Preparing Alicyclic Ring Containing Compound Directly By Amination Patents (Class 564/445)
  • Patent number: 5288910
    Abstract: 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: Grant
    Filed: September 4, 1992
    Date of Patent: February 22, 1994
    Assignee: Eastman Kodak Company
    Inventor: Yann Hung
  • Patent number: 5284976
    Abstract: 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: Grant
    Filed: July 19, 1993
    Date of Patent: February 8, 1994
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5276195
    Abstract: 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: Grant
    Filed: July 14, 1993
    Date of Patent: January 4, 1994
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5254707
    Abstract: 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: Grant
    Filed: December 7, 1992
    Date of Patent: October 19, 1993
    Assignee: Ethyl Corporation
    Inventors: Jamie R. Strickler, John M. Power, Meng-Sheng Ao
  • Patent number: 5214209
    Abstract: 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: Grant
    Filed: March 26, 1990
    Date of Patent: May 25, 1993
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5210310
    Abstract: 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: Grant
    Filed: March 26, 1990
    Date of Patent: May 11, 1993
    Assignee: Aldrich Chemical Co., Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5055618
    Abstract: 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: Grant
    Filed: May 21, 1990
    Date of Patent: October 8, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Detlef Kampmann, Jurgen Weber, Claus Kniep
  • Patent number: 5041675
    Abstract: 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: Grant
    Filed: August 17, 1990
    Date of Patent: August 20, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rainer Lukas, Klaus Mathieu, Franz Thonnessen, Georg Dambkes, Hanswilhelm Bach
  • Patent number: 4992150
    Abstract: 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: Grant
    Filed: April 13, 1989
    Date of Patent: February 12, 1991
    Assignee: Nippon Oil Co, Ltd.
    Inventors: Jinichi Igarashi, Harumichi Watanabe
  • Patent number: 4929759
    Abstract: 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: Grant
    Filed: October 6, 1989
    Date of Patent: May 29, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Volker Taglieber, Wolfgang Hoelderich, Rudolf Kummer, Wolf D. Mross, Guenter Saladin
  • Patent number: 4827031
    Abstract: 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: Grant
    Filed: May 19, 1987
    Date of Patent: May 2, 1989
    Assignee: Pennwalt Corporation
    Inventors: David M. Gardner, Paul J. McElligott, Roger T. Clark
  • Patent number: 4705897
    Abstract: 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: Grant
    Filed: May 5, 1986
    Date of Patent: November 10, 1987
    Assignee: Texaco Inc.
    Inventor: David C. Alexander
  • Patent number: 4670599
    Abstract: 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: Grant
    Filed: September 21, 1984
    Date of Patent: June 2, 1987
    Assignee: Nihon Tokushu Noyaku Seizo K.K.
    Inventors: Kozo Shiokawa, Shinzo Kagabu, Shinji Sakawa
  • Patent number: 4658062
    Abstract: 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: Grant
    Filed: June 24, 1985
    Date of Patent: April 14, 1987
    Assignee: Atlantic Richfield Company
    Inventors: Harry R. Hinney, Jamil Baghdadchi
  • Patent number: 4605769
    Abstract: 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: Grant
    Filed: June 12, 1985
    Date of Patent: August 12, 1986
    Assignee: BP Chemicals Limited
    Inventor: Michael J. Green
  • Patent number: 4602088
    Abstract: 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: Grant
    Filed: July 26, 1984
    Date of Patent: July 22, 1986
    Assignee: Texaco Inc.
    Inventor: Jiang-Jen Lin
  • Patent number: 4582904
    Abstract: 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: Grant
    Filed: January 6, 1984
    Date of Patent: April 15, 1986
    Assignee: Air Products and Chemicals, Inc.
    Inventors: James E. Wells, Victoria Eskinazi
  • Patent number: 4536602
    Abstract: 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: Grant
    Filed: June 1, 1984
    Date of Patent: August 20, 1985
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Michael Deeba
  • Patent number: 4487966
    Abstract: 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: Grant
    Filed: July 15, 1983
    Date of Patent: December 11, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Paul Fiedler, Rudolf Braden
  • Patent number: 4375002
    Abstract: 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: Grant
    Filed: April 8, 1981
    Date of Patent: February 22, 1983
    Assignee: Air Products and Chemicals, Inc.
    Inventors: John O. H. Peterson, Howard S. Fales
  • Patent number: 4340717
    Abstract: 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: Grant
    Filed: March 12, 1981
    Date of Patent: July 20, 1982
    Assignee: Milliken Research Corporation
    Inventor: Edward W. Kluger
  • Patent number: 4322530
    Abstract: 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: Grant
    Filed: February 22, 1980
    Date of Patent: March 30, 1982
    Assignee: W. R. Grace & Co.
    Inventor: Felek Jachimowicz
  • Patent number: 4321271
    Abstract: 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: Grant
    Filed: June 30, 1980
    Date of Patent: March 23, 1982
    Assignee: Beecham Group Limited
    Inventor: Brian G. McDonald
  • Patent number: 4317932
    Abstract: 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: Grant
    Filed: February 22, 1980
    Date of Patent: March 2, 1982
    Assignee: W. R. Grace & Co.
    Inventor: Felek Jachimowicz
  • Patent number: 4310695
    Abstract: 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: Grant
    Filed: November 17, 1980
    Date of Patent: January 12, 1982
    Assignee: Shell Oil Company
    Inventor: Mark F. Dante
  • Patent number: 4307250
    Abstract: 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: Grant
    Filed: May 9, 1980
    Date of Patent: December 22, 1981
    Assignee: Air Products and Chemicals, Inc.
    Inventors: John O. H. Peterson, Howard S. Fales
  • Patent number: 4302603
    Abstract: 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: Grant
    Filed: December 18, 1980
    Date of Patent: November 24, 1981
    Assignee: Allied Chemical Corporation
    Inventor: Guido P. Pez
  • Patent number: 4292242
    Abstract: 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: Grant
    Filed: August 26, 1980
    Date of Patent: September 29, 1981
    Assignee: SRI International
    Inventor: Richard M. Laine
  • Patent number: 4275237
    Abstract: 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: Grant
    Filed: August 6, 1979
    Date of Patent: June 23, 1981
    Assignee: Philips Petroleum Company
    Inventors: Charles A. Drake, Ralph P. Williams
  • Patent number: H1143
    Abstract: 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: Grant
    Filed: October 15, 1991
    Date of Patent: February 2, 1993
    Assignee: Shell Oil Company
    Inventor: Thomas H. Johnson