Halogen Containing Patents (Class 568/637)
  • Patent number: 4582944
    Abstract: A process for producing a hydroxydiphenyl ether, which comprises reacting at least one hydroquinone compound with itself or with a monohydric phenol compound in the presence of a catalyst composed essentially of a synthetic mica in which at least 10 mole % of cation-exchangeable interlayer cations are made up of a metal ion other than alkali metal ions, and/or a proton.
    Type: Grant
    Filed: May 3, 1984
    Date of Patent: April 15, 1986
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Katsuo Taniguchi, Hideo Nakamura, Terunori Fujita
  • Patent number: 4569943
    Abstract: The compound of the formula: ##STR1## wherein R.sub.1 is hydrogen, methyl or hydroxymethyl, R.sub.2 is hydrogen or methoxy, R.sub.3 is hydroxy or methoxy, and R.sub.4 is hydrogen or a group ##STR2## is novel, and the compound is of use as inhibitors of animal tissue fibrosis, or biochemical reagents.
    Type: Grant
    Filed: October 19, 1983
    Date of Patent: February 11, 1986
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hisayoshi Okazaki, Kazuhiko Ohta, Takenori Ishimaru
  • Patent number: 4570005
    Abstract: 2-Arylpropyl ether or thioether derivatives represented by the following general formula [I]: ##STR1## wherein Ar stands for an aryl group, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula [II]: ##STR2## or the following general formula [III]: ##STR3## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R.sup.1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R.sup.1 may be the same or different,are produced by reacting a compound represented by the following formula (V): ##STR4## with a compound represented by the following formula (VI):B--CH.sub.2 --D (VI)wherein Ar, R and B are defined above, A is a halogen atom and D is Y--H in which Y is as defined above,in the presence of a base in dimethylsulfoxide or sulfolane.
    Type: Grant
    Filed: July 14, 1983
    Date of Patent: February 11, 1986
    Assignee: Mitsuitoatsu Chemicals Inc.
    Inventors: Kiyoshi Nakatani, Satoshi Numata, Tsuneo Inoue, Kenji Kodaka, Tsutomu Ishii, Teruhiko Toyama, Hajime Tachibana, Takatoshi Udagawa, Masatoshi Gohbara
  • Patent number: 4562213
    Abstract: Ether compounds of the general formula, ##STR1## wherein W represents CH group or nitrogen atom, and (1) when W is the CH group,R.sub.1 represents hydrogen atom, fluorine atom, chlorine atom, bromine atom or methyl group, R.sub.2 represents hydrogen atom or fluorine atom, R.sub.3 and R.sub.4 are same or different and represent hydrogen atom, a halogen atom, a C.sub.1-4 alkyl, a C.sub.1-4 alkoxyl, difluoromethoxy or 2,2,2-trifluoroethoxy group, or represent, taken together, methylenedioxy group, A represents oxygen atom, methylene group or imino group, and when the A represents oxygen atom or methylene group, X and Y represent, taken together, ethylene group or 1,1-difluoroethylene group and when the A represents imino group, both X and Y represent methyl group or represent, taken together, ethylene group or 1,1-difluoroethylene group, and(2) when W is the nitrogen atom,both R.sub.1 and R.sub.2 represent hydrogen atom, R.sub.3 and R.sub.
    Type: Grant
    Filed: May 5, 1983
    Date of Patent: December 31, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Sumio Nishida, Noritada Matsuo, Kazunori Tsushima, Makoto Hatakoshi, Masachika Hirano
  • Patent number: 4547592
    Abstract: Arylether compounds containing terminal phenylethynyl groups are provided. Also provided is a process for producing these compounds. The following compounds are claimed; 4,4'-bis(3-phenylethynyl-phenoxy) diphenylsulfone; 2,2-bis[([([3-phenoxy]-3-phenoxy)-3-phenylethynyl]-3-phenoxy)-4-phenyl]-pr opane and 2,2-bis[([([3-phenoxy]-3-phenoxy)-3-phenyl ethynyl]-3-phenoxy)-4-phenyl]-hexafluoropropane.
    Type: Grant
    Filed: July 25, 1984
    Date of Patent: October 15, 1985
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Bruce A. Reinhardt, Fred E. Arnold, Marilyn R. Unroe
  • Patent number: 4542243
    Abstract: The present invention relates to a process for producing 3-phenoxybenzyl 2-(4-alkoxyphenyl)-2-methylpropyl ethers having excellent insecticidal and acaricidal activities which are represented by formula (IV): ##STR1## wherein R is a lower alkyl group and X.sub.1 and X.sub.2 are each a hydrogen or fluorine atom, which comprises reacting a 3-halogeno-4-alkoxyneophyl halide represented by the formula (I): ##STR2## wherein Y.sub.1 and Y.sub.2 are each a hydrogen, chlorine or bromine atom, at least one of them being a chlorine or bromine atom, R has the same meaning as above and X is a halogen atom, with a 3-phenoxybenzyl alcohol represented by the formula (II): ##STR3## wherein X.sub.1 and X.sub.2 have the same meaning as above, in the presence of a base to obtain a 3-phenoxybenzyl 2-(4-alkoxy-3-halogenophenyl)-2-methylpropyl ether represented by the formula (III): ##STR4## wherein Y.sub.1, Y.sub.2, R, X.sub.1 and X.sub.
    Type: Grant
    Filed: October 7, 1983
    Date of Patent: September 17, 1985
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Mitsumasa Umemoto, Tamotsu Asano, Teruyuki Nagata, Satoshi Numata
  • Patent number: 4542233
    Abstract: Improvement in the process for preparing biaryl compounds via coupling of an arylamine with an arene in the presence of a nitrite, an acid and copper metal or a derivative thereof; the improvement is consisting in adding to the reaction mixture a trialkylorthoformate. The process may be used for preparing drugs such as Flurbiprofen and Xenbucin or intermediate compounds particularly useful for preparing Flurbiprofen, Flufenisal, Chlordimorin, Xenbucin, Xenysalate, Xenyhexenic acid and the like.
    Type: Grant
    Filed: July 20, 1983
    Date of Patent: September 17, 1985
    Assignee: Biaschim S.p.A.
    Inventors: Oreste Piccolo, Aldo Belli, Giovanni Villa, Enrico Zen, Attilio Citterio
  • Patent number: 4518788
    Abstract: Aromatic polyvinylethers and active hydrogen compound reaction products thereof have been found to provide fast heat curable molding compositions when used with various heat activated curing catalysts, for example, diaryliodonium salts in combination with aromatic polyvinylether soluble copper compounds, or dialkylhydroxyarylsulfonium salts in combination with certain organic oxidants.
    Type: Grant
    Filed: January 20, 1983
    Date of Patent: May 21, 1985
    Assignee: General Electric Company
    Inventor: James V. Crivello
  • Patent number: 4490562
    Abstract: A very pure, dust-free commercial form of 4,2',4'-trichloro-2-hydroxydiphenyl ether with little odor is prepared by diazotizing 4,2'4'-trichloro-2-aminodiphenyl ether, boiling the diazonium salt and purifying the reaction product.
    Type: Grant
    Filed: January 31, 1983
    Date of Patent: December 25, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Werner Schreiber, Michael Marky
  • Patent number: 4486610
    Abstract: A process is described for purifying the bacteriostat 2,4,4'-trichloro-2'-hydroxydiphenylether prepared by the diazotization of 2,4,4'-trichloro-2'-aminodiphenylether from the 2,4,8-trichlorodibenzofuran and associated nonphenolics which form. A selective solvent extraction for these non-phenolics consisting of tetrachlorethylene is used after neutralization of the hydrolyzed diazo product.
    Type: Grant
    Filed: February 7, 1983
    Date of Patent: December 4, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Richard B. Lund
  • Patent number: 4467117
    Abstract: An improved synthesis of the bacteriostat 2,4,4'-trichloro-2'-hydroxydiphenylether is disclosed wherein the hydrolysis after diazotization is carried out at 175.degree.-180.degree. C. to increase the yield and reaction rate. The hydrolyzed product is distilled after neutralization to remove the major portion of undesirable colored products and phenolics. The distillate is then extracted with tetrachlorethylene to separate the product from non-phenolic by-products including the 25-28% 2,4,8-trichlorodibenzofuran which are present. The final product of the process then meets F.D.A. and commercial standards for use in soaps and cosmetics.
    Type: Grant
    Filed: February 7, 1983
    Date of Patent: August 21, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Richard B. Lund, Glenn W. Brown
  • Patent number: 4450308
    Abstract: New process for the preparation of known trifluoromethylphenyl oxyphenyl ether compounds of the formula ##STR1## wherein X stands for fluorine, chlorine or bromine andR for moieties, substituted if desired, of the series alkyl, alkenyl and alkinyl,by reacting 1,2-dihalogen-4-trifluoromethylbenzenes of the formula ##STR2## in which X and X.sup.1 independently of one another stand for fluorine, chlorine or bromine,with phenols of the formula ##STR3## in which R has the meaning given above, and basic alkali or alkaline earth compounds or with the salts formed from the phenols of formula (III) and the basic alkali or alkaline earth compounds, in the presence of diluents at temperatures between 60.degree. and 120.degree. C.The compounds of the formula (I) are intermediates for the synthesis of herbicides.
    Type: Grant
    Filed: November 30, 1981
    Date of Patent: May 22, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Uwe Priesnitz
  • Patent number: 4419123
    Abstract: The herbicidal-4-trifluoromethyl-3'-carbon-substituted-4'-substituted diphenyl ethers comprise a class of compounds that are highly effective herbicides.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: December 6, 1983
    Assignee: Rohm and Haas Company
    Inventor: Colin Swithenbank
  • Patent number: 4419124
    Abstract: The herbicidal 4-trifluoromethyl-3'-nitrogen-substituted-4'-substituted diphenyl ethers comprise a class of compounds that are highly effective herbicides.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: December 6, 1983
    Assignee: Rohm and Haas Company
    Inventor: Colin Swithenbank
  • Patent number: 4419122
    Abstract: The herbicidal 4-trifluoromethyl-3'-oxygen-substituted-4'-substituted diphenyl ethers comprise a class of compounds that are highly effective herbicides.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: December 6, 1983
    Assignee: Rohm and Haas Company
    Inventor: Colin Swithenbank
  • Patent number: 4399075
    Abstract: Phenoxytoluene derivative is chlorinated in a very high yield and selectivity in the presence of nitrogen-, sulfur-, phosphorus- or oxygen-containing compound which is capable of forming a charge-transfer complex with chlorine, chlorine radical or organic halogen compound, together with radical initiator and organic halogen compound.
    Type: Grant
    Filed: June 25, 1981
    Date of Patent: August 16, 1983
    Assignee: Asahi Chemical Company, Limited
    Inventors: Zenichi Yoshida, Susumu Kato, Takuya Fujiki, Yasuhiro Amemiya
  • Patent number: 4397864
    Abstract: The present invention relates to 2-arylpropyl ether or thioether derivatives represented by the following general formula [I]: ##STR1## wherein Ar stands for an aryl group, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula [II]: ##STR2## or the following general formula [III]: ##STR3## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R.sup.1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R.sup.1 may be the same or different, and also to processes for the preparation or these ethers of thioethers and a use of these ethers or thioethers.These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicity of these compounds are very low.
    Type: Grant
    Filed: April 14, 1981
    Date of Patent: August 9, 1983
    Assignee: Mitsuitoatsu Chemicals Inc.
    Inventors: Kiyoshi Nakatani, Satoshi Numata, Tsuneo Inoue, Kenji Kodaka, Tsutomu Ishii, Teruhiko Toyama, Hajime Tachibana, Takatoshi Udagawa, Masatoshi Gohbara
  • Patent number: 4393079
    Abstract: Anti-inflammatory compositions are prepared which comprise a therapeutically effective amount of a compound of the formula ##STR1## wherein X is CO or CHOH; Y is CO; the dotted line represents a double bond which is present or absent; R.sub.1 is hydrogen or methyl; R.sub.2 is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxyl, hydroxyl, acetoxyl, nitro or amino; R.sub.3 is alkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkenyl of 3 to 8 carbon atoms, cycloalkenyl of 5 to 8 carbon atoms or phenyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxyl, ethoxyl, benzyloyl, hydroxyl, acetoxyl, trifluoromethyl, nitro, amino, acetyl, methylthiol, methylsulphonyl, methylamino and dimethylamino. Compounds of formula I above are also novel.
    Type: Grant
    Filed: December 15, 1976
    Date of Patent: July 12, 1983
    Assignee: Beecham Group Limited
    Inventors: William G. Cole, Alexander C. Goudie, Carl J. Rose
  • Patent number: 4391995
    Abstract: Novel 4-phenoxy-phenoxy-alkane-carboxylic acid derivatives of the formula I ##STR1## in which R.sub.1 stands for hydrogen, methylithio, cyclopentyl, cyclohexyl, phenyl, methylcycylohexyl, ethylcyclohexyl, or R.sub.1 and R.sub.3 together stand for a --CH.dbd.CH--CH.dbd.CH-- bridge or--unless at least one of the substituents R.sub.2 to R.sub.8 stands for hydrogen, or if R.sub.9 stands for a radical having at least 2 carbon atoms--for chlorine,R.sub.2 and R.sub.3, independent of one another, each stands for hydrogen, chlorine or alkyl of 1 to 4 carbon atoms,R.sub.4 stands for hydrogen, chlorine, alkyl of 1 to 4 carbon atoms, cyclopentyl, cyclohexyl, methylcyclohexyl or R.sub.3 and R.sub.4 together stand for a --CH.dbd.CH--CH.dbd.CH-- bridge,R.sub.5, R.sub.6 and R.sub.7, independent of one another, each stands for hydrogen or alkyl of 1 to 4 carbon atoms,R.sub.8 stands for hydrogen, alkyl of 1 to 4 carbon atoms or allyl,R.sub.
    Type: Grant
    Filed: May 21, 1981
    Date of Patent: July 5, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Nahm, Ernold Granzer
  • Patent number: 4381412
    Type: Grant
    Filed: August 4, 1981
    Date of Patent: April 26, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel, Erich Klauke
  • Patent number: 4377712
    Abstract: A process for the preparation of meta-substituted diaryl ethers comprises reacting an ortho-haloaryl compound with a phenol compound in a non-aqueous medium in the presence of an alkaline metal base. In a specific embodiment m-phenoxytoluene is prepared by reacting orthochlorotoluene with phenol in the presence of an alkaline metal hydroxide in a substantially non-aqueous liquid medium.
    Type: Grant
    Filed: February 23, 1981
    Date of Patent: March 22, 1983
    Assignee: Occidental Chemical Corporation
    Inventors: Arthur M. Foster, James J. Maul
  • 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: 4374281
    Abstract: Hydroquinone-monophenyl ethers and their alkali metal salts of the formula ##STR1## (R=H or alkali) are obtained by reacting compounds of the formula ##STR2## with an excess of a compound of the formula ##STR3## (Kat=Na, K) in N-methylpyrrolidone at 230.degree.-260.degree. C.
    Type: Grant
    Filed: May 8, 1981
    Date of Patent: February 15, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Reinhart Geuss
  • Patent number: 4370277
    Abstract: Compounds of the formula: ##STR1## in which R.sup.1 is H, halogen, alkyl or alkoxy; R.sup.2 is H, halogen, alkyl or CF.sub.3 ; R.sup.3 is H, Cl, Br, alkyl or CN; R.sup.4 is H, halogen, alkyl, phenyl or halophenyl; and R.sup.5 is H, alkyl, alkinyl or CN; are starting materials for the manufacture of valuable insecticides of the pyrethroid type.
    Type: Grant
    Filed: October 26, 1981
    Date of Patent: January 25, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Welter, Hilmar Mildenberger
  • Patent number: 4360375
    Abstract: A herbicidal composition which comprises a phenoxyphenoxy unsaturated derivative having the formula: ##STR1## wherein X represents a halogen atom or CF.sub.3 ; Y represents a hydrogen atom or a halogen atom; and Z represents --COOR, --COR", --COOH, --CH.sub.2 OH, or --CH.sub.2 OR"'.
    Type: Grant
    Filed: December 23, 1980
    Date of Patent: November 23, 1982
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Kazuo Jikihara, Shigekazu Itoh, Shuichi Takayama, Koichi Sato, Ichiro Kimura, Isao Chiyomaru
  • Patent number: 4356329
    Abstract: There are disclosed two hydroquinone diethers having at least one acetylenic and halogen-substituted chain and exhibiting juvenile hormone and acaricide activity and which show unexpected activity on Tenebrio molitor and Tribolium confusum.The two hydroquinone ethers are obtained by:(a) reacting one mole of hydroquinone alkali metal salt with two moles of 1,5-dichloropent-4-yne, or equimolar quantities of an alkali metal salt of 4-phenoxy-phenol with 1,5-dichlorpent-4-yne; or(b) by reacting the hydroquinone alkali metal salt or the 4-phenoxy-phenol alkali metal salt with the indicated quantities of 1,1,1,5-tetrachloropentane and then dehydrohalogenating the condensation product with alkali metal carbonates or hydroxides in dimethylsulphoxide.
    Type: Grant
    Filed: October 20, 1980
    Date of Patent: October 26, 1982
    Assignee: Montedison S.p.A.
    Inventors: Franco Bettarini, Pietro Massardo, Paolo Piccardi, Angelo Longoni
  • Patent number: 4355189
    Abstract: Process for the preparation of 4-phenoxyphenols of the formula ##STR1## in which R.sup.1 through R.sup.5 are hydrogen, halogen or alkyl, by diazotization of amines of the formula ##STR2## in a hydrochloric acid medium, and boiling in aqueous sulfuric acid at 110.degree. to 150.degree. C.
    Type: Grant
    Filed: February 6, 1981
    Date of Patent: October 19, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gert Volkwein, Hubert Schonowsky, Konrad Baessler
  • Patent number: 4355186
    Abstract: Substituted 4-phenoxy-phenols are prepared by adding the corresponding anilines in liquid or molten state together with aqueous sodium nitrite solution in equimolar amounts to excess HCl and introducing the diazonium chloride solution obtained into a boiling mixture of about half-concentrated H.sub.2 SO.sub.4 and an aromatic hydrocarbon.
    Type: Grant
    Filed: June 25, 1981
    Date of Patent: October 19, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Werner Becker, Klaus Dehmer, Klaus Kaiser, Karl Rehn
  • Patent number: 4349567
    Abstract: Cyclopropanecarboxylic acid esters of the formula ##STR1## wherein R.sub.1 is hydrogen, halogen, methyl, trifluoromethyl or methoxy, and X.sub.1 and X.sub.2 are each halogen.A process for producing the above compounds and their use in pest control, as well as .alpha.-haloethynyl-3-phenoxy-benzyl alcohols.
    Type: Grant
    Filed: August 4, 1980
    Date of Patent: September 14, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Ackermann, Jozef Drabek, Saleem Farooq, Laurenz Gsell, Odd Kristiansen, Rudolf Wehrli
  • Patent number: 4348408
    Abstract: The invention describes cyclopropanecarboxylic acid .alpha.-allenyl-3-phenoxybenzyl esters of the formula ##STR1## wherein X.sub.1 is halogen and each of Y.sub.1 and Y.sub.2 is hydrogen or halogen, a process for the production of these compounds, and the use thereof for controlling a variety of pests of animals and plants. The intermediates of the formula ##STR2## wherein X is hydroxyl or halogen and each of Y.sub.1 and Y.sub.2 is hydrogen or halogen, are also described.
    Type: Grant
    Filed: August 12, 1981
    Date of Patent: September 7, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Ackermann, Laurenz Gsell, Rudolf Wehrli
  • Patent number: 4339612
    Abstract: 3,3-Dimethyl-1-phenoxy-butan-2-ols of the formula ##STR1## in which Y is a halogen atom, an optionally substituted phenyl radical, an optionally substituted phenoxy radical or a nitro, cyano, alkyl, alkoxy, alkoxycarbonyl or cycloalkyl radical, and n is 0, 1, 2 or 3,exhibit plant growth stimulating properties and are also useful in the synthesis of known fungicides. They are produced from tert-butyloxirane and the corresponding phenols.
    Type: Grant
    Filed: February 13, 1981
    Date of Patent: July 13, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Eckart Kranz, Peter Siegle
  • Patent number: 4338468
    Abstract: .alpha.-Prop-1-ynyl-3-phenoxybenzyl alcohols of the formula ##STR1## wherein Y represents hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, cyano or dimethylamino, a process for their manufacture and their use as intermediates for the synthesis of compounds which are suitable for pest control, and which are especially suitable because of their low fish toxicity, for the control of rice pests e.g. Chilo suppressalis in rice paddies where fish are kept.
    Type: Grant
    Filed: December 9, 1980
    Date of Patent: July 6, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Saleem Farooq, Peter Ackermann, Jozef Drabek, Laurenz Gsell, Odd Kristiansen, Rudolf Wehrli
  • Patent number: 4335055
    Abstract: Compounds of the formula I ##STR1## in which Z, Z.sub.1, R, m and p are as defined in patent claim 1, can be obtained in a simple and economical manner by a novel process wherein a halide of the formula II ##STR2## is reacted with a substituted or unsubstituted vinylbenzene or vinylnaphthalene derivative in the presence of a base and of certain palladium catalysts, such as palladium acetate. The compounds (I) or functional derivatives preparable therefrom are useful, for example, for the preparation of known dyes or fluorescent brighteners, or can be used directly as fluorescent brighteners or as scintillators.
    Type: Grant
    Filed: May 8, 1981
    Date of Patent: June 15, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ulrich Blaser, Dieter Reinehr, Alwyn Spencer
  • 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: 4331682
    Abstract: Cyclopropanecarboxylic acid-.alpha.-haloethynyl-m-phenoxybenzyl esters of the formula ##STR1## wherein R.sub.1 is ##STR2## R.sub.2 is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl or methoxy, andX.sub.1 is halogen,processes for producing them, and their use for combating insect pests.
    Type: Grant
    Filed: March 2, 1981
    Date of Patent: May 25, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Ackermann, Jozef Drabek, Saleem Farooq, Laurenz Gsell, Odd Kristiansen, Rudolf Wehrli
  • Patent number: 4322442
    Abstract: 1-Halo-1-propyn-3-ols of the formula ##STR1## in which R is optionally substituted phenyl, pyridyl, furyl, thienyl or pyrazolyl,R' is optionally substituted phenyl, andX is halogen,which possess fungicidal properties.
    Type: Grant
    Filed: September 8, 1980
    Date of Patent: March 30, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Jager, Erich Klauke, Wilhelm Brandes, Paul-Ernst Frohberger
  • Patent number: 4316993
    Abstract: Diazotization of 4-phenoxy-anilines in aqueous sulfuric acid of 60 to 75% strength and decomposition of the resulting diazonium compound in sulfuric acid of the same concentration range yields the corresponding phenols in high yields and quality. These phenols are intermediate for the corresponding 4-phenoxy-phenoxy alkane carboxylic acids which are pharmaceuticals capable of reducing the blood serum lipid level.
    Type: Grant
    Filed: February 28, 1980
    Date of Patent: February 23, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Emmerich Paszthory, Karl G. Seifert, Vincenz Zimmermann, Hans J. Nestler
  • Patent number: 4310702
    Abstract: Sulfuryl chloride is reacted in the liquid phase with an organic reactant which is a ketone or aromatic alcohol unsubstituted on both ortho carbons in the presence of a moderator selected from the group consisting of aliphatic alcohols of 1-3 carbons and aliphatic ethers of 2-6 carbons, with sufficient moderator being present to selectively produce a product substantially free of compounds with more than one chlorine atom per carbonyl or aromatic hydroxy. The products, such as monochloroacetone, monochlorocyclohexanone, monochlorophenol and 2,2-bis(3-chloro-4-hydroxyphenyl)propane, are useful as chemical intermediates and as monomers for flame retardant polymers.
    Type: Grant
    Filed: July 28, 1980
    Date of Patent: January 12, 1982
    Assignee: Allied Corporation
    Inventors: Divakaran Masilamani, Milorad M. Rogic
  • Patent number: 4306094
    Abstract: Substituted and unsubstituted 1,4-dihydroxybenzenes are reacted in the presence of a cation exchange resin catalyst and an inert solvent to form the corresponding 4,4'-dihydroxydiphenyl ethers.
    Type: Grant
    Filed: January 18, 1980
    Date of Patent: December 15, 1981
    Assignee: E. I. Du Pont de Nemours & Co.
    Inventor: Raymond J. Shozda
  • Patent number: 4301304
    Abstract: Cyclopropanecarboxylic acid-phenoxy-.alpha.-vinyl-benzyl esters of the formula ##STR1## in which Y is chlorine or bromine, and R.sub.1 is --CH.dbd.CH.sub.2 or ##STR2## processes for producing them, and their use in combating pests.
    Type: Grant
    Filed: April 18, 1980
    Date of Patent: November 17, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Jozef Drabek, Peter Ackermann, Saleem Farooq, Laurenz Gsell, Odd Kristiansen
  • Patent number: 4301088
    Abstract: A method for preparing benzyl alcohols or substituted benzyl alcohols is disclosed by decarbonylation of formic acid esters of benzyl alcohols or ring substituted benzyl alcohols, the decarbonylation being carried out in the presence of a catalyst.
    Type: Grant
    Filed: June 6, 1979
    Date of Patent: November 17, 1981
    Assignee: Dynamit Nobel AG
    Inventor: Gunther Bernhardt
  • Patent number: 4291177
    Abstract: Highly pure dihalodiphenols or predetermined, statistical mixtures of unreacted, monohalo- and dihalodiphenols are obtained reacting the diphenol, which is suspended or dissolved in a suitable solvent, with a halogen while concurrently purging the reaction with a gas that is inert to the reaction.
    Type: Grant
    Filed: December 6, 1979
    Date of Patent: September 22, 1981
    Assignee: General Electric Company
    Inventors: Victor Mark, Charles A. Wilson, II
  • Patent number: 4288386
    Abstract: The Ullman reaction for the preparation of diaryl ethers by coupling aryl halides with metal phenolates is conducted 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: May 12, 1980
    Date of Patent: September 8, 1981
    Assignee: Rhone-Poulenc Industries
    Inventors: Gerard Soula, Louis Linguenheld
  • Patent number: 4287125
    Abstract: Benzenoid ethers/thioethers are prepared by reacting an activated halobenzene with an anionic reactant, RA.sup.- M.sup.+, in the presence of at least one tertiary amine sequestering agent having 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: September 1, 1981
    Assignee: Rhone-Poulenc Industries
    Inventor: Gerard Soula
  • Patent number: 4284828
    Abstract: A process for the manufacture of 4,5-dichloro-2-(4-chlorophenoxy)phenol by selective chlorination of 2-phenoxyanisole with 3 to 5 molar equivalents of chlorine, in the temperature range between -10.degree. and +50.degree. C., preferably between 0.degree. and 30.degree. C., in a lower halogenated aliphatic hydrocarbon, a lower aliphatic nitrile, in dimethyl formamide, dimethylmethanephosphonate or methanol, preferably in dimethyl formamide, dimethylmethanephosphonate, methanol, acetonitrile, propionitrile, chloroform, methylene chloride, 1,2-dichloroethane or tetrachloroethane, and demethylation of the 4,5-dichloro-2-(4-chlorophenoxy)anisole obtained as intermediate with an acid.
    Type: Grant
    Filed: November 9, 1979
    Date of Patent: August 18, 1981
    Assignee: Ciba-Geigy Corporation
    Inventor: Claus D. Weis
  • Patent number: 4283565
    Abstract: There is described an essentially two step process for the preparation of benzylalcohols including those benzylalcohols having substituents on the benzyene ring by reaction of a substituted or unsubstituted benzyl halide with a formate typically an alkali or alkaline earth metal formate to form the corresponding substituted or unsubstituted benzyl formate. In the second step of the process the benzyl formate is contacted with an alcohol whereby the same is converted into the desired benzylalcohol. Both steps can be performed employing catalysts. Described in the specification is the realization of the desired product in exceptionally high yields in a short period of time whereby the process is characterized by high space-time yields.
    Type: Grant
    Filed: December 29, 1978
    Date of Patent: August 11, 1981
    Assignee: Dynamit Nobel AG
    Inventors: Gunther Bernhardt, Gerhard Daum
  • Patent number: 4283566
    Abstract: An improved process for obtaining halogenated diphenols which can be pure dihalodiphenols or predetermined, statistical mixtures comprising unreacted diphenol, monohalodiphenols and dihalodiphenols.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: August 11, 1981
    Assignee: General Electric Company
    Inventor: Victor Mark
  • Patent number: 4282388
    Abstract: Novel benzyl ethers of cyclic 1,1-diols, of the formula ##STR1## wherein R.sup.1 is phenyl or substituted phenyl,R.sup.2 is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl or --CHX--R.sup.1,X is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, phenyl or substituted phenyl,Y and Y' are individually selected from hydrogen, alkyl, phenyl and substituted phenyl andA is saturated or unsaturated alkylene or substituted alkylene;have been found outstandingly effective as herbicides, particularly as selective herbicides.
    Type: Grant
    Filed: November 28, 1978
    Date of Patent: August 4, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilfried Draber, Wolf Reiser, Thomas Schmidt, Ludwig Eue, Robert R. Schmidt
  • Patent number: 4282391
    Abstract: A continuous process for obtaining highly pure, high molecular weight aromatic polycarbonates from highly pure, halogenated diphenols.
    Type: Grant
    Filed: December 10, 1979
    Date of Patent: August 4, 1981
    Assignee: General Electric Company
    Inventors: Clayton B. Quinn, Charles A. Wilson, II
  • Patent number: 4275241
    Abstract: A process for the preparation of a-phenoxy-benzaldehyde which comprises contacting the 3-phenoxy-benzyl alcohol of the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and represent hydrogen or halogen with an aqueous solution of a dichromate in the presence of aqueous sulphuric acid at a temperature in the range of 50.degree. to 125.degree. C. The 3-phenoxy-benzaldehyde can be in a mixture of other organic compounds such as obtained by hydrolyzing a 3-phenoxy toluene chlorinated in the side chain at a temperature of 140.degree.-210.degree. C. under pressure.
    Type: Grant
    Filed: October 29, 1979
    Date of Patent: June 23, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Siegfried Bohm, Alfons Klein, Karlfried Wedemeyer