Preparing Directly From An Amide (e.g., Preparing Directly From A Sulfenamide, Nitrosamine, Carboxamide, Thiourea, Etc.) Patents (Class 564/414)
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Patent number: 6552222Abstract: A process for the preparation of racemic amino acids, characterized in that an acylamino acid of the formula R1—CH(NH—CO—R2)COOH wherein R1 is hydrogen, a linear, branched or cyclic alkyl that has from 1 to 7 carbon atoms and that may contain substituents such as a hydroxyl, alkyloxy or alkylthio group; and R2 is a hydrogen atom or an alkyl having from 1 to 3 carbon atoms; is heated in the presence of water, in a pressure-resistant vessel, to a temperature in the range from 110° C. to 220° C. and is hydrolyzed.Type: GrantFiled: August 13, 2001Date of Patent: April 22, 2003Assignee: Degussa AGInventors: Klaus Huthmacher, Christoph Weckbecker, Horst Weigel
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Patent number: 6552229Abstract: Disclosed is a method for preparing a 4-nitroso-substituted aromatic amine that includes contacting an amide compound with a nitroaromatic compound in the presence of a base and a solvent to directly prepare 4-nitroso-substituted aromatic amine as a main product and 4-nitro-substituted aromatic amine as a by-product without producing 4-nitroso- or 4-nitro-substituted amide as an intermediate.Type: GrantFiled: July 31, 2002Date of Patent: April 22, 2003Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Young-J Joo, Jin-Eok Kim, Jeong-Im Won
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Patent number: 6479661Abstract: The invention relates to a method for disubstituting carboxylic acid amides on a geminal carbonyl-C-atom using a Grignard reagent in the presence of an organotitanate.Type: GrantFiled: March 23, 2001Date of Patent: November 12, 2002Assignee: Merck Patent GesellschaftInventors: Herwig Buchholz, Urs Welz-Biermann, Armin Meijere, Vladimir Chaplinski
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Patent number: 6462230Abstract: A method of decomposing wastes containing target compounds having one or more of hydrolyzable bonds of ether bond, ester bond, amide bond and isocyanate bond wherein the method comprises continuously supplying the wastes in a molten state or liquid state to a reactor, continuously supplying super-critical water or high pressure/high temperature water to the reactor, bringing the water into contact with the wastes, thereby decomposing the target compounds and then recovering them as raw material compounds or derivatives thereof for the target compounds. Target compounds contained in wastes in chemical plants which could not be utilized but merely incinerated or discarded so far are continuously decomposed into raw material compounds or derivatives thereof for the aimed compound and can be reutilized effectively.Type: GrantFiled: August 4, 2000Date of Patent: October 8, 2002Assignees: Kabushiki Kaisha Kobe Seiko Sho, Takeda Chemical Industries, Ltd.Inventors: Yoshiyuki Nagase, Ryuichi Fukuzato
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Patent number: 6448445Abstract: The invention relates to a method for disubstituting carboxylic acid amides on the geminal carbonyl-C-atom using at least one grignard reagent in the presence of a metal alcoholate compound used as a catalyst and in the presence of another organometallic compound used as a co-catalyst.Type: GrantFiled: February 23, 2001Date of Patent: September 10, 2002Assignee: Merck Patent Gesellschaft mit beschraenkter HaftungInventors: Herwig Buchholz, Urs Welz-biermann, Armin Meijere
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Patent number: 6429336Abstract: Residues from the distillation of a toluene diamine phosgenation mixture are hydrolyzed by mixing them with water and subjecting the mixture to a temperature of 200-350 ° C. The hydrolysis is performed in the presence of a sufficient amount of a base to maintain the pressure in the reactor to no more than a predetermined operating level. The product mixture is then extracted to recover TDA, which can be recycled. This provides an efficient process whereby nearly quantitative conversion of the residues to TDA can be achieved.Type: GrantFiled: May 5, 2000Date of Patent: August 6, 2002Assignee: The Dow Chemical CompanyInventors: Shenghong A. Dai, Duane S. Treybig, Kathryn Hock, Van A. Kent
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Patent number: 6262308Abstract: The invention relates to a process for preparing cis-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthylamine, or racemic sertraline, corresponding to formula (I) in salt form, starting with 4-(3,4-dichlorophenyl)tetralone of formula (II) according to which (a) the 4-(3,4-dichlorophenyl)tetralone of formula (II) is reacted with N-methylformamide in the presence of formic acid, (b) the reaction medium obtained according to (a) is treated with a base, and (c) the racemic sertraline salt is separated out by selective crystallization with an acid. The invention also relates to N-methylformamide-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthylamine and to its use to obtain racemic sertraline.Type: GrantFiled: March 29, 1999Date of Patent: July 17, 2001Assignee: CatalysInventor: Patrick Bigot
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Patent number: 6255529Abstract: A method of decomposing wastes containing target compounds having one or more of hydrolyzable bonds of ether bond, ester bond, amide bond and isocyanate bond wherein the method comprises continuously supplying the wastes in a molten state or liquid state to a reactor, continuously supplying super-critical water or high pressure/high temperature water to the reactor, bringing the water into contact with the wastes, thereby decomposing the target compounds and then recovering them as raw material compounds or derivatives thereof for the target compounds. Target compounds contained in wastes in chemical plants which could not be utilized but merely incinerated or discarded so far are continuously decomposed into raw material compounds or derivatives thereof for the aimed compound and can be reutilized effectively.Type: GrantFiled: January 16, 1997Date of Patent: July 3, 2001Assignees: Kabushiki Kaisha Kobe Seiko Sho, Takeda Chemical Industries, Ltd.Inventors: Yoshiyuki Nagase, Ryuichi Fukuzato
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Patent number: 6245943Abstract: A disclosed method of preparing p-phenylenediamine includes the steps of: reacting urea and nitrobenzene with a base in the presence of a polar solvent to yield 4-nitrosoaniline and 4-nitroaniline; and subsequently, diluting the resulting mixed solution in an alcohol and performing hydrogenation using a catalyst, thereby providing highly pure p-phenylenediamine destitute of an ortho- or meta-isomer as a byproduct. The method has some advantages in that: the process is simplified in such a manner that the hydrogenation is performed in the presence of the hydrogenation catalyst in a single reactor (i.e., one pot) without a need of isolating 4-nitrosoaniline or purifying the product; inexpensive urea and an alkali base are used to reduce the production cost; and 4-nitrosoaniline is formed as an intermediate to yield p-phenylenediamine with a high selectivity, thereby requiring no purification process after isolation of the product.Type: GrantFiled: August 16, 2000Date of Patent: June 12, 2001Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Young J. Joo, Jin Eok Kim, Jeong Im Won
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Patent number: 6198001Abstract: A method for preparing 4-nitrosoaniline, including reacting urea and nitrobenzene in a polar organic solvent in the presence of a base at a temperature of room temperature to 150° C. The method uses a relatively cheap urea and nitrobenzene as the raw materials, and also a relatively cheap base, thereby decreasing the manufacturing cost. Urea used as an amine donor is excellent in a reactivity to nitrobenzene, and a reaction intermediate is unstable as compared with 4-(4-nitrophenyl)benzamide to easily decompose into 4-nitroaniline and 4-nitrosoaniline. This allows a reaction time and a process time to be shortened. Moreover, the method is advantageous in that waste hazardous to the environment is not produced as a byproduct.Type: GrantFiled: March 15, 2000Date of Patent: March 6, 2001Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Young J. Joo, Jin-Eok Kim, Jeong-Im Won, Kum-Ui Hwang
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Patent number: 6156932Abstract: A method for preparing 4,4'-dinitrodiphenylamine, including reacting urea and nitrobenzene in a polar organic solvent in the presence of a base at a temperature of room temperature to 100.degree. C. The method employs a relatively cheap urea and nitrobenzene as the raw materials, and also employs a relatively cheap base, thereby decreasing the manufacturing costs. Moreover, the method does not produce by-products, thus eliminating a need for a post-treating process. Additionally, the method is advantageous in that the production of 4,4'-dinitrodiphenylamine can be achieved in high yield and selectivity even under non-intensive reaction conditions by appropriately controlling the amounts of urea and nitrobenzene.Type: GrantFiled: February 23, 2000Date of Patent: December 5, 2000Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Young J. Joo, Jin-Eok Kim, Jeong-Im Won, Kum-Ui Hwang
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Patent number: 5965735Abstract: Process for preparing a key intermediate, 2-methyl-3-trifluoromethylaniline (MTA) of Flunixin, as well as novel intermediates thereof are described.Type: GrantFiled: May 23, 1995Date of Patent: October 12, 1999Assignee: Schering CorporationInventors: Henry J. Doran, Donal J. Coveney
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Patent number: 5929265Abstract: Binuclear iridium (I) phosphine complexes of the general formula: ##STR1## in which X is fluorine, chlorine, bromine or iodine, and ##STR2## is in each case a chiral bidentate diphosphine ligand. The complexes are particularly suitable as catalysts for the inter- or intramolecular asymmetric hydroamination of prochiral olefins.Type: GrantFiled: October 13, 1998Date of Patent: July 27, 1999Assignee: Lonza AGInventors: Romano Dorta, Patrick Egli, Nikolaus H Bieler, Antonio Togni, Martin Eyer
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Patent number: 5906998Abstract: In the decomposition of a polymer containing a urethane linkage and/or urea linkage in the presence of a decomposing agent, the amount of evolved carbon dioxide is measured and the decomposition reaction is conducted until a total amount of evolved carbon dioxide reaches a specified value to obtain a liquid decomposition product. According to the present invention, a decomposition product having constant quality can be obtained in a simple manner.Type: GrantFiled: August 20, 1996Date of Patent: May 25, 1999Assignees: Sumitomo Bayer Urethane Co., Inc., Toyota Jidosha Kabushiki KaishaInventors: Yuji Hoshino, Takaaki Masuda, Hiroshi Ikuta, Hisao Mitobe
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Patent number: 5892118Abstract: A process for producing 4,6-diaminoresorcinols comprises the steps of:subjecting a dioxime of the formula (4) ##STR1## wherein R is an alkyl or phenyl group, to Beckmann rearrangement to thereby produce 4,6-diacylaminoresorcinol of the formula (5) ##STR2## wherein R is as defined above, and subjecting the 4,6-diacylaminoresorcinol to hydrolysis and recovering the product 4,6-diaminoresorcinol (6) ##STR3## or a salt thereof.Type: GrantFiled: October 8, 1997Date of Patent: April 6, 1999Assignee: Daiwa Kasei Industry Co., Ltd.Inventors: Junji Kawachi, Hironori Matsubara, Yoshinori Nakahara, Yutaka Watanabe
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Patent number: 5728873Abstract: A process for the preparation of cyclopropanamine by Hofmann degradation of cyclopropanecarboxamide, comprising the following steps:(1) suspending cyclopropanecarboxamide, either (A) in 1.1 to 4 mol of sodium hydroxide, in solution whose concentration is 10 to 50%, per mol of amide, or (B) in a sparing amount of water,(2) adding 1 to 1.5 mol of hypochlorite, per mol of amide, from a 5 to 15% strength hypochlorite solution at a temperature of 0.degree. to 20.degree. C.,(3) adding 1.1 to 4 mol of sodium hydroxide, in solution whose concentration is 10 to 50%, per mol of amide, in the case where a suspension has been formed according to step (1)(B),(4) reacting the amide, hypochlorite, and sodium hydroxide for 10 to 60 minutes to form a homogeneous reaction mixture,(5) continuously passing the homogeneous reaction mixture through a tubular reactor at a temperature of 45.degree. to 260.degree. C.Type: GrantFiled: June 14, 1996Date of Patent: March 17, 1998Assignee: Huels AktiengesellschaftInventors: Wolfgang Kleemiss, Thomas Kalz
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Patent number: 5672754Abstract: The invention relates to a process for the preparation of compounds of formula ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl or sulfo, and R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl, which process comprises reacting a compound of formula ##STR2## wherein Hal is halogen and R.sub.1 has the meaning given above, with a compound of formula ##STR3## wherein Y is a saponifiable group and R.sub.2 has the meaning given above, to give the compound of formula ##STR4## wherein R.sub.1, R.sub.2 and Y have the meanings given above, and saponifying the compound of formula (4) to give the compound of formula (1).The compounds of formula (1) are suitable for the synthesis of dyes.Type: GrantFiled: September 15, 1995Date of Patent: September 30, 1997Assignee: Ciba-Geigy CorporationInventor: Guido Jordine
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Patent number: 5659084Abstract: Processes for preparing 2-substituted benzaldehydes of general formula (I), wherein: R.sub.1 is CH.sub.2 CH.sub.2 --(L.sub.1).sub.p --(CH.sub.2).sub.q --(L.sub.2).sub.r --CH.sub.2 --(T).sub.2 --Z; L.sub.1 and L.sub.2 are independently CH.sub.2 CH.sub.2, CH.dbd.CH or C.tbd.C; q is 0 to 8; p, r and s are independently 0 or 1; T is O, S, CH.sub.2, CH.dbd.CH, C.tbd.C; and Z is C.sub.1-4 alkyl, ethynyl, trifluoromethyl, isopropenyl, furanyl, thienyl, cyclohexyl or phenyl optionally mono substituted with CF.sub.3, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, methylthio, or trifluoromethylthio; and R.sub.2 and A are independently H, CF.sub.3, C.sub.1-4 alkyl, F, Cl, Br or I; are useful for preparing pharmaceutically active compounds.Type: GrantFiled: December 7, 1994Date of Patent: August 19, 1997Assignees: SmithKline Beecham Corporation, SmithKline Beecham plcInventors: Kerry Joseph Gombatz, Michael Anthony Forth, Jerome Francis Hayes, Michael Barry Mitchell, Stephen Alexander Smith
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Patent number: 5659075Abstract: A process is claimed for preparing [1S(1(.alpha., 2.beta., 4.beta.)]-4-amino-2-hydroxymethyl -1-cyclopentanol from cis-4-((R)-benzoylamino)-2-cyclopentenecarboxylic acid, methyl ester in five steps. The invention also describes a number of novel intermediates useful in the synthesis of [1S(1.alpha., 2.beta.,4.beta.)]-4-amino-2-hydroxymethyl-1-cyclopentanol.Type: GrantFiled: April 6, 1995Date of Patent: August 19, 1997Assignee: Glaxo Group LimitedInventors: Bernard Charles Halter, Clive Alwin Meerholz, Mark Brian Schilling, David Joszef Tapolczay, John Peter Turnbull
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Patent number: 5633407Abstract: A process for preparing substituted aromatic azo compounds is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic azo compounds are further reacted with a nucleophilic compound in the presence of a suitable solvent system, a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 to produce a substituted aromatic amine.Type: GrantFiled: May 18, 1995Date of Patent: May 27, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, Brian K-M Cheng
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Patent number: 5618979Abstract: A process for preparing substituted aromatic amines which comprises contacting a nucleophilic compound and a substituted aromatic azo compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the substituted aromatic azo compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.Type: GrantFiled: May 18, 1995Date of Patent: April 8, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, Brian K-M Cheng
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Patent number: 5597940Abstract: Disclosed is a process for producing .beta.-nitroenamine represented by the formula I: ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and independently indicate a hydrogen atom or a C.sub.1 -C.sub.10 alkyl group which may be optionally substituted with at least one group selected from the group consisting of a halogen atom, a lower alkoxy group, an aryloxy group, a hydroxyl group or an aryl group, or an aryl group which may be optionally substituted with a halogen atom, a lower alkyl group, a lower alkoxy group, an aryl group, an aryloxy group, a nitro group, a cyano group, an acylamino group, a di-lower alkylamino group, an arylamino group, a hydroxyl group, an arylsulfonyl group, a mercapto group, a lower alkylthio group or an arylthio group, R.sub.1 and R.sub.2 may bond together to form a cycloalkyl or bicycloalkyl and R.sub.3 is a hydrogen atom, a lower alkyl group, a cycloalkyl group or an aralkyl group; and an intermediate for producing the .beta.-nitroenamine.Type: GrantFiled: March 9, 1995Date of Patent: January 28, 1997Assignee: Sumitomo Chemical Company, LimitedInventor: Shinzo Seko
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Patent number: 5521317Abstract: There is disclosed a process for the preparation of an indanylamine compound of general formula ##STR1## wherein R.sup.1 represents an optionally substituted alkyl group, and R.sup.2, R.sup.3 and R.sup.4 independently represent a hydrogen atom or an optionally substituted alkyl group, the process including the steps of hydrogenating a compound of general formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as described above and R.sup.5 and R.sup.6 independently represent a halogen atom, a hydroxyl, nitro or cyano group, or an optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylcarboxy or alkylamino group provided that R.sup.5 and R.sup.6 represent different atoms or groups, and subsequent rearrangement and derivatization of the product thereof. Compounds of general formula I may be used to prepare preferred stereoisomers of fungicidal N-indanyl carboxamide compounds.Type: GrantFiled: October 12, 1994Date of Patent: May 28, 1996Assignee: American Cyanamid Co.Inventor: Paul H. Briner
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Patent number: 5516943Abstract: A two-step process for the conversion of a trans-1-amino-2-hydroxycycloalkane stereoselectively to a cis-1-amino-2-hydroxycycloalkane is disclosed. The novel step, a one-step hydrolysis with formal inversion, can be used to convert an amide of a trans-1-amino-2-hydroxycycloalkane to a cis-1-amino-2-hydroxycycloalkane. Methods for obtaining the trans-1-amino-2-hydroxycycloalkanes and their amides from alkenes are also disclosed. A preferred process converts indene to cis-1-amino-2-indanol.Type: GrantFiled: September 14, 1993Date of Patent: May 14, 1996Assignee: Sepracor, Inc.Inventors: Yun Gao, Yaping Hong, Xiaoyi Nie, Roger P. Bakale, Richard R. Feinberg, Charles M. Zepp
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Patent number: 5484931Abstract: Process for preparing a key intermediate, 2-methyl-3-trifluoromethylaniline (MTA) of Flunixin, as well as novel intermediates thereof are described.Type: GrantFiled: June 15, 1994Date of Patent: January 16, 1996Assignee: Schering CorporationInventors: Henry J. Doran, Donal J. Coveney
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Patent number: 5475139Abstract: This invention provides a novel process for the preparation of substituted derivatives of diphenyl amine. The special feature of this novel process is that low cost and recoverable phenolic salts are used as catalysts for molecular rearrangement and aminolysis to obtain substituted derivatives of diphenyl amine in high yield.Type: GrantFiled: October 22, 1993Date of Patent: December 12, 1995Assignee: Yung Shin Pharm. Ind. Co., Ltd.Inventors: Fangchen Lee, Tsung-Chung Liu
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Patent number: 5475140Abstract: 4-Amino-3-methyl-N-ethyl-N-(.beta.-hydroxyethyl)-aniline sulfate which is used particularly as a developer for color photography can be easily produced in high yield and high quality by nitrosating N-ethyl-N-(.beta.-hydroxyethyl)-m-toluidine by use of an alkyl nitrite in a homogeneous alcohol solution containing sulfuric acid in an amount of about 0.5 to about 1 mole per mole of N-ethyl-N-(.beta.-hydroxyethyl)-m-toluidine, and then reducing the nitrosation product in an aqueous alcohol solution after or without isolation of the nitrosation product.Type: GrantFiled: April 19, 1994Date of Patent: December 12, 1995Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Takehiko Iritani, Ryohiko Kinoshita, Yoshiki Kametani
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Patent number: 5463129Abstract: The present invention relates to a method of cleaving arylethers such as arylethers represented by the formula: ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.6 alkyl, cycloalkyl, phenyl, substituted phenyl or CH.dbd.CH.sub.2 ; each A is independently NO.sub.2, hydroxy, halo, or methoxy; n is an integer from 0 to 5; and x is 1 or 2, comprising contacting the arylether with an amide hydrohalide salt under conditions sufficient to cleave the ether group(s) of the arylether and form a phenol or substituted phenol. The present invention also relates to a method of preparing 4,6-diaminoresorcinol, which is a monomer used for making polybenzoxazoles (PBO).Type: GrantFiled: December 23, 1993Date of Patent: October 31, 1995Assignee: The Dow Chemical CompanyInventors: Zenon Lysenko, Richard G. Pews
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Patent number: 5451702Abstract: A process for preparing substituted aromatic amines is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 and reducing the product of the reaction of the nucleophilic compound and the azo containing compound under conditions which produce the substituted aromatic amine. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.Type: GrantFiled: April 26, 1993Date of Patent: September 19, 1995Assignee: Monsanto CompanyInventors: Michael K. Stern, Brian K-M Cheng
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Patent number: 5430189Abstract: An arylisonitrosoalkanone is hydrogenated in the presence of a noble metal catalyst and a weak carboxylic acid to form an arylalkanolamine which is then hydrogenated in the presence of a strong mineral acid and the transition metal catalyst to form an arylalkylamine. When the arylisonitrosoalkanone is an isonitrosoacetophenone, the isonitrosoacetophenone is prepared by one of two methods.In the first method, a substituted or an unsubstituted isonitrosoacetophenone is prepared from a corresponding substituted or unsubstituted acetophenone by oxidizing the acetophenone to form a substituted or an unsubstituted phenylglyoxalacetal in a reactor, hydrolyzing the phenylglyoxal acetal in the same reactor to form a corresponding substituted or unsubstituted phenylglyoxal, and condensing the phenylglyoxal with hydroxylamine or a salt thereof in the same reactor to form the substituted or unsubstituted isonitrosoacetophenone.Type: GrantFiled: January 19, 1994Date of Patent: July 4, 1995Assignee: Hoechst Celanese CorporationInventors: Joseph A. McDonough, Ahmed M. Tafesh, Olan S. Fruchey
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Patent number: 5410082Abstract: Process for preparing amines by reacting amides in aqueous-alkaline solutions and/or suspensions with halogens or hypohalites in the presence of alcohols, and converting the reaction products into the amines by hydrolysis, hydrogenation or reductive methods.Type: GrantFiled: May 9, 1994Date of Patent: April 25, 1995Inventor: Ralf Pfirmann
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Patent number: 5401882Abstract: The present invention is directed to a process for the preparation of deactivated anilines, which comprises the step of reacting a compound of formula (I) ##STR1## with a dialkylamide in the presence of a base at elevated temperature, in which:R.sub.1 is chosen from groups whose anions (R.sub.1.sup.-) constitute leaving groups;R.sub.2 and R.sub.4, which may be the same or different, are chosen from hydrogen, hydrocarbon chains, halogens and groups which are electron-attracting (EAG);R.sub.3 is chosen from hydrocarbon chains, halogens and groups which are electron-attracting, preferably through an inductive effect rather than a mesomeric effect; with the proviso that at least one of the groups R.sub.2, R.sub.3, and R.sub.4 is electron-attracting through an inductive effect.A second embodiment of the present invention is directed to a process for the dealkylation of deactivated anilines which comprises the steps of free radical halogenation of the benzyl carbon followed by hydrogenation.Type: GrantFiled: November 24, 1993Date of Patent: March 28, 1995Assignee: Rhone-Poulenc ChimieInventor: Jean-Marc Ricca
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Patent number: 5401878Abstract: A fluorine-containing polyimide having a low dielectric constant, low water absorption and excellent heat resistance and moisture resistance and a precursor thereof such as a fluorine-containing polyamide-acid, can be prepared by reacting an acid anhydride with an aromatic diamine having perfluoroalkyl group.Type: GrantFiled: September 1, 1993Date of Patent: March 28, 1995Assignee: Hitachi Chemical Company, Ltd.Inventors: Masami Yusa, Shinji Takeda, Yasuo Miyadera
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Patent number: 5354891Abstract: Disclosed is a method for producing aromatic amine derivatives in a high yield at a low price, which comprises inducing an aromatic hydroxamic acid derivative to undergo a rearrangement reaction under a mild condition in the presence of a base and a nitrile or a nitrile equivalent.Type: GrantFiled: March 4, 1993Date of Patent: October 11, 1994Assignee: Fuji Photo Film Co., Ltd.Inventor: Tatsuhiko Obayashi
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Patent number: 5331099Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting an amide and nitrobenzene in the presence of a suitable solvent system, and reacting the amide and nitrobenzene in the presence of a suitable base and a controlled amount of protic material at a suitable temperature in a confined reaction zone. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide starting material which can be recycled or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the amide starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.Type: GrantFiled: April 16, 1993Date of Patent: July 19, 1994Assignee: Monsanto CompanyInventors: Michael K. Stern, James K. Bashkin
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Patent number: 5283364Abstract: Polyamines containing primary amino groups are made by hydrolyzing an isocyanate with water in the presence of a solvent which is a carboxylic acid amide. The solvent must be used in a quantity of at least 10% by weight solvent based on 100% by weight of isocyanate. The weight ratio of solvent to water must be from 3 to 200. A homogeneous phase is maintained during the hydrolysis which is carried out at temperatures of from 20.degree. to 210.degree. C. A not incorporable basic and/or metal catalyst particularly alkali metal hydroxides may be employed. The polyamines produced by this process are particularly useful for the production of polyurethanes.Type: GrantFiled: January 15, 1993Date of Patent: February 1, 1994Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Klaus Konig, Hans-Joachim Meiners, Gerhard Grogler
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Patent number: 5248781Abstract: Substituted anilino-nicotinic acid derivatives are readily prepared from the condensation of two intermediates, 2-alkyl-3-perfluoroalkyl-anilines and alkyl 2-chloronicotinates. The 2-alkyl-3-perfluoroalkyl-aniline intermediate can be prepared via a novel three step synthesis. 3-Perfluoroalkyl-anilines are reacted with an amine directing protecting group reagent to protect the amine. The protected amine is then alkylated, and finally, the directing group is removed to form the 2-alkyl-3-perfluoroalkyl-aniline intermediate. The 2-alkyl-3-perfluoroalkyl-aniline intermediate is condensed with the alkyl 2-chloronicotinate to form the anilino-nicotinic acid derivative.Type: GrantFiled: September 21, 1992Date of Patent: September 28, 1993Assignee: The Trustees of Princeton UniversityInventor: Alexander McKillop
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Patent number: 5221770Abstract: A process is disclosed for the preparation of 2-amino-5,6-dimethoxy-tetralin, which is a useful intermediate for the preparation of pharmacologically active chemical compounds.Type: GrantFiled: September 25, 1992Date of Patent: June 22, 1993Assignee: Zambon Group S.p.A.Inventors: Giorgio Bertolini, Cesare Casagrande, Francesco Santangelo
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Patent number: 5216042Abstract: A method of preparing viscosity-stabilized toluene diisocyanate distillation residues comprising contacting toluene diisocyanate distillation residue with a material suitable for purging chloride-containing vapors under reaction conditions suitable to remove chloride-containing vapors from the toluene diisocyanate distillation residues. The material may be, for example, an aromatic solvent and/or a gas which associates, physically, chemically, or a combination thereof, with the vapors but not with significant amount of other components that may be present in the toluene diisocyanate distillation residue. The viscosity-stabilized and reactive residue can then be used alone or blended with one or more other isocyanate products, such as polymeric methylene diphenylisocyanate, to prepare materials such as polyurethane, polyisocyanurate, polyurethane-polyurea or polyurea compositions including, for example, foams.Type: GrantFiled: July 10, 1991Date of Patent: June 1, 1993Assignee: The Dow Chemical CompanyInventors: Rory D. Daussin, Steven B. Lowenkron, John L. Nafziger
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Patent number: 5196601Abstract: Disclosed herein is a process for producing an alcohol or an amine by reducing a compound having a formyl, keto, nitro, oxirane, ester, nitrile, amide or halogenated carboxyl group with an alkali metal boro-hydride in the presence of a compound having a hydroxyl group and ether linkage. According to the present invention, a functional group having a great steric hindrance can be reduced, and a corresponding alcohol or amine can efficiently be produced under very mild conditions on an industrial scale.Type: GrantFiled: June 17, 1992Date of Patent: March 23, 1993Assignee: Kao CorporationInventors: Tomohito Kitsuki, Yoshiaki Fujikura
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Patent number: 5126485Abstract: A process for the hydrogenation of halogenonitro-aromatic compounds wherein said compounds are contacted with a nickel-, cobalt- or iron-based catalyst, preferably Raney nickel, and hydrogen in the presence of a sulfur-containing compound. Preferably, the sulfur-containing compound is a sulfoxide or sulfone, and the molar ratio of the sulfur-containing compound to the catalyst ranges from about 1:1 to 10:1.Type: GrantFiled: July 20, 1990Date of Patent: June 30, 1992Assignee: Rhone-Poulenc ChimieInventors: Rosemarie Bailliard, Georges Cordier, Jean-Michel Grosselin, Bernard Langlois, Laurent Gilbert, Gerard Forat
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Patent number: 5053543Abstract: Process for synthesizing 2-aminobenzophenones such as the following formula (I): ##STR1## wherein X.sup.1 and X.sup.2 are substituents and r and s are 1 or 2, by reacting an anthranilic acid amide e.g. an N-alkoxy-N-alkyl anthranilic acid amide, with a halobenzene in the presence of an alkyllithium reagent.Type: GrantFiled: November 28, 1990Date of Patent: October 1, 1991Assignee: Glaxo Inc.Inventors: Marty C. Johnson, Stephen V. Frye
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Patent number: 5041670Abstract: Methods of producing N-phenyl amines comprise reacting a phenyl-containing isocyanate with HR, and a boron complexing agent in an aprotic solvent, wherein R, is --OH or --COOH (i.e., water or formic acid), neutralizing the resulting N-aryl amide to N-aryl amine and recovering the N-aryl amine.Type: GrantFiled: March 29, 1988Date of Patent: August 20, 1991Assignee: Drexel UniversityInventors: Franklin A. Davis, William E. Starner
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Patent number: 5039801Abstract: The invention provides an improved method for obtaining optically active amines, carbamates, and isocyanates by thermal fragmentation of optically active ureas through refluxing the ureas in C.sub.3 -C.sub.7 alcohol solution with or without catalytic amounts of alkali metal.Type: GrantFiled: August 28, 1987Date of Patent: August 13, 1991Assignee: The United States of America as represented by the Department of Health & Human ServicesInventors: Arnold Brossi, Bernhard Schonenberger
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Patent number: 5032687Abstract: The present process for the preparation of cyclopropylamine by the so-called Hofmann degradation of cyclopropanecarboxamide is characterized in that the cyclopropanecarboxamide is employed in the form of a solution. The new process can be carried out at 5.degree.-35.degree. C. The cyclopropylamine is obtained after introducing the reaction mixture into a concentrated alkali metal hydroxide solution.Type: GrantFiled: October 18, 1989Date of Patent: July 16, 1991Assignee: Kernforschunganlage Julich Gesellschaft mit beschrankter Haftung.Inventors: Herbert Diehl, Heinz U. Blank, Edwin Ritzer
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Patent number: 5025107Abstract: Disclosed is a process for the preparation of bis-acylamido aromatic compounds by reacting certain arylene dihalides with certain arylene dihalides in the presence of a copper catalyst. The process may be utilized in the synthesis of arylenediamines.Type: GrantFiled: July 24, 1989Date of Patent: June 18, 1991Assignee: Eastman Kodak CompanyInventor: Kim S. Chamberlin
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Patent number: 5011997Abstract: This invention is an improved process for preparing 2,2-bis(4-aminophenyl)hexafluoropropane which comprises subjecting 2,2-bis(4-aminocarbonylphenyl)hexafluoropropane to the Hofmann reaction and then treating that reaction product under reducing conditions to produce the desired amine in high yield.Type: GrantFiled: October 7, 1987Date of Patent: April 30, 1991Assignee: Hoechst Celanese Corp.Inventors: James R. Hazen, William R. Lee
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Patent number: 4980505Abstract: The conversion of ortho-hydroxylated Mannich bases to the corresponding methylated compounds, e.g., cresols, can be effectively carried out using a novel hydrogenation technique.Type: GrantFiled: December 16, 1988Date of Patent: December 25, 1990Assignee: Clairol IncorporatedInventors: Yuh-Guo Pan, Lana L. Hochman
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Patent number: 4931595Abstract: Polyamines containing primary amino groups are prepared in a single stage process by hydrolyzing an isocyanate in the presence of a catalyst incorporable through an NCO reactive group and a water-miscible aprotic-dipolar solvent. This hydrolysis is carried out at from 20.degree. to 210.degree. C. with the reactants being in substantially homogeneous phase. The isocyanate starting material has an NCO content of from 0.5 to 40% by weight. The catalyst is used in a quantity of at least 0.0001% by weight, based on 100% by weight of isocyanate compound. The water-miscible solvent is used in a quantity of at least 10% by weight, based on 100% by weight of isocyanate compound. The polyamines thus produced are particularly useful in the production of polyurethanes.Type: GrantFiled: August 2, 1989Date of Patent: June 5, 1990Assignee: Bayer AktiengesellschaftInventor: Werner Rasshofer
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Patent number: 4883787Abstract: A process for preparing 2-acyl-3,4-dialkoxyanilines is described. The 2-acyl-3,4-dialkoxyanilines are useful intermediates in the preparation of 5,6-dialkoxy-4-alkyl-2(1H)-quinazolinones. The substituted quinazolinones are active as cardiotonic agents.Type: GrantFiled: June 20, 1988Date of Patent: November 28, 1989Assignee: Ortho Pharmaceutical CorporationInventors: Richard A. Conley, Donald L. Barton