Preparing From Compound Containing -coo- Group Patents (Class 549/326)
  • Patent number: 4853473
    Abstract: 2(5H)-furanones I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 - or C.sub.6 -cycloalkyl, C.sub.7 -C.sub.12 -aralkyl or aryl, are prepared by heating a 3-formylcarboxylate or 3-formylcarboxylic acid II ##STR2## where R.sup.3 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.5 - or C.sub.6 -cycloalkyl, C.sub.7 -C.sub.12 -aralkyl or aryl, to 100.degree.-450.degree. C. in the presence of an acidic catalyst.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: August 1, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Juergen Frank, Franz Merger, Michael Roeper, Uwe Vagt
  • Patent number: 4831166
    Abstract: .gamma.-butyrolactones of the general formula I ##STR1## where R.sup.1 is hydrogen or alkyl of 1 to 4 carbon atoms which may be substituted by lower alkoxy or acyloxy and R.sup.2 is hydrogen or straight-chain or branched alkyl which is unsubstituted or substituted by a functional group or is aryl, are prepared by reacting an alkylene oxide of the general formula II ##STR2## with an acylacetate of the general formla III ##STR3## where R.sup.1 and R.sup.2 have the above meanings and R.sup.3 and R.sup.4 are each alkyl of 1 to 6 carbon atoms or aryl, and R.sup.4 may furthermore be hydrogen, in the presence of a catalyst at elevated temperatures, by a process in which the reaction is carried out in the presence of an alkali metal halide, of an ammonium halide, preferably a quaternary ammonium halide, of a phosphonium halide, of an alkali metal phosphate or of an alkali metal carbonate at from 20.degree. to 200.degree. C. and under from 1 to 50 bar.
    Type: Grant
    Filed: May 8, 1987
    Date of Patent: May 16, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Eckhardt, Walter Gramlich, Walter Best, Klaus Halbritter
  • Patent number: 4827001
    Abstract: Disclosed is the hydrogenation of maleic acid in the presence of a solid iron-containing ruthenium catalyst containing the elements and the ratios indicated by the empirical formula,RuFe.sub.a M.sub.b O.sub.xwhereM is one or more of Pd and Rh,a is 0.1-5,b is zero-3, andx is a number sufficient to satisfy the valency requirements of the cations present in the catalyst,said process being effected by contacting in a reaction zone an excess of hydrogen with an aqueous solution of maleic acid in admixture with said catalyst.
    Type: Grant
    Filed: November 2, 1987
    Date of Patent: May 2, 1989
    Assignee: The Standard Oil Company
    Inventors: Thomas G. Attig, Anne M. Graham
  • Patent number: 4782167
    Abstract: A process is disclosed for preparing butyrolactones, butanediols, and mixtures thereof comprising hydrogenating a hydrogenatable precursor in the presence of an aqueous reaction medium and a catalyst comprising palladium or combinations thereof with rhenium and at least one support selected from the oxides of titanium, zirconium, and hafnium.
    Type: Grant
    Filed: January 23, 1987
    Date of Patent: November 1, 1988
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Velliyur N. M. Rao
  • Patent number: 4772729
    Abstract: A process is disclosed for preparing 3-substituted tetrahydrofuran, 3- and 4-substituted butyrolactones and mixtures thereof comprising hydrogenating a hydrogenatable precursor in the presence of an aqueous reaction medium and a catalyst comprising palladium and rhenium and at least one support selected from the group consisting of titanium oxide, zirconium oxide, and carbon.
    Type: Grant
    Filed: January 23, 1987
    Date of Patent: September 20, 1988
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Velliyur N. M. Rao
  • Patent number: 4751334
    Abstract: Butane-1,4-diol is produced by vapor phase hydrogenolysis of an alkyl ester of a C.sub.4 dicarboxylic acid, e.g. diethyl maleate, over a reduced Cu-Cr or Cu-Zn mixed oxide catalyst. Two adiabatic hydrogenolysis zones are used. The mixture exiting the first of these zones is cooled (by, for example, 5.degree. C.) and the resulting cooled mixture is fed to the second zone in which is reequilibriates at a lower temperature to increase the butane-1,4-diol yield at the expense of gamma-butyrolactone. Typical reaction conditions include use of temperatures of 150.degree. C. to 200.degree. C., pressures of 25 to 70 bar, and a H.sub.2 :ester molar ratio of 100:1 to 800:1. When using a maleate ester it is often advantageous to hydrogenate this to the corresponding succinate ester in an upstream hydrogenation zone prior to entry to the first hyrogenolysis zone.
    Type: Grant
    Filed: July 21, 1986
    Date of Patent: June 14, 1988
    Assignee: Davy McKee (London) Limited
    Inventors: Keith Turner, Mohammad Sharif, Colin Rathmell, John W. Kippax, Anthony B. Carter, John Scarlett, Arthur J. Reason, Norman Harris
  • Patent number: 4740272
    Abstract: A method of producing substantially pure dialkyl maleate by separating monoalkyl maleate from dialkyl maleate in a short residence time distillation zone while minimizing reversion of the monoalkyl maleate to alkanol and maleic anhydride and without having to neutralize the monoalkyl maleate.
    Type: Grant
    Filed: March 31, 1987
    Date of Patent: April 26, 1988
    Assignee: Davy McKee (London) Limited
    Inventors: Ernesto Vera-Castaneda, Diane A. Montevideo, David J. Miller, John E. Logsdon, David R. Bryant
  • Patent number: 4673759
    Abstract: A process for the preparation of 2-alkyl cyclopent-2-enones having the formula: ##STR1## wherein R is as defined hereinafter. An .alpha.-olefin having the formula CH.sub.2 .dbd.CH--CH.sub.2 R is oxidized to the corresponding epoxide. The epoxide is reacted with an alkylating agent having the formula Na.sup.+ [CH(COOR").sub.2 ].sup.-, wherein R" is an ethyl, an isopropyl, or an isobutyl radical. An .alpha.-carbalkoxy-.gamma.-alkyl lactone is obtained, which, through saponification and decarboxylation, yields a .gamma.-alkyl lactone having the formula: ##STR2## which is reacted with a protic acid, thereby obtaining, by cyclization, the desired 2-alkylcyclopent-2-enone. The obtained products are intermediates for the production of pharmaceutical products and of drugs for veterinary use, in particular prostaglandin.
    Type: Grant
    Filed: March 3, 1986
    Date of Patent: June 16, 1987
    Assignee: Montedison S.p.A.
    Inventor: Enrico Dalcanale
  • Patent number: 4611069
    Abstract: A process for preparing gamma-caprolactone comprising isomerizing epsilon-caprolactone in an aqueous medium in the presence of catalytically effective amounts of hydriodic acid or hydrobromic acid wherein the catalyst is optionally promoted with a Group VIII metal. The temperature for the reaction is in the range of about 175.degree. C. to about 250.degree. C. and the ratio of water to epsilon-caprolactone is at least about 1:1.
    Type: Grant
    Filed: June 25, 1984
    Date of Patent: September 9, 1986
    Assignee: National Distillers and Chemical Corporation
    Inventors: Jawad H. Murib, John H. Kahn
  • Patent number: 4584419
    Abstract: A process for the production of butane-1,4-diol comprises hydrogenating a di(C.sub.1 to C.sub.3 alkyl) ester of a C.sub.4 dicarboxylic acid, e.g. an ester of a but-2-en-1,4-dioic acid, such as diethyl maleate, in the vapor phase at a temperature of from about 150.degree. C. to about 240.degree. C. and at a pressure in the range of from about 25 bar to about 75 bar in the presence of a reduced copper chromite catalyst, and recovering resulting butane-1,4-diol containing reaction product. The catalyst contains, before reduction, from about 25 to about 45% by weight of copper and from about 20 to about 35% by weight of chromium and preferably has an internal surface area of at least about 30 sq. m. per gram. The process is preferably conducted in two or more reaction zones, which are preferably operated adiabatically, the feed temperature to the first zone being higher than that to at least one subsequent reaction zone.
    Type: Grant
    Filed: November 21, 1984
    Date of Patent: April 22, 1986
    Assignee: Davy McKee Ltd.
    Inventors: Mohammad Sharif, Keith Turner
  • Patent number: 4564689
    Abstract: In processes for reacting acetic acid with butadiene in solvent to prepare acetoxyhexenoic acid and .gamma.-vinyl-.gamma.-butyrolactone, involving electrolytic regeneration of a metal ion oxidant such as trivalent manganese, the product separation is facilitated by using low melting electrolyte salts and separating product from salts maintained in a molten state.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: January 14, 1986
    Assignee: Monsanto Company
    Inventors: James P. Coleman, Dudley E. McMackins
  • Patent number: 4560775
    Abstract: Butadiene and acetic acid are reacted with a metal salt oxidant in molten salt medium to form .gamma.-vinyl-.gamma.-butyrolactone. The process includes electrolytic regeneration of the oxidant and provides a simple reaction system which permits product recovery and reactant recycle without extensive solvent handling. A high surface area reactor can be employed.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: December 24, 1985
    Assignee: Monsanto Company
    Inventors: James P. Coleman, Richard C. Hallcher, Dudley E. McMackins, Charles R. Penquite, Steven R. Auvil
  • Patent number: 4550181
    Abstract: A process for preparing gamma-caprolactone comprising heating polycaprolactone in the presence of catalytically effective amounts of an acid comprised of hydrogen halides in a water solution to a temperature in the range of about 175.degree. C. to about 275.degree. C. and the ratio of water to polycaprolactone is in the range of about 1:1 to about 10:1.
    Type: Grant
    Filed: June 25, 1984
    Date of Patent: October 29, 1985
    Assignee: National Distillers and Chemical Corporation
    Inventors: Jawad H. Murib, John H. Kahn
  • Patent number: 4526990
    Abstract: In the process of preparing acetoxyhexenoic acids from butadiene, acetic acid and acetic anhydride, selectivity is improved by converting the acetoxyhexenoic acids to .gamma.-vinyl-.gamma.-butyrolactone before isolation. Copper and platinum are useful catalysts in the conversion.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: July 2, 1985
    Assignee: Monsanto Company
    Inventors: James P. Coleman, Richard C. Hallcher, Thomas E. Rogers, Dudley E. McMackins
  • 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: 4460787
    Abstract: The acid conversion of certain precursors, e.g. .gamma.-vinyl-.gamma.-butyrolactone, to sorbic acid is improved by presence of copper or silver ions along with the acid.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: July 17, 1984
    Assignee: Monsanto Company
    Inventors: James P. Coleman, Richard C. Hallcher
  • 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: 4380650
    Abstract: Acyloxyhexenoic acids are converted to .gamma.-vinyl-.gamma.-butyrolactone.
    Type: Grant
    Filed: January 2, 1981
    Date of Patent: April 19, 1983
    Assignee: Monsanto Company
    Inventors: James P. Coleman, Richard C. Hallcher, Dudley E. McMackins
  • Patent number: 4356317
    Abstract: Acyloxyhexenoic acids are produced by reaction of butadiene and acetic acid with metal salt oxidants in a process involving electrolytic regeneration of the metal oxidants during the reaction.
    Type: Grant
    Filed: January 2, 1981
    Date of Patent: October 26, 1982
    Assignee: Monsanto Company
    Inventors: James P. Coleman, Richard C. Hallcher, Dudley E. McMackins