The Organic Compound Contains A Carbonyl (e.g., Ketene, Etc.) Patents (Class 558/341)
  • Publication number: 20100029976
    Abstract: The invention relates to a process for preparing tetraethylenepentamine (TEPA) by hydrogenation of diethylenetriaminediacetonitrile (DETDN) over a catalyst. If appropriate, DETDN can also be present as a constituent of an amino nitrile mixture which additionally comprises diethylenetriaminemonoacetonitrile (DETMN).
    Type: Application
    Filed: February 27, 2008
    Publication date: February 4, 2010
    Applicant: BASF SE
    Inventors: Kirsten Dahmen, Alfred Oftring, Randolf Hugo, Thilo Hahn, Katrin Baumann, Johann-Peter Melder
  • Patent number: 7652165
    Abstract: The present invention relates to a process for preparing 3-cyano-3,5,5-trimethylcyclohexanone (isophoronenitrile) by reacting isophorone with hydrogen cyanide in the presence of a base as a catalyst to obtain a crude isophoronenitrile product, and subsequently distilling the crude isophoronenitrile product, with the addition before distillation of at least one specific sulfonic acid or specific carboxylic acid. In addition, the present invention relates to the use of a specific sulfonic acid or of a specific carboxylic acid as a neutralizing agent before distillation of a crude isophoronenitrile product which has been obtained by reacting isophorone with hydrogen cyanide in the presence of a base as a catalyst, in order to avoid precipitates in the neutralization of the base used as a catalyst with an acid.
    Type: Grant
    Filed: December 16, 2003
    Date of Patent: January 26, 2010
    Assignee: BASF Aktiengesellschaft
    Inventors: Alfred Oftring, Gerold Braun
  • Publication number: 20040171862
    Abstract: The invention relates to a method for producing optically active cyanohydrins and the corresponding &agr;-hydroxy-carboxylic acids, starting from an aldehyde, hydrogen cyanide and an optically active vanadyl-salen catalyst, whereby the reaction mixture is reacted at a temperature of between 0 and 60° C. Between 0.8 and 10 equivalents of hydrogen cyanide and between 0.0001 and 0.05 equivalents of vanadyl-salen catalyst in relation to the aldehyde, (concentration of between 0.5 and 4 mol/litre solvent), are preferably used. After said reaction the optically active cyanohydrin or after an acid hydrolysis the corresponding optically active &agr;-hydroxycarboxylic acid can be isolated with a surplus of enantiomers. The vanadium catalyst used in the invention contains a salen ligand, whereby the ratio salen ligand: vanadium (IV) in the catalyst ranges between 1.4:1 and 10:1.
    Type: Application
    Filed: December 22, 2003
    Publication date: September 2, 2004
    Inventors: Bettin Kirschbaum, Rainer Fell
  • Patent number: 6111128
    Abstract: In the presence of a metal catalyst such as a samarium compound, an enol ester compound shown by the formula (1) is reacted with a carbonyl compound shown by the formula (3) and a cyanogenation agent to produce an .alpha.-cyanohydrin ester shown by the formula (4): ##STR1## wherein R.sup.1, R.sup.7, and R.sup.8 are the same or different from each other, each representing a non-reactive atom or a non-reactive organic group; R.sup.2, R.sup.3, and R.sup.4 are the same or different from each other, each representing a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.By hydrolyzing the obtained compound, the corresponding .alpha.-hydroxy acid or a salt thereof can be obtained. According to the above processes, an .alpha.-cyanohydrin ester and an .alpha.-hydroxy acid can be obtained in high yields.
    Type: Grant
    Filed: December 17, 1998
    Date of Patent: August 29, 2000
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano
  • Patent number: 6022988
    Abstract: In a process for preparing 3-cyano-3,5,5-trimethylcyclohexanone by reacting isophorone with hydrogen cyanide at from 80 to 220.degree. C. in the presence of a catalyst, the reaction is carried out in the presence of the betaine 1,3-dimethylimidazolium-4-carboxylate.
    Type: Grant
    Filed: August 11, 1999
    Date of Patent: February 8, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Jakob Fischer, Wolfgang Siegel, Volker Bomm, Martin Fischer, Klaus Mundinger
  • Patent number: 5756803
    Abstract: A process for the condensation of an aldehyde with hydrogen cyanide in the presence of a buffer is disclosed. The buffer advantageously allows the condensation reaction to occur at a pH equal to or above 4.0 and in the absence of amines.
    Type: Grant
    Filed: April 24, 1996
    Date of Patent: May 26, 1998
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Claude Casse, Frederic Kress, Philippe Morel
  • Patent number: 5516928
    Abstract: A process for the preparation of 3-cyano-3,5,5-trimethylcyclohexanone by the reaction of isophorone with hydrogen cyanide in the presence of quaternary ammonium catalysts at temperatures ranging from 80.degree. to 180.degree. C. and pressures ranging from 0.5 to 20 bar, in which the ammonium catalysts used are salts of the general formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 denote C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.8 cycloalkyl, aryl, C.sub.7 -C.sub.18 aralkyl or C.sub.2 -C.sub.18 hydroxyalkyl andX denotes HCO.sub.3 or ##STR2## with the proviso that R.sup.4 stands for C.sub.1 -C.sub.
    Type: Grant
    Filed: February 28, 1995
    Date of Patent: May 14, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Mundinger, Gerhard Laqua, Tom Witzel, Franz Merger
  • Patent number: 5463103
    Abstract: The object of the present invention is to provide a process for producing 1,4-dicyano-2-butene in a high yield and in an industrially advantageous way.The present invention relates to a process for producing 1,4-dicyano-2-butene which comprises reacting a butene derivative represented by the formula [1]R.sub.1 --CH.sub.2 --CH.dbd.CH--CH.sub.2 --R.sub.2 [1]or the formula [2]R.sub.3 --CH.sub.2 --CHR.sub.4 --CH.dbd.CH.sub.2 [2]wherein each of R.sub.1 and R.sub.3 represents a hydroxy group, lower acyloxy group, lower alkoxy group or cyano group; and each of R.sub.2 and R.sub.4 represents a hydroxy group, lower acyloxy group or lower alkoxy group, with hydrogen cyanide in the presence of a catalyst comprising a product prepared from a cuprous halide, a non-aromatic amine hydrohalide and at least one member selected from the group consisting of Lewis acids and basic compounds.
    Type: Grant
    Filed: February 24, 1994
    Date of Patent: October 31, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shinji Nishii, Shigeo Wake, Takeshi Ogawa
  • Patent number: 5254711
    Abstract: Abstract of the disclosure: A process for the continuous preparation of 3-cyano-3,5,5-trimethylcyclohexanone by base-catalyzed reaction of isophorone and hydrogen cyanide, comprises carrying out the reaction in two separate reaction zonesa) with essentially complete back-mixing and subsequentlyb) essentially without back-mixing.
    Type: Grant
    Filed: February 5, 1993
    Date of Patent: October 19, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans J. Pander, Hardo Siegel, Otto Woerz
  • Patent number: 5235089
    Abstract: A process for the preparation of isophorone nitrile utilizing solutions of lithium hydroxide or lithium cyanide, solid LiOH or solid LiOH.cndot.H.sub.2 O as a catalyst. The reaction is carried out under precisely controlled temperature conditions and cyanide feed rate profiles to maintain a reasonably constant concentration of non-reacted cyanide, thereby minimizing the formation of undesirable diisophorone, its nitrile derivative(s) and HCN polymers. A polyacidic acid can be used to acidify the batch, followed by filtration to remove the precipitated lithium salt of the acid, and vacuum distillation to remove liberated HCN and excess isophorone. The resulting isophorone nitrile is obtained in high yield and with low impurity content.
    Type: Grant
    Filed: February 27, 1992
    Date of Patent: August 10, 1993
    Assignee: Hampshire Chemical Corp.
    Inventors: Richard P. Woodbury, Jon C. Thunberg, Steven P. VanKouwenberg, Walter B. Begonis
  • Patent number: 5183915
    Abstract: The production of 3-cyano-3,5,5-trialkylcyclohexanone from the reaction of 3,5,5-trialkylcyclohexenone and hydrocyanide at elevated temperature and in the presence of a catalytic amount of an onium cyanide, is disclosed herein.
    Type: Grant
    Filed: March 5, 1992
    Date of Patent: February 2, 1993
    Assignee: Elf Atochem North America, Inc.
    Inventors: Christian Forguy, Frederick J. Goetz, Edward L. Graeber, Michael J. Lindstrom
  • Patent number: 5179221
    Abstract: A method for the production of 3-cyano-3,5,5-trimethyl cyclohexanone by the reaction of isophorone with hydrogen cyanide in the presence of a quaternary ammonium salt or quaternary phosphonium salt and a basic compound as a catalyst in the form dissolved or dispersed in water or in the absence of water, which method comprises effecting said reaction by using said quaternary ammonium salt or quaternary phosphonium salt in an amount in the range of from 0.001 to 0.1 mol per mol of isophorone and said basic compound and in an amount in the range of from 0.5 to 3.0 mols per mol of said quaternary ammonium salt or quaternary phosphonium salt and, when water is used, using water in an amount in the range of 0.1 to 25% by weight based on the amount of isophorone and introducing hydrogen cyanidehydrocyanic acid at a ratio in the range of from 0.6 to 1.0 mol per mol of isophorone at a temperature in the range of from 90.degree. to 140.degree. C.
    Type: Grant
    Filed: July 9, 1991
    Date of Patent: January 12, 1993
    Assignee: Nippon Chemicals Co., Ltd.
    Inventors: Hiroshi Takahoso, Norio Takahashi, Koji Midorikawa, Toshiyasu Sato
  • Patent number: 5142090
    Abstract: The present invention relates to a process for the preparation of 3-cyano-3,5,5'-trimethyl-1-cyclohexanone by means of the reaction of isophorone with an alkaline cyanide. The reaction is performed starting from isophorone and an equivalent amount of cyanide in a homogeneous water/organic solvent solution at a temperature comprised between 20.degree. C. and the reflux temperature, maintaining a pH between 14 and 8 by means of a gradual addition of an inorganic acid during the reaction.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: August 25, 1992
    Assignee: Caffaro S.p.A.
    Inventors: Enrico Pontoglio, Sandro Parodi
  • Patent number: 5091554
    Abstract: Hydrogen cyanide is added to isophorone for the preparation of 1,3,3-trimethyl-5-oxo-carbonitrile in the presence of lithium hydroxide in an amount in a range of 0.005 to 5 mole % at 100.degree. to 160.degree. C. The yield is higher and the space-time yield is better than was possible when using other alkaline acting alkali compounds.
    Type: Grant
    Filed: December 5, 1990
    Date of Patent: February 25, 1992
    Assignee: Degussa AG
    Inventors: Klaus Huthmacher, Hermann Schmitt
  • Patent number: 5087723
    Abstract: An improved process for the nickel-catalyzed hydrocyanation of alkyl 2-alkenoates is disclosed.
    Type: Grant
    Filed: May 1, 1990
    Date of Patent: February 11, 1992
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Ronald J. McKinney
  • Patent number: 5011968
    Abstract: A process for preparing isophorone nitrile is disclosed, whereby isophorone is reacted with hydrogen cyanide in the presence of a quaternary ammonium catalyst. Remaining catalyst is removed by thermal destruction and nitrogen sparging. Residual cyanide is removed by acidification and nitrogen sparging.
    Type: Grant
    Filed: February 6, 1990
    Date of Patent: April 30, 1991
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Jon C. Thunberg, Walter B. Begonis
  • Patent number: 4810815
    Abstract: Process of polyene hydrocyanation, in particular diene hydrocyanation, wherein a promotionally effective amount of any acid with a pK.sub.a above about 2 and below and 14, preferably aryl alcohols such as phenol and cresols, is used.
    Type: Grant
    Filed: November 4, 1987
    Date of Patent: March 7, 1989
    Assignee: E. I. Du Pont De Nemours and Company
    Inventor: Henry E. Bryndza
  • Patent number: 4788318
    Abstract: A process for the production of the bicyclic compound 4,4,8,8,10-pentamethyl-10-cyano-bicyclo[4.4.0]-dec-1,6-en-2-one which comprises the steps of (a) reacting a ketone fraction comprising ##STR1## or mixtures thereof, (b) by adding HCN to the ketone fraction the presence of a base, at a temperature of 50.degree.-200.degree. C. to obtain an addition product comprising the bicyclic compound, and(c) isolating the addition product.
    Type: Grant
    Filed: August 25, 1987
    Date of Patent: November 29, 1988
    Assignee: Huls Aktiengesellschaft
    Inventors: Wilfried Buschken, Klaus Rindtorff
  • Patent number: 4766141
    Abstract: Spiro-succinimides are disclosed which are useful as aldose reductase inhibitors and as therapeutic agents for the treatment of complications arising from diabetes. Pharmaceutical compositions containing the spiro- compounds and a method of treating diabetic complications are also disclosed.
    Type: Grant
    Filed: October 14, 1987
    Date of Patent: August 23, 1988
    Assignee: Pfizer Inc.
    Inventor: Christopher A. Lipinski
  • Patent number: 4678791
    Abstract: 6-Phenyl-1,2,3,4,4a,5,6,10b-octahydrobenz(h)isoquinolines having anti-depressant activity and methods for their preparation.
    Type: Grant
    Filed: May 7, 1985
    Date of Patent: July 7, 1987
    Assignee: Pennwalt Corporation
    Inventors: James J. Napier, Ronald C. Griffith
  • Patent number: 4590012
    Abstract: An alpha-arylacrylonitrile is prepared by reacting an aryl ketone having a removable hydrogen alpha to the carbonyl group with an alkali metal cyanide and a Lewis acid other than aluminum chloride, preferably in the presence of a solvent. In a preferred embodiment, the aryl ketone is a tetralone, the cyanide is sodium cyanide, the Lewis acid is boron trifluoride, and the product is a 1-cyano-3,4-dihydronaphthalene.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: May 20, 1986
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • Patent number: 4590010
    Abstract: 6-Alkoxy-5-trifluoromethyl-1-naphthoic acids are prepared by (1) cyanating a 6-alkoxytetralone so as to form a 6-alkoxy-1-cyano-3,4-dihydronaphthalene, (2) converting the 6-alkoxy-1-cyano-3,4-dihydronaphthalene to a naphthoic acid precursor selected from a 6-alkoxy-1-cyanonaphthalene and a hydrocarbyl 6-alkoxy-1-naphthoate, (3) halogenating the naphthoic acid precursor to the corresponding 5-halo derivative, (4) trifluoromethylating the 5-halo derivative to replace the 5-halo substituent with a 5-trifluoromethyl group, and (5) hydrolyzing the resultant product to a 6-alkoxy-5-trifluoromethyl-1-naphthoic acid. In a preferred embodiment of the invention, the process is conducted so as to prepare 6-methoxy-5-trifluoromethyl-1-naphthoic acid, which, like the other products, is known to be useful as a pharmaceutical intermediate.
    Type: Grant
    Filed: April 18, 1985
    Date of Patent: May 20, 1986
    Assignee: Ethyl Corporation
    Inventors: Venkataraman Ramachandran, Robert I. Davidson, John R. Maloney
  • Patent number: 4590013
    Abstract: An alpha-arylacrylonitrile is prepared by reacting an aryl ketone having a removable hydrogen alpha to the carbonyl group with a cyanide ion source which is free of radicals that would stabilize a cyanohydrin corresponding to the aryl ketone and with a Lewis acid, preferably in the presence of a solvent. In a preferred embodiment, the aryl ketone is a tetralone, the cyanide ion source is hydrogen cyanide, the Lewis acid is aluminum chloride, and the product is a 1-cyano-3,4-dihydronaphthalene.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: May 20, 1986
    Assignee: Ethyl Corporation
    Inventors: John R. Maloney, Venkataraman Ramachandran
  • Patent number: 4581176
    Abstract: An alpha-arylacrylonitrile is prepared by reacting an aryl ketone having a removable hydrogen alpha to the carbonyl group with a cyanide ion source which is free of radicals that would stabilize a cyanohydrin corresponding to the aryl ketone and with a Lewis acid in the presence of an activating amount of water and/or HCl and preferably in the presence of a solvent. In a preferred embodiment, the aryl ketone is a tetralone, the cyanide ion source is sodium cyanide, the Lewis acid is aluminum chloride, and the product is a 1-cyano-3,4-dihydronaphthalene.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: April 8, 1986
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson