CA1263668C - 2-HYDROXY-METHYLTHIOBUTYRIC ACID AND PREPARATION METHOD - Google Patents

2-HYDROXY-METHYLTHIOBUTYRIC ACID AND PREPARATION METHOD

Info

Publication number
CA1263668C
CA1263668C CA467699A CA467699A CA1263668C CA 1263668 C CA1263668 C CA 1263668C CA 467699 A CA467699 A CA 467699A CA 467699 A CA467699 A CA 467699A CA 1263668 C CA1263668 C CA 1263668C
Authority
CA
Canada
Prior art keywords
hydroxy
acid
liquid
weight
preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
CA467699A
Other languages
English (en)
French (fr)
Other versions
CA1263668A (en
Inventor
Dennis Anna Ruest
Masaharu Takano
Lawrence Russell Wolf
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed filed Critical
Priority to CA467699A priority Critical patent/CA1263668C/en
Application granted granted Critical
Publication of CA1263668A publication Critical patent/CA1263668A/en
Publication of CA1263668C publication Critical patent/CA1263668C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/26—Separation; Purification; Stabilisation; Use of additives
    • C07C319/28—Separation; Purification
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/105—Aliphatic or alicyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/142—Amino acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/70—Feeding-stuffs specially adapted for particular animals for birds
    • A23K50/75—Feeding-stuffs specially adapted for particular animals for birds for poultry
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Animal Husbandry (AREA)
  • Food Science & Technology (AREA)
  • Birds (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fodder In General (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA467699A 1983-11-14 1984-11-13 2-HYDROXY-METHYLTHIOBUTYRIC ACID AND PREPARATION METHOD Expired CA1263668C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA467699A CA1263668C (en) 1983-11-14 1984-11-13 2-HYDROXY-METHYLTHIOBUTYRIC ACID AND PREPARATION METHOD

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US06/550,857 US4524077A (en) 1983-11-14 1983-11-14 Liquid 2-hydroxy-4-methylthiobutyric acid and process for the preparation thereof
US550,857 1983-11-14
CA467699A CA1263668C (en) 1983-11-14 1984-11-13 2-HYDROXY-METHYLTHIOBUTYRIC ACID AND PREPARATION METHOD

Publications (2)

Publication Number Publication Date
CA1263668A CA1263668A (en) 1989-12-05
CA1263668C true CA1263668C (en) 1989-12-05

Family

ID=24198852

Family Applications (1)

Application Number Title Priority Date Filing Date
CA467699A Expired CA1263668C (en) 1983-11-14 1984-11-13 2-HYDROXY-METHYLTHIOBUTYRIC ACID AND PREPARATION METHOD

Country Status (13)

Country Link
US (1) US4524077A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EP (1) EP0142488B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
JP (2) JPS60156396A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
KR (1) KR870000657B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AT (1) ATE29131T1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AU (1) AU562078B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CA (1) CA1263668C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE (1) DE3465592D1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
GB (1) GB2149791B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
GE (1) GEP19960463B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
MX (1) MX163989B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
SU (1) SU1428193A3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ZA (1) ZA848847B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

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ES2005784A6 (es) * 1988-02-22 1989-03-16 Desarrollo Tecnico Ind S A Soc Un procedimiento para preparar soluciones acuosas de acido 2-hidroxi-4-metil-tiobutirico.
MY109603A (en) * 1992-05-21 1997-03-31 Daicel Chem Process for producing 2-hydroxy-4-methylthiobutanoic acid
US5498790A (en) * 1993-06-09 1996-03-12 Novus International, Inc. Regeneration of sulfuric acid from sulfate by-products of 2-hydroxy-4-(methylthio)butyric acid manufacture
WO1996001809A1 (de) * 1994-07-11 1996-01-25 Degussa Aktiengesellschaft Verfahren zur gewinnung von 2-hydroxy-4-methylthiobuttersäure (mha), mha und dessen verwendung
DE4428608C1 (de) * 1994-08-12 1996-02-29 Degussa Verfahren zur Gewinnung von 2-Hydroxy-4-methylthiobuttersäure (MHA)
US5856567A (en) * 1995-06-07 1999-01-05 Novus International, Inc. Continuous hydrolysis process for preparing 2-hydroxy-4-methylthiobutanioc acid or salts thereof
ES2164244T3 (es) 1995-06-07 2002-02-16 Novus Int Inc Procedimiento de hidrolisis en continuo para la preparacion de acido 2-hidroxi-4-metiltiobutanoico y sales del mismo.
DE19548538C2 (de) * 1995-12-23 1997-12-18 Degussa Verfahren zur Gewinnung von 2-Hydroxy-4-methylthiobuttersäure (MHA)
DE19654485A1 (de) * 1996-12-27 1998-07-02 Degussa Verfahren zur Gewinnung von lagerstabiler 2-Hydroxy-4-methylthiobuttersäure (MHA)
JP3804210B2 (ja) * 1997-03-04 2006-08-02 住友化学株式会社 ２−ヒドロキシ−４−メチルチオブタン酸の製造方法
RU2184111C2 (ru) * 1997-03-04 2002-06-27 Сумитомо Кемикал Компани, Лимитед Способ получения 2-гидрокси-4-метилтиобутановой кислоты
US6017563A (en) 1997-07-25 2000-01-25 Novus International, Inc. Process for optimizing milk production
FR2780969B1 (fr) * 1998-07-10 2000-08-18 Rhone Poulenc Nutrition Animal Procede de separation de l'acide hydroxymethylthiobutyrique
FR2780968B1 (fr) * 1998-07-10 2000-08-18 Rhone Poulenc Nutrition Animal Procede de preparation de l'acide hydroxymethylthiobutyrique
FR2791673B1 (fr) 1999-04-02 2001-06-08 Rhone Poulenc Animal Nutrition Procede de preparation des esters de l'acide hydroxymethylthiobutyrique
WO2001010776A1 (en) 1999-08-05 2001-02-15 Novus International, Inc. Reductive combustion of ammonium salts of sulfuric acid
US6649794B2 (en) 2000-02-18 2003-11-18 Sumitomo Chemical Company, Limited Method for producing 2-Hydroxy-4-Methylthiobutanoic Acid
TWI296652B (en) * 2000-03-29 2008-05-11 Mitsui Chemicals Inc Production process of amide compound
JP4517474B2 (ja) * 2000-07-25 2010-08-04 住友化学株式会社 ２−ヒドロキシ−４−メチルチオブタン酸の製造方法
JP4517486B2 (ja) * 2000-09-25 2010-08-04 住友化学株式会社 ２−ヒドロキシ−４−メチルチオブタンニトリルの製造方法
JP4517520B2 (ja) * 2001-02-27 2010-08-04 住友化学株式会社 ２−ヒドロキシ−４−メチルチオブタン酸の製造方法
DE10316110A1 (de) * 2003-04-09 2004-10-28 Degussa Ag Verfahren zur Herstellung von 2-Hydroxy-4-methylthio-buttersäure Ammoniumsalz
FR2871028B1 (fr) * 2004-06-08 2006-12-29 Adisseo Ireland Ltd Complement alimentaire pour animaux, comprenant un additif olfactif
JP4696496B2 (ja) 2004-08-18 2011-06-08 住友化学株式会社 ２−ヒドロキシ−４−メチルチオ酪酸の製造方法
ES2324547T3 (es) * 2004-10-14 2009-08-10 Sumitomo Chemical Company, Limited Metodo para la produccion de acido 2-hidroxi-4-(metil-tio)butirico.
DE102005050106B4 (de) * 2005-10-18 2008-04-30 Josef Meissner Gmbh & Co. Kg Rückgewinnung von Nitriersäuregemischen aus Nitrienprozessen
ES2279719B1 (es) * 2006-01-26 2008-07-16 Timac Agro España, S.A. Nuevo activador metabolico y nutricional para las plantas.
WO2008010609A1 (en) 2006-07-21 2008-01-24 Sumitomo Chemical Company, Limited Process for producing 2-hydroxy-4-(methylthio)butyrate compounds and intermediates thereof
DE102007062199A1 (de) * 2007-12-21 2009-06-25 Evonik Degussa Gmbh 2-Methylthioethyl-substituierte Heterocyclen als Futtermitteladditive
JP2009161499A (ja) * 2008-01-10 2009-07-23 Sumitomo Chemical Co Ltd ２−ヒドロキシ−４−メチルチオブタンアミドの製造方法
FR2938535B1 (fr) 2008-11-20 2012-08-17 Arkema France Procede de fabrication de methylmercaptopropionaldehyde et de methionine a partir de matieres renouvelables
FR2939791B1 (fr) * 2008-12-16 2011-01-14 Adisseo France Sas Procede de preparation d'acroleine a partir de glycerol ou de glycerine brute
US9023624B2 (en) 2010-12-30 2015-05-05 Metabolic Explorer Fermentative production of methionine hydroxy analog (MHA)
ES2702723T3 (es) 2012-02-09 2019-03-05 Novus Int Inc Heteroátomos que contienen dímeros cíclicos
KR101419118B1 (ko) * 2012-07-11 2014-07-11 김건희 사료용 향료 조성물
EP3388056A1 (en) 2012-07-12 2018-10-17 Novus International Inc. Matrix and layer compositions for protection of bioactives
MX2016010596A (es) * 2014-02-20 2016-11-15 Smidth As F L Sedimentador de columna para la separacion de fases liquido/liquido de alto redimiento en procesos hidromelurciales y metodos de los mismos.
CN104860855B (zh) * 2014-12-08 2017-06-16 宁夏紫光天化蛋氨酸有限责任公司 一种高纯度的d,l‑2‑羟基‑4‑甲硫基丁酸酯的制备方法
CN109310110A (zh) * 2016-06-24 2019-02-05 诺华丝国际股份有限公司 适用于特种化学应用的羟基甲硫氨酸类似物制剂
FR3064006B1 (fr) 2017-03-16 2019-03-29 Adisseo France S.A.S. Procede de fabrication de l'acide-2-hydroxy-4-methylthio-butyrique
US10584306B2 (en) 2017-08-11 2020-03-10 Board Of Regents Of The University Of Oklahoma Surfactant microemulsions

Family Cites Families (7)

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Publication number Priority date Publication date Assignee Title
GB722024A (en) * 1950-10-31 1955-01-19 Monsanto Chemicals Production of alpha-hydroxy-gamma-mercapto-carboxylic acids and salts thereof and compositions containing the same
US2745745A (en) * 1952-10-30 1956-05-15 Monsanto Chemicals Poultry feed
US2938053A (en) * 1955-12-29 1960-05-24 Monsanto Chemicals Amino acid analogues
CH385823A (de) * 1959-09-01 1964-12-31 Inventa Ag Verfahren zur Herstellung des Calciumsalzes der a-Oxy-y-methylthio-buttersäure
BE611435A (fr) * 1960-12-14 1962-06-12 Stamicarbon Procédé de préparation de sels métalliques d'acide alpha-hydroxy- gamma -méthylmercaptobutyrique
US3773927A (en) * 1971-12-20 1973-11-20 Du Pont Preparation of an aqueous slurry of ammonium chloride and methylmercapto-hydroxybutyric acid
US4310690A (en) * 1980-10-08 1982-01-12 E. I. Du Pont De Nemours And Company Preparation of the calcium salt of α-hydroxy-gamma-methylmercaptobutyric acid

Also Published As

Publication number Publication date
MX163989B (es) 1992-07-07
EP0142488B1 (en) 1987-08-26
GEP19960463B (en) 1996-07-15
JPH05211846A (ja) 1993-08-24
JPH0797970B2 (ja) 1995-10-25
DE3465592D1 (en) 1987-10-01
AU562078B2 (en) 1987-05-28
JPH051787B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1993-01-11
CA1263668A (en) 1989-12-05
EP0142488A3 (en) 1985-06-26
KR850004108A (ko) 1985-07-01
US4524077A (en) 1985-06-18
EP0142488A2 (en) 1985-05-22
GB2149791B (en) 1988-04-20
JPS60156396A (ja) 1985-08-16
ZA848847B (en) 1985-09-25
ATE29131T1 (de) 1987-09-15
AU3535984A (en) 1985-05-23
SU1428193A3 (ru) 1988-09-30
GB2149791A (en) 1985-06-19
KR870000657B1 (ko) 1987-04-04
GB8428657D0 (en) 1984-12-19

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Legal Events

Date Code Title Description
MKEX Expiry
MKEX Expiry

Effective date: 20061205