JP2000502110A - 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Info
- Publication number
- JP2000502110A JP2000502110A JP9523255A JP52325597A JP2000502110A JP 2000502110 A JP2000502110 A JP 2000502110A JP 9523255 A JP9523255 A JP 9523255A JP 52325597 A JP52325597 A JP 52325597A JP 2000502110 A JP2000502110 A JP 2000502110A
- Authority
- JP
- Japan
- Prior art keywords
- mha
- weight
- extraction
- liquid
- solvent
- 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.)
- Granted
Links
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
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.メチルメルカプトプロピオンアルデヒド(MMP)への青酸(HCN)の付 加反応及びその際得られたメチルメルカプトプロピオン酸アルデヒドーシアノヒ ドリン(MMP−CH)の、硫酸を用いる加水分解によって得られる反応混合物 からMHAを単離し、この場合、反応混合物を、液−液抽出システム中で、本質 的に水と混合不可能な有機溶剤と接触させて、溶剤と、反応混合物から変換され たMHAとを有する抽出溶液を形成させ、MHAを、前記抽出溶液からの抽出物 として蒸発によって取得する2−ヒドロキシ−4−メチルチオ酪酸(MHA)の 取得法において、MMP−CHの加水分解を、第1工程で、1:0.5〜1:1 .0のモル比のMMP−CH:H2SO4で60〜85%の硫酸を用いて、30〜 90℃の温度で本質的にMHAアミドを得つつMMP−CHを加水分解し、第2 工程で、水を添加しつつH2SO4を更に添加せずに、140℃までの温度で前記 MHAアミドを加水分解し、反応混合物の塩含量を、液−液抽出の前に、反応混 合物の非有機成分の総和に対して約>50重量%(wt/wt)、有利に>55 重量%(wt/wt)の濃度にするようにして実施することを特徴とする、2− ヒドロキ シ−4−メチルチオ酪酸(MHA)の取得法。 2.MMPへのHCNの付加反応及び生じたMMP−CHの硫酸を用いる加水分 解によって生じた反応混合物に硫酸アンモニウムを添加する、請求項1に記載の 方法。 3.MHAの単離の前に、塩析に有効な量の硫酸アンモニウムを添加する、請求 項2に記載の方法。 4.塩濃度を、蒸発によって増大させる、請求項1に記載の方法。 5.抽出システムから少なくとも3つの液相を直接生じさせる、請求項1から4 までのいずれか1項に記載の方法。 6.均質な抽出物及び2つの液相からなる抽残液を形成させる、請求項5に記載 の方法。 7.第一の液相としての抽残液が、主としてアンモニウム塩と水とからなり、ご く一部がMHAと有機溶剤とからなり、第二の液相としての抽残液が、主として 有機溶剤からなり、ごく一部が水とMHAとからなる、請求項6に記載の方法。 8.第一の液相が、水20〜50重量%、MHA0.01〜0.5重量%及び塩 50〜80重量%の量で含有し、第二の液相が、MHA0.01〜0.5重量% 、溶剤90〜99.9重量%及び水0.1〜10重量%の量で含有し、この場合 、各相の成分は100重量%になる、請求項7に記載の方 法。 9.1:0.6〜1:0.95のMMP−CH:H2SO4のモル比で加水分解す る、請求項1に記載の方法。 10.溶剤として1種以上のエーテルを添加する、請求項1から9までのいずれ か1項に記載の方法。 11.不斉エーテルを添加する、請求項10に記載の方法。 12.<60℃の沸点を有するエーテルを添加する、請求項11に記載の方法。 13.メチル第三ブチルエーテル(MTBE)を添加する、請求項10から12 までのいずれか1項に記載の方法。 14.抽出溶液を、<4%の含水量にまで蒸発させ、残りの溶剤を生じた濃厚液 から留去する、請求項1から13までのいずれか1項に記載の方法。 15.水蒸気を用いてストリッピングする、請求項14に記載の方法。 16.溶剤除去後に、<4%の含水量を有する生成物が生じる、請求項14又は 15に記載の方法。 17.<3%の含水量を有する生成物が生じる、請求項16に記載の方法。
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 true JP2000502110A (ja) | 2000-02-22 |
JP3962089B2 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 (ja) |
EP (1) | EP0874811B1 (ja) |
JP (1) | JP3962089B2 (ja) |
KR (1) | KR100460364B1 (ja) |
CN (1) | CN1067377C (ja) |
AU (1) | AU717705B2 (ja) |
BR (1) | BR9612235A (ja) |
DE (2) | DE19548538C2 (ja) |
ES (1) | ES2160264T3 (ja) |
ID (1) | ID16007A (ja) |
IN (1) | IN190919B (ja) |
MX (1) | MX9804881A (ja) |
MY (1) | MY117493A (ja) |
RU (1) | RU2160730C2 (ja) |
TR (1) | TR199801190T2 (ja) |
TW (1) | TW371655B (ja) |
WO (1) | WO1997023452A1 (ja) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002037769A (ja) * | 2000-07-25 | 2002-02-06 | Sumitomo Chem Co Ltd | 2−ヒドロキシ−4−メチルチオブタン酸の製造方法 |
JP2002105048A (ja) * | 2000-09-25 | 2002-04-10 | Sumitomo Chem Co Ltd | 2−ヒドロキシ−4−メチルチオブタンニトリルの製造方法 |
JP2002114758A (ja) * | 2000-10-11 | 2002-04-16 | Sumitomo Chem Co Ltd | 2−ヒドロキシ−4−メチルチオブタン酸の製造方法 |
JP2002255927A (ja) * | 2001-02-27 | 2002-09-11 | Sumitomo Chem Co Ltd | 2−ヒドロキシ−4−メチルチオブタン酸の製造方法 |
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 |
Families Citing this family (10)
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 |
DE102004041250A1 (de) * | 2004-08-26 | 2006-03-02 | Degussa Ag | Herstellung von 2-Hydroxy-4-Methylthiobuttersäure |
BR112013018092B1 (pt) | 2011-02-23 | 2021-04-27 | Evonik Operations Gmbh | Método para produção de 2-hidróxi-4-(metiltio) butano nitrila a partir de 3- (metiltio) propanal e cianeto de hidrogênio, e uso de um produto de reação, que contém mmp-cianidrina |
MY171361A (en) | 2011-08-30 | 2019-10-10 | Evonik Operations Gmbh | Method for producing a methionine salt |
DE102011081828A1 (de) | 2011-08-30 | 2013-02-28 | Evonik Degussa Gmbh | Verfahren zur Umsetzung von Methylmercaptopropionaldehyd aus Roh-Acrolein und Roh-Methylmercaptan |
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 |
---|---|---|---|---|
DE3465194D1 (en) * | 1983-11-14 | 1987-09-10 | Monsanto Co | Process for the preparation of liquid 2-hydroxy-methylthiobutyric acid |
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 DE DE59607103T patent/DE59607103D1/de not_active Expired - Lifetime
- 1996-12-05 WO PCT/EP1996/005437 patent/WO1997023452A1/de active IP Right Grant
- 1996-12-05 RU RU98114099/04A patent/RU2160730C2/ru active
- 1996-12-05 EP EP96943038A patent/EP0874811B1/de not_active Expired - Lifetime
- 1996-12-05 KR KR10-1998-0704772A patent/KR100460364B1/ko not_active IP Right Cessation
- 1996-12-05 ES ES96943038T patent/ES2160264T3/es not_active Expired - Lifetime
- 1996-12-05 AU AU11906/97A patent/AU717705B2/en not_active Ceased
- 1996-12-05 BR BR9612235A patent/BR9612235A/pt not_active Application Discontinuation
- 1996-12-05 JP JP52325597A patent/JP3962089B2/ja not_active Expired - Lifetime
- 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 US US09/091,796 patent/US6140536A/en not_active Expired - Lifetime
- 1996-12-19 MY MYPI96005345A patent/MY117493A/en unknown
- 1996-12-19 ID IDP963809A patent/ID16007A/id unknown
- 1996-12-20 TW TW085115766A patent/TW371655B/zh active
- 1996-12-20 IN IN2209CA1996 patent/IN190919B/en unknown
-
1998
- 1998-06-17 MX MX9804881A patent/MX9804881A/es not_active IP Right Cessation
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002037769A (ja) * | 2000-07-25 | 2002-02-06 | Sumitomo Chem Co Ltd | 2−ヒドロキシ−4−メチルチオブタン酸の製造方法 |
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 |
JP2002105048A (ja) * | 2000-09-25 | 2002-04-10 | Sumitomo Chem Co Ltd | 2−ヒドロキシ−4−メチルチオブタンニトリルの製造方法 |
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 |
JP2002114758A (ja) * | 2000-10-11 | 2002-04-16 | Sumitomo Chem Co Ltd | 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 |
JP2002255927A (ja) * | 2001-02-27 | 2002-09-11 | Sumitomo Chem Co Ltd | 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 |
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 |
Also Published As
Publication number | Publication date |
---|---|
US6140536A (en) | 2000-10-31 |
EP0874811B1 (de) | 2001-06-13 |
BR9612235A (pt) | 1999-07-13 |
RU2160730C2 (ru) | 2000-12-20 |
DE19548538C2 (de) | 1997-12-18 |
WO1997023452A1 (de) | 1997-07-03 |
DE59607103D1 (de) | 2001-07-19 |
MY117493A (en) | 2004-07-31 |
EP0874811A1 (de) | 1998-11-04 |
KR19990076661A (ko) | 1999-10-15 |
AU1190697A (en) | 1997-07-17 |
ES2160264T3 (es) | 2001-11-01 |
TR199801190T2 (xx) | 1998-11-23 |
CN1205688A (zh) | 1999-01-20 |
TW371655B (en) | 1999-10-11 |
MX9804881A (es) | 1998-10-31 |
ID16007A (id) | 1997-08-28 |
CN1067377C (zh) | 2001-06-20 |
DE19548538A1 (de) | 1997-06-26 |
KR100460364B1 (ko) | 2005-05-20 |
JP3962089B2 (ja) | 2007-08-22 |
AU717705B2 (en) | 2000-03-30 |
IN190919B (ja) | 2003-08-30 |
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