Halogen Containing Patents (Class 568/655)
  • Patent number: 4453018
    Abstract: An alkylated phenolic ether is prepared by reacting in the absence of a protic solvent a phenolic compound containing an unreacted phenolic hydroxy group with an alkyl sulfite of the formula (RO).sub.2 SO in which R is a one to four carbon alkyl group, the reaction occurring in one step and without the intermediate preparation of a phenolate.
    Type: Grant
    Filed: April 1, 1982
    Date of Patent: June 5, 1984
    Assignee: International Telephone and Telegraph Corporation
    Inventor: Randall B. Nelson
  • Patent number: 4453017
    Abstract: A methylated phenolic ether is prepared by reacting in the absence of a protic solvent a phenolic compound containing an unreacted phenolic hydroxy group with trimethyl phosphate, the reaction occurring in one step and without the intermediate preparation of a phenolate.
    Type: Grant
    Filed: April 1, 1982
    Date of Patent: June 5, 1984
    Assignee: International Telephone and Telegraph Corporation
    Inventor: Randall B. Nelson
  • Patent number: 4424393
    Abstract: This invention relates to a process for preparing herbicidally active substituted diphenylethers. Also, this invention provides novel intermediates useful in the production of said diphenylethers.
    Type: Grant
    Filed: August 24, 1981
    Date of Patent: January 3, 1984
    Assignee: PPG Industries, Inc.
    Inventors: Frederick F. Guzik, Steven E. Pamer, Sidney B. Richter
  • Patent number: 4423249
    Abstract: Alkyl or aryl 1,1-difluoroalkyl ethers, e.g., 1,1,2-trifluoro-2-chloro-2-iodoethyl phenyl ether, are prepared by reacting an alkoxide or phenoxide with a 1,1-difluoro-1,2-dihaloethane (with the proviso that halo is not fluoro and at least one of the halo substituents is bromo or iodo) in an organic solvent at temperatures ranging from about -30.degree. C. to about 100.degree. C. These compounds may be dehalogenated with zinc to form the corresponding vinyl ethers.The reaction of halogen derivatives of fluorocarbons with nucleophiles is dramatically facilitated by a bromo or iodo substituent in the beta position.
    Type: Grant
    Filed: August 26, 1981
    Date of Patent: December 27, 1983
    Assignee: The Dow Chemical Company
    Inventors: William P. Carl, Bobby R. Ezzell
  • Patent number: 4412082
    Abstract: A novel process for preparing 4-hydroxyphenylacetic acid which is useful as an intermediate for pharmaceutical is provided. A method for preparing 4-hydroxyphenylacetic acid comprising the steps of first reacting benzyl phenyl ether with formaldehyde and hydrogen chloride to form 4-benzyloxybenzyl chloride, second reacting the resultant 4-benzyloxybenzyl chloride with an alkali metal cyanide in at least one solvent selected from the group consisting of water and an organic solvent to form 4-benzyloxyphenylacetonitrile, and hydrolyzing the resultant 4-benzyloxyphenylacetonitrile in the presence of an acid catalyst.
    Type: Grant
    Filed: March 2, 1982
    Date of Patent: October 25, 1983
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Motoo Mutsukado, Shin Yamada
  • Patent number: 4407760
    Abstract: A method for the preparation of difluoromethoxyaromatic compounds which are useful intermediates for the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric or superatmospheric pressures in the presence of a base, water, and an inert water miscible organic solvent mixture.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: October 4, 1983
    Assignee: American Cyanamid Company
    Inventor: Jack K. Siddens
  • Patent number: 4405640
    Abstract: Insecticides of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each selected from methyl, halomethyl, and halo; X is oxygen, sulphur, sulphonyl or a group NR.sup.4 where R.sup.4 represents hydrogen, lower alkyl or lower carboxylic acyl; R.sup.3 is lower alkyl, lower alkenyl or benzyl; m has the value zero or one, and n has a value from one to four.
    Type: Grant
    Filed: December 1, 1980
    Date of Patent: September 20, 1983
    Assignee: Imperial Chemical Industries PLC
    Inventor: Nazim Punja
  • Patent number: 4405529
    Abstract: A method for the preparation of certain difluoromethoxyaromatic compounds useful as intermediates in the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric or superatmospheric pressures in the presence of a base, water, and an inert water miscible organic solvent or solvent mixtures.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: September 20, 1983
    Assignee: American Cyanamid Company
    Inventors: Jack K. Siddens, Sivaraman Raghu
  • Patent number: 4404148
    Abstract: A method for the preparation of certain difluoromethoxyaromatic compounds which are useful intermediates for the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric and superatomspheric pressures in the presence of a base, acetone, benzyltriethylammonium chloride, and water.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: September 13, 1983
    Assignee: American Cyanamid Company
    Inventor: Jack K. Siddens
  • Patent number: 4380546
    Abstract: Azole compounds of the formula ##STR1## where X is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl or phenyl and m is an integer from 1 to 5, and, if m is greater than 1, the X's can be identical or different, n is an integer from 2 to 5, Z is N or CH and Y is CO or CR.sup.1 OR.sup.2, where R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.2 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkynyl or C.sub.1 -C.sub.4 -alkanoyl, and their crop-tolerated addition salts with acids, and metal complexes.The compounds act as fungicides and growth regulators.
    Type: Grant
    Filed: April 29, 1981
    Date of Patent: April 19, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Hubert Sauter, Eberhard Ammermann, Costin Rentzea, Bernd Zeeh, Johann Jung, Ernst-Heinrich Pommer
  • Patent number: 4377711
    Abstract: Disclosed are aromatic bromopolyfluoroalkyl ethers of the formula: ##STR1## where n is equal to 1 or 2 and R represents at least one moiety selected from the group consisting of hydrogen, the alkyl radicals having from 1 to 12 carbon atoms, the phenyl radical, the alkoxy radicals having from 1 to 12 carbon atoms, the phenyloxy radical, and the radicals NO.sub.2, CN, Cl, F, Br, I, CF.sub.3, and CONR.sub.1 R.sub.2 and NR.sub.1 R.sub.2 where R.sub.1 and R.sub.2 are identical or different and represent each a hydrogen or an alkyl radical having from 1 to 6 carbon atoms. Also disclosed is a method for preparation of these ethers. These compounds are useful as intermediates in producing products exhibiting phytosanitary or pharmaceutical activity.
    Type: Grant
    Filed: November 4, 1981
    Date of Patent: March 22, 1983
    Assignee: Rhone-Poulenc Industries
    Inventors: Isabelle Rico, Claude Wakselman
  • Patent number: 4375563
    Abstract: Compounds represented by the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are lower alkyl, R.sub.4 is lower alkoxy, R.sub.6 and R.sub.8 are methyl or trifluoro methyl, R.sub.9 is formyl, hydroxymethyl, alkoxymethyl, alkanoyloxymethyl, carboxyl, alkoxycarbonyl, lower alkenoxycarbonyl, lower alkynoxycarbonyl, carbamoyl, mono(lower alkyl)-carbamoyl, di(lower alkyl)carbamoyl or N-heterocyclylcarbonyl, R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 and R.sub.13 are hydrogen or fluorine with the proviso that at least one of R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 or R.sub.13 is fluorine or at least one of R.sub.6 or R.sub.8 is trifluoro methyl, or pharmaceutically acceptable salts thereof useful as antitumor agents are disclosed.
    Type: Grant
    Filed: March 30, 1982
    Date of Patent: March 1, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Ka-Kong Chan, Beverly A. Pawson
  • Patent number: 4350824
    Abstract: A process for the preparation of a 1,1-dichloroalkene of the formula ##STR1## in which R.sup.1 is hydrogen, or an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, orR.sup.1 and R.sup.2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain,comprising reacting a carbonyl compound of the formula ##STR2## with a trichloromethanephosphonic acid ester of the formula ##STR3## in which R.sup.3 each individually is an alkyl or phenyl radical, or the two radicals R.sup.3 together are alkanediyl,in the presence of at least an equimolar amount of a phosphorous acid triamide of the formulaP(NR.sup.4.sub.2).sub.3in whichR.sup.4 each independently is an alkyl radical, or the two radicals R.sup.4 together are alkanediyl.Advantageously,R.sup.1 is hydrogen,R.sup.2 a C.sub.2 to C.sub.
    Type: Grant
    Filed: February 23, 1981
    Date of Patent: September 21, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Jochem Riebel, Fritz Maurer, Uwe Priesnitz
  • Patent number: 4347148
    Abstract: Nitro phenols of the general formula ##STR1## wherein R is an aliphatic substituent of at least about 40 carbon atoms, a, b and c are, for example, each 1, 2 or 3, and Ar is an aromatic moiety such as a benzene nucleus, naphthalene nucleus or linked benzene nuclei, are useful additives for fuels and lubricants and intermediates to such additives. These nitro phenols can be conveniently prepared by nitrating appropriate phenols. Typically nitro phenols are formed by nitration of alkyl phenols having an alkyl group of at least about 50 carbon atoms.
    Type: Grant
    Filed: November 19, 1979
    Date of Patent: August 31, 1982
    Assignee: The Lubrizol Corporation
    Inventor: Kirk E. Davis
  • Patent number: 4334111
    Abstract: Benzotrihalides are prepared by pyrolyzing a substituted phenyl trihaloacetate of the formula ##STR1## wherein each X is halo, nitro, alkyloxy, aryloxy, aralkyoxy, cyano, lower alkyl, haloalkyl, haloalkyloxy, alkenyl, haloalkenyl, carbamoyl, N,N-dialkylcarbamoyl, N,N-diarylcarbamoyl, or N,N-diaralkyloxy;Y is halo; andn is an integer of from 1 to 5. As an example, 4-chlorophenyl trichloroacetate is pyrolyzed at 550.degree. C. to 4-chlorobenzotrichloride.
    Type: Grant
    Filed: February 17, 1978
    Date of Patent: June 8, 1982
    Assignee: The Dow Chemical Company
    Inventors: Ralph A. Davis, R. Garth Pews
  • Patent number: 4327025
    Abstract: A process for the preparation of a styrylcyclopropane-1-carboxylic acid ester of the formula ##STR1## in which R is C.sub.1-4 -alkyl or an alcohol radical customary in pyrethroids,R.sup.1 is alkoxy or alkylthio, either of which may be optionally substituted by halogen,R.sup.2 is hydrogen or alkoxy, orR.sup.1 and R.sup.2 together are optionally halogen-substituted alkylenedioxy, andR.sup.3 is hydrogen or chlorine,comprising reacting an ester of the formula ##STR2## in which Hal is chlorine or bromine,with a base.The compounds are insecticidally active. Numerous syntheses of the starting materials, some involving new intermediates, are also shown.
    Type: Grant
    Filed: April 7, 1980
    Date of Patent: April 27, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Jautelat, Dieter Arlt, Reinhard Lantzsch, Rainer Fuchs, Hans-Jochem Riebel, Rolf Schroder, Horst Harnisch
  • Patent number: 4315016
    Abstract: Fungicidal compounds of the formula: ##STR1## wherein R.sub.3 is hydrogen, R.sub.4 is phenyl optionally substituted with one halogen, and R.sub.5 is alkyl having up to 5 carbon atoms, alkenyl having up to 5 carbon atoms, alkynyl having up to 5 carbon atoms or monochlorophenoxymethyl or R.sub.5 is benzyl optionally ring substituted with up to three substituents selected from the class consisting of halogen, alkyl having up to 4 carbon atoms and alkoxy having up to 4 carbon atoms, or a fungicidal acid salt of such a compound.
    Type: Grant
    Filed: February 27, 1978
    Date of Patent: February 9, 1982
    Assignee: Imperial Chemical Industries Limited
    Inventors: Sugavanam Balassubramanyan, Margaret C. Shephard
  • Patent number: 4314086
    Abstract: Aliphatic/aromatic ethers are prepared by reacting an aliphatic halide with either an alkali or alkaline earth metal, or ammonium phenolate or naphtholate, in an inert organic solvent, and in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.
    Type: Grant
    Filed: June 20, 1980
    Date of Patent: February 2, 1982
    Assignee: Rhone-Poulenc Industries
    Inventors: Gerard Soula, Daniel Michelet
  • Patent number: 4306097
    Abstract: Cycloalkanones, cycloalkanols and unsaturated analogs thereof, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, their use for pharmacological and medicinal purposes, intermediates therefor and processes for their preparation.
    Type: Grant
    Filed: September 8, 1980
    Date of Patent: December 15, 1981
    Assignee: Pfizer Inc.
    Inventors: Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4284827
    Abstract: Substituted ethanes (I) are reacted with an alkyl metal reagent to form isomeric metalated olefins (IIIA and IIIB) having a trans (IIIB) to cis (IIIA) ratio of greater than 70:30.
    Type: Grant
    Filed: December 17, 1979
    Date of Patent: August 18, 1981
    Assignee: The Upjohn Company
    Inventor: Jerry A. Walker
  • Patent number: 4229470
    Abstract: Compounds are disclosed which have a juvenile hormone action on insects and also exhibit acaricide action. Said compounds are unsaturated aliphatic compounds having a trichloromethyl end group and the other end group of which is a phenol group which may be substituted and/or condensed, and which are capable of hindering the growth of insects from the larval to the adult stage and also exhibit an acaricide action on both adult acari and their eggs.
    Type: Grant
    Filed: January 17, 1979
    Date of Patent: October 21, 1980
    Assignee: Montedison S.p.A.
    Inventors: Paolo Piccardi, Angelo Longoni
  • Patent number: 4219677
    Abstract: A process for the telomerization of dienes with a telomerizing compound containing a mobile hydrogen atom is disclosed wherein the reaction between the diene and the telomerizing agent is effected in the presence of a catalytic system comprising a water-soluble sulfonated triaryl phosphine compound, preferably a water-soluble salt of a mono-, di-, or trisulfonated triphenyl phosphine and a transition metal compound, preferably palladium or a palladium-containing compound. Water is added either before or after the reaction is completed and the reaction products can easily be separated from the aqueous catalyst solution.
    Type: Grant
    Filed: July 19, 1978
    Date of Patent: August 26, 1980
    Assignee: Rhone-Poulenc Industries
    Inventor: Emile Kuntz
  • Patent number: 4213920
    Abstract: A process for the production of benzaldehydes which are substituted in the ortho-position by an electrophilic group R, which comprises brominating an ortho-substituted compound of the formula I ##STR1## in which R represents the nitro group, the cyano group, an alkoxy group of 1 to 8 carbon atoms or a halogen atom, under irradiation with visible light in an inert solvent, to give the bromide of the formula II ##STR2## converting the resulting bromide by treatment with an alkali bromide in an inert solvent into a styrene compound of the formula III ##STR3## and ozonising this latter compound in an inert solvent to give the compound of the formula IV ##STR4##
    Type: Grant
    Filed: June 28, 1978
    Date of Patent: July 22, 1980
    Assignee: Ciba-Geigy Corporation
    Inventor: Jacques Gosteli
  • Patent number: 4207266
    Abstract: This invention relates to a novel process for the direct trifluoromethylation of aromatic compounds via carbon tetrachloride and hydrogen fluoride in the presence of strong Bronsted or Lewis acids which give an acidic reaction (increase in concentration of H.sub.2 F.sup.+ ions) in anhydrous hydrogen fluoride.
    Type: Grant
    Filed: March 9, 1979
    Date of Patent: June 10, 1980
    Assignee: Rohm and Haas Company
    Inventor: Thomas R. Opie
  • Patent number: 4199595
    Abstract: The invention is m-phenoxybenzyl esters of 2-haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids which are useful insecticidal and acaricidal agents.
    Type: Grant
    Filed: March 20, 1978
    Date of Patent: April 22, 1980
    Assignee: American Cyanamid Company
    Inventors: Gerald Berkelhammer, Venkataraman Kameswaran
  • Patent number: 4188346
    Abstract: A process for the dehydrohalogenation of a (polyhaloalkyl)benzene containing a benzylic halogen such as 1,3-dichloro-5-(2,4,4,4-tetrachlorobutyl)benzene by contacting the (polyhaloalkyl)benzene with a suitably active Lewis acid catalyst such as SbCl.sub.5 or TiCl.sub.4 under conditions sufficient to catalyze said dehydrohalogenation to form a (polyhaloalkenyl)benzene such as 3,5-dichloro-.alpha.-(2,2,2-trichloroethyl)styrene.
    Type: Grant
    Filed: May 18, 1978
    Date of Patent: February 12, 1980
    Assignee: The Dow Chemical Company
    Inventor: Lowell D. Markley
  • Patent number: 4178460
    Abstract: The invention is 2-haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids which are useful intermediates in the preparation of insecticides of m-phenoxybenzyl and .alpha.-cyano-m-phenoxybenzyl esters.
    Type: Grant
    Filed: March 20, 1978
    Date of Patent: December 11, 1979
    Assignee: American Cyanamid Co.
    Inventors: Gerald Berkelhammer, Venkataraman Kameswaran
  • Patent number: 4174349
    Abstract: Fluoroorganic compounds are prepared by reacting a haloorganic starting material in which at least one halo atom is replaceable with a fluorine atom by metathetical exchange, with calcium fluoride in the presence of a crown ether and an anhydrous, polar, basic organic solvent which complexes with the calcium ion and contains no --OH groups, at a temperature and for a period of time adequate to effect fluorination.
    Type: Grant
    Filed: October 30, 1978
    Date of Patent: November 13, 1979
    Assignee: Allied Chemical Corporation
    Inventors: Francis E. Evans, Morris B. Berenbaum, Richard E. Eibeck, Martin A. Robinson
  • Patent number: 4164583
    Abstract: The present invention provides benz[f]isoindolines, useful in the treatment of aggression, a process for their preparation and compositions containing these compounds.
    Type: Grant
    Filed: June 22, 1978
    Date of Patent: August 14, 1979
    Assignee: Sandoz Ltd.
    Inventors: Roland Achini, Wolfgang Oppolzer, Emil Pfenninger
  • Patent number: 4163865
    Abstract: An improvement in a process for the preparation of a pinacol of the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and represent optionally substituted aliphatic, cycloaliphatic, araliphatic or an aromatic hydrocarbon radical by reducing a ketone of the formula ##STR2## wherein R.sup.1 and R.sup.2 have the abovementioned meanings with a base metal, the improvement comprising carrying out the reduction in the presence of an organic halogen compound and in the presence of a phosphoric acid amide, phosphoric acid ester and/or carboxylic acid amide.
    Type: Grant
    Filed: April 3, 1978
    Date of Patent: August 7, 1979
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinrich Wolfers, Hans Rudolph, Hans-Jurgen Rosenkranz
  • Patent number: 4158098
    Abstract: Polyalkoxy monovinyl substituted aromatic compounds, such as 3,4-dimethoxystyrene, function as both comonomer and randomizing agent in organolithium initiated copolymerization of a conjugated diene with a monovinyl aromatic compound, such as of butadiene with styrene. The resultant polymeric product exhibits lower levels of block styrene than does a corresponding copolymer made in the absence of the dimethoxystyrene.
    Type: Grant
    Filed: August 4, 1975
    Date of Patent: June 12, 1979
    Assignee: Phillips Petroleum Company
    Inventor: William J. Trepka
  • Patent number: 4154753
    Abstract: Surface-active products containing a highly fluorinated aliphatic substituent are prepared by nucleophilic attack of an oligomer of tetrafluoroethylene with an organic hydroxy compound in association with a proton acceptor.
    Type: Grant
    Filed: January 3, 1972
    Date of Patent: May 15, 1979
    Assignee: Imperial Chemical Industries Limited
    Inventor: Harold C. Fielding
  • Patent number: 4145362
    Abstract: A process for arylating an olefinic compound by addition of an aryl group to a double bond of said olefinic compound consisting in diazotizing an arylamine in an aqueous acidic solution comprising a lower alkanoic acid to form a solution of an aryldiazonium salt and reacting said aryldiazonium salt solution with an olefinic compound in an organic solvent in the presence of a catalytically effective amount of a copper halide.The amount of alkanoic acid is about 15 to 37% by volume of the total solvents used. The alkanoic acid is preferably acetic acid and the copper halide cuprous chloride.
    Type: Grant
    Filed: May 10, 1977
    Date of Patent: March 20, 1979
    Assignee: S.A. P R B en Neerlandais PRB N.V.
    Inventors: Joseph R. Brepoels, Jean-Marie Vaneghem
  • Patent number: 4126623
    Abstract: There are disclosed ethers and thioethers having a benzyl or phenyl terminal group and another terminal group which is halogenated, and which ethers and thioethers exhibit juvenile hormone activity (i.e., function as inhibitors of the development of insects from their larval state to the adult state), as well as acaricide activity.Methods for preparing the ethers and thioethers are also disclosed.
    Type: Grant
    Filed: April 14, 1977
    Date of Patent: November 21, 1978
    Assignee: Montedison S.p.A.
    Inventors: Paolo Piccardi, Pietro Massardo, Angelo Longoni