UA72737C2 - A method for the preparation of 2-hydroxy-4-hydroxymethylthiobutyric acid - Google Patents
A method for the preparation of 2-hydroxy-4-hydroxymethylthiobutyric acid Download PDFInfo
- Publication number
- UA72737C2 UA72737C2 UA2001020867A UA2001020867A UA72737C2 UA 72737 C2 UA72737 C2 UA 72737C2 UA 2001020867 A UA2001020867 A UA 2001020867A UA 2001020867 A UA2001020867 A UA 2001020867A UA 72737 C2 UA72737 C2 UA 72737C2
- Authority
- UA
- Ukraine
- Prior art keywords
- salts
- organic solvent
- aqueous phase
- hmtbc
- phase
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims description 3
- JRNNIJQRCQUODQ-UHFFFAOYSA-N 2,5-dihydroxypentanethioic S-acid Chemical compound OC(C(=S)O)CCCO JRNNIJQRCQUODQ-UHFFFAOYSA-N 0.000 title 1
- 239000003960 organic solvent Substances 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims description 51
- ONFOSYPQQXJWGS-UHFFFAOYSA-N 2-hydroxy-4-(methylthio)butanoic acid Chemical compound CSCCC(O)C(O)=O ONFOSYPQQXJWGS-UHFFFAOYSA-N 0.000 claims description 42
- 239000008346 aqueous phase Substances 0.000 claims description 33
- 238000000605 extraction Methods 0.000 claims description 29
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 27
- 239000012074 organic phase Substances 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 238000005185 salting out Methods 0.000 claims description 17
- 238000010908 decantation Methods 0.000 claims description 15
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 10
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 10
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 8
- 150000002170 ethers Chemical class 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 238000001704 evaporation Methods 0.000 claims description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- 230000008020 evaporation Effects 0.000 claims description 6
- VWWOJJANXYSACS-UHFFFAOYSA-N 2-hydroxy-4-methylsulfanylbutanenitrile Chemical compound CSCCC(O)C#N VWWOJJANXYSACS-UHFFFAOYSA-N 0.000 claims description 5
- 238000006386 neutralization reaction Methods 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 238000000909 electrodialysis Methods 0.000 claims description 2
- 230000008929 regeneration Effects 0.000 claims description 2
- 238000011069 regeneration method Methods 0.000 claims description 2
- WUPZNKGVDMHMBS-UHFFFAOYSA-N azane;dihydrate Chemical compound [NH4+].[NH4+].[OH-].[OH-] WUPZNKGVDMHMBS-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000197 pyrolysis Methods 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 abstract description 2
- BINDPFUXHYGSSV-UHFFFAOYSA-N 2-(hydroxymethyl)butanethioic s-acid Chemical compound CCC(CO)C(S)=O BINDPFUXHYGSSV-UHFFFAOYSA-N 0.000 abstract 1
- DTSSQKXKIMHICE-UHFFFAOYSA-N 2-(hydroxymethylsulfanyl)butanenitrile Chemical compound CCC(C#N)SCO DTSSQKXKIMHICE-UHFFFAOYSA-N 0.000 abstract 1
- 108010009736 Protein Hydrolysates Proteins 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 46
- 239000000243 solution Substances 0.000 description 21
- 239000007788 liquid Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 6
- 235000011130 ammonium sulphate Nutrition 0.000 description 6
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 208000005156 Dehydration Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000000622 liquid--liquid extraction Methods 0.000 description 2
- 230000010349 pulsation Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- WXOMTJVVIMOXJL-BOBFKVMVSA-A O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)OS(=O)(=O)OC[C@H]1O[C@@H](O[C@]2(COS(=O)(=O)O[Al](O)O)O[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]2OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]1OS(=O)(=O)O[Al](O)O Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)OS(=O)(=O)OC[C@H]1O[C@@H](O[C@]2(COS(=O)(=O)O[Al](O)O)O[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]2OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]1OS(=O)(=O)O[Al](O)O WXOMTJVVIMOXJL-BOBFKVMVSA-A 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 208000016253 exhaustion Diseases 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- -1 for example Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002957 persistent organic pollutant Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9808874A FR2780969B1 (fr) | 1998-07-10 | 1998-07-10 | Procede de separation de l'acide hydroxymethylthiobutyrique |
| PCT/FR1999/001636 WO2000002853A1 (fr) | 1998-07-10 | 1999-07-07 | Procede de separation de l'acide hydroxymethylthiobutyrique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA72737C2 true UA72737C2 (en) | 2005-04-15 |
Family
ID=9528517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2001020867A UA72737C2 (en) | 1998-07-10 | 1999-07-07 | A method for the preparation of 2-hydroxy-4-hydroxymethylthiobutyric acid |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6743946B1 (de) |
| EP (1) | EP1097131B1 (de) |
| JP (1) | JP4458671B2 (de) |
| CN (1) | CN1216043C (de) |
| AT (1) | ATE305922T1 (de) |
| AU (1) | AU4624499A (de) |
| BR (1) | BR9912017A (de) |
| DE (1) | DE69927593T2 (de) |
| DK (1) | DK1097131T3 (de) |
| EA (1) | EA003752B1 (de) |
| ES (1) | ES2249895T3 (de) |
| FR (1) | FR2780969B1 (de) |
| UA (1) | UA72737C2 (de) |
| WO (1) | WO2000002853A1 (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP4517491B2 (ja) * | 2000-10-11 | 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 |
| 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 |
| 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 |
| US10106496B2 (en) | 2016-06-24 | 2018-10-23 | Novus International, Inc. | Hydroxy methionine analog formulations suitable for specialty chemical applications |
| FR3064006B1 (fr) * | 2017-03-16 | 2019-03-29 | Adisseo France S.A.S. | Procede de fabrication de l'acide-2-hydroxy-4-methylthio-butyrique |
| CN110483348B (zh) * | 2019-09-03 | 2021-12-07 | 蓝星安迪苏南京有限公司 | 包含蛋氨酸羟基类似物及其低聚物的混合物及其制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2745745A (en) * | 1952-10-30 | 1956-05-15 | Monsanto Chemicals | Poultry feed |
| BE611435A (fr) * | 1960-12-14 | 1962-06-12 | Stamicarbon | Procédé de préparation de sels métalliques d'acide alpha-hydroxy- gamma -méthylmercaptobutyrique |
| DE2727409C2 (de) * | 1977-06-18 | 1983-01-20 | Battelle-Institut E.V., 6000 Frankfurt | Verfahren zur Gewinnung von Ammoniak und Schwefelsäure aus einer Ammoniumsulfatlösung |
| US4353924A (en) * | 1979-09-04 | 1982-10-12 | Monsanto Company | Animal feed supplement having reduced corrosion characteristics |
| 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 |
| 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 |
| US4579962A (en) * | 1984-02-24 | 1986-04-01 | Monsanto Company | Enhanced 2-hydroxy-4-methylthiobutanoic acid compositions and method of preparation |
| 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 |
| SG59966A1 (en) * | 1995-03-08 | 1999-02-22 | Daicel Chem | Process for producing a carboxylic acid |
| DE19548538C2 (de) * | 1995-12-23 | 1997-12-18 | Degussa | Verfahren zur Gewinnung von 2-Hydroxy-4-methylthiobuttersäure (MHA) |
-
1998
- 1998-07-10 FR FR9808874A patent/FR2780969B1/fr not_active Expired - Fee Related
-
1999
- 1999-07-07 US US09/743,288 patent/US6743946B1/en not_active Expired - Lifetime
- 1999-07-07 AU AU46244/99A patent/AU4624499A/en not_active Abandoned
- 1999-07-07 CN CN99810294.6A patent/CN1216043C/zh not_active Expired - Lifetime
- 1999-07-07 WO PCT/FR1999/001636 patent/WO2000002853A1/fr not_active Ceased
- 1999-07-07 BR BR9912017-8A patent/BR9912017A/pt not_active Application Discontinuation
- 1999-07-07 UA UA2001020867A patent/UA72737C2/uk unknown
- 1999-07-07 JP JP2000559084A patent/JP4458671B2/ja not_active Expired - Lifetime
- 1999-07-07 ES ES99929421T patent/ES2249895T3/es not_active Expired - Lifetime
- 1999-07-07 EA EA200100130A patent/EA003752B1/ru not_active IP Right Cessation
- 1999-07-07 DK DK99929421T patent/DK1097131T3/da active
- 1999-07-07 AT AT99929421T patent/ATE305922T1/de not_active IP Right Cessation
- 1999-07-07 EP EP99929421A patent/EP1097131B1/de not_active Expired - Lifetime
- 1999-07-07 DE DE69927593T patent/DE69927593T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EA200100130A1 (ru) | 2001-06-25 |
| EP1097131A1 (de) | 2001-05-09 |
| CN1315939A (zh) | 2001-10-03 |
| FR2780969A1 (fr) | 2000-01-14 |
| US6743946B1 (en) | 2004-06-01 |
| EA003752B1 (ru) | 2003-08-28 |
| JP4458671B2 (ja) | 2010-04-28 |
| WO2000002853A1 (fr) | 2000-01-20 |
| BR9912017A (pt) | 2001-04-03 |
| ATE305922T1 (de) | 2005-10-15 |
| JP2002520311A (ja) | 2002-07-09 |
| CN1216043C (zh) | 2005-08-24 |
| DE69927593T2 (de) | 2006-07-06 |
| FR2780969B1 (fr) | 2000-08-18 |
| DE69927593D1 (de) | 2006-02-16 |
| DK1097131T3 (da) | 2006-02-06 |
| ES2249895T3 (es) | 2006-04-01 |
| EP1097131B1 (de) | 2005-10-05 |
| AU4624499A (en) | 2000-02-01 |
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