Patents Examined by L. Hendriksen
  • Oxidation of primary amines to oximes by elemental oxygen with catalyst regeneration
    Patent number: 4560797
    Abstract: Improved processes for the conversion to oximes by selective oxidation, in the vapor phase, of saturated primary aliphatic or alicyclic amines having 2 to 12 carbon atoms especially cyclohexylamine to cyclohexanone oxime with elemental oxygen, in a reaction zone, in the presence of an effective amount of a catalyst comprising an oxygen-containing tungsten compound and alumina by (1) periodically regenerating the oxygen-containing tungsten catalyst by heating same at about 250.degree. C.-300.degree. C. in the presence of elemental oxygen, or (2) maintaining the temperature of the oxygen-containing tungsten catalyst in a range of about 100.degree. C.-145.degree. C. or (3) employing higher mol fractions of oxygen and of amine in a range of about 0.2-0.4 in the vapor phase are disclosed. An improved method of preparing an oxygen-containing tungsten on an alumina catalyst is also disclosed.
    Type: Grant
    Filed: December 20, 1982
    Date of Patent: December 24, 1985
    Assignee: Allied Corporation
    Inventors: Jean Yamanis, Emery J. Carlson, John N. Armor
  • Process for synthesizing .alpha.,.beta.-ethylenically unsaturated products using a multicomponent acidic catalyst composition
    Patent number: 4560790
    Abstract: A process for preparing a catalyst composition wherein a Metal Hydrocarboxide I, such as aluminum secbutoxide, a Metal Hydrocarboxide II, such as silicon ethoxide, an acidic phosphorus-oxygen composition, such as phosphoric acid, and water, are reacted in the presence of a liquid organic medium, such as acetone, to form a catalyst precursor composition, which is then calcined to form the catalyst, is disclosed. The catalyst is useful for condensing carboxylic acids or their ester with aldehydes or acetals to synthesize .alpha., .beta.-ethylenically unsaturated acids or esters, such as methylmethacrylate.
    Type: Grant
    Filed: August 8, 1983
    Date of Patent: December 24, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventor: Ji-yong Ryu
  • Fluoroacrylic compounds
    Patent number: 4558152
    Abstract: A copolymer of an acrylic acid derivative and an other copolymerizable monomer, the acrylic acid derivative being a compound represented by the formula (1) ##STR1## wherein Rf and Rf' are respectively perfluoroalkyl group having 3 to 21 carbon atoms, a is an integer of 2 to 10, b is an integer of 1 to 10. The said copolymers are useful as water repellent, oil repellent and stain proofing agents.
    Type: Grant
    Filed: April 24, 1985
    Date of Patent: December 10, 1985
    Assignee: Daikin Kogyo Company Limited
    Inventor: Shouji Iwatsuki
  • Production of dichloroformoxime
    Patent number: 4558160
    Abstract: A method for the production of dichloroformoxime is disclosed in which chloropicrin is dissolved in a nonbasic aprotic organic solvent together with anhydrous hydrogen chloride, and said chloropicrin is reduced to dichloroformoxime in said solution in the presence of powdered tin acting as both a reactant and catalyst. The reaction is preferably carried out in tetrahydrofuran using at least 15 grams of dissolved hydrogen chloride per 100 grams of solvent and chloropicrin in an amount of at least 50% of the weight of the hydrogen chloride. The powdered tin is used in an amount of at least about 1 mole of tin per mole of chloropicrin, and the reaction temperature is preferably about 0.degree. C.
    Type: Grant
    Filed: April 25, 1984
    Date of Patent: December 10, 1985
    Inventor: William R. Hydro
  • Diacrylate and method for manufacturing the same
    Patent number: 4556729
    Abstract: A novel diacrylate or dimethacrylate characterized in that diols having two allyloxy groups in a molecule are esterified with acrylic acid, methacrylic acid or their derivatives, and represented by the following structural formula: ##STR1## wherein R denotes acryloyl or methacryloyl group, and a method for manufacturing the same.
    Type: Grant
    Filed: July 9, 1984
    Date of Patent: December 3, 1985
    Assignee: Sanyo-Kokusaku Pulp Co., Ltd.
    Inventors: Motonobu Kubo, Kazumi Honda
  • Herbicidal cyclohexane-1,3-dione derivatives
    Patent number: 4555263
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: R.sup.1 is selected from alkyl, alkenyl, alkynyl, cycloalkyl benzyl and substituted benzyl;A is selected from hydrogen, halogen, nitro, alkyl, alkoxy, alkylthio, alkenylthio, alkynylthio, cycloalkoxy, cycloalkylthio, sulfamoyl, N-(C.sub.1 to C.sub.6 alkyl)sulfamoyl, N,N-di(C.sub.1 to C.sub.6 alkyl)sulfamoyl, benzylthio and substituted benzylthio;R.sup.2 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, acyl, alkylsulfonyl, benzenesulfonyl, substituted benzenesulfonyl, and an inorganic or organic cation;R.sup.3 is selected from alkyl, alkenyl, alkynyl, substituted alkyl, haloalkenyl and haloalkynyl; andR.sup.4 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl and phenyl.
    Type: Grant
    Filed: December 6, 1982
    Date of Patent: November 26, 1985
    Assignee: ICI Australia Limited
    Inventors: Alexander Serban, Keith G. Watson, Graham J. Bird, Graeme J. Farquharson, Timothy L. Houston
  • Fluorinated ether acyl fluorides having alkylthio or alkylsulfone groups
    Patent number: 4555369
    Abstract: A novel fluorinated cation exchange membrane containing carboxylic acid groups and sulfonic acid groups, both in the form of a specific pendant structure, the carboxylic acid groups being at least 20% on one surface of the membrane and gradually decreasing toward the innerside of the membrane, which membrane is useful in electrolysis of an aqueous alkali metal halide solution with advantageously stable performance for a long term under more severe operational conditions than those conventionally used. The membrane can be prepared from a novel copolymer of a fluorinated olefin with a novel sulfur containing fluorinated vinylether of the formula: ##STR1## wherein k is 0 or 1, l is an integer of 3 to 5, Z is --S-- or --SO.sub.2 -- and R is C.sub.1 -C.sub.10 alkyl, an aryl, Cl or C.sub.1 -C.sub.10 perfluoroalkyl. Acyl fluorides, which are the precursors of the fluorinated olefin ethers, are also disclosed.
    Type: Grant
    Filed: August 29, 1983
    Date of Patent: November 26, 1985
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Kyoji Kimoto, Hirotsugu Miyauchi, Jukichi Ohmura, Mikio Ebisawa, Toshioki Hane
  • Process for the production of ethylene glycol and/or glycollic acid esters, and catalyst therefor
    Patent number: 4551565
    Abstract: In a process for producing ethylene glycol and/or a glycollic acid ester by the vapor phase catalytic hydrogenation of an oxalic acid diester in the presence of a catalyst and hydrogen gas, the improvement wherein the catalyst has the following composition formulaCuMo.sub.k Ba.sub.p O.sub.qwherein k, p and q represent gram-atoms of Mo, Ba and O, respectively, per gram-atom of Cu, k is a number of from 0 to 3, p is a number of from 0 to 6, and q is a number determined depending upon the atomic valence and gram-atoms of Cu, Mo and Ba, provided that k and p are not zero at the same time; and the aforesaid catalyst.
    Type: Grant
    Filed: July 5, 1983
    Date of Patent: November 5, 1985
    Assignee: UBE Industries, Ltd.
    Inventors: Haruhiko Miyazaki, Koichi Hirai, Taizo Uda, Yasuo Nakamura, Harumi Ikezawa, Takanori Tsuchie
  • Manufacture of pent-3-enoic acid and its alkyl esters
    Patent number: 4550195
    Abstract: A process for the manufacture of pent-3-enoic acid and its alkyl esters, of the general formulaCH.sub.3 --CH.dbd.CH--CH.sub.2 --CO--ORwhere R is hydrogen or alkyl of 1 to 4 carbon atoms, comprising carbonylating butadiene with carbon monoxide and a compound ROH at from 300 to 1,000 bars CO pressure and from 100.degree. to 160.degree. C. in the presence of cobalt catalysts and nitrogen bases, wherein C.sub.4 cuts are used as starting materials and a tertiary amine having a pK.sub.A of from 3 to 11 is used as the nitrogen base. The pent-3-enoic acid or alkyl esters produced may be used for the manufacture of adipic acid or its alkyl esters, which compounds are starting materials for the manufacture of nylons.
    Type: Grant
    Filed: August 21, 1981
    Date of Patent: October 29, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Platz, Rudolf Kummer, Heinz-Walter Schneider, Kurt Schwirten
  • Preparation of new fluoropivalic acid fluorides
    Patent number: 4549994
    Abstract: A process for the preparation of a compound according to claim 1, comprising reacting a compound of the formula ##STR1## in which R.sup.3, R.sup.4 and R.sup.5 each independently is CH.sub.3 or CH.sub.2 Cl, at least one of the radicals R.sup.3, R.sup.4 and R.sup.5 being CH.sub.2 Cl,with a metal fluoride at elevated temperature. The products are new and useful as intermediates for making other compounds, especially carbamate insecticide synergists.
    Type: Grant
    Filed: July 13, 1984
    Date of Patent: October 29, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hermann Hagemann, Erich Klauke, Ernst Kysela
  • Purification of crude, liquid organosulfonyl chloride
    Patent number: 4549993
    Abstract: Crude, liquid organosulfonyl chloride is purified by first scrubbing the crude liquid with an aqueous hydrochloric acid solution, separating the scrubbing solution and then subjecting the scrubbed organosulfonyl chloride to vacuum stripping while sweeping the material being stripped with an inert gas.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: October 29, 1985
    Assignee: Pennwalt Corporation
    Inventor: Paul J. McElligott, Jr.
  • Preparation of 2-isopropenyl-or 2-isopropylidenyl-3-hexenoates from chrysanthemic acid esters
    Patent number: 4547586
    Abstract: A novel substituted diene alcohol represented by a general formula: ##STR1## wherein X represents a group of the formula ##STR2## and a process for the preparation thereof a lower alkoxycarbonyl group of a substituted diene carboxylic acid ester having an E configuration obtained by the treatment of a chrysanthemic acid ester with Bronsted acid or a substituted diene carboxylic acid ester having a Z configuration obtained by the thermal cleavage of a chrysanthemic acid ester is reduced to methylol derivative.
    Type: Grant
    Filed: December 5, 1983
    Date of Patent: October 15, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Gohfu Suzukamo, Mitsuhisa Tamura, Masami Fukao
  • Process for the preparation of compact nitroguanidine
    Patent number: 4544769
    Abstract: A method of preparing compact nitroguanidine of high bulk density by crystallization from an initially hot nitroguanidine solution. The solution is cooled, while being agitated, at a temperature gradient of at least 3.degree. C./minute, with the crystallization taking place, only at temperatures less than 50.degree. C., from a supersaturated solution. The solvent for the nitroguanidine solution is selected from the group consisting of polyhydric, lower aliphatic alcohols, the mono- or dialkyl ethers of these polyhydric, lower aliphatic alcohols, dimethylformamide, dimethyl sulfoxide, or mixtures thereof. The formed nitroguanidine, in addition to having a high bulk density, has a compact form which makes it possible to prepare a slurry from nitroguanidine and to be able to process nitroguanidine as a composition amenable to casting.
    Type: Grant
    Filed: September 8, 1980
    Date of Patent: October 1, 1985
    Assignee: Fraunhofer-Gesellschaft zur Forderung der angewandten Forschung e.V.
    Inventors: Walter Engel, Herbert Heinisch
  • Process for producing acetic anhydride
    Patent number: 4544511
    Abstract: A process for producing acetic anhydride which comprises reacting methyl acetate or dimethyl ether with carbon monoxide in the presence of a catalyst comprising (a) nickel or a nickel compound, (b) at least one halide selected from the group consisting of bromides, iodides and mixtures thereof and (c) at least one organic nitrogen group compound and together with a specific co-catalyst is disclosed. According to this invention acetic anhydride is produced by using highly active non-expensive catalyst and co-catalyst.
    Type: Grant
    Filed: February 22, 1985
    Date of Patent: October 1, 1985
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tomiya Isshiki, Yasuhiko Kijima, Yuh Miyauchi, Takao Kondo
  • Process for making carboxylic acid halides
    Patent number: 4543217
    Abstract: The disclosure relates to a process for making carboxylic acid halides by reacting an alkyl halide having 1 to 6 carbon atoms or aryl halide with carbon monoxide, optionally in admixture with up to 30 volume % hydrogen, under practically anhydrous conditions at temperatures of 350 to 575 K under pressures of 1 to 300 bars in the presence of a catalyst system containing at least one noble metal belonging to group VIII of the Periodic System of the elements or its compounds, iodine and/or its compounds and optionally an inert organic solvent. To this end, the disclosure provides for use to be made of a catalyst system which additionally contains a compound of the elements belonging to groups I to III of the Periodic System, and acetic acid.
    Type: Grant
    Filed: December 15, 1983
    Date of Patent: September 24, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinz Erpenbach, Klaus Gehrmann, Winfried Lork, Peter Prinz
  • Synthesis of vinyl esters
    Patent number: 4543422
    Abstract: A vinyl ester of the formula R.sup.3 COOR.sup.4 where R.sup.3 is CH.sub.2 .dbd.CH-- or CH.sub.2 .dbd.C.CH.sub.3 -- and R.sup.4 contains at least four carbon atoms and is selected from alkyl, cycloalkyl and aminoalkyl is conducted by reaction of an ester R.sup.3 COOR.sup.1, where R.sup.1 is C.sub.1-3 alkyl, with metal alcoholate formed from an alcohol R.sup.4 OH and titanium, aluminum, zirconium, calcium or magnesium in the absence of water or reactive alcohol.
    Type: Grant
    Filed: October 20, 1983
    Date of Patent: September 24, 1985
    Assignee: Allied Colloids Limited
    Inventor: David Farrar
  • Process for the production of guanidine hydrochloride
    Patent number: 4542240
    Abstract: Guanidine hydrochloride is produced from cyanogen chloride in a new manner. The cyanogen chloride is reacted with ammonia in the absence of a solvent at a temperature of about 140.degree. to 220.degree. C. It is advantageous to add an ammonium salt at the beginning of the reaction and to use ammonia in at least stoichiometrical amounts.
    Type: Grant
    Filed: February 24, 1981
    Date of Patent: September 17, 1985
    Assignee: Degussa Aktiengesellschaft
    Inventors: Peter Schalke, Langer Manfred, Klaus Huthmacher
  • Di-perfluoroalkyl carbamyl group containing acrylates and methacrylates
    Patent number: 4540805
    Abstract: Di-perfluoroalkyl containing acrylate and methacrylate monomer derivatives of the formula: ##STR1## where R.sub.f is perfluoroalkyl, omega-hydroperfluoroalkyl, or perfluoroalkoxy substituted perfluoroalkyl;R.sub.1 is alkylene of up to 12 carbon atoms:X is --S-- or --SO.sub.2 --;Alk is alkanetriyl having from 1 to 12 carbon atoms;.phi. is phenylene which is unsubstituted or substituted by chlorine, bromine, alkyl of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms;n is 0 or 1;R.sub.2 is alkylene of up to 12 carbon atoms; andR.sub.3 is hydrogen or methyl; their preparation and use as hydrophobic and oleophobic finishes are disclosed.
    Type: Grant
    Filed: October 1, 1984
    Date of Patent: September 10, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Robert A. Falk
  • (Meth) acrylate esters of dipentaerythritol caprolactone condensates
    Patent number: 4540809
    Abstract: Disclosed herein are ethylenically unsaturated compounds represented by the formula: ##STR1## wherein R represents a hydrogen atom or a methyl group, on the average m and n respectively represent a value of 1 to 5, on the average p represents a value of 1 to 6, on the average q and r represent respectively a value of 0 to 3, on the average s represents a value of 0 to 5, p+q+r+s is 6: q+r is a value of 0 to 3, p+s is a value of 3 to 6 and the average value of mp+nq is 1 to 30, and a method for producing the same.
    Type: Grant
    Filed: June 24, 1983
    Date of Patent: September 10, 1985
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Minoru Yokoshima, Kazuyoshi Nawata, Tetsuo Ohkubo, Hideaki Hattori
  • Perfluoro vinyl ethers
    Patent number: 4536352
    Abstract: A novel fluorinated copolymer is prepared by copolymerization of a fluorinated olefin with a novel sulfur containing fluorinated vinylether of the formula: ##STR1## wherein k is 0 or 1 and l is an integer of 3 to 5, which is prepared from starting materials which are also novel. Said copolymer is useful for preparation of a fluorinated cation exchange membrane having carboxylic acid groups and/or sulfonic acid groups which can be used advantageously in electrolysis of an aqueous alkali metal halide solution with improved electrolysis performance.
    Type: Grant
    Filed: December 14, 1981
    Date of Patent: August 20, 1985
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Kyoji Kimoto, Hirotsugu Miyauchi, Jukichi Ohmura, Mikio Ebisawa, Toshioki Hane