Utilizing Nitryl Halide, Nitrosyl Halide, Hch=no- Or Hhno- (wherein Substitution May Be Made For Hydrogen Only; E.g., Oximes, Oxime Esters, Hydroxylamine Salts, Olefin-nitrosyl Chloride Adducts, Etc.) Patents (Class 558/314)
  • Publication number: 20150148558
    Abstract: The present invention provides a method for producing a nitrile represented by general formula (1) (in the formula, R denotes an optionally substituted alkyl group, alkenyl group, dienyl group, aralkyl group or aryl group having a total of 3-20 carbon atoms), and the method includes heating an aldoxime represented by general formula (2) (in the formula, R denotes the same groups as those mentioned above) at 80-250° C. in the presence of an alkali metal or alkaline earth metal salt of phosphoric acid (catalyst A) and distilling off water generated as the reaction progresses to outside the reaction system.
    Type: Application
    Filed: May 20, 2013
    Publication date: May 28, 2015
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Kenji Yagi, Kenya Ishida
  • Publication number: 20020120163
    Abstract: A process for producing cyclopropanecarbonitrile involves reacting cyclopropanecarbaldoxime with acetic anhydride to obtain a mixture containing acetic acid and cyclopropanecarbonitrile. The acetic acid can be removed from the mixture through azeotropic distillation of acetic acid with a solvent that forms with acetic acid an azeotropic mixture having an azeotropic point lower than the boiling point of the cyclopropanecarbonitrile.
    Type: Application
    Filed: February 25, 2002
    Publication date: August 29, 2002
    Applicant: KURARAY CO. LTD
    Inventors: Tatsuhiko Hayashibara, Junko Sato, Eriko Matsuda, Masahiro Torihara, Yoshin Tamai
  • Patent number: 6433195
    Abstract: The present invention provides a production method of a 5-phthalancarbonitrile compound of the formula [VI] as well as production methods of a compound of the formula [V]
    Type: Grant
    Filed: November 30, 2001
    Date of Patent: August 13, 2002
    Assignee: Sumika Fine Chemicals Co., Ltd.
    Inventors: Tetsuya Ikemoto, Masami Igi
  • Patent number: 6417400
    Abstract: The present invention relates to: a) methylbiphenyl derivatives of general formula: in which R1 represents OH, C3-C7 alkyl or C3-C7 cycloalkyl, these compounds being in the form of individual isomers or mixtures thereof, b) their preparation by reaction: either of a hydroxylamine salt with an N-substituted o-(p-tolyl)benzaldimine, to give o-(p-tolyl)benzaldoxime or of an N-substituted 2-halobenzaldimine with a p-tolylmagnesium halide in the presence of an inorganic manganese derivative, to give the compounds of formula I in which R1 represents C3-C7 alkyl or C3-C7 cycloalkyl c) their use for the preparation of o-(p-tolyl)-benzonitrile, which is an intermediate in the synthesis of medicinal products.
    Type: Grant
    Filed: October 23, 2000
    Date of Patent: July 9, 2002
    Assignee: Sanofi-Synthelabo
    Inventors: Jean-Robert Dormoy, Dominique Goubet, Patrice Moreau
  • Patent number: 6320067
    Abstract: A nitrile having formula (2): RC≡N  (2) wherein R represents a substituted or unsubstituted alkyl, alkenyl, aralkyl or aryl group having 3 to 20 carbon atoms, is produced by a process, which comprises heating an aldoxime having formula (1): RCH═NOH  (1) wherein R is as defined above, at 80 to 250° C. in the presence of a catalyst (A) of an alkali metal or alkaline earth metal salt of a saturated or unsaturated mono- or dicarboxylic acid having 2 to 20 carbon atoms while removing product water from the reaction system by distillation.
    Type: Grant
    Filed: May 26, 2000
    Date of Patent: November 20, 2001
    Assignee: Kao Corporation
    Inventors: Masayuki Oku, Junji Koshino
  • Patent number: 6222058
    Abstract: Disclosed is a process for the production of cyclopropanecarbonitrile (CPCN) by feeding concurently cyclopropanecarboxaldehyde (CPCA) and hydroxylamine aqueous solution to a reaction zone which contains formic acid. The process avoids the formation and accumulation of large amounts CPCA oxime intermediates which exhibit a very high energy release upon thermal decomposition. Additional embodiments of the invention comprise the steps of (1) synthesizing CPCN by feeding concurrently CPCA and hydroxylamine aqueous solution to a reaction zone containing formic acid to form a reaction product mixture comprising CPCN and (2) isolating and recovering the CPCN by contacting the reaction product mixture with a base to obtain a mixture comprising an organic phase containing CPCN and an aqueous phase.
    Type: Grant
    Filed: March 30, 1998
    Date of Patent: April 24, 2001
    Assignee: Eastman Chemical Company
    Inventor: Shaowo Liang
  • Patent number: 6020515
    Abstract: A novel process for the preparation of malononitrile which involves subjecting a (2-cyano-N-alkoxy)acetimidoyl halide to a high-temperature treatment.
    Type: Grant
    Filed: March 19, 1999
    Date of Patent: February 1, 2000
    Assignee: Lonza, Ltd.
    Inventors: Peter Chen, Johannes Hoffner, Andre Mueller, Rudolf Fuchs
  • Patent number: 5892092
    Abstract: A process for preparing unsaturated nitriles of the formula I ##STR1## where R, R.sup.1 and R.sup.2 are each independently of one another alkyl or alkenyl each having 1-20 carbon atoms or cycloalkyl or cycloalkenyl each having 3-12 carbon atoms and any two of the radicals R, R.sup.1 and R.sup.2 may be part of a saturated or unsaturated ring and R.sup.1 and R.sup.2 may also be hydrogen and n is 0 or 1-20, by dehydration of oximes of the formula II ##STR2## where R, R.sup.1, R.sup.2 and n are as defined above, comprises dehydrating in the gas or liquid phase at from 150.degree. to 300.degree. C. over a heterogeneous catalyst consisting of an oxidic, carbidic or nitridic support doped with basic oxides and/or hydroxides or compounds which are converted into said oxides or hydroxides under the reaction conditions, or of said basic oxides.
    Type: Grant
    Filed: August 31, 1998
    Date of Patent: April 6, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Kramer, Wolfgang Siegel, Michael Henningsen, Georg Heinrich Grosch
  • Patent number: 5847190
    Abstract: The present invention relates to dendritic, nitrogen-containing organic compounds containing at least 4 planar-chiral or axial-chiral groups, where these planar-chiral or axial-chiral groups are linked as Schiff's bases to the primary amino groups of compounds of the formula (I)(R.sup.1 R.sup.1)N--X--N(R.sup.1 R.sup.1) (I)whereR.sup.1 is (R.sup.2 R.sup.2)N--(CH.sub.2).sub.2 -- or (R.sup.2 R.sup.2)N--(CH.sub.2).sub.3 --,R.sup.2 is hydrogen or (R.sup.3 R.sup.3)N--CH.sub.2).sub.2 -- or (R.sup.3 R.sup.3)N--(CH.sub.2).sub.3 --,R.sup.3 is hydrogen or (R.sup.4 R.sup.4)N--(CH.sub.2).sub.2 -- or (R.sup.4 R.sup.4)N--(CH.sub.2).sub.3 --,R.sup.4 is hydrogen or (R.sup.5 R.sup.5)--N--(CH.sub.2).sub.2 -- or (R.sup.5 R.sup.5)N--(CH.sub.2).sub.3 --,R.sup.5 is hydrogen or (R.sup.6 R.sup.6)N--(CH.sub.2).sub.2 -- or (R.sup.6 R.sup.6)N--(CH.sub.2).sub.3 -- andR.sup.6 is hydrogen,X is an aliphatic and/or aromatic group, which may contain heteroatoms,which are suitable as catalysts for asymmetrical homogeneous catalysis.
    Type: Grant
    Filed: May 20, 1997
    Date of Patent: December 8, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Paulus, Fritz Vogtle, Jorg Issberner
  • Patent number: 5763638
    Abstract: A process for the preparation of nitriles of formula ##STR1## wherein X is CH or N, and R.sub.1 and R.sub.2 are each independently of the other hydrogen, chloro, bromo, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylamino, CN, phenyl, phenoxy, dimethylamino, piperidyl, morpholinyl or pyrrolidyl, or R.sub.1 and R.sub.2 together form a fused benzene ring, by reacting an aldehyde of formula ##STR2## with hydroxylaminosulfate in the presence of a tertiary amine base of formula ##STR3## wherein R.sub.3 and R.sub.4 are each independently of the other hydrogen, methyl or ethyl, R.sub.5 is branched C.sub.3 -C.sub.5 alkyl or phenyl, and R.sub.6 and R.sub.7 are methyl or ethyl,in the temperature range from 100.degree. to 160.degree. C., while distilling the released water of reaction off concomittantly at a pressure in the range of 0.02 to 1.5 bar, with subsequent removal of the ammonium salts, and isolating the nitrile so obtained by customary methods.
    Type: Grant
    Filed: February 4, 1997
    Date of Patent: June 9, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventor: Richard Breitschuh
  • Patent number: 5637750
    Abstract: A method for the preparation of a 2-hydroxybenzonitrile which comprises reacting hydroxylamine with a 2-hydroxyarylaldehyde which is at least partially in the form of a salt and/or complex of a metal of Group II, Group III, Group IVA or Group VIA of the Periodic Table and dehydrating the 2-hydroxyarylaldoxime so formed.
    Type: Grant
    Filed: August 18, 1995
    Date of Patent: June 10, 1997
    Assignee: Zeneca Limited
    Inventor: Daniel Levin
  • Patent number: 5514830
    Abstract: The present invention provides a process for producing a nitrile represented by the general formula (1):RC.ident.N (1)wherein R is alkyl, alkenyl, aralkyl or aryl, each may have a substituent, characterized by heating an aldoxime represented by the general formula (2):RCH.dbd.NOH (2)wherein R is as defined above, in the presence of one or more catalysts selected from hydroxides of alkali metals, alcoholates of alkali metals, hydroxides of alkaline earth metals and alcoholates of alkaline earth metals, and distilling off water formed in the course of the reaction from the reaction system. The process according to the present invention can produce a nitrile which is useful as a perfume or as a starting material for the organic synthesis of perfumes, medicines and so on in high yields and advantageously from the viewpoint of production economy.
    Type: Grant
    Filed: April 21, 1995
    Date of Patent: May 7, 1996
    Assignee: Kao Corporation
    Inventors: Masayuki Oku, Yoshiaki Fujikura
  • Patent number: 5502234
    Abstract: Disclosed is a novel process for the preparation and separation of cyclopropanecarbonitrile (CPCN) from cyclopropropanecarboxaldehyde (CPCA) using a combination of three process steps. The process involves the steps of (1) reacting (CPCA) with hydroxylamine base in the presence of water to obtain CPCA oxime, (2) contacting the CPCA oxime of step (1) with formic acid to obtain CPCN, and (3) contacting the mixture comprising CPCN formed in step (2) with a base to obtain a mixture comprising an organic phase containing CPCN and an aqueous phase. The reactants and intermediates involved in each step are used within certain defined ratios.
    Type: Grant
    Filed: July 17, 1995
    Date of Patent: March 26, 1996
    Assignee: Eastman Chemical Company
    Inventor: Shaowo Liang
  • Patent number: 5457222
    Abstract: The present invention provides a process for producing a nitrile represented by the general formula (1):RC.ident.N (1)wherein R is alkyl, alkenyl, aralkyl or aryl, each may have a substituent, characterized by heating an aldoxime represented by the general formula (2):RCH=NOH (2)wherein R is as defined above, in the presence of one or more catalysts selected from hydroxides of alkali metals, alcoholates of alkali metals, hydroxides of alkaline earth metals and alcoholates of alkaline earth metals, and distilling off water formed in the course of the reaction from the reaction system. The process according to the present invention can produce a nitrile which is useful as a perfume or as a starting material for the organic synthesis of perfumes, medicines and so on in high yields and advantageously from the viewpoint of production economy.
    Type: Grant
    Filed: March 1, 1995
    Date of Patent: October 10, 1995
    Assignee: Kao Corporation
    Inventors: Masayuki Oku, Yoshiaki Fujikura
  • Patent number: 5349103
    Abstract: A process for the preparation of a nitrile of formula ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl, by reaction of an aldehyde of formula ##STR2## wherein R is as defined above, with hydroxylamine sulfate and subsequent dehydration, which process comprises carrying out the reaction in propionic acid in the presence of a salt of propionic acid by heating to an external temperature in the range from 140.degree. to 165.degree. C., preferably from 150.degree. to 160.degree. C., for 2 to 6 hours, preferably for 3 to 5 hours, under atmospheric pressure, and simultaneously distilling the mixture of propionic acid and water from the system until a solution forms, and thereafter removing the mixture of propionic acid and water at 100.degree.-130.degree. C., preferably 110.degree.-120.degree. C., by vacuum distillation, and then isolating the resultant nitrile by standard procedures.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: September 20, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: Bilge Gulec
  • Patent number: 5281744
    Abstract: A process for the preparation of nitriles in which an ethylenically unsaturated compound is reacted with carbon monoxide, a hydrogen source and hydroxylamine or a hydroxylamine salt in the presence of a catalyst system comprising one or more Group VIII metals.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: January 25, 1994
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 5097058
    Abstract: New process for the synthesis of the .alpha.-(1-m.ethylethyl)-3,4-dimethoxyacetonitrile of formula (I): ##STR1## which is known as an intermediate in the synthesis of the drug internationally known as verapamil. The process starts from the isobutyryl-3,4-dimethoxybenzene of formula (II): ##STR2## which, by means of the Darzens condensation, gives an epoxyester which, by alkaline hydrolysis and subsequent decarboxylation, gives the .alpha.-(1-methylethyl)-3,4-dimethoxybenzeneacetaldehyde. This product is reacted with hydroxylamine to obtain the corresponding oxime that, by dehydration, gives the nitrile of formula I.
    Type: Grant
    Filed: April 25, 1990
    Date of Patent: March 17, 1992
    Assignee: Alfa Wassermann S.p.A.
    Inventors: Vincenzo Cannata, Giancarlo Tamerlani, Graziano Zagnoni
  • Patent number: 4808746
    Abstract: In preparing trifluoromethylbenzonitrile by reaction of trifluoromethylbenzaldehyde with hydroxylamine, the rate of reaction is enhanced and formation of trifluoromethylbenzamide is suppressed by carrying out the reaction in an organic solvent which is immiscible with water and has a sufficiently high boiling point, e.g. nitrotoluene, and continuously distilling by-produced water from the reaction system. The solvent can easily and almost entirely be recovered and reused.
    Type: Grant
    Filed: December 7, 1987
    Date of Patent: February 28, 1989
    Assignee: Central Glass Company, Limited
    Inventors: Yasunobu Nishimura, Toshikazu Kawai, Yoshikazu Sugimori
  • Patent number: 4686302
    Abstract: Nitriles of the general formula IR.sup.1 --CN (I)where R.sup.1 is a saturated or unsaturated, straight-chain, branched or cyclic alkyl radical, an aralkyl radical or an aryl radical, each of which is of not more than 20 carbon atoms and can be unsubstituted or further substituted, and (meth)acrylamide are prepared simultaneously by a process in which an aldoxime of the general formula IIIR.sup.1 --CH.dbd.NOH (III)where R.sup.1 has the above meanings, is heated at from 50.degree. to 180.degree. C. in the presence of a copper(II) carboxylate and of (meth)acrylonitrile.
    Type: Grant
    Filed: November 30, 1984
    Date of Patent: August 11, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Wolfgang Schwarz
  • Patent number: 4591461
    Abstract: A novel process for the preparation of a 16-imino-17-aza-steroid of the formula ##STR1## wherein A is selected from the group consisting of hydrogen and tritium comprising reacting a compound of the formula ##STR2## wherein A has the above definition and R is an acyl of an organic carboxylic acid of 1 to 8 carbon atoms with an oximation agent to obtain a compound of the formula ##STR3## reacting the latter with an agent to form an acid chloride to obtain a compound of the formula ##STR4## reacting the latter with ammonia to obtain a compound of the formula ##STR5## reacting the latter with an alkali metal hypohalite in the presence of a base to obtain a compound of the formula ##STR6## wherein X is a halogen and reacting the latter with a base to obtain the desired compound and the novel compound of formula I wherein A is tritium and the novel intermediates of formulae III, IV, V and VI.
    Type: Grant
    Filed: October 28, 1985
    Date of Patent: May 27, 1986
    Assignee: Roussel Uclaf
    Inventors: Alain Jouquey, Peter F. Hunt