Processes Of Attaching Cyano To Carbon By Reaction Of An Inorganic Cyanide With An Organic Compound (e.g., Using Hcn, Cyanogen, Metal Cyanide, Ammonium Cyanide, Cyanogen Chloride, Etc.) Patents (Class 558/332)
  • Patent number: 11097254
    Abstract: A novel mixed oxide material is disclosed which contains molybdenum, vanadium, tellurium and niobium and the use of the molybdenum mixed oxide material as catalyst for the oxidative dehydrogenation of ethane to ethene or the oxidation of propane to acrylic acid and a process for producing the mixed oxide material.
    Type: Grant
    Filed: January 26, 2018
    Date of Patent: August 24, 2021
    Assignee: CLARIANT PRODUKTE (DEUTSCHLAND) GMBH
    Inventors: Gerhard Mestl, Klaus Wanninger, Daniel Melzer, Maria Cruz Sanchez-Sanchez, Julia Tseglakova, Johannes Lercher
  • Patent number: 9260368
    Abstract: A multistage process for the preparation of methacrylic acid and esters thereof via the hydrolysis of ACH, cracking the hydrolysis products, and converting the cracked products to the desired acid or ester, wherein the average temperature in the first hydrolysis reactor is from 55 C to 70 C.
    Type: Grant
    Filed: September 9, 2013
    Date of Patent: February 16, 2016
    Assignee: Rohm and Haas Company
    Inventors: Andrew M. Lemonds, Minh N. Ngo, Muhunthan Sathiosatham, Donald Lee Zolotorofe
  • Patent number: 9073822
    Abstract: The production of compounds comprising nitrile functions and of cyclic imide compounds is described. Further described, is the production of compounds comprising nitrile functions from compounds comprising carboxylic functions, optionally of natural and renewable origin, and from a mixture N of dinitriles comprising 2-methylglutaronitrile (MGN), 2-ethylsuccinonitrile (ESN) and adiponitrile (AdN).
    Type: Grant
    Filed: May 17, 2011
    Date of Patent: July 7, 2015
    Assignee: RHODIA OPERATIONS
    Inventors: Roland Jacquot, Philippe Marion
  • Patent number: 8697902
    Abstract: A process for the hydrocyanation of a hydrocarbon-based compound having at least one site of ethylenic unsaturation into a nitrile compound includes reaction thereof, in a liquid medium, with hydrogen cyanide in the presence of a catalyst containing a metal element selected from among the transition metals and an organophosphorus ligand, wherein the organophosphorus ligand is a compound of formula (I): The subject process is particularly useful for the synthesis of adiponitrile from butadiene.
    Type: Grant
    Filed: June 5, 2009
    Date of Patent: April 15, 2014
    Assignee: Rhodia Operations
    Inventor: Sergio Mastroianni
  • Patent number: 7777068
    Abstract: A system comprising a) Ni(0) b) from 4 to 10 mol per mol of Ni(0) in a) of a compound (I) of the formula P(X1R1)(X2R2)(X3R3)??(I) where X1, X2, X3 are each, independently of one another, oxygen or a single bond, R1, R2, R3 are, independently of one another, identical or different organic radicals and c) from 1 to 4 mol per mol of Ni(0) in a) of a compound (II) of the formula where X11, X12, X13 X21, X22, X23 are each, independently of one another, oxygen or a single bond, R11, R12 are identical or different, individual or bridged organic radicals, R21, R22 are identical or different, individual or bridged organic radicals and Y is a bridging group is suitable as catalyst for preparing mixtures of monoolefinic C5 mononitriles having nonconjugated C?C and C?N bonds by hydrocyanation of a 1,3-butadiene-containing hydrocarbon mixture and for preparing a dinitrile by hydrocyanation of a mixture of monoolefinic C5 mononitriles having nonconjugated C?C and C?N bonds.
    Type: Grant
    Filed: September 25, 2007
    Date of Patent: August 17, 2010
    Assignee: BASF SE
    Inventors: Michael Bartsch, Robert Baumann, Dagmar Pascale Kunsmann-Keitel, Gerd Haderlein, Tim Jungkamp, Marco Altmayer, Wolfgang Siegel
  • Patent number: 7709673
    Abstract: The invention provides a continuous process for the production of 3-pentenenitrile comprising: (a) contacting, in a reaction zone, a hydrogen cyanide-containing feed, a butadiene-containing feed, and a catalyst precursor composition, wherein the catalyst precursor composition comprises a zero-valent nickel and at least one bidentate phosphite ligand selected from a member of the group represented by Structures I and II, in which all like reference characters have the same meaning, except as further explicitly limited: wherein R1 and R5 are independently selected from the group consisting of C1 to C5 hydrocarbyl, and R2, R3, R4, R6, R7 and R8 are independently selected from the group consisting of H and C1 to C4 hydrocarbyl; and (b) maintaining a residence time in the reaction zone sufficient to convert about 95% or more of the hydrogen cyanide and to produce a reaction mixture comprising 3-pentenenitrile and 2-methyl-3-butenenitrile, wherein the 2-methyl-3-butenenitrile concentration is maintain
    Type: Grant
    Filed: July 12, 2007
    Date of Patent: May 4, 2010
    Assignee: Invista North America S.A R.L.
    Inventors: Thomas Foo, Sigridur S. Kristjansdottir, Ronald J. McKinney, Ron Ozer
  • Patent number: 7709674
    Abstract: A hydrocyanation process produces adiponitrile and other dinitriles having six carbon atoms. The process involves forming a reaction mixture in the presence of at least one Lewis acid. The reaction mixture includes ethylenically unsaturated nitrites having five carbon atoms, hydrogen cyanide, and a catalyst precursor compositions. The reaction mixture is continuously fed while controlling the overall feed molar ratio of 2-pentenenitriles to all unsaturated nitriles and the overall feed molar ratio of hydrogen cyanide to all unsaturated nitrites. In the reaction product mixture, including adiponitrile, the ratio of the concentration of 2-pentenenitriles to the concentration of 3-pentenenitriles from about 0.2/1 to about 10/1. Included in the catalyst precursor composition is a zero-valent nickel and at least one multidentate phosphorus-containing ligand.
    Type: Grant
    Filed: July 12, 2007
    Date of Patent: May 4, 2010
    Assignee: Invista North America S.A R.L
    Inventors: Thomas Foo, James Michael Garner, Ron Ozer, Paul S. Pearlman
  • Publication number: 20090299023
    Abstract: The present invention relates in general terms to a process for preparing acetone cyanohydrin, comprising as steps: A. contacting acetone and hydrocyanic acid in a reactor to give a reaction mixture, the reaction mixture being circulated, to obtain acetone cyanohydrin; B. cooling at least some of the reaction mixture by flowing it through a cooling region of a cooler, the cooler including one cooling element or at least two cooling elements; C.
    Type: Application
    Filed: August 31, 2007
    Publication date: December 3, 2009
    Applicant: EVONIK ROEHM GMBH
    Inventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
  • Patent number: 7612223
    Abstract: The present invention relates to a process for the hydrocyanation of unsaturated compounds to unsaturated mononitrile compounds or to dinitrile compounds; It relates more particularly to a process for the manufacture of dinitriles by double hydrocyanation of diolefins, such as butadiene, comprising a recovery and separation of the catalytic system. The process for the manufacture of dinitriles of the invention by hydrocyanation of unsaturated compounds, comprising at least one stage of hydrocyanation in the presence of a catalytic system comprising an organometallic complex formed by one or more monodentate organophosphite ligands and one or more bidentate organophosphorus ligands and optionally a promoter of Lewis acid type, comprises at least one stage of separation by distillation of a reactant used in the process or of a compound formed by the reaction from a medium comprising the said catalytic system.
    Type: Grant
    Filed: May 7, 2004
    Date of Patent: November 3, 2009
    Assignee: Invista North America S.A R.L.
    Inventors: Cécile Rosier, Philippe Leconte, Damien Bourgeois
  • Patent number: 7541486
    Abstract: A process is described for preparing 3-pentenenitrile, characterized by the following process steps: (a) reacting 1,3-butadiene with hydrogen cyanide over at least one catalyst to obtain a stream 1 which comprises 3-pentenenitrile, 2-methyl-3-butenenitrile, the at least one catalyst and 1,3-butadiene, (b) distilling stream 1 in a column to obtain a high-1,3-butadiene stream 2 as the top product and a low-1,3-butadiene stream 3 as the bottom product which comprises 3-pentenenitrile, the at least one catalyst and 2-methyl-3-butenenitrile, (c) distilling stream 3 in a column to obtain a stream 4 as the top product which comprises 1,3-butadiene, a stream 5 which comprises 3-pentenenitrile and 2-methyl-3-butenenitrile at a side draw of the column, and a stream 6 as the bottom product which comprises the at least one catalyst, (d) distilling stream 5 to obtain a stream 7 as the top product which comprises 2-methyl-3-butenenitrile, and a stream 8 as the bottom product which comprises 3-pentenenitrile.
    Type: Grant
    Filed: January 27, 2005
    Date of Patent: June 2, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Jens Scheidel, Tim Jungkamp, Michael Bartsch, Gerd Haderlein, Robert Baumann, Hermann Luyken
  • Patent number: 7531682
    Abstract: The present invention concerns a process for hydrocyanating ethylenically unsaturated organic compounds to compounds containing at least one nitrile function. It relates more particularly to the hydrocyanation of diolefins such as butadiene or of substituted olefins such as alkenenitriles, for instance pentenenitriles. According to the process of the invention the reaction is implemented in the presence of a metal complex catalyst comprising a transition metal such as nickel and an organic ligand.
    Type: Grant
    Filed: July 11, 2003
    Date of Patent: May 12, 2009
    Assignee: Rhodia Polyamide Intermediates
    Inventors: Jean-Christophe Galland, Blaise Didillon, Philippe Marion, Damien Bourgeois
  • Patent number: 7531698
    Abstract: Tetraphosphorous ligands are combined with transition metal salts to form catalysts for use in hydroformylation, isomerization-hydroformylation, hydrocarboxylation, hydrocyan-ation, isomerization-formylation, hydroaminomethylation and similar related reactions.
    Type: Grant
    Filed: December 15, 2006
    Date of Patent: May 12, 2009
    Assignee: The Penn State Research Foundation
    Inventors: Xumu Zhang, Yongjun Yan
  • Patent number: 7528275
    Abstract: A process is described for preparing adiponitrile by hydrocyanating 1,3-butadiene over a catalyst, by, in a first process step, hydrocyanating 1,3-butadiene to 3-pentenenitrile over at least one nickel(0) catalyst, and, in a second process step, hydrocyanating 3-pentenenitrile to adiponitrile over at least one nickel(0) catalyst with addition of at least one Lewis acid, wherein at least one of the at least one nickel(0) catalysts used in the particular process steps is transferred into the other process step.
    Type: Grant
    Filed: January 26, 2005
    Date of Patent: May 5, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Bartsch, Robert Baumann, Gerd Haderlein, Miguel Angel Flores, Tim Jungkamp, Hermann Luyken, Jens Scheidel, Wolfgang Siegel
  • Patent number: 7521575
    Abstract: The invention relates to phosphinite phosphites I of formula 1, 2, 3, 4, 5 or 6 and mixtures thereof, wherein R1, R2, R4 independently represent an alkyl or alkylene group with 1 to 8 carbon atoms, provided that at least one of the groups R1, R2, R4 is different from H; R5 to R22 independently represent H, an alkyl or alkylene group with 1 to 8 carbon atoms; R3 is H, methyl or ethyl; X is F, Cl or CF3, if n=1 or 2 and X is H, if n=0.
    Type: Grant
    Filed: October 28, 2004
    Date of Patent: April 21, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Bartsch, Robert Baumann, Gerd Haderlein, Miquel Angel Flores, Tim Jungkamp, Hermann Luyken, Jens Scheidel, Wolfgang Siegel
  • Patent number: 7504529
    Abstract: A process is described for removing hydrogen cyanide from mixtures comprising pentenenitrile, wherein the removal is effected by an azeotropic distillation of hydrogen cyanide with 1,3-butadiene.
    Type: Grant
    Filed: January 26, 2005
    Date of Patent: March 17, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Tim Jungkamp, Hans-Martin Polka, Robert Baumann, Michael Bartsch, Gerd Haderlein, Hermann Luyken, Jens Scheidel
  • Patent number: 7485741
    Abstract: The present invention relates to a process for hydrocyanating a hydrocarbon-based compound containing at least one ethylenic unsaturation by reaction in liquid medium with hydrogen cyanide in the presence of a catalyst comprising a metal element chosen from transition metals and an organophosphorus ligand, characterized in that the organophosphorus ligand is a monodentate organophosphorus compound. The present invention is in particular useful for the synthesis of adiponitrile from butadiene.
    Type: Grant
    Filed: November 25, 2003
    Date of Patent: February 3, 2009
    Assignee: Rhodia Polyamide Intermediates
    Inventors: Damien Bourgeois, Jean-Christophe Galland, Blaise Didillon, Philippe Marion
  • Patent number: 7470805
    Abstract: A process of hydrocyanation of diolefins such as butadiene is carried out in the presence of a catalytic system comprising a transition metal and mono- and pluri-dentate organophosphorus ligands. The reaction medium containing branched nitrites subsequently is isomerized in the absence of hydrogen cyanide.
    Type: Grant
    Filed: June 27, 2006
    Date of Patent: December 30, 2008
    Assignee: Rhodia Operations
    Inventors: Cécile Rosier, Philippe Marion, Damien Bourgeois
  • Publication number: 20080221351
    Abstract: A process is described for preparing adiponitrile by hydrocyanating 1,3-butadiene over a catalyst, by, in a first process step, hydrocyanating 1,3-butadiene to 3-pentenenitrile over at least one nickel(0) catalyst, and, in a second process step, hydrocyanating 3-pentenenitrile to adiponitrile over at least one nickel(0) catalyst with addition of at least one Lewis acid, wherein at least one of the at least one nickel(0) catalysts used in the particular process steps is transferred into the other process step.
    Type: Application
    Filed: January 26, 2005
    Publication date: September 11, 2008
    Applicant: BASF AKTIENGESELLSCHAFT
    Inventors: Michael Bartsch, Robert Baumann, Gerd Haderlein, Migeul Angel Flores, Tim Jungkamp, Hermann Luyken, Jens Scheidel, Wolfgang Siegel
  • Patent number: 7375052
    Abstract: The present invention relates to a process for producing a metal oxide catalyst which is suitable for production of acrylic acid or acrylonitrile in one stage by a catalytic oxidation reaction of propane in a high yield. The present invention is characterized by using a fine particle of metallic tellurium obtained by reducing a Te compound with a reductant as a raw material for producing an oxide catalyst including metal elements Mo—V—Nb—Te. The fine particle of metallic tellurium is preferably one containing primary particles having a particle size of not more than 4.0 ?m. By using a metal oxide obtained by the process of the present invention, acrylic acid can be produced from propane by a one-stage oxidation reaction in a higher yield not less than 40%.
    Type: Grant
    Filed: April 13, 2004
    Date of Patent: May 20, 2008
    Assignee: Toagosei Co., Ltd.
    Inventors: Xinlin Tu, Yuuichi Sumida, Mamoru Takahashi, Hiroshi Niizuma
  • Patent number: 7371884
    Abstract: The invention relates to a process for preparing succinonitrile by contacting acrylonitrile (ACN) with hydrocyanic acid (HCN) in a reactor in the presence of a tertiary amine. The invention also relates to the use of succinonitrile prepared according to the process of the invention, for preparing diaminobutane. Succinonitrile is prepared by contacting ACN with HCN in the presence of a tertiary amine and a compound chosen from the group consisting of water, aliphatic alcohols, aromatic alcohols, carboxylic acids and mixtures thereof.
    Type: Grant
    Filed: December 3, 2002
    Date of Patent: May 13, 2008
    Assignee: DSM IP Assets B.V.
    Inventors: Hendrik Oevering, Franciscus H. A. M. Vandenbooren, Olaf Poorter
  • Patent number: 7253298
    Abstract: The present invention concerns a process for hydrocyanating ethylenically unsaturated organic compounds to compounds containing at least one nitrile function. It relates more particularly to the hydrocyanation of diolefins such as butadiene or of substituted olefins such as alkenenitriles, for instance pentenenitriles. According to the process of the invention the reaction is implemented in the presence of a metal complex catalyst comprising a transition metal such as nickel and an organic ligand.
    Type: Grant
    Filed: June 24, 2005
    Date of Patent: August 7, 2007
    Assignee: Rhodia Polyamide Intermediates
    Inventors: Jean-Christophe Galland, Blaise Didillon, Philippe Marion, Damien Bourgeois
  • Patent number: 7189883
    Abstract: This invention relates to asymmetric hydroformylation processes in which a prochiral or chiral olefin is reacted with carbon monoxide and hydrogen in the presence of an optically active metal-ligand complex catalyst to produce an optically active aldehyde or a product derived from an optically active aldehyde.
    Type: Grant
    Filed: August 25, 2005
    Date of Patent: March 13, 2007
    Inventors: Clark Landis, Thomas P. Clark, Jerzy Klosin
  • Patent number: 7084293
    Abstract: The present invention relates to a process of hydrocyanation of ethylenically unsaturated organic compounds to compounds having at least one nitrile function, particularly the hydrocyanation of diolefins such as butadiene, or of substituted olefins such as alkene nitrites such as pentenenitriles; the subject hydrocyanation is carried out in the presence of a catalytic system comprising a metallic element and mono- and pluri-dentate organophosphorus ligands.
    Type: Grant
    Filed: January 30, 2003
    Date of Patent: August 1, 2006
    Assignee: Rhodia Polyamides Intermediates
    Inventors: Cécile Rosier, Philippe Marion, Damien Bourgeois
  • Patent number: 7002034
    Abstract: A process for preparing biphenyl-4-carbonitrile of the formula in which biphenyl is reacted with cyanogen chloride in the presence of anhydrous aluminum chloride.
    Type: Grant
    Filed: October 28, 2002
    Date of Patent: February 21, 2006
    Inventors: Johannes Bartek, Pascal Willa
  • Patent number: 6846945
    Abstract: Disclosed herein are processes for hydrocyanation and isomerization of olefins by using at least one multidentate phosphonite ligands, including organometallic phosphonite ligands with a Group VIII metal or Group VIII metal compound, and optionally, a Lewis acid promoter.
    Type: Grant
    Filed: June 4, 2003
    Date of Patent: January 25, 2005
    Assignee: Invista North America S.a.r.l.
    Inventors: Christian P. Lenges, Helen S. M. Lu, Joachim C. Ritter
  • Patent number: 6770770
    Abstract: Novel phosphites have the formula I P(O—R1)x(O—R2)y(O—R3)z(O—R4)p  I where R1: aromatic radical having a C1-C18-alkyl substituent in the o position relative to the oxygen atom which connects the phosphorus atom to the aromatic system, or having an aromatic substituent in the o position relative to the oxygen atom which connects the phosphorus atom to the aromatic system, or having an aromatic system fused on in the o position relative to the oxygen atom which connects the phosphorus atom to the aromatic system, R2: aromatic radical having a C1-C18-alkyl substituent in the m position relative to the oxygen atom which connects the phosphorus atom to the aromatic system, or having an aromatic substituent in the m position relative to the oxygen atom which connects the phosphorus atom to the aromatic system, or having an aromatic system fused on in the m position relative to the oxygen atom which connects the phosphorus atom to the aromatic system, where the aromatic radical
    Type: Grant
    Filed: April 25, 2002
    Date of Patent: August 3, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Robert Baumann, Jakob Fischer, Tim Jungkamp, Dagmar Pascale Kunsmann-Keitel, Wolfgang Siegel
  • Publication number: 20040059161
    Abstract: Disclosed is a process for reducing fluoride content in a process utilizing a fluorophosphite-containing transition metal catalyst.
    Type: Application
    Filed: September 16, 2002
    Publication date: March 25, 2004
    Inventors: Ginette Struck Tolleson, Thomas Allen Puckette
  • Publication number: 20030212288
    Abstract: Disclosed herein are processes for hydrocyanation and isomerization of olefins by using at least one multidentate phosphonite ligands, including organometallic phosphonite ligands with a Group VIII metal or Group VIII metal compound, and optionally, a Lewis acid promoter.
    Type: Application
    Filed: June 4, 2003
    Publication date: November 13, 2003
    Inventors: Christian P. Lenges, Helen S. M. Lu, Joachim C. Ritter
  • Patent number: 6624323
    Abstract: Herein is provided a process for preparing substituted cyclohexanoic acids of formula (I), where Ra is a carbon-containing group optionally linked by oxygen, sulfur or nitrogen to the phenyl ring and j is 1-5; and one of R and R* is hydrogen and the other is C(O)OH.
    Type: Grant
    Filed: March 14, 2002
    Date of Patent: September 23, 2003
    Assignee: SmithKline Beecham Corporation
    Inventor: Jose J. Conde
  • Patent number: 6610874
    Abstract: Processes for the efficient production of chiral amino nitrites are disclosed. Generally, the processes include the esterification of the alcohol of a amino protected alcohol followed by nucleophilic substitution of the ester with a cyano group. In an exemplary embodiment the chiral amino nitrile produced is (R)-3-aminopentanenitrile.
    Type: Grant
    Filed: September 28, 2001
    Date of Patent: August 26, 2003
    Assignee: PCBU Services, Inc.
    Inventors: David Robert Allen, Crystal A. Achenbach-McCarthy
  • Publication number: 20030125563
    Abstract: One aspect of the present invention relates to methods for the transition-metal-catalyzed asymmetric 1,4-addition of a nucleophile, e.g., hydride, to cyclic and acyclic enoates and enones. In certain embodiments of the methods of the present invention, the transition metal catalyst consists essentially of copper and an asymmetric bidentate bisphosphine ligand.
    Type: Application
    Filed: October 15, 2002
    Publication date: July 3, 2003
    Inventors: Stephen L. Buchwald, Daniel H. Appella, Yasunori Moritani, Ryo Shintani, Valdas Jurkauskas
  • Publication number: 20030088118
    Abstract: Disclosed is an oxide catalyst comprising an oxide represented by the formula Mo1VaNbbXcYdZeQfOn (wherein: X is at least one element selected from the group consisting of Te and Sb; Y is at least one element selected from the group consisting of Al and W; Z is at least one element selected from the group consisting of elements which individually form an oxide having a rutile structure and a Z oxide having a rutile structure is used as a source of Z for producing the catalyst; Q is at least one element selected from the group consisting of titanium, tin, germanium, lead, tantalum, ruthenium, rhenium, rhodium, iridium, platinum, chromium, manganese, technetium, osmium, iron, arsenic, cerium, cobalt, magnesium, nickel and zinc, and a Q compound not having a rutile structure is used as a source of Q for producing the catalyst; and a, b, c, d, e, f and n are, respectively, the atomic ratios of V, Nb, X, Y, Z, Q and O, relative to Mo).
    Type: Application
    Filed: August 30, 2002
    Publication date: May 8, 2003
    Inventors: Satoru Komada, Hidenori Hinago, Osamu Nagano, Mamoru Watanabe
  • Publication number: 20030065207
    Abstract: Processes for the efficient production of chiral amino nitrites are disclosed. Generally, the processes include the esterification of the alcohol of a amino protected alcohol followed by nucleophilic substitution of the ester with a cyano group. In an exemplary embodiment the chiral amino nitrile produced is (R)-3-aminopentanenitrile.
    Type: Application
    Filed: September 28, 2001
    Publication date: April 3, 2003
    Inventors: David Robert Allen, Crystal A. Achenbach-McCarthy
  • Publication number: 20010034457
    Abstract: A process for preparing compounds of the formula IIb 1
    Type: Application
    Filed: June 8, 2001
    Publication date: October 25, 2001
    Applicant: BASF AKTIENGESELLSCHAFT
    Inventors: Rainer Rahm, Thomas Greindl, Alfred Oftring, Guenter Oetter, Juergen Detering, Gerold Braun
  • Patent number: 6133432
    Abstract: A process for preparing a compound of the formula ##STR1## wherein R is C.sub.1 -C.sub.18 alkyl by reacting a compound of the formulaRO.sub.2 C--CH.sub.2 CN (II)with a cyanide salt and formaldehyde or source thereof. Compounds of formula (I) are useful intermediates to pesticidally active compounds.
    Type: Grant
    Filed: December 1, 1998
    Date of Patent: October 17, 2000
    Assignee: Rhone-Poulenc Agro
    Inventors: David William Hawkins, David Alan Roberts, John Harry Wilkinson, Jean-Louis Clavel
  • Patent number: 6120557
    Abstract: Use of compounds of the formula ##STR1## where the radicals R.sup.1, R.sup.2 and A are as defined in the description, as bleach activators in bleaching detergents and cleaners.
    Type: Grant
    Filed: October 6, 1999
    Date of Patent: September 19, 2000
    Assignee: Clariant GmbH
    Inventor: Bernd Nestler
  • Patent number: 6100419
    Abstract: In the presence of a metal catalyst such as a samarium compound, an oxime ester compound shown by the formula (1): ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 are the same or different from each other, and each represents a non-reactive atom or a non-reactive organic group; and R.sup.2 and R.sup.3, together with the adjacent carbon atom, may bond together to form a ringis reacted with a cyanogenation agent such as an .alpha.-cyanohydrin compound (e.g., acetone cyanohydrin)to form an .alpha.-aminonitrile derivative. By hydrolyzing the .alpha.-aminonitrile derivative, the corresponding .alpha.-amino acid or a salt thereof can be obtained. According to the above processes, an .alpha.-aminonitrile derivative and an .alpha.-amino acid can be obtained in high yields.
    Type: Grant
    Filed: December 17, 1998
    Date of Patent: August 8, 2000
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano
  • Patent number: 6075162
    Abstract: A method of producing methyl methacrylate comprises Step 1 of producing acetone cyanhydrin from hydrogen cyanide and acetone; Step 2 of producing .alpha.-hydroxyisobutyramide by hydrating acetone cyanhydrin; Step 3 of producing methyl .alpha.-hydroxyisobutyrate and ammonia by a reaction of .alpha.-hydroxyisobutyramide and methanol; Step 4 of producing methyl methacrylate by dehydrating methyl .alpha.-hydroxyisobutyrate; and Step 5 of producing hydrogen cyanide in vapor phase by reacting methanol and the ammonia obtained in Step 3 over a solid catalyst in the presence of molecular oxygen. By using methanol in the step 3, the conversion ratio of .alpha.-hydroxyisobutyramide into methyl .alpha.-hydroxyisobutyrate can be increased because the equilibrium of the reaction is easily sifted toward the product side by removing ammonia being produced from the reaction system.
    Type: Grant
    Filed: March 2, 1999
    Date of Patent: June 13, 2000
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventor: Koichi Kida
  • Patent number: 6007583
    Abstract: Use of compounds of the formula ##STR1## where the radicals R.sup.1, R.sup.2 and A are as defined in the description, as bleach activators in bleaching detergents and cleaners.
    Type: Grant
    Filed: October 19, 1998
    Date of Patent: December 28, 1999
    Assignee: Clariant GmbH
    Inventor: Bernd Nestler
  • Patent number: 5965766
    Abstract: Nucleophilic substitution reactions on halobenzenes or triflyl substituted benzenes are carried out in the presence of catalysts. In particular the present invention provides a process leading to optionally substituted hydroxybenzoic, alkanoyloxybenzoic, formyloxybenzoic and alkoxybenzoic acids and optionally substituted hydroxybenzonitriles and alkoxybenzonitriles from substituted 2,6-dihalobenzenes, 2-halo-6-triflylbenzene and 2,6-ditriflylbenzenes.
    Type: Grant
    Filed: February 2, 1998
    Date of Patent: October 12, 1999
    Assignee: Rohm and Haas Company
    Inventors: Joshua Anthony Chong, Fereydon Abdesaken, Charles Chao Wu
  • Patent number: 5324852
    Abstract: The present invention provides an optically active 4-substituted-2-hydroxybutanoate represented by the general formula: ##STR1## wherein X is Cl, Br, I or Cn, R is alkyl, and * shows an asymmetric carbon.The compounds which are useful as starting materials for medical agents, are obtained by a process comprising ring-opening optically active .alpha.-hydroxy-.gamma.-butyrolactone and esterifying the compound obtained.
    Type: Grant
    Filed: November 16, 1992
    Date of Patent: June 28, 1994
    Assignee: Chisso Corporation
    Inventors: Naoyuki Yoshida, Kazutoshi Miyazawa
  • Patent number: 5169973
    Abstract: Alpha-aminonitriles can be synthesized by the reaction, at ambient temperature without use of catalyst, of essentially stoichiometric amounts of amine, aldehyde (either monoaldehyde or dialdehyde) and trimethylsilyl cyanide.
    Type: Grant
    Filed: April 15, 1991
    Date of Patent: December 8, 1992
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventors: Harry W. Gibson, Jean-Pierre LeBlanc
  • Patent number: 4994596
    Abstract: 1-Cyano-1-(4-alkylphenyl)alkenes having utility as chemical intermediates, especially in the preparation of ibuprofen and related pharmaceuticals, are prepared by reacting an alkylbenzene with an alkali metal cyanide and an acid halide in the presence of aluminum chloride.
    Type: Grant
    Filed: January 29, 1990
    Date of Patent: February 19, 1991
    Assignee: Ethyl Corporation
    Inventor: Barbara C. Stahly
  • Patent number: 4990630
    Abstract: The present invention relates to a 2,3-diaminoacrylonitrile derivative or salts thereof, having the formula ##STR1## wherein R represents an alkyl group (which may be substituted by unsubstituted or substituted phenyl groups, halogen atoms, C.sub.1-6 alkoxycarbonyl groups, carboxy groups, C.sub.1-6 alkoxycarbonyl C.sub.1-6 alkylthio groups, hydroxy groups, mercapto groups, cycloalkyl groups or heterocyclic groups containing oxygen atoms); an alkenyl group; a cycloalkyl group; an aryl group (which may be substituted by halogen atoms, C.sub.1-6 alkyl groups, nitro-groups, unsubstituted or substituted phenyl or phenoxy groups or heterocyclic groups containing oxygen atoms or sulfur atoms).The 2,3-diaminoacrylonitrile derivative can be used as starting materials for the production of pharmaceutical and/or agricultural intermediates such as cyanoimidazoles, cyanopyrazines or other cyano-substituted heterocycles.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: February 5, 1991
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Katsunori Mikuma, Nobuhiro Umeda, Tomio Yagihara, Isami Hamamoto
  • Patent number: 4959467
    Abstract: Hydrogen cyanide addition to a monosaccharide results in a mixture of product cyanohydrins whose ratio can be changed by conducting the hydrogen cyanide addition in the presence of an agent which forms a complex with the monosaccharide. It is preferred to add the elements of hydrogen cyanide to a preformed complex of the monosaccharide. The product selectivity appears to be dependent upon the concentration of the complexing agent up to about one molar proportion of the latter relative to the monosaccharide with the selectivity being invariant thereafter.
    Type: Grant
    Filed: February 16, 1988
    Date of Patent: September 25, 1990
    Assignee: Allied-Signal Inc.
    Inventor: Blaise J. Arena
  • Patent number: 4916251
    Abstract: A method for cyanoisoalkylating phenols or other hydroxy-substituted aryl compounds, which may have up to two substitutents ortho or para to the hydroxy moiety, comprising reacting a molar excess of phenol or aryl compound with a ketone in the presence of cyanide ion and hydroxide ion at an elevated temperature.Compounds, such as 4-(1-cyano-1-methylethyl)phenol, produced via this method are useful as chemical intermediates in the preparation of polyurethanes, epoxy resins and pharmaceutical and agricultural products.
    Type: Grant
    Filed: January 2, 1987
    Date of Patent: April 10, 1990
    Assignee: The Dow Chemical Company
    Inventor: Ted A. Morgan
  • Patent number: 4855476
    Abstract: The present invention relates to novel 5-fluoro- and 8-fluoro-trimetoquinol compounds of the general formula I wherein X.sub.1 =F, X.sub.2 =H or X.sub.1 =H, X.sub.2 =F ##STR1## The present invention also relates to a process for making the 5-fluoro- and 8-fluoro-trimetoquinol compounds by condensation of an appropriately substituted phenethylamine to afford an appropriately substituted phenlethylacetamide compound. The amides are cyclized to give appropriately substituted intermediate dihydroisoquinolines. Without isolation, the dihydroisoquinolines are reduced to give appropriately substituted tetrahydroisoquinolines. The hydrochloride salts of tetrahydroisoquinolines are prepared and subjected to hydrogenolysis, to give the fluorine substituted trimetoquinol compounds of the present invention.
    Type: Grant
    Filed: March 14, 1988
    Date of Patent: August 8, 1989
    Assignee: Ohio State University Research Foundation
    Inventors: Duane D. Miller, Dennis R. Feller, Michael T. Clark, Adeboye Adejare, Karl J. Romstedt, Gamal Shams
  • Patent number: 4824987
    Abstract: A method of preparing m-trifluoromethylphenyl acetonitrile of the formula ##STR1## in which m-trifluoromethyl toluene is reacted with cyanogen chloride in the gas phase at 600.degree. to 750.degree. C.
    Type: Grant
    Filed: May 23, 1988
    Date of Patent: April 25, 1989
    Assignee: Degussa Aktiengesellschaft
    Inventors: Axel Kleemann, Herbert Klenk, Klaus Huthmacher, Dieter Most
  • Patent number: 4806673
    Abstract: A process for preparing cyanoalkyphenols comprising contacting a bisphenol with cyanide ion at elevated temperatures under reaction conditions sufficient to produce the desired cyanoalkylphenol.Compounds, e.g. 4-(1-cyano-1-methylethyl)phenol, produced via this method are useful as chemical intermediates in the preparation of polyurethanes, epoxy resins and pharmaceutical and agricultural products.
    Type: Grant
    Filed: December 10, 1986
    Date of Patent: February 21, 1989
    Assignee: The Dow Chemical Company
    Inventor: Ted A. Morgan
  • Patent number: 4801728
    Abstract: The present invention relates to reaction mixtures and processes which employ an .omega.-phase catalyst for carrying out displacement reactions at a substantially enhanced rate.
    Type: Grant
    Filed: June 25, 1986
    Date of Patent: January 31, 1989
    Assignee: M&T Chemicals Inc.
    Inventors: Charles L. Liotta, Edward M. Burgess