Preparing From Compound Containing -coo- Group Patents (Class 549/326)
  • Patent number: 6376414
    Abstract: The invention relates to catalysts containing ruthenium and at least one other metal having an atomic number in the range of from 23 to 82 prepared by (a) mixing a suspension of a ruthenium compound having a specific surface area in the range of from 50 to 300 m2/g with a solution of at least one metal compound in which at least one such metal compound contains a metal different from ruthenium and has an atomic number in the range of from 23 to 82, and (b) treating the mixture of the suspension and the solution with a reducing agent.
    Type: Grant
    Filed: July 25, 2000
    Date of Patent: April 23, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Stefan Antons, Lutz Frohn, Jörg-Dietrich Jentsch, Andreas Schulze Tilling, Erich Wolters
  • Publication number: 20020013479
    Abstract: Process for the catalytic preparation of &ggr;-butyrolactone having the general formula 1
    Type: Application
    Filed: June 13, 2001
    Publication date: January 31, 2002
    Inventor: Niels C. Schiodt
  • Patent number: 6288245
    Abstract: A two-stage process for producing tetrahydrofuran and gammabutyrolactone in varying proportions from maleic, succinic anhydride or fumaric acid esters, by vapor phase hydrogenation. The first stage occurs on a copper-based catalyst to produce a mixture of tetrahydrofuran, gammabutyrolactone and butanediol. The second stage occurs on an acidic silica rich silica-alumina type catalyst to convert butanediol to tetrahydrofuran.
    Type: Grant
    Filed: August 6, 1999
    Date of Patent: September 11, 2001
    Assignee: Pantochim S.A.
    Inventor: Aldo Bertola
  • Patent number: 6248906
    Abstract: Process for the production of tetrahydrofuran, gammabutyrolactone and butanediol starting from maleic anhydride esters, consisting of two subsequent hydrogenations.
    Type: Grant
    Filed: August 6, 1999
    Date of Patent: June 19, 2001
    Inventor: Aldo Bertola
  • Patent number: 6239292
    Abstract: A process for the production of at least one C4 compound selected from 1,4-butanediol, gamma-butyrolactone and tetrahydrofuran, in which a solution of maleic anhydride in a high boiling ester is esterified with a C1 to C4 alcohol to form the corresponding maleate ester which is hydrogenated to form the at least one C4 compound. The specified high boiling ester has a boiling point which is about 30 degrees C. higher than that of the di-(C1-C4 alkyl)maleate.
    Type: Grant
    Filed: June 28, 2000
    Date of Patent: May 29, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael William Marshall Tuck, Michael Anthony Wood, Andrew George Hiles
  • Patent number: 6225477
    Abstract: This invention relates to a method of improving the catalytic performance of palladium or ruthenium, rhenium-on-carbon hydrogenation catalysts operating in aqueous media where loss of soluble rhenium may result in rapid catalytic failure. A rhenium-containing hydrogenation catalyst comprised of rhenium on a support material is regenerated by first treating the catalyst with aqueous perrhenic acid or potassium perrhenate followed by treating the catalyst under reducing conditions at elevated temperature and pressure. Treatment of the catalyst as described replenishes dispersed fresh finely divided rhenium which enhances the activity of the catalyst while at the same time allowing the operations to be carried out in situ in the hydrogenation reactor or in a side stream reactor with significant savings in reducing reactor down time and precious metal expenses.
    Type: Grant
    Filed: February 4, 1998
    Date of Patent: May 1, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Richard Edward Ernst, John Byrne Michel, Daniel Campos
  • Patent number: 6127552
    Abstract: A process is disclosed for producing (R)-3-hydroxy-4-butyrolactone from its enantiomer, (S)-3-hydroxy-4-butyrolactone. The (R)-enantiomer can be advantageously utilized in several organic synthesis and industrial processes, such as e.g. GABOB and (R)-carnitine preparation.
    Type: Grant
    Filed: November 30, 1998
    Date of Patent: October 3, 2000
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Fabio Giannessi, Maria Ornella Tinti, Francesco De Angelis
  • Patent number: 6110520
    Abstract: A process for producing high yields of .gamma.-hexalactone and 2-pentanone from the corresponding hexanoic acid starting material is carried out with high amounts of oxygen and sugar in the presence of a mold microorganism. Fragrance compositions and foodstuff compositions are augmented and enhanced by the presence of the product compounds.
    Type: Grant
    Filed: March 25, 1999
    Date of Patent: August 29, 2000
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Fenjin He, Mohamad I. Farbood, Laura E. Kizer
  • Patent number: 6100410
    Abstract: A process for the production of at least one C.sub.4 compound selected from butane-1,4-diol, .gamma.-butyrolactone and tetrahydrofuran comprises contacting a vaporous stream containing maleic anhydride vapour, water vapour, and carbon oxides in an absorption zone with a high boiling organic solvent thereby to form a solution of maleic anhydride in the high boiling organic solvent. Maleic anhydride in this solution is reacted under esterification conditions in an esterification zone with a C.sub.1 to C.sub.4 alkanol to form a solution of the corresponding di-(C.sub.1 to C.sub.4 alkyl) maleate in the high boiling solvent. This solution of the di-(C.sub.1 to C.sub.4 alkyl) maleate in the high boiling solvent is contacted with a gaseous stream containing hydrogen thereby to strip di-(C.sub.1 to C.sub.4 alkyl) maleate therefrom and to form a vaporous stream comprising hydrogen and di-(C.sub.1 to C.sub.4 alkyl) maleate.
    Type: Grant
    Filed: November 12, 1998
    Date of Patent: August 8, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael William Marshall Tuck, Michael Anthony Wood, Andrew George Hiles
  • Patent number: 6008384
    Abstract: An improved two step (dual stage catalysis) aqueous hydrogenation process and a novel trimetallic hydrogenation catalysts consisting essentially of highly dispersed, reduced ruthenium and rhenium metals in the presence of a third metal tin on carbon support particular useful in the second stage of the process. Such process and catalyst exhibit high conversion rates in aqueous solution hydrogenation of hydrogenatable precursors (e.g., maleic acid, succinic acid, corresponding esters, .gamma.-butyrolactone, etc.) to tetrahydrofuran, .gamma.-butyrolactone, 1,4-butanediol and mixtures thereof wherein the relative molar ratio of 1,4-butanediol to tetrahydrofuran products being produced can be controlled.
    Type: Grant
    Filed: March 3, 1998
    Date of Patent: December 28, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Richard Edmond Bockrath, Daniel Campos, Jo-Ann Theresa Schwartz, Richard Thomas Stimek
  • Patent number: 6001781
    Abstract: The present invention is directed to a process for preparing a condensation product of a glyoxylic reactant and a hydrocarbyl-substituted aromatic compound having at least one hydroxy functionality, which includes (a) providing the glyoxylic reactant in the form of a compound represented by the formula ##STR1## or its reactive equivalent, wherein R.sup.1 and R.sup.3 independently are hydrogen or hydrocarbyl group of 1 to about 4 carbon atoms; and R.sup.2 and R.sup.4 independently are hydrocarbyl groups of 1 to about 4 carbon atoms; (b) mixing the aromatic compound with the glyoxylic reactant; and (c) heating the mixture to a temperature of about 50.degree. C. to about 200.degree. C. in the presence of an acid catalyst for a sufficient time to form the condensation product.
    Type: Grant
    Filed: September 10, 1997
    Date of Patent: December 14, 1999
    Assignee: The Lubrizol Corporation
    Inventors: Mark R. Baker, Karen M. Hull, David L. Westfall
  • Patent number: 5936124
    Abstract: A synthesis of fluoxetine is disclosed. The process begins with a lower alkyl ester of 3-benzoylpropionic acid, which is reduced in the presence of a chiral ligand to produce the corresponding .gamma.-hydroxy ester, and the ester is cleaved. The free acid is then condensed with the alcohol to form a .gamma.-lactone, which is treated with ammonia to provide the .gamma.-hydroxy amide. The amide undergoes a Hoffman rearrangement to provide a 2-oxo-1,3 oxazine, which is reduced to 3-(methylamino)-1-phenyl-1-propanol. The alcohol is deprotonated and reacted with a 4-chloro- or 4-fluoro benzotrifluoride to provide fluoxetine free base.
    Type: Grant
    Filed: June 22, 1998
    Date of Patent: August 10, 1999
    Assignee: Sepacor Inc.
    Inventors: James Wallace Hilborn, Alex Roger Jurgens, Chris Hugh Senanayake
  • Patent number: 5892107
    Abstract: A method of producing dehydration products from one or more 5-carbon or 6-carbon sugars includes reacting said one or more sugars at 40.degree.-240 .degree. C. for 1 to 96 hours in the presence of 10-90% sulfuric acid, separating the reaction products, and recovering levulinic acid. The sugars can be generated from strong acid hydrolysis of biomass, such as rice straw, paper, cotton and other cellulosic materials.
    Type: Grant
    Filed: November 8, 1996
    Date of Patent: April 6, 1999
    Assignee: Arkenol, Inc.
    Inventors: William A. Farone, John E. Cuzens
  • Patent number: 5859263
    Abstract: The present invention relates to a continuous process for preparing levulinic acid from starch in a reactive extrusion process. In a preferred embodiment, the extrusion takes place in a twin-screw extruder having a plurality of temperature zones wherein the starch slurry is preconditioned, extruded, filter pressed, reboiled, vacuum distilled, condensed, centrifuged, whereby the waste effluent from the centrifugation is reprocessed upstream to the preconditioning stage.
    Type: Grant
    Filed: August 14, 1996
    Date of Patent: January 12, 1999
    Assignee: Board of Regents University of Nebraska Lincoln
    Inventors: Viswas M. Ghorpade, Milford A. Hanna
  • Patent number: 5808107
    Abstract: Preparation of 4-hydroxy substituted butyrolactones is described. A process for the preparation of 3-hydroxybutyrolactone, 1,2,4-trihydroxybutane and 3,4-dihydroxy acid methyl ester from malic acid is particularly described. The preparation of 4-hydroxymethyl-4-hydroxybutyric acid -1-methyl ester and 4-hydroxymethyl butyrolactone is particularly described. The compounds are intermediates to various pharmaceutical and agricultural products.
    Type: Grant
    Filed: October 31, 1997
    Date of Patent: September 15, 1998
    Assignee: Board of Trustees operating Michigan State University
    Inventor: Rawle I. Hollingsworth
  • Patent number: 5792875
    Abstract: A process for the preparation of supported bimetallic catalyst useful for the hydrogenation of esters of dicarboxylic acids, which comprises impregnating activated alumina powder with transition metal by contacting the said solid alumina powder with an aqueous solution of a salt of a transition metal, treating the said transition metal salt impregnated alumina powder with an aqueous solution of a salt of group (IV) metal in acidic medium so as to have ratio of transition metal to group (IV) A metal in the range of 1:5 to 1:20, further treating the bimetallic impregnated alumina powder with an alkali solution followed by a solution of boron containing compound, finally washing and drying the resultant supported catalyst.
    Type: Grant
    Filed: June 4, 1996
    Date of Patent: August 11, 1998
    Assignee: Council of Scientific & Industrial Research
    Inventors: Raghunath Vitthal Chaudhari, Subhash Hari Vaidya
  • Patent number: 5629432
    Abstract: This appliciation discloses a process for preparing a lactone of general formula (I), where R is an optionally substituted phenyl group or an optionally substituted mono- or bicyclic heteroaryl radical which process comprises reacting an anion of a malonate of formula (II) with an ethylene compound of formula (III) Y--CH.sub.2 --CH.sub.2 OZ, to give a compound of formula (IV) and hydrolysing the compound of formula (IV) to give a lactone of formula (I). The lactones are of use as intermediates for preparing 5-HT.sub.1A binding agents.
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: May 13, 1997
    Assignee: John Wyeth & Brother, Ltd.
    Inventor: Robin G. Shepherd
  • Patent number: 5627288
    Abstract: Disclosed are 3,7-dimethyl-4-oxo-7-octenoic acid and its alkyl esters which are intermediates for producing a fragrance, rosefuran and which are represented by: ##STR1## where R is H or a lower alkyl. The compounds [1] are obtained by reacting 2-methyl-3-alkoxycarbonylpropionic acid halide and 3-methyl-3-butenylmagnesium halide. The octenoic acid [1] is treated with acetic anhydride under heat in the presence of an acidic catalyst to give 3,7-dimethyl-2,6-octadien-4-olide. The olide is reduced in an ordinary manner to give rosefuran.
    Type: Grant
    Filed: March 11, 1996
    Date of Patent: May 6, 1997
    Assignee: Toyotama Perfumery Co., Ltd.
    Inventors: Hidemichi Fukawa, Masamichi Nishitani, Mitsuo Chiba, Ruriko Murakami
  • 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: 5502217
    Abstract: A lactone is prepared by catalytically hydrogenating a dicarboxylic acid having 3 to 10 carbon atoms or a functional derivative thereof in the presence of a catalyst comprising a metal selected from the elements of group VIII of the periodic table or a combination of said metal with an element selected from the elements of groups IVa, VIb and VIIb of the peridic table, and further in the co-presence of an alkali metal salt or an alkali metal hydroxide.
    Type: Grant
    Filed: October 25, 1994
    Date of Patent: March 26, 1996
    Assignees: Tosoh Corporation, Sagami Chemical Research Center
    Inventors: Takamasa Fuchikami, Noriko Wakasa, De-Hua He, Takanori Miyake, Takashi Okada, Atsushi Fujimura, Hiroyuki Sasakibara, Yoshiaki Kanou, Toshihiro Saito
  • Patent number: 5478952
    Abstract: Improved hydrogenation catalysts consisting essentially of highly dispersed, reduced ruthenium and rhenium on carbon support and methods of making and using the same. Such catalysts exhibit high conversion rates in aqueous solution hydrogenation of hydrogenatable precursors (e.g., maleic acid, succinic acid, .gamma.-butyrolactone, etc.) to tetrahydrofuran, 1,4-butanediol and mixtures thereof.
    Type: Grant
    Filed: March 3, 1995
    Date of Patent: December 26, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Jo-Ann T. Schwartz
  • Patent number: 5468881
    Abstract: After the lactone portion of trans-whiskey lactone is hydrolyzed with potassium hydroxide, this portion is reacted with isopropyl bromide and mixed with an alkyl group, thereby obtaining isopropyl (3S,4S)-4-hydroxy-3-methyloctanoate. Then, the isopropyl (3S,4S)-4-hydroxy-3-methyloctanoate is reacted with diethyl azodicarboxylate in the presence of triphenylphosphine and azodicarboxylate, thereby obtaining isopropyl (3S,4S)-4-(3',5'-dinitrobenzoyloxy)-3-methyloctanoate. The isopropyl (3S,4S)-4-(3',5'-dinitrobenzoyloxy)-3-methyloctanoate is hydrolyzed in 2% potassium hydroxide, and as a result, cis-whiskey lactone (A) represented by the following general formula is obtained. According to this method, cis-whiskey lactone, one of the perfume components of whiskey and wine, can be produced selectively and easily.
    Type: Grant
    Filed: August 27, 1992
    Date of Patent: November 21, 1995
    Assignees: Japan Tobacco Inc., Yuji Gosei Kogyo Co., Ltd.
    Inventors: Takashi Ebata, Katsuya Matsumoto, Koshi Koseki, Hiroshi Kawakami, Hajime Matsushita, Hajime Yoshikoshi, Masakazu Okaniwa
  • Patent number: 5453516
    Abstract: A process for preparing 5-membered ring heterocycles of the general formula I ##STR1## where R.sup.1 is methyl or hydroxyethyl,R.sup.2,R.sup.3,R.sup.4,R.sup.5 and R.sup.6 are hydrogen, C.sub.1 - to C.sub.12 -alkyl, C.sub.2 - to C.sub.12 -alkenyl, aryl, C.sub.3 - to C.sub.8 -cycloalkyl, C.sub.1 - to C.sub.12 -alkoxy, halogen, C.sub.2 - to C.sub.20 -alkoxycarbonylalkyl, C.sub.2 - to C.sub.20 -alkylcarbonyloxy, formyl, C.sub.2 - to C.sub.20 -formylalkyl, benzoyl or --CH(OR.sup.3)(OR.sup.5), or R.sup.3 and R.sup.5 together are a C.sub.2 - to C.sub.7 -alkylene chain which is unsubstituted or monosubstituted to pentasubstituted by R.sup.4 or a .dbd.CH--CH.dbd.CH--CH.dbd. unit which is unsubstituted or monosubstituted to tetrasubstituted by R.sup.4,X is oxygen or N--R.sup.4by reacting 5-membered ring heterocycles of the general formula II ##STR2## where R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and X have the abovementioned meanings and Y is hydrogen, acetyl or C.sub.2 - to C.sub.
    Type: Grant
    Filed: December 13, 1993
    Date of Patent: September 26, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Rolf Pinkos
  • Patent number: 5420306
    Abstract: A process for producing an optically active .gamma.-butyrolactone derivative represented by formula (II): ##STR1## wherein R.sup.1 represents an alkyl group having from 1 to 10 carbon atoms or a substituted or unsubstituted phenyl group; and * indicates an asymmetric carbon atom, is disclosed, comprising enantioselectively hydrogenating a .gamma.-keto acid or an ester thereof represented by formula (I): ##STR2## wherein R.sup.1 and * are as defined above; and R.sup.2 represents a hydrogen atom or a lower alkyl group, in the presence of an optically active ruthenium-phosphine complex. The compounds (I) can be obtained at high optical purity through simple operations and a reduced number of steps.
    Type: Grant
    Filed: August 29, 1991
    Date of Patent: May 30, 1995
    Assignee: Takasago International Corporation
    Inventors: Ryoji Noyori, Masato Kitamura, Takeshi Ohkuma, Noboru Sayo, Hidenori Kumobayashi
  • Patent number: 5391771
    Abstract: A process for the preparation of propane-1,2,3-tricarboxylic acid, tetrahydrofurfurylacetic acid and the C.sub.1 - to C.sub.20 -alkyl or C.sub.7 - to C.sub.12 -aralkyl esters thereof, propane-1,2,3-trimethanol, 3-methyltetrahydrofuran, 3-(2'-hydroxyethyl)tetrahydrofuran, 4-hydroxymethyltetrahydropyran, 2-methyl-.gamma.-butyrolactone and/or 3-methyl-.gamma.-butyrolactone, comprises reacting citric acid or the C.sub.1 - to C.sub.20 -alkyl or C.sub.7 - to C.sub.12 -aralkyl esters thereof on hydrogenation catalysts in non-aqueous solvents at from 50.degree. to 400.degree. C. and at from 1 to 400 bar.
    Type: Grant
    Filed: September 30, 1993
    Date of Patent: February 21, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Juergen Weyer, Rolf Fischer, Christoph Sigwart
  • Patent number: 5347021
    Abstract: Vapor phase catalytic hydrogenation of maleic anhydride to gamma-butyrolactone is achieved in a conversion of 95% or more and a selectivity of 80% or more during a prolonged period of production. The process uses an activated catalyst prepared by reducing a catalyst composition comprising 30-65% by weight of CuO, 18-50% by weight of ZnO and 8-22% by weight of Al.sub.2 O.sub.3, and activating the reduced catalyst composition in hydrogen at an activation temperature of at least 400.degree. C., preferably 400.degree. to 525.degree. C., and optimally about 425.degree. C. The process suitably is carried out under predetermined and advantageous process conditions, including a defined molar ratio of hydrogen to maleic anhydride in the vapor reactant stream, a selected pressure during hydrogenation, a defined feed rate space velocity, a predetermined contact time, and a suitable reaction temperature.
    Type: Grant
    Filed: February 19, 1991
    Date of Patent: September 13, 1994
    Assignee: ISP Investments Inc.
    Inventors: Paul D. Taylor, Waldo De Thomas, Donald W. Buchanan, Jr.
  • Patent number: 5319110
    Abstract: A process for the preparation of 3,4-dihydroxybutanoic acid (1) and salts thereof from a glucose source containing 1,4-linked glucose as a substituent is described. The process uses an alkali metal hdyroxide and hydrogen peroxide to convert the glucose source to (1). The compound (1) is useful as a chemical intermediate to naturally occurring fatty acids and is used to prepare 3,4-dihydroxybutanoic acid-gamma-lactone (2) and furanone (3), particularly stereoisomers of these compounds.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: June 7, 1994
    Assignee: Board of Trustees operating Michigan State University
    Inventor: Rawle I. Hollingsworth
  • Patent number: 5319111
    Abstract: A process for the preparation of tetrahydrofuran or tetrahydrofuran and .gamma.-butyrolactone from the product of the hydrogenation of maleic acid, succinic acid, maleic anhydride, succinic anhydride and/or fumaric acid, by treating the crude hydrogenation product, without prior work-up, at from 100.degree. to 300.degree. C. with a protic acid, and isolating pure tetrahydrofuran and .gamma.-butyrolactone from the resultant reaction mixture by distillation.
    Type: Grant
    Filed: August 17, 1992
    Date of Patent: June 7, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Zimmermann, Karl Brenner, Hans-Juergen Scheiper, Wolfgang Sauer, Horst Hartmann
  • Patent number: 5296595
    Abstract: A chiral catalyst is disclosed together with methods of using it for enantioselective syntheses. The chiral catalyst includes a nucleus with two metal atoms that has four bridging ligands oriented radially to the axis of the nucleus. Each of these ligands includes a two complexing atoms each complexed to one of the metal atoms. At least one of the bridging ligands includes a chiral center which is bonded to one of the complexing atoms. Preferably, all four of the bridging ligands include a chiral center bonded to one of the complexing atoms. The catalyst of the invention has been found to be useful in catalyzing carbenoid transformation reactions such as cyclopropanation.
    Type: Grant
    Filed: September 24, 1992
    Date of Patent: March 22, 1994
    Assignee: Research Corporation Technologies
    Inventor: Michael P. Doyle
  • Patent number: 5274128
    Abstract: Described is a process for the preparation of compositions of matter containing octalactones defined according to the structure: ##STR1## which includes the stereoisomers having the structures: ##STR2## by means of the sequential steps of (i) fermentation of caprylic acid or the ethyl ester of caprylic acid defined according to the generic structure: ##STR3## wherein R is hydrogen or ethyl using a microorganism selected from the group consisting of:Mortierella ramanniana var. ramanniana--CBS 112.08Mortierella ramanniana var. ramanniana--CBS 478.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: December 28, 1993
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mohamad I. Farbood, Lynda B. McLean, James A. Morris, Henry A. Bondarovich
  • Patent number: 5254697
    Abstract: The invention provides a novel process for the manufacture of enantiomerically-pure halolactones of the formula I which are useful for the production of certain 5-amino-4-hydroxyvaleric acid derivatives, themselves valuable intermediates in the production of compounds which are renin inhibitors. The process involves a diastereoselective alkylation of an oxazolidinone of the formula III, followed by a highly stereoselective and novel halolactonisation of an oxazolidinone of the formula II. Certain of the oxazolidinones of the formula II are novel and are provided as a further feature of the invention. The invention also provides a novel process for the production of the pharmaceutically-useful 5-amino-4-hydroxyvaleric acid derivatives of formula VI.
    Type: Grant
    Filed: June 4, 1990
    Date of Patent: October 19, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventor: David Waterson
  • Patent number: 5191091
    Abstract: A process for hydrogenating bound oxygen-containing organic feeds into their corresponding alcohols by contact with a coprecipitated copper-aluminum catalyst that has been activated by contact with reducing gas at a temperature that gradually increases.
    Type: Grant
    Filed: January 27, 1992
    Date of Patent: March 2, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Richard W. Wegman, David R. Bryant
  • Patent number: 5189182
    Abstract: 5-Methylbutyrolactone is prepared by a process in which a pentenoic ester of the formula IX--CO.sub.2 R (I),where X is CH.sub.2 .dbd.CH--CH.sub.2 --CH.sub.2 --, CH.sub.3 --CH.dbd.CH--CH.sub.2 -- or CH.sub.3 --CH.sub.2 --CH.dbd.CH-- and R is alkyl, cycloalkyl, aralkyl or aryl, or a mixture of these esters is reacted with water at from 50.degree. to 350.degree. C. in the presence or absence of a diluenta) over a zeolite and/or phosphate catalyst orb) in the presence of from 0.01 to 0.25 mole of a sulfonic acid, a Lewis acid and/or a non-oxidizing mineral acid per mole of pentenoic ester or over from 0.
    Type: Grant
    Filed: August 25, 1988
    Date of Patent: February 23, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Kummer, Heinz-Walter Schneider, Werner Bertleff, Rolf Fischer, Uwe Vagt, Fritz Naeumann, Wolfgang Hoelderich, Matthias Schwarzmann
  • Patent number: 5175311
    Abstract: A chiral catalyst is disclosed together with methods of using it for enantioselective syntheses. The chiral catalyst includes a nucleus with two metal atoms that has four bridging ligands oriented radially to the axis of the nucleus. Each of these ligands includes two complexing atoms each complexed to one of the metal atoms. At least one of the bridging ligands includes a chiral center which is bonded to one of the complexing atoms. Preferably, all four of the bridging ligands include a chiral center bonded to one of the complexing atoms. The catalyst of the invention has been found to be useful in catalyzing carbenoid transformation reactions such as cyclopropanation.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: December 29, 1992
    Assignee: Research Corporation Technologies, Inc.
    Inventor: Michael F. Doyle
  • Patent number: 5166366
    Abstract: Described is a process for the preparation of compositions of matter containing octalactones defined according to the structure: ##STR1## which includes the stereoisomers having the structures: ##STR2## by means of the sequential steps of (i) fermentation of caprylic acid or the ethyl ester of caprylic acid defined according to the generic structure: ##STR3## wherein R is hydrogen or ethyl using a microorganism selected from the group consisting of:Mortierella isabellina, ATCC 44583;Mortierella isabellina, ATCC 38063;Syncephalastrum racemosum, NRRL A-5889;Mortierella isabellina, IFO 7884;Mortierella ramanniana var. angulispora, IFO 8187;Mortierella isabellina, CBS 221.
    Type: Grant
    Filed: January 23, 1992
    Date of Patent: November 24, 1992
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mohamad I. Farbood, Lynda B. McLean, James A. Morris, Henry A. Bondarovich
  • Patent number: 5149836
    Abstract: This invention provides a vapor phase process for the production of gamma-butyrolactone and tetrahydrofuran in a predetermined ratio by the steps of: hydrogenating a vapor mixture of maleic anhydride and excess hydrogen over a first bed of a Cu-Zn-Al catalyst, and directly contacting the crude reactor effluent therefrom with hydrogen over a second bed of Cu-Zn-Cr catalyst during a predetermined contact time and at a defined temperature, using selected amounts of catalyst in each bed.
    Type: Grant
    Filed: July 25, 1991
    Date of Patent: September 22, 1992
    Assignee: ISP Investments Inc.
    Inventors: Waldo De Thomas, Paul D. Taylor, Heinn F. Tomfohrde, III
  • Patent number: 5142067
    Abstract: A process for hydrogenating feeds into their corresponding alcohols by contact with a coprecipitated catalyst comprising copper, aluminum, and a metal (X) selected from the group consisting of magnesium, zinc, titanium, zirconium, tin, nickel, cobalt and mixtures thereof; that has been reduced with an increasing temperature during the reduction.
    Type: Grant
    Filed: November 5, 1991
    Date of Patent: August 25, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Richard W. Wegman, David R. Bryant
  • Patent number: 5136058
    Abstract: This invention relates to a process for the recovery of purified gamma-butyrolactone (BLO) in high yield from its crude reactor effluent containing BLO, tetrahydrofuran (THF), water, the acid-catalyzed hydrolysis product of BLO which is 4-hydroxybutyric acid (4-HBA), light and heavy organic acids, and alcohols. The process is particularly characterized by flash vaporizing a THF-free mixture of BLO, 4-HBA, water, light acids such as butyric acid and propionic acid, and alcohols so that the 4-HBA component is recyclized to form additional BLO. Heavy acids such as succinic acid and maleic acid are removed from the bottom.The total amount of BLO in the vapor stream then is fed to a distillation column where it is condensed; the water, including the water of dehydration, and light acid and alcohol impurities in the distillation are separated overhead from the BLO and removed. This procedure prevents BLO from further acid hydrolysis while the water of dehydration from 4-HBA is recovered.
    Type: Grant
    Filed: July 25, 1991
    Date of Patent: August 4, 1992
    Assignee: ISP Investments Inc.
    Inventors: Paul D. Taylor, Michael Aversa, Waldo De Thomas, Donald Buchanan
  • Patent number: 5079372
    Abstract: A method for producing a lactone by hydrogenating a dicarboxylic acid, a dicarboxylic acid anhydride and/or a dicarboxylic acid ester in the presence of a catalyst, wherein the hydrogenation reaction is conducted in the liquid phase in the presence of (1) ruthenium, (2) an organic phosphine and (3) a compound of a metal selected from the group consisting of Groups IVA, VA and IIIB in the Periodic Table.According to the present invention, for the production of a lactone by hydrogenating a dicarboxylic acid, a dicarboxylic acid anhydride and/or a dicarboxylic ester, the reaction is conducted in a homogeneous liquid phase reaction by using the ruthenium,organic phosphine and compound of a metal selected from the group consisting of Groups IVA, VA and IIIB, of the present invention as the catalyst, whereby the desired lactone product can be obtained at high selectivity under a mild condition as compared with the conventional methods.
    Type: Grant
    Filed: May 1, 1990
    Date of Patent: January 7, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Keisuke Wada, Yoshinori Hara, Koushi Sasaki
  • Patent number: 5047561
    Abstract: A process for producing a lactone by reacting in a hydrogenation reaction zone a dicarboxylic acid, a dicarboxylic acid anhydride and/or a dicarboxylic acid ester with hydrogen in a liquid phase using a solvent in the presence of a catalyst comprising ruthenium and an organic phosphine, which process comprises the following steps (1) to (6):(1) a first step of recovering the liquid phase from the hydrogenation reaction zone,(2) a second step of distilling the liquid phase in a first distillation column to obtain a first distillate and a first residue,(3) a third step of recycling the first residue to the hydrogenation reaction zone,(4) a fourth step of distilling a part of the first residue in a second distillation column to obtain a second distillate and a second residue,(5) a fifth step of recycling the second distillate to the hydrogenation reaction zone or the first distillation column, and(6) a sixth step of recovering a lactone from the first distillate.
    Type: Grant
    Filed: September 14, 1990
    Date of Patent: September 10, 1991
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Chihiro Miyazawa, Kazunari Takahashi, Hiroshi Kameo, Shinji Isogai, Masayuki Otake
  • Patent number: 5041564
    Abstract: What is provided herein is a vapor phase process for the production of butyrolactone in which the vapor mixture of the feed compound and hydrogen is provided at high flow rates from finely divided droplets of the feed compound which are vaporized rapidly with hot hydrogen gas.
    Type: Grant
    Filed: April 16, 1990
    Date of Patent: August 20, 1991
    Assignee: GAF Chemicals Corporation
    Inventor: Donald W. Buchanan, Jr.
  • Patent number: 5032611
    Abstract: Disclosed in the present invention are: a substance F-0368 or salts thereof having the following structural formula ##STR1## a method for production of the substance F-0368 or salts thereof, wherein an F-0368-substance-producing-microorganism belonging to a genus Kitasatosporia is cultured, and the substance F-0368 is isolated and collected from the cultured substance; a method for production of the substance F-0368 or salts thereof, wherein 3-methyl-4-lower alkoxy carbonyl-2(5H)-furanone represented by the following general formula is subjected to hydrolytic reaction ##STR2## (where: R represents a straight or branched lower alkyl group having 1 to 6 carbon atoms); a composition which consists essentially of the substance F-0368 or salt thereof, a diluent permissible in the agricultural chemicals, and a carrier or an excipient; a preventive agent for plant diseases such as rice blast disease and bacterial leaf blight disease, which consists essentially of an effective amount of the substance F-0368 or salts
    Type: Grant
    Filed: March 8, 1989
    Date of Patent: July 16, 1991
    Assignee: Kaken Pharmaceutical Co., Ltd.
    Inventors: Ryusuke Taguchi, Hideo Sugawara, Yukio Miyazaki, Taku Mizuno, Masahide Nomura, Machiko Sugiyama, Hideo Saito, Goro Yabuta, Akiya Furuichi, Yasuhiko Hamazaki, Katsuhiro Nakamura
  • Patent number: 5021589
    Abstract: A method for producing a lactone by hydrogenating a dicarboxylic acid, a dicarboxylic acid anhydride and/or a dicarboxylic acid ester in the presence of a catalyst, wherein said catalyst is a ruthenium catalyst comprising (1) ruthenium, (2) an organic phosphine and (3) a conjugate base of an acid having a pKa of less than 2.
    Type: Grant
    Filed: October 30, 1989
    Date of Patent: June 4, 1991
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Keisuke Wada, Yoshinori Hara, Koushi Sasaki
  • Patent number: 4997955
    Abstract: 1,1-disubstituted ethylene compounds of the general formula I ##STR1## where Z is COOR.sup.2, CN or COR.sup.3, R.sup.1 is an aliphatic, cycloalophatic, araliphatic, aromatic or heterocyclic radical which may be further substituted by functional groups which are inert under the reaction conditions, R.sup.2 is an aliphatic, cycloaliphatic or araliphatic radical of 1 to 15 carbon atoms and R.sup.3 is an aliphatic, cycloaliphatic or araliphatic radical of 1 to 15 carbon atoms which may be substituted by groups which are inert under the reaction conditions, and R.sup.1 together with R.sup.2 or R.sup.1 together with R.sup.3 may furthermore form an alkylene chain of 2 to 10 carbon atoms which may be substituted by groups which are inert under the reaction conditions, are prepared from a formyl compound of the general formula II ##STR2## where Z, R.sup.1, R.sup.2 and R.sup.3 have the above meanings, by a process in which the reaction is carried out in the presence of formaldehyde or paraformaldehyde and(a) a C.sub.
    Type: Grant
    Filed: June 10, 1988
    Date of Patent: March 5, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Joerg Liebe, Werner Bertleff
  • Patent number: 4985572
    Abstract: An alcohol and/or a carboxylic acid ester is produced from a carboxylic acid or anhydride thereof by reacting the acid or anhyride with hydrogen at elevated temperature in the presence as catalyst of a composition comprising an alloy of (i) at least one noble metal of Group VIII of the Periodic Table and (ii) at least one metal capable of alloying with the Group VIII noble metal, optionally including a support and at least one of the metals rhenium, tungsten or molybdenum. The process is particularly applicable to the hydrogenation of monobasic acids, for example acetic acid, and the hydrogenation of maleic acid or maleic anhydride to gamma-butyrolactone.
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: January 15, 1991
    Assignees: The British Petroleum Company, p.l.c., BP Chemicals Limited
    Inventors: Melanie Kitson, Peter S. Williams
  • Patent number: 4973713
    Abstract: A process for the production of esters or lactones, comprising reacting in the presence of a catalyst and under hydrogenation conditions hydrogen and an acyclic or cyclic carboxylic anhydride to produce the corresponding ester or lactone, wherein the catalyst is a supported catalyst comprising:(a) a group VIII metal, Re and Fe;(b) a group VIII metal on TiO.sub.2 ;(c) Ru and at least one of Re, Ag or Cu; or(d) Pd and Fe.Preferably, the anhydride has the formula ##STR1## and is reacted to form an ester of the formula ##STR2## or a lactone of the formula ##STR3## wherein R and R.sup.1 independently are lower alkyl or cycloalkyl; R.sup.2, R.sup.3, R.sup.4, R.sup.5 independently are hydrogen, lower alkyl, cycloalkyl or aryl; and wherein R.sup.3 and R.sup.4 taken together may form a saturated or unsaturated ring, or an aromatic ring. The more preferred starting material is phthalic anhydride.
    Type: Grant
    Filed: November 28, 1989
    Date of Patent: November 27, 1990
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: William H. Manogue
  • Patent number: 4948905
    Abstract: Synthesis of vinyl lactones by means of palladium catalyzed coupling of vinylic halides or triflates and certain unsaturated carboxylic acids.
    Type: Grant
    Filed: September 18, 1989
    Date of Patent: August 14, 1990
    Assignee: Iowa State University Reasearch Foundation, Inc.
    Inventor: Richard C. Larock
  • Patent number: 4945173
    Abstract: A process is described for the production of substantially pure gamma-butyrolactone from a feed mixture containing a major amount of gamma-butyrolactone and a minor amount of diethyl succinate which comprises fractionally distilling the mixture in a fractionation zone in the presence of diethyl ethoxysuccinate and recovering from the fractionation zone an overhead vaporous product comprising gamma-butyrolactone which is substantially free from diethyl succinate and is liquid bottom product comprising diethyl ethoxysuccinate and diethyl succinate in admixture one with another. This procedure can be used to separate a gamma-butyrolactone rich fraction obtained by distillation in one or more stages of a crude reaction product obtained by hydrogenation of a C.sub.
    Type: Grant
    Filed: July 22, 1988
    Date of Patent: July 31, 1990
    Assignee: Davy McKee (London) Limited
    Inventor: Michael A. Wood
  • Patent number: 4940805
    Abstract: Process for the preparation of 1,4-butanediol or tetrahydrofuran or both by the catalytic hydrogenation of maleic anhydride, succinic anhydride, maleic acid, succinic acid, fumaric acid, or the alkyl esters of these acids at temperatures of from 100.degree. C. to 350.degree. C. and pressures of from 50 bar to 350 bar over a catalyst containing cobalt as the active metal and one or both of the elements copper and phosphorus, if necessary in the presence of an aliphatic alcohol.
    Type: Grant
    Filed: August 8, 1988
    Date of Patent: July 10, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Hans-Juergen Gosch, Wolfgang Harder, Klaus-Dieter Malsch, Manfred Eggersdorfer, Lothar Franz, Horst Zimmermann, Karl Brenner, Klaus Halbritter, Wolfgang Sauer, Hans-Juergen Scheiper
  • Patent number: 4931573
    Abstract: A method for producing a lactone by hydrogenating a dicarboxylic acid, a dicarboxylic acid anhydride and/or a dicarboxylic acid ester in the presence of a catalyst, wherein the hydrogenation reaction is conducted in the liquid phase in the presence of (1) ruthenium, (2) an organic phosphine and (3) a compound of a metal selected from the group consisting of Groups IVA, VA and IIIB in the Periodic Table.According to the present invention, for the production of a lactone by hydrogenating a dicarboxylic acid, a dicarboxylic acid anhydride and/or a dicarboxylic ester, the reaction is conducted in a homogeneous liquid phase reaction by using the ruthenium, organic phosphine and compound of a metal selected from the group consisting of Groups IVA, VA and IIIB, of the present invention as the catalyst, whereby the desired lactone product can be obtained at high selectivity under a mild condition as compared with the conventional methods.
    Type: Grant
    Filed: April 4, 1988
    Date of Patent: June 5, 1990
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Keisuke Wada, Yoshinori Hara, Koushi Sasaki