Liquid Phase Reaction Patents (Class 558/313)
  • Patent number: 12084404
    Abstract: The present invention provides high purity 2-naphthylacetonitrile with fewer impurities that is useful as a starting material or intermediate for the synthesis of various pharmaceutical products, agricultural chemicals, and chemical products, and a production method thereof. A high purity 2-naphthylacetonitrile having an HPLC purity of 2-naphthylacetonitrile of not less than 95 area %, and containing naphthalene compounds represented by the formulas (a)-(j) at a content of a predetermined area % or below. A method for producing high purity 2-naphthylacetonitrile, including the following step 1 and step 2: step 1: a step of subjecting 2?-acetonaphthone to a Willgerodt reaction in the presence of an additive where necessary, and hydrolyzing the obtained amide compound to give 2-naphthylacetic acid; step 2: a step of reacting the 2-naphthylacetic acid obtained in step 1, a halogenating agent and sulfamide in the presence of a catalyst as necessary in an organic solvent to give 2-naphthylacetonitrile.
    Type: Grant
    Filed: May 25, 2022
    Date of Patent: September 10, 2024
    Assignee: API CORPORATION
    Inventors: Masaki Nagahama, Daiki Okado, Hirotsugu Taniike
  • Patent number: 12037307
    Abstract: The present invention provides high purity 2-naphthylacetonitrile with fewer impurities that is useful as a starting material or intermediate for the synthesis of various pharmaceutical products, agricultural chemicals, and chemical products, and a production method thereof. A high purity 2-naphthylacetonitrile having an HPLC purity of 2-naphthylacetonitrile of not less than 95 area %, and containing naphthalene compounds represented by the formulas (a)-(j) at a content of a predetermined area % or below. A method for producing high purity 2-naphthylacetonitrile, including the following step 1 and step 2: step 1: a step of subjecting 2?-acetonaphthone to a Willgerodt reaction in the presence of an additive where necessary, and hydrolyzing the obtained amide compound to give 2-naphthylacetic acid; step 2: a step of reacting the 2-naphthylacetic acid obtained in step 1, a halogenating agent and sulfamide in the presence of a catalyst as necessary in an organic solvent to give 2-naphthylacetonitrile.
    Type: Grant
    Filed: May 25, 2022
    Date of Patent: July 16, 2024
    Assignee: API CORPORATION
    Inventors: Masaki Nagahama, Daiki Okado, Hirotsugu Taniike
  • Patent number: 11352318
    Abstract: The present invention provides a production method for dicyanocyclohexane, including a step of obtaining dicyanocyclohexane by reacting cyclohexanedicarboxylic acid and/or a salt thereof, or a heated concentrate of an aqueous ammonia solution of cyclohexanedicarboxylic acid with ammonia in a solvent having a boiling point equal to or higher than a reaction temperature.
    Type: Grant
    Filed: August 6, 2018
    Date of Patent: June 7, 2022
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Akifumi Iida, Emi Nakano, Yutaka Kanbara
  • Patent number: 10899722
    Abstract: The present invention relates to a process for the preparation of fluoroalkylnitriles and the corresponding fluoroalkyltetrazoles starting from fluorinated carboxamides.
    Type: Grant
    Filed: February 22, 2018
    Date of Patent: January 26, 2021
    Assignee: BAYER CROPSCIENCE AKTIENGESELLSCHAFT
    Inventors: Albert Schnatterer, Jan Vermehren, Edith Beckmann, Claus-Christian Haeselhoff, Tim Hammerer, Stefan Grasser
  • Patent number: 10750781
    Abstract: An electronic cigarette, an atomizer device thereof and a method for assembling the atomizer device are provided. The atomizer device comprises an atomizer assembly (14) having an atomizer base (141), a heating member (142), and a liquid transport member (143). The atomizer base (141) includes a tubular body (1412) having an inserting end (1413); and a side wall of the tubular body (1412) defines at least one slot (1414) extending along a longitudinal direction and communicating with an end surface of the inserting end (1413). The heating member (142) is tubular and arranged in the tubular body (1412), and an air flowing channel is defined inside the heating member (142). The liquid transport member (143) comprises a tubular liquid transport body (1431) and at least one couple of connecting portions (1432) connected together in a circumferential direction of the liquid transport body (1431).
    Type: Grant
    Filed: March 24, 2020
    Date of Patent: August 25, 2020
    Assignee: SHENZHEN SMOORE TECHNOLOGY LIMITED
    Inventor: Zhiping Chen
  • Patent number: 10349678
    Abstract: An electronic cigarette, an atomizer device thereof and a method for assembling the atomizer device are provided. The atomizer device comprises an atomizer assembly (14) having an atomizer base (141), a heating member (142), and a liquid conductive member (143). The atomizer base (141) includes a cylindrical body (1412) having an inserting end (1413); and a side wall of the cylindrical body (1412) defines at least one slot (1414) extending along a vertical direction and communicating with an end surface of the inserting end (1413). The heating member (142) is cylindrical and arranged in the cylindrical body (1412), and an air flowing channel is defined inside the heating member (142). The liquid conductive member (143) comprises a cylindrical liquid conductive body (1431) and at least one couple of connecting portions (1432) connected together in a circumferential direction of the liquid conductive body (1431).
    Type: Grant
    Filed: June 30, 2015
    Date of Patent: July 16, 2019
    Assignee: SHENZHEN SMOORE TECHNOLOGY LIMITED
    Inventor: Zhiping Chen
  • Patent number: 8471052
    Abstract: A process is disclosed for producing organic nitriles such as Acetonitrile or Hydrogen Cyanide, in which yields may exceed 90%, undesirable by-products are not produced, and handling of ammonia gas is avoided. In one aspect, a process includes preparing a feed including ammonium salts and water; introducing the feed into a reactor containing a catalyst; and heating the feed in the presence of the catalyst. The catalyst may advantageously include molybdenum on a silica or silica alumina support. The feed may be ammonium acetate in water with about 50 wt % ammonium acetate and the balance water or ammonium formate in water. In another aspect, a process includes preparing a feed including ammonium hydroxide and acetic acid; introducing the feed into a reactor containing a catalyst; and heating the feed in the presence of the catalyst.
    Type: Grant
    Filed: November 20, 2009
    Date of Patent: June 25, 2013
    Assignee: Orochem Technologies Inc.
    Inventors: Anil Oroskar, Paul Roman Kurek, Asha Oroskar
  • Patent number: 8203015
    Abstract: The present invention relates to a process for preparing fluoroalkyl nitriles by reacting fluorinated carboxamides with halides and fluorinated carboxylic acids.
    Type: Grant
    Filed: June 7, 2010
    Date of Patent: June 19, 2012
    Assignee: Bayer Cropscience AG
    Inventors: Norbert Lui, Jens-Dietmar Heinrich, Thomas Wollner, Sergii Pazenok
  • Publication number: 20110124901
    Abstract: A process is disclosed for producing organic nitriles such as Acetonitrile or Hydrogen Cyanide, in which yields may exceed 90%, undesirable by-products are not produced, and handling of ammonia gas is avoided. In one aspect, a process includes preparing a feed including ammonium salts and water; introducing the feed into a reactor containing a catalyst; and heating the feed in the presence of the catalyst. The catalyst may advantageously include molybdenum on a silica or silica alumina support. The feed may be ammonium acetate in water with about 50 wt % ammonium acetate and the balance water or ammonium formate in water. In another aspect, a process includes preparing a feed including ammonium hydroxide and acetic acid; introducing the feed into a reactor containing a catalyst; and heating the feed in the presence of the catalyst.
    Type: Application
    Filed: November 20, 2009
    Publication date: May 26, 2011
    Inventors: Anil Oroskar, Paul Roman Kurek, Asha Oroskar
  • Publication number: 20100312002
    Abstract: The present invention relates to a process for preparing fluoroalkyl nitriles by reacting fluorinated carboxamides with halides and fluorinated carboxylic acids.
    Type: Application
    Filed: June 7, 2010
    Publication date: December 9, 2010
    Applicant: Bayer CropScience AG
    Inventors: Norbert Lui, Jens-Dietmar Heinrich, Thomas Wollner, Sergii Pazenok
  • Publication number: 20100185007
    Abstract: There are provided simple processes for preparing a fluoroamide and a fluoronitrile which assure higher yield, i.e., a process for preparing a fluoroamide represented by the formula (2): CF2?CF—Rf—CONH2, wherein Rf is a perfluoroalkylene group or perfluorooxyalkylene group having 2 to 20 carbon atoms, by allowing a fluoroester represented by the formula (1): CF2?CF—Rf—COOR, wherein Rf is as defined above; R is an alkyl group having 1 to 6 carbon atoms, to react with ammonia or ammonium hydroxide, and a process for preparing a fluoronitrile represented by the formula (3): CF2?CF—Rf—CN, wherein Rf is as defined above, by allowing the fluoroamide obtained by the above-mentioned preparation process to react with a dehydrating agent (c) in a solvent (b) having an ether bond, an ester bond, a ketone group or a cyano group.
    Type: Application
    Filed: June 24, 2008
    Publication date: July 22, 2010
    Inventors: Akiyoshi Yamauchi, Kensuke Mohara, Keiko Takao, Meiten Koh
  • Patent number: 7164047
    Abstract: A process for preparation of cyclopropylethanol, which comprises subjecting a 3-cyclopropyl-2,3-epoxypropionic acid ester to solvolysis, treating the product of the solvolysis with an acid to obtain cyclopropylacetaldehyde, and reducing the obtained cyclopropylacetaldehyde; and a process for preparation of cyclopropylacetonitrile, which comprises subjecting a 3-cyclopropyl-2,3-epoxypropionic acid ester to solvolysis in the presence of a base, treating the product of the solvolysis with an acid to obtain cyclopropylacetaldehyde, reacting the obtained cyclopropylacetaldehyde with hydroxylamine or salts thereof to obtain cyclopropaneacetaldehyde oxime, and reacting the obtained cyclopropaneacetaldehyde oxime with acetic anhydride. According to the present invention, cyclopropylethanol and cyclopropylacetonitrile can be prepared at low costs and industrially advantageously.
    Type: Grant
    Filed: October 31, 2002
    Date of Patent: January 16, 2007
    Assignee: Kuraray Co., Ltd.
    Inventor: Katsuji Ujita
  • Patent number: 6710200
    Abstract: Ethers and esters of cyanohydrins that contain optically detectable moieties are highly effective for detecting, monitoring, and measuring the activity of enzymes that cause the cleavage of certain types of substrates. The cyanohydrins function as proaldehydes and proketones, spontaneously converting to aldehydes and ketones, respectively, which provide a large increase in optical detectability relative to both the starting esters and ethers and the cyanohydrins.
    Type: Grant
    Filed: January 7, 2003
    Date of Patent: March 23, 2004
    Assignee: The Regents of the University of California
    Inventors: Bruce D. Hammock, Guomin Shan, Rong Zhang
  • Patent number: 6297393
    Abstract: The invention describes an improved process for the preparation of malononitrile by using a porous particulate solid substance as efficient absorbent. Cyanoacetamide is reacted with POCl3 as a dehydrating agent in a suitable solvent in the presence of an organic N-donor base as catalyst and a porous particulate solid substance as efficient absorbent. The product is then distilled under vacuum from the crude in the presence of a stabilizer into a receiver containing the same stabilizer, to obtain malononitrile of high purity and shelf-life.
    Type: Grant
    Filed: August 31, 2000
    Date of Patent: October 2, 2001
    Assignee: Council of Scientific and Industrial Research
    Inventors: Ananda Kumar Bandyopadhyay, Khathija Aziz, Pravin Raybaji Likhar, Boyapati Manoranjan Choudary
  • Patent number: 6005134
    Abstract: The present invention provides a process for preparing a high-quality aliphatic nitrile in a high yield at a low cost without the dissolution of a catalyst in the product, which comprises reacting an aliphatic carboxylic acid, a lower alkyl ester thereof or a fatty acid glyceride with ammonia in the presence of a solid catalyst which exhibits a high activity even at a reaction temperature of as low as 300.degree. C. or below and is difficultly soluble in the reaction fluid; and a process for the preparation of amines by hydrogenating the aliphatic nitrile prepared by the above process. Namely, the present invention provides a process for the preparation of an aliphatic nitrile by reacting an aliphatic carboxylic acid, a lower alkyl ester thereof or a fatty acid glyceride with ammonia in the presence of a composite oxide catalyst comprising titanium oxide as the main component; and a process for the preparation of amines by hydrogenating the aliphatic nitrile prepared by the above process.
    Type: Grant
    Filed: May 19, 1999
    Date of Patent: December 21, 1999
    Assignee: Kao Corporation
    Inventors: Michio Terasaka, Yasuyuki Mimura, Hiroshi Abe
  • Patent number: 5883260
    Abstract: The subject is to provides a process for producing 1-substituted-hydantoins of Formula I: ##STR1## wherein R.sub.1 represents d hydrocarbon group which may be substituted and others,cheracterized by reacting N-sustituted-N-alkcycarbonylamnilo-acetonitrile of Formula II: ##STR2## wherein R.sub.2 represents an alkyl group and others, with an alkali metal hydroxides or the like and then treating with an acid.
    Type: Grant
    Filed: June 23, 1997
    Date of Patent: March 16, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshio Nagatomi, Shigeki Yokoi, Yoshimi Yamada
  • Patent number: 5637748
    Abstract: Syntheses of fluorinated amide and fluorinated nitrile compounds are improved by use of particular media for the reactions. Fluorinated amide can also be synthesized in high yield in a neat reaction.
    Type: Grant
    Filed: March 1, 1995
    Date of Patent: June 10, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ming-Hong Hung, Vinayakam Subramanyam
  • Patent number: 5395974
    Abstract: The present invention relates to a method of reacting polyamides or mixtures thereof with ammonia to obtain a mixture of monomers. The reaction is carried out in the presence of certain Lewis Acid catalyst precursors.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: March 7, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Ronald J. McKinney
  • Patent number: 5302756
    Abstract: Useful monomeric products are obtained in the reaction of nylon 6,6 with ammonia. Increased yield of monomer products from nylon 6,6 is obtained from ammonolysis when a mixture with nylon 6 is employed.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: April 12, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Ronald J. McKinney
  • Patent number: 5202455
    Abstract: The present invention relates to a process for the liquid-phase preparation of nitriles from aliphatic dicarboxylic acids at temperatures of about 200.degree. to 350.degree. C. using ammonia in the presence of a phosphoric acid-based catalyst, wherein an adsorbent for the catalyst is added to the reaction mixture.
    Type: Grant
    Filed: September 6, 1991
    Date of Patent: April 13, 1993
    Assignee: Huels Aktiengesellschaft
    Inventor: Karl Schmitz
  • Patent number: 5142085
    Abstract: A process for the preparation of a compound of the formula ##STR1## wherein alk.sub.1 and alk.sub.2 are individually alkyl of 1 to 8 carbon atoms comprising reacting a compound of the formula ##STR2## with a dehydrating agent to obtain the corresponding compound of formula I.
    Type: Grant
    Filed: August 12, 1991
    Date of Patent: August 25, 1992
    Assignee: Roussel Uclaf
    Inventors: Jean-Marc Barry, Serge Droux, Giuseppe Gigliotti
  • Patent number: 5138086
    Abstract: A method for preparing an .alpha.,.beta.-unsaturated nitrile comprises bringing an .alpha.-oxycarboxylic acid amide represented by the following general formula: ##STR1## wherein R' and R" each represents a hydrogen atom or an alkyl group, with the proviso that at least one of R' and R" represents an alkyl group, into contact with a solid acid catalyst with heating in the presence of water in a molar ratio of not more than 15 with respect to the .alpha.-oxycarboxylic acid amide. The method makes it possible to directly produce an .alpha.,.beta.-unsaturated nitrile at high yield and high selectivity utilizing an .alpha.-oxycarboxylic acid amide as a starting material, which can easily be obtained from an .alpha.-oxynitrile.
    Type: Grant
    Filed: November 21, 1990
    Date of Patent: August 11, 1992
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tadatoshi Honda, Sinji Tokunoh
  • Patent number: 5068408
    Abstract: 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: Grant
    Filed: January 31, 1990
    Date of Patent: November 26, 1991
    Assignee: Olin Corporation
    Inventors: Robert J. Raynor, Budd L. Duncan
  • Patent number: 5059709
    Abstract: A novel process for producing .alpha.-[(dialkylamino) substituted-methylene].beta.-oxo-(substituted) propanenitriles of the formula: ##STR1## where R, R.sub.1 and R .sub.2 are defined in the specification by reacting a substituted isoxazole with a diaklylamide dimethylacetal is provided.
    Type: Grant
    Filed: November 13, 1990
    Date of Patent: October 22, 1991
    Assignee: American Cyanamid Company
    Inventors: John P. Dusza, Robert F. Church
  • Patent number: 4973746
    Abstract: Scrap poly(ethyleneterephthalate) is converted to useful amine and diamine monomers such as para-xylylenediamine, 1,4-bis(aminomethyl)cyclohexane and 4-aminomethyl benzoic acid for the production of various polyamides. The conversion of poly(ethyleneterephthalate) to diamine monomers is achieved by a three step process involving (a) ammonolysis of the poly(ethyleneterephthalate) to produce terephthalamide and ethylene glycol; (b) pyrolytic dehydration of the terephthalamide to produce terephthalonitrile; and (c) hydrogenation of the terephthalonitrile to produce the para-xylylene diamine and/or 1,4-bis(aminomethyl)cyclohexane. The conversion of poly(ethyleneterephthalate) to 4-aminomethyl benzoic acid involves the steps of (a) ammonolysis of the poly(ethyleneterephthalate) to produce terephthalamide; (b) partial pyrolytic dehydration of said terephthalamide to produce 4-cyanobenzoic acid; and (c) hydrogenation of said 4-cyanobenzoic acid to produce 4-aminomethylbenzoic acid.
    Type: Grant
    Filed: October 24, 1988
    Date of Patent: November 27, 1990
    Assignee: General Electric Company
    Inventors: Kenneth P. Blackmon, Daniel W. Fox, Sheldon J. Shafer
  • Patent number: 4908452
    Abstract: A facile and mild process for the preparation of nitriles from reagent sensitive primary carboxamides is described. The process utilizes a (carboxysulfamoyl)ammonium hydroxide compound as the dehydrating agent. It is useful for preparing nitriles which have present other groups which are sensitive to the more conventional methods of dehydration or to other methods of nitrile synthesis. Some novel nitriles prepared by the new method are also described.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: March 13, 1990
    Assignee: Merck & Co., Inc.
    Inventor: David A. Claremon
  • Patent number: 4883894
    Abstract: The present invention relates to a process for the production in continuous of isophthalodinitrile or terephthalodinitrile by simultaneous amidation and dehydration of the respective acid chlorides in steam phase on a fixed bed of a dehydration catalyst.
    Type: Grant
    Filed: March 24, 1987
    Date of Patent: November 28, 1989
    Assignee: Caffaro s.p.a. Societa per l'Industria Chimica ed Elettrochimica
    Inventors: Enrico Pontoglio, Sandro Parodi, Giancarlo Caretti
  • Patent number: 4801730
    Abstract: Glycerides are reacted with ammonia in an amount of at least 200 liters per kilogram of glyceride per hour, at a temperature of 220.degree. to 300.degree. C., and in the presence of special catalysts. Of the product mixture which is formed and removed from the reaction with the excess ammonia, and which is composed essentially of the components water, the desired glycerol and fatty acid nitrile containing fatty acid and fatty acid amide, the latter component is returned to the reaction during the glyceride reaction. After completion of the glyceride reaction, which is indicated when the product mixture contains virtually no more glycerol, all the fatty acid nitrile containing fatty acid and fatty acid amide is further treated, in an after-reaction with a reduced amount of ammonia and at higher temperature, in order to convert the fatty acid and fatty acid amide impurities into fatty acid nitrile.
    Type: Grant
    Filed: November 19, 1987
    Date of Patent: January 31, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Herbert Stuhler, Kurt Fischer
  • Patent number: 4605521
    Abstract: This invention relates to a process for the preparation of organic nitriles. More particularly, the invention relates to a process for the preparation of organic nitriles by reacting organic carboxylic acid primary amides with a dehydrating agent in the presence of a catalytic amount of a particular quaternary ammonium salt.
    Type: Grant
    Filed: March 29, 1985
    Date of Patent: August 12, 1986
    Assignee: Eastman Kodak Company
    Inventors: Robert J. I. Eubanks, James G. Pacifici
  • Patent number: 4599202
    Abstract: Adipodinitrile is prepared by reacting adipic acid with excess ammonia at from 250.degree. to 350.degree. C. in the liquid phase in the presence of a diluent by a process in which a liquid hydrocarbon which is inert under the reaction conditions is used as the diluent.
    Type: Grant
    Filed: July 3, 1985
    Date of Patent: July 8, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Toni Dockner, Manfred Sauerwald, Jost H. Manegold, Hans Leitner