JP3962089B2 - 2―ヒドロキシ―4―メチルチオ酪酸(mha)の取得法 - Google Patents
2―ヒドロキシ―4―メチルチオ酪酸(mha)の取得法 Download PDFInfo
- Publication number
- JP3962089B2 JP3962089B2 JP52325597A JP52325597A JP3962089B2 JP 3962089 B2 JP3962089 B2 JP 3962089B2 JP 52325597 A JP52325597 A JP 52325597A JP 52325597 A JP52325597 A JP 52325597A JP 3962089 B2 JP3962089 B2 JP 3962089B2
- Authority
- JP
- Japan
- Prior art keywords
- mha
- extraction
- liquid
- salt
- weight
- 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 claims 20
- PICCHNWCTUUCAQ-UHFFFAOYSA-N 2-hydroxypentanethioic s-acid Chemical compound CCCC(O)C(O)=S PICCHNWCTUUCAQ-UHFFFAOYSA-N 0.000 title claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 9
- 238000000605 extraction Methods 0.000 claims 6
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 6
- 239000007791 liquid phase Substances 0.000 claims 6
- 239000011541 reaction mixture Substances 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- CLUWOWRTHNNBBU-UHFFFAOYSA-N 3-methylthiopropanal Chemical compound CSCCC=O CLUWOWRTHNNBBU-UHFFFAOYSA-N 0.000 claims 3
- 230000007062 hydrolysis Effects 0.000 claims 3
- 238000006460 hydrolysis reaction Methods 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- 238000007259 addition reaction Methods 0.000 claims 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims 2
- 235000011130 ammonium sulphate Nutrition 0.000 claims 2
- 238000001704 evaporation Methods 0.000 claims 2
- 230000008020 evaporation Effects 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 238000000622 liquid--liquid extraction Methods 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 238000000638 solvent extraction Methods 0.000 claims 2
- -1 sulfuric acid 2-Hydroxy-4-methylthiobutyric acid Chemical compound 0.000 claims 2
- VWWOJJANXYSACS-UHFFFAOYSA-N 2-hydroxy-4-methylsulfanylbutanenitrile Chemical compound CSCCC(O)C#N VWWOJJANXYSACS-UHFFFAOYSA-N 0.000 claims 1
- BHPAXKBSATVOQB-UHFFFAOYSA-N 2-methylbutanethioamide Chemical compound CCC(C)C(N)=S BHPAXKBSATVOQB-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 239000012465 retentate Substances 0.000 claims 1
- 238000005185 salting out Methods 0.000 claims 1
Images
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
-
- 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
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Power Steering Mechanism (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19548538A DE19548538C2 (de) | 1995-12-23 | 1995-12-23 | Verfahren zur Gewinnung von 2-Hydroxy-4-methylthiobuttersäure (MHA) |
| DE19548538.6 | 1995-12-23 | ||
| PCT/EP1996/005437 WO1997023452A1 (de) | 1995-12-23 | 1996-12-05 | Verfahren zur gewinnung von 2-hydroxy-4-methylthiobuttersäure (mha) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000502110A JP2000502110A (ja) | 2000-02-22 |
| JP3962089B2 true JP3962089B2 (ja) | 2007-08-22 |
Family
ID=7781282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52325597A Expired - Lifetime JP3962089B2 (ja) | 1995-12-23 | 1996-12-05 | 2―ヒドロキシ―4―メチルチオ酪酸(mha)の取得法 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6140536A (2) |
| EP (1) | EP0874811B1 (2) |
| JP (1) | JP3962089B2 (2) |
| KR (1) | KR100460364B1 (2) |
| CN (1) | CN1067377C (2) |
| AU (1) | AU717705B2 (2) |
| BR (1) | BR9612235A (2) |
| DE (2) | DE19548538C2 (2) |
| ES (1) | ES2160264T3 (2) |
| ID (1) | ID16007A (2) |
| IN (1) | IN190919B (2) |
| MX (1) | MX9804881A (2) |
| MY (1) | MY117493A (2) |
| RU (1) | RU2160730C2 (2) |
| TR (1) | TR199801190T2 (2) |
| TW (1) | TW371655B (2) |
| WO (1) | WO1997023452A1 (2) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6017563A (en) | 1997-07-25 | 2000-01-25 | Novus International, Inc. | Process for optimizing milk production |
| JP3942715B2 (ja) | 1998-01-06 | 2007-07-11 | パイオニア株式会社 | 有機elディスプレイパネル及びその製造方法 |
| FR2780969B1 (fr) * | 1998-07-10 | 2000-08-18 | Rhone Poulenc Nutrition Animal | Procede de separation de l'acide hydroxymethylthiobutyrique |
| 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 |
| 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 |
| DE102004041250A1 (de) * | 2004-08-26 | 2006-03-02 | Degussa Ag | Herstellung von 2-Hydroxy-4-Methylthiobuttersäure |
| JP2007238552A (ja) * | 2006-03-10 | 2007-09-20 | Sumitomo Chemical Co Ltd | 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 |
| KR101911563B1 (ko) | 2011-02-23 | 2018-10-24 | 에보니크 데구사 게엠베하 | 3-(메틸티오)프로판알 및 시안화수소로부터 2-히드록시-4-(메틸티오)부탄니트릴을 제조하는 방법 |
| DE102011081828A1 (de) | 2011-08-30 | 2013-02-28 | Evonik Degussa Gmbh | Verfahren zur Umsetzung von Methylmercaptopropionaldehyd aus Roh-Acrolein und Roh-Methylmercaptan |
| MY171361A (en) | 2011-08-30 | 2019-10-10 | Evonik Operations Gmbh | Method for producing a methionine salt |
| RU2571755C2 (ru) * | 2013-10-23 | 2015-12-20 | Андрей Вилорьевич Доронин | Способ сернокислотной переработки сырья |
| EP3388523A1 (en) | 2017-04-13 | 2018-10-17 | Evonik Degussa GmbH | Enzymatic method for producing 2-hydroxy-4-methylmercaptobutanoic acid (mha) |
| CN114349671B (zh) * | 2022-03-18 | 2022-05-27 | 蓝星安迪苏南京有限公司 | 化合物及蛋氨酸羟基衍生物的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1269995C (en) * | 1983-11-14 | 1990-06-05 | PREPARATION OF 2-HYDROXY-METHYLTHIOBUTYRIC ACID LIQUID | |
| US4524077A (en) * | 1983-11-14 | 1985-06-18 | Monsanto Company | Liquid 2-hydroxy-4-methylthiobutyric acid and process for the preparation thereof |
| 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. |
| 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 |
| DE4428608C1 (de) * | 1994-08-12 | 1996-02-29 | Degussa | Verfahren zur Gewinnung von 2-Hydroxy-4-methylthiobuttersäure (MHA) |
-
1995
- 1995-12-23 DE DE19548538A patent/DE19548538C2/de not_active Expired - Fee Related
-
1996
- 1996-12-05 CN CN96199293A patent/CN1067377C/zh not_active Expired - Lifetime
- 1996-12-05 TR TR1998/01190T patent/TR199801190T2/xx unknown
- 1996-12-05 BR BR9612235A patent/BR9612235A/pt not_active Application Discontinuation
- 1996-12-05 ES ES96943038T patent/ES2160264T3/es not_active Expired - Lifetime
- 1996-12-05 US US09/091,796 patent/US6140536A/en not_active Expired - Lifetime
- 1996-12-05 EP EP96943038A patent/EP0874811B1/de not_active Expired - Lifetime
- 1996-12-05 RU RU98114099/04A patent/RU2160730C2/ru active
- 1996-12-05 JP JP52325597A patent/JP3962089B2/ja not_active Expired - Lifetime
- 1996-12-05 DE DE59607103T patent/DE59607103D1/de not_active Expired - Lifetime
- 1996-12-05 KR KR10-1998-0704772A patent/KR100460364B1/ko not_active Expired - Fee Related
- 1996-12-05 WO PCT/EP1996/005437 patent/WO1997023452A1/de not_active Ceased
- 1996-12-05 AU AU11906/97A patent/AU717705B2/en not_active Ceased
- 1996-12-19 ID IDP963809A patent/ID16007A/id unknown
- 1996-12-19 MY MYPI96005345A patent/MY117493A/en unknown
- 1996-12-20 IN IN2209CA1996 patent/IN190919B/en unknown
- 1996-12-20 TW TW085115766A patent/TW371655B/zh active
-
1998
- 1998-06-17 MX MX9804881A patent/MX9804881A/es not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IN190919B (2) | 2003-08-30 |
| AU1190697A (en) | 1997-07-17 |
| DE19548538A1 (de) | 1997-06-26 |
| EP0874811A1 (de) | 1998-11-04 |
| WO1997023452A1 (de) | 1997-07-03 |
| DE59607103D1 (de) | 2001-07-19 |
| TW371655B (en) | 1999-10-11 |
| MX9804881A (es) | 1998-10-31 |
| MY117493A (en) | 2004-07-31 |
| ES2160264T3 (es) | 2001-11-01 |
| BR9612235A (pt) | 1999-07-13 |
| KR19990076661A (ko) | 1999-10-15 |
| KR100460364B1 (ko) | 2005-05-20 |
| RU2160730C2 (ru) | 2000-12-20 |
| JP2000502110A (ja) | 2000-02-22 |
| CN1067377C (zh) | 2001-06-20 |
| DE19548538C2 (de) | 1997-12-18 |
| AU717705B2 (en) | 2000-03-30 |
| TR199801190T2 (xx) | 1998-11-23 |
| US6140536A (en) | 2000-10-31 |
| CN1205688A (zh) | 1999-01-20 |
| ID16007A (id) | 1997-08-28 |
| EP0874811B1 (de) | 2001-06-13 |
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