Sulfur Patents (Class 562/581)
  • Patent number: 11766661
    Abstract: The present disclosure relates to a catalyst that includes a support that includes a metal oxide and a metal deposited on the support, where the metal oxide includes at least one of TiO2, Al2O3, SiO2, CeO2, and/or ZrO2, the metal includes at least one of Pt, Pd, Ru Rh, Ni, and/or Mo, the metal is in the form of a particle, and the metal is present on the support at a concentration between about 0.1 wt % and about 5.0 wt %.
    Type: Grant
    Filed: March 3, 2021
    Date of Patent: September 26, 2023
    Assignee: Alliance for Sustainable Energy, LLC
    Inventors: Michael Brandon Griffin, Calvin Mukarakate, Maarit Kristiina Iisa, Abhijit Dutta, Joshua A. Schaidle, Andrew Nolan Wilson, Mark R. Nimlos, Matthew Maurice Yung
  • Patent number: 11242316
    Abstract: A method for manufacturing 2-hydroxy-4-(methylthio)butyric acid (HMTBA) from 2-hydroxy-4-methylthio-butyronitrile (HMTBN), where HMTBN is hydrolyzed into HMTBA in the presence of a mineral acid in an aqueous medium, the medium is neutralized by addition of a base, a first phase including at least HMTBA and salts and a second phase containing salts are separated, the method including the separation of the HMTBA from the salts of the first phase, by subjecting the latter to a chromatography.
    Type: Grant
    Filed: March 9, 2018
    Date of Patent: February 8, 2022
    Assignee: ADISSEO FRANCE S.A.S.
    Inventors: Virginie Belliere-Baca, Didier Morvan
  • Patent number: 9365877
    Abstract: The present invention relates to a method for producing L-methionine using a bio-synthesis process and a specific enzymatic process. More particularly, the present invention relates to a method for producing L-methionine with high yield by enzyme conversion reaction from L-methionine precursor in the presence of methyl mercaptan (CH3SH). The process of the present invention enables selective production of L-methionine which may be used in various fields of industry, such as feed- and food-additives, as raw material for medical supplies, pharmaceutical drugs, and the like.
    Type: Grant
    Filed: September 2, 2011
    Date of Patent: June 14, 2016
    Assignees: CJ CHEILJEDANG CORPORATION, ARKEMA FRANCE
    Inventors: Georges Fremy, Patrice Barre, So Young Kim, Sung Kwang Son, Sang Mok Lee
  • Patent number: 9206121
    Abstract: A method to produce D,L-Methionine from 2-hydroxy-4-(methylthio)butyronitrile by reaction with ammonia, optionally in the presence of carbon dioxide, is provided. The 2-hydroxy-4-(methylthio)butyronitrile is obtained by reaction of 3-methylmercaptopropionaldehyde with hydrogen cyanide in the presence of a base as catalyst in a main reaction zone of a multizone reactor. 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: March 27, 2015
    Date of Patent: December 8, 2015
    Assignee: 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: 9133113
    Abstract: A method for the production of 2-hydroxy-4-methylthiobutyric acid by hydrolysis of 2-hydroxy-4-(methylthio)butyronitrile 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: March 27, 2014
    Date of Patent: September 15, 2015
    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: 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
  • Patent number: 8962884
    Abstract: The invention concerns a method for preparing a complex of an acid chosen from among methionine, 2-hydroxy-4-methylthiobutanoic acid (HMTBA) and lactic acid, and of at least one metal, starting from said acid and a mineral metal source, wherein the acid is caused to react with the mineral metal source in an extruder.
    Type: Grant
    Filed: September 21, 2011
    Date of Patent: February 24, 2015
    Assignee: Adisseo Ireland Limited
    Inventors: Jean-Claude Le Thiesse, Patrick Rey, Vivien Henryon
  • 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
  • Publication number: 20130274510
    Abstract: The present invention relates to a process for the synthesis of polyhydroxyalkanoates (PHAs) and PHAs obtained by the said process and the use of the said PHAs. The PHAs of the present invention, called PHACOS, have a novel monomeric composition, as they contain monomers with thioester groups in the side chain that confer new physicochemical properties and allow subsequent chemical modification.
    Type: Application
    Filed: September 20, 2011
    Publication date: October 17, 2013
    Applicant: CONSEJO SUPERIOR DE INVESTIGACIONES CIENTÍFICAS (CSIC)
    Inventors: Isabel Fernandez Escapa, Ma del Valle Morales Ruiz, Jose Luis Garcia Lopez, Ma Auxiliadora Prieto Jimenez
  • 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: 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: 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: 20130177961
    Abstract: Multi-armed, monofunctional, and hydrolytically stable polymers are described having the structure wherein Z is a moiety that can be activated for attachment to biologically active molecules such as proteins and wherein P and Q represent linkage fragments that join polymer arms polya and polyb, respectively, to central carbon atom, C, by hydrolytically stable linkages in the absence of aromatic rings in the linkage fragments. R typically is hydrogen or methyl, but can be a linkage fragment that includes another polymer arm. A specific example is an mPEG disubstituted lysine having the structure where mPEGa and mPEGb have the structure CH3O—(CH2CH2O)nCH2CH2— where n may be the same or different for polya- and polyb- and can be from 1 to about 1,150 to provide molecular weights of from about 100 to 100,000.
    Type: Application
    Filed: December 14, 2012
    Publication date: July 11, 2013
    Applicant: NEKTAR THERAPEUTICS
    Inventor: NEKTAR THERAPEUTICS
  • Publication number: 20130172617
    Abstract: The invention concerns a method for preparing a complex of an acid chosen from among methionine, 2-hydroxy-4-methylthiobutanoic acid (HMTBA) and lactic acid, and of at least one metal, starting from said acid and a mineral metal source, wherein the acid is caused to react with the mineral metal source in an extruder.
    Type: Application
    Filed: September 21, 2011
    Publication date: July 4, 2013
    Applicant: ADISSEO IRELAND LIMITED
    Inventors: Jean-Claude Le Thiesse, Patrick Rey, Vivien Henryon
  • Publication number: 20120329731
    Abstract: In one embodiment the invention provides a method of combating cyanide poisoning, which comprises administering to a subject a compound capable of releasing 3-mercapto-pyruvate in vivo. In other embodiments the invention also provides pharmaceutical compositions comprising a compound capable of releasing 3-mercaptopyruvate in vivo, as well as novel compounds that are capable of releasing 3-mercaptopyruvate in vivo.
    Type: Application
    Filed: October 13, 2011
    Publication date: December 27, 2012
    Inventors: Herbert T. Nagasawa, David J.W. Goon, Daune L. Crankshaw, Robert Vince
  • Patent number: 8283278
    Abstract: The present invention relates to a process for sulfurizing a hydrocarbon treatment catalyst, comprising: at least a first step of depositing, on the surface of the catalyst, one or more sulfurization auxiliaries of formula (I): and at least a second step of placing the catalyst in contact with a sulfur-containing gaseous mixture containing hydrogen and a sulfur compound.
    Type: Grant
    Filed: September 10, 2010
    Date of Patent: October 9, 2012
    Assignee: Eurecat S.A.
    Inventors: Pierre Dufresne, Eric Nagy, Pauline Galliou
  • 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: 20110124844
    Abstract: Aspects of the present invention are directed to novel methods for making discrete polyethylene compounds selectively and specifically to a predetermined number of ethylene oxide units. Methods which can be used to build up larger dPEG compounds (a) containing a wider range of utility to make useful homo- and heterofunctional and branched species, and (b) under reaction configurations and conditions that are milder, more efficient, more diverse in terms of incorporating useful functionality, more controllable, and more versatile then any conventional method reported in the art to date. In addition, the embodiments of the invention allow for processes that allow for significantly improving the ability to purify the intermediates or final product mixtures, making these methods useful for commerial manufacturing dPEGs. Protecting groups and functional groups can be designed to make purification at large scale a practical reality.
    Type: Application
    Filed: January 27, 2011
    Publication date: May 26, 2011
    Inventors: Paul D. Davis, Edward C. Crapps
  • Publication number: 20110092360
    Abstract: The present invention relates to a process for sulfurizing a hydrocarbon treatment catalyst, comprising: at least a first step of depositing, on the surface of the catalyst, one or more sulfurization auxiliaries of formula (I): and at least a second step of placing the catalyst in contact with a sulfur-containing gaseous mixture containing hydrogen and a sulfur compound.
    Type: Application
    Filed: September 10, 2010
    Publication date: April 21, 2011
    Applicant: Eurecat S.A.
    Inventors: Pierre Dufresne, Eric Nagy, Pauline Galliou
  • Publication number: 20100298603
    Abstract: Provided is a process for producing an amide (A): by hydrating a nitrile (B) at high conversion in relatively short period of time even without use of high-capacity cooling apparatuses (25, 35) and a large amount of inorganic acid (D). In the process for the present invention, a nitrile (B) is hydrated in continuous mode in the presence of an inorganic acid (D) so as to give a conversion of 80% to 98%, and the unreacted nitrile contained in the resultant hydrated reaction liquid (E) is hydrated in batch-wise mode so as to give a conversion of 99.9% or more, thereby producing an amide (A). For example, the inorganic acid (D) is sulfuric acid and the use amount thereof is 0.5 to 1-fold mol with respect to the nitrile (B), and the temperature in hydration is 40 to 70-C, and hydration is performed in continuous mode using a tubular reactor (2c), loop reactor (2d) and the like. The resultant amide (A) can be hydrolyzed to produce a thiobutanoic acid (G).
    Type: Application
    Filed: January 9, 2009
    Publication date: November 25, 2010
    Inventors: Takanori Ito, Masahiro Kinoshita
  • Publication number: 20100094050
    Abstract: A method is provided of using a highly impact-resistant and corrosion-resistant alloy material for an apparatus for use in hydration of 2-hydroxy-4-methylthiobutanenitrile to obtain 2-hydroxy-4-methylthiobutanamide, the material being readily fabricated for an apparatus with a complicated structure and being composed of an alloy which contains 16.0 to 22.0% by weight of a Cr element, 16.0 to 22.0% by weight of a Mo element, 1.0 to 2.5% by weight of a Ta element and a Ni element as the rest, or an alloy which contains 26.0 to 32.0% by weight of a Mo element and a Ni element as the rest.
    Type: Application
    Filed: October 9, 2009
    Publication date: April 15, 2010
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Kazuo FUJITA, Kozo ONISHI
  • Publication number: 20090318715
    Abstract: The present invention relates to a process for preparing compounds of the formula (I) by reacting compounds of the formula (II) with thiolates (RS)nM. The present invention further relates to a process for preparing compounds of the formula (II) from ?-butyrolactone.
    Type: Application
    Filed: August 15, 2007
    Publication date: December 24, 2009
    Inventors: Patrick Deck, Kai Michael Exner, Boris Buschhaus
  • Publication number: 20090197865
    Abstract: In one embodiment the invention provides a method of combating cyanide poisoning, which comprises administering to a subject a compound capable of releasing 3-mercapto-pyruvate in vivo. In other embodiments the invention also provides pharmaceutical compositions comprising a compound capable of releasing 3-mercaptopyruvate in vivo, as well as novel compounds that are capable of releasing 3-mercaptopyruvate in vivo.
    Type: Application
    Filed: June 28, 2007
    Publication date: August 6, 2009
    Inventors: Herbert T. Nagasawa, David J.W. Goon, Daune L. Crankshaw, Robert Vince
  • Patent number: 7498456
    Abstract: Dithiocarbonate derivatives are disclosed, along with a process for preparing the same. The dithiocarbonate compounds can be utilized as initators, chain transfer agents and/or terminators in controlled free radical polymerizations. The dithiocarbonates can be used to produce polymers having narrow molecular weight distribution. Advantageously, the compounds of the present invention can also introduce functional groups into the resulting polymers. The dithiocarbonate compounds have low odor and are substantially colorless.
    Type: Grant
    Filed: March 21, 2007
    Date of Patent: March 3, 2009
    Assignee: Lubrizol Advanced Materials, Inc.
    Inventor: John Ta-Yuan Lai
  • Publication number: 20090053781
    Abstract: A method for producing 2-hydroxy-4-(methylthio)butyric acid which comprises the following steps (A), (B) and (C): Step (A): step of reacting 1,2-epoxy-3-butene with water to obtain 3-butene-1,2-diol, Step (B): step of reacting 3-butene-1,2-diol with methanethiol to obtain 4-(methylthio)butane-1,2-diol, Step (C): step of oxidizing 4-(methylthio)butane-1,2-diol to obtain 2-hydroxy-4-(methylthio)butyric acid.
    Type: Application
    Filed: October 13, 2005
    Publication date: February 26, 2009
    Inventors: Koji Hagiya, Hiroyuki Asako
  • Patent number: 7495128
    Abstract: A s,s?-bis-(?, ??-disubstituted-??-acetic acid)-trithiocarbonate and derivatives thereof can be used as an initiator, chain transfer agent, or terminator for polymerization of monomers such as free radical polymerizable monomers. Homopolymers, copolymers, and the like as well as block copolymers can be made utilizing the trithiocarbonate compound such as in a living free radical polymerization as well as to form telechelic polymers.
    Type: Grant
    Filed: August 28, 2007
    Date of Patent: February 24, 2009
    Assignee: Lubrizol Advanced Materials, Inc.
    Inventor: John Ta-Yuan Lai
  • Patent number: 7485748
    Abstract: A process for preparing 2-hydroxy-4-methylthiobutyric acid ammonium salt involves reacting 3-methylthiopropionaldehyde with hydrogen cyanide to form 2-hydroxy-4-methylthiobutyronitrile, and subsequently hydrolyzing the 2-hydroxy-4-methylthiobutyronitrile by catalytic hydrolysis to form the ammonium salt of the 2-hydroxy-4-methylthiobutyric acid in a single process step. One catalyst may be used in the hydrolysis for the whole reaction. The catalyst is preferably a solid containing a titanium compound such as, e.g., titanium nitride, titanium sulfide or titanium dioxide. The 2-hydroxy-4-methylthiobutyric acid ammonium salt produced by this process is nutritional and can be used as an additive in feedstuffs.
    Type: Grant
    Filed: March 26, 2004
    Date of Patent: February 3, 2009
    Assignee: Degussa AG
    Inventors: Horst Weigel, Christoph Weckbecker, Klaus Huthmacher
  • Patent number: 7465827
    Abstract: The present invention provides a process for producing 2-hydroxy-4-methylthiobutyric acid comprising the following steps (1) to (4): (1): hydrolyzing 2-hydroxy-4-methylthiobutyronitrile in the presence of sulfuric acid, (2): separating the reaction mixture obtained in the step (1) into an oil layer containing 2-hydroxy-4-methylthiobutyric acid and a water layer, (3): concentrating the oil layer obtained in the step (2), and (4) heating the concentrated product obtained in the step (3).
    Type: Grant
    Filed: August 12, 2005
    Date of Patent: December 16, 2008
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toru Haga, Tetsuya Shiozaki
  • Publication number: 20070149741
    Abstract: The present invention is directed to a free radical control agent of the structural formula: wherein R1 is a divalent alkyl group of 1 to 12 carbon atoms, R2 and R3 are each independently hydrogen or an alkyl group of 1 to 12 carbon atoms, and R4 is —OH or —COOH, with the proviso that the total carbon atoms of R1, R2, and R3 is no greater than 12; and wherein Y represents a functional group that is capable of activating a vinylic carbon toward free radical addition.
    Type: Application
    Filed: October 19, 2006
    Publication date: June 28, 2007
    Inventor: Dane Kenton Parker
  • Patent number: 7230063
    Abstract: The present invention is directed to a free radical control agent of the structural formula: wherein R1 is a divalent alkyl group of 1 to 12 carbon atoms, R2 and R3 are each independently hydrogen or an alkyl group of 1 to 12 carbon atoms, and R4 is —OH or —COOH, with the proviso that the total carbon atoms of R1, R2, and R3 is no greater than 12; and wherein Y represents a functional group that is capable of activating a vinylic carbon toward free radical addition.
    Type: Grant
    Filed: October 19, 2006
    Date of Patent: June 12, 2007
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Dane Kenton Parker
  • Patent number: 7220877
    Abstract: A novel class of dicarboxylic acid derivatives, the use of these compounds as pharmaceutical compositions, pharmaceutical compositions comprising the compounds and methods of treatment employing these compounds and compositions. The present compounds may be useful in the treatment and/or prevention of conditions mediated by Peroxisome Proliferator-Activated Receptors (PPAR).
    Type: Grant
    Filed: October 16, 2002
    Date of Patent: May 22, 2007
    Assignee: Novo Nordisk A/S
    Inventors: Per Sauerberg, Paul Stanley Bury, Lone Jeppesen, John Patrick Mogensen
  • Patent number: 7205368
    Abstract: Dithiocarbonate derivatives are disclosed, along with a process for preparing the same. The dithiocarbonate compounds can be utilized as initators, chain transfer agents and/or terminators in controlled free radical polymerizations. The dithiocarbonates can be used to produce polymers having narrow molecular weight distribution. Advantageously, the compounds of the present invention can also introduce functional groups into the resulting polymers. The dithiocarbonate compounds have low odor and are substantially colorless.
    Type: Grant
    Filed: October 23, 2002
    Date of Patent: April 17, 2007
    Assignee: Noveon, Inc.
    Inventor: John Ta-Yuan Lai
  • Patent number: 7148379
    Abstract: A process for the preparation of 2-hydroxy-4-methylthiobutyric acid.
    Type: Grant
    Filed: August 25, 2005
    Date of Patent: December 12, 2006
    Assignee: Degussa AG
    Inventors: Alexander Möller, Hans-Albrecht Hasseberg, Harald Heinzel, Volker Häfner
  • Patent number: 6903234
    Abstract: A method of making calcium-2-hydroxy-4-(mercaptomethyl)butanoate includes combining and mixing 2-hydroxy-4-(mercaptomethyl)butanoic acid and a calcium salt selected from calcium oxide and calcium hydroxide and water in a first reaction zone. The combining and mixing step is carried out over a first period of 3-120 seconds. The resulting reaction mixture is transferred at the end of the first period from the first reaction zone to a second reaction zone, the transferring step being carried out over a second period of 3-60 seconds. Heat generated by reaction between the 2-hydroxy-4-(mercaptomethyl)butanoic acid and the calcium salt in the second reaction zone is allowed to drive off sufficient water to produce a product mixture containing less than 5% (m/m) water.
    Type: Grant
    Filed: November 7, 2001
    Date of Patent: June 7, 2005
    Assignee: Technical and Commercial Services International Limited
    Inventors: Roger G. Dakin, Sarel W. Du Toit, Richard A. Houseman, David G. Stedman
  • Patent number: 6815560
    Abstract: The invention relates to a new process for the preparation of hydroxymethylthiobutyric acid by sulphuric hydrolysis of hydroxymethylthiobutyronitrile.
    Type: Grant
    Filed: July 9, 1999
    Date of Patent: November 9, 2004
    Assignee: Rhone-Poulenc Agro
    Inventors: Michel Garrait, Georges Gros
  • Patent number: 6743946
    Abstract: The invention concerns an improved method for separating hydroxymethylthiobutyric acid by neutralising hydroxymethylthiobutyronitrile sulphuric hydrolysate, decanting and treating each phase with an organic solvent.
    Type: Grant
    Filed: January 8, 2001
    Date of Patent: June 1, 2004
    Assignee: Adisseo Ireland Limited
    Inventors: Frédéric Carencotte, Michel Garrait, Georges Gros
  • Publication number: 20040054225
    Abstract: A method of making calcium-2-hydroxy-4-(mercaptomethyl)butanoate includes combining and mixing 2-hydroxy-4-(mercaptomethyl)butanoic acid and a calcium salt selected from calcium oxide and calcium hydroxide and water in a first reaction zone. The combining and mixing step is carried out over a first period of 3-120 seconds. The resulting reaction mixture is transferred at the end of the first period from the first reaction zone to a second reaction zone, the transferring step being carried out over a second period of 3-60 seconds. Heat generated by reaction between the 2-hydroxy-4-(mercaptomethyl)butanoic acid and the calcium salt in the second reaction zone is allowed to drive off sufficient water to produce a product mixture containing less than 5% (m/m) water.
    Type: Application
    Filed: September 19, 2003
    Publication date: March 18, 2004
    Inventors: Roger G. Dakin, Sarel W. Du Toit, Richard A. Houseman, David G. Stedman
  • Patent number: 6703422
    Abstract: The present invention relates to novel sulfide and disulfide compounds, compositions comprising sulfide and disulfide compounds, and methods useful for treating and preventing cardiovascular diseases, dyslipidemias, dysproteinemias, and glucose metabolism disorders comprising administering a composition comprising an ether compound. The compounds, compositions, and methods of the invention are also useful for treating and preventing Alzheimer's Disease, Syndrome X, peroxisome proliferator activated receptor-related disorders, septicemia, thrombotic disorders, obesity, pancreatitis, hypertension, renal disease, cancer, inflammation, and impotence. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.
    Type: Grant
    Filed: October 11, 2001
    Date of Patent: March 9, 2004
    Assignee: Esperion Therapeutics, Inc.
    Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
  • Patent number: 6660880
    Abstract: A process, for the preparation of an ester of 2-hydroxy-4-methylthiobutyric acid which is substantially in the monomeric form, which process, being capable of industrial application and which comprises reacting 2-hydroxy-4-methylthiobutyric acid with an alcohol in the presence of water and an acid catalyst at a temperature of from 30 to 150° C. wherein the acid is the direct product of the hydrolysis of 2-hydroxy-4-methylthiobutyronitrile.
    Type: Grant
    Filed: February 7, 2001
    Date of Patent: December 9, 2003
    Assignee: Adisseo Ireland Limited
    Inventors: Michel Garrait, Claude Casse, George Gros
  • Patent number: 6649794
    Abstract: A method for producing a 2-hydroxy-4-methylthiobutanoic acid is provided, the method comprising the steps of: hydrolyzing a 2-hydroxy-4-methylthiobutanenitrile and/or a 2-hydroxy-4-methylthiobutanamide in the presence of a sulfuric acid to obtain a reaction mixture containing a 2-hydroxy-4-methylthiobutanoic acid; mixing the reaction mixture with a basic alkaline metal compound to obtain a mixture comprising an oil layer containing the 2-hydroxy-4-methylthiobutanoic acid and a water layer; and separating the oil layer containing the 2-hydroxy-4-methylthiobutanoic acid from the mixture. In accordance with the present invention, a 2-hydroxy-4-methylthiobutanoic acid is obtained with excellent operability and efficiency without using an organic solvent.
    Type: Grant
    Filed: August 2, 2002
    Date of Patent: November 18, 2003
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kenji Ikudome, Tetsuya Shiozaki
  • Patent number: 6627773
    Abstract: A process for producing 2-hydroxy-4-methylthiobutanoic acid is provided wherein 2-hydroxy-4-methylthiobutyronitrile is converted to 2-hydroxy-4-methylthiobutanamide by using sulfuric acid, then adding an aqueous solution containing ammonium bisulfate and ammonium sulfate to the reaction liquid to obtain an oil layer containing 2-hydroxy-4-methylthiobutanoic acid and an aqueous layer containing ammonium bisulfate and ammonium sulfate, then a part of the ammonium salts is separated from the aqueous layer, and the aqueous layer containing ammonium bisulfate and ammonium sulfate thus obtained is recycled as the aqueous solution containing ammonium bisulfate and ammonium sulfate described above. According to the present invention, 2-hydroxy-4-methylthiobutanoic acid of high quality can be obtained without requiring organic solvents and with a greatly reduced amount of waste water.
    Type: Grant
    Filed: June 28, 2001
    Date of Patent: September 30, 2003
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kenji Ikudome, Tetsuya Shiozaki
  • Patent number: 6596899
    Abstract: A s,s′-bis-(&agr;,&agr;′-disubstituted-&agr;″-acetic acid)-trithiocarbonatte and derivatives thereof can be used as an initiator, chain transfer agent, or terminator for polymerization of monomers such as free radical polymerizable monomers. Homopolymers, copolymers, and the like as well as block copolymers can be made utilizing the trithio carbonate compound such as in a living free radical polymerization as well as to form telechelic polymers.
    Type: Grant
    Filed: February 16, 2000
    Date of Patent: July 22, 2003
    Assignee: Noveon IP Holdings Corp.
    Inventor: John T. Lai
  • Patent number: 6548701
    Abstract: A process for the continuous preparation of 3-(methylthio)propanal. A liquid reaction medium is contacted with a gaseous acrolein feed stream in a gas/liquid contact zone. The reaction medium contains 3-(methylthio)propanal, methyl mercaptan and a catalyst for the reaction between methyl mercaptan and acrolein. The gaseous acrolein feed stream comprises acrolein vapor and non-condensable gas. Acrolein is transferred from the acrolein feed stream to the reaction medium and reacts with methyl mercaptan in that medium to produce a liquid reaction product containing 3-(methylthio)propanal. The non-condensable gas is separated from the liquid reaction product. The reaction product is divided into a product fraction and a circulating fraction, and the circulating fraction is recycled to the gas/liquid contact zone.
    Type: Grant
    Filed: October 5, 2001
    Date of Patent: April 15, 2003
    Assignee: Novus International, Inc.
    Inventors: Yung C. Hsu, Dennis A. Ruest
  • Patent number: 6479695
    Abstract: A process for the preparation of 2-hydroxy-4-methylthiobutyric acid ester which comprises (a) a first step of reacting 2-hydroxy-4-methylthiobutyronitrile with sulphuric acid to produce 2-hydroxy-4-methylthiobutyramide, and (b) a second step of reacting the 2-hydroxy-4-methylthiobutyramide with an alcohol to produce a 2-hydroxy-4-methylthiobutyric acid ester, the two steps being carried out in the same reaction medium.
    Type: Grant
    Filed: December 28, 2001
    Date of Patent: November 12, 2002
    Assignee: Aventis Animal Nutrition, S.A.
    Inventors: Michel Garrait, Claude Casse, Georges Gros
  • Patent number: 6458997
    Abstract: A continuous process for the preparation of 2-hydroxy-4-methylthiobutanoic acid which includes introducing sulfuric acid into a first reactor including a continuous stirred tank reactor and introducing 2-hydroxy-4-methylthiobutanenitrile into the first reactor. 2-hydroxy-4-methylthiobutanenitrile is continually hydrolyzed within the first reactor to produce an intermediate aqueous hydrolysis solution containing 2-hydroxy-4-methylthiobutanamide. The intermediate aqueous hydrolysis solution is continuously introduced into a plug flow reactor. 2-hydroxy-4-methylthiobutanamide is continually hydrolyzed within the plug flow reactor to produce an aqueous hydrolyzate product solution containing 2-hydroxy-4-methylthiobutanoic acid. 2-hydroxy-4-methylthiobutanoic acid is recovered from the aqueous hydrolyzate product solution.
    Type: Grant
    Filed: December 22, 2000
    Date of Patent: October 1, 2002
    Assignee: Novus International, Inc.
    Inventors: Yung C. Hsu, Thomas F. Blackburn, Paul F. Pellegrin, Allen H. Kranz, James M. Willock
  • Patent number: 6437177
    Abstract: The present invention provides a compound of formula I or pharmaceutical acceptable salts thereof wherein R1 is C4-12 alkyl, C4-12 alkenyl, C4-12 alkynyl, —(CH2)h—C3-8 cycloalkyl, substituted and unsubstituted —(CH2)h-aryl, substituted and unsubstituted —(CH2)h-het, R2 is substituted and unsubstituted C1-12 alkyl, substituted and unsubstituted C2-12 alkenyl, substituted and unsubstituted C2-12 alkynyl, substituted and unsubstituted —(CH2)h—C3-8 cycloalkyl, substituted and unsubstituted —(CH2)h—C3-8 cycloalkenyl, substituted and unsubstituted —(CH2)h-aryl, substituted and unsubstituted —(CH2)h-heterocyclic ring, substituted and unsubstituted —(CH2)i—X—R4 (X is —O—, —S(═O)j—, —NR7—, —S(═O)2NR8—, or —C(═O)—), and —(CH2)iCHR5R6. The compounds are inhibitors of matrix metalloproteinases involved in tissue degradation.
    Type: Grant
    Filed: November 20, 1998
    Date of Patent: August 20, 2002
    Inventors: Martha A. Warpehoski, Mark Allen Mitchell, Donald E. Harper, Linda Louise Maggiora
  • Patent number: 6353012
    Abstract: HETE derivatives and methods of their use for treating dry eye are disclosed.
    Type: Grant
    Filed: October 23, 2000
    Date of Patent: March 5, 2002
    Assignee: Alcon Universal Ltd.
    Inventors: Mark R. Hellberg, John M. Yanni, Gustav Graff, Daniel A. Gamache, Peter G. Klimko
  • Patent number: 6331566
    Abstract: Heteroatom-interrupted HETE derivatives and methods of their use for treating dry eye are disclosed.
    Type: Grant
    Filed: October 23, 2000
    Date of Patent: December 18, 2001
    Assignee: Alcon Universal Ltd.
    Inventors: Raymond E. Conrow, Peter G. Klimko
  • Patent number: 6320076
    Abstract: A process for the continuous preparation of 3-(methylthio)propanal. A liquid reaction medium is contacted with a gaseous acrolein feed stream in a gas/liquid contact zone. The reaction medium contains 3-(methylthio)propanal, methyl mercaptan and a catalyst for the reaction between methyl mercaptan and acrolein. The gaseous acrolein feed stream comprises acrolein vapor and non-condensable gas. Acrolein is transferred from the acrolein feed stream to the reaction medium and reacts with methyl mercaptan in that medium to produce a liquid reaction product containing 3-(methylthio)propanal. The non-condensable gas is separated from the liquid reaction product. The reaction product is divided into a product fraction and a circulating fraction, and the circulating fraction is recycled to the gas/liquid contact zone.
    Type: Grant
    Filed: December 22, 1999
    Date of Patent: November 20, 2001
    Assignee: Novus International, Inc.
    Inventors: Yung C. Hsu, Dennis A. Ruest
  • Patent number: 6268531
    Abstract: A continuous process for the preparation of 2-hydroxy-4-methylthiobutanoic acid or a salt thereof which includes introducing an aqueous mineral acid into a nitrile hydrolysis reactor including a continuous stirred tank reactor and introducing 2-hydroxy-4-methylthiobutanenitrile into the nitrile hydrolysis reactor. 2-hydroxy-4-methylthiobutanenitrile is continually hydrolyzed within the nitrile hydrolysis reactor to produce a nitrile hydrolysis reactor product stream containing 2-hydroxy-4-methylthiobutanamide. The nitrile hydrolysis reactor product stream is continuously introduced into an amide hydrolysis flow reactor. 2-hydroxy-4-methylthiobutanamide is continually hydrolyzed within the amide hydrolysis flow reactor to produce an aqueous hydrolyzate product containing 2-hydroxy-4-methylthiobutanoic acid. 2-hydroxy-4-methylthiobutanoic acid is recovered from the aqueous hydrolyzate product.
    Type: Grant
    Filed: October 2, 1998
    Date of Patent: July 31, 2001
    Assignee: Novus International, Inc.
    Inventors: Yung C. Hsu, Thomas F. Blackburn, Paul F. Pellegrin, Allen H. Kranz, James M. Willock