Patents Examined by Jane S. Myers
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Patent number: 4259519Abstract: Conjugated diolefins (e.g., 1,3-butadiene) are carbonylated by the palladium-catalyzed addition of carbon monoxide and an alcohol of the formula ROH (e.g., benzyl alcohol) whereby polycarboxylic esters are formed in which the pair of double bonds of the conjugated diolefin has been transformed into a moiety having the formula: ##STR1## In the process, the olefin, carbon monoxide, and alcohol are reacted in the presence of a palladium(II) salt, a copper(II) salt, and a base, at certain concentrations and at a pressure and temperature sufficient to effect the carbonylation. The resulting unsaturated diester can be hydrolyzed and hydrogenated or vice versa to obtain the corresponding linear diacid (e.g., adipic acid).Type: GrantFiled: July 19, 1978Date of Patent: March 31, 1981Assignee: Polymer Sciences CorporationInventor: John K. Stille
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Patent number: 4258207Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.Type: GrantFiled: March 15, 1979Date of Patent: March 24, 1981Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4256911Abstract: A process for producing optically active 16-substituted prostaglandins and new 16-substituted prostaglandins produced thereby which are useful as cardiovascular agents and as agents for inducing labor in pregnant females and for the termination of pregnancy.Type: GrantFiled: June 9, 1980Date of Patent: March 17, 1981Assignee: Hoffmann-La Roche Inc.Inventors: George W. Holland, Jane L. Jernow, Perry Rosen
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Patent number: 4254280Abstract: 2-(2-Hydroxy-3-oxobutyl)-3,3-dimethylcyclopropanecarbaldehyde and certain derivatives thereof, such as 1-[2-(2,2-dihalovinyl)-3,3-dimethylcyclopropyl]-3-oxo-2-butyl acetate, are useful intermediates for the preparation of dihalovinyl-type pyrethroid esters.Type: GrantFiled: November 23, 1979Date of Patent: March 3, 1981Assignee: Shell Oil CompanyInventor: Johannes Syrier
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Patent number: 4252727Abstract: A resin for coatings, particularly useful as a medium for printing inks and paints, comprising a modified polymer produced by adding at least one .alpha.,.beta.-unsaturated dicarboxylic acid or anhydride thereof to at least one liquid conjugated diolefinic polymer having a number average molecular weight of 150 to 3,000, a viscosity of 2 to 5,000 cps at 30.degree. C. and at least 50% of cis-1,4 structure and subjecting the resulting adduct to diesterification with at least one alcohol having 1 to 27 carbon atoms and whereby the acid value owing to the carboxyl group or the carboxylic anhydride group of the resulting modified polymer being made not more than 10.Type: GrantFiled: February 5, 1976Date of Patent: February 24, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Seimei Yasui, Minoru Hino, Kunio Izumi, Otsugu Hayashi
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Patent number: 4251543Abstract: 2-(p-prenylphenyl)propionic acid and pharmaceutically acceptable salts thereof are disclosed. They exhibit anti-inflammatory and analgesic activity with low gastrointestinal action.Type: GrantFiled: June 4, 1979Date of Patent: February 17, 1981Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Takehiro Amano, Jiro Sawada, Michitada Sasajima
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Patent number: 4251667Abstract: A process for the preparation of aromatic urethanes by reacting an aromatic amine, an alcohol and carbon monoxide in the presence of a catalytic quantity of a copper salt, oxygen and a dehydrating agent is disclosed. The reaction is preferably carried out using a copper halide catalyst and dehydrating agents which combine with water to release the alcohol used in the preparation of the urethane product.Type: GrantFiled: June 6, 1979Date of Patent: February 17, 1981Assignee: Atlantic Richfield CompanyInventor: Haven S. Kesling, Jr.
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Patent number: 4239803Abstract: A composition for enhancing and maintaining mechanical properties such as tensile strength of an ethylene polymer on heating at elevated temperature comprises (A) an initiator of cross-linking having a half-life measured at 110.degree. C. of 0.1 to 50 hours and (B) an alkylthioalkylenecarboxylic acid ester of a polycarbocyclic polyhydric phenol.Type: GrantFiled: June 14, 1977Date of Patent: December 16, 1980Assignee: Argus Chemical CorporationInventors: Toshio Ohzeki, Mitsuo Akutsu, Yutaka Nakahara, Tohru Haruna, Motonobu Minagawa, Masahiro Nonoyama
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Patent number: 4237310Abstract: The oxidation of methyl benzenes, such as toluene, with air or oxygen in the presence of acetic anhydride and sulfuric acid catalyst to form a phenolic acetate and methylene diacetate may be carried out under mild conditions when small amounts of benzaldehyde are added to the reaction.The resulting acetates may then be pyrolyzed to yield phenolic compounds and formaldehyde, respectively.Type: GrantFiled: November 3, 1978Date of Patent: December 2, 1980Assignee: Suntech, Inc.Inventors: George Suld, James E. Lyons, Robert W. Shinn
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Patent number: 4237309Abstract: The oxidation of methyl benzenes with air or oxygen in the presence of acetic anhydride, benzaldehyde and an acid catalyst under mild reaction conditions yields a phenolic acetate and formaldehyde or paraformaldehyde when the ratio of acetic anhydride to methyl benzene is adjusted to provide the selective formation of the phenolic acetate and formaldehyde or paraformaldehyde. In this process, it is essential that the flow of air or oxygen through the reaction medium be maintained at a sufficient rate to provide for the continuous removal of formaldehyde as it is formed. The formaldehyde may then be recovered in the form of paraformaldehyde.Type: GrantFiled: November 3, 1978Date of Patent: December 2, 1980Assignee: Suntech, Inc.Inventors: James E. Lyons, George Suld, Robert W. Shinn
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Patent number: 4234740Abstract: A process for preparing a diester of a dicarboxylic acid having two more carbon atoms than the unsaturated hydrocarbon used as the starting material, which comprises subjecting an unsaturated hydrocarbon, carbon monoxide and an alcohol to reaction in the presence of a platinum group metal or a salt thereof; a compound selected from the group consisting of nitric acid, a nitrogen oxide and an ester of nitrous acid; and a halogen compound.Type: GrantFiled: November 28, 1978Date of Patent: November 18, 1980Assignee: Ube Industries, Ltd.Inventors: Sumio Umemura, Kanenobu Matsui, Yoshinari Ikeda, Katsuro Masunaga, Takumi Kadota
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Patent number: 4234733Abstract: A process for producing an aliphatic carboxylic acid and an aliphatic carboxylic acid esters ofa phenol which comprises reacting a phenol of the general formula ##STR1## wherein n is an integer of 1 to 6, m is an integer of 0 to 5, the sum of n and m is 6, and R represents hydrogen, alkyl, aryl, alkenyl, carbinol, acyl, acyloxy, formyl, carboxy, halogen, sulfo, nitro, nitroso, amino, amido, or cyano, and two or more R groups may be the same or different, and the substituents R may be bonded to each other to form a penta- or hexa-carboxylic or heterocyclic ring, and an aliphatic carboxylic acid ester or an aliphatic ether with carbon monoxide, and separating and recovering the aliphatic carboxylic acid from the reaction mixture.Type: GrantFiled: October 24, 1978Date of Patent: November 18, 1980Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomiya Isshiki, Yasuhiko Kijima, Yuh Miyauchi
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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: 4232042Abstract: The invention relates to novel compounds of general formula I: ##STR1## and salts, esters and amides thereof, in which R.sub.1 and R.sub.2 represent hydrogen, alkyl or alkenyl (1-4 C),R.sub.3 represents hydrogen, halogen, hydroxy, alkyl (1-4 C) or alkoxy (1-4 C),n has the value 0, 1 or 2 andALK is a saturated or unsaturated hydrocarbon radical with 3-12 carbon atoms, in which a straight carbon chain in between the benzene rings is present, containing 3-8 carbon atoms, andthe dotted line indicates an optional extra bond between the first and second carbon counted from the phenyl ring, in case of an extra bond the group R.sub.2 and one hydrogen attached to said second carbon being absent, having valuable hypocholesterolaemic and hypotriglyceriolaemic properties.Type: GrantFiled: October 4, 1976Date of Patent: November 4, 1980Assignee: Akzona IncorporatedInventors: Alexander C. Campbell, Colin L. Hewett, Filippus J. Zeelen
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Patent number: 4230881Abstract: A method for the preparation of organic esters of oxalic acid by reaction of carbon monoxide under pressure with the corresponding alcohol is disclosed, the improvement consisting in the use of a quite particular catalyst system. The catalyst is a binary system in which the principal member is a palladium complex and the co-catalyst is a compound, preferably an organic compound having an acidic nature, no matter how weak.Type: GrantFiled: April 6, 1978Date of Patent: October 28, 1980Assignee: Snamprogetti, S.p.A.Inventors: Ugo Romano, Franco Rivetti
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Patent number: 4230885Abstract: Mixture of salts of aromatic mono- or polycarboxylic acids are converted to terephthalate salts in presence of selected catalyst or catalyst mixture, e.g., a mixture of potassium, sodium and cesium benzoates, is disproportionated in the presence of zinc and/or a zinc salt or a mixture of zinc and/or cadmium and a zinc and/or cadmium salt. The mixture of compounds which are to be converted to terephthalate salts will contain at least those of two different alkali metals. A formula m+n is equal to at least 4 is given for determining the catalyst, or catalysts, to be employed. In one embodiment, now preferred, a mixture of sodium, potassium, and cesium benzoates is heated at a reaction temperature of the order of 350.degree.-430.degree. C., more preferably 380.degree.-415.degree. C., in presence of a catalytic mixture of zinc and cadmium benzoates to obtain high yields and rates of reaction at temperatures substantially below those needed in the prior art for similar or better yields, etc.Type: GrantFiled: June 12, 1978Date of Patent: October 28, 1980Assignee: Phillips Petroleum CompanyInventor: Yulin Wu
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Patent number: 4229591Abstract: A process for preparing a diester of oxalic acid which comprises bringing carbon monoxide into contact with an ester of nitrous acid or with an alcohol and a nitrogen oxide or a hydrate of the nitrogen oxide in the gaseous phase in the presence of a solid catalyst containing metallic palladium or a salt thereof, a gas containing molecular oxygen being introduced into the reaction system in cases where said nitrogen oxide or a hydrate of the nitrogen oxide requires molecular oxygen together with the alcohol to form an ester of nitrous acid.Type: GrantFiled: August 31, 1978Date of Patent: October 21, 1980Assignee: UBE Industries, Ltd.Inventors: Kenji Nishimura, Kozo Fujii, Keigo Nishihira, Masaoki Matsuda, Shinichiro Uchiumi
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Patent number: 4229589Abstract: A process for preparing a diester of oxalic acid which comprises bringing carbon monoxide into contact with an ester of nitrous acid in the liquid phase, in the presence of metallic palladium or a salt thereof, preferably with introduction of a gas containing molecular oxygen into the reaction system, more preferably with further incorporation of an alcohol in the reaction system.Type: GrantFiled: August 31, 1978Date of Patent: October 21, 1980Assignee: UBE Industries, Ltd.Inventors: Kenji Nishimura, Shinichiro Uchiumi, Kozo Fujii, Keigo Nishihira, Masayoshi Yamashita, Hiroshi Itatani
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Patent number: 4228181Abstract: 3,3-Dimethylindan-5-yl N-alkyl-carbamic acid esters of the formula ##STR1## in which R.sup.1 is alkyl,R.sup.2 is hydrogen or alkyl, andR.sup.3 and R.sup.4 each independently is chlorine or alkyl, which possess fungicidal and arthropod development-inhibiting properties.Type: GrantFiled: August 8, 1978Date of Patent: October 14, 1980Assignee: Bayer AktiengesellschaftInventors: Detlef Grotkopp, Karlfried Wedemeyer, Wilhelm Brandes, Hans Scheinpflug, Peter Roessler
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Patent number: 4227010Abstract: Disclosed is a process for recovering dimethyl terephthalate and intermediate products from the tarry fraction of the residue generated in the production of dimethyl terephthalate from p-xylene and methanol by the cooxidation procedure. In the process the tarry fraction is established in admixture with a catalytic quantity of alkali metal material, examples of which are sodium and potassium carbonate, at about 200.degree.-350.degree. C., and the resulting reaction mixture is maintained in this temperature range until at least a substantial quantity of dimethyl terephthalate has formed. Generally, dimethyl terephthalate and intermediate products are separated from the reaction mixture. The separation in preferred embodiments is by distillation.Type: GrantFiled: October 13, 1978Date of Patent: October 7, 1980Assignee: HercofinaInventor: Horace E. Hood