Preparing Alicyclic Ring Containing Compound Directly By Amination Patents (Class 564/445)
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Patent number: 5288910Abstract: 4-amino-2-buten-1-ol is formed by the regioselective addition of primary amines or ammonia to 3,4-epoxy-1-butene. A quantity of a the primary amine or ammonia is reacted with 3,4-epoxy-1-butene in a reaction medium in the presence of a catalyst. The reaction medium is a liquid which has an E.sub.T (30) no less than about 32. The catalyst is a complex of palladium and phosphine ligands.Type: GrantFiled: September 4, 1992Date of Patent: February 22, 1994Assignee: Eastman Kodak CompanyInventor: Yann Hung
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Patent number: 5284976Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group. attached to boron, B is boron and Me is methyl.Type: GrantFiled: July 19, 1993Date of Patent: February 8, 1994Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5276195Abstract: A process for preparing a dimethylorganoborane represented by the formula R*BMe.sub.2 wherein R* is a chiral organyl group attached to the boron, B is boron and Me is methyl comprising treating a chiral boronic ester R*B(OR').sub.2 with a methyl magnesium salt or trimethylaluminum wherein R* is the same chiral organyl group and R' is alkyl.Type: GrantFiled: July 14, 1993Date of Patent: January 4, 1994Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5254707Abstract: The process for preparing a compound of the formula:Cp'YNHRwherein: Cp' is a cyclopentadienyl or a substituted cyclopentadienyl group, Y is a covalent bridging group which contains one or more group 14 elements, and R is a C.sub.1 to C.sub.20 hydrocarbyl or substituted hydrocarbyl group, the process comprising reacting a ligand of the formula Cp'YX, wherein Cp' and Y are as defined above and X is halogen, with a substantially equimolar amount of a primary amine of the formula NH.sub.2 R, wherein R is as defined above, in an inert solvent in the presence of a HX scavenger at an elevated temperature of at least about 35.degree. C., so as to form said compound.Type: GrantFiled: December 7, 1992Date of Patent: October 19, 1993Assignee: Ethyl CorporationInventors: Jamie R. Strickler, John M. Power, Meng-Sheng Ao
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Patent number: 5214209Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group,attached to boron, B is boron and Me is methyl.Type: GrantFiled: March 26, 1990Date of Patent: May 25, 1993Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5210310Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group, attached to boron, B is boron and Me is methyl.Type: GrantFiled: March 26, 1990Date of Patent: May 11, 1993Assignee: Aldrich Chemical Co., Inc.Inventor: Herbert C. Brown
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Patent number: 5055618Abstract: The object of this invention is the preparation of .alpha.,.omega.-diamines from .alpha., .omega.-dialdehydes in a method which comprises the reaction of a starting mixture of said dialdehyde, a primary amine, and water to form a reaction mixture, followed by treatment of said reaction mixture with excess ammonia and hydrogen in the presence of a hydrogenation catalyst to produce a final mixture.Type: GrantFiled: May 21, 1990Date of Patent: October 8, 1991Assignee: Hoechst AktiengesellschaftInventors: Detlef Kampmann, Jurgen Weber, Claus Kniep
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Patent number: 5041675Abstract: This invention relates to a process for preparing 3(4),8(9)-bis(aminomethyl)tricyclo[5.2.1.0.sup.2,6 ]decane. The starting material for the synthesis of this compound is dicyclopentadiene, which is hydroformylated in the presence of a rhodium compound and subjected to reductive amination without the hydroformylation catalyst being separated from the reaction mixture.Type: GrantFiled: August 17, 1990Date of Patent: August 20, 1991Assignee: Hoechst AktiengesellschaftInventors: Rainer Lukas, Klaus Mathieu, Franz Thonnessen, Georg Dambkes, Hanswilhelm Bach
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Patent number: 4992150Abstract: A process for preparing oil-soluble nitrogen-containing compounds which comprises subjecting nitrogen-containing telogens and alpha-olefin taxogens to radical telomerization reaction. The nitrogen-containing compounds are mixtures of telomers having an average molecular weight not less than 300 and a nitrogen content of from 0.1 to 10 wt %. The compound may be further reacted with boron-bearing compounds or boron compounds to obtain oil-soluble nitrogen and boron-containing compounds. These compounds are useful as additives for fuel oils and lubricating oils.Type: GrantFiled: April 13, 1989Date of Patent: February 12, 1991Assignee: Nippon Oil Co, Ltd.Inventors: Jinichi Igarashi, Harumichi Watanabe
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Patent number: 4929759Abstract: Amines are prepared from an olefin and ammonia or a primary or secondary amine, or a mixture of these, in the presence of a borosilicate or borogermanate zeolite of the pentasil type as a catalyst, by a process in which the amine obtained is isolated from the reaction mixture, and unreacted starting materials are recycled.Type: GrantFiled: October 6, 1989Date of Patent: May 29, 1990Assignee: BASF AktiengesellschaftInventors: Volker Taglieber, Wolfgang Hoelderich, Rudolf Kummer, Wolf D. Mross, Guenter Saladin
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Patent number: 4827031Abstract: The process for preparing aliphatic and aromatic amines by reacting an olefin with either ammonia, a primary amine, or a secondary amine at elevated temperature in the presence of an ammonium halide catalyst, preferably a catalyst-promoter combination, is disclosed herein.Type: GrantFiled: May 19, 1987Date of Patent: May 2, 1989Assignee: Pennwalt CorporationInventors: David M. Gardner, Paul J. McElligott, Roger T. Clark
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Patent number: 4705897Abstract: Bicyclic diamines are prepared by a process comprising reacting 5-vinyl-2-norbornene or norbornadiene, synthesis gas and an amine from the group consisting of primary amines and secondary amines in the presence of a catalyst comprising a ruthenium-containing compound, an amide solvent and a quaternary phosphonium salt.Type: GrantFiled: May 5, 1986Date of Patent: November 10, 1987Assignee: Texaco Inc.Inventor: David C. Alexander
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Patent number: 4670599Abstract: This invention relates to 2,2-dichloro-3,3-dimethylcyclopropylmethylamine, a novel compound which is useful as an agricultural and horticultural fungicide or as a synthetic intermediate for other cyclopropyl derivatives and other compounds, and to a process for production thereof.Type: GrantFiled: September 21, 1984Date of Patent: June 2, 1987Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Kozo Shiokawa, Shinzo Kagabu, Shinji Sakawa
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Patent number: 4658062Abstract: Novel amine terminated polybutadiene compounds of the formula: ##STR1## wherein R is hydrogen, a straight or branched chain alkyl group containing from 1 to 10 carbon atoms or a substituted or unsubstituted aryl or aralkyl group containing one or more benzenoid rings which may be fused or joined by single valency bonds, and n is an integer of from about 5 to 1500 and a process for the preparation thereof.Type: GrantFiled: June 24, 1985Date of Patent: April 14, 1987Assignee: Atlantic Richfield CompanyInventors: Harry R. Hinney, Jamil Baghdadchi
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Patent number: 4605769Abstract: Alkanoamines such as diethylaminopropanol is prepared by reacting an alkylene oxide and either an amine or ammonia is the presence of a salt of a fluorosulphonic acid.Type: GrantFiled: June 12, 1985Date of Patent: August 12, 1986Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4602088Abstract: A method for the preparation of enamines wherein a conjugated diene is reacted with a secondary amine, carbon monoxide and hydrogen (synthesis gas) in solvent solution in the presence of a rhodium catalyst. In accordance with the preferred embodiment, butadiene is reacted with a dialkylamine and synthesis gas in an organic solvent in the presence of a rhodium catalyst to provide the corresponding 1,3-pentadienyl dialkylamine in good yield and with good selectivity.Type: GrantFiled: July 26, 1984Date of Patent: July 22, 1986Assignee: Texaco Inc.Inventor: Jiang-Jen Lin
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Patent number: 4582904Abstract: Synthesis of organic amines by condensation of organic hydroxy compound with ammonia or a primary or secondary amine in the presence of a rare earth metal hydrogen phosphate catalyst.Type: GrantFiled: January 6, 1984Date of Patent: April 15, 1986Assignee: Air Products and Chemicals, Inc.Inventors: James E. Wells, Victoria Eskinazi
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Patent number: 4536602Abstract: The present invention involves the catalytic amination of olefins with ammonia, a primary amine, or a secondary amine using a perfluorinated organic acid catalyst.Type: GrantFiled: June 1, 1984Date of Patent: August 20, 1985Assignee: Air Products and Chemicals, Inc.Inventor: Michael Deeba
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Patent number: 4487966Abstract: 3-Aminomethyl-1-(3-aminopropyl-1-methyl)-4-methylcyclohexane and a process for the preparation of this new compound, which uses limonene and/or monohydroformylation products of limonene as starting substances and proceeds via a dihydroformylation product of limonene. The new compound is useful as a corrosion inhibitor, as a crosslinking agent for epoxide resins and as a chain lengthening agent for NCO prepolymers.Type: GrantFiled: July 15, 1983Date of Patent: December 11, 1984Assignee: Bayer AktiengesellschaftInventors: Paul Fiedler, Rudolf Braden
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Patent number: 4375002Abstract: This invention relates to an improvement in the vapor phase catalytic production of an amine by the reaction of a mixture comprising an olefin having from 2 to 8 carbon atoms and ammonia or ammonia type compound. The improvement which provides for high selectivity to the amine resides in the use of an alumino silicate as the catalyst.Type: GrantFiled: April 8, 1981Date of Patent: February 22, 1983Assignee: Air Products and Chemicals, Inc.Inventors: John O. H. Peterson, Howard S. Fales
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Patent number: 4340717Abstract: Nitrogen-containing compounds are provided which are selected from compounds having the following formula: ##STR1## wherein X is selected from OH and NH.sub.2, R.sub.1 is selected from --CH.dbd.CH.sub.2 and --C.sub.2 H.sub.5, and R.sub.2 is selected from --NH.sub.2 and: ##STR2## where R.sub.1 has the value indicated above.Type: GrantFiled: March 12, 1981Date of Patent: July 20, 1982Assignee: Milliken Research CorporationInventor: Edward W. Kluger
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Patent number: 4322530Abstract: A process for alkylating a polyamine by contacting, in a liquid media, a polyamine, an olefinic compound, carbon monoxide, and a hydrogen source in the presence of a catalytic amount of a rhodium atom containing compound selected from metallic rhodium, rhodium salts, rhodium oxides, rhodium carbonyls and ligands thereof at a temperature of from about 50.degree. C. to 250.degree. C. and at a pressure of from about 30 to about 300 atmospheres.Type: GrantFiled: February 22, 1980Date of Patent: March 30, 1982Assignee: W. R. Grace & Co.Inventor: Felek Jachimowicz
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Patent number: 4321271Abstract: Compounds of formula (I) ##STR1## wherein: R.sup.1 is C.sub.1-6 alkyl or C.sub.5-7 cycloalkyl;R.sup.2 is hydrogen or C.sub.1-6 alkyl; orNR.sup.1 R.sup.2 represents a heterocyclic ring having 5 to 7 ring atoms and only one hetero-atom; andR.sup.3 is C.sub.1-4 alkyl, one carbon atom of which is di- or tri-halogenatedor salts thereof are useful in promoting growth of ruminants. Processes for their production, veterinary formulations and treatments are described.Type: GrantFiled: June 30, 1980Date of Patent: March 23, 1982Assignee: Beecham Group LimitedInventor: Brian G. McDonald
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Patent number: 4317932Abstract: A process for forming amines by contacting, in a liquid media, an olefinic compound, carbon monoxide, water, and ammonia in the presence of a rhodium atom containing compound selected from metallic rhodium, rhodium salts, rhodium oxides, and rhodium carbonyls and ligands thereof at a temperature of from 50.degree. to 250.degree. C. and at a pressure of from about 10 to about 300 atmospheres.Type: GrantFiled: February 22, 1980Date of Patent: March 2, 1982Assignee: W. R. Grace & Co.Inventor: Felek Jachimowicz
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Patent number: 4310695Abstract: Stable adducts suitable for curing epoxy resins are prepared by reacting a saturated epoxy resin with an excess of an amine and then reacting resulting epoxy-amine condensate with a base, preferably a strong base such as potassium or sodium hydroxide to remove at least 75% of the chlorine present in the condensate.Type: GrantFiled: November 17, 1980Date of Patent: January 12, 1982Assignee: Shell Oil CompanyInventor: Mark F. Dante
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Patent number: 4307250Abstract: This invention relates to an improvement in the vapor phase catalytic production of an amine by the reaction of a mixture comprising an olefin having from 2 to 8 carbon atoms and ammonia or ammonia type compound. The improvement which provides for high selectivity to the amine resides in the use of an alumino silicate as the catalyst.Type: GrantFiled: May 9, 1980Date of Patent: December 22, 1981Assignee: Air Products and Chemicals, Inc.Inventors: John O. H. Peterson, Howard S. Fales
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Patent number: 4302603Abstract: Monolefins such as ethylene are reacted with ammonia using alkali metal amide catalysts such as cesium or rubidium amides, or low melting mixtures of amides such as cesium/potassium, cesium/sodium or sodium/potassium amides. Conversions are improved compared to reactions using sodium or potassium amide alone. Conversions of ethylene are improved also when liquid ammonia is present.Type: GrantFiled: December 18, 1980Date of Patent: November 24, 1981Assignee: Allied Chemical CorporationInventor: Guido P. Pez
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Patent number: 4292242Abstract: Aminomethylation of olefins which employs a homogeneous catalyst which is a solution in a suitable solvent of mixed ruthenium and iron carbonyls. The overall reaction may be represented as follows: ##STR1## where R.sub.1 and R.sub.2 are hydrogen or essentially hydrocarbon groups. The reaction proceeds by way of an aldehyde intermediate. Accordingly, the starting material may be an aldehyde instead of an olefin.Type: GrantFiled: August 26, 1980Date of Patent: September 29, 1981Assignee: SRI InternationalInventor: Richard M. Laine
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Patent number: 4275237Abstract: Heavy reaction product after separation as by distillation of light reaction product or diadduct from a reaction mixture obtained by reaction of olefinically unsaturated nitriles with monoolefinic hydrocarbons containing an allylic hydrogen atom is hydrogenated to produce a polyamine mixture useful as an epoxy resin hardener yielding cured resins exhibiting low water absorption.Type: GrantFiled: August 6, 1979Date of Patent: June 23, 1981Assignee: Philips Petroleum CompanyInventors: Charles A. Drake, Ralph P. Williams
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Patent number: H1143Abstract: The invention is a process for reducing residual organic chloride in a hydrocarbyl amine by contacting the hydrocarbyl amine with a chlorine-displacing nucleophile selected from NaSCN, NaCN, and NaSPH where a portion of the residual organic chloride is converted to an inorganic chloride, and removing the inorganic chloride.Type: GrantFiled: October 15, 1991Date of Patent: February 2, 1993Assignee: Shell Oil CompanyInventor: Thomas H. Johnson