The Lactone Ring Is Five-membered Patents (Class 549/295)
  • Patent number: 4988825
    Abstract: Aldehydes and ketones, other than acetone, are oxidized with an alkali metal perborate in the presence of an acid.
    Type: Grant
    Filed: September 23, 1986
    Date of Patent: January 29, 1991
    Assignee: Cooper Union Research Foundation, Inc.
    Inventor: John L. Bove
  • Patent number: 4968817
    Abstract: A process for preparing a substituted or unsubstituted gamma-crotonolactone is provided which comprises reacting a substituted or unsubstituted glycidol of the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.
    Type: Grant
    Filed: July 10, 1989
    Date of Patent: November 6, 1990
    Assignee: National Distillers and Chemical Corporation
    Inventor: Thomas S. Brima
  • Patent number: 4960906
    Abstract: Process for the preparation of lactones, having 4 or 5 carbon atoms in the ring by reacting a higher alkenol with a carbon monoxide containing gas in the presence of a catalytic system comprising(a) a palladium compound,(b) a bidentate phosphine, arsine and/or stibine, and(c) a protonic acid having a pK.sub.a <2.
    Type: Grant
    Filed: April 25, 1989
    Date of Patent: October 2, 1990
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4954623
    Abstract: A process for recycling the difluoro sugar in the synthesis of 2,2-difluoronucleosides proceeds by removing the base moiety of .alpha.-difluoronucleosides by reduction and hydrolysis, followed by oxidation to put the difluro sugar in a form conventiently recycled into the synthesis, and intermediates useful therefor.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: September 4, 1990
    Assignee: Eli Lilly and Company
    Inventor: Ramakrishnan Nagarajan
  • 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: 4943652
    Abstract: There is disclosed a process for asymmetrically reducing a carbonyl compound, which comprises reducing the carbonyl compound by the use of a reducing agent comprising (i) an optically active tartaric acid or ester thereof and (ii) a metal borohydride, thereby producing an optically active hydroxyl compound. The process can be used for the production of optically active hydroxyesters and alcohols from ketoesters and ketones. These products are useful for the production of medicaments and liquid crystals.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: July 24, 1990
    Assignee: Ajinomoto Co., Inc.
    Inventors: Masanobu Yatagai, Takashi Ohnuki
  • Patent number: 4919765
    Abstract: Tetrahydrofuran is recovered by a two stage distillation procedure from a crude hydrogenation product resulting from vapor phase hydrogenation of diethyl maleate and containing water, ethanol and a minor amount of n-butanol, and possibly also dissolved hydrogen, in addition to butane-1,4-diol, gamma-butyrolactone and "heavies" such as diethyl ethoxysuccinate. In the first distillation stage, conveniently operated substantially at atmospheric pressure, ethanol, water, and tetrahydrofuran are recovered as overhead product, are condensed to separate the condensible components from a hydrogen stream which can be vented, and then redistilled in the presence of a molar excess of a hydroxylic solvent containing at least two hydroxyl groups, such as butane-1,4-diol, in a second distillation zone.
    Type: Grant
    Filed: July 22, 1988
    Date of Patent: April 24, 1990
    Assignee: Davy McKee (London) Limited
    Inventors: Peter R. Wilkes, John Scarlett, George E. Harrison
  • Patent number: 4851085
    Abstract: A process which comprises treating butyrolactone in at least 95% purity with an acid to convert and remove color forming impurities for product stabilization.
    Type: Grant
    Filed: July 11, 1988
    Date of Patent: July 25, 1989
    Assignee: GAF Corporation
    Inventor: Waldo De Thomas
  • Patent number: 4851540
    Abstract: Process for the production of imidazole derivatives of the formula: ##STR1## wherein R.sub.1 is an (R)- or (S)-1-phenylalkyl group, an (R)- or (S)-1-alkoxycarbonyl-1-phenylmethyl group or an (R)- or (S)-1-aryloxycarbonyl-1-phenylmethyl group, R.sub.2 is hydrogen, a substituted or unsubstituted alkanoyl group, an unsubstituted or a substituted benzoyl group, a substituted or an unsubstituted benzyl group, an alkoxycarbonyl group, and aryloxycarbonyl group, an alkoxyalkyl group, a pyranyl group, a substituted or unsubstituted benzenesulfonyl group, an alkylsulfonyl group, a diarylphosphinyl group, a dialkoxyphosphinyl group or a trialkylsilyl group, and A is a sulfur or oxygen atom.
    Type: Grant
    Filed: December 1, 1987
    Date of Patent: July 25, 1989
    Assignee: Lonza Ltd.
    Inventors: John McGarrity, Leander Tenud, Thomas Meul
  • Patent number: 4843093
    Abstract: Butyrolactone derivatives having the formula ##STR1## wherein R is a C.sub.4 -C.sub.10 alkyl group, which have an appetite-regulating effect, a process for their production, and compositions containing them, are disclosed.
    Type: Grant
    Filed: May 29, 1987
    Date of Patent: June 27, 1989
    Assignee: Ajinomoto Co., Inc.
    Inventors: Yoichiro Nagai, Taichi Nakano, Yutaka Oomura
  • Patent number: 4767869
    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 added diethyl maleate and recovering from the fractionation zone an overhead vaporous product comprising gamma-butyrolactone which is substantially free from diethyl succinate and a liquid bottom product comprising diethyl maleate 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 31, 1987
    Date of Patent: August 30, 1988
    Assignee: Davy McKee Limited
    Inventors: George E. Harrison, Norman Harris
  • Patent number: 4659843
    Abstract: The invention relates to a process for preparing 3-methyl-2-butene-4-olide by the codimerization of methylenecyclopropane with carbon dioxide (CO.sub.2) in the presence of organic complex compounds of transistion metals, which process is characterized in that the codimerization is carried out at a temperature of 100.degree. C. to 200.degree. C. in the presence of palladium(O) compounds which are stable in the reaction mixture up to 200.degree. C. and with CO.sub.2 under a pressure of 10 to 110 bar, optionally in the presence of a solvent.
    Type: Grant
    Filed: February 1, 1985
    Date of Patent: April 21, 1987
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Paul Binger, Hans-Joachim Weintz
  • Patent number: 4634780
    Abstract: Lactones are produced by reacting an unsaturated alcohol capable of intramolecular esterification to form a lactone ring with carbon monoxide in the presence of a protonic acid and a catalyst comprising (a) at least one of the metals palladium, rhodium, ruthenium, iridium and cobalt, and (b) at least one of the metals copper, molybdenum and iron, the metals (a) and (b) being in the form of either the elemental metal or a compound thereof.
    Type: Grant
    Filed: September 24, 1985
    Date of Patent: January 6, 1987
    Assignee: The British Petroleum Company p.l.c.
    Inventors: Howard Alper, David J. H. Smith
  • Patent number: 4632784
    Abstract: The invention is directed to a process and intermediates for the preparation of 1.alpha., 23,25-trihydroxycholecalciferol-26-oic acid 23,26-lactone.
    Type: Grant
    Filed: July 30, 1984
    Date of Patent: December 30, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Enrico G. Baggiolini, Milan R. Uskokovic, Peter M. Wovkulich
  • Patent number: 4625049
    Abstract: A process for the preparation of carboxylic acids, alcohols, aldehydes or the secondary products thereof which comprises reacting an alcohol having from one to about twenty carbon atoms with hydrogen and carbon monoxide in the presence of a heterogeneous sulfided catalyst comprising nickel in admixture with a co-catalyst selected from the elements of Groups V-B, VI-B and the Actinide series of the Periodic Table.
    Type: Grant
    Filed: June 30, 1982
    Date of Patent: November 25, 1986
    Assignee: Chevron Research Company
    Inventor: Steven P. Current
  • Patent number: 4602006
    Abstract: Compounds of the formula ##STR1## wherein n is 1-3; R.sup.1, R.sup.2 and R.sup.3 are the same or different and are hydrogen, lower alkyl, lower alkenyl, lower alkynyl, aryl or aryl lower alkyl wherein when aryl is phenyl it is unsubstituted or independently substituted with one or more halo, lower alkyl or lower alkoxy groups; and R.sup.4 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, trialkylsilyl, aryl or aryl lower alkyl wherein when aryl is phenyl it is unsubstituted or independently substituted by one or more halo, lower alkyl or lower alkoxy groups; excluding those compounds wherein R.sup.1 and R.sup.2 are hydrogen and R.sup.4 is ethyl, propyl or butyl. These compounds are useful as protease inhibitors.
    Type: Grant
    Filed: May 9, 1984
    Date of Patent: July 22, 1986
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Alexander Krantz, Tim F. Tam, Robin W. Spencer
  • Patent number: 4596879
    Abstract: A novel process for the manufacture of the furanone of the formula ##STR1## is described. In this process, a diol is firstly reacted with thionyl chloride, then the sulphite formed, optionally after oxidation to the corresponding sulphate, is treated with sodium cyanide and the resulting hydroxynitrile is hydrolyzed.The furanone of formula I can be used as a starting material for the manufacture of R-(-)-pantolactone.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: June 24, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Christian Fizet
  • Patent number: 4473700
    Abstract: Disclosed are isomeric polyisobutenyl butyrolactones and lactams thereof useful as dispersants in lubricant oils and having the formulas: ##STR1## wherein R is a hydrocarbyl group having from 12 to 300 carbon atoms; X is O or >N--R', where R' is an alkyl or alkylamino group having from 1 to 20 carbon atoms and from 0 to 10 nitrogen atoms. The butyrolactones are made by mild reduction of the corresponding cyclic anhydrides and the lactams are prepared by reacting the intermediate butyrolactones with at least a molar equivalent of a primary amine, optionally, in the presence of a base or an acid.
    Type: Grant
    Filed: July 6, 1982
    Date of Patent: September 25, 1984
    Assignee: Texaco Inc.
    Inventor: Gary T. Babic
  • Patent number: 4465847
    Abstract: There is provided a one-step process for the production of diols.There is provided a process for the conversion of diols in a one-step reaction to polyesters and to lactones, wherein the diols are reacted in the presence of a Group VIII (of the Periodic Table) catalyst with an oxidizing agent, i.e. an agent adapted to remove hydrogen from the reactants, the process being carried out at elevated temperatures. According to a specific embodiment diols having a certain number of carbons are directly converted to lactones, while another embodiment provides for the conversion of but-2-yne-1, 4-diol to butyrolactone.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: August 14, 1984
    Assignee: Ramot University Authority for Applied Research and Industry Development Ltd.
    Inventor: Youval Shvo
  • Patent number: 4451407
    Abstract: Oxygenated organic compounds, e.g. esters, aldehydes, and amides, are prepared by reacting an olefinically unsaturated compound with carbon monoxide and a compound containing a replaceable hydrogen atom in the presence of a catalyst comprising cobalt or ruthenium carbonyl and a promoter ligand. The promoter ligand is selected from the group consisting of heterocyclic nitrogen oxide compounds and phosphorus or sulfur oxides. These reactions are carried out under relatively mild conditions of temperature and pressure.
    Type: Grant
    Filed: December 18, 1981
    Date of Patent: May 29, 1984
    Assignee: The Standard Oil Company
    Inventors: Frederick A. Pesa, Thomas A. Haase
  • Patent number: 4420622
    Abstract: The preparation of 5-alkyl-butyrolactones is described using C.sub.8 hydrocarbon levulinate esters, with side-chain alkyl substituents of up to 4 carbon atoms as starting material, with the reaction being conducted with hydrogen at a temperature of from 150.degree. to 325.degree. C., in the gas phase, and in the presence of a hydrogenation catalyst composed of metals of Group VIII or Group Ib of the Periodic Table. The process provides extremely high conversion rates and lactone yields, the prolonged catalyst activity.
    Type: Grant
    Filed: May 21, 1982
    Date of Patent: December 13, 1983
    Assignee: Stamicarbon B.V.
    Inventors: Cornelis G. M. van de Moesdijk, Petrus H. J. Janssen
  • Patent number: 4416902
    Abstract: Described are the organoleptic uses of the genus of compounds defined according to the structure: ##STR1## wherein the wavy lines represent the "cis" or "trans" juxtaposition of the methyl, cyclohexenyl, hydrogen and carboxaldehyde moieties around the carbon-carbon double bond, for augmenting or enhancing the flavor and/or aroma of consumable materials including foodstuffs, chewing gums, medicinal products, toothpastes, perfumes, colognes and perfumed articles.
    Type: Grant
    Filed: July 16, 1982
    Date of Patent: November 22, 1983
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Braja D. Mookherjee, Richard A. Wilson, Manfred H. Vock, Michael J. Zampino
  • Patent number: 4414079
    Abstract: The electrolytic reduction of a mixture of an acrylic ester and an aldehyde in the form of an aqueous emulsion in the presence of at least one phase-transfer catalyst using a lead or lead alloy cathode has been found to be very effective for preparing a 4-butanolide compound simply and safely in high yield with a high current efficiency.
    Type: Grant
    Filed: July 15, 1982
    Date of Patent: November 8, 1983
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Kazunori Yamataka, Toshiro Isoya, Nobuya Kitaguchi
  • Patent number: 4358601
    Abstract: A process for preparing 2-butenolide, a useful product for the manufacture of gamma-butyrolactone, is disclosed which comprises reacting furan with oxygen in the presence of a catalytically effective amount of a catalyst comprising a mixed metal oxide containing titanium, boron and molybdenum.
    Type: Grant
    Filed: July 2, 1981
    Date of Patent: November 9, 1982
    Assignee: National Distillers & Chemical Corp.
    Inventors: Jack Kwiatek, Thomas S. Brima
  • Patent number: 4356310
    Abstract: A mixture of gamma-butyrolactone and butenolide is obtained by reacting 1,3-butadiene with oxygen in the vapor phase at elevated temperature in the presence of a catalytically effective amount of a mixed metal oxide containing boron, molybdenum and titanium values.
    Type: Grant
    Filed: July 2, 1981
    Date of Patent: October 26, 1982
    Assignee: National Distillers & Chemical Corp.
    Inventor: Thomas S. Brima
  • Patent number: 4351839
    Abstract: This invention relates to 2-aryl-2-1-H-azoyl-(alkyl)gamma-butyrolactone of the formula: ##STR1## wherein Z is optionally substituted aryl;R is hydrogen, alkyl, alkenyl, alkynyl, optionally substituted aryl or optionally substituted aralkyl;Azo is 1-H-imidiazoyl, 1-H-1,2,4-triazoyl or 4-H-1,2,4-triazoyl;n is zero or an integer from 1 to 5, and the agronomically acceptable acid addition salts and metal salt complexes thereof, methods for their preparation and their use as pesticides.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: September 28, 1982
    Assignee: Rohm and Haas Company
    Inventor: Hak-Foon Chan
  • Patent number: 4331612
    Abstract: Oxygenated organic compounds, e.g. esters, aldehydes, and amides, are prepared by reacting an olefinically unsaturated compound with carbon monoxide and a compound containing a replaceable hydrogen atom in the presence of a catalyst comprising cobalt or ruthenium carbonyl and a promoter ligand. The promoter ligand is selected from the group consisting of heterocyclic nitrogen oxide compounds and phosphorus or sulfur oxides. These reactions are carried out under relatively mild conditions of temperature and pressure.
    Type: Grant
    Filed: July 16, 1980
    Date of Patent: May 25, 1982
    Assignee: Standard Oil Company
    Inventors: Frederick A. Pesa, Thomas A. Haase