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)
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Patent number: 6103929Abstract: 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: GrantFiled: November 16, 1999Date of Patent: August 15, 2000Assignee: Eastman Chemical CompanyInventors: Daniel John Bayston, Jonathan Luke William Griffin, Arne Grumann, Mario Eugenio Cosimino Polywka, Ronald Michael Scott
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Patent number: 6090982Abstract: 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: GrantFiled: November 16, 1999Date of Patent: July 18, 2000Assignee: Eastman Chemical CompanyInventors: Daniel John Bayston, Jonathan Luke William Griffin, Arne Gruman, Mario Eugenio Cosimino Polywka, Ronald Michael Scott
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Patent number: 6040471Abstract: This invention relates to a process for making certain acetonitriles.Type: GrantFiled: October 15, 1998Date of Patent: March 21, 2000Assignee: SmithKline Beecham CorporationInventor: Ann Marie Diederich
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Patent number: 5972833Abstract: 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: GrantFiled: November 9, 1998Date of Patent: October 26, 1999Assignee: The Standard Oil CompanyInventors: James Frank Brazdil, Jr., Joseph Peter Bartek
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Patent number: 5961945Abstract: 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: GrantFiled: November 14, 1997Date of Patent: October 5, 1999Assignee: Degussa AktiengesellschaftInventors: Lukas M. J. Von Hippel, Jorg Sauer, Rudiger Schutte, Manfred Sauer, Dietrich Arntz
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Patent number: 5914424Abstract: 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: GrantFiled: November 5, 1997Date of Patent: June 22, 1999Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Toshio Nakamura, Hachiro Arai, Hideyuki Inaba, Hiroshi Yamamoto
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Patent number: 5854172Abstract: 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: GrantFiled: January 17, 1997Date of Patent: December 29, 1998Assignee: The Standard Oil CompanyInventors: James Frank Brazdil, Jr., Joseph Peter Bartek
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Patent number: 5847190Abstract: 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: GrantFiled: May 20, 1997Date of Patent: December 8, 1998Assignee: BASF AktiengesellschaftInventors: Wolfgang Paulus, Fritz Vogtle, Jorg Issberner
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Patent number: 5837878Abstract: 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: GrantFiled: August 5, 1996Date of Patent: November 17, 1998Assignee: Prolinx, Inc.Inventors: Mark L. Stolowitz, Robert J. Kaiser, Kevin P. Lund
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Patent number: 5756803Abstract: 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: GrantFiled: April 24, 1996Date of Patent: May 26, 1998Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Claude Casse, Frederic Kress, Philippe Morel
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Patent number: 5756802Abstract: 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: GrantFiled: November 25, 1996Date of Patent: May 26, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Yuejin Li, John Nelson Armor, Peter Charles Hohl
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Patent number: 5744627Abstract: 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: GrantFiled: August 5, 1996Date of Patent: April 28, 1998Assignees: Prolinx, Inc., SystemixInventors: Mark L. Stowolitz, Robert J. Kaiser, Kevin P. Lund, Steven M. Torkelson
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Patent number: 5703264Abstract: 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: GrantFiled: June 24, 1996Date of Patent: December 30, 1997Assignee: Kao CorporationInventors: Wataru Yoshida, Tetsuaki Fukushima, Hideki Taniguchi, Hiroshi Abe
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Patent number: 5656619Abstract: 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: GrantFiled: June 6, 1995Date of Patent: August 12, 1997Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5637750Abstract: 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: GrantFiled: August 18, 1995Date of Patent: June 10, 1997Assignee: Zeneca LimitedInventor: Daniel Levin
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Patent number: 5618965Abstract: 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: GrantFiled: March 4, 1996Date of Patent: April 8, 1997Assignee: CIBA-GEIGY CorporationInventor: Martin Kudschus
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Patent number: 5583081Abstract: 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: GrantFiled: August 31, 1993Date of Patent: December 10, 1996Assignees: Board of Supervisors of Louisiana State University and Agricultural and Mechanical College, Bulgarian Academy of SciencesInventors: Geoffrey L. Price, Vladislav Kanazirev
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Patent number: 5290357Abstract: 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: GrantFiled: December 22, 1992Date of Patent: March 1, 1994Assignee: Halliburton CompanyInventor: Larry Eoff
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Patent number: 5239084Abstract: 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: GrantFiled: September 10, 1992Date of Patent: August 24, 1993Assignee: Hoffmann-La Roche Inc.Inventors: Philippe Guerry, Synese Jolidon
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Patent number: 5128479Abstract: 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: GrantFiled: January 29, 1990Date of Patent: July 7, 1992Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5118827Abstract: 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: GrantFiled: July 16, 1990Date of Patent: June 2, 1992Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5059709Abstract: 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: GrantFiled: November 13, 1990Date of Patent: October 22, 1991Assignee: American Cyanamid CompanyInventors: John P. Dusza, Robert F. Church
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Patent number: 5024691Abstract: 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: GrantFiled: August 4, 1986Date of Patent: June 18, 1991Assignee: ICI Americas Inc.Inventor: Sreeramulu Nagubandi
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Patent number: 4908138Abstract: 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: GrantFiled: July 22, 1988Date of Patent: March 13, 1990Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Helmut Blum, Siglinde Hemmann
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Patent number: 4647686Abstract: 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: GrantFiled: August 31, 1981Date of Patent: March 3, 1987Assignee: Allied CorporationInventors: Divakaran Masilamani, Edward H. Manahan
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Patent number: 4628115Abstract: 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: GrantFiled: March 25, 1985Date of Patent: December 9, 1986Assignee: Hoffmann-La Roche Inc.Inventors: Matthew Carson, Ronald A. LeMahieu, William C. Nason
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Patent number: 4617405Abstract: 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: GrantFiled: September 25, 1984Date of Patent: October 14, 1986Assignee: A. E. Staley Manufacturing CompanyInventors: Donald E. Kiely, Martin Seidman