Polyoxy Alcohol Moiety Patents (Class 560/112)
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Patent number: 4259531Abstract: Polytetramethylene ether glycols with molecular weights of from 300 to 4500 are produced by polymerizing tetrahydrofuran with an adduct of antimony pentachloride with carboxylic acids or carboxylic acid esters as the catalyst in the presence of a carboxylic acid anhydride, e.g., acetic anhydride, as the promoter. Esterified, e.g., acetylated, polytetramethylene ether glycols produced are subsequently converted to polytetramethylene ether glycols by saponification or transesterification. The process causes substantially less environmental pollution than do prior art methods, yet it is both economical and flexible.Type: GrantFiled: December 15, 1978Date of Patent: March 31, 1981Assignee: BASF AktiengesellschaftInventors: Otto H. Huchler, Walter Mesch, Siegfried Winderl, Herbert Mueller, Herwig Hoffmann
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Patent number: 4249019Abstract: A carboxylic ester is produced in one step in a high yield and with a high selectivity by reacting an aldehyde with an alcohol in the presence of oxygen by using a catalyst comprising (I) palladium, (II) at least one compound selected from the group consisting of lead compounds, thallium compounds and mercury compounds and (III) at least one compound selected from the group consisting of alkali metal compounds and alkaline earth metal compounds.Type: GrantFiled: November 13, 1978Date of Patent: February 3, 1981Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Nobuhiro Tamura, Yohei Fukuoka, Setsuo Yamamatsu, Yoshio Suzuki, Ryoichi Mitsui, Tadayuki Ibuki
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Patent number: 4245114Abstract: In the preparation of glycol esters by the liquid phase reaction of an olefin, molecular oxygen, and a carboxylic acid in the presence of a catalyst system comprising a variable valent cation in association with bromine, chlorine, a bromine-containing compound or a chlorine-containing compound, improved reaction rate and product selectively are achieved by carrying out the reaction in a vertical reaction zone communicating with at least one zone for movement of liquid from the top of the vertical reaction zone to the bottom of said reaction zone, and providing gaseous and liquid feeds in predetermined relationships and providing predetermined vertical superficial liquid velocities.Type: GrantFiled: December 19, 1978Date of Patent: January 13, 1981Assignee: Halcon Research and Development CorporationInventor: Alan Peltzman
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Patent number: 4245074Abstract: A method is provided for the preparation of an acrylate copolymer having a number average molecular weight of 400-2000 by polymerization of a monomer mixture consisting of 35-60 mole % of styrene and/or .alpha.-methyl styrene, 20-60 mole % of acrylic acid and/or methacrylic acid and 0-30 mole % of one or more other monovinyl compounds in the presence of a 2 to 8 carbon atoms-containing mercaptomonocarboxylic acid or mercaptodicarboxylic acid as chain length regulator in an amount of 0.05 to 0.2 moles per mole of the monomeric compounds, after which the resulting reaction product is brought into reaction with a glycidyl ester of a monocarboxylic acid. The invention also relates to a liquid coating composition having a solids content of at least 60% by weight based on the acrylate copolymer thus prepared and a curing agent.Type: GrantFiled: July 21, 1978Date of Patent: January 13, 1981Assignee: Akzo N.V.Inventor: Roelof Buter
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Patent number: 4243799Abstract: A process for the preparation of polybutylene glycol carboxylic acid diesters of the formulaR--CO--O--CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --O).sub.n CO--R.sup.1by polymerizing pretreated tetrahydrofuran in the presence of one or more carboxylic acids and/or carboxylic acid anhydrides and of a polymerization catalyst, especially antimony pentachloride or a bleaching earth containing less than 3% by weight of water, wherein the tetrahydrofuran is treated with a strong mineral acid, an organic sulfonic acid, silica gel and/or a bleaching earth prior to the polymerization.Type: GrantFiled: May 18, 1979Date of Patent: January 6, 1981Assignee: BASF AktiengesellschaftInventors: Herbert Mueller, Otto H. Huchler, Herwig Hoffmann
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Patent number: 4243592Abstract: The present specification discloses novel 9,11-dideoxy- or 9,11,15-trideoxy-10-oxa-thromboxane B compounds, their novel method of preparation and the pharmaceutical compositions and use thereof as antihrombotic, antiinflammatory, and antiasthma agents.Type: GrantFiled: March 12, 1979Date of Patent: January 6, 1981Assignee: The Upjohn CompanyInventor: Douglas R. Morton, Jr.
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Patent number: 4237312Abstract: In the oxidation of acyclic conjugated dienes, recovery and recycle of the oxidation catalyst is accomplished by distilling off the oxidation solvent, extraction of the oxidation product with a suitable solvent, and removal of the extraction solvent residue from the catalyst, and recycle of the catalyst to the oxidation step.Type: GrantFiled: April 2, 1979Date of Patent: December 2, 1980Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4236022Abstract: Mono- and dicarboxylic acid esters of 1,2-dihydroxyalkanes of the formulae ##STR1## wherein A represents a bivalent radical selected from the group consisting of alkylene having from 1 to 16 carbon atoms, hydroxyalkylene having from 1 to 8 carbon atoms and 1 to 4 hydroxys, alkenylene having from 2 to 18 carbon atoms, alkoxyalkylene having from 2 to 6 carbon atoms, phenylene, alkylphenylene having from 1 to 12 carbon atoms in the alkyl; R.sub.1 represents a member selected from the group consisting of hydrogen and alkyl having from 1 to 12 carbon atoms; R.sub.2 is alkyl having from 10 to 22 carbon atoms; and R.sub.Type: GrantFiled: December 21, 1978Date of Patent: November 25, 1980Assignee: Henkel Kommanditgesellschaft auf Aktien (Henkel KGaA)Inventors: Ulrich Zeidler, Fanny Scheuermann
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Patent number: 4233230Abstract: A process for preparing esters and halides is disclosed comprising the step of reacting a cyclic olefin having the formula I ##STR1## wherein R.sub.1 and R.sub.4 are the same or different from each other and each represents hydrogen, methyl, or ethyl;R.sub.2 and R.sub.3 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms; andn represents a whole number from 2 to 12, with an acyclic olefin having the formula II ##STR2## wherein R.sub.5 represents hydrogen, methyl, ethyl or the group ##STR3## wherein R.sub.12 and R.sub.13 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms;Y represents halogen; an acyloxy group R.sub.14 --CO--O wherein R.sub.14 represents alkyl containing 1-12 carbon atoms, phenyl or phenyl alkyl containing 7-12 carbon atoms, or an oxycarbonyl group R.sub.15 --O--CO wherein R.sub.Type: GrantFiled: May 4, 1978Date of Patent: November 11, 1980Assignee: Rhone-Poulenc IndustriesInventor: Jean Otton
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Patent number: 4230484Abstract: A method of controlling pollen formation in a hermaphrodite plant, the method comprising applying to the plant, to seed of the plant or to the locus surrounding the plant or seed, a compound of formula: ##STR1## wherein R.sup.1 is hydrogen or alkyl, R.sup.2 is hydrogen, alkyl, alkyl substituted with up to three halogens (e.g. trichloro- or trifluoro-methyl), cycloalkyl, alkoxyalkyl (e.g. 2-methoxy-ethyl), substituted or unsubstituted aryl or aralkyl or an alkali metal (e.g. sodium or potassium), alkaline earth metal or quaternary ammonium cation, R.sup.3 is halogen, nitro, alkyl, alkyl substituted with up to three halogens (e.g. trichloro- or trifluoro-methyl), cycloalkyl, alkoxy, alkylthio, amino, acylamino (e.g. acetylamino), mono- or di-alkylamino, acyl (e.g. acetyl), haloacyl (e.g. bromoacetyl), cyano, amido, hydroxy, carboxy, alkoxycarbonyl (e.g.Type: GrantFiled: April 25, 1978Date of Patent: October 28, 1980Assignee: Imperial Chemical Industries LimitedInventors: Jeremy J. Batch, Keith P. Parry, Colin F. Rowe, David K. Lawrence, Michael J. Brown
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Patent number: 4229362Abstract: A process for esterifying terminal hydroxyl groups of a polyoxyalkylene compound comprising one or more ring opened tert.-butyl or tert.-amyl glycidyl ether groups, without removing a significant portion of these tert.-alkyl ether groups. The process is conducted by contacting the polyoxyalkylene compound with an organic, carboxylic acid or anhydride in the liquid phase, in the presence of a small but catalytically effective amount of a Lewis base.Type: GrantFiled: April 16, 1979Date of Patent: October 21, 1980Assignee: The Dow Chemical CompanyInventor: Paula R. Norman
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Patent number: 4225726Abstract: This invention relates to an improved method for the catalyzed condensation of aldehydes in the liquid phase to form 1,3-glycol monoesters utilizing tin metal or a tin oxide catalyst. Condensation can be visualized as an aldol condensation followed by a Tischenko reaction between the aldol and a third molecule of aldehyde. In its simplest form the condensation can be illustrated by the following general formula ##STR1## R or R.sup.1 =Hydrogen or alkyl group of 1 to 20 carbon atoms or aromatic groups. R and R.sup.1 can also be part of a cyclic system.Type: GrantFiled: May 23, 1979Date of Patent: September 30, 1980Assignee: Eastman Kodak CompanyInventors: Don L. Morris, Anthony W. McCollum
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Patent number: 4225727Abstract: The invention relates to a process for the production of an unsaturated glycol diester by the reaction of a conjugated diene compound, a carboxylic acid and molecular oxygen in the presence of a solid catalyst. For example, 1,4-diacetoxy-2-butene is prepared at high conversion and high selectivity by reacting butadiene, molecular oxygen and acetic acid in the presence of a solid catalyst containing palladium, tellurium and at least one element selected from the group consisting of tin, germanium and lead. The product is an intermediate for the preparation of 1,4-butanediol.Type: GrantFiled: October 5, 1979Date of Patent: September 30, 1980Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Setsuo Kamiyama, Kouji Shiozawa, Yoshiharu Okumura, Katsumi Kaneko
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Patent number: 4223160Abstract: Niobium and ruthenium salts are employed as catalyst in the reaction of oxirane compounds with carboxylic acids. The acrylate esters produced can be used in photocurable compositions.Type: GrantFiled: March 26, 1979Date of Patent: September 16, 1980Assignee: Union Carbide CorporationInventor: Lawrence G. Hess
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Patent number: 4221917Abstract: Monoolefins and diolefins are converted to corresponding esters in a process by contacting together at least one monoolefin, diolefin or mixture thereof, oxygen, at least one iodosoaryl dicarboxylate and at least one carboxylic acid, carboxylic acid anhydride or mixture thereof.Type: GrantFiled: March 3, 1978Date of Patent: September 9, 1980Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4221916Abstract: Saturated vicinal esters produced by reacting olefins with carboxylic acid and anhydrides thereof in the presence of oxygen and a vanadium- or ruthenium-containing catalyst.Type: GrantFiled: August 25, 1978Date of Patent: September 9, 1980Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4220800Abstract: Saturated vicinal esters are produced by reacting olefins with carboxylic acids and oxygen in the presence of a boron-containing catalyst component.Type: GrantFiled: September 5, 1978Date of Patent: September 2, 1980Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4201726Abstract: A synthesis of Vitamin E has the condensation of 2,4-pentanediene and 1,2-epoxy-2,6,10,14-tetramethylpentadecane including intermediates in this synthesis which uses base catalyzed condensations of aliphatic compounds to construct the Vitamin E molecule from aliphatic precursors.Type: GrantFiled: September 11, 1978Date of Patent: May 6, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Gary L. Olson, Gabriel Saucy
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Patent number: 4189566Abstract: A process for the preparation of polybutylene glycol carboxylic acid diesters of the formulaR-CO-O--CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -O).sub.n CO-R.sup.1by polymerizing pretreated tetrahydrofuran in the presence of one or more carboxylic acids and/or carboxylic acid anhydrides and of a polymerization catalyst, especially antimony pentachloride or a bleaching earth containing less than 3% by weight of water, wherein the tetrahydrofuran is treated with a strong mineral acid, an organic sulfonic acid, silica gel and/or a bleaching earth prior to the polymerization.Type: GrantFiled: December 29, 1978Date of Patent: February 19, 1980Assignee: BASF AktiengesellschaftInventors: Herbert Mueller, Otto H. Huchler, Herwig Hoffmann
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Patent number: 4182901Abstract: Diacyloxyolefins are isomerized by contacting one or more diacyloxyolefins with a catalyst system comprising selenium dioxide and a suitable carboxylic acid. There can be additionally present in the catalyst system at least one compound selected from the group consisting of a carboxylic acid anhydride, a polar compound, and an ionic reagent.Type: GrantFiled: October 13, 1977Date of Patent: January 8, 1980Assignee: Phillips Petroleum CompanyInventors: George B. Fozzard, John R. Norell
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Patent number: 4180676Abstract: A catalyst comprising a uranium compound, an alkali metal ion, and a halide, is effective to convert conjugated dienes in carboxylic acid media to diacyloxy olefins.Type: GrantFiled: August 25, 1977Date of Patent: December 25, 1979Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4172098Abstract: Halobenzenes are manufactured by (a) a one-vessel reaction of anilines with halogenating agents to give haloanilines, followed by reaction of the mixture thus obtained with alkanols and nitrosylating agents in the presence of water and acid at not less than 35.degree. C. or (b) the corresponding reaction of a haloaniline which has been manufactured in the above manner or by some other method and has been isolated from its reaction mixture. The products are starting materials for the manufacture of drugs, dyes and pesticides.Type: GrantFiled: November 15, 1977Date of Patent: October 23, 1979Assignee: BASF AktiengesellschaftInventors: Horst Scheuermann, Ulrich Jersak, Helmut Gorth
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Patent number: 4164615Abstract: A catalyst comprising a titanium compound, an alkali metal ion, and a halide, is effective for the conversion of conjugated diolefins to diacyloxy olefins.Type: GrantFiled: August 25, 1977Date of Patent: August 14, 1979Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4163115Abstract: Esters of poly(tetramethylene ether) glycol are prepared by polymerizing tetrahydrofuran in a reaction mixture which contains, in addition to the tetrahydrofuran, and acylium ion precursor such as acetic anhydride, a polymeric catalyst which contains sulfonic acid groups and, optionally, a carboxylic acid such as acetic acid.Type: GrantFiled: January 13, 1978Date of Patent: July 31, 1979Assignee: E. I. Du Pont de Nemours and CompanyInventors: George E. Heinsohn, Ivan M. Robinson, Gerfried Pruckmayr, Walter W. Gilbert
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Patent number: 4162363Abstract: Conjugated dienes or monoolefins are converted to diesters in a process utilizing a catalyst system comprising an alkali metal compound and a sulfur source comprising elemental sulfur or a sulfur halide, optionally with a halide source, in carboxylic acid media.Type: GrantFiled: August 25, 1977Date of Patent: July 24, 1979Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4144396Abstract: Alkylene glycol esters are produced by the reaction of an olefin, a carboxylic acid and molecular oxygen employing a bromine-containing substance and a nitrogen oxide as a catalyst.Type: GrantFiled: June 27, 1977Date of Patent: March 13, 1979Assignee: Mitsubishi Chemical Industries LimitedInventors: Takeshi Okano, Naoto Wada, Yoshimitsu Kobayashi
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Patent number: 4131743Abstract: Unsaturated diesters are produced by a process which comprises reacting, in a flowing gaseous phase, a gaseous mixture comprising a conjugated diene, a carboxylic acid and molecular oxygen in the presence of (A) a catalyst comprising palladium, vanadium, antimony and at least one alkali metal carboxylate, or in the presence of (B) a catalyst comprising palladium, vandium, antimony, at least one alkali metal carboxylate and at least one alkali metal halide. The catalyst (A) maintains a high activity and a high selectivity for a long time. The catalyst (B), in which further the alkali metal halide is added, shows a higher activity and a higher selectivity for a longer time. And its activity and selectivity are stable and durable at high temperatures such as 160.degree. - 200.degree. C. Furthermore, the addition of the alkali metal halide suppresses combustion reaction of dienes such as butadiene remarkably.Type: GrantFiled: July 6, 1976Date of Patent: December 26, 1978Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Yoshinori Yoshida, Tutomu Kobayashi, Hironobu Shinohara, Izumi Hanari
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Patent number: 4124619Abstract: Preparation of carboxylic acid esters of .gamma.-hydroxy-tiglic-aldehyde from bismonocarboxylic acid esters of but-2-en-1,4-diol via 1,4-diacetoxy-2-formyl butane including intermediates in this synthesis.Type: GrantFiled: March 23, 1977Date of Patent: November 7, 1978Assignee: Hoffmann-La Roche Inc.Inventors: Peter Fitton, Harold Moffet
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Patent number: 4123552Abstract: Fungus and mold growth in crops and organic matter are inhibited by the use of bis-carboxylic acid esters and compositions thereof. In a preferred embodiment, crops and animal feedstuffs are preserved during storage by applying a microbiocidal amount of a mono-, di or trioxymethylene, or lower alkylidene bis-alkanoate, or a mixture thereof.Type: GrantFiled: October 17, 1975Date of Patent: October 31, 1978Assignee: Chevron Research CompanyInventors: Daniel L. Kensler, Jr., Gustave K. Kohn, David D. Walgenbach
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Patent number: 4121039Abstract: Unsaturated glycol diesters are prepared at high reaction rates, high degrees of conversion and high selectivity, by reacting a conjugated diene, a carboxylic acid and oxygen, in the presence of an improved active solid catalyst, in the liquid phase. The improved catalyst of the invention comprises palladium containing thorium as a promotor. In the preferred embodiment, butadiene and acetic acid are reacted with oxygen to produce the desired 1,4-diacetoxy-2-butene at high conversions and selectivity.Type: GrantFiled: September 26, 1977Date of Patent: October 17, 1978Assignee: GAF CorporationInventors: R. Parthasarathy, Eugene Victor Hort
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Patent number: 4113971Abstract: Diacyloxy olefins are prepared by the reaction of a conjugated diolefin with a carboxylic acid in the presence of free oxygen and a Group VIB metal oxide.Type: GrantFiled: February 21, 1975Date of Patent: September 12, 1978Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4112241Abstract: Alkylene glycol esters are produced by the reaction of an olefin, a carboxylic acid and molecular oxygen employing an iodine-containing substance and a nitrogen oxide as a catalyst.Type: GrantFiled: March 30, 1977Date of Patent: September 5, 1978Assignee: Mitsubishi Chemical Industries LimitedInventors: Takeshi Okano, Naoto Wada, Yoshimitsu Kobayashi
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Patent number: 4112240Abstract: Process for production of dipropyleneglycol dibenzoate isomer mixture of the formulas: ##STR1## A crude methyl benzoate containing at least 80 wt.% methylbenzoate, which is a by-product of production of dimethylterephthalate by catalytic oxidation of p-xylene and/or methyl-p-toluate and esterification of the resulting acids with methanol, is contacted with dipropylene glycol commercial isomer mixture in the presence of a catalyst for a transesterification to produce said benzoate. The catalyst is an aluminum alkoxide or an aluminum silicon alkoxide containing the group Al O Si. The product is obtained in good yield, has good color, and is useful as a plasticizer for PVC.Type: GrantFiled: August 9, 1976Date of Patent: September 5, 1978Assignee: Dynamit Nobel AktiengesellschaftInventors: Hans Leo Hulsmann, Gustav Renckhoff
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Patent number: 4104043Abstract: A new series of substituted esters of 3-hydroxyindone compounds have been found to have exceptional miticidal and herbicidal activity.Type: GrantFiled: December 12, 1972Date of Patent: August 1, 1978Assignee: Union Carbide CorporationInventors: John A. Durden, Jr., Anthony A. Sousa, John F. Stephen
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Patent number: 4099018Abstract: A conjugated diolefin is reacted with at least one compound selected from the group consisting of a carboxylic acid and a carboxylic acid anhydride in the presence of oxygen and a catalyst comprising a lead compound.Type: GrantFiled: April 12, 1976Date of Patent: July 4, 1978Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4095037Abstract: A conjugated diolefin is reacted with a carboxylic acid, a carboxylic acid anhydride, or a mixture thereof, in the presence of oxygen and a catalyst comprising a compound of bismuth, an alkali metal compound and a source of nitrate ion.Type: GrantFiled: September 8, 1976Date of Patent: June 13, 1978Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4093815Abstract: A conjugated diolefin is reacted with at least one compound selected from the group consisting of a carboxylic acid and a carboxylic acid anhydride in the presence of oxygen and a catalyst comprising a rare earth metal compound, an alkali metal compound and a halide compound.Type: GrantFiled: August 12, 1976Date of Patent: June 6, 1978Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4091006Abstract: A new series of substituted esters of 3-hydroxyindone compounds have been found to have exceptional miticidal and herbicidal activity.Type: GrantFiled: October 1, 1975Date of Patent: May 23, 1978Assignee: Union Carbide CorporationInventors: John A. Durden, Jr., Anthony A. Sousa, John F. Stephen
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Patent number: 4088677Abstract: Carboxyphenyl-alkylphosphinic acids and the esters thereof corresponding to the formula I ##STR1## where R.sub.1 is alkyl having from 1 to 4 carbon atoms, R.sub.2 and R.sub.3, independently, each are hydrogen, alkyl having from 1 to 12 carbon atoms, or oxyalkyl HO-(CH.sub.2).sub.n --CHR--, n being 1 to 3 and R hydrogen or alkyl having from 1 to 4 carbon atoms, and a process for the preparation of these compounds.Type: GrantFiled: January 7, 1977Date of Patent: May 9, 1978Assignee: Hoechst AktiengesellschaftInventor: Hans-Jerg Kleiner
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Patent number: 4084062Abstract: This invention relates to the utility of compounds having the general formula ##STR1## WHEREIN R is selected from the group consisting of --H, --CH.sub.3, ##STR2## Said compounds are useful as plant growth regulators.Type: GrantFiled: December 14, 1976Date of Patent: April 11, 1978Assignee: Stauffer Chemical CompanyInventor: Alexander Mihailovski
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Patent number: 4075412Abstract: Diacyloxy olefins are prepared by the reaction of a conjugated diolefin with a carboxylic acid in the presence of free oxygen and a catalyst system consisting essentially of an indium compound, a halide source and an alkali metal compound.Type: GrantFiled: April 21, 1976Date of Patent: February 21, 1978Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4074058Abstract: New mixed esters of diols having one hydroxyl group esterified with benzoic acid and the other esterified with various saturated or unsaturated aliphatic acids or aromatic acids other than benzoic are found to have antimicrobial activity against several pathogenic microorganisms, and to have properties making them useful as antimicrobial agents.Type: GrantFiled: February 15, 1977Date of Patent: February 14, 1978Assignee: The United States of America as represented by the Secretary of AgricultureInventors: August V. Bailey, Gordon J. Boudreaux, Gene Sumrell, Arthur F. Novak
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Patent number: 4073876Abstract: In the preparation of glycol esters by the oxidation of an olefin in the presence of a catalyst comprising tellurium, wherein the accumulation of foreign metals in association with the tellurium catalyst component has an adverse effect upon the reaction, such foreign metals are maintained at low levels while the tellurium catalyst values are recovered for recycling in high yield by purging a portion of a high-boiling residual fraction produced in the distillation treatment of the reaction mixture and treating the purged portion with water and/or an aqueous alkaline solution.Type: GrantFiled: July 1, 1976Date of Patent: February 14, 1978Assignee: Halcon International, Inc.Inventor: Vijai P. Gupta
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Patent number: 4069242Abstract: A synergistic catalytic effect is realized in the esterification reaction between an organic carboxylic acid and a vicinal epoxide by using a catalyst system comprising: (a) a compound containing an amino and/or ammonium nitrogen atom, in combination with (b) a soluble compound containing an ionizable atom of iron or chromium.Type: GrantFiled: September 9, 1971Date of Patent: January 17, 1978Assignee: The Dow Chemical CompanyInventor: Arthur E. Gurgiolo
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Patent number: 4069385Abstract: In the preparation of olefin derivatives having an ester group at the allylic position (hereinafter referred to as "allylic ester(s)") which comprises reacting an olefin having at least one hydrogen atom at the allylic position and which will produce an allylic ester having an asymmetric carbon atom with an organic peroxide in the presence of a copper catalyst, a method for producing optically active allylic esters characterized by using, as the copper catalyst, an optically active copper complex derived from an optically active compound selected from the group consisting of Schiff's bases of the formula: ##STR1## and amino acids of the formula: ##STR2## wherein R.sub.0 is an optically active alkyl, cycloalkyl, aralkyl or aryl group which may contain an unsaturated bond and/or a substituent having a hetero atom, X and Y are each a hydrogen atom, an alkyl, cycloalkyl, aralkyl or aryl group, or a substituent having a hetero atom, R.sub.1 and R.sub.Type: GrantFiled: June 3, 1976Date of Patent: January 17, 1978Assignee: Sumitomo Chemical Company, LimitedInventors: Masashi Araki, Tsuneyuki Nagase
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Patent number: 4068082Abstract: Esters are prepared by reaction of acyl halides and alcohols or hydroxyalkyl esters and acid halides in the presence of a tertiary amine and polar aprotonic solvents. Bis(2-methacrylatoethyl) phthalate is prepared by the reaction of phthaloyl chloride with 2-hydroxyethyl methacrylate in pyridine and acetone. Bis-phenol-A-bis(2-methacrylatoethyl)ether is prepared from 2,2-bis[4-(2-hydroxyethoxy)phenyl]-propane and methacryl chloride in acetone.Type: GrantFiled: September 19, 1973Date of Patent: January 10, 1978Assignee: Lee PharmaceuticalsInventors: Donald G. Stoffey, Jan Alexander Orlowski
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Patent number: 4061868Abstract: There is provided an improvement in the process for the preparation of organic monoesters of vicinal glycols and the corresponding free glycols by reacting an olefin with oxygen, water and a carboxylic acid, in the liquid phase, at an initial pH of lower than 7, the improvement comprising contacting the reaction mixture with a catalyst system consisting essentially of (i) iodine or an iodine compound selected from the group consisting essentially of copper iodide, manganese iodide, cerium iodide, an alkali metal iodide, an alkali earth metal iodide and the iodohydride of the olefin, (ii) a copper compound selected from the group consisting essentially of copper oxide, copper hydroxide, copper carbonate, copper iodide, and a copper salt of the carboxylic acid, and (iii) an activating ion selected from the group consisting of manganese cation, cerium cation, an alkali metal cation, an alkaline earth metal cation, nitric anion or a mixture of any of the foregoing, wherein the molar ratio of the carboxylic acid tType: GrantFiled: September 25, 1975Date of Patent: December 6, 1977Assignee: Montedison S.p.A.Inventors: Carlo Fumagalli, Giuseppe Caprara, Paolo Roffia
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Patent number: 4059641Abstract: Polyprenyl derivatives having the formula ##STR1## in which R.sup.1 and R.sup.2 may be the same or different and each represents hydrogen atom, hydroxyl group, an alkoxy group having 1-8 carbon atoms, an aliphatic acyloxy group having 2-18 carbon atoms, an aromatic acyloxy group or an araliphatic acyloxy group having 2-3 carbon atoms in the aliphatic acyl moiety, R.sup.3 represents hydrogen atom, an alkyl group having 1-8 carbon atoms, an aliphatic acyl group having 2-18 carbon atoms, an aromatic acyl group or an araliphatic acyl group having 2-3 carbon atoms in the aliphatic acyl moiety, n is an integer of 1-4 and, when n is an integer of 2-4, R.sup.2 's may be the same or different; provided that, when n is 1 or 2, at least one of R.sup.1 and R.sup.2 's is hydroxyl group, an alkoxy group, an aliphatic acyloxy group, an aromatic acyloxy group or an araliphatic acyloxy group. These derivatives are useful as medicines for treating peptic ulcer.Type: GrantFiled: November 18, 1975Date of Patent: November 22, 1977Assignee: Sankyo Company LimitedInventors: Hiroshi Mishima, Akira Ogiso, Shinsaku Kobayashi
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Patent number: 4052442Abstract: A process for preparing glycol esters such as ethylene glycol diacetate which comprises contacting a monoolefin such as ethylene with an organic monocarboxylic acid such as acetic acid containing a palladous salt and either a nitrate or a nitrite.Type: GrantFiled: January 12, 1967Date of Patent: October 4, 1977Assignee: Kuraray Co., Ltd.Inventors: Masuhiko Tamura, Teruo Yasui
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Patent number: T964007Abstract: new mixed esters of diols having one hydroxyl group esterified with benzoic acid and the other esterified with various saturated or unsaturated aliphatic acids or aromatic acids other than benzoic are found to have antimicrobial activity against several pathogenic microorganisms, and to have properties making them useful as antimicrobial agents.Type: GrantFiled: February 15, 1977Date of Patent: November 1, 1977Inventors: August V. Bailey, Gordon J. Boudreaux, Gene Sumrell, Arthur F. Novak