Liquid Phase Reaction Patents (Class 558/313)
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Patent number: 12084404Abstract: 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: GrantFiled: May 25, 2022Date of Patent: September 10, 2024Assignee: API CORPORATIONInventors: Masaki Nagahama, Daiki Okado, Hirotsugu Taniike
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Patent number: 12037307Abstract: 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: GrantFiled: May 25, 2022Date of Patent: July 16, 2024Assignee: API CORPORATIONInventors: Masaki Nagahama, Daiki Okado, Hirotsugu Taniike
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Patent number: 11352318Abstract: 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: GrantFiled: August 6, 2018Date of Patent: June 7, 2022Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Akifumi Iida, Emi Nakano, Yutaka Kanbara
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Patent number: 10899722Abstract: The present invention relates to a process for the preparation of fluoroalkylnitriles and the corresponding fluoroalkyltetrazoles starting from fluorinated carboxamides.Type: GrantFiled: February 22, 2018Date of Patent: January 26, 2021Assignee: BAYER CROPSCIENCE AKTIENGESELLSCHAFTInventors: Albert Schnatterer, Jan Vermehren, Edith Beckmann, Claus-Christian Haeselhoff, Tim Hammerer, Stefan Grasser
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Patent number: 10750781Abstract: 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: GrantFiled: March 24, 2020Date of Patent: August 25, 2020Assignee: SHENZHEN SMOORE TECHNOLOGY LIMITEDInventor: Zhiping Chen
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Patent number: 10349678Abstract: 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: GrantFiled: June 30, 2015Date of Patent: July 16, 2019Assignee: SHENZHEN SMOORE TECHNOLOGY LIMITEDInventor: Zhiping Chen
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Patent number: 8471052Abstract: 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: GrantFiled: November 20, 2009Date of Patent: June 25, 2013Assignee: Orochem Technologies Inc.Inventors: Anil Oroskar, Paul Roman Kurek, Asha Oroskar
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Patent number: 8203015Abstract: The present invention relates to a process for preparing fluoroalkyl nitriles by reacting fluorinated carboxamides with halides and fluorinated carboxylic acids.Type: GrantFiled: June 7, 2010Date of Patent: June 19, 2012Assignee: Bayer Cropscience AGInventors: Norbert Lui, Jens-Dietmar Heinrich, Thomas Wollner, Sergii Pazenok
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Publication number: 20110124901Abstract: 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: ApplicationFiled: November 20, 2009Publication date: May 26, 2011Inventors: Anil Oroskar, Paul Roman Kurek, Asha Oroskar
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Publication number: 20100312002Abstract: The present invention relates to a process for preparing fluoroalkyl nitriles by reacting fluorinated carboxamides with halides and fluorinated carboxylic acids.Type: ApplicationFiled: June 7, 2010Publication date: December 9, 2010Applicant: Bayer CropScience AGInventors: Norbert Lui, Jens-Dietmar Heinrich, Thomas Wollner, Sergii Pazenok
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Publication number: 20100185007Abstract: 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: ApplicationFiled: June 24, 2008Publication date: July 22, 2010Inventors: Akiyoshi Yamauchi, Kensuke Mohara, Keiko Takao, Meiten Koh
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Patent number: 7164047Abstract: 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: GrantFiled: October 31, 2002Date of Patent: January 16, 2007Assignee: Kuraray Co., Ltd.Inventor: Katsuji Ujita
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Patent number: 6710200Abstract: 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: GrantFiled: January 7, 2003Date of Patent: March 23, 2004Assignee: The Regents of the University of CaliforniaInventors: Bruce D. Hammock, Guomin Shan, Rong Zhang
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Patent number: 6297393Abstract: 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: GrantFiled: August 31, 2000Date of Patent: October 2, 2001Assignee: Council of Scientific and Industrial ResearchInventors: Ananda Kumar Bandyopadhyay, Khathija Aziz, Pravin Raybaji Likhar, Boyapati Manoranjan Choudary
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Patent number: 6005134Abstract: 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: GrantFiled: May 19, 1999Date of Patent: December 21, 1999Assignee: Kao CorporationInventors: Michio Terasaka, Yasuyuki Mimura, Hiroshi Abe
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Patent number: 5883260Abstract: 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: GrantFiled: June 23, 1997Date of Patent: March 16, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Toshio Nagatomi, Shigeki Yokoi, Yoshimi Yamada
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Patent number: 5637748Abstract: 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: GrantFiled: March 1, 1995Date of Patent: June 10, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ming-Hong Hung, Vinayakam Subramanyam
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Patent number: 5395974Abstract: 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: GrantFiled: January 21, 1994Date of Patent: March 7, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ronald J. McKinney
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Patent number: 5302756Abstract: 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: GrantFiled: December 23, 1992Date of Patent: April 12, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ronald J. McKinney
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Patent number: 5202455Abstract: 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: GrantFiled: September 6, 1991Date of Patent: April 13, 1993Assignee: Huels AktiengesellschaftInventor: Karl Schmitz
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Patent number: 5142085Abstract: 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: GrantFiled: August 12, 1991Date of Patent: August 25, 1992Assignee: Roussel UclafInventors: Jean-Marc Barry, Serge Droux, Giuseppe Gigliotti
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Patent number: 5138086Abstract: 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: GrantFiled: November 21, 1990Date of Patent: August 11, 1992Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tadatoshi Honda, Sinji Tokunoh
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Patent number: 5068408Abstract: A process for oxidizing an organic compound selected from an aliphatic, aromatic, aliphatic/aromatic, cycloaliphatic and heterocyclic alcohol, thiol, sulfide, aldehyde, amine, amide, ketone, acid, ether, ester, and organic compounds containing an activated carbon-carbon double bond, which process comprises contacting said organic compound dissolved in an organic solvent with a hypochlorous acid solution.Type: GrantFiled: January 31, 1990Date of Patent: November 26, 1991Assignee: Olin CorporationInventors: Robert J. Raynor, Budd L. Duncan
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Patent number: 5059709Abstract: 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: GrantFiled: November 13, 1990Date of Patent: October 22, 1991Assignee: American Cyanamid CompanyInventors: John P. Dusza, Robert F. Church
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Patent number: 4973746Abstract: 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: GrantFiled: October 24, 1988Date of Patent: November 27, 1990Assignee: General Electric CompanyInventors: Kenneth P. Blackmon, Daniel W. Fox, Sheldon J. Shafer
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Patent number: 4908452Abstract: 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: GrantFiled: December 21, 1987Date of Patent: March 13, 1990Assignee: Merck & Co., Inc.Inventor: David A. Claremon
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Patent number: 4883894Abstract: 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: GrantFiled: March 24, 1987Date of Patent: November 28, 1989Assignee: Caffaro s.p.a. Societa per l'Industria Chimica ed ElettrochimicaInventors: Enrico Pontoglio, Sandro Parodi, Giancarlo Caretti
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Patent number: 4801730Abstract: 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: GrantFiled: November 19, 1987Date of Patent: January 31, 1989Assignee: Hoechst AktiengesellschaftInventors: Herbert Stuhler, Kurt Fischer
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Patent number: 4605521Abstract: 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: GrantFiled: March 29, 1985Date of Patent: August 12, 1986Assignee: Eastman Kodak CompanyInventors: Robert J. I. Eubanks, James G. Pacifici
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Patent number: 4599202Abstract: 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: GrantFiled: July 3, 1985Date of Patent: July 8, 1986Assignee: BASF AktiengesellschaftInventors: Toni Dockner, Manfred Sauerwald, Jost H. Manegold, Hans Leitner