Preparing By Hydrogenation Of Cyclic Anhydrides Patents (Class 549/325)
  • Patent number: 4968818
    Abstract: A catalytic hydrogenation process for converting maleic anhydride and/or succinic anhydride to gamma-butyrolactone, a novel selective catalyst for use in such process and a method of preparing the catalyst are provided. The process comprises contacting maleic anhydride and/or succinic anhydride with hydrogen in the presence of catalysts whereby the anhydride is converted to predominantly gamma-butyrolactone. The catalyst of the invention is comprised of transition metals, their oxides and mixtures thereof on a silica gel support having a high surface area and pore volume.
    Type: Grant
    Filed: August 3, 1989
    Date of Patent: November 6, 1990
    Assignee: Phillips Petroleum Company
    Inventors: Geir Bjornson, Joel J. Stark
  • 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: 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
  • Patent number: 4892955
    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: July 13, 1987
    Date of Patent: January 9, 1990
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Keisuke Wada, Yoshinori Hara, Koushi Sasaki
  • 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: 4668654
    Abstract: A process for preparing primarily gamma-butyrolactone comprises the step of contacting under suitable reaction conditions a succinic anhydride containing feed stream and hydrogen, in the presence of a catalyst composition comprising (a) substantially metallic nickel, (b) at least one oxide selected from oxides of cerium and zirconium, and (c) a silica-containing support. In another embodiment, the above described catalyst composition is provided.
    Type: Grant
    Filed: July 11, 1986
    Date of Patent: May 26, 1987
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4620016
    Abstract: A process for preparing primarily gamma-butyrolactone comprises the step of contacting under suitable reaction conditions a succinic anhydride containing feed stream with hydrogen gas, in the presence of a catalyst comprising metallic nickel and an aluminum phosphate containing support.
    Type: Grant
    Filed: May 16, 1985
    Date of Patent: October 28, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Charles A. Drake, Marvin M. Johnson
  • Patent number: 4620017
    Abstract: A process for preparing primarily gamma-butyrolactone comprises the step of contacting under suitable reaction conditions a succinic anhydride containing feed stream and hydrogen, in the presence of a catalyst composition comprising (a) substantially metallic nickel, (b) at least one oxide selected from oxides of cerium and zirconium, and (c) a silica-containing support. In another embodiment, the above described catalyst composition is provided.
    Type: Grant
    Filed: May 16, 1985
    Date of Patent: October 28, 1986
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4485246
    Abstract: The rate of selective hydrogenation of carboxylic acid anhydrides to esters or lactones in the presence of a ruthenium organophosphorous catalyst which contains or liberates a hydrogen halide during the hydrogenation, is improved by providing in the reaction medium prior to or during the hydrogenation a basic amino compound to remove the hydrogen halide.
    Type: Grant
    Filed: October 29, 1982
    Date of Patent: November 27, 1984
    Assignee: Sun Tech, Inc.
    Inventor: James E. Lyons
  • Patent number: 4485245
    Abstract: Process for selective homogeneous catalytic hydrogenation of carboxylic acid anhydrides to ester or lactones at an improved rate and to obtain improved yields wherein the catalyst is a ruthenium trichlorostannate complex of the formula: ##STR1## wherein X is hydrogen, chlorine, bromine, iodine or lower alkyl; m is the integer 1 or 2; n is an integer of from 0 to 3 but when n is 2 or 3, X may be the same or different; M is P, As or Sb; R.sup.6, R.sup.7 and R.sup.8 independently are lower alkyl, cycloalkyl, aryl, benzyl or a bidentate legand; x is an integer of from 1 to 4 but when x is 2 or more, M may be the same or different; L is a neutral ligand, olefin, CO or (R.sup.9).sub.2 CO wherein R.sup.9 is lower alkyl; y is an integer of from 0 to 3 but when y is 2 or 3, L may be the same or different; and the sum of x and y is at least 2.
    Type: Grant
    Filed: October 29, 1982
    Date of Patent: November 27, 1984
    Assignee: Sun Tech, Inc.
    Inventors: Chao-Yang Hsu, James E. Lyons
  • Patent number: 4361563
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen; trifluoromethyl; alkyl of 1 to 11 carbon atoms; cycloalkyl of 3 to 7 carbon atoms; hydroxyl; alkoxy of 1 to 6 carbon atoms; mercapto; (alkyl of 1 to 6 carbon atoms)-mercapto; phenyl-(alkyl of 1 to 3 carbon atoms); phenyl; or mono-, di- or tri-substituted phenyl, where the substituents, which may be identical to or different from each other, are each halogen, alkyl of 1 to 4 carbon atoms, (alkyl of 1 to 6 carbon atoms)-sulfinyl, hydroxyl, alkoxy of 1 to 6 carbon atoms, mercapto or (alkyl of 1 to 6 carbon atoms)-mercapto;R.sub.2 is hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms or phenyl-(alkyl of 1 to 3 carbon atoms); andR.sub.3 is alkyl of 1 to 6 carbon atoms; optically active antipodes thereof; and non-toxic, pharmaceutically acceptable acid addition salts of said compounds or of said optically active antiposed. The compounds are useful as cardiotonics and antithrombotics.
    Type: Grant
    Filed: May 1, 1981
    Date of Patent: November 30, 1982
    Assignee: Dr. Karl Thomae Gesellschaft mit Beschrankter Haftung
    Inventors: Volkhard Austel, Joachim Heider, Wolfgang Eberlein, Willi Diederen, Walter Haarmann