ES2045478T3 - Procedimiento para preparar soluciones acuosas de acido 2-hidroxi-4-metiltio-butirico. - Google Patents
Procedimiento para preparar soluciones acuosas de acido 2-hidroxi-4-metiltio-butirico.Info
- Publication number
- ES2045478T3 ES2045478T3 ES89400157T ES89400157T ES2045478T3 ES 2045478 T3 ES2045478 T3 ES 2045478T3 ES 89400157 T ES89400157 T ES 89400157T ES 89400157 T ES89400157 T ES 89400157T ES 2045478 T3 ES2045478 T3 ES 2045478T3
- Authority
- ES
- Spain
- Prior art keywords
- hydroxy
- methyltio
- procedure
- organic phase
- aqueous solutions
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title 1
- 239000007864 aqueous solution Substances 0.000 title 1
- 239000012074 organic phase Substances 0.000 abstract 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 239000008346 aqueous phase Substances 0.000 abstract 2
- 238000006386 neutralization reaction Methods 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- VWWOJJANXYSACS-UHFFFAOYSA-N 2-hydroxy-4-methylsulfanylbutanenitrile Chemical compound CSCCC(O)C#N VWWOJJANXYSACS-UHFFFAOYSA-N 0.000 abstract 1
- PICCHNWCTUUCAQ-UHFFFAOYSA-N 2-hydroxypentanethioic s-acid Chemical compound CCCC(O)C(O)=S PICCHNWCTUUCAQ-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000908 ammonium hydroxide Substances 0.000 abstract 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 abstract 1
- 239000001166 ammonium sulphate Substances 0.000 abstract 1
- 235000011130 ammonium sulphate Nutrition 0.000 abstract 1
- 239000006053 animal diet Substances 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 235000015872 dietary supplement Nutrition 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
SE DESCRIBE UN PROCEDIMIENTO QUE CONSISTE EN ENUTRALIZAR CON HIDROXIDO DE AMONIO LA MEZCLA REACCIONAL QUE PROVIENE DE LA HIDROLISIS POR ACIDO SULFURICO DEL 2 - HIDROXI - 4 - METILTIO - BUTIRONITRILO, DE MANERA QUE SE OBTENGA UNA FASE ACUOSA Y UNA FASE ORGANICA, QUE UNA VEZ SEPARADAS, SON SOMETIDAS A EVAPORACION PARA SEPARAR EL SULFATO DE AMONIO FORMADO. EN EL CASO DE LA FASE ACIOSA, ESTE SULFATO ES RETIRADO COMO SUBPRODUCTO Y, EN EL CASO DE LA FASE ORGANICA, ES PUESTO EN CIRCULACION HASTA EL RECIPIENTE DE NEUTRALIZACION. EL ACIDO 2 HIDROXI - 4 - METILTIO - BUTIRICO OBTENIDO A PARTIR DE LA FASE ORGANICA ES ENSEGUIDA DILUIDO CON AGUA Y EVENTUALMENTE ESTABILIZADO CON ACIDO SULFURICO. EL PRODUCTO OBTENIDO ES UTIL COMO SUPLEMENTO ALIMENTARIO EN EL REGIMEN DE LOS ANIMALES.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES8800496A ES2005784A6 (es) | 1988-02-22 | 1988-02-22 | Un procedimiento para preparar soluciones acuosas de acido 2-hidroxi-4-metil-tiobutirico. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2045478T3 true ES2045478T3 (es) | 1994-01-16 |
Family
ID=8254970
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES8800496A Expired ES2005784A6 (es) | 1988-02-22 | 1988-02-22 | Un procedimiento para preparar soluciones acuosas de acido 2-hidroxi-4-metil-tiobutirico. |
| ES89400157T Expired - Lifetime ES2045478T3 (es) | 1988-02-22 | 1989-01-19 | Procedimiento para preparar soluciones acuosas de acido 2-hidroxi-4-metiltio-butirico. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES8800496A Expired ES2005784A6 (es) | 1988-02-22 | 1988-02-22 | Un procedimiento para preparar soluciones acuosas de acido 2-hidroxi-4-metil-tiobutirico. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4912257A (es) |
| EP (1) | EP0330527B1 (es) |
| AT (1) | ATE80871T1 (es) |
| CA (1) | CA1308419C (es) |
| DE (1) | DE68902934T2 (es) |
| DK (1) | DK175368B1 (es) |
| ES (2) | ES2005784A6 (es) |
| GR (1) | GR3005881T3 (es) |
| HK (1) | HK17793A (es) |
| IE (1) | IE63393B1 (es) |
| PT (1) | PT89776B (es) |
| SG (1) | SG125692G (es) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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) |
| FR2733231B1 (fr) * | 1995-04-24 | 1997-07-04 | Rhone Poulenc Nutrition Animal | Procede de condensation de l'acide cyanhydrique avec un aldehyde |
| US5583243A (en) * | 1995-05-19 | 1996-12-10 | Zinpro Corporation | Salts of alpha-hydroxy aliphatic carboxylic acids and uses thereof |
| JPH11508876A (ja) | 1995-06-07 | 1999-08-03 | ノーバス インターナショナル インコーポレイテッド | 2−ヒドロキシ−4−メチルチオブタン酸又はその塩を製造するための連続加水分解法 |
| US5856567A (en) | 1995-06-07 | 1999-01-05 | Novus International, Inc. | Continuous hydrolysis process for preparing 2-hydroxy-4-methylthiobutanioc acid or salts thereof |
| DE19548538C2 (de) * | 1995-12-23 | 1997-12-18 | Degussa | Verfahren zur Gewinnung von 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 |
| DE19754562A1 (de) * | 1997-12-09 | 1999-06-10 | Degussa | Verfahren zur Rückgewinnung von Schwefelsäure aus schwefelhaltigen Nebenprodukten eines Prozesses zur Herstellung von 2-Hydroxy-4-methylthiobuttersäure (MHA) |
| 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 |
| AU2324000A (en) * | 1999-02-03 | 2000-08-25 | Sumitomo Chemical Company, Limited | Process for producing 2-hydroxy-4-methyl-thiobutanoic acid |
| 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 |
| WO2005091739A2 (en) * | 2004-02-26 | 2005-10-06 | Tasker Products Ip Holdings Corp. | Antimicrobial composition for pre-harvest and post-harvest treatment of plants and animals |
| 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 |
| DE102004041250A1 (de) * | 2004-08-26 | 2006-03-02 | Degussa Ag | Herstellung von 2-Hydroxy-4-Methylthiobuttersäure |
| JP4948002B2 (ja) * | 2006-03-10 | 2012-06-06 | 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および製造装置 |
| JP4896548B2 (ja) * | 2006-03-10 | 2012-03-14 | 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および製造装置 |
| WO2012113665A1 (de) | 2011-02-23 | 2012-08-30 | Evonik Degussa Gmbh | Lagerstabiles 2-hydroxy-4-(methylthio)buttersäurenitril |
| WO2012113664A1 (de) * | 2011-02-23 | 2012-08-30 | Evonik Degussa Gmbh | Verfahren zur herstellung von 2-hydroxy-4-(methylthio)buttersäurenitril aus 3-(methylthio)propanal und cyanwasserstoff |
| CN103420883A (zh) * | 2013-08-28 | 2013-12-04 | 重庆紫光化工股份有限公司 | 利用粗氢氰酸气体制备2-羟基-4-甲硫基丁腈的方法 |
| CN103641754B (zh) * | 2013-11-19 | 2016-08-24 | 宁夏紫光天化蛋氨酸有限责任公司 | 药用d,l-2-羟基-4-甲硫基丁酸金属螯合物的制备方法 |
| CN104262216A (zh) * | 2014-10-15 | 2015-01-07 | 重庆紫光化工股份有限公司 | 一种2-羟基-4-甲硫基丁酸的制备方法 |
| CN105130861A (zh) * | 2015-07-28 | 2015-12-09 | 重庆紫光国际化工有限责任公司 | 氰醇水解法合成蛋氨酸羟基类似物的分离纯化方法 |
| FR3064006B1 (fr) * | 2017-03-16 | 2019-03-29 | Adisseo France S.A.S. | Procede de fabrication de l'acide-2-hydroxy-4-methylthio-butyrique |
| CN111116437B (zh) | 2018-11-01 | 2021-02-05 | 山东新和成氨基酸有限公司 | 制备2-羟基-4-甲硫基丁酸及其中间体的方法和装置 |
| CN109232336A (zh) * | 2018-11-09 | 2019-01-18 | 禄丰天宝磷化工有限公司 | 一种清洁环保的蛋氨酸羟基类似物生产方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA694610A (en) * | 1964-09-22 | J. Wineman Robert | Preparation of salts of 2-hydroxy-4-alkylthiobutyric acid | |
| CA694650A (en) * | 1964-09-22 | Mark Victor | Preparation of 4-(alkylthio)-2-hydroxybutyric acids | |
| 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 |
| GB1353832A (en) * | 1971-08-03 | 1974-05-22 | Degussa | Sulphonium compounds of alpha-hydroxy-gamma-alkyl-mercapto butyric acid |
| US3773927A (en) * | 1971-12-20 | 1973-11-20 | Du Pont | Preparation of an aqueous slurry of ammonium chloride and methylmercapto-hydroxybutyric acid |
| US4353924A (en) * | 1979-09-04 | 1982-10-12 | Monsanto Company | Animal feed supplement having reduced corrosion characteristics |
| US4524077A (en) * | 1983-11-14 | 1985-06-18 | Monsanto Company | Liquid 2-hydroxy-4-methylthiobutyric acid and process for the preparation thereof |
| JPS60166661A (ja) * | 1983-11-14 | 1985-08-29 | ヌブス インターナショナル,インコーポレイテッド | 2−ヒドロキシ−4−メチルチオ酪酸の製造方法 |
-
1988
- 1988-02-22 ES ES8800496A patent/ES2005784A6/es not_active Expired
-
1989
- 1989-01-19 AT AT89400157T patent/ATE80871T1/de not_active IP Right Cessation
- 1989-01-19 ES ES89400157T patent/ES2045478T3/es not_active Expired - Lifetime
- 1989-01-19 EP EP19890400157 patent/EP0330527B1/fr not_active Expired - Lifetime
- 1989-01-19 DE DE8989400157T patent/DE68902934T2/de not_active Expired - Fee Related
- 1989-02-03 CA CA000590042A patent/CA1308419C/fr not_active Expired - Lifetime
- 1989-02-13 US US07/309,241 patent/US4912257A/en not_active Expired - Lifetime
- 1989-02-21 PT PT89776A patent/PT89776B/pt not_active IP Right Cessation
- 1989-02-21 IE IE54789A patent/IE63393B1/en not_active IP Right Cessation
- 1989-02-21 DK DK198900788A patent/DK175368B1/da not_active IP Right Cessation
-
1992
- 1992-10-05 GR GR920400876T patent/GR3005881T3/el unknown
- 1992-12-09 SG SG1256/92A patent/SG125692G/en unknown
-
1993
- 1993-03-04 HK HK177/93A patent/HK17793A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HK17793A (en) | 1993-03-12 |
| DK175368B1 (da) | 2004-09-13 |
| PT89776B (pt) | 1994-03-31 |
| CA1308419C (fr) | 1992-10-06 |
| IE63393B1 (en) | 1995-04-19 |
| IE890547L (en) | 1989-08-22 |
| US4912257A (en) | 1990-03-27 |
| EP0330527A1 (fr) | 1989-08-30 |
| DE68902934T2 (de) | 1993-04-08 |
| ES2005784A6 (es) | 1989-03-16 |
| SG125692G (en) | 1993-02-19 |
| DK78889D0 (da) | 1989-02-21 |
| ATE80871T1 (de) | 1992-10-15 |
| PT89776A (pt) | 1989-10-04 |
| DK78889A (da) | 1989-08-22 |
| DE68902934D1 (de) | 1992-10-29 |
| EP0330527B1 (fr) | 1992-09-23 |
| GR3005881T3 (es) | 1993-06-07 |
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