Grignard Type Patents (Class 260/665G)
  • Patent number: 6129863
    Abstract: Perfluoroaryl Grignard reagents are produced from a hydrocarbyl Grignard reagent and polyhaloaromatic compounds via separate additions of different polyhaloaromatic compounds, such that the conversion of hydrocarbyl Grignard reagent to the desired perfluoroaryl Grignard reagent is essentially complete, and thus the reaction product is free or essentially free of agents that may negatively affect subsequent reactions. The perfluoroaryl Grignard reagents may be further reacted with boron trihalides in order to obtain tris(perfluoroaryl)boranes or tetrakis(perfluoroaryl)borates.
    Type: Grant
    Filed: December 18, 1998
    Date of Patent: October 10, 2000
    Assignee: Albemarle Corporation
    Inventors: John Y. Lee, David W. Owens, Charles R. Everly, Ronny W. Lin, John M. Power, Steven P. Diefenbach, Niomi L. Krzystowczyk
  • Patent number: 6117372
    Abstract: Grignard compounds from aromatic chlorine compounds and magnesium metal in the presence of a transition metal/magnesium chloride complex as a catalyst.
    Type: Grant
    Filed: January 5, 1999
    Date of Patent: September 12, 2000
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Borislav Bogdanovic, Manfred Schwickardi
  • Patent number: 6080888
    Abstract: Arylolefinic compounds are prepared by reacting aryl halide with an olefinic compound in the presence of a polar liquid reaction medium containing (a) secondary or tertiary amine as a hydrogen halide acceptor (b) a catalyst system formed from (i) Pd or Pd(0) compound, and/or Pd(I) salt or Pd(II) salt, and (ii) a tertiary phosphine ligand, and (c) a reaction accelerating amount of water in the range of about 0.5 to about 5 weight percent of the total weight of the reaction mixture. The arylolefinic compounds can be converted to an arylcarboxylic acid by hydrocarboxylation with CO in a reaction medium freed of amine and containing water and a Pd catalyst system as above in which a copper component may be included, and which preferably includes an ether such as THF.
    Type: Grant
    Filed: January 8, 1997
    Date of Patent: June 27, 2000
    Assignee: Albemarle Corporation
    Inventors: Tse-Chong Wu, Kannappan C. Chockalingham, W. Dirk Klobucar, Gary D. Focht
  • Patent number: 6057480
    Abstract: A fluoroaryl magnesium derivative is produced by reacting aryl fluoride, hydrocarbon halide, and magnesium with one another in an ether solvent or a mixed solvent of the ether solvent and a hydrocarbon solvent. Also, a (fluoroaryl)borane compound is produced by mixing both a solution prepared by dissolving the fluoroaryl magnesium derivative into the ether solvent and another solvent prepared by dissolving the boron halide in the ether solvent with a hydrocarbon solvent having a higher boiling point than the ether solvent, so that the fluoroaryl magnesium derivative and boron halide react with each other while the ether solvent is being distilled out.
    Type: Grant
    Filed: October 16, 1997
    Date of Patent: May 2, 2000
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Tsunemasa Ueno, Ikuyo Katsumi, Naoko Yamamoto, Hitoshi Mitsui
  • Patent number: 6054628
    Abstract: In a process for carrying out an exothermal reaction, selected from the addition reaction of organomagnesium halide compounds to carbonyl compounds and the ensuing hydrolysis of the addition product, a considerable fraction of the heat liberated during the reaction is removed by evaporation of the solvent.
    Type: Grant
    Filed: October 21, 1997
    Date of Patent: April 25, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Stroezel, Udo Rheude, Ralf-Thomas Rahn, Gerd Kaibel
  • Patent number: 5910605
    Abstract: The invention relates to a process for the preparation of 3-hydroxy-2-methylbenzoic acid and 3-acetoxy-2-methylbenzoic acid, which comprises reacting 3-chloro-2-methylphenol (3) with benzyl chloride to give 2-benzyloxy-6-chlorotoluene (4) subjecting this to a Grignard reaction with magnesium to give (3-benzyloxy-2-methylphenyl)magnesium chloride (5) reacting this with CO.sub.2 to give 3-benzyloxy-2-methylbenzoic acid (6) hydrogenating this or its alkali metal salts in the presence of a hydrogenation catalyst to give 3-hydroxy-2-methylbenzoic acid (2) and optionally acetylating this to give 3-acetoxy-2-methylbenzoic acid.
    Type: Grant
    Filed: February 6, 1998
    Date of Patent: June 8, 1999
    Assignee: Clariant GmbH
    Inventors: Robert Cosmo, Andreas Dierdorf
  • Patent number: 5852216
    Abstract: A method of preparing (3-alkoxyphenyl)magnesium chlorides and the use thereof for reaction with certain carbonyl compounds are described.
    Type: Grant
    Filed: February 14, 1997
    Date of Patent: December 22, 1998
    Assignee: Gruenenthal GmbH
    Inventors: Michael Finkam, Thomas Kohnen, Werner Winter
  • Patent number: 5792886
    Abstract: In producing (.+-.)-2-(6-methoxy-2-naphthyl)propionic acid or precursor thereof from 2-bromo-6-methoxynaphthalene, use is made of 2-bromo-6-methoxynaphthalene formed by (a) methylating 6-bromo-2-naphthol with methyl chloride in a solvent comprising one or more compounds, RZ, where R is a hydrogen atom or an alkyl group, and Z is --OH or --CN provided that if Z is --CN, R is alkyl, and in the presence of a strong base; and (b) recovering and purifying 2-bromo-6-methoxynaphthalene so formed.
    Type: Grant
    Filed: January 8, 1997
    Date of Patent: August 11, 1998
    Assignee: Albemarle Corporation
    Inventors: Mahmood Sabahi, Kevin J. Theriot, Brian F. Becnel
  • Patent number: 5779942
    Abstract: This dialkylmagnesium is represented by the formula R--(CH.sub.2 --CH.sub.2).sub.n --Mg--(CH.sub.2 --CH.sub.2).sub.n' --R', (E--O--E').sub.x, where R and R' each independently represent a C.sub.1 -C.sub.20 hydrocarbon residue, branched or not, substituted or not, of the alkyl, cycloalkyl or aralkyl type; n and n', identical or substantially identical, represent an average number of --CH.sub.2 --CH.sub.2 -- linkages such that the average number of carbon atoms in each of the two chains borne by Mg is greater than 20; E and E', identical or different, each represent an alkyl radical, linear or cyclical, branched or not; and 0.ltoreq.x.ltoreq.2, x being the average value of the number of moles of E--O--E' ether complexed to the dialkylmagnesium. In order to prepare a dialkylmagnesium of this type, ethylene is polymerized in an anhydrous, de-oxygenated hydrocarbonaceous solution by means of a catalyst Cp*.sub.2 MCl.sub.2 Li(OEt.sub.2).sub.
    Type: Grant
    Filed: April 5, 1996
    Date of Patent: July 14, 1998
    Assignees: Enichem S.p.A., Universite des Sciences et Technologies de Lille
    Inventors: Jean-Fran.cedilla.ois Pelletier, Karel Bujadoux, Xavier Olonde, Emmanuel Adisson, Andre Mortreux, Thomas Chenal
  • Patent number: 5744071
    Abstract: The present invention provides processes for making alkynyl ketones and precursors thereof, using less expensive reagents and/or hydrocarbon solvents and/or higher temperatures.
    Type: Grant
    Filed: November 19, 1996
    Date of Patent: April 28, 1998
    Assignee: FMC Corporation
    Inventors: Philip Franklin Sims, Anne Pautard-Cooper
  • Patent number: 5693261
    Abstract: Pentafluorophenylmagnesium halides are prepared by a Grignard exchange reaction of hydrocarbylmagnesium halide with pentafluorochlorobenzene. The pentafluorophenylmagnesium halides are converted to pentafluorophenyl metal or metalloid derivatives by reacting them with metal or metalloid halides such as BF.sub.3.
    Type: Grant
    Filed: August 9, 1995
    Date of Patent: December 2, 1997
    Assignee: Albemarle Corporation
    Inventors: Niomi L. Krzystowczyk, Steven P. Diefenbach, Wendy L. Lemoine
  • Patent number: 5474716
    Abstract: Disclosed are processes for the preparation of new bridged cyclopentadienylmagnesium compounds of the general formula Q(CpR.sub.a)(Cp'R'.sub.a ')Mg, and the use thereof for preparing bridged metallocenes.
    Type: Grant
    Filed: February 22, 1995
    Date of Patent: December 12, 1995
    Assignee: Witco GmbH
    Inventor: Richard Lisowsky
  • Patent number: 5453221
    Abstract: Disclosed are new bridged cyclopentadienylmagnesium compounds of the general formula Q(CpR.sub.a) (Cp'R'.sub.a')Mg, processes for the preparation thereof, and the use thereof for preparing bridged metallocenes.
    Type: Grant
    Filed: February 22, 1995
    Date of Patent: September 26, 1995
    Assignee: Witco GmbH
    Inventor: Richard Lisowsky
  • Patent number: 5362423
    Abstract: Disclosed is a production method, wherein, with pentafluorobenzene represented by C.sub.6 HF.sub.5, 0.5 to 1.5 equivalents of organometallic compound represented by a general formulaR.sub.2-n MgXn(wherein n denotes a real number of 0 or 1, X denotes a halogen atom, R denotes a hydrocarbon group with carbon atoms of 1 to 10, and said hydrocarbon group may contain functional groups unaffecting the reaction) are mixed within a temperature range from -40.degree. to 250.degree. C. in an ether type solvent or a mixed nonaqueous solvent of ether type solvent with hydrocarbon type solvent and reacted at 25.degree. C. or higher to obtain pentafluorophenylmagnesium derivatives represented by a following general formula(C.sub.6 F.sub.5).sub.2-n MgXn(wherein n denotes a real number of 0 or 1 and X denotes a halogen atom).
    Type: Grant
    Filed: December 20, 1993
    Date of Patent: November 8, 1994
    Assignee: Tosoh Akzo Corporation
    Inventors: Yoshihiko Ikeda, Takeo Yamane, Eiichi Kaji, Kenji Ishimaru
  • Patent number: 5358670
    Abstract: This invention relates to an alkyl Grignard reagents in diethylene glycol dibutyl ether. The invention also relates to a novel method for preparing Grignard reagents comprising reacting an alkyl halide with magnesium metal in the presence of diethylene glycol dibutyl ether. Grignard reagents prepared in the presence of diethylene glycol dibutyl ether have improved yields and stability, including storage stability, at room temperature. The Grignard reagents are prepared without the use of a low boiling and/or flammable stabilizing agents such as benzene, toluene, tetrahydrofuran, and diethyl ether.
    Type: Grant
    Filed: July 2, 1993
    Date of Patent: October 25, 1994
    Assignee: Ferro Corporation
    Inventors: Stanhope P. Turnbull, Charles R. Egedy
  • Patent number: 5273686
    Abstract: Organic-solvent soluble magnesium hydrides or formulas ##STR1## are prepared by catalytically hydrogenating finely powdered magnesium, optionally in the presence of a magnesium halide, in an organic solvent in the presence of their MgH.sub.2 -free counterparts in whichQ is an alkyl, alkenyl, alkoxy, dialkylamino, aralkyl, aryl or diarylamino group, each with up to 18 carbon atoms,R is an alkenyl, aralkyl or aryl group, each with up to 18 carbon atoms,X is chlorine, bromine, or iodine, ##STR2## is a chelating ligand, E is --CH.sub.2, --N(R)-- or --O--,is an alkylene radical of the formula --(CH.sub.2).sub.p,D is a dialkylamino, diarylamino or alkoxy group, each with up to 18 carbon atoms,M is aluminum or boron,m is 1, 2, or 3, and1<n.ltoreq.50.
    Type: Grant
    Filed: August 28, 1991
    Date of Patent: December 28, 1993
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Borislav Bogdanovic, Manfred Schwickardi
  • Patent number: 5242625
    Abstract: Process for the preparation of compounds of formula (I):Y--Mg--X (I)wherein Y is allyl, or an optionally substituted phenyl or optionally substituted benzyl group, and X is a halogen, by reaction of a compound of formula (II):Y--X (II)wherein Y and X have the meanings given above, with magnesium in tertiary-butylmethyl ether solvent, characterized in that the molar ratio of magnesium to compound of formula (II) is from 1:1 to 2:1 and the reaction is carried out at 45.degree. C. or above.
    Type: Grant
    Filed: December 10, 1992
    Date of Patent: September 7, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Raymond V. H. Jones, Robert C. Ewins, Robert M. Mellor
  • Patent number: 5209459
    Abstract: Process for the preparation of compounds of formula (I):Y--Mg--X (I)wherein Y is an optionally substituted phenyl or benzyl, and X is a halogen, by reaction of a compound of formula (II):Y--X (II)wherein Y and X have the meanings given above, with magnesium in a solvent, characterized in that the solvent is an acetal of formula (III): ##STR1## wherein R.sup.1 and R.sup.2 are independently alkyl having from 1 to 6 carbon atoms or when taken together form a dioxolane ring, and R.sup.3 is hydrogen or alkyl having from 1 to 6 carbon atoms.
    Type: Grant
    Filed: June 29, 1992
    Date of Patent: May 11, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Raymond V. H. Jones, John M. Bloomer
  • Patent number: 5171847
    Abstract: Novel metallo-organic complexes of the formula (M.sub.x X.sub.z. nL)y where M is an alkaline earth metal, a transition metal(at. Nos. 21-30, 39-48 and 72-80 inclusive) or a rare earth metal (at. Nos. 57-71 inclusive), X is an anion e.g. Cl.sup.-, Br.sup.-, NO.sub.3 -, NCS.sup.- etc. and L is a Lewis base, are prepared by reacting a source of the metal M under anhydrous conditions with an anhydrous ammonium salt of the anion X in the presence of the Lewis base, and cooling the reaction mixture to precipitate the complex.
    Type: Grant
    Filed: July 5, 1990
    Date of Patent: December 15, 1992
    Assignee: The Associated Octel Company Limited
    Inventors: Ronald Snaith, Dominic S. Wright, Alan T. Brooker, Simon R. Drake
  • Patent number: 5157149
    Abstract: A method of making substantially pure L-BPA is disclosed. The method includes the steps of reacting 4-bromobenzaldehyde with ethylene glycol to form 4-bromobenzaldehyde ethylene glycol acetal, sequentially reacting 4-bromobenzaldehyde ethyleneglycol acetal with Mg to produce the Grignard reagent and thereafter reacting with tributyl borate and then converting to an acid environment to form 4-boronobenzaldehyde, reacting 4-boronobenzaldehyde with diethanol amine to form 4-boronobenzaldehyde diethanolamine ester, condensing the 4-boronobenzaldehyde diethanolamine ester with 2-phenyl-2-oxazolin-5-one to form an azlactone, reacting the azlactone with an alkali metal hydroxide to form z-.alpha.-benzoylamino-4-boronocinnamic acid, asymmetrically hydrogenating the z-.alpha.
    Type: Grant
    Filed: June 4, 1991
    Date of Patent: October 20, 1992
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventor: Edward G. Samsel
  • Patent number: 5146001
    Abstract: In the preparation of benzyl ketones of the formula ##STR1## a benzyl chloride of the formula ##STR2## is reacted with an acid chloride of the formulaR.sup.6 --CO--Cl (III)a) in a first stage with an excess of zinc powder in the presence of a diluent at a temperature between 80.degree. C. and 200.degree. C. under an inert gas atmosphere, and separating off the excess zinc powder, thereby to obtain a benzyl derivative of the formula ##STR3## and b) in a second stage reacting the benzyl derivative of the formual (IV) with an acid chloride of the formula (III) in the presence of a palladium catalyst and in the presence of a diluent at a temperature between 0.degree. C. and 150.degree. C. under an inert gas atmosphere.
    Type: Grant
    Filed: June 3, 1991
    Date of Patent: September 8, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Thomas Himmler, Udo Kraatz, Wolfgang Kramer, Klaus Stroech
  • Patent number: 5141676
    Abstract: Organic-solvent soluble magnesium hydrides of the formulas(MgH.sub.2).sub.n. MgQ.sub.2 (II)(MgH.sub.2).sub.n. RMgX (III) ##STR1## are prepared by catalytically hydrogenating finely powdered magnesium, optionally in the presence of a magnesium halide, in an organic solvent in the presence of their MgH.sub.2 -free counterparts in whichQ is an alkyl, alkenyl, alkoxy, dialkylamino, aralkyl, aryl or diarylamino group, each with up to 18 carbon atoms,R is an alkenyl, aralkyl or aryl group, each with up to 18 carbon atoms,X is chlorine, bromine, or iodine,--E D.fwdarw. is a chelating ligand,E is --CH.sub.2, --N(R)-- or --O--,is an alkylene radical of the formula --(CH.sub.2).sub.p,D is a dialkylamino, diarylamino or alkoxy group, each with up to 19 carbon atoms,M is aluminum or boron,m is 1, 2, or 3, and1<n.ltoreq.50.
    Type: Grant
    Filed: April 17, 1991
    Date of Patent: August 25, 1992
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Borislav Bogdanovic, Manfred Schwickardi
  • Patent number: 5109043
    Abstract: A process for the preparation of organophosphorus derivatives of 2,4-di-tert-butylphenol with a high proportion of organophosphorus derivatives of biphenyl, which comprises reacting, in a first step, a 4,4'-dihalobiphenyl whose halogen has an atomic weight of at least 35, under Grignard conditions with magnesium to form the corresponding Grignard compound and this is further reacted in a second step with bis(2,4-di-tert-butylphenyl) chlorophosphite with the formation of a mixture in which at least 50% by weight of the phosphorus is combined in the form of tetrakis(2,4-di-tert-butylphenyl) 4,4'-biphenylenediphosphonite. The invention further relates to a polyolefin molding composition containing tetrakis(2,4-di-tert-butylphenyl) 4,4'-biphenylenediphosphonite which was prepared by reaction of a 4,4'-dihalobiphenyl whose halogen has an atomic weight of at least 35 with magnesium to form the Grignard compound and by subsequent reaction with bis(2,4-di-tert-butylphenyl) chlorophosphite.
    Type: Grant
    Filed: December 19, 1989
    Date of Patent: April 28, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Bohshar, Hans-Jerg Kleiner, Karl Waldmann, Gerhard Pfahler
  • Patent number: 5104997
    Abstract: This invention provides a process for deacidifying paper by contacting the paper with hydrocarbon or halocarbon solutions of certain magnesium and/or zinc alkoxyalkoxides which may have been treated with carbon dioxide to yield low viscosity solutions.
    Type: Grant
    Filed: December 20, 1990
    Date of Patent: April 14, 1992
    Assignee: FMC Corporation
    Inventors: Conard W. Kamienski, Robert S. Wedinger
  • Patent number: 5093046
    Abstract: Ethereal solutions of arylmethylmagnesium halidesAr--CH.sub.2 --Mg--Hal I(where Ar is unsubstituted or substituted aryl and Hal is Cl or Br) are prepared by the Grignard method from an arylmethyl halide IIAr--CH.sub.2 --Hal IIand magnesium in an ether IIItert-butyl--O--R III(where R is C.sub.1 -C.sub.3 -alkyl) as solvent.
    Type: Grant
    Filed: August 31, 1990
    Date of Patent: March 3, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Reiner Kober, Rainer Seele, Thomas Zierke, Heinz Isak, Stefan Karbach, Guenter Wegner
  • Patent number: 5091536
    Abstract: Organic-solvent soluble magnesium hydrides of the formulas ##STR1## are prepared by catalytically hydrogenating finely powdered magnesium, optionally in the presence of a magnesium halide, in an organic solvent in the presence of their MgH.sub.2 -free counterparts in whichQ is an alkyl, alkenyl, alkoxy, dialkylamide, aralkyl, aryl or diarylamide group, each with up to 18 carbon atoms,R is an alkenyl, aralkyl or aryl group, each with up to 18 carbon atoms,X is chlorine, bromine, or iodine,--E D.fwdarw. is a chelating ligand,E is --CH.sub.2, --N(R)-- or --O--,is an alkylene radical of the formula --(CH.sub.2).sub.p,D is a dialkylamide, diarylamide or alkoxy group, each with up to 18 carbon atoms,M is aluminum or boron,m is 1, 2, or 3, and1<n.ltoreq.50.
    Type: Grant
    Filed: February 9, 1988
    Date of Patent: February 25, 1992
    Assignee: Studiengesellschaft Kohle mbh
    Inventors: Borislav Bogdanovic, Manfred Schwickardi
  • Patent number: 5045244
    Abstract: A process for the preparation of an amine complex of a metal halide which comprises reacting said metal with an amine hydrohalide. The process can be extended to the use of metals such as aluminum, magnesium, zinc, iron, and the like.
    Type: Grant
    Filed: November 8, 1989
    Date of Patent: September 3, 1991
    Assignee: Ethyl Corporation
    Inventor: Everett M. Marlett
  • Patent number: 4837358
    Abstract: Process for the production of 9-alkenyl acetates is provided. The process comprises first disproportionating cyclooctene with an .alpha.-olefin to give a 1,9-alkadiene. The alkadiene is metallated to form a 1-metallo-9-alkene, which is then contacted with oxygen to produce a 9-alkenyl-1-oxymetallo compound, which is optionally hydrolyzed to the corresponding alcohol, with the alcohol being esterified to the desired 9-alkenyl ester or the 9-alkenyl-1-oxymetallo compound can be directly esterified, to produce the desired 9-alkenyl esters.
    Type: Grant
    Filed: February 26, 1986
    Date of Patent: June 6, 1989
    Assignee: Phillips Petroleum Company
    Inventors: Jim D. Byers, Charles A. Drake
  • Patent number: 4835316
    Abstract: Organgomagnesium complexes which correspond to the formula (I): ps(RMgX).sub.m /N[--CHR.sub.1 --CHR.sub.2 --O--(CHR.sub.3 --CHR.sub.4 --O).sub.n --R.sub.5 ].sub.3 (I)wherein:m is 1, 2, or 3;R denotes a substituted or unsubstituted group which is:linear or branched alkyl containing from 1 to 18 carbon atoms,alkenyl or alkynyl containing from 2 to 18 carbon atoms,cycloalkyl or cycloalkenyl containing from 3 to 12 carbon atoms,alkoxyalkyl, dialkoxyalkyl or alkylthiocarbonyl, aryl (which aryl may particularly be position-substituted by at least a halogen or an alkoxy, trifluoroemethyl, trifluoromethoxy or trifluromethoylthio group), oralkoxyaryl or alkylthioaryl;X denotes a chlorine, iodine or bromine atom;n is an integer ranging from 0 to about 10;R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which are identical or di fferent, denote a hydrogen atom or an alkyl or cycloalkyl radical containing from 1 to 4 carbon atoms; andR.sub.5, which is identical or different in each of the three [--CHR.sub.1 --CHR.sub.2 --O--(CHR.
    Type: Grant
    Filed: October 2, 1987
    Date of Patent: May 30, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Robert Corriu, Genevieve Cerveau, Claude Chuit, Catherine Reye, Alain Boudin
  • Patent number: 4731203
    Abstract: The present invention relates to a process for preparing a finely divided, highly reactive magnesium from magnesium hydride, magnesium anthracene and/or its derivatives or magnesium butadiene and/or its alkyl or phenyl derivatives, which process is characterized in that the respective magnesium-containing compound is thermally decomposed at a pressure from 10.sup.
    Type: Grant
    Filed: August 12, 1986
    Date of Patent: March 15, 1988
    Assignee: Studiengesellschaft Kohle mbH
    Inventor: Borislav Bogdanovic
  • Patent number: 4687867
    Abstract: Process for the production of the insect sex attractant, gossyplure, is provided. The process comprises first disproportionating 1,5-cyclooctadiene and 1-hexene to give 1,5,9-tetradecatriene, then metallating the triene to form a 1-metallo-5,9-tetradecadiene, and finally treating the organometal compound with a C.sub.2 -synthon to give directly 7,11-hexadecadienyl acetate or a substituted 7,11-hexadecadienyl moiety which can readily be converted to the desired acetate.
    Type: Grant
    Filed: April 14, 1986
    Date of Patent: August 18, 1987
    Assignee: Phillips Petroleum Company
    Inventors: Dennis S. Banasiak, Edward C. Mozdzen, Jim D. Byers
  • Patent number: 4616027
    Abstract: Compounds of the general formula ##STR1## or a pharmaceutically or agriculturally acceptable acid addition salt thereof wherein R is 5-chloro-2-pyridyl, phenyl or phenyl substituted by from one to three substituents, each independently selected from F, Cl, Br, I, CF.sub.3, (C.sub.1 -C.sub.4)alkyl and (C.sub.1 -C.sub.4)alkoxy; and n is zero or an integer from 1 to 5; method for their use in combatting fungal infections in plants, seeds and animals, including humans; and pharmaceutical and agricultural compositions containing them.
    Type: Grant
    Filed: July 25, 1983
    Date of Patent: October 7, 1986
    Assignee: Pfizer Inc.
    Inventors: Kenneth Richardson, Peter J. Whittle
  • Patent number: 4616026
    Abstract: Compounds of the formula ##STR1## a pharmaceutically or agriculturally acceptable acid addition salt thereof wherein R is 5-chloro-2-pyridyl, phenyl or phenyl substituted by from 1 to 3 substituents, each independently selected from F, Cl, Br, I, CF.sub.3, (C.sub.1 -C.sub.4)alkyl and (C.sub.1 -C.sub.4)alkoxy; and R.sup.1 is H, Cl, phenyl, phenyl substituted by from 1 to 3 substituents each independently selected from F, Cl, Br, I and CF.sub.3 or a heterocyclic group linked to the adjacent CF.sub.2 group by a ring carbon atom; method for their use in combatting fungal infections in plants, seeds and animals, including humans, and pharmaceutical and agricultural compositions containing them.
    Type: Grant
    Filed: July 25, 1983
    Date of Patent: October 7, 1986
    Assignee: Pfizer Inc.
    Inventors: Kenneth Richardson, Peter J. Whittle
  • Patent number: 4609498
    Abstract: Process for the production of the insect sex attractant, gossyplure, is provided. The process comprises first disproportionating 1,5-cyclooctadiene and 1-hexene to give 1,5,9-tetradecatriene, then metallating the triene to form a 1-metallo-5,9-tetradecadiene, and finally treating the organometal compound with a C.sub.2 -synthon to give directly 7,11-hexadecadienyl acetate or a substituted 7,11-hexadecadienyl moiety which can readily be converted to the desired acetate.
    Type: Grant
    Filed: March 14, 1985
    Date of Patent: September 2, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Dennis S. Banasiak, Edward C. Mozdzen, Jim D. Byers
  • Patent number: 4595783
    Abstract: The invention relates to intermediate compounds having the general formula I ##STR1## in which R.sup.1 is H, an alkyl, arylalkyl or an aliphatic acyl radical, preferably a benzyl or acetyl group and wherein X and Y together span an additional bond between the X and Y carrying C atoms (Ia) or in which Y is OH and X is H (Ib) and in which the dotted line can represent an additional bond particularly[2R,1'Z,3'E,7'E]-6-benzyloxy-2,5,7,8-tetramethyl-2-(4',8',12'-trimethyl-tri deca-1',3',7'-trien-1'-yl)chroman and6-benzyloxy-2,5,7,8-tetramethyl-2-(1'-hydroxy-4',8',12'-trimethyl-trideca-3 ',7'-diene-1'-yl)chroman, as well as compounds and methods of preparing compounds having the general formula II ##STR2## in which Z is one of the groups ##STR3## wherein R.sup.2 is an alkyl group with 1 to 4 carbon atoms preferably CH.sub.3 or C.sub.2 H.sub.
    Type: Grant
    Filed: August 31, 1984
    Date of Patent: June 17, 1986
    Inventors: Friedrich Vogel, Joachim Paust, Axel Nuerrenbach
  • Patent number: 4584307
    Abstract: A fungicidal agent of the formula: ##STR1## or a pharmaceutically or agriculturally acceptable salt thereof, wherein R is 5-chloropyrid-2-yl or a phenyl group optionally substituted by 1 to 3 substituents each independently selected from F, Cl, Br, I, CF.sub.3, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 alkoxy;and ##STR2## where n is 0, 1, 2 or 3 and R.sup.2 is H or C.sub.1 -C.sub.4 alkyl.
    Type: Grant
    Filed: July 16, 1984
    Date of Patent: April 22, 1986
    Assignee: Pfizer Inc.
    Inventors: Kenneth Richardson, Peter J. Whittle
  • Patent number: 4515709
    Abstract: A novel ternary intercalation compound of a graphite with an alkali metal fluoride and fluorine, which is represented by the formula C.sub.x F(MF).sub.y wherein M is an alkali metal is produced by reacting a graphite material with an alkali metal fluoride in an atmosphere of fluorine gas at a temperature of 0.degree. C. to 250.degree. C. for at least a period of time to effect a weight increase in the graphite. The ternary graphite intercalation compound thus obtained has not only an excellent stability to humidity or moisture but also a high electrical conductivity. The novel ternary graphite intercalation compound according to the present invention may be practically used as a novel electrically conductive material and a catalyst of organic reactions.
    Type: Grant
    Filed: March 9, 1983
    Date of Patent: May 7, 1985
    Assignee: Central Glass Co., Ltd.
    Inventors: Nobuatsu Watanabe, Tsuyoshi Nakajima, Masayuki Kawaguchi
  • Patent number: 4483862
    Abstract: Compounds of the formula ##STR1## or a pharmaceutically or agriculturally acceptable acid addition salt thereof wherein m and n are independently 0, 1, 2, 3 or 4; method for their use in combatting fungal infections in plants, seeds and animals, including humans; and pharmaceutical and agricultural compositions containing said compounds or salts.
    Type: Grant
    Filed: January 16, 1984
    Date of Patent: November 20, 1984
    Assignee: Pfizer Inc.
    Inventors: Kenneth Richardson, Peter J. Whittle
  • Patent number: 4477374
    Abstract: A novel ternary intercalation compound of a graphite with a metal fluoride and fluorine, which is represented by the formula C.sub.x F(MF.sub.z).sub.y wherein M is Al or Mg and z is an integer corresponding to the valence of M, is produced by contacting a graphite material with a metal fluoride selected from AlF.sub.3 and MgF.sub.2 in an atmosphere of fluorine gas at a temperature of 0.degree. C. to 400.degree. C. for at least a period of time to effect a weight increase in the graphite. The ternary graphite intercalation compound thus obtained has not only an excellent stability to humidity or moisture but also a high electrical conductivity. The novel ternary graphite intercalation compound according to the present invention may be practically used as a novel electrically conductive material and a catalyst of organic reactions.
    Type: Grant
    Filed: July 2, 1982
    Date of Patent: October 16, 1984
    Assignee: Central Glass Co., Ltd.
    Inventors: Nobuatsu Watanabe, Tsuyoshi Nakajima, Masayuki Kawaguchi
  • Patent number: 4474703
    Abstract: An organometallic halide having the formula:(RMX) (MX.sub.2).sub.a (MR.sub.2).sub.b (MH.sub.2).sub.cwherein a.ltoreq.0.45, b.ltoreq.0.15, and c.ltoreq.0.30, X is a halogen, R is a hydrocarbon radical, and M is a metal selected from the group consisting of magnesium, zinc, beryllium, and calcium is prepared by a continuous dry process by reacting an organic monohalide RX and a metal M in the form of convex solid grains of a size between 1 and 15 mm. The reaction temperature is lower than the temperature at which decomposition of the organometallic halide RMX begins and at least 10.degree. C. higher than the boiling point of the organic monohalide. The reaction may also take place in the presence of an organometallic derivative comprising a hydroxy group or an enolysable ketone group. The resulting organometallic halide may be used for the synthesis of anhydrous magnesium halide or for the reduction of titanium tetrachloride.
    Type: Grant
    Filed: September 22, 1982
    Date of Patent: October 2, 1984
    Assignee: Societe Chimique des Charbonnages-CdF Chimie
    Inventors: Karel Bujadoux, Jean-Marie Neyer, Jean-Pierre Houzeaux
  • Patent number: 4404216
    Abstract: 2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol and its pharmaceutically acceptable acid addition salts are disclosed. This particular bis-triazole derivative and its aforesaid salts are useful for treating fungal infections in animals, including humans. Methods for preparing these compounds from known starting materials are provided.
    Type: Grant
    Filed: June 1, 1982
    Date of Patent: September 13, 1983
    Assignee: Pfizer Inc.
    Inventor: Kenneth Richardson
  • Patent number: 4339392
    Abstract: A catalytic component having the formula(MX.sub.a) (MgX.sub.2).sub.b (RMgX).sub.c (MHgX).sub.dwherein M is a metal selected from group VI B and group V B of the Periodic Classification, X is a halogen, R is a hydrocarbon radical, 2.ltoreq.a .ltoreq.3.5, 1.ltoreq.b.ltoreq.30, 1.ltoreq.c.ltoreq.8 and 0.ltoreq.d.ltoreq.10 is prepared by reducing a metallic halide of the metal M, the valency of said metal being 4 if a metal of group IV B is concerned and 4 or 5 if a metal of group V B is concerned, by means of at least one organomagnesium compound having the formula RMgX, the said organomagnesium compound being used in the solid state and reduction of the metallic halide being carried out under a pressure lower than or equal to atmospheric pressure and at a temperature lower than the decomposition point of said organomagnesium compound under the pressure concerned but at least 10.degree. higher than the boiling point or sublimation point of the metallic halide under the pressure concerned.
    Type: Grant
    Filed: September 12, 1980
    Date of Patent: July 13, 1982
    Assignee: Societe Chimique des Charbonnages-CdF CHIMIE
    Inventor: Karel Bujadoux
  • Patent number: 4301166
    Abstract: The invention relates to hydroxyethyl-azole compounds and methods for their preparation. Also included in the invention are compositions containing said hydroxyethyl-azole compounds and methods for the use of said compounds and compositions as antimycotic agents.
    Type: Grant
    Filed: November 9, 1979
    Date of Patent: November 17, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Erik Regel, Karl H. Buchel, Ingo Haller, Manfred Plempel
  • Patent number: 4264518
    Abstract: Synthesis and intermediates for making an insect pheromone useful in the control of the San Jose scale, Quadraspidiotus perniciosus.
    Type: Grant
    Filed: October 30, 1978
    Date of Patent: April 28, 1981
    Assignee: Zoecon Corporation
    Inventors: Richard J. Anderson, Clive A. Henrick
  • Patent number: 4231896
    Abstract: Organomagnesium complexes, which have the formula:(R'.sub.2 Mg).sub.m .(RM).sub.nwherein RM is an organozinc or organoboron compound, R' is a primary alkyl or aryl group, and having an m:n ratio of about 1 or greater, are disclosed. These complexes are prepared by reacting magnesium with an organohalide selected from primary alkyl halides or aryl halides in the presence of a hydrocarbon solvent and subsequently adding an organozinc or organoboron compound. Alternately, the organozinc or organoboron compound can be generated in situ by adding a zinc or boron salt which is alkylated by the magnesium alkyl. The organozinc and organoboron compounds function as solubilizing agents for organomagnesium compounds which are normally only slightly soluble or insoluble in hydrocarbon media. These complexes are characterized by very low halide content, lack of ether contamination, magnesium to metal ratios of from about 1:1 to about 20:1, and hydrocarbon solubility. Even higher ratios are conceivably obtainable.
    Type: Grant
    Filed: June 12, 1978
    Date of Patent: November 4, 1980
    Assignee: Texas Alkyls, Inc.
    Inventor: Dennis B. Malpass
  • Patent number: 4217232
    Abstract: Compositions having highly effective antioxidant characteristics are provided comprising organic media, normally susceptible to oxidation, such as oils of lubricating viscosity, containing a minor amount sufficient to impart antioxidant properties thereto of the reaction product of a polysulfide and a hydrocarbylmagnesium halide or a Grignard reagent.
    Type: Grant
    Filed: December 21, 1978
    Date of Patent: August 12, 1980
    Assignee: Mobil Oil Corporation
    Inventor: Milton Braid
  • Patent number: 4187254
    Abstract: An organometallic halide having the formula:(RMX)(MX.sub.2).sub.a (MR.sub.2).sub.b (MH.sub.2).sub.cwherein a.ltoreq.0.45, b.ltoreq.0.15, and c.ltoreq.0.30, X is a halogen, R is a hydrocarbon radical, and M is a metal selected from the group consisting of magnesium, zinc, beryllium, and calcium is prepared by a continuous dry process by reacting an organic monohalide RX and a metal M in the form of convex solid grains of a size between 1 and 15 mm. The reaction temperature is lower than the temperature at which decomposition of the organometallic halide RMX begins and at least 10.degree. C. higher than the boiling point of the organic monohalide. The reaction may also take place in the presence of an organometallic derivative comprising a hydroxy group or an enolysable ketone group. The resulting organometallic halide may be used for the synthesis of anhydrous magnesium halide or for the reduction of titanium tetrachloride.
    Type: Grant
    Filed: November 2, 1977
    Date of Patent: February 5, 1980
    Assignee: Societe Chimique des Charbonnages - CdF Chimie
    Inventors: Karel Bujadoux, Jean-Marie Neyer, Jean-Pierre Houzeaux
  • Patent number: 4133824
    Abstract: Hydrocarbon soluble organo-magnesium complex of the formula(R.sub.2 'Mg).sub.m . [(RO).sub.a M].sub.nwherein R is a hydrocarbyl group or ##STR1## wherein R.sup.2 is a hydrocarbyl group. R' is a primary alkyl group having 1 to 25 carbon atoms, or phenyl group, or mixture thereof, M is a group IIA or group IIIA metal and a is 2 or 3, and m and n are numbers such that the ratio of m/n is about one or greater.These complexes are prepared by reacting magnesium metal with a primary alkyl halide or phenyl halide in the presence of a hydrocarbon solvent and adding thereto an oxygen containing metal compound of the formula (RO).sub.a M wherein R, M and a are as defined. The oxygen containing metal compound functions as a solubilizing agent for organo-magnesium compounds which are normally only slightly soluble in hydrocarbon media. These complexes are characterized by very low halide content, lack of ether contamination, magnesium to M ratios of between about 1:2 to about 20:1 and hydrocarbon solubility.
    Type: Grant
    Filed: August 17, 1977
    Date of Patent: January 9, 1979
    Assignee: Texas Alkyls, Inc.
    Inventors: Dennis B. Malpass, Joseph H. Merkley
  • Patent number: 4127507
    Abstract: A composition of matter comprising di-n-butylmagnesium and diethylmagnesium with a n-butyl:ethyl alkyl group ratio of about 0.25:1 to about 4:1 which is soluble in aliphatic, cycloaliphatic, and aromatic hydrocarbon solvents is disclosed. The composition is prepared in the substantial absence of oxygen and moisture by the simultaneous or consecutive reactions of ethyl and n-butyl halides with metallic magnesium in the presence of the hydrocarbon solvent, followed by separation of the insoluble magnesium chloride and any unreacted magnesium metal from the resulting solution.
    Type: Grant
    Filed: June 29, 1977
    Date of Patent: November 28, 1978
    Assignee: Texas Alkyls, Inc.
    Inventors: Loyd W. Fannin, Dennis B. Malpass
  • Patent number: 4105703
    Abstract: Process and apparatus for the production, in a continuous cycle, of cyclohexyl magnesium halides according to which cyclohexyl halide is fed from the bottom, at a constant rate, into a thermostatized column containing magnesium shavings fed from the top of the column itself, and the desired cyclohexyl magnesium halide is recovered in the top part of the column, the temperature of the column being kept at about 58.degree.-60.degree. C. and the cyclohexyl halide being fed in a solution of tetrahydrofuran.
    Type: Grant
    Filed: July 28, 1977
    Date of Patent: August 8, 1978
    Assignee: Oxon Italia S.p.A.
    Inventor: Raimondo Motta