Preparing Directly From Organic Acid, Acid Halide Or Salt Patents (Class 564/394)
  • Patent number: 9017638
    Abstract: Disclosed is a method for producing graphene functionalized at its edge positions of graphite. Organic material having one or more functional groups is reacted with graphite in reaction medium comprising methanesulfonic acid and phosphorus pentoxide, or in reaction medium comprising trifluoromethanesulfonic acid, to produce graphene having organic material fuctionalized at edges. And then, high purity and large scaled graphene and film can be obtained by dispersing, centrifugal separating the functionalized graphene in a solvent and reducing, in particular heat treating the graphene. According to the present invention graphene can be produced inexpensively in a large amount with a minimum loss of graphite. (FIG.
    Type: Grant
    Filed: February 24, 2012
    Date of Patent: April 28, 2015
    Assignee: Unist Academy-Industry Research Corp
    Inventors: Jong Beom Baek, Eun Kyoung Choi, In Yup Jeon, Seo Yun Bae
  • Patent number: 8859813
    Abstract: The present invention relates to salts having uronium cations and to a process for preparing same comprising alkylating urea C(O)(NR2)2 using an ester ARo.
    Type: Grant
    Filed: August 21, 2012
    Date of Patent: October 14, 2014
    Assignee: Merck Patent GmbH
    Inventors: Nikolai (Myloka) Ignatyev, Urs Welz-Biermann, German Bissky, Helge Willner, Andriy Kucheryna
  • Publication number: 20130108540
    Abstract: Disclosed is a method for producing graphene functionalized at its edge positions of graphite. Organic material having one or more functional groups is reacted with graphite in reaction medium comprising methanesulfonic acid and phosphorus pentoxide, or in reaction medium comprising trifluoromethanesulfonic acid, to produce graphene having organic material fuctionalized at edges. And then, high purity and large scaled graphene and film can be obtained by dispersing, centrifugal separating the functionalized graphene in a solvent and reducing, in particular heat treating the graphene. According to the present invention graphene can be produced inexpensively in a large amount with a minimum loss of graphite.
    Type: Application
    Filed: February 24, 2012
    Publication date: May 2, 2013
    Inventors: Jong Beom Baek, Eun Kyoung Choi, In Yup Jeon, Seo Yoon Bae
  • Patent number: 8404897
    Abstract: Embodiments of methods for preparing 3-aminopicric acid from picric acid is described. In one embodiment, the method comprises combining lithium hydroxide, picric acid, and a first solvent to form a first solution, combining lithium hydroxide, hydroxylamine hydrochloride, and a second solvent to form a second solution, combining the first solution with the second solution to form a mixture, and cooling the mixture.
    Type: Grant
    Filed: November 3, 2010
    Date of Patent: March 26, 2013
    Assignee: Pacific Scientific Energetic Materials Company
    Inventors: John W. Fronabarger, Michael D. Williams
  • Patent number: 8334322
    Abstract: Drug substances comprising a pharmaceutically acceptable organic acid addition salt of amine containing pharmaceutically active compounds useful for the treatment of a therapeutic ailment administration and exhibiting prophylactic properties when employed in non-therapeutic administration.
    Type: Grant
    Filed: December 22, 2011
    Date of Patent: December 18, 2012
    Assignee: Pisgah Laboratories, LLC
    Inventors: David William Bristol, Clifford Riley King, Joseph Pike Mitchener, Jr., Vicki Haynes Audia
  • Publication number: 20120259048
    Abstract: An object of the present invention is to provide processes for producing a rubber anti-aging agent, a vulcanization accelerator and a modified natural rubber, by converting glucose into benzoic acid or a benzoic acid derivative by a microorganism or extracting benzoic acid or a benzoic acid derivative from a plant, converting the obtained benzoic acid or benzoic acid derivative into aniline or an aniline derivative and then making the rubber anti-aging agent, vulcanization accelerator or modified natural rubber with the aniline or aniline derivative.
    Type: Application
    Filed: June 18, 2012
    Publication date: October 11, 2012
    Inventor: Keitaro FUJIKURA
  • Publication number: 20110105800
    Abstract: Embodiments of methods for preparing 3-aminopicric acid from picric acid is described. In one embodiment, the method comprises combining lithium hydroxide, picric acid, and a first solvent to form a first solution, combining lithium hydroxide, hydroxylamine hydrochloride, and a second solvent to form a second solution, combining the first solution with the second solution to form a mixture, and cooling the mixture.
    Type: Application
    Filed: November 3, 2010
    Publication date: May 5, 2011
    Inventors: John W. FRONABARGER, Michael D. WILLIAMS
  • Publication number: 20100041920
    Abstract: The present invention relates generally to novel salt forms of R-(+)-N-propargyl-1-aminoindan (i.e. rasagiline base), to a compound of formula Ia, to processes for their preparation and isolation, and to pharmaceutical compositions comprising the same.
    Type: Application
    Filed: July 20, 2009
    Publication date: February 18, 2010
    Inventors: Stephen Benedict David Winter, Ernesto Duran Lopez, Monica Benito Velez
  • Patent number: 7468460
    Abstract: A method for producing unprotected or carbamate-protected amines of formulae (II) and (III) or R1—NH2 (II) or R1—NHCO2R2 (III) by reacting hydroxamic acids of formula (I) (R1 CONHOH) with a) alkylpliosphonic acid anhydrite's, b) alcohol R2OH and c) optionally with a base, at a temperature ranging from 100 to +120°C., wherein the hydroxainic acid (I) is produced prior to or during reacting (in situ) and R1 is an optionally substituted linear or branched C1-C12 alkyl radical, substituted C3-C10 cycloalkyl, alkenyl, aryl or heteroaryl radical and R2 is an open-chain, cyclic or branched allyl, aryl or C1 to C12-alkyl radicals, or aryloxy, allyloxy or alkoxy radical possibly substituted with open-chain, cyclic or branched C1 to C12-alkyl radicals.
    Type: Grant
    Filed: July 5, 2006
    Date of Patent: December 23, 2008
    Assignee: Archimica GmbH
    Inventors: Andreas Meudt, Claudius Boehm
  • Publication number: 20080221357
    Abstract: A method for producing unprotected or carbamate-protected amines of formulae (II) and (III) or R1—NH2 (II) or R1—NHCO2R2 (III) by reacting hydroxamic acids of formula (I) (R1CONHOH) with a) alkylphosphonic acid anhydrite's, b) alcohol R2OH and c) optionally with a base, at a temperature ranging from 100 to +120° C., wherein the hydroxamic acid (I) is produced prior to or during reacting (in situ) and R1 is an optionally substituted linear or branched C1-C12 alkyl radical, substituted C3-C10 cycloalkyl, alkenyl, aryl or heteroaryl radical and R2 is an open-chain, cyclic or branched allyl, aryl or C1 to C12-alkyl radicals, or aryloxy, allyloxy or alkoxy radical possibly substituted with open-chain, cyclic or branched C1 to C12-alkyl radicals.
    Type: Application
    Filed: July 5, 2006
    Publication date: September 11, 2008
    Inventors: Andreas Meudt, Claudius Boehm
  • Patent number: 7378555
    Abstract: The present invention is to prepare efficiently 2?-amino-5?-hydroxypropiophenone corresponding to the AB-ring part of camptothecin (CPT) skeleton and a tricyclic ketone corresponding to the CDE-ring part in order to provide efficiently CPT by the total synthesis, which is a starting material for irinotecan hydrochloride and various kinds of camptothecin derivatives, and to provide stably CPT and its derivatives.
    Type: Grant
    Filed: September 8, 2006
    Date of Patent: May 27, 2008
    Assignee: Kabushiki Kaisha Yakult Honsha
    Inventors: Takanori Ogawa, Hiroyuki Nishiyama, Miyuki Uchida, Seigo Sawada
  • Publication number: 20070255057
    Abstract: A method of nitrating a compound selected from the group consisting of is provided.
    Type: Application
    Filed: February 27, 2007
    Publication date: November 1, 2007
    Inventors: Miall Cedilote, Thomas Patrick Cleary, Pingsheng Zhang
  • Patent number: 7094928
    Abstract: This invention relates to an improved process for synthesizing (±)-2-Amino-N-[2-(2,5-dimethoxyphenyl]-2-hydroxyethyl acetamide monohydrochloride in good yield and in a cost effective manner from 1-(2,5-dimethoxyphenyl)-2-bromoethanone by reacting the same with hexamine in the presence of novel solvent system comprising Tetrahydrofuran and water. The resulting aminoethanone is acylated with haloacetylchloride and sodium acetate in acetone-water solvent system. This product is reduced selectively first with sodium borohydride and subsequently with stannous chloride. This product is converted in situ to the corresponding hydrochloride salt immediately after reduction on its own.
    Type: Grant
    Filed: August 21, 2002
    Date of Patent: August 22, 2006
    Assignee: Sanmar Specialty Chemicals Ltd.
    Inventors: Rajaram Sankara Subramanian, Venkatanathan Satagopan, Rajagopalan Srinivasan
  • Patent number: 6900245
    Abstract: The present invention relates to a pharmaceutical composition for treating or preventing obesity, comprising novel crystalline sibutramine methanesulfonate hemihydrate of formula (I).
    Type: Grant
    Filed: October 3, 2003
    Date of Patent: May 31, 2005
    Assignee: Hanmi Pharm. Co., Ltd.
    Inventors: Jae-Heon Lee, Gha-Seung Park, Jae-Cheol Lee, Han-Kyong Kim, Young-Kil Chang, Gwan-Sun Lee
  • Publication number: 20030229102
    Abstract: The present invention relates to a compound of formula (I) or a pharmaceutically acceptable salt thereof which is useful for the treatment of conditions associated with glutamate hypofunction, such as psychiatric and neurological disorders 1
    Type: Application
    Filed: November 15, 2002
    Publication date: December 11, 2003
    Inventors: James Allen Knobelsdorf, Timothy Alan Shepherd, Eric George Tromiczak, Hamideh Zarrinmayeh, Dennis Michael Zimmerman
  • Patent number: 6657085
    Abstract: A process for the preparation of aniline compounds of formula: wherein n and R are as defined in claim 1, by reacting nitro compounds of formula: wherein n and R are as defined, with hydrazine at elevated temperature in the presence of an aqueous base. The compounds of formula I are suitable as intermediates in the preparation of herbicides of the isobenzofuranone type.
    Type: Grant
    Filed: November 15, 2002
    Date of Patent: December 2, 2003
    Assignee: Syngenta Crop Protection, Inc.
    Inventors: Gottfried Seifert, Thomas Rapold
  • Patent number: 6552228
    Abstract: The present invention relates to a process for the treatment of an aryl carbamoyl fluoride comprising in its molecule at least one perhalogenated aliphatic carbon, which carbon carries at least one halogen atom to be exchanged with fluorine. This process comprises the stage of bringing the said carbamoyl fluoride into contact with hydrofluoric acid, the ratio of hydrofluoric [lacuna] to carbamoyl fluoride being maintained during the reaction at a value at least equal to 4, preferably to 5, and characterized in that the said ratio is at most equal to 11. Application to organic synthesis.
    Type: Grant
    Filed: July 5, 2000
    Date of Patent: April 22, 2003
    Assignee: Rhodia Chimie
    Inventors: Gilbert Guidot, Christophe Rochin, Laurent Saint-Jalmes
  • Patent number: 6476266
    Abstract: Provided is a diamino compound suitable for obtaining a polyimide which can form a liquid crystal alignment film capable of providing a liquid crystal display element, an intermediate therefor and a production process for the same. The above production process is characterized by reacting a cyclohexylbenzene derivative represented by Formula (3): with an acid halide represented by Formula (4): by the Frieldel-Crafts reaction to produce a cyclohexylphenylcarbonyl compound, and reducing the above compound after nitrating, whereby a compound represented by Formula (1) is obtained: (wherein A1 represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms; A2 represents a single bond or an alkylene group having 1 to 5 carbon atoms, and one or optional methylene groups which are not adjacent in the group may be substituted with an oxygen atom; X is Br or Cl; m represents an integer of 0 to 3, and n represents an integer of 1 to 5).
    Type: Grant
    Filed: December 23, 1999
    Date of Patent: November 5, 2002
    Assignee: Chisso Corporation
    Inventors: Takahiro Mori, Toshiya Sawai, Shizuo Murata, Masaaki Yazawa, Satoshi Tanioka, Kumiko Hara
  • Patent number: 6448446
    Abstract: An improved synthesis of N,N,-disubstituted-p-phenylene-diamine (DSPDA) preferably di-n-butyl-p-phenylenediamine is disclosed. The improvement rests on the discovery that DSPDA and its salts are extremely sensitive to oxygen so that once the product DSPDA or its salt is formed, oxygen must be excluded from all manipulations.
    Type: Grant
    Filed: January 12, 2001
    Date of Patent: September 10, 2002
    Assignee: AntiCancer, Inc.
    Inventors: Li Tang, Yuying Tan
  • Patent number: 6444851
    Abstract: The invention provides a process for the preparation of 2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide of the formula 1 by hydrogenolysis of substituted 2-dibenzylamino-N-[2-(2′,5′-dimethoxyphenyl)-2-hydroxy-ethyl]acetamide having the formula (5), wherein Ar and Ar′ are aryl groups,
    Type: Grant
    Filed: January 9, 2002
    Date of Patent: September 3, 2002
    Assignee: Chemagis Ltd.
    Inventors: Michael Brand, Ronit Chen, Deby Yigal, Joseph Kaspi
  • Patent number: 6403833
    Abstract: The present invention provides a single step process for the preparation of p-aminophenol by hydrogenation of nitrobenzene in presence of an aqueous acid over a mono or bimetallic nickel catalyst at a temperature in the range of 80-120° C. for a period of 1 to 4 hrs. The resulting reaction mixture is extracted with an organic solvent like ethyl acetate, cyclohexane or toluene to separate the aqueous layer containing PAP and neutralizing it with ammonia solution to recover the solid p-aminophenol.
    Type: Grant
    Filed: January 30, 2001
    Date of Patent: June 11, 2002
    Assignee: Council of Scientific and Industrial Research
    Inventors: Chandrashekhar Vasant Rode, Manisha Jagdeeshrao Vaidya, Raghunath Vitthal Chaudhari
  • Patent number: 6169187
    Abstract: The invention provides a process for the recovery of ascorbic acid from a feed containing at least one precursor of ascorbic acid comprising converting the precursor into at least one product, the at least one product being ascorbic acid in an organic extractant composition, the organic extractant composition comprising at least one secondary or tertiary alkyl amine in which the aggregate number of carbon atoms is at least 20, as a primary extractant, and a polar extraction enhancer compound; wherein the extractant composition comprises at least 2 moles of the polar extraction enhancer compound per one mole of primary extractant; and subjecting the ascorbic acid-containing organic extractant composition to a stripping operation with aqueous solution at a temperature of at least 20° C. higher than the temperature at which the conversion is carried out; whereby there is obtained an aqueous solution of ascorbic acid in which the concentration of ascorbic acid is higher than 5%.
    Type: Grant
    Filed: August 9, 1999
    Date of Patent: January 2, 2001
    Assignee: Yissum Research Development Company of the Hebrew University of Jerusalem
    Inventor: Aharon Meir Eyal
  • Patent number: 6121491
    Abstract: Process for the preparation of cericlamine which consists: i) in arylating methacrylic acid with the diazonium chloride of 3,4-dichloroaniline, to obtain (+/-)2-chloro-3-(3,4-dichlorophenyl)-2-methylpropionic acid, ii) in aminating the acid with dimethylamine, to obtain (+/-)3-(3,4-dichlorophenyl)-2-dimethylamino-2-methylpropionic acid, or an alkaline metal salt thereof, iii) in esterifying the amino-acid or its salt, then, iv) in reducing the ester by a metal or organometal hydride to obtain (+/-)3-(3,4-dichlorophenyl)-2-dimethylamino-2-methyl-propan-1-ol.
    Type: Grant
    Filed: December 20, 1999
    Date of Patent: September 19, 2000
    Assignee: Warner-Lambert Company
    Inventors: Marc Nicolas, Blandine Laboue, Dominique Depernet
  • Patent number: 5847217
    Abstract: 2-Amino-5-alkyl-phenols, which are suitable as intermediates in the production of crop-protection agents or photographic couplers, can be prepared by subjecting 2-amino-5-alkyl-benzenesulphonic acids or their salts to alkaline hydrolysis.
    Type: Grant
    Filed: December 2, 1997
    Date of Patent: December 8, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Behre, Guido Steffan
  • Patent number: 5693863
    Abstract: The present invention relates to methods for the production of E-1-?4'-(2-dimethylaminoethoxy)-phenyl!-1-(3'-hydroxyphenyl)-2-phenyl-1-bu tene of formula (I) which comprises heating the compound of formula (II) in the presence of an organic solvent and HCl gas and cooling the reaction to obtain the compound of formula (IIIa), and then heating the isolated compound of formula (IIIa) in the presence of sulfuric acid or hydrochloric acid to obtain the compound according to formula (I).
    Type: Grant
    Filed: September 23, 1996
    Date of Patent: December 2, 1997
    Assignee: Klinge Pharma GmbH
    Inventors: Helmut Grill, Axel Woschina
  • Patent number: 5672753
    Abstract: .alpha.-oximino carboxylic acids or their esters are reduced with an alkali boron hydride and hydrogen chloride or sulfuric acid to yield racemic amino alcohols (e.g. (RS)-tert-leucinol).
    Type: Grant
    Filed: February 21, 1996
    Date of Patent: September 30, 1997
    Assignee: Degussa Aktiengesellschaft
    Inventors: Karlheinz Drauz, Wilfried Jahn, Michael Schwarm
  • Patent number: 5486609
    Abstract: A process for preparing carbocyclic m-aminohydroxyaromatics comprises reacting the corresponding o-- or m-halohydroxyaromatics or metal salts thereof with primary or secondary amines in the presence of a base and in the presence or absence of a diluent.
    Type: Grant
    Filed: March 24, 1995
    Date of Patent: January 23, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Robert Reinhardt, Helmut Reichelt, Roland Merger
  • Patent number: 5471002
    Abstract: A process for preparing trifluoromethylanilines of the formula (I), ##STR1## in which R.sup.1 and R.sup.2, independently of each other, are hydrogen, halogen, (C.sub.1 -C.sub.4) alkyl, hydroxyl, alkoxy, alkylthio, carboxyl, or a nitro or cyano group, by reacting compounds of the formula (II) ##STR2## in which X.sub.1, X.sub.2 and X.sub.3 are in each case, identically or differently, halogen atoms,a is 0 or 1,Y is fluorine, chlorine or bromine, andR.sup.1 and R.sup.2 have the defined meaning, with anhydrous hydrofluoric acid, and converting the resulting aniline hydrofluorides with a base into the free amines.
    Type: Grant
    Filed: August 18, 1994
    Date of Patent: November 28, 1995
    Inventors: Wolfgang Appel, Gunter Siegemund
  • Patent number: 5430188
    Abstract: A process for the preparation of 2-alkyl-6-methyl-N(1'-methoxy-2'-propyl)-aniline by catalytic reductive alkylation wherein at least one mole equivalent of methoxyacetone is reacted with one mole equivalent of 2-alkyl-6-methyl-aniline in a liquid medium without an additional solvent, in the presence of a platinized carbon catalyst and hydrogen and in the presence of an acid cocatalyst under a hydrogen pressure of between 2.times.10.sup.5 and 1.times.10.sup.6 Pa at a temperature between 20.degree. and 80.degree. C., characterized in that the reaction mixture contains water from the beginning of the reaction and after the hydrogenation, base is added, the reaction mixture is filtered to separate the catalyst and the title compound recovered from the filtrate. The process is particularly useful for the preparation of N-substituted chloracetanilide herbicides.
    Type: Grant
    Filed: December 15, 1993
    Date of Patent: July 4, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Bader, Peter Flatt, Paul Radimerski
  • Patent number: 5354891
    Abstract: 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: Grant
    Filed: March 4, 1993
    Date of Patent: October 11, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Tatsuhiko Obayashi
  • Patent number: 5326911
    Abstract: Ortho-amides of the formula ##STR1## can be prepared by reacting salts of the formula ##STR2## with alcoholates of the formulaM.sup.1 OR.sup.1 (III)where the radicals R.sup.1 to R.sup.4, M.sup.1 and X.sup..crclbar. have the meaning given in the description. The alcoholates are employed in highly active form with an effective content of 98-100% M.sup.1 OR.sup.1.
    Type: Grant
    Filed: July 20, 1992
    Date of Patent: July 5, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz-Ulrich Blank, Helmut Kraus, Gerhard Marzolph, Nikolaus Muller
  • Patent number: 5214170
    Abstract: A novel 1.alpha. (or 24R), 25-dihydroxy vitamin D.sub.3 amino acid derivative of the formula ##STR1## wherein R.sub.1 is OH or --O--CO--A--NH.sub.2, and R.sub.2 and R.sub.3 are each selected from the group consisting of hydrogen, OH and --O--CO--A--NH.sub.2 ; wherein one of R.sub.2 and R.sub.3 is hydrogen, one of R.sub., R.sub.2 and R.sub.3 is OH, and one of R.sub.1, R.sub.2 and R.sub.3 is --O--CO--A--NH.sub.2 ; and wherein A is C.sub.1-10 alkylene, is produced by removing a protective group for the amino group, e.g. 9-fluorenylmethyloxycarbonyl, in the presence of a base in an inert solvent. A radioisotope iodine-labeled residue is then attached to the amino group to produce a derivative useful in the assay of 1.alpha. (or 24R), 25-dihydroxy vitamin D.sub.3 in a specimen.
    Type: Grant
    Filed: January 27, 1992
    Date of Patent: May 25, 1993
    Assignee: Toyo Jozo Kabushiki Kaisha
    Inventors: Miyuki Tanabe, Shigeru Ikuta
  • Patent number: 5145958
    Abstract: 2,4- or 2,6-dihalogeno-aniline can be prepared by reacting an amino-benzoic acid ester of the formula ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 have the meanings indicated in the description, with 2-2.5 moles of a chlorinating or brominating agent in an inert reaction medium at a temperature of 40.degree.-160.degree. C. and subsequently hydrolyzing and decarboxylating the dihalogenated amino-benzoic acid ester.
    Type: Grant
    Filed: November 26, 1991
    Date of Patent: September 8, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfram Kissener, Helmut Fiege
  • Patent number: 5117018
    Abstract: A novel 1.alpha. (or 24R), 25-dihydroxy vitamin D.sub.3 amino acid derivative of the formula ##STR1## wherein R.sub.1 is OH or --O--CO--A--NH.sub.2, and R.sub.2 and R.sub.3 are each selected from the group consisting of hydrogen, OH and --O--CO--A--NH.sub.2 ; wherein one of R.sub.2 and R.sub.3 is hydrogen, one of R.sub.1, R.sub.2 and R.sub.3 is OH, and one of R.sub.1, R.sub.2 and R.sub.3 is --O--CO--A--NH.sub.2 ; and wherein A is C.sub.1-10 alkylene, is produced by removing a protective group for the amino group, e.g. 9-fluorenylmethyloxycarbonyl, in the presence of a base in an inert solvent. A radioisotope iodine-labeled residue is then attached to the amino group to produce a derivative useful in the assay of 1.alpha. (or 24R), 25-dihydroxy vitamin D.sub.3 in a specimen.
    Type: Grant
    Filed: October 5, 1989
    Date of Patent: May 26, 1992
    Assignee: Toyo Jozo Kabushiki Kaisha
    Inventors: Miyuki Tanabe, Shigeru Ikuta
  • Patent number: 5041563
    Abstract: A process for the manufacture of ascorbic acid from 2-ketogulonic acid esters (KGAE) utilizing amine salts of the latter is disclosed.
    Type: Grant
    Filed: May 22, 1990
    Date of Patent: August 20, 1991
    Assignee: Hoffman-La Roche Inc.
    Inventors: Peter Fahrni, Theodor Siegfried
  • Patent number: 4973758
    Abstract: The characteristic of the improved process for the preparation of 1,5-dihydroxynaphthalene and 1,5-diaminonaphthalene is to carry out the alkaline pressure hydrolysis of the disodium salt of naphthalene-1,5-disulphonic acid at temperatures from 270.degree. to 290.degree. C. and under 14 to 20 bar using an excess of sodium hydroxide solution such that the molar ratio NaOH/disodium salt of naphthalenesulphonic acid is at least 12:1. The 1,5-dihydroxynaphthalene which is obtained in this manner, without hazard and in substantially higher purity, is then aminated with ammonia in the presence of ammonium bisulphite to give 1,5-diaminonaphthalene, it being possible to achieve a further increase in the degree of purity of the 1,5-diaminonaphthalene by increasing the molar ratio NH.sub.3 /1,5-dihydroxynaphthalene to at least 6:1.
    Type: Grant
    Filed: November 21, 1989
    Date of Patent: November 27, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Behre, Lothar Jakob, Heinz U. Blank, Dietmar Mayer, Roland Busse
  • Patent number: 4964876
    Abstract: The dye mixture mentioned in claim 1 or one of the dyes mentioned in claims 12 or 13 are used for the dyeing of polyester textile material.
    Type: Grant
    Filed: May 18, 1989
    Date of Patent: October 23, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Christian Frey, Bernd Dill, Konrad Schmid
  • Patent number: 4855503
    Abstract: Oxybisaniline is prepared in high yield by reacting a hydroxylamine with a polycarboxylic diphenyl ether in the presence of an inorganic acid. The acid groups are directly converted to amine groups. By-products of the reaction are negligible.
    Type: Grant
    Filed: April 23, 1987
    Date of Patent: August 8, 1989
    Assignee: Amoco Corporation
    Inventors: Douglas E. Fjare, Gary P. Hagen
  • Patent number: 4748277
    Abstract: A process for the preparation of trifluoromethylanilines. Hydrolysis and exchange fluorination of a para-trihalomethyl benzene isocyanate or carbamyl halide are carried out in liquid hydrofluoric acid.
    Type: Grant
    Filed: September 25, 1986
    Date of Patent: May 31, 1988
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Michel Debois
  • Patent number: 4624937
    Abstract: An improved process is provided for the selective production of secondary amines and primary amines by bringing together under reaction conditions a tertiary amine or a secondary amine with oxygen or an oxygen-containing gas in the presence of an activated carbon catalyst, the improvement which comprises using an activated carbon catalyst wherein oxides have been removed from the surface of the carbon.
    Type: Grant
    Filed: February 28, 1985
    Date of Patent: November 25, 1986
    Assignee: Monsanto Company
    Inventor: Shine K. Chou
  • Patent number: 4506039
    Abstract: Polymer-containing polyether polyamines containing terminal aromatically-bound amino groups are produced by in situ polymerization of a polyether polyamine with an olefinically unsaturated monomer. The polyether polyamine starting material must have terminal aromatic amino groups, a molecular weight of from 800 to 10,000 and an aromatic amino group content of from 0.3 to 16 wt. %. Suitable olefinically unsaturated monomers include .alpha.,.beta.-unsaturated nitriles, aromatic vinyl compounds, .alpha.,.beta.-unsaturated carboxylic acids and esters thereof, vinyl esters, vinyl halides, vinylidene halides, .alpha.,.beta.-unsaturated carboxylic acid amides and aminoalkyl esters of unsaturated carboxylic acids. Acrylonitrile/styrene mixtures are preferred monomers. The starting materials are employed in quantities such that the product modified polyether polyamine contains from 1 to 60 wt. % polymer or graft-polymer. The product polyamines are particularly useful in the production of polyurethanes.
    Type: Grant
    Filed: December 20, 1982
    Date of Patent: March 19, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Balle, Werner Rasshofer, Winfried Schoberth
  • Patent number: 4481370
    Abstract: A method for the preparation of aromatic amines comprises reacting hydrogen fluoride with a phenyl carbamic fluoride.
    Type: Grant
    Filed: June 15, 1983
    Date of Patent: November 6, 1984
    Assignee: Occidental Chemical Corporation
    Inventors: Henry C. Lin, Byron R. Cotter
  • Patent number: 4363766
    Abstract: A process for the preparation of sulfur-containing N-benzyl-amino acids of the formula ##STR1## wherein X and Y, which may be identical to or different from each other, are each hydrogen or halogen;R.sub.1 is hydrogen or alkyl of 1 to 4 carbon atoms;R.sub.2 is hydrogen, alkyl of 1 to 3 carbon atoms, carboxy-lower alkyl or acyl;R.sub.3 is hydrogen or acyl; andn is 1 or 2;which comprises the steps of converting anthranilic acid or a halogenated anthranilic acid into the corresponding aldehyde, reacting the aldehyde with a compound of the formula ##STR2## wherein R.sub.1, R.sub.2 and n have the meanings previously defined, to form the corresponding Schiff's base, reducing the said Schiff's base, and recovering the reaction product.
    Type: Grant
    Filed: April 17, 1979
    Date of Patent: December 14, 1982
    Assignee: Boehringer Ingelheim GmbH
    Inventor: Bernard Bellegarde
  • Patent number: 4299983
    Abstract: A process for the production of symmetrical and unsymmetrical substituted diarylamines is disclosed. The process provides said diarylamines in high yield and purity by the reaction of a salt of an arylsulfonic acid and an alkali metal salt of a primary arylamine in the presence of an inorganic alkali metal salt.
    Type: Grant
    Filed: October 3, 1979
    Date of Patent: November 10, 1981
    Assignee: Xerox Corporation
    Inventors: Trevor I. Martin, John M. Lennon