Unsaturated Patents (Class 562/598)
  • Patent number: 5777142
    Abstract: 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: Grant
    Filed: August 22, 1995
    Date of Patent: July 7, 1998
    Assignee: The Lubrizol Corporation
    Inventors: Paul E. Adams, Mark R. Baker, Jeffry G. Dietz
  • Patent number: 5763651
    Abstract: 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: Grant
    Filed: May 29, 1997
    Date of Patent: June 9, 1998
    Assignee: Roche Vitamins Inc.
    Inventor: August Ruttimann
  • Patent number: 5750815
    Abstract: 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: Grant
    Filed: August 29, 1996
    Date of Patent: May 12, 1998
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, SonBinh T. Nguyen
  • Patent number: 5750571
    Abstract: 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: Grant
    Filed: December 23, 1996
    Date of Patent: May 12, 1998
    Assignee: Genzyme Corporation
    Inventors: Seng Hing Cheng, Shaona Lee Fang, Henry Hoppe, IV, Alan Edward Smith
  • Patent number: 5750572
    Abstract: 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: Grant
    Filed: July 5, 1996
    Date of Patent: May 12, 1998
    Assignee: Prospa B.V.
    Inventor: Tiberio Bruzzese
  • Patent number: 5734075
    Abstract: 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: Grant
    Filed: December 12, 1995
    Date of Patent: March 31, 1998
    Assignee: Elf Atochem S.A.
    Inventors: Michel Fauconet, Norbert Richard, Patrick Delafin
  • Patent number: 5728872
    Abstract: 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: Grant
    Filed: June 27, 1994
    Date of Patent: March 17, 1998
    Inventor: Lutz Riemenschneider
  • Patent number: 5714517
    Abstract: 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: Grant
    Filed: August 22, 1996
    Date of Patent: February 3, 1998
    Assignee: Monsanto Company
    Inventor: Peter Gerrard Ruminski
  • Patent number: 5698722
    Abstract: 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: Grant
    Filed: June 6, 1995
    Date of Patent: December 16, 1997
    Assignee: 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
  • Patent number: 5674898
    Abstract: 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: Grant
    Filed: June 7, 1993
    Date of Patent: October 7, 1997
    Assignee: Genzyme Corporation
    Inventors: Seng Hing Cheng, Shaona Lee Fang, Henry Hoppe, IV, Alan Edward Smith
  • Patent number: 5672746
    Abstract: 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: Grant
    Filed: August 30, 1994
    Date of Patent: September 30, 1997
    Assignees: American Biogenetic Sciences, Inc., University College Dublin
    Inventors: Heinz Nau, Ciaran M. Regan
  • Patent number: 5644010
    Abstract: 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: Grant
    Filed: July 18, 1995
    Date of Patent: July 1, 1997
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Toru Kurihashi, Miki Kawashima, Takeo Yamaguchi
  • Patent number: 5629434
    Abstract: 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: Grant
    Filed: September 25, 1995
    Date of Patent: May 13, 1997
    Assignee: Exxon Chemical Patents Inc
    Inventors: 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
  • Patent number: 5625096
    Abstract: 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: Grant
    Filed: October 19, 1994
    Date of Patent: April 29, 1997
    Assignee: Rhone-Poulenc Chimie
    Inventors: Phillipe Denis, Carl Patois, Robert Perron
  • Patent number: 5599960
    Abstract: 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: Grant
    Filed: May 25, 1995
    Date of Patent: February 4, 1997
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, William J. Fylak, Marie R. Hanna, Futoshi Fujioka
  • Patent number: 5583237
    Abstract: 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: Grant
    Filed: February 26, 1996
    Date of Patent: December 10, 1996
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, William J. Fylak, Marie R. Hanna, Futoshi Fujioka
  • Patent number: 5536873
    Abstract: 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: Grant
    Filed: December 9, 1994
    Date of Patent: July 16, 1996
    Assignees: E. I. du Pont de Nemours and Company, DSM N.V.
    Inventors: Bruce Murphree, Ronnie Ozer
  • Patent number: 5532421
    Abstract: 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: Grant
    Filed: July 19, 1994
    Date of Patent: July 2, 1996
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takanobu Terauchi, Toyohisa Sakurada, Takehiko Fukumoto, Hiroshi Suzuki
  • Patent number: 5527951
    Abstract: 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: Grant
    Filed: January 12, 1995
    Date of Patent: June 18, 1996
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Jamil A. Khan, Walter Nudenberg, David J. Smudin, Demetreos N. Matthews
  • Patent number: 5504243
    Abstract: 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: Grant
    Filed: May 19, 1995
    Date of Patent: April 2, 1996
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Kazuhiko Sakamoto, Takahiro Takeda, Masatoshi Ueoka, Yoji Akazawa, Masao Baba
  • Patent number: 5449821
    Abstract: 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: Grant
    Filed: June 30, 1994
    Date of Patent: September 12, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Peter Neumann, Hans Martan, Hermann Petersen, Walter Doerflinger
  • Patent number: 5420347
    Abstract: 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: Grant
    Filed: December 1, 1993
    Date of Patent: May 30, 1995
    Assignee: Pfizer Inc.
    Inventor: Charles W. Murtiashaw
  • Patent number: 5410078
    Abstract: 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: Grant
    Filed: January 3, 1994
    Date of Patent: April 25, 1995
    Assignee: The Sherwin-Williams Company
    Inventor: Rodney M. Harris
  • Patent number: 5389680
    Abstract: 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: Grant
    Filed: October 18, 1993
    Date of Patent: February 14, 1995
    Assignee: Monsanto Company
    Inventor: Peter G. Ruminski
  • Patent number: 5380938
    Abstract: 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: Grant
    Filed: February 24, 1994
    Date of Patent: January 10, 1995
    Assignee: Rhone-Poulenc Chimie
    Inventors: Philippe Denis, Francois Metz, Carl Patois, Robert Perron
  • Patent number: 5380884
    Abstract: 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: Grant
    Filed: April 11, 1994
    Date of Patent: January 10, 1995
    Assignee: Osaka Organic Chemical Ind. Co., Ltd.
    Inventors: Hideo Hosokawa, Misao Shikatsu, Takahiro Fujimoto
  • Patent number: 5354886
    Abstract: 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: Grant
    Filed: July 26, 1993
    Date of Patent: October 11, 1994
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Dae C. Park, Sung Y. Cho
  • Patent number: 5298655
    Abstract: 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: Grant
    Filed: September 27, 1991
    Date of Patent: March 29, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Neville J. Anthony, Ta-Jyh Lee, Robert L. Smith, Gerald E. Stokker
  • Patent number: 5292920
    Abstract: Disclosed are salts of N-nitrosophenylhydroxylamine and their use as polymerization inhibitors.
    Type: Grant
    Filed: August 24, 1993
    Date of Patent: March 8, 1994
    Assignee: Rohm and Haas Company
    Inventors: Rita K. Upmacis, William Bauer, Jr., Samuel F. Reed, Jr.
  • Patent number: 5288903
    Abstract: 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: Grant
    Filed: July 26, 1993
    Date of Patent: February 22, 1994
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Emilio E. Bunel, Chen-Chou Chiang, Michael B. D'Amore, Erik J. Schaumann, Leon S. Scott
  • Patent number: 5260465
    Abstract: 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: Grant
    Filed: December 16, 1991
    Date of Patent: November 9, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Sheo B. Singh, Deborah L. Zink
  • Patent number: 5252473
    Abstract: 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: Grant
    Filed: September 23, 1991
    Date of Patent: October 12, 1993
    Assignee: Battelle Memorial Institute
    Inventors: Paul C. Walkup, Charles A. Rohrmann, Richard T. Hallen, David E. Eakin
  • Patent number: 5245079
    Abstract: 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: Grant
    Filed: March 17, 1992
    Date of Patent: September 14, 1993
    Assignee: Pfizer Inc.
    Inventor: Charles W. Murtiashaw
  • Patent number: 5221768
    Abstract: 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: Grant
    Filed: May 7, 1990
    Date of Patent: June 22, 1993
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Masaaki Kato, Tetsuya Uno, Masao Kobayashi, Naoto Osuga
  • Patent number: 5210298
    Abstract: 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: Grant
    Filed: October 27, 1989
    Date of Patent: May 11, 1993
    Assignee: Nippon Shokubai Kagaku Kogyo, Co., Ltd.
    Inventors: Tadao Shimomura, Yoshio Irie, Hitoshi Takahashi, Katsuhiro Kajikawa, Jyunichi Saga, Teruaki Fujiwara, Takumi Hatsuda
  • Patent number: 5189202
    Abstract: 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: Grant
    Filed: July 29, 1988
    Date of Patent: February 23, 1993
    Assignee: Lucky, Ltd.
    Inventors: Yong Z. Kim, Won S. Kim
  • Patent number: 5171888
    Abstract: 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: Grant
    Filed: April 23, 1991
    Date of Patent: December 15, 1992
    Assignee: Betz Laboratories, Inc.
    Inventor: Paul V. Roling
  • Patent number: 5145989
    Abstract: 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: Grant
    Filed: July 14, 1987
    Date of Patent: September 8, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Edward F. Dougherty, Paul James L.
  • Patent number: 5126482
    Abstract: 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: Grant
    Filed: January 3, 1991
    Date of Patent: June 30, 1992
    Assignee: Nippon Mining Co., Ltd.
    Inventors: Takeshi Nakai, Osamu Takahashi
  • Patent number: 5118837
    Abstract: 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: Grant
    Filed: February 12, 1987
    Date of Patent: June 2, 1992
    Assignee: Givaudan Corporation
    Inventors: Alan J. Chalk, Laszlo V. Wertheimer
  • Patent number: 5089611
    Abstract: 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: Grant
    Filed: March 12, 1990
    Date of Patent: February 18, 1992
    Assignee: Petrolite Corporation
    Inventor: Jacob Mathew
  • Patent number: 5081292
    Abstract: .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: Grant
    Filed: April 30, 1990
    Date of Patent: January 14, 1992
    Assignee: Rhone-Poulenc Chimie
    Inventors: Philippe Denis, Jean Jenck, Robert Perron
  • Patent number: 5075494
    Abstract: 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: Grant
    Filed: April 25, 1990
    Date of Patent: December 24, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventor: Karl-Rudolf Gassen
  • Patent number: 5043468
    Abstract: 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: Grant
    Filed: November 24, 1989
    Date of Patent: August 27, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventors: Robert Maurer, Michel Landry
  • Patent number: 5041646
    Abstract: 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: Grant
    Filed: August 22, 1986
    Date of Patent: August 20, 1991
    Assignee: Consortium fur elektrochemische Industrie GmbH
    Inventor: Helmut Gebauer
  • Patent number: 5034156
    Abstract: 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: Grant
    Filed: January 8, 1990
    Date of Patent: July 23, 1991
    Assignee: Mallinckrodt Specialty Chemicals Company
    Inventor: John W. Varwig
  • Patent number: 5023372
    Abstract: 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: Grant
    Filed: May 16, 1989
    Date of Patent: June 11, 1991
    Assignee: Betz Laboratories, Inc.
    Inventor: Paul V. Roling
  • Patent number: 5011975
    Abstract: 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: Grant
    Filed: July 17, 1989
    Date of Patent: April 30, 1991
    Assignee: Nippon Miktron Limited
    Inventors: Tokiyuki Hiramitsu, Ken-ichi Sakamoto
  • Patent number: 5001257
    Abstract: 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: Grant
    Filed: May 11, 1987
    Date of Patent: March 19, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Patrick M. Burke, Francis J. Waller
  • Patent number: 4966996
    Abstract: 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: Grant
    Filed: June 2, 1988
    Date of Patent: October 30, 1990
    Assignee: Desitin Arznemittel GmbH
    Inventor: Helmut Schafer