Unsaturated Patents (Class 562/598)
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Patent number: 5777142Abstract: Compositions comprising unsaturated hydroxycarboxylic compounds, a process for reacting olefinic compounds with carboxylic reagents and products prepared by the process. The compositions containing the hydroxycarboxylic compounds and the products of the process are useful as intermediates for preparing additives for lubricants and fuels.Type: GrantFiled: August 22, 1995Date of Patent: July 7, 1998Assignee: The Lubrizol CorporationInventors: Paul E. Adams, Mark R. Baker, Jeffry G. Dietz
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Patent number: 5763651Abstract: A process for the manufacture of polyene esters or polyene acids comprises reacting a polyene O,O-dialkylacetal of di(O,O-dialkylacetal) with a vinylketene acetal or analogue thereof in the presence of a Lewis acid, hydrolyzing the reaction mixture depending on the vinylketene acetal used, subsequently cleaving alcohol under strongly basic conditions from the polyene derivative produced at this stage and, where the desired ester or carboxy group is still not present, performing the respective conversion. Certain intermediates in this process form a further aspect of the invention. The final products are primarily carotenoids which can be used appropriately, e.g. as colorants and pigments for foodstuffs, animal products etc.Type: GrantFiled: May 29, 1997Date of Patent: June 9, 1998Assignee: Roche Vitamins Inc.Inventor: August Ruttimann
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Patent number: 5750815Abstract: Disclosed are ruthenium and osmium carbene compounds which are stable in the presence of a variety of functional groups and which can be used to catalyze olefin metathesis reactions on unstrained cyclic and acyclic olefins. Specifically, the present invention relates to carbene compounds of the formula ##STR1## wherein: M is Os or Ru; R and R.sup.1 are independently selected from hydrogen and functional groups C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.2 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl or C.sub.1 -C.sub.20 alkylsulfinyl; each optionally substituted with C.sub.1 -C.sub.5 alkyl, a halogen, C.sub.1 -C.sub.5 alkoxy or with a phenyl group optionally substituted with a halogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy; X and X.sup.Type: GrantFiled: August 29, 1996Date of Patent: May 12, 1998Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, SonBinh T. Nguyen
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Patent number: 5750571Abstract: Methods for treating cystic fibrosis are described. The methods involve the administration of a protein enhancing agent, differentiating agent and/or carboxy-compound to a subject afflicted with cystic fibrosis such that mutant cystic fibrosis transmembrane regulator protein present within cystic fibrosis-associated cells becomes functional. Other aspects described include therapeutic compositions and packaged drugs.Type: GrantFiled: December 23, 1996Date of Patent: May 12, 1998Assignee: Genzyme CorporationInventors: Seng Hing Cheng, Shaona Lee Fang, Henry Hoppe, IV, Alan Edward Smith
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Patent number: 5750572Abstract: 4,7,10,13,16,19-cis-Docosahexaenoic acid (DHA) salts with basic amino acids, in particular arginine and lysine, have favorable therapeutic and technological characteristics compared with the acid.Type: GrantFiled: July 5, 1996Date of Patent: May 12, 1998Assignee: Prospa B.V.Inventor: Tiberio Bruzzese
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Patent number: 5734075Abstract: To recover these noble products consisting of acrylic acid monomer, acrylic ester monomers and alcohols, a thermal cracking is performed in the absence of catalyst on a mixture of heavy distillation residues originating, on the one hand, from the manufacture of acrylic acid and, on the other hand, from the manufacture of the esters, the light fraction originating from the dissociation reactions is continuously vaporized during the cracking operation and this light fraction is distilled in order to recover, after condensation, the required products.Type: GrantFiled: December 12, 1995Date of Patent: March 31, 1998Assignee: Elf Atochem S.A.Inventors: Michel Fauconet, Norbert Richard, Patrick Delafin
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Patent number: 5728872Abstract: A stabilized acrylic acid composition is provided in which the polymerization of the acrylic acid is inhibited during the distillation process for purifying or separating the acrylic acid as well as during transport and storage. The compositions of the present invention comprise three components: (A) acrylic acid, (B) a stable nitroxyl radical, e.g., the nitroxyl radical 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinyloxy (CAS registry number 2226-96-2) (HTEMPO), and (C) a dihetero-substituted benzene compound having at least one transferable hydrogen, e.g., a quinone derivative such as the mono-methyl-ether of hydroquinone (MEHQ). During the distillation process, transport and storage, components (B) and (C) are present in a polymerization-inhibiting amount. During the distillation process, oxygen (D) is preferably added with components (B) and (C).Type: GrantFiled: June 27, 1994Date of Patent: March 17, 1998Inventor: Lutz Riemenschneider
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Patent number: 5714517Abstract: Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acarids that prey on agricultural crops. Polar compounds, for example, 3,4,4-trifluoro-3-butene-1-amine or 3,4,4-trifluoro-3-butenoic acid, are particularly useful for systemic control of pests. Novel method and intermediates for the preparation of 3,4,4-trifluoro-3-butene-1-amine are also provided.Type: GrantFiled: August 22, 1996Date of Patent: February 3, 1998Assignee: Monsanto CompanyInventor: Peter Gerrard Ruminski
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Patent number: 5698722Abstract: A Koch functionalized product which is the reaction product of at least one polymer having a number average molecular weight of at least 500 and at least ethylenic double bond per polymer chain, with carbon monoxide and a nucleophilic trapping agent. The invention includes functionalized polymer, derivatives thereof and methods of making the same.Type: GrantFiled: June 6, 1995Date of Patent: December 16, 1997Assignee: Exxon Chemical Patents Inc.Inventors: Joseph Victor Cusumano, William Daniel Diana, Jacob Emert, Keith Raymond Gorda, Richard H. Schlosberg, David A. Young, William Bernard Eckstrom, Edris Eileen Manry, Michael John Keenan
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Patent number: 5674898Abstract: Methods and compositions for treating Cystic Fibrosis by mobilizing mutant forms of CFTR, which retain at least some functional activity, to the plasma membrane where they can mediate chloride ion transport are disclosed.Type: GrantFiled: June 7, 1993Date of Patent: October 7, 1997Assignee: Genzyme CorporationInventors: Seng Hing Cheng, Shaona Lee Fang, Henry Hoppe, IV, Alan Edward Smith
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Patent number: 5672746Abstract: Neurotrophic and antiproliferative compounds related to the antiepileptic drug valproate are provided. These compounds are useful for promoting neuronal function as in neurodegenerative disorders and for treating neoplastic disease.Type: GrantFiled: August 30, 1994Date of Patent: September 30, 1997Assignees: American Biogenetic Sciences, Inc., University College DublinInventors: Heinz Nau, Ciaran M. Regan
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Patent number: 5644010Abstract: A curable liquid resin which can give a coating composition capable of forming a film, the curable liquid resin being a copolymer obtained from(A) a monomer of the formula (1) or (2),CH.sub.2 .dbd.C(R.sup.1)COO--R.sup.2 (1)CH.sub.2 .dbd.C(R.sup.3)COO(C.sub.n H.sub.2n O).sub.m--R.sup.4(2)and(B) at least one monomer selected from the group consisting of(B1) a monomer prepared by reacting an ethylenically unsaturated epoxide (a) with a fatty acid (b) of the formula (3)R.sup.5 COOH (3)(B2) a monomer of the formula (4),CH.sub.2 .dbd.C(R.sup.6)CONR.sup.7 R.sup.8 (4)and(B3) a monomer whose molecule has at least two ethylenically unsaturated double bonds.Type: GrantFiled: July 18, 1995Date of Patent: July 1, 1997Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Toru Kurihashi, Miki Kawashima, Takeo Yamaguchi
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Patent number: 5629434Abstract: A Koch functionalized product which is the reaction product of at least one polymer having a number average molecular weight of at least 500 and at least one ethylenic double bond per polymer chain, with carbon monoxide and a nucleophilic trapping agent. The invention includes functionalized polymer, derivatives thereof and methods of making the same.Type: GrantFiled: September 25, 1995Date of Patent: May 13, 1997Assignee: Exxon Chemical Patents IncInventors: Joseph V. Cusumano, William D. Diana, Jacob Emert, Keith R. Gorda, Richard H. Schlosberg, David A. Young, William B. Eckstrom, Edris E. Manry, Michael J. Kennan
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Patent number: 5625096Abstract: Butadiene or derivative thereof is selectively hydroxycarbonylated into at least one pentenoic acid (the pentenoic acids are themselves facilely converted, via hydroxycarbonylation, into adipic acid, a basic starting material for the production of nylon 66 polymers), by reacting same with carbon monoxide and water, at a pressure greater than atmospheric, in the presence of a catalytically effective amount of (1) a palladium catalyst which is soluble in the medium of reaction and (2) crotyl chloride, the amount of the crotyl chloride being at least two mol thereof per mole of palladium values and said palladium values/crotyl chloride at least in part comprising a palladium/crotyl pi-complex, and the amount of water present in the medium of reaction being no greater than about 20% by weight thereof.Type: GrantFiled: October 19, 1994Date of Patent: April 29, 1997Assignee: Rhone-Poulenc ChimieInventors: Phillipe Denis, Carl Patois, Robert Perron
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Patent number: 5599960Abstract: Described are 3,5-dimethyl-pentenyl-dihydro-2(3H)-furanone isomer mixtures defined according to the structure: ##STR1## wherein structure represents mixtures wherein in the mixture in each of the compounds, one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond, processes for preparing same and uses thereof in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, hair preparations, fabric softeners, fabric softener articles, cosmetic powders and perfumed polymers). Also described is a process for preparing such 3,5-dimethyl-pentenyl-dihydro-2(3H)-furanone isomer mixtures using as a starting material 2,7-octadienol having the structure: ##STR2## as well as the process intermediates having the structures: ##STR3## wherein R represents C.sub.1 -C.sub.4 alkyl; R.sub.1 and R.sub.Type: GrantFiled: May 25, 1995Date of Patent: February 4, 1997Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, William J. Fylak, Marie R. Hanna, Futoshi Fujioka
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Patent number: 5583237Abstract: Described are 3,5-dimethyl-pentenyl-dihydro-2(3H)-furanone isomer mixtures defined according to the structure: ##STR1## wherein structure represents mixtures wherein in the mixture in each of the compounds, one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond, processes for preparing same and uses thereof in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, hair preparations, fabric softeners, fabric softener articles, cosmetic powders and perfumed polymers). Also described is a process for preparing such 3,5-dimethyl-pentenyl-dihydro-2(3H)-furanone isomer mixtures using as a starting material 2,7-octadienol having the structure: ##STR2## as well as the process intermediates having the structures: ##STR3## wherein R represents C.sub.1 -C.sub.4 alkyl; R.sub.1 and R.sub.Type: GrantFiled: February 26, 1996Date of Patent: December 10, 1996Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, William J. Fylak, Marie R. Hanna, Futoshi Fujioka
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Patent number: 5536873Abstract: 3-pentenoic acid or the R ester of pentenoic acid is produced by treating pentenoyl chloride in a reactive distillation zone with ROH where R is hydrogen or hydrocarbon of 1 to 6 carbon atoms. Butadiene may be reacted with HCl that is formed by the hydrolysis of pentenoyl chloride, and the butadiene converted to chlorobutene, and the chlorobutene reacted with carbon monoxide to form pentenoyl chloride.Type: GrantFiled: December 9, 1994Date of Patent: July 16, 1996Assignees: E. I. du Pont de Nemours and Company, DSM N.V.Inventors: Bruce Murphree, Ronnie Ozer
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Patent number: 5532421Abstract: An object of the present invention is to provide a method for the preparation of geometrical isomers which are important as constituents of synthetic pheromones, synthetic perfumes, terpenes and the like (i.e., a method for the isomerization of cis-alkenyl compounds to their trans-isomers). In this method, the above-described object is accomplished by reacting a cis-alkenyl compound in the presence of nitric acid used as the sole catalyst.Type: GrantFiled: July 19, 1994Date of Patent: July 2, 1996Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takanobu Terauchi, Toyohisa Sakurada, Takehiko Fukumoto, Hiroshi Suzuki
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Patent number: 5527951Abstract: Tert-alkylmethoxy-substituted vanadium compounds, several of which are novel, are useful as catalysts for the polymerization of ethylene or the copolymerization of ethylene with alphaolefins and (optionally) nonconjugated polyenes. Also disclosed is a novel catalyst composition comprising such vanadium compounds.Type: GrantFiled: January 12, 1995Date of Patent: June 18, 1996Assignee: Uniroyal Chemical Company, Inc.Inventors: Jamil A. Khan, Walter Nudenberg, David J. Smudin, Demetreos N. Matthews
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Patent number: 5504243Abstract: Disclosed herein is a method for inhibiting polymerizable (meth)acrylic acid and esters thereof from polymerizing during their production, transportation and storage by using as the inhibitor N-oxyl compound and more than one compound selected from the group consisting of manganese salt compound, copper salt compound, 2,2,6,6,-tetramethylpiperidine compound and nitroso compound. The N-oxyl compound is one or more kinds selected from 2,2,6,6,-tetramethylpiperidinooxyl, 4-hydroxy-2,2,6,6,-tetramethylpiperidinooxyl and 4,4',4"-tris-(2,2,6,6,-tetramethylpiperidinooxyl)phosphite. The combined use of the inhibitors provides superior inhibiting effect to use alone.Type: GrantFiled: May 19, 1995Date of Patent: April 2, 1996Assignee: Nippon Shokubai Co., Ltd.Inventors: Kazuhiko Sakamoto, Takahiro Takeda, Masatoshi Ueoka, Yoji Akazawa, Masao Baba
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Patent number: 5449821Abstract: A process for the gas phase catalytic oxidation of a C.sub.3-6 alkane, alkanol, alkene or alkenal using as a catalyst multimetal oxide compositions of the formula I, [X.sup.1.sub.a X.sup.2.sub.b O.sub.x ].sub.p [X.sup.3.sub.c X.sup.4.sub.d X.sup.5.sub.e X.sup.6.sub.f X.sup.7.sub.g X.sup.2.sub.h O.sub.y ].sub.q, where X.sup.1 is bismuth, tellurium, antimony, tin and/or copper, X.sup.2 is molybdenum and/or tungsten, X.sup.3 is an alkali metal, thallium and/or samarium, X.sup.4 is an alkaline earth metal, nickel, cobalt, copper, manganose, zinc, tin, cadmium and/or mercury, X.sup.6 is iron, chromium, cerium and/or vanadium, X.sup.6 is phosphorus, arsenic, boron and/or antimony, X.sup.7 is a rare-earth metal, titanium, zirconium, niobium, tantalum, rhenium, ruthenium, rhodium, silver, gold, aluminum, gallium, indium, silicon, geranium, lead, thorium and/or uranium, a is from 0.01 to 8, b is from 0.Type: GrantFiled: June 30, 1994Date of Patent: September 12, 1995Assignee: BASF AktiengesellschaftInventors: Hans-Peter Neumann, Hans Martan, Hermann Petersen, Walter Doerflinger
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Patent number: 5420347Abstract: Immunoregulatory N-(S-3-alkyl-4-heptenoyl)- and N-(S-3-alkylheptanoyl)-D-gamma-glutamyl-glycyl-D-alanine and esters thereof are synthesized via R-trans-2-hexen-4-ols, R-3-alkyl-4-heptenoic acid and S-3-alkylheptanoic acid.Type: GrantFiled: December 1, 1993Date of Patent: May 30, 1995Assignee: Pfizer Inc.Inventor: Charles W. Murtiashaw
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Patent number: 5410078Abstract: An unsaturated acid-functional monomer having the structure: ##STR1## wherein R.sup.1 is hydrogen or methyl and Z is nothing or is a divalent radical of 1 to about 20 carbons.Type: GrantFiled: January 3, 1994Date of Patent: April 25, 1995Assignee: The Sherwin-Williams CompanyInventor: Rodney M. Harris
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Patent number: 5389680Abstract: Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acarids that prey on agricultural crops. Polar compounds, for example, 3,4,4-trifluoro-3-butene-1-amine or 3,4,4-trifluoro-3-butenoic acid, are particularly useful for systemic control of pests. Novel method and intermediates for the preparation of 3,4,4-trifluoro-3-butene-1-amine are also provided.Type: GrantFiled: October 18, 1993Date of Patent: February 14, 1995Assignee: Monsanto CompanyInventor: Peter G. Ruminski
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Patent number: 5380938Abstract: Unsaturated carboxylic acids, e.g., pentenoic acids, are prepared by carbonylating an allylic butenol and/or carboxylate ester thereof with carbon monoxide, in the presence of a catalytically effective amount of an iridium catalyst and an iodinated or brominated promoter therefor, and optionally, a copromoter, notably wherein the promoter/Ir molar ratio ranges from 0.1:1 to 20:1. The final product acids, e.g., 3-pentenoic acid, are themselves readily hydroxycarbonylated, for example, into adipic acid, via reaction with carbon monoxide and water.Type: GrantFiled: February 24, 1994Date of Patent: January 10, 1995Assignee: Rhone-Poulenc ChimieInventors: Philippe Denis, Francois Metz, Carl Patois, Robert Perron
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Patent number: 5380884Abstract: Glycidyl methacrylate is produced by the reaction of an alkali metal salt of methacrylic acid with epichlorohydrin in the presence of a quaternary ammonium salt and a polymerization inhibitor in a reaction system where the water content is adjusted to 500 to 2000 ppm. Glycidyl methacrylate is purified by the method of the present invention, wherein the reaction mixture obtained by the above method is washed with a dilute aqueous solution of sodium hydroxide and heated under a reduced pressure to remove unchanged epichlorohydrin by distillation, after which steam is blown into the reaction system under the conditions of reduced pressure and heating to distill away the remaining epichlorohydrin together with glycidyl methacrylate as the first distillate fraction, followed by ceasing the steam blow and carrying out distillation under the conditions of reduced pressure and heating to obtain glycidyl methacrylate as the main distillate fraction.Type: GrantFiled: April 11, 1994Date of Patent: January 10, 1995Assignee: Osaka Organic Chemical Ind. Co., Ltd.Inventors: Hideo Hosokawa, Misao Shikatsu, Takahiro Fujimoto
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Patent number: 5354886Abstract: The present invention relates to a catalyst, a process for preparing the catalyst and a process for using the catalyst to produce ethylidene diacetate. The conventional preparation methods of ethylidene diacetate suffer from difficulty in separating the catalyst from the product after completion of the reaction. The catalyst of the present invention is simply separated from the product by mere filtration following the completion of reaction. This is a result of using a heterogenized catalyst which is obtained by supporting a homogeneous catalyst in an inorganic carder. The catalyst of the present invention is of the general formula M.sub.a X where M is a compound of a group VIII transition metal, most preferably RhCl.sub.3 .multidot.xH.sub.2 O, and X is an inorganic carrier, preferably selected from the group consisting of kieselguhr, .gamma.-alumina, silica, TiO.sub.2, MgO, ZnO and activated charcoal.Type: GrantFiled: July 26, 1993Date of Patent: October 11, 1994Assignee: Korea Research Institute of Chemical TechnologyInventors: Dae C. Park, Sung Y. Cho
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Patent number: 5298655Abstract: The present invention is directed to farnesyl pyrophosphate analogs which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention, and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.Type: GrantFiled: September 27, 1991Date of Patent: March 29, 1994Assignee: Merck & Co., Inc.Inventors: Neville J. Anthony, Ta-Jyh Lee, Robert L. Smith, Gerald E. Stokker
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Patent number: 5292920Abstract: Disclosed are salts of N-nitrosophenylhydroxylamine and their use as polymerization inhibitors.Type: GrantFiled: August 24, 1993Date of Patent: March 8, 1994Assignee: Rohm and Haas CompanyInventors: Rita K. Upmacis, William Bauer, Jr., Samuel F. Reed, Jr.
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Patent number: 5288903Abstract: Preparation of 3-pentenoic acid by the reaction of 3-pentenoylchloride, water and butadiene. 3-chloro-1-butene and 1-chloro-2-butene are also formed. Preferably the 3-pentenoylchloride is formed by the reaction of chlorobutene with carbon monoxide using a palladium catalyst.Type: GrantFiled: July 26, 1993Date of Patent: February 22, 1994Assignee: E. I. du Pont de Nemours and CompanyInventors: Emilio E. Bunel, Chen-Chou Chiang, Michael B. D'Amore, Erik J. Schaumann, Leon S. Scott
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Patent number: 5260465Abstract: This invention relates to pharmaceutical compounds of structural formula (I): ##STR1## and compositions and methods of treatment utilizing these compounds to inhibit farnesyl protein transferase and farnesylation of the oncogene protein Ras.Type: GrantFiled: December 16, 1991Date of Patent: November 9, 1993Assignee: Merck & Co., Inc.Inventors: Sheo B. Singh, Deborah L. Zink
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Patent number: 5252473Abstract: Processes are disclosed for producing lactic acid, esters of lactic acid, acrylic acid, and esters of acrylic acid, primarily from fermentable carbohydrate materials. An overall process for producing esters of acrylic acid comprises: a) fermenting carbohydrate material with a lactic-acid-forming organism in the presence of NH.sub.3 to produce ammonium lactate; b) combining the ammonium lactate with an alcohol; c) combining the ammonium lactate and alcohol with an effective catalyzing amount of gaseous CO.sub.2 to catalytically esterify the ammonium lactate and alcohol into a lactic acid ester containing solution; d) recovering purified lactic acid ester; and e) vaporizing the lactic acid ester and passing it through a solid catalyst bed comprised of an effective catalyzing amount of crystalline hydrated and partially calcined calcium sulfate to catalytically convert lactic acid ester into an acrylic acid ester. Step "d" would be useful in a process for making low-cost, purified lactic acid.Type: GrantFiled: September 23, 1991Date of Patent: October 12, 1993Assignee: Battelle Memorial InstituteInventors: Paul C. Walkup, Charles A. Rohrmann, Richard T. Hallen, David E. Eakin
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Patent number: 5245079Abstract: Immunoregulatory N-(S-3-alkyl-4-heptenoyl)- and N-(S-3-alkylheptanoyl)-D-gamma-glutamyl-glycyl-D-alanine and esters thereof are synthesized via R-trans-2-hexen-4-ols, R-3-alkyl-4-heptenoic acid and S-3-alkylheptanoic acid.Type: GrantFiled: March 17, 1992Date of Patent: September 14, 1993Assignee: Pfizer Inc.Inventor: Charles W. Murtiashaw
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Patent number: 5221768Abstract: In accordance with the present invention, there is provided a process for the production of deuterated acrylic acid or deuterated methacrylic acid comprising the exchange of hydrogens in acrylic acid or methacrylic acid with deuteriums in the presence of a catalyst. The deuterated acrylic or methacrylic acid is very useful as a starting material in the production of high quality optical plastic fibers.Type: GrantFiled: May 7, 1990Date of Patent: June 22, 1993Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Masaaki Kato, Tetsuya Uno, Masao Kobayashi, Naoto Osuga
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Patent number: 5210298Abstract: A method for the production of an acrylate by the neutralization reaction of acrylic acid and a basic substance, comprising sequentially (A) a step of supplying acrylic acid and said basic substance to water thereby subjecting them to a neutralization reaction while constantly retaining the neutralization ratio of acrylic acid within the neutralization reaction system in the range of 75 to 100 mol %, (B) a step of adjusting the neutralization ratio of acrylic acid within said neutralization reaction system in the range of 100.1 to 110 mol % by supplying said basic substance to said neutralization reaction system, (C) a step of retaining the neutralization ratio of acrylic acid within said neutralization reaction system in the range of 100.Type: GrantFiled: October 27, 1989Date of Patent: May 11, 1993Assignee: Nippon Shokubai Kagaku Kogyo, Co., Ltd.Inventors: Tadao Shimomura, Yoshio Irie, Hitoshi Takahashi, Katsuhiro Kajikawa, Jyunichi Saga, Teruaki Fujiwara, Takumi Hatsuda
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Patent number: 5189202Abstract: In the present invention, 3,3-dimethyl-4-pentenoic acid (DPA) which is used for preparing permethric acid, an intemediate for preparing pyrethroid insecticides, is directly prepared from an isoprenol or a mixture of isoprenol and prenol without having to convert the isoprenol into a prenol or separate the mixture thereof into isoprenol and prenol. The present invention, therefore, has many advantages in view of yield, purity and procedure.Type: GrantFiled: July 29, 1988Date of Patent: February 23, 1993Assignee: Lucky, Ltd.Inventors: Yong Z. Kim, Won S. Kim
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Patent number: 5171888Abstract: Methods and compositions are provided for inhibiting the polymerization of acrylic acid monomers during elevated temperature processing thereof or during storage or shipment of acrylic acid product. The compositions comprise a combination of a Mn source compound and a phenylenediamine compound having at least 1 N--H bond. The methods comprise adding from about 1-10,000 ppm of the combination to the particular acrylic acid containing medium for which such anti-polymerization protection is desired, per million parts of the acrylic acid medium.Type: GrantFiled: April 23, 1991Date of Patent: December 15, 1992Assignee: Betz Laboratories, Inc.Inventor: Paul V. Roling
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Patent number: 5145989Abstract: Black acid or the sulfuric acid residue obtained in the manufacture of ethyl acrylate by reaction of ethylene and acrylic acid in the presence of sulfuric acid is heated and distilled in the presence of a solvent for recovery of acrylic acid and ethyl acrylate.Type: GrantFiled: July 14, 1987Date of Patent: September 8, 1992Assignee: Hoechst Celanese CorporationInventors: Edward F. Dougherty, Paul James L.
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Patent number: 5126482Abstract: Novel fluorine-containing compounds and processes for producing the same are disclosed, the compounds being represented by the general formula (I): ##STR1## wherein R.sup.1 represents an alkyl group or an alkylvinyl group; R.sup.2 represents a fluoroalkyl group; and Y represents a carboxyl group, a chloroformyl group, an alkoxyalkoxycarbonyl group or a hydroxymethyl group.Type: GrantFiled: January 3, 1991Date of Patent: June 30, 1992Assignee: Nippon Mining Co., Ltd.Inventors: Takeshi Nakai, Osamu Takahashi
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Patent number: 5118837Abstract: A modified ruthenium catalyst can be used to selectively hydrogenate an olefinic double bond in the presence of another olefinic double bond in the same or in a different molecule. Modifiers are selected from compounds containing trivalent nitrogen, trivalent phosphorus and divalent sulfur.Type: GrantFiled: February 12, 1987Date of Patent: June 2, 1992Assignee: Givaudan CorporationInventors: Alan J. Chalk, Laszlo V. Wertheimer
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Patent number: 5089611Abstract: An alkyl 2-thiosubstituted-3-substituted-2-butenoate ##STR1## is prepared by reacting an alkyl 2-chloro-3-substituted-3-butenoate with a thio compound under phase transfer conditions.Type: GrantFiled: March 12, 1990Date of Patent: February 18, 1992Assignee: Petrolite CorporationInventor: Jacob Mathew
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Patent number: 5081292Abstract: .beta., .gamma.-Unsaturated carboxylic acids, e.g., 3-hexene-1,6-dioic acid, are selectively prepared by carbonylating (with carbon monoxide) an allyl alcohol, e.g., a butenediol, at an elevated temperature and under superatmospheric pressure, in the presence of a catalytically effective amount of a palladium-based catalyst and at least one quaternary onium chloride of one of the Group VB elements nitrogen or phosphorus, such element being tetracoordinated via carbon atoms and with the proviso that such nitrogen atom may be coordinated to two pentavalent phosphorus atoms.Type: GrantFiled: April 30, 1990Date of Patent: January 14, 1992Assignee: Rhone-Poulenc ChimieInventors: Philippe Denis, Jean Jenck, Robert Perron
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Patent number: 5075494Abstract: Process for the preparation of .alpha.-fluoroacrylic acid derivatives from 2,2-difluoro-1-methyl-cyclopropyl compounds and new 1,1-difluoro-2-halogenoethyl (halogeno)methyl ketones obtainable in this process as intermediates.Type: GrantFiled: April 25, 1990Date of Patent: December 24, 1991Assignee: Bayer AktiengesellschaftInventor: Karl-Rudolf Gassen
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Patent number: 5043468Abstract: The present invention relates to a process and compositions for delaying the gelling of vinyl monomers in an aqueous medium in the presence of a polymerization initiator, by employing a polymerization inhibitor consisting of an N-nitrosophenylamine salt in combination with an aminocarboxylic acid. The composition is used for plugging circulation losses when drilling at great depth.Type: GrantFiled: November 24, 1989Date of Patent: August 27, 1991Assignee: Rhone-Poulenc ChimieInventors: Robert Maurer, Michel Landry
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Patent number: 5041646Abstract: A process for producing cis-2-methyl-2-butenoic acid, which process is preferably based on technical 2-methyl-2-butene nitrile and leads to pure products preferably without costly rectification. The technical nitrile is hydrolyzed by concentrated sulfuric acid at temperatures of up to 130.degree. C. and, following dilution of the sulfuric acid to about 50%, at temperatures of up to 130.degree. C. It is treated by distilling and fractional crystallization.Type: GrantFiled: August 22, 1986Date of Patent: August 20, 1991Assignee: Consortium fur elektrochemische Industrie GmbHInventor: Helmut Gebauer
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Patent number: 5034156Abstract: A new and improved polymerization inhibitor composition, its method of manufacture, and its use in stabilizing the distillation of acrylic acid is made possible by the pre-oxygen-activation of N-nitrosophenylhydroxylamine in combination with hydroquinone mono-methyl-ether (often referred to as p-methoxyphenol) whereupon a synergistic performance of these components is disclosed.Type: GrantFiled: January 8, 1990Date of Patent: July 23, 1991Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: John W. Varwig
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Patent number: 5023372Abstract: Methods and compositions are provided for inhibiting the polymerization of acrylic acid monomers during elevated temperature processing thereof or during storage or shipment of acrylic acid product. The compositions comprise a combination of a Mn source compound and a phenylenediamine compound having at least 1 N-H bond. The methods comprise adding from about 1-10,000 ppm of the combination to the particular acrylic acid containing medium for which such anti-polymerization protection is desired, per million parts of the acrylic acid medium.Type: GrantFiled: May 16, 1989Date of Patent: June 11, 1991Assignee: Betz Laboratories, Inc.Inventor: Paul V. Roling
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Patent number: 5011975Abstract: A (trans 1-propenyl)disulfide derivative having a distinguished anti-tumor effect, represented by the following general formula: ##STR1## , wherein R is a lower alkylene group and R' is a hydrogen atom or a carboxyl protective group, is prepared by allowing a carboxylic acid thiol derivative, represented by the following general formula:AS--R--COOR', wherein R and R' have the same meanings as defined above and A is a thiol protective group releasable by a halogenating agent, to react with a trans 1-propenethiol derivative represented by the following general formula: ##STR2## , wherein A has the same meanings as defined above, in the presence of a halogenating agent.Type: GrantFiled: July 17, 1989Date of Patent: April 30, 1991Assignee: Nippon Miktron LimitedInventors: Tokiyuki Hiramitsu, Ken-ichi Sakamoto
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Patent number: 5001257Abstract: Perfluorinated acid ion-exchange resins are highly effective catalysts for the isomerization of 3-pentenoic compounds to 4-pentenoic compounds, especially if the catalysts contain a group 8 metal in an oxidation state of at least +2.Type: GrantFiled: May 11, 1987Date of Patent: March 19, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventors: Patrick M. Burke, Francis J. Waller
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Patent number: 4966996Abstract: A novel process for the preparation of E-2-propyl-2-pentenoic acid, as well as the physiologically compatible salts thereof is described, in which 2-bromo-2-propyl-pentenoic acid ethyl ester is used as the starting compound. The bromine is split off with a cyclic tertiary amine in acetonitrile as the solvent and preferably the E-isomer of the ethyl ester is formed. The free acid is obtained by subsequent saponification under careful conditions and optionally, preferably using the corresponding carbon dioxide salts in aqueous acetone solution, is converted into the salt form.Type: GrantFiled: June 2, 1988Date of Patent: October 30, 1990Assignee: Desitin Arznemittel GmbHInventor: Helmut Schafer