Methionine Per Se Or Salt Thereof Patents (Class 562/559)
  • Patent number: 11577190
    Abstract: The present invention provides a method for purifying carbon dioxide gas characterized in that carbon dioxide gas containing at least one of 3-methylmercaptopropionaldehyde and acrolein is contacted with activated carbon to remove at least one of the 3-methylmercaptopropionaldehyde and acrolein. The present invention provides also a method for producing methionine comprising the purification step of the recovered carbon dioxide.
    Type: Grant
    Filed: April 27, 2018
    Date of Patent: February 14, 2023
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Ryosuke Iwasaki, Takuya Katayama, Norihito Omoto, Yoshiyuki Koizumi, Ryousuke Katagami
  • Patent number: 11180447
    Abstract: An object of the present invention to provide a method for producing methionine with consideration given to the environment. The production method of the present invention comprises a removal step of blowing an inert gas into a liquid containing 5-(2-methylmercaptoethyl)hydantoin and thereby diffusing ammonia remaining in the liquid to obtain an emission gas containing the ammonia, and a recovery step of bringing the emission gas into contact with a washing liquid to recover ammonia contained in the emission gas.
    Type: Grant
    Filed: December 12, 2018
    Date of Patent: November 23, 2021
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Noriyuki Shimada, Takao Mizuno, Daisuke Yamashita
  • Patent number: 11111213
    Abstract: The present provides a method for producing methionine which is characterized by a crystallization step in which carbon dioxide is introduced into a reaction solution containing an alkali salt of methionine which is obtained by hydrolyzing 5-[2-(methylthio)ethyl] imidazoline-2,4-dione in the presence of an alkali compound, thereby precipitating the methionine, and further comprises a step of adding waste methionine to the reaction solution. The method of production of the present invention can improve a yield in the production of methionine.
    Type: Grant
    Filed: April 27, 2018
    Date of Patent: September 7, 2021
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Yoshitaka Satoh, Norihito Omoto, Yoshiyuki Koizumi, Naoya Yamashiro, Ryousuke Katagami
  • Patent number: 11014878
    Abstract: The present invention relates to a method for preparing 3-methylthiopropionaldehyde by reacting methyl mercaptan with acrolein, in which deviations in the stoichiometry of methyl mercaptan to acrolein in the reaction to give 3-methylthiopropionaldehyde are compensated for by supplying or by forming 1,3-bis(methylthio)-1-propanol, and also to the use of 1,3-bis(methylthio)-1-propanol as a storage form of methyl mercaptan and/or 3-methylthiopropionaldehyde.
    Type: Grant
    Filed: February 14, 2017
    Date of Patent: May 25, 2021
    Assignee: Evonik Operations GmbH
    Inventors: Stephan Rautenberg, Sascha Ceylan, Martin Koerfer, Judith Hierold, Harald Jakob, Christian Kaiser, Rainer Malzkorn, Thorsten Merker, Anja Nordschild
  • Patent number: 10774037
    Abstract: The present invention relates to a method for producing a specified ?-amino acid, the method including allowing a specified ?-amino acid amide and water to react with each other in the presence of a zirconium compound which contains zirconium and at least one metal element selected from the group consisting of lithium, nickel, copper, zinc, cesium, barium, hafnium, tantalum, cerium, and dysprosium.
    Type: Grant
    Filed: July 25, 2017
    Date of Patent: September 15, 2020
    Assignee: SHOWA DENKO K.K.
    Inventors: Takanori Aoki, Akira Shibuya, Takamitsu Kobayashi, Hideo Miyata, Shinya Tsukamoto, Manabu Kuwajima, Motoki Murai
  • Patent number: 10329240
    Abstract: There is disclosed a process for the separation of long chain amino acid and long chain dibasic acid, comprising: (1) recovering alkylamine from an aqueous solution of an alkali hydroxide hydrolysis of the mixed amide derivatives by distilling or by extracting with an extractant solvent; (2) cooling the aqueous solution of step (1) to precipitate a mixed alkali salts of long chain amino acid and dibasic acid; (3) recovering the mixed alkali salts of long chain amino acid and dibasic acid to provide a mother liquor; (4) separating long chain amino acid and dibasic acid by acidification-extraction of long chain dibasic acid with an extractant solvent or by selective dissolution of alkali salt of long chain amino acid in an aqueous solvent; and (4) adding an acid to the mother liquor of step (3) to obtain alkanoic acid.
    Type: Grant
    Filed: July 7, 2017
    Date of Patent: June 25, 2019
    Assignee: VITAWORKS IP, LLC
    Inventor: Songzhou Hu
  • Patent number: 10329241
    Abstract: There is disclosed a process for the separation of long chain amino acid and long chain dibasic acid, comprising: (1) cooling the hydrolysis solution to crystallize and separate alkali salt of long chain dibasic acid to provide an aqueous solvent solution; (2) distilling the aqueous solvent solution of step (1) to recover the solvent and to recover alkylamine; (3) cooling the residual solution of step (2) to precipitate and separate alkali salt of long chain amino acid to provide a mother liquor; (4) adding an acid to the mother liquor of step (3) to yield alkanoic acid; (5) adding an acid to an aqueous solution of the alkali salt of long chain dibasic acid of step (1) to obtain long chain dibasic acid; and (6) neutralizing the alkali salt of long chain amino acid of step (3) with an acid to obtain long chain amino acid.
    Type: Grant
    Filed: July 10, 2017
    Date of Patent: June 25, 2019
    Assignee: VITAWORKS IP, LLC
    Inventor: Songzhou Hu
  • Patent number: 9617209
    Abstract: The invention relates to a method for crystallizing D,L-methionine from aqueous solutions and/or suspensions containing D,L-methionine and D,L-methionine ammonium salts, having a Met content of 70-180 g/kg, an NH4+ content of 1-5 g/kg, in the presence of a crystallization additive, which comprises a nonionic or anionic surfactant or a mixture of various nonionic or anionic surfactants, in which the temperature of the solution and/or suspension is lowered directly or stepwise from T1=85-110° C. to T2=30-50° C., so that D,L-methionine precipitates as a solid.
    Type: Grant
    Filed: September 10, 2014
    Date of Patent: April 11, 2017
    Assignee: EVONIK DEGUSSA GmbH
    Inventors: Stefan Reichert, Harald Jakob, Hans Joachim Hasselbach, Martin Koerfer
  • Patent number: 9206120
    Abstract: The present invention discloses a clean method for preparing a D,L-methionine comprising the steps of: preparing a potassium cyanide solution using a crystallized mother solution containing potassium carbonate as an absorbing liquid to absorb hydrocyanic acid, then reacting the potassium cyanide solution with 3-methylthio propionaldehyde and an ammonium bicarbonate solution at 50-150° C. for 3-15 minutes so as to obtain a 5-(?-methylthioethyl)glycolyurea solution, then bring the 5-(?-methylthioethyl)glycolyurea solution to a temperature of 140-220° C. and subjecting to a saponification reaction for 2-5 minutes, after the completion of the saponification, reducing the temperature to 0-40° C., extracting with an organic solvent, neutralizing the water phase with CO2 and crystallizing, then filtering, washing, and drying to obtain an acceptable D,L-methionine product; bring the crystallized D,L-methionine mother solution from filtration to a temperature to 110-160° C.
    Type: Grant
    Filed: January 6, 2013
    Date of Patent: December 8, 2015
    Assignees: ZHEJIANG NHU COMPANY LTD., ZHEJIANG UNIVERSITY, SHANDONG NHU AMINO ACIDS CO., LTD.
    Inventors: Zhirong Chen, Cunchao Wang, Chuqiu Zhao, Sujuan Wang, Chengfeng Zhang, Tao Long, Xinhong Liu
  • Patent number: 9024063
    Abstract: The present invention relates to a method for increasing L-methionine productivity and organic acid productivity. More particularly, the present invention relates to a method which involves adding a mixture containing methyl mercaptan and dimethyl sulfide at a appropriate ratio to O-acetyl homoserine or O-succinyl homoserine and to an enzyme having an activity of converting methionine precursor into L-methionine, so as to perform an enzyme reaction, to thereby improve the conversion rate of L-methionine and organic acid from the L-methionine precursor, and thus increasing L-methionine yield as compared to conventional method.
    Type: Grant
    Filed: February 26, 2010
    Date of Patent: May 5, 2015
    Assignee: CJ Cheiljedang Corporation
    Inventors: So Young Kim, Yong Uk Shin, In Kyung Heo, Hyun Ah Kim, Ju Eun Kim, Chang Il Seo, Sung Kwang Son, Sang Mok Lee, Sung Hoo Jhon, Han Jin Lee, Kwang Ho Na, Il Chul Kim
  • Patent number: 8968791
    Abstract: The present invention provides a dietary supplement that promote the growth, repair, and maintenance of mammalian bone and joint connective tissue. In particular, the dietary supplement comprises a combination of at least one metal chelate and at least one chondroprotective agent.
    Type: Grant
    Filed: May 30, 2008
    Date of Patent: March 3, 2015
    Assignee: Novus International, Inc.
    Inventors: Jeremy D. Moore, Thomas R. Hampton, Robert Harrell
  • Publication number: 20150056452
    Abstract: The present invention relates to pulverulent compositions of a complex between an acid and a metal and the method of preparation thereof.
    Type: Application
    Filed: March 15, 2013
    Publication date: February 26, 2015
    Applicant: INNOV'IA 3I
    Inventors: Pierre Buisson, Robert Huet, Sebastien Fournier, Jean-Eudes Vendeville
  • Publication number: 20140316005
    Abstract: A food composition that is useful for increasing antioxidant levels in the body is provided having increased levels of sulfur-containing amino acids, such as methionine, cysteine, or mixtures thereof. Methods of using these compositions for increasing antioxidant levels in the body in mammals, especially in companion animals, are also provided.
    Type: Application
    Filed: July 2, 2014
    Publication date: October 23, 2014
    Inventors: Kim Gene Friesen, Dennis Edward Jewell
  • Publication number: 20140243282
    Abstract: The present invention relates to novel drug conjugates, where in two drugs are linked together through an appropriate linker having at least two functional groups capable of forming covalent bond with drugs D1 and D2. The invention also relates to developing novel compositions, methods for their preparation and their use in treating various disease conditions.
    Type: Application
    Filed: December 12, 2011
    Publication date: August 28, 2014
    Inventor: Satish Reddy Kallam
  • Publication number: 20140213819
    Abstract: A method for the production of 2-hydroxy-4-(methylthio)butyronitrile having good storage stability in a multi-zone reactor, is provided. 3-methylmercaptopropionaldehyde is reacted with hydrogen cyanide in the presence of a base as catalyst in a main reaction zone of the multizone reactor to form a reaction mixture comprising the 2-hydroxy-4-(methylthio)butyronitrile, unreacted 3-methylmercaptopropionaldehyde, the catalyst and residual amounts of gaseous hydrogen cyanide. The residual gaseous hydrogen cyanide is removed from the main reaction zone to an absorption and post-reaction zone of the reactor which comprises a mixture of 3-methylmercaptopropionaldehyde and the catalyst; and the gaseous hydrogen cyanide is further reacted with the 3-methylmercaptopropionaldehyde in the absorption and post reaction zone. A molar ratio of hydrogen cyanide to 3-(methylthio)propanal in the main reaction zone is from 0.98 to 1.03.
    Type: Application
    Filed: March 27, 2014
    Publication date: July 31, 2014
    Applicant: EVONIK DEGUSSA GmbH
    Inventors: Dieter BUSS, Martin STEURENTHALER, Michael R. RINNER, Stephan KRETZ, Hans Joachim HASSELBACH, Caspar-Heinrich FINKELDEI, Martin KOERFER, Pablo ZACCHI
  • Patent number: 8779190
    Abstract: According to the present invention, a new process for producing a sulfur-containing amino acid without using of hydrogen cyanide or sodium azide which requires careful handling as a raw material can be provided. The present invention relates to a process for producing a sulfur-containing amino acid represented by the following formula (1) or a salt thereof: wherein R1 is an alkyl group having 1 to 12 carbon atoms and optionally having substituents or a cycloalkyl group having 3 to 12 carbon atoms and optionally having substituents, and n is an integral number of from 1 to 4, comprising a step of reacting a sulfur-containing 2-ketocarboxylic acid represented by the formula (2) or a salt thereof: wherein R1 and n mean the same as defined above, with ammonia and hydrogen in the presence of a transition metal catalyst.
    Type: Grant
    Filed: March 24, 2011
    Date of Patent: July 15, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazuyasu Tani, Taro Hirose, Koji Hagiya
  • Publication number: 20140155652
    Abstract: The invention provides the following method capable of producing methionine in a shorter time by making rapid progress of the hydrolysis of 5-(2-methylmercaptoethyl)hydantoin from an aqueous 5-(2-methylmercaptoethyl)hydantoin solution containing ammonia component. A method of producing methionine is the method comprising hydrolyzing 5-(2-methylmercaptoethyl)hydantoin in an aqueous 5-(2-methylmercaptoethyl)hydantoin solution containing ammonia component, wherein the hydrolysis is performed after the ammonia component is removed from the aqueous solution.
    Type: Application
    Filed: November 18, 2013
    Publication date: June 5, 2014
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Naoya YAMASHIRO, Junichi NISHIDA, Yoshiyuki KOIZUMI
  • Patent number: 8742170
    Abstract: Provided herein are processes for the production of methionine or selenomethionine from homoserine. In particular, the processes proceed via the production of 4-substituted 2-aminobutanoic acid intermediates or derivatives thereof.
    Type: Grant
    Filed: March 9, 2011
    Date of Patent: June 3, 2014
    Assignee: Novus International, Inc.
    Inventors: Stephen J. Lorbert, Kevin A. Trankler, Richard Vonder Embse, Dayna L. Turner, Tracy Rode, Cynthia K. Snoddy, James C. Peterson
  • Patent number: 8735631
    Abstract: The present invention relates to a method for manufacturing methylmercaptopropionaldehyde (MMP) including at least the following steps: (a) dehydrating glycerol to acrolein from an aqueous solution of glycerol in the presence of an acid catalyst; (b) purifying the aqueous flux from step (a) to obtain a flux of acrolein containing at least 15 wt % of water relative to the acrolein; (c) causing a reaction of the acrolein flux obtained in step (b) with methylmercaptan in the presence of a catalyst; (d) optionally purifying the product obtained in step (c). The method of the invention can also include a reaction of the product obtained in step (c) or (d) with hydrocyanic acid, or sodium cyanide during a step (e) followed by a subsequent transformation to produce methionine or methionine hydroxyanalogue, which can then optionally be purified.
    Type: Grant
    Filed: November 19, 2009
    Date of Patent: May 27, 2014
    Assignee: Arkema France
    Inventors: Jean-François Devaux, Jean-Luc Dubois
  • Patent number: 8729288
    Abstract: A method for the production of 2-hydroxy-4-(methylthio)butyronitrile having good storage stability in a multi-zone reactor, is provided. 3-methylmercaptopropionaldehyde is reacted with hydrogen cyanide in the presence of a base as catalyst in a main reaction zone of the multizone reactor to form a reaction mixture comprising the 2-hydroxy-4-(methylthio)butyronitrile, unreacted 3-methylmercaptopropionaldehyde, the catalyst and residual amounts of gaseous hydrogen cyanide. The residual gaseous hydrogen cyanide is removed from the main reaction zone to an absorption and post-reaction zone of the reactor which comprises a mixture of 3-methylmercaptopropionaldehyde and the catalyst; and the gaseous hydrogen cyanide is further reacted with the 3-methylmercaptopropionaldehyde in the absorption and post reaction zone. A molar ratio of hydrogen cyanide to 3-(methylthio)propanal in the main reaction zone is from 0.98 to 1.03.
    Type: Grant
    Filed: February 22, 2012
    Date of Patent: May 20, 2014
    Assignee: Evonik Degussa GmbH
    Inventors: Dieter Buss, Martin Steurenthaler, Michael R. Rinner, Stephan Kretz, Hans Joachim Hasselbach, Caspar-Heinrich Finkeldei, Martin Koerfer, Pablo Zacchi
  • Publication number: 20140099696
    Abstract: Microspheres are produced by contacting a solution of a macromolecule or small molecule in a solvent with an antisolvent and a counterion, and chilling the solution. The microspheres are useful for preparing pharmaceuticals, nutraceuticals, cosmetic products and the like of defined dimensions.
    Type: Application
    Filed: April 30, 2013
    Publication date: April 10, 2014
    Applicant: Ansun Biopharma, Inc.
    Inventors: Michael P. Malakhov, Fang Fang
  • Patent number: 8669111
    Abstract: The present invention provides reagents and methods for limiting adsorptive and/or oxidative protein losses in a sample.
    Type: Grant
    Filed: January 24, 2013
    Date of Patent: March 11, 2014
    Assignee: Arizona Board of Regents, A Body Corporate of the State of Arizona Acting for and on Behalf of Arizona State University
    Inventors: Douglas Rehder, Matthew Schaab, Chad Borges
  • Patent number: 8653136
    Abstract: Compositions based on amino acids are described, for improving the myocardial ventricular function in patients suffering from diabetes, particularly but not exclusively II type diabetes. The compositions according to the invention comprise up to 75% of the branched chain amino acids leucine, isoleucine and valine, as active ingredients. Preferably, the compositions also comprise, as further active ingredients, up to 50% of threonine and lysine. Other essential amino acids are preferably also provided, in particular methionine, phenylalanine, histidine, tryphtophan, as well as non essential amino acids, in particular tyrosine and/or cyst(e)ine (i.e., cystine and cysteine). Other amino acids can be added, provided that their sum is in a percentage being lower than 20% with respect to the other active ingredients, and less than 10% for each single amino acid.
    Type: Grant
    Filed: April 17, 2008
    Date of Patent: February 18, 2014
    Assignee: Determinants of Metabolism Research Laboratory S.R.L.
    Inventors: Franco Conti, Francesco Saverio Dioguardi
  • Patent number: 8546601
    Abstract: A storage stable mixture containing 86 to 97% by weight of 2-hydroxy-4-methylthiobutyronitrile, 2 to 14% by weight of water, 0.05 to 0.5% by weight of HCN and having a pH of 1 to 4, measured using a pH electrode at 23° C. is provided. A method to produce the storage stable mixture and its use in manufacture of DL-methionine or 2-hydroxy-4-methylthiobutyric acid is also provided.
    Type: Grant
    Filed: February 22, 2012
    Date of Patent: October 1, 2013
    Assignee: Evonik Degussa GmbH
    Inventors: Dieter Buss, Martin Steurenthaler, Joachim Hans Hasselbach, Michael R. Rinner, Benjamin Fonfe, Martin Koerfer, Stephan Kretz
  • Publication number: 20130231503
    Abstract: The present invention relates to a method for producing L-methionine, comprising: i) culturing an L-methionine precursor-producing microorganism strain in a fermentation solution, so that the L-methionine precursor accumulates in the solution; and ii) mixing a converting enzyme and methylmercaptan or its salts with at least a portion of the solution to convert the accumulated L-methionine precursor into L-methionine, as well as to microorganism strains used in each step.
    Type: Application
    Filed: January 29, 2013
    Publication date: September 5, 2013
    Applicant: CJ CHEILJEDANG CORPORATION
    Inventors: So-young Kim, Kwang-myung Choi, Yong-uk Shin, Hye-won Um, Kyung-oh Choi, Jin-sook Chang, Young-wook Cho, Young-hoon Park
  • Publication number: 20130217909
    Abstract: A continuous process for obtaining acrolein by catalytic dehydration of glycerol or glycerin, in the presence of an acid catalyst, wherein said process comprises the concomitant regeneration of said catalyst and is carried out in a fluidized bed reactor, said reactor comprising two zones, a first zone, or lower zone, termed catalyst regeneration zone, in which a fluidization gas comprising oxygen is introduced, and a second zone, or upper zone, termed reaction zone, in which the glycerol or glycerin is introduced and converted into acrolein.
    Type: Application
    Filed: October 26, 2011
    Publication date: August 22, 2013
    Applicants: ECOLE CENTRALE DE LILLE, ADISSEO FRANCE S.A.S.
    Inventors: Stephane Pariente, Virginie Belliere-Baca, Sebastien Paul, Nouria Fatah
  • Publication number: 20130211078
    Abstract: Provided herein are processes for the production of methionine or selenomethionine from homoserine. In particular, the processes proceed via the production of carbamate intermediates.
    Type: Application
    Filed: March 20, 2013
    Publication date: August 15, 2013
    Applicant: Novus International Inc.
    Inventor: Novus International Inc.
  • Publication number: 20130197258
    Abstract: The invention concerns a method for preparing acrolein from glycerol or glycerine, wherein dehydration of the glycerol or glycerine is achieved in the presence of a catalyst based on zirconium oxide and which active phase consists in at least a) a silicon oxide, a zirconium oxide and at least one metal M oxide, said metal being selected from tungsten, cerium, manganese, niobium, tantalum, vanadium and titanium, b) a titanium oxide, a zirconium oxide and at least one metal M oxide, said metal being selected from tungsten, cerium, manganese, niobium, tantalum, vanadium and silicon. This method can be used for making 3-(methylthio)propionic aldehyde MMP, 2-hydroxy-4-,methylthiobutyronitrile HMTBN, methionine and its analogs.
    Type: Application
    Filed: June 16, 2011
    Publication date: August 1, 2013
    Applicants: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, ADISSEO FRANCE S.A.S.
    Inventors: Pascaline Lauriol-Garbey, Virginie Belliere-Baca, Stéphane Loridant, Jean-Marc Millet
  • Publication number: 20130184474
    Abstract: The invention relates to a method for preparing an amino acid, or its salts, from 2-aminobutyrolactone (2ABL), said amino acid fitting the formula I, XCH2CH2CHNH2COOH, wherein X is such that X? represents a nucleophilic ion, according to which N-carboxylation of 2-aminobutyrolactone (2ABL) is achieved with carbon dioxide, and the thereby obtained 2ABL carbamate is reactive with an XH reagent or its salts.
    Type: Application
    Filed: October 4, 2011
    Publication date: July 18, 2013
    Applicant: ADISSEO FRANCE S.A.S.
    Inventors: Robert Huet, Jean-Michel Joerger, Vivien Henryon
  • Patent number: 8476427
    Abstract: Provided herein are processes for the production of methionine or selenomethionine from homoserine. In particular, the processes proceed via the production of carbamate intermediates.
    Type: Grant
    Filed: March 9, 2011
    Date of Patent: July 2, 2013
    Assignee: Novus International, Inc.
    Inventors: Stephen J. Lorbert, Kevin A. Trankler, Richard Vonder Embse, Dayna L. Turner, Tracy Rode, James C. Peterson
  • Publication number: 20130158292
    Abstract: A novel method capable of producing methionine without using hydrogen cyanide as a raw material has been desired. The present invention relates to a method for producing methionine including Step A of oxidizing 4-methylthio-2-oxo-1-butanal in the presence of an alcohol, and Step B of reductively aminating 4-methylthio-2-oxo-butyrate obtained in Step A. It is preferable that Step A is carried out by reacting 4-methylthio-2-oxo-1-butanal, the alcohol and an oxidizing agent in the presence of a carbene catalyst.
    Type: Application
    Filed: December 13, 2012
    Publication date: June 20, 2013
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: SUMITOMO CHEMICAL COMPANY, LIMITED
  • Publication number: 20130108560
    Abstract: A thin film composition for oral administration that adheres to and dissolves in a mouth of a user, wherein the thin film is a single layered water-soluble solid comprising at least one D-amino acid contained in a plurality of hydrophobic carriers dispersed throughout the thin film. The hydrophobic carriers comprise oil and the composition further comprises a phospholipid, an emulsifier, and a water soluble polymer. The preferred D-amino acids are D-leucine, D-tryptophan, D-methionine, and D-tyrosine. A method of reducing dental plaque in a subject entails placing the thin film composition contemplated herein into a mouth of the subject.
    Type: Application
    Filed: November 1, 2012
    Publication date: May 2, 2013
    Inventors: Robert Davidson, Eric Allen, Ed Maliski
  • Publication number: 20130072713
    Abstract: A novel method for producing methionine without using hydrogen cyanide as a raw material has been demanded. A method for producing methionine including a step A of oxidizing 4-methylthio-2-oxo-1-butanal in the presence of an alcohol; a step B of hydrolyzing a 4-methylthio-2-oxo-butanoic acid ester obtained in the step A; and a step C of subjecting 4-methylthio-2-oxo-butanoic acid obtained in the step B to reductive amination.
    Type: Application
    Filed: September 14, 2012
    Publication date: March 21, 2013
    Inventors: Koji HAGIYA, Kazuyasu TANI
  • Publication number: 20130012737
    Abstract: According to the present invention, a new process for producing a sulfur-containing amino acid without using of hydrogen cyanide or sodium azide which requires careful handling as a raw material can be provided. The present invention relates to a process for producing a sulfur-containing amino acid represented by the following formula (1) or a salt thereof: wherein R1 is an alkyl group having 1 to 12 carbon atoms and optionally having substituents or a cycloalkyl group having 3 to 12 carbon atoms and optionally having substituents, and n is an integral number of from 1 to 4, comprising a step of reacting a sulfur-containing 2-ketocarboxylic acid represented by the formula (2) or a salt thereof: wherein R1 and n mean the same as defined above, with ammonia and hydrogen in the presence of a transition metal catalyst.
    Type: Application
    Filed: March 24, 2011
    Publication date: January 10, 2013
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Kazuyasu Tani, Taro Hirose, Koji Hagiya
  • Publication number: 20130008384
    Abstract: An animal feed mixture containing DL-methionyl-DL-methionine and salts thereof for animals kept in aquacultures is provided. Methods for preparing DL-methionyl-DL-methionine of formula (I) and methods to fractionate the diasteriomeric forms obtained are also provided.
    Type: Application
    Filed: September 14, 2012
    Publication date: January 10, 2013
    Applicant: Evonik Degussa GmbH
    Inventors: Christoph KOBLER, Thomas Haeussner, Christoph Weckbecker
  • Publication number: 20130011514
    Abstract: An animal feed mixture containing DL-methionyl-DL-methionine and salts thereof for animals kept in aquacultures is provided. Methods for preparing DL-methionyl-DL-methionine of formula (I) and methods to fractionate the diasteriomeric forms obtained are also provided.
    Type: Application
    Filed: September 14, 2012
    Publication date: January 10, 2013
    Applicant: EVONIK DEGUSSA GmbH
    Inventors: Christoph KOBLER, Thomas Haeussner, Christoph Weckbecker
  • Publication number: 20130006014
    Abstract: Provided herein are processes for the production of methionine or selenomethionine from homoserine. In particular, the processes proceed via the production of lactone intermediates.
    Type: Application
    Filed: August 30, 2012
    Publication date: January 3, 2013
    Applicant: NOVUS INTERNATIONAL INC.
    Inventors: Stephen J. Lorbert, Kevin A. Trankler, Richard Vonder Embse, Dayna L. Turner, Tracy Rode, Cynthia K. Snoddy, James C. Peterson
  • Publication number: 20120329846
    Abstract: Disclosed is an agent for use in the treatment or prevention of inflammatory bowel disease. Also disclosed is an agent for inhibiting the production of TNF-?. A therapeutic or prophylactic agent for inflammatory bowel disease comprising at least one amino acid selected from the group consisting of lysine, histidine, phenylalanine, methionine, tryptophan, glutamine, glycine, cysteine, cystine and threonine, the amino acid being administered at a dose of 0.1 to 4000 mg/kg per day; and a TNF-? production inhibitor comprising an amino acid selected from the group consisting of histidine, phenylalanine and tryptophan, the amino acid being administered at a dose of 0.1 to 4000 mg/kg per day.
    Type: Application
    Filed: March 27, 2012
    Publication date: December 27, 2012
    Applicant: Ajinomoto Co., Inc.
    Inventors: Hideki Matsumoto, Tomohisa Okutsu, Tomoko Takeda, Hideki Suzuki, Tetsuo Yano, Masaki Hashimoto, Miho Ono, Manabu Suzuki
  • Publication number: 20120294866
    Abstract: The present invention provides a liquid pharmaceutical formulation comprising a therapeutic protein, a surfactant and at least an antioxidant selected from the group of radical scavengers, chelating agents or chain terminators.
    Type: Application
    Filed: January 14, 2010
    Publication date: November 22, 2012
    Applicant: F. HOFFMANN-LA ROCHE AG
    Inventors: Hanns-Christian Mahler, Satya Krishna Kishore Ravuri
  • Publication number: 20120253068
    Abstract: Provided is a process for producing methionine, which involves: (1) hydrolyzing 5-[2-(methylthio)ethylimidazolidine-2,4-dione in the presence of a basic potassium compound, (2) introducing carbon dioxide into a reaction liquid obtained in step (1), thereby precipitating methionine, and separating the resulting slurry into a precipitate and a mother liquid, (3) heat-treating the mother liquid obtained in step (2), and (4) introducing carbon dioxide into the mother liquid heat-treated in step (3), thereby precipitating methionine and potassium bicarbonate, and separating the resulting slurry into a precipitate and a mother liquid, wherein the alanine content in the mother liquid to be subjected to step (4) is 0.75 wt % or less.
    Type: Application
    Filed: March 27, 2012
    Publication date: October 4, 2012
    Inventors: Naoko IMADA, Yoshiyuki KOIZUMI
  • Publication number: 20120215022
    Abstract: A method for the production of 2-hydroxy-4-(methylthio)butyronitrile having good storage stability in a multi-zone reactor, is provided. 3-methylmercaptopropionaldehyde is reacted with hydrogen cyanide in the presence of a base as catalyst in a main reaction zone of the multizone reactor to form a reaction mixture comprising the 2-hydroxy-4-(methylthio)butyronitrile, unreacted 3-methylmercaptopropionaldehyde, the catalyst and residual amounts of gaseous hydrogen cyanide. The residual gaseous hydrogen cyanide is removed from the main reaction zone to an absorption and post-reaction zone of the reactor which comprises a mixture of 3-methylmercaptopropionaldehyde and the catalyst; and the gaseous hydrogen cyanide is further reacted with the 3-methylmercaptopropionaldehyde in the absorption and post reaction zone. A molar ratio of hydrogen cyanide to 3-(methylthio)propanal in the main reaction zone is from 0.98 to 1.03.
    Type: Application
    Filed: February 22, 2012
    Publication date: August 23, 2012
    Applicant: Evonik Degussa GmbH
    Inventors: Dieter Buss, Martin Steurenthaler, Michael R. Rinner, Stephan Kretz, Hans Joachim Hasselbach, Caspar-Heinrich Finkeldei, Martin Koerfer, Pablo Zacchi
  • Publication number: 20120215021
    Abstract: A storage stable mixture containing 86 to 97% by weight of 2-hydroxy-4-methylthiobutyronitrile, 2 to 14% by weight of water, 0.05 to 0.5% by weight of HCN and having a pH of 1 to 4, measured using a pH electrode at 23° C. is provided. A method to produce the storage stable mixture and its use in manufacture of DL-methionine or 2-hydroxy-4-methylthiobutyric acid is also provided.
    Type: Application
    Filed: February 22, 2012
    Publication date: August 23, 2012
    Applicant: Evonik Degussa GmbH
    Inventors: Dieter Buss, Martin Steurenthaler, Hans Joachim Hasselbach, Michael R. Rinner, Benjamin Fonfe, Martin Koerfer, Stephan Kretz
  • Publication number: 20120178966
    Abstract: A method comprising: (a) enzymatically processing an O-acetylhomoserine (OAHS) fermentation liquor to produce L-methionine and an acetate source; (b) separating at least a portion of said L-methionine from at least a fraction of said acetate source to form separated L-methionine and a residual liquor comprising an acetate-source; and (c) recovering at least a portion of said acetate source from said residual liquor as recovered acetate.
    Type: Application
    Filed: December 29, 2011
    Publication date: July 12, 2012
    Applicant: CJ CHEILJEDANG CORPORATION
    Inventors: Soon Won HONG, In Seok HWANG, Sang Mok LEE, Youn Jae LEE, Jun Young JUNG, Aharon Eyal
  • Patent number: 8217197
    Abstract: A process for producing methionine advantageously in view of cost, while efficiently recovering useful components, is provided, including the following steps (1) hydrolyzing 5-[2-(methylthio)ethyl]imidazolidine-2,4-dione in the presence of a basic potassium compound; (2) introducing carbon dioxide into the reaction solution obtained in step (1) to thereby precipitate methionine, and separating the resulting slurry into a precipitate and a mother liquor; (3) concentrating the mother liquor obtained in step (2), mixing the resulting concentrate with a lower alcohol, introducing carbon dioxide into the resulting mixture to thereby precipitate methionine and potassium hydrogencarbonate, and separating the resulting slurry into a precipitate and a mother liquor; and (4) concentrating the mother liquor obtained in step (3), treating the resulting concentrate by heating at a temperature of from 150 to 200° C., and recycling the treated solution for use in step (3).
    Type: Grant
    Filed: November 6, 2009
    Date of Patent: July 10, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiyuki Koizumi, Akinori Goto, Takushi Azemi
  • Publication number: 20120141590
    Abstract: Microspheres are produced by contacting a solution of a macromolecule or small molecule in a solvent with an antisolvent and a counterion, and chilling the solution. The microspheres are useful for preparing pharmaceuticals, nutraceuticals, cosmetic products and the like of defined dimensions.
    Type: Application
    Filed: September 30, 2011
    Publication date: June 7, 2012
    Inventors: Michael Malakhov, Fang Fang
  • Publication number: 20120123158
    Abstract: The present invention relates to a method for increasing L-methionine productivity and organic acid productivity. More particularly, the present invention relates to a method which involves adding a mixture containing methyl mercaptan and dimethyl sulfide at a appropriate ratio to O-acetyl homoserine or O-succinyl homoserine and to an enzyme having an activity of converting methionine precursor into L-methionine, so as to perform an enzyme reaction, to thereby improve the conversion rate of L-methionine and organic acid from the L-methionine precursor, and thus increasing L-methionine yield as compared to conventional method.
    Type: Application
    Filed: February 26, 2010
    Publication date: May 17, 2012
    Applicant: CJ CHEILJEDANG CORPORATION
    Inventors: So Young Kim, Yong Uk Shin, In Kyung Heo, Hyun Ah Kim, Ju Eun Kim, Chang Il Seo, Sung Kwang Son, Sang Mok Lee, Sung Hoo Jhon, Han Jin Lee, Kwang Ho Na, Il Chul Kim
  • Publication number: 20120058905
    Abstract: Naturally-occurring and modified recombinant nucleic acid molecules have been isolated that encode linear pre-cursors of cyclopeptides of the Caryophyllaceae (Ccps) and Caryophyllaceae-like (Clcps) type V1 class of cyclopeptides. Such nucleic acid molecules are useful for producing cyclopeptides and their linear precursors by recombinant methods.
    Type: Application
    Filed: May 10, 2010
    Publication date: March 8, 2012
    Inventors: Patrick S. Covello, Raju S.S. Datla, Sandra Lee Stone, J. John Balsevich, Martin John Reaney, Paul Grenville Arnison, Janet Anne Condie
  • Patent number: 8119837
    Abstract: A process for producing methionine, while corrosion of a pipe and a reaction vessel is well inhibited, is provided including the following steps (1) to (3), wherein a content of thiols in 3 -methylthiopropanal is 500 ppm or less, based on the propanal, and a content of hydrogen sulfide in 3-methylthiopropanal is 60 ppm or less, based on the propanal; step (1) in which 3 -methylthiopropanal is reacted with hydrogen cyanide in the presence of a base to give 2 -hydroxy -4-methylthiobutanenitrile; step (2) in which the 2-hydroxy-4-methylthiobutanenitrile obtained in step (1) is reacted with ammonium carbonate to give 5-(?-methylmercaptoethyl) hydantoin; and step (3) in which the 5-(?-methylmercaptoethyl)hydantoin obtained in step (2) is hydrolyzed in the presence of a basic potassium compound to give methionine.
    Type: Grant
    Filed: November 6, 2009
    Date of Patent: February 21, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takushi Azemi, Yoshiyuki Koizumi
  • Patent number: 8119836
    Abstract: Derivatives of seleno-alpha amino acids, particularly selenomethionine as enhanced bioavailable sources of selenium in animal diets.
    Type: Grant
    Filed: May 6, 2009
    Date of Patent: February 21, 2012
    Assignee: Zinpro Corporation
    Inventors: Mahmoud M. Abdel-Monem, Michael D. Anderson
  • Publication number: 20120041178
    Abstract: Provided are a coenzyme Q10 nanoparticle, a method of preparing the same and a composition having the nanoparticle. According to the present invention, Coenzyme Q10 may be dissolved in only a water-miscible organic solvent, and easily made into a nano-sized particle and solubilized under a low energy condition, for example, by simple stirring. The coenzyme Q10 may be dispersion-stabilized by an amino acid or protein. The coenzyme Q10 is formed in a nano-sized particle and solubilized, an absorption rate may be increased and simultaneously deliver the amino acid and protein with the nanoparticle. Thus, the coenzyme Q10 nanoparticle can be effectively used in food, cosmetics and medicine.
    Type: Application
    Filed: April 6, 2010
    Publication date: February 16, 2012
    Applicant: Korea Research Institute of Bioscience and Biotechnology
    Inventors: Bong Hyun Chung, Jung Hyun Han