Reactant Is An Aldehyde Or Ketone, Or A Compound Having Carbon Double Bonded To Nitrogen (e.g., Ammoxidation Of Acrolein, Etc.) Patents (Class 558/315)
  • Patent number: 6103929
    Abstract: Disclosed is a process for the preparation of cyclopropylglycine by a 5-step process wherein cyclopropanecarboxaldehyde is reacted with an .alpha.-aminoalkylaromatic compound to obtain an imine which is reacted with a cyanide to produce an aminonitrile compound; the aminonitrile compound is hydrolyzed to the corresponding aminocarboxylic acid and finally the arylalkyl residue is removed from the amino group by hydrogenolysis.
    Type: Grant
    Filed: November 16, 1999
    Date of Patent: August 15, 2000
    Assignee: Eastman Chemical Company
    Inventors: Daniel John Bayston, Jonathan Luke William Griffin, Arne Grumann, Mario Eugenio Cosimino Polywka, Ronald Michael Scott
  • Patent number: 6090982
    Abstract: Disclosed is a process for the preparation of cyclopropylglycine by a 5-step process wherein cyclopropanecarboxaldehyde is reacted with an .alpha.-aminoalkylaromatic compound to obtain an imine which is reacted with a cyanide to produce an aminonitrile compound; the aminonitrile compound is hydrolyzed to the corresponding aminocarboxylic acid and finally the arylalkyl residue is removed from the amino group by hydrogenolysis.
    Type: Grant
    Filed: November 16, 1999
    Date of Patent: July 18, 2000
    Assignee: Eastman Chemical Company
    Inventors: Daniel John Bayston, Jonathan Luke William Griffin, Arne Gruman, Mario Eugenio Cosimino Polywka, Ronald Michael Scott
  • Patent number: 6040471
    Abstract: This invention relates to a process for making certain acetonitriles.
    Type: Grant
    Filed: October 15, 1998
    Date of Patent: March 21, 2000
    Assignee: SmithKline Beecham Corporation
    Inventor: Ann Marie Diederich
  • Patent number: 5972833
    Abstract: A method of preparing a catalyst having the elements and the proportions indicated by the following empirical formula:VSb.sub.m A.sub.a D.sub.d O.sub.xwhereA is one or more Ti, Sn, where Sn is always presentD is one or more Li, Mg, Ca, Sr, Ba, Co, Fe, Cr, Ga, Ni, Zn, Ge, Nb, Zr, Mo, W, Cu, Te, Ta, Se, Bi, Ce, In, As, B, Al and Mn whereinm is 0.5 to 10a is greater than zero to 10d is zero to 10x is determined by the oxidation state of the cations present,comprising making an aqueous slurry of a mixture of source batch materials comprising compounds of said elements to be included in the final catalyst, followed by drying and heat calcining the mixture to an active catalyst, wherein the source batch material for the tin is a solution which comprises SnO.sub.2.xH.sub.2 O wherein x.gtoreq.0 dispersed in tetraalkyl ammonium hydroxide wherein the tetraalkyl ammonium hydroxide is defined by the following formula:C.sub.n H.sub.2n+1 NOHwherein 5.gtoreq.n.gtoreq.
    Type: Grant
    Filed: November 9, 1998
    Date of Patent: October 26, 1999
    Assignee: The Standard Oil Company
    Inventors: James Frank Brazdil, Jr., Joseph Peter Bartek
  • Patent number: 5961945
    Abstract: An ammoxidizable compound is reacted with an ammonium salt, especially an inorganic ammonium salt, in the presence of a source of oxygen and an ammoxidation catalyst at 100 to 700.degree. C., preferably 200 to 700.degree. C., in order to produce cyano compounds of the formula R--CN, in which R is H or an organic group.
    Type: Grant
    Filed: November 14, 1997
    Date of Patent: October 5, 1999
    Assignee: Degussa Aktiengesellschaft
    Inventors: Lukas M. J. Von Hippel, Jorg Sauer, Rudiger Schutte, Manfred Sauer, Dietrich Arntz
  • Patent number: 5914424
    Abstract: In a process for producing acrylonitrile by the ammoxidation of propylene, comprising bringing, in a fluidized-bed reactor, a gas containing propylene, ammonia and molecular oxygen into contact with a highly-active ammoxidation catalyst (this catalyst being one which can attain a rate constant of 2 s.sup.-1 or more for the ammoxidation reaction of propylene, assuming that the reaction is a first-order reaction) which is in a state of being fluidized by the gas, the improvement comprising carrying out the ammoxidation under the following conditions:(a) the superficial gas velocity in the fluidized-bed reactor is maintained at 1 to 10 m/s under such an operation condition that the rate constant of the ammoxidation reaction of propylene is 2 s.sup.-1 or more, assuming that the reaction is a first-order reaction;(b) an area in which the density of fluidized solid matter is 100 kg/m.sup.
    Type: Grant
    Filed: November 5, 1997
    Date of Patent: June 22, 1999
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Toshio Nakamura, Hachiro Arai, Hideyuki Inaba, Hiroshi Yamamoto
  • Patent number: 5854172
    Abstract: A method of preparing a catalyst having the elements and the proportions indicated by the following empirical formula:VSb.sub.m A.sub.a D.sub.d O.sub.xwhereA is one or more Ti, Sn, where Sn is always presentD is one or more Li, Mg, Ca, Sr, Ba, Co, Fe, Cr, Ga, Ni, Zn, Ge, Nb, Zr, Mo, W, Cu, Te, Ta, Se, Bi, Ce, In, As, B, Al and Mn whereinm is 0.5 to 10a is greater than zero to 10d is zero to 10x is determined by the oxidation state of the cations present,comprising making an aqueous slurry of a mixture of source batch materials comprising compounds of said elements to be included in the final catalyst, followed by drying and heat calcining the mixture to an active catalyst, wherein the source batch material for the tin is a solution which comprises SnO.sub.2.xH.sub.2 O wherein x.gtoreq.0 dispersed in tetraalkyl ammonium hydroxide wherein the tetraalkyl ammonium hydroxide is defined by the following formula:C.sub.n H.sub.2n+1 NOHwherein5.gtoreq.n.gtoreq.
    Type: Grant
    Filed: January 17, 1997
    Date of Patent: December 29, 1998
    Assignee: The Standard Oil Company
    Inventors: James Frank Brazdil, Jr., Joseph Peter Bartek
  • Patent number: 5847190
    Abstract: The present invention relates to dendritic, nitrogen-containing organic compounds containing at least 4 planar-chiral or axial-chiral groups, where these planar-chiral or axial-chiral groups are linked as Schiff's bases to the primary amino groups of compounds of the formula (I)(R.sup.1 R.sup.1)N--X--N(R.sup.1 R.sup.1) (I)whereR.sup.1 is (R.sup.2 R.sup.2)N--(CH.sub.2).sub.2 -- or (R.sup.2 R.sup.2)N--(CH.sub.2).sub.3 --,R.sup.2 is hydrogen or (R.sup.3 R.sup.3)N--CH.sub.2).sub.2 -- or (R.sup.3 R.sup.3)N--(CH.sub.2).sub.3 --,R.sup.3 is hydrogen or (R.sup.4 R.sup.4)N--(CH.sub.2).sub.2 -- or (R.sup.4 R.sup.4)N--(CH.sub.2).sub.3 --,R.sup.4 is hydrogen or (R.sup.5 R.sup.5)--N--(CH.sub.2).sub.2 -- or (R.sup.5 R.sup.5)N--(CH.sub.2).sub.3 --,R.sup.5 is hydrogen or (R.sup.6 R.sup.6)N--(CH.sub.2).sub.2 -- or (R.sup.6 R.sup.6)N--(CH.sub.2).sub.3 -- andR.sup.6 is hydrogen,X is an aliphatic and/or aromatic group, which may contain heteroatoms,which are suitable as catalysts for asymmetrical homogeneous catalysis.
    Type: Grant
    Filed: May 20, 1997
    Date of Patent: December 8, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Paulus, Fritz Vogtle, Jorg Issberner
  • Patent number: 5837878
    Abstract: Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula CIII, General Formula CIV, and General Formula CVI. In one embodiment, the reagents of General Formula CIII may be used to produce, after condensation with a bioactive species (BAS), the reagent of General Formula CIV. The reagent of General Formula CIV may be used to form a complex with a boron compound, such as a complex shown in General Formula CVI.
    Type: Grant
    Filed: August 5, 1996
    Date of Patent: November 17, 1998
    Assignee: Prolinx, Inc.
    Inventors: Mark L. Stolowitz, Robert J. Kaiser, Kevin P. Lund
  • 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: 5756802
    Abstract: Acetonitrile is produced directly from alkanes or alkenes by ammoxidation over a catalyst which is a silica-alumina exchanged with a metal of Period 4, Groups VIIA and VIII of the Periodic Table. The silica-alumina can be amorphous but is preferably crystalline zeolite. Preferred zeolite include ZSM-5, beta, NU-87 and USY. Cobalt is the favored metal for exchange. Particularly good results are obtained when the zeolite has been modified with a surface coating of silicon oxides prior to the metal exchange or modified with a boron or phosphorous containing compound followed by calcination. Ammoxidation of alkanes produce alkenes as a byproduct which can be recycled to the reaction to increase acetonitrile yield.
    Type: Grant
    Filed: November 25, 1996
    Date of Patent: May 26, 1998
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Yuejin Li, John Nelson Armor, Peter Charles Hohl
  • Patent number: 5744627
    Abstract: Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula III, General Formula IV, and General Formula VI. In one embodiment, the reagents of General Formula III may be used to produce, after condensation with a bioactive species (BAS), the reagent of General Formula IV. The reagent of General Formula IV may be used to form a complex with a boron compound, such as a complex shown in General Formula VI.
    Type: Grant
    Filed: August 5, 1996
    Date of Patent: April 28, 1998
    Assignees: Prolinx, Inc., Systemix
    Inventors: Mark L. Stowolitz, Robert J. Kaiser, Kevin P. Lund, Steven M. Torkelson
  • Patent number: 5703264
    Abstract: The process for producing an aliphatic nitrile comprising reacting an aliphatic alcohol having 6 to 40 carbon atoms with ammonia (a) in the presence of a copper/transition metal element in the fourth period other than Cr/platinum group element in the eighth group catalyst, (b) under a reaction system pressure in the range of from atmospheric pressure to 100 atm, (c) at a reaction system temperature in the range of from 100.degree. to 250.degree. C., (d) while introducing at least one gas selected from the group consisting of inert gases and hydrogen gas into the reaction system, (e) removing water formed by the reaction out of the reaction system, and (f) controlling the amount of the ammonia contained in the gas (exclusive of the water formed by the reaction) discharged out of the reaction system to 5 to 50% by volume based on the volume of the gas discharged (exclusive of the water formed by the reaction) makes it possible to produce various kinds of aliphatic nitriles.
    Type: Grant
    Filed: June 24, 1996
    Date of Patent: December 30, 1997
    Assignee: Kao Corporation
    Inventors: Wataru Yoshida, Tetsuaki Fukushima, Hideki Taniguchi, Hiroshi Abe
  • Patent number: 5656619
    Abstract: Abstract of the Disclosure: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: August 12, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5637750
    Abstract: A method for the preparation of a 2-hydroxybenzonitrile which comprises reacting hydroxylamine with a 2-hydroxyarylaldehyde which is at least partially in the form of a salt and/or complex of a metal of Group II, Group III, Group IVA or Group VIA of the Periodic Table and dehydrating the 2-hydroxyarylaldoxime so formed.
    Type: Grant
    Filed: August 18, 1995
    Date of Patent: June 10, 1997
    Assignee: Zeneca Limited
    Inventor: Daniel Levin
  • Patent number: 5618965
    Abstract: Process for preparing a nitrile of the formula (I) ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 are for example hydrogen, halogen, cyano, hydroxyl, carboxyl, alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, aryl, aryloxy, arylthio or arylamino, or R.sub.2 and R.sub.3 together form a substituted or unsubstituted 4-membered carbon bridge,by reacting an aldehyde of the formula (II) ##STR2## with a hydroxylammonium salt followed by dehydration by heating to an elevated temperature, wherein the reaction takes place in the presence of an anhydrous inorganic sulfate and in the absence of diluents from the group consisting of carboxylic acids, strongly polar aprotic solvents, sulfur compounds and heteroaromatic basic nitrogen compounds.The nitriles obtainable by the process of the invention are valuable intermediates for, in particular, the preparation of diketopyrrolopyrrole pigments.
    Type: Grant
    Filed: March 4, 1996
    Date of Patent: April 8, 1997
    Assignee: CIBA-GEIGY Corporation
    Inventor: Martin Kudschus
  • Patent number: 5583081
    Abstract: A catalyst useful in the conversion of nitrogen oxides or in the synthesis of nitriles or imines from amines, formed by preparing an intimate mechanical mixture of a copper (II)-containing species, such as CuO or CuCl.sub.2, or elemental copper, with a zeolite having a pore mouth comprising 10 oxygen atoms, such as ZSM-5, converting the elemental copper or copper (II) to copper (I), and driving the copper (I) into the zeolite.
    Type: Grant
    Filed: August 31, 1993
    Date of Patent: December 10, 1996
    Assignees: Board of Supervisors of Louisiana State University and Agricultural and Mechanical College, Bulgarian Academy of Sciences
    Inventors: Geoffrey L. Price, Vladislav Kanazirev
  • Patent number: 5290357
    Abstract: A composition for and method of dispersing particles of hydraulic cement in a slurry of hydraulic cement in water, wherein the composition is the reaction product of a ketone, an aldehyde, a cyanide and, optionally, a sulfite. The dispersant properties of the composition can be enhanced by further reacting the composition with hydroxide.
    Type: Grant
    Filed: December 22, 1992
    Date of Patent: March 1, 1994
    Assignee: Halliburton Company
    Inventor: Larry Eoff
  • Patent number: 5239084
    Abstract: Antimycotically-active compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently are hydrogen, C.sub.1-7 -alkyl or C.sub.2-7 -alkenyl or together are a straight chain C.sub.2-4 -alkylene; R.sup.3 and R.sup.4 each independently are hydrogen or C.sub.1-7 -alkyl; R.sup.5 and R.sup.6 each independently are hydrogen, halogen, trifluoromethyl, nitro, cyano, C.sub.1-7 -alkoxy or C.sub.1-7 -alkyl; and Q is an unsubstituted or substituted phenyl or naphthyl group, wherein the substituents are at least one of halogen, trifluoromethyl, cyano, nitro, C.sub.1-7 -alkyl, C.sub.1-7 -alkoxy; C.sub.2-10 -alkenyl; or a substituted or unsubstituted C.sub.1-10 -alkyl group wherein said substituents are at least one hydroxy group; andpharmaceutically acceptable acid addition salts thereof.
    Type: Grant
    Filed: September 10, 1992
    Date of Patent: August 24, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Philippe Guerry, Synese Jolidon
  • Patent number: 5128479
    Abstract: Oxidized diphenylheteroalkanes of the formula I ##STR1## where R.sup.1 to R.sup.6 and A have the meanings specified in the description, and the preparation thereof are described. The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: January 29, 1990
    Date of Patent: July 7, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5118827
    Abstract: Novel monocyclic terpene derivative of the formula: ##STR1## wherein R is hydrogen atom, trimethylsilyl group or 1-ethoxyethyl group, and novel intermediate therefor. The terpene derivative (I) is a useful intermediate for preparing Sarcophytol A having an anti-carcinogenesis promoter activity and an antitumor activity.
    Type: Grant
    Filed: July 16, 1990
    Date of Patent: June 2, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 5059709
    Abstract: A novel process for producing .alpha.-[(dialkylamino) substituted-methylene].beta.-oxo-(substituted) propanenitriles of the formula: ##STR1## where R, R.sub.1 and R .sub.2 are defined in the specification by reacting a substituted isoxazole with a diaklylamide dimethylacetal is provided.
    Type: Grant
    Filed: November 13, 1990
    Date of Patent: October 22, 1991
    Assignee: American Cyanamid Company
    Inventors: John P. Dusza, Robert F. Church
  • Patent number: 5024691
    Abstract: As new compounds, substituted aryloxyphenoxy benzamides having the formula ##STR1## in which X is CH or nitrogen; Y is chlorine, bromine, fluorine, iodine, methyl, cyano or hydrogen; Z is hydrogen, chlorine, bromine, fluorine, iodine, CH.sub.n, F.sub.3-n where n is an integer from 0 to 3; R is nitrogen dioxide, hydrogen or halogen; R' is hydrogen, CH.sub.3, lower alkyl, having 1-10 carbon atoms, SCCl.sub.3, ##STR2## or --PO.sub.3 R.sup.3.sub.2 wherein R.sup.3 is hydrogen, alkyl having 1-10 carbon atoms, aryl, or an equivalent of base such as a salt; R" is cyano, --C.tbd.CH, ##STR3## wherein R.sup.4 is hydrogen, alkyl having 1-10 carbon atoms, aryl or an equivalent of base such as a salt; and m is 0, 1, 2 or 3.
    Type: Grant
    Filed: August 4, 1986
    Date of Patent: June 18, 1991
    Assignee: ICI Americas Inc.
    Inventor: Sreeramulu Nagubandi
  • Patent number: 4908138
    Abstract: Hydroxyacetonitrile diphosphonic acid corresponding to the following general formula ##STR1## in which M represents H or a cation of a base, and salts thereof; to a process for their preparation comprising reacting 3-R.sup.1 -3-oxo-1-aminopropane-1,1-diphosphonic acids corresponding to the following general formula ##STR2## in which R.sup.1 is a tertiary substituted alkyl group, an optionally substituted cycloalkyl group or an optionally substituted aryl or heteroaryl radical, with nitrous acid, the secondary product R.sup.1 -COOH and unreacted starting material are separated off from the reaction mixture and the hydroxyacetonitrile diphosphonic acid is obtained in the form of a salt by addition of a base; and to the use of the above compounds as complexing agents and as thresholders.
    Type: Grant
    Filed: July 22, 1988
    Date of Patent: March 13, 1990
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Helmut Blum, Siglinde Hemmann
  • Patent number: 4647686
    Abstract: This invention relates to a process for preparing keto-cyano alkane compounds by treating the corresponding alpha substituted cycloalkanone compound with oxygen and ammonia in the presence of a transition metal catalyst.
    Type: Grant
    Filed: August 31, 1981
    Date of Patent: March 3, 1987
    Assignee: Allied Corporation
    Inventors: Divakaran Masilamani, Edward H. Manahan
  • Patent number: 4628115
    Abstract: The invention relates to compounds of the formula ##STR1## wherein R is hydrogen or lower alkyl, Z is alkylene of 1 to 10 carbon atoms, --(C*H.sub.2).sub.3 --C.tbd.C--, --C*H.sub.2 --C.tbd.C--(CH.sub.2).sub.3 --, and --(CH.sub.2).sub.2 O].sub.n (CH.sub.2).sub.2 -- wherein n is an integer of 1 to 3, the carbon atom marked with an asterisk is linked to the phenoxy moiety,and salts thereof with pharmaceutically acceptable bases. The compounds of formula I are antagonists of slow reacting substance of anaphylaxis (SRS-A; leukotrienes C.sub.4, D.sub.4 and E.sub.4), which renders them useful as agents for the treatment of allergic conditions.
    Type: Grant
    Filed: March 25, 1985
    Date of Patent: December 9, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Matthew Carson, Ronald A. LeMahieu, William C. Nason
  • Patent number: 4617405
    Abstract: Alpha, beta carbonyl compounds are prepared from an acid anhydride selected from the group consisting of glutaric anhydride and 3-alkyl glutaric anhydride, and a beta-hydroxy carbonyl compound having the following chemical formula:R.sub.2 COH--CHR--CRO or R.sub.2 COH--CHR--CNwhere each R is any substitutent group.The process comprises: (a) reacting the acid anhydride and the beta-hydroxy carbonyl compound in the presence of a catalytically effective amount of an acid catalyst to form an ester; (b) reacting the ester in the presence of a catalytically effective amount of a base catalyst to form a alpha, beta-unsaturated carbonyl compound and a carboxylic acid; and (c) separating the alpha, beta-unsaturated carbonyl compound and the carboxylic acid.
    Type: Grant
    Filed: September 25, 1984
    Date of Patent: October 14, 1986
    Assignee: A. E. Staley Manufacturing Company
    Inventors: Donald E. Kiely, Martin Seidman