, John L. Toner
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Patent number: 5463088Abstract: A process for preparing perfluoroalkoxy(alkylthio)benzenes from perfluorochloroalkoxy(alkylthio)-benzenes by reaction with hydrogen fluoride in the gas phase and in the presence of a catalyst.Type: GrantFiled: April 26, 1994Date of Patent: October 31, 1995Assignee: Bayer AktiengesellschaftInventors: Norbert Lui, Albrecht Marhold, Karl-Rudolf Gassen
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Patent number: 5463138Abstract: Difluoromethoxyarenes and difluoromethylthioarenes of the general formula (I),Ar--Q--CHF.sub.2 (I)in whichAr represents optionally substituted aryl, andQ represents oxygen or sulphur,(which can be used as intermediates for preparing biologically active products) are obtained in very good yields and in a high degree of purity by reacting hydroxyarenes or mercaptoarenes of the general formulaAr--Q--H (II)with chlorodifluoromethane (ClCHF.sub.2) in the presence of an aqueous alkali metal hydroxide or alkaline earth metal hydroxide at temperatures of between 20.degree. C. and 120.degree. C.Type: GrantFiled: May 18, 1994Date of Patent: October 31, 1995Assignee: Bayer AktiengesellschaftInventor: Klaus-Helmut Muller
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Patent number: 5446186Abstract: The synthesis and compound of a new caged calcium which is an ortho-nitrophenyl derivative of EGTA and various intermediates. It is synthesized in ten steps and 24% overall yield. The photosensitive chelator, nitrophenyl-EGTA, has a K.sub.d for Ca.sup.2+ of 80 nM and for Mg.sup.2+ of 8.8 mM. Upon exposure to ultra-violet light (in the region of 350 nm), the chelator is cleaved, yielding iminodiacetic acid photoproducts with known low Ca-affinity (K.sub.d =1 mM). The quantum yield of photolysis of nitrophenyl-EGTA in the presence of Ca.sup.a+ is 0.23 and in the absence of Ca.sup.2+ is 0.20. In experiments with chemically skinned skeletal muscle fibers, a fully relaxed fiber equilibrated with nitrophenyl-EGTA:Ca.sup.2+ complex, in the presence of physiological [Mg.sup.2+ ] (i.e. 1.0 mM), produced maximal contraction after a single flash from a frequency doubled ruby laser (347 nm). Half-maximal tension was achieved in 18 ms at 15.degree. C.Type: GrantFiled: November 9, 1993Date of Patent: August 29, 1995Inventors: Graham C. R. Ellis-Davies, Jack H. Kaplan
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Patent number: 5443814Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a nonionic x-ray producing agent in combination with a cellulose derivative in a pharmaceutically acceptable carrier; and methods for their use in diagnostic radiology of the gastrointestinal tract.Type: GrantFiled: March 4, 1994Date of Patent: August 22, 1995Assignee: Sterling Winthrop, Inc.Inventors: Carl R. Illig, John L. Toner, Robert W. Lee, Edward J. Baker
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Patent number: 5440051Abstract: Aryl ethers are chlorinated in the .alpha.-position by a process in which they are metered into a reaction vessel at the same time as chlorine, the reaction being carried out at temperatures in the range from 60.degree. to 150.degree. C.Type: GrantFiled: March 22, 1994Date of Patent: August 8, 1995Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Klaus Jelich
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Patent number: 5422035Abstract: A liquid-crystalline medium based on a mixture of polar compounds having positive dielectric anisotropy, comprising one or more compounds of the formula I ##STR1## in which R, A.sup.1,. A.sup.2, Z.sup.1, Z.sup.2, m, n, L.sup.1, L 2 and L.sup.3 are as defined in claim 1.Type: GrantFiled: May 9, 1994Date of Patent: June 6, 1995Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Herbert Plach, Andreas Ruhl
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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: 5399292Abstract: Fluoro-substituted phenyl-cyclohexylacetylenes have the formula: ##STR1## wherein R signifies alkyl, alkoxy, alkenyl or alkenyloxy with 1 or, respectively, 2 to 12 carbon atoms in which one CH.sub.2 group can be replaced by oxygen and/or one or more hydrogen atoms can be replaced by fluorine atoms, with the proviso that two oxygen atoms are not directly adjacent;A.sup.1 represents 1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl;A.sup.2 signifies trans-1,4-cyclohexylene or 1,4-phenylene which is optionally substituted with fluorine;Z.sup.1 signifies a single covalent bond, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O-- or, when ring A.sup.1 represents a saturated ring, also the trans form of --CH.dbd.CH(CH.sub.2).sub.2 -- or --CH.dbd.CHCH.sub.2 O--;Z.sup.2 signifies a single covalent bond, --CH.sub.2 --CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.Type: GrantFiled: May 2, 1994Date of Patent: March 21, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Martin Schadt
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Patent number: 5393776Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.Type: GrantFiled: May 13, 1994Date of Patent: February 28, 1995Assignee: Bristol-Myers Squibb CompanyInventor: Bradley C. Pearce
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Patent number: 5387718Abstract: Alkylphenyl alkyl ethers or alkylphenyl alkyl thioethers, of the formula ##STR1## where U represents O or S; and R.sub.1 -R.sub.6 each independently represent an alkyl or aryl group with 1-6 C atoms, but R.sub.1 -R.sub.5 may each independently represent a functional group other than these, particularly --COOR (R=C.sub.1-4 alkyl), --NO.sub.2, --NH.sub.2, --O--CH.sub.2 --CH.sub.2 --OH, --OH, --CHO, --H, or -halogen;R.sub.1 -R.sub.5 may be bridged by suitable bifunctional substituents, such as, e.g., --(CH.sub.2).sub.x --, or --(CH.sub.2).sub.x --Z--(CH.sub.2).sub.y -- (where Z represents a hetero atom; x=0-7 and y=0-7), or by unsaturated substituents or anellated ring systems; may be produced in high space-time yield by reacting the corresponding phenol or thiophenol with a arylalkyl carbonate at a temperature of 70.degree.-300.degree. C. under elevated or normal pressure, in the presence of a monocyclic, bicyclic, polycyclic, or acyclic amidine as a catalyst.Type: GrantFiled: July 14, 1992Date of Patent: February 7, 1995Assignee: Huels AktiengesellschaftInventors: Gunther Kohler, Peter Bickert
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Patent number: 5382379Abstract: A novel liquid crystal material having an alkenyl group at the end of the molecule, and having a low viscosity is provided. When the compound is added to a display element it is able to reduce the threshold voltage of the resulting display element. The compound is expressed by the formula (I), ##STR1## wherein X is a F atom, a trifluoromethyl group, a trifluoromethoxy group or a difluoromethoxy group, --A-- is 1,4-cyclohexylene or 1,4-phenylene, --B-- is 1,4-cyclohexylene, l is 0, 1 or 2, m is 0, 1 or 2, l+m.gtoreq.1, Z is --CH.sub.2 CH.sub.2 -- or single bond, n is an integer of 0 to 4, R is a H atom or a linear or branched alkyl group of 1-7C, and when R is an alkyl group, the double bond has a trans-configuration. The compounds of the present invention are suitable as liquid crystal material for STN display element, and further are chemically stable; hence it is possible to prepare a composition having a superior multiplex characteristic and capable of effecting a low voltage drive.Type: GrantFiled: October 7, 1993Date of Patent: January 17, 1995Assignee: Chisso CorporationInventors: Yuichi Onji, Makoto Ushioda, Shuichi Matsui, Tomoyuki Kondo, Yasuyuki Goto
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Patent number: 5356562Abstract: Fluoro tolans of the formula I ##STR1## wherein R.sup.1 denotes alkyl with up to 12 carbon atoms wherein one or two non-adjacent CH.sub.2 groups may also be replaced by --O--, --O--CO--, --CO--O-- and/or --CH.dbd.CH--,A is trans-1,4-cyclohexylene or 1,4-phenylene,r is 0 or 1,s is 0 or 1,Q is --CF.sub.2 -- or --OCF.sub.2 -- and -- if Y=F and/or L.sup.1 =L.sup.2 =F - also a single bond,L.sup.1 and L.sup.2 are H or F, andY is H, F or Clare suitable as components of liquid crystalline media.Type: GrantFiled: June 3, 1992Date of Patent: October 18, 1994Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Simon Greenfield, Emma Brown, Reinhard Hittich
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Patent number: 5318768Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a polymeric material in combination with a divalent cation capable of forming a coating on the gastrointestinal tract and a crystalline contrast agent in a pharmaceutically acceptable carrier; and methods for their use in diagnostic radiology of the gastrointestinal tract.Type: GrantFiled: February 17, 1993Date of Patent: June 7, 1994Assignee: Sterling Winthrop Inc.Inventors: Carl R. Illig, Eugene R. Cooper
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Patent number: 5260049Abstract: Disclosed are aqueous compositions containing a contrast agent of the formula ##STR1## and methods for their use in diagnostic radiology of the gastrointestinal tract, wherein R is a substituted or unsubstituted alkyl group containing from 2 to 8 carbon atoms, wherein said substituents are selected from the group consisting of C.sub.1 -C.sub.6 alkyl, hydroxy and alkoxy; and n is 1 to 5.Type: GrantFiled: May 1, 1992Date of Patent: November 9, 1993Assignee: Sterling Winthrop Inc.Inventors: Carl R. Illig, John L. Toner
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Patent number: 5254732Abstract: The invention describes N-fluorosulfonimides which are useful as fluorinating agents. The N-fluorosulfonimides are stable, easily synthesized, and allow the introduction of fluorine into organic compounds under mild conditions.Type: GrantFiled: February 28, 1992Date of Patent: October 19, 1993Assignee: Allied-Signal Inc.Inventor: Edmond Differding
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Patent number: 5248447Abstract: 2,3-difluorohydroquinone compounds of the formula I ##STR1## in which R.sup.1 and R.sup.2, in each case independently of one another, are alkyl having 1 to 15 C atoms or alkenyl having 3 to 15 C atoms which are unsubstituted, monosubstituted by cyano or at least monosubstituted by fluorine or chlorine, it also being possible for one CH.sub.2 group in these radicals to be replaced by --O--, --CO--, --CO--O--, --O--CO-- or --O--CO--O--,A.sup.1, A.sup.2 and A.sup.3, in each case independently of one another, are(a) trans-1,4-cyclohexylene, in which, in addition, one or two non-adjacent CH.sub.Type: GrantFiled: April 21, 1992Date of Patent: September 28, 1993Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Thomas Geelhaar, David Coates, Ian C. Sage, Simon Greenfield
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Patent number: 5247124Abstract: A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.Type: GrantFiled: August 25, 1992Date of Patent: September 21, 1993Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
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Patent number: 5243088Abstract: Dibromonaphthalene compounds having the formula (1): ##STR1## are 1-monodebrominated by reacting same, neat or in an acid organic solvent, with molecular hydrogen or a compound that generates nascent hydrogen, in situ, in the medium of reaction, in the presence of a catalytically effective amount of a hydrodebromination catalyst.Type: GrantFiled: October 31, 1991Date of Patent: September 7, 1993Assignee: Potasse et Produits ChimiquesInventors: Roland Jacquot, Francoise Truchet
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Patent number: 5210278Abstract: A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.Type: GrantFiled: August 25, 1992Date of Patent: May 11, 1993Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
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Patent number: 5194672Abstract: A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.Type: GrantFiled: May 14, 1991Date of Patent: March 16, 1993Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
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Patent number: 5126461Abstract: Process for ring opening compounds of the formula ##STR1## in which R.sup.1 is heteroaryl or aryl, R.sup.2 is a leaving group, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently selected from hydrogen, alkyl, aralkyl, aryl, heteroaryl and alkenyl, provided that at least one of the groups R.sup.3 to R.sup.6 is other than hydrogen, by breaking the bond joining the carbon atom attached to R.sup.3 and the carbon atom attached to R.sup.6 in organic solution using silica, giving useful diene or allyl derivatives, certain of which are novel.Type: GrantFiled: November 14, 1990Date of Patent: June 30, 1992Assignee: Shell Research LimitedInventors: Mark S. Baird, Ian Bruce
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Patent number: 5122297Abstract: The invention relates to novel tetracyclic benzene derivatives of the formula I ##STR1## in which n is 1 to 7, A is trans-1,4-cyclohexylene, 1,4-phenylene, 3-fluoro-1,4-phenylene or 3,5-difluoro-1,4-phenylene, X is F, Cl, CF.sub.3, --OCF.sub.3 or --OCHF.sub.2, and L, Y and Z are each, independently of one another, H or F.Type: GrantFiled: April 25, 1991Date of Patent: June 16, 1992Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Volker Reiffenrath, Reinhard Hittich, Herbert Plach
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Patent number: 5093526Abstract: N-n-propyl-N-2-(2,4,6-trichlorophenoxy) ethyl amine is prepared by reacting 2-phenoxy ethanol with thionyl chloride in the presence of a catalytic amount of tetra-alkyl ammonium halide optionally in the presence of a solvent to form 2-phenoxy ethyl chloride; reacting the 2-phenoxy ethyl chloride with n-propylamine at a temperature of from 50.degree. C. to 150.degree. C. optionally in the presence of a solvent to form N-n-propyl-N-2-phenoxy-ethyl amine; selectively chlorinating N-n-propyl-N-2-phenoxyethyl amine with chlorine in the presence of a solvent; and recovering the N-n-propyl-N-2-(2,4,6-trichlorophenoxy) ethyl amine formed.Type: GrantFiled: June 14, 1990Date of Patent: March 3, 1992Assignee: Makhteshim Chemical Works Ltd.Inventors: Joseph Sharvit, Abraham A. Pereferkovich
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Patent number: 5091577Abstract: N-n-propyl-N-(2,4,6-trichlorophenoxy)-ethyl amine is prepared by reacting 2-phenoxy ethanol with thionyl chloride in the presence of a catalytic amount of tetraalkyl ammonium halide optionally in the presence of a solvent to form 2-phenoxy ethyl chloride; selectively chlorinating the 2-phenoxy ethyl chloride with chlorine at a temperature from 0.degree. C. to 60.degree. C. in the presence of a catalytic amount if urea to form 2-(2,4,6-trichlorophenoxy)-ethyl chloride; reacting the 2-(2,4,6-trichlorophenoxy)-ethyl chloride with n-propyl amine at a temperature of from 20.degree. C. to 150.degree. C., optionally in the presence of water; and recovering the N-n-propyl-N-2-(2,4,6-trichlorophenoxy)-ethyl amine formed.Type: GrantFiled: June 14, 1990Date of Patent: February 25, 1992Assignee: Makhteshim Chemical Works Ltd.Inventors: Joseph Sharvit, Abraham A. Pereferkovich
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Patent number: 5091578Abstract: N-n-propyl-N-2-(2,4,6-trichlorophenoxy)-ethylamine is prepared by selectively chlorinating 2-phenoxy ethanol by reacting it with chlorine either in the presence of hydrogen chloride at a temperature of from -10.degree. C. to 50.degree. C. or in the presence of urea at a temperature of from 20.degree. C. to 55.degree. C. in a water/carbon tetrachloride solvent mixture to form 2-(2,4,6-trichlorophenoxy)ethanol; reacting the 2-(2,4,6-trichlorophenoxy)ethanol with thionyl chloride in the presence of a catalytic amount of tetraalkyl ammonium chloride, optionally in the presence of a solvent to form 2-(2,4,6-trichlorophenoxy)ethyl chloride; and reacting the 2-(2,4,6-trichlorophenoxy) ethyl chloride with n-propylamine at a temperature of from 20.degree. C. to 150.degree. C., optionally in the presence of water to form N-n-propyl-N-2-(2,4,6-trichlorophenoxy) ethyl amine.Type: GrantFiled: June 14, 1990Date of Patent: February 25, 1992Assignee: Makhteshim Chemical Works Ltd.Inventors: Joseph Sharvit, Abraham A. Pereferkovich, Daniel Shohat
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Patent number: 5087764Abstract: 1,4-disubstituted 2,3-difluorobenzenes according to formula I are suitable as intermediates for the synthesis of liquid crystalline compounds.Type: GrantFiled: May 12, 1989Date of Patent: February 11, 1992Assignee: Merck Patent Gesellschaft mit beschrankter HafungInventors: Volker Reiffenrath, Joachim Krause
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Patent number: 5086178Abstract: Fluorinated diazabicycloalkane derivative of the following Formula I: ##STR1## wherein n represents 0, 1 or 2; R represents a quaternizing organic group; each R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 independently represents hydrogen, C.sub.1 -C.sub.6 alkyl, aryl, C.sub.1 -C.sub.6 alkyl-substituted aryl or aryl-substituted C.sub.1 -C.sub.6 alkyl and each X.sup.- independently represents a conterion or 2X.sup.- represents a single divalent counterion, are electrophilic fluorinating agents.Type: GrantFiled: September 20, 1990Date of Patent: February 4, 1992Assignee: Air Products and Chemicals, Inc.Inventor: Ronald E. Banks
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Patent number: 5008464Abstract: An improved method for the production of 4-bromo-3-alkylanisole, particularly 4-bromo-3-methylanisole is described. The method involves establishing 3-alkylanisole as a vapor in a reaction zone of a reactor and establishing bromine as a vapor. Thereafter the bromine vapor is introduced to the reaction zone of the reactor and commingled with the established 3-alkylanisole vapor. Dibrominated impurity is substantially reduced.Type: GrantFiled: May 29, 1990Date of Patent: April 16, 1991Assignee: East Short Chemical CompanyInventor: Larry Filius
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Patent number: 4960884Abstract: Pesticidal mono-, di-, and tri-2-fluoroethyl ethers of the formula R.sup.1 R.sup.2.sub.m Ar(OCH.sub.2 CH.sub.2 F).sub.n, compositions thereof and their insecticidal, acaricidal and nematicidal uses are described and claimed.Type: GrantFiled: August 28, 1989Date of Patent: October 2, 1990Assignee: FMC CorporationInventors: David M. Roush, Donald A. Shaw, Michael L. Jones, Jun H. Chang
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Patent number: 4940807Abstract: Electron-rich aromatic compounds are selectively brominated in good yield in the presence of water using potassium tribromide as the brominating agent. In this way monobromination is favored and dibromination is suppressed as compared to the use of elemental bromine as the brominating agent.Type: GrantFiled: June 12, 1989Date of Patent: July 10, 1990Assignee: Ethyl CorporationInventor: Robert N. DePriest
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Patent number: 4927956Abstract: 3-substituted-4-hydroxy- and 4-acetoxystyrene compounds, especially 3,5-di(methyl, bromo or chloro)-4-acetoxystyrene as well as a process for its preparation. 2,6-dimethylphenol is acylated with acetic anhydride and HF catalyzed to produce 3,5-dimethyl-4-hydroxy-acetophenone. After subsequent esterification with acetic anhydride and catalyzed hydrogenation to form 1-(3',5'-dimethyl-4'-acetoxyphenyl)ethanol, this intermediate is then dehydrated with an acid and a polymerization inhibitor to produce 3,5-dimethyl-4-acetoxystyrene.Type: GrantFiled: June 2, 1989Date of Patent: May 22, 1990Assignee: Hoechst Celanese CorporationInventors: Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
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Patent number: 4914244Abstract: Difluorochloromethoxybenzenes are prepared by reacting phenols with trichloromethyl chloroformate (=di-phosgene) in the presence of hydrogen fluoride.Type: GrantFiled: January 14, 1987Date of Patent: April 3, 1990Assignee: Bayer AktiengesellschaftInventor: Albrecht Marhold
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Patent number: 4891450Abstract: The invention provides novel arylalkene compounds of formula I, a process for their preparation and their use as intermediates for insecticidal compounds, comprising, ##STR1## wherein W represents 1 to 4 substituents selected from halo, alkyl, alkoxy, haloalkyl, haloalkoxy and alkoxyalkyl, or W represents a bidentate alkylene or alkylenedioxy group linking adjacent carbon atoms, X represents fluoroalkyl, and Y is selected from chlorine, bromine and alkoxy; and a process for preparing said ethers. The compounds of formula I are prepared by reacting a ketone of formula: ##STR2## with a phosphonium salt of formula Hal.sup.- (Q).sub.3 P.sup.+ -CH.sub.2 -Y, where Hal.sup.- represents a halide ion and Q represents alkyl or aryl.Type: GrantFiled: January 25, 1988Date of Patent: January 2, 1990Assignee: Imperial Chemical Industries PLCInventors: Robin A. E. Carr, Lyn Powell