Aldimines Or Ketimines Which Are Acyclic Patents (Class 564/278)
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Patent number: 6020527Abstract: The present invention describes a stereospecific process for the isomerization of prochiral allyl amines into chiral enamines and imines, using Rh, Ir or Ru catalysts which carry chiral phosphine ligands derived from ferrocenes, which may be immobilized on a solid carrier, or from steroides. The process is in particular appropriate for the production of chiral citronellal, which can be obtained in optical purities of greater than 95%.Type: GrantFiled: March 31, 1999Date of Patent: February 1, 2000Assignee: Firmenich SAInventors: Christian Chapuis, Michel Barthe
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Patent number: 5998627Abstract: Nitrones are produced by reaction of primary amine with aldehyde or ketone, in the presence of a transition metal-containing oxidation catalyst, and a peroxidic compound. The nitrone can then be reacted with a vinylaromatic compound to produce a 2-hydrocarbyl-5-arylisoxazolidine. Both such reactions can be conducted concurrently by including the vinylaromatic compound in the initial reaction mixture. Hydrogenation of the 2-hydrocarbyl-5-arylisoxazolidine, e.g., using hydrogen and a palladium-carbon catalyst, forms an N-hydrocarbyl-3-aryl-3-hydroxypropylamine. Such reactions enable, inter alia, synthesis of the racemic hydrochloride salt of N-methyl-3-phenyl-3-[4-trifluoromethyl)phenoxy]-propylamine, known generically as fluoxetine hydrochloride, a widely used antidepressant.Type: GrantFiled: August 4, 1997Date of Patent: December 7, 1999Assignee: Albemarle CorporationInventor: Kevin J. Theriot
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Patent number: 5744642Abstract: The invention relates to a novel process for the preparation of aliphatic imines of the general formula (I): ##STR1## in which R.sup.1 is alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, arylalkyl or heteroarylalkyl, each of which is optionally substituted, andR.sup.2 is optionally substituted alkyl andcharacterized in thatamines of the general formula (II):R.sup.1 --NH.sub.2 (II)in whichR.sup.1 is as defined above,are reacted with aldehydes of the general formula (III): ##STR2## in which R.sup.2 is as defined above,in the presence of a practically water-immiscible organic solvent, at temperatures between -30.degree. C. and +50.degree. C.Type: GrantFiled: February 24, 1995Date of Patent: April 28, 1998Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Werner Lindner
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Patent number: 5731462Abstract: The subject of the present invention is a new process for obtaining nitrones. It more particularly relates to a process for obtaining N-monosubstituted hydroxylamine comprising a stage in which a nitrone is formed from a secondary amine in the presence of an oxidizing agent and of at least one C.dbd.O containing species chosen from the group consisting of carbon dioxide, hydrogencarbonates and carbonates.Type: GrantFiled: December 18, 1996Date of Patent: March 24, 1998Assignee: Elf Atochem S.A.Inventors: Christophe Calais, Remy Teissier
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Patent number: 5726334Abstract: This invention relates to a process for the preparation of ruthenium complexes of the formula RuH.sub.2 L.sub.2 (PR.sub.3).sub.2, wherein each L is independently H.sub.2 or an additional equivalent of PR.sub.3, and each R is independently H, a hydrocarbyl group, or an assembly of at least two hydrocarbyl groups connected by ether or amine linkages, comprising contacting a source of ruthenium and PR.sub.3 with gaseous hydrogen in the presence of a strong base, a phase-transfer catalyst, water and an organic solvent; and the use of certain classes of ruthenium complexes as catalysts in hydrogenation, and reductive hydrolysis processes.Type: GrantFiled: September 19, 1996Date of Patent: March 10, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Richard Paul Beatty, Rocco Angelo Paciello
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Patent number: 5719298Abstract: A method of producing a pantothenic acid derivative of formula (I): ##STR1## wherein each of R.sup.1 and R.sup.2 is different, and is a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, or a phenyl group; or a straight chain aliphatic hydrocarbon group having 5 to 10 carbon atoms, is provided, including methods of producing the starting materials for producing the same and novel amine derivative that can be used for the production of the pantothenic acid derivative.Type: GrantFiled: May 22, 1995Date of Patent: February 17, 1998Assignee: Fujirebio Inc.Inventors: Hiroshi Ikawa, Hajime Matsumoto
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Patent number: 5689003Abstract: The invention relates to a novel ruthenium complex having the formula Ru(.eta..sup.3 --C.sub.6 H.sub.8 --PCy.sub.2)(PCy.sub.3)Cl, wherein Cy is cyclohexyl; its use in the preparation of RuHCl(H.sub.2)(PCy.sub.3).sub.2 and RuH.sub.2 (H.sub.2).sub.2 (PCy.sub.3).sub.2 ; and the use of the complexes as catalysts in hydrogenation, imination and reductive hydrolysis processes.Type: GrantFiled: May 8, 1996Date of Patent: November 18, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventors: Richard Paul Beatty, Rocco Angelo Paciello
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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: 5571922Abstract: An aldimine oxazolidine compound having the formula: ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are, individually, a hydrogen atom, a methyl or methylol group, an ethyl or ethylol group, a straight chain or branched chain alkyl or alkanol group, a cycloalkyl group, or an aryl group, including groups substituted by nitro, halogen, thiol and amino functional groups, such that when R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are hydrogen atoms, R.sub.3 and R.sub.4 are not hydrogen atoms; m and n are integers of one to five; and X is zero or a --R.sub.9 --Y--R.sub.10 -- group, wherein R.sub.9 and R.sub.Type: GrantFiled: November 13, 1995Date of Patent: November 5, 1996Assignee: Angus Chemical CompanyInventor: Chih-Yuch Chou
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Patent number: 5567845Abstract: Halogen-free fuel additives based on a long-chain hydrocarbon having a polar terminal group are obtained by reacting a hydroformylated olefin with a polyamine and hydrogenating the reaction product.Type: GrantFiled: October 16, 1995Date of Patent: October 22, 1996Assignee: BASF AktiengesellschaftInventors: Lothar Franz, Juergen Mohr, Peter Schreyer, Juergen Thomas, Knut Oppenlaender, Wolfgang Guenther
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Patent number: 5545705Abstract: The present invention relates to aldimines corresponding to the formulaX.sub.1 --[N.dbd.CHCH(R.sub.1)(R.sub.2)].sub.2whereinX.sub.1 represents the group obtained by the removal of the amino groups from 2-methyl-1,5-pentane diamine,R.sub.1 and R.sub.2 may be the same or different and represent optionally substituted hydrocarbon radicals, or R.sub.1 and R.sub.2 together with the .beta.-carbon atom from a cycloaliphatic or heterocyclic ring.The present invention relates to a clear, solvent-containing coating composition which containsa) an isocyanurate group-containing polyisocyanate which contains less than 5% by weight, based on the weight of component a), of allophanate and uretdione groups andb) an aldimine corresponding to the formulaX.sub.1 --[N.dbd.CHCH(R.sub.1)(R.sub.2)].sub.nwherein X.sub.1, R.sub.1 and R.sub.Type: GrantFiled: December 14, 1994Date of Patent: August 13, 1996Assignee: Bayer CorporationInventors: Sharon D. Hicks, Douglas A. Wicks, Scott A. Grace
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Patent number: 5504253Abstract: A method of making (R)-N- 1-(3-methoxyphenyl)ethyl!-3-(2-chlorobenzene)propanamine which involves reducing the appropriate amidyl or iminyl precursor with an appropriate reducing agent. The appropriate amidyl or iminyl precursor is made from a synthesis involving the use of (R)-3-methoxy-.alpha.-methylbenzylamine. A method of condensing a nitrile with a primary or secondary amine to form an imine involves the reaction of a nitrile with diisobutylaluminum hydride; and then reacting the resultant compound with a primary or secondary amine to form the imine. The process is especially useful for producing enantiomerically pure chiral imines, and, ultimately, amines. Typical such imines have the formula: ##STR1## wherein R, R.sub.1, R.sub.2 and R.sub.3 are independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, aryl and aralkyl.Type: GrantFiled: July 15, 1994Date of Patent: April 2, 1996Assignee: NPS Pharmaceuticals, Inc.Inventors: Bradford C. VanWagenen, Thomas E. D'Ambra
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Patent number: 5449827Abstract: The invention relates to an azomethine of the following composition: ##STR1## in which R.sup.1 is H or a branched or unbranched C.sub.1-14 -alkyl radical, andR.sup.2 is a branched or unbranched C.sub.1-14 -alkyl radical, an C.sub.1-14 alkyl-substituted phenyl radical or a C.sub.1 -C.sub.8 -(cyclo)-alkyl radical.It further relates to a process for preparing an azomethine, in which ##STR2## is reacted with the corresponding carbonyl compounds ##STR3## The invention also relates to the use of the azomethines for the preparation of certain polyazomethines (poly-Schiff bases), where the azomethines are reacted with diisocyanates or their adducts with polyols or their trimers, and to polyazomethine compounds.Type: GrantFiled: March 7, 1994Date of Patent: September 12, 1995Assignee: Huels AktiengesellschaftInventors: Rainer Lomoelder, Wilfried Paulen, Felix Schmitt, Elmar Wolf
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Patent number: 5371292Abstract: A process for the preparation of 3-aminomethyl-3,5,5-trimethyl-cyclohexylamine from 3-cyano-3,5,5-trimethyl-cyclohexanone, wherein the following stages are carried out in discrete reaction chambers:a) the 3-cyano-3,5,5-trimethyl-cyclohexanone is reacted in a first reaction chamber with excess ammonia over an acidic metal oxide catalyst at a temperature of from 20.degree. to 150.degree. C. and a pressure of from 15 to 500 bar, andb) in a second reaction chamber, the reaction product from stage a) is hydrogenated with hydrogen at a temperature of from 60.degree. to 150.degree. C. and a pressure of from 50 to 300 bar in the presence of excess ammonia over a catalyst containing cobalt, nickel, ruthenium, and/or some other noble metal, which catalyst optionally contains a basic component or is supported by neutral or basic supporting material.Type: GrantFiled: July 15, 1993Date of Patent: December 6, 1994Assignee: BASF AktiengesellschaftInventors: Franz Merger, Claus-Ulrich Priester, Tom Witzel, Gerhard Koppenhoefer, Wolfgang Harder
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Patent number: 5274182Abstract: Saturated, liquid, low molecular weight and low-viscosity isobutylene polymers terminally functionalized by special groups, which correspond to the following formula ##STR1## are produced by solution ozonolysis of high molecular weight isobutylene/diene copolymers containing diene monomers, stabilization of the products obtained after the ozone treatment by addition of peroxide decomposers and subsequent reduction with hydrogen in the presence of hydrogenation catalysts under pressures of 10 to 300 bar and at temperatures of 20.degree. to 300.degree. C., optionally in the presence of sulfur or amines or ammonia.Type: GrantFiled: June 26, 1992Date of Patent: December 28, 1993Assignee: Bayer AktiengesellschaftInventors: Richard Weider, Thomas Scholl
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Patent number: 5106723Abstract: Contrast enhancement compositions are provided which can be used to make contrast enhancement layer photoresist composites. The composites can be used to make patterned photoresists under mid-UV light and utilize photobleachable alkylnitrones.Type: GrantFiled: January 8, 1991Date of Patent: April 21, 1992Assignee: MicroSi, Inc.Inventors: Paul R. West, Gary C. Davis, Karen A. Regh
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Patent number: 5103058Abstract: Process for producing aliphatic imines and/or amines from aliphatic monohydric alcohols, such as higher molecular weight oxo alcohols, including ether alcohols, comprising the steps of dehydrogenating the alcohol to an aldehyde in situ in the presence of a zinc oxide and/or zinc salt/metal hydroxide dehydrogenation catalyst and a soluble amount of a primary aliphatic amine which condenses immediately with the aldehyde under reflux conditions, with continuous water removal, to form the corresponding aliphatic imine (Schiff base). The corresponding aliphatic amine can be formed by reducing or reductively aminating the imine in known manner to form corresponding primary, secondary or tertiary amines as desired.Type: GrantFiled: November 5, 1990Date of Patent: April 7, 1992Assignee: Exxon Chemical Patents IncInventors: Roy L. Pruett, Michael J. Keenan, Edmund J. Mozeleski
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Patent number: 5068408Abstract: A process for oxidizing an organic compound selected from an aliphatic, aromatic, aliphatic/aromatic, cycloaliphatic and heterocyclic alcohol, thiol, sulfide, aldehyde, amine, amide, ketone, acid, ether, ester, and organic compounds containing an activated carbon-carbon double bond, which process comprises contacting said organic compound dissolved in an organic solvent with a hypochlorous acid solution.Type: GrantFiled: January 31, 1990Date of Patent: November 26, 1991Assignee: Olin CorporationInventors: Robert J. Raynor, Budd L. Duncan
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Patent number: 5028724Abstract: A process for the vapor-phase synthesis of non-adduct volatile fluorinated and non-fluorinated metal-ligand complexes comprising contacting a .beta.-diketone or .beta.-ketoimine ligand with an inert carrier gas to vaporize the ligand, reacting the vaporized ligand with a metal species at a temperature sufficient to form the metal-ligand complex and recovering the metal-ligand complex by sublimation. The process is conducted in the absence of solvent thereby providing pure non-adduct metal-ligand complexes. Such complexes are particularly suited for specialty applications requiring use of high purity compounds.Type: GrantFiled: March 30, 1990Date of Patent: July 2, 1991Assignee: Air Products and Chemicals, Inc.Inventors: John C. Ivankovits, David A. Bohling, John A. T. Norman, David A. Roberts
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Patent number: 5011994Abstract: The invention pertains to a colorless ketimine or an adduct thereof displaying excellent color stability and usable as a cross-linking agent in a curable coating, impregnating, sealing or bonding composition wherein the ketimine is the adduct of a polyamine having a primary and a secondary amino group and containing at least 3 carbon atoms in a linear chain between both amino groups, and a ketone containing not more than 8 carbon atoms and having methylene groups adjacent to the carbonyl group. The invention also pertains to a process for preparing the ketimine and to the use of the ketimine in a curable composition.Type: GrantFiled: April 2, 1987Date of Patent: April 30, 1991Assignee: Alzo N.V.Inventors: Tamme Bartels, Wincenty L. S. Pilaszek
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Patent number: 5002993Abstract: Contrast enhancement compositions are provided which can be used to make contrast enhancement layer photoresist composites. The composites can be used to make patterned photoresists under mid-UV light and utilize photobleachable alkylnitrones.Type: GrantFiled: December 4, 1989Date of Patent: March 26, 1991Assignee: MicroSi, Inc.Inventors: Paul R. West, Gary C. Davis, Karen A. Regh
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Patent number: 4950790Abstract: Fluorinated .beta.-ketoimine ligands and highly volatile .beta.-ketoiminato metal complexes of the ligands are synthesized by silylating a fluorinated .beta.-diketone to form a silylenolether, and subsequently reacting the silylenolether with a primary amine to form the desired ligand having the structural formula: ##STR1## wherein R.sub.1 and R.sub.2 are independently linear or branched perfluorinated, C.sub.1 -C.sub.8 alkyl groups and R.sub.3 is any organic functionality such as a C.sub.1 -C.sub.8 alkyl, phenyl or hydroxyalkyl group, all of which can be partially or fully fluorinated. The corresponding metal complex is formed by treating the ligand with a metal halide.Type: GrantFiled: November 14, 1988Date of Patent: August 21, 1990Assignee: Air Products and Chemicals, Inc.Inventor: John A. T. Norman
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Patent number: 4789691Abstract: The subject of this invention is elastomers containing polyamide groups and polyurea groups in bonded form, which are prepared by the reaction of(a) at least one organic polyisocyanate and/or a modified polyisocyanate mixture having an NCO content of from 8 to 33.6 weight percent,(b) at least one polyazomethine and(c) at least one alkyl-substituted aromatic polyamine having a molecular weight up to 500,in the presence of or in the absence of(d) catalysts,whereby reaction products of polyoxyalkylenepolyamines, having a functionality of from 2 to 4 and an average molecular weight of from 180 to 10,000 and at least one organic aldehyde and/or preferably ketone, are used as the polyazomethines.Type: GrantFiled: March 15, 1988Date of Patent: December 6, 1988Assignee: BASF AktiengesellschaftInventors: Guenter Matzke, Peter Horn, Hans U. Schmidt
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Patent number: 4618501Abstract: An .alpha., .beta.-keto-imine having a nutty corn, cereal aroma which may be used as a flavoring composition for food and having the structure: ##STR1## and R.sup.1, R.sup.2 and R.sup.3 are selected from the group consisting of a saturated or unsaturated alkyl straight or branched chain hydrocarbon having from C.sub.1 to C.sub.3 carbon atoms but preferably having from C.sub.1 to C.sub.2 carbon atoms. Alternatively R.sup.3 may also be (CH.sub.3).sub.n -SH wherein n is 1 or 2.Type: GrantFiled: May 28, 1985Date of Patent: October 21, 1986Assignee: General Foods CorporationInventor: Thomas H. Parliment
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Patent number: 4596874Abstract: A nitrone is synthesized from a secondary amine by reacting a compound represented by the following general formula ##STR1## wherein R.sup.1 and R.sup.2 mean individually a hydrogen atom or an alkyl or aryl group and R.sup.3 denotes an alkyl or aryl group with a peroxide in the presence of a catalyst selected from the group consisting of tungsten compounds, molybdenum compounds, vanadium compounds, titanium compounds, palladium compounds, rhodium compounds, ruthenium compounds and nickel compounds. This process provides the nitrone by one-step oxidation of the secondary amine.Type: GrantFiled: March 8, 1984Date of Patent: June 24, 1986Assignee: The President of Osaka UniversityInventors: Shun-Ichi Murahashi, Hitoshi Mitsui
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Patent number: 4585892Abstract: .alpha.-Alkylated, acyclic .alpha.-aminocarboxylic acids of the formula ##STR1## where * represents a center of asymmetry, R.sup.1 is a lower alkyl, allyl, benzyl or substituted benzyl group and R.sup.2 is a lower alkyl, methoxymethyl, lower alkylmercaptoethyl, phenyl, phenyl substituted with alkyl or alkoxy, benzyl, or benzyl substituted with alkyl, alkoxy or halo are produced by an enantio-selective plural step process from the corresponding .alpha.-aminocarboxylic acid monomethyl or monoethyl amide. A particular advantage of the new process is that there can be produced from one educt-enantiomer, i.e. from an (S)- or an (R)-.alpha.-aminocarboxylic acid, selectively depending on the reaction conditions used the two enantiomeric forms of the desired .alpha.-alkyl-.alpha.-aminocarboxylic acid.Type: GrantFiled: September 27, 1984Date of Patent: April 29, 1986Assignee: Degussa AktiengesellschaftInventors: Dieter Seebach, Reto Naef
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Patent number: 4491538Abstract: A novel group of surface active agents is revealed. These surface active agents are the condensation product of an aldehyde or ketone of from 9 to 20 carbon atoms with a polyoxyalkyleneamine which is an amine terminated block copolymer of oxyethylene and oxypropylene groups.The Schiff bases of the present invention are characterized by the general formula: ##STR1## In this general formula, R.sub.1 and R.sub.2 can either be hydrogen or an alkyl radical such that the sum of carbon atoms in the radical R.sub.1 --C--R.sub.2 is from 9 to 20.R.sub.3 is a radical which may be an alkyl of from 1 to 4 carbon atoms.R.sub.3 is in the alternative the radicalH.sub.2 N[CH(CH.sub.3)CH.sub.2 ]--[OCH(CH.sub.3)CH.sub.2 ].sub.y --or ##STR2## In these formulae, y has an average value of from 1 to 3 and and x has an average value of from 4 to 60 such that the amount of polyoxyethylene in the Schiff base is greater than or equal to 40 wt. %.Type: GrantFiled: October 18, 1982Date of Patent: January 1, 1985Assignee: Texaco Inc.Inventor: David R. McCoy
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Patent number: 4429154Abstract: New fluorinated azomethines of the general formula ##STR1## in which X.sup.1 represents hydrogen, fluorine or chlorine,X.sup.2 represents hydrogen, fluorine or chlorine,R.sup.1 represents hydrogen or alkyl andR.sup.2 represents hydrogen or alkyl,a process for their preparation and their use as intermediate products.Type: GrantFiled: May 24, 1982Date of Patent: January 31, 1984Assignee: Bayer AktiengesellschaftInventors: Bernd Baasner, Erich Klauke, Hermann Hagemann, Engelbert Kuhle
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Patent number: 4332968Abstract: A method for separating primary and secondary amines by contacting a mixture thereof with mesityl oxide, which forms acetone and an adduct with the primary amine. Acetone is removed to force the reaction. The reaction is particularly useful for separating close boiling amines. The primary amine adducts have high boiling points, thereby allowing the secondary amine to be recovered in high purity by distillation. The primary amine may also be recovered by hydrolyzing the adduct which produces the primary amine and acetone.Type: GrantFiled: September 8, 1980Date of Patent: June 1, 1982Assignee: Chemical Research & Licensing CompanyInventor: Lawrence A. Smith, Jr.
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Patent number: 4299960Abstract: Propenimidates are provided having the formula: ##STR1## wherein X and Y are independently O or S; andR.sup.1 and R.sup.2 are independently C.sub.1 -C.sub.4 alkyl, (CH.sub.2).sub.n OR.sup.3 where R.sup.3 is C.sub.1 -C.sub.4 alkyl and n is 1 or 2, CH.sub.2 CH.sub.2 Cl, or CH.sub.2 CF.sub.3, provided that when R.sup.1 or R.sup.2 is CH.sub.2 CH.sub.2 Cl or CH.sub.2 CF.sub.3, then the respective X or Y is 0.Preferred propenimidates have X and Y as O and R' and R.sup.2 as methyl or ethyl.The propenimidates are made by preparing a monohydrohalide salt from a dihydrohalide salt of the formula: ##STR2## and then contacting the monohydrohalide salt with cyanamide. The propenimidates upon heating ring close to pyrimidines which are useful in preparing herbicidal compounds.Type: GrantFiled: April 24, 1980Date of Patent: November 10, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Julius J. Fuchs
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Patent number: 4275217Abstract: A chiral .alpha.-amino acid having a hydrogen substituent in a position alpha to the carboxylic function thereof is prepared by subjecting a corresponding optical antipode with a chiral amino acid to a strong base whereby the proton in a position alpha to the carboxylic function is removed and thereafter reacting the resulting product with a chiral protonation agent.Type: GrantFiled: July 9, 1979Date of Patent: June 23, 1981Assignee: Agence Nationale de Valorisation de la Recherche (ANVAR)Inventors: Lucette Duhamel, Jean-Christophe Plaquevent