JP4521277B2 - 3−メチルチオプロパナールの製造方法 - Google Patents
3−メチルチオプロパナールの製造方法 Download PDFInfo
- Publication number
- JP4521277B2 JP4521277B2 JP2004546263A JP2004546263A JP4521277B2 JP 4521277 B2 JP4521277 B2 JP 4521277B2 JP 2004546263 A JP2004546263 A JP 2004546263A JP 2004546263 A JP2004546263 A JP 2004546263A JP 4521277 B2 JP4521277 B2 JP 4521277B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- reaction
- process according
- mtpa
- acrolein
- 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 - Fee Related
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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
- C07C319/18—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by addition of thiols to unsaturated compounds
-
- 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
-
- 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
- C07C323/22—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 doubly-bound oxygen atoms bound to the same carbon skeleton
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
以下の実施例においては、従来の触媒(触媒1A)と比較した、本発明に従ったオレフィン/メルカプタン触媒(1)の収率と動的性能(kinetic performance)を評価する。
反応剤の転化率と得られる生成物の量を有機酸の不存在下(触媒2.1及び2.3)及び存在下(触媒2.2及び2.4)で2種の異なるアルキルモルホリンを使用して測定した。ピラジン及びイミダゾールを使用して、同様に有機酸の不存在下(触媒2A及び2C)及び存在下(触媒2B及び2D)で比較試験を行った。
本発明に従った触媒(触媒3)を使用して製造されたMTPAの安定性を、従来から既知の触媒(触媒3.A及び3.B)を使用して製造されたMTPAの安定性と比較した。
アルデヒド反応を触媒するために、N-メチルモルホリンと酢酸(モル比 2/1)を使用して実施例1で得られた生成物を、生成物流とシアン化水素とを反応させることによりHMTBNに転化した。40.5g(0.338モル)のMTPAと26.4gの水を、撹拌しながら、150mlのジャケット付きガラス製反応器に導入した。
Claims (16)
- メチルメルカプタンとアクロレインを含有する反応媒体を有機塩基からなる触媒の存在下で反応させることからなる 3-メチルチオプロパナールの製造方法において、有機塩基がN-アルキルモルホリン化合物であることを特徴とする 3-メチルチオプロパナールの製造方法。
- 触媒がC1-C6アルキルモルホリンである、請求項1に記載の方法。
- 触媒がメチルモルホリン又はエチルモルホリンである、請求項2に記載の方法。
- メチルメルカプタンに対する有機塩基のモル比が0.0001〜0.05である、前記請求項のいずれか一つに記載の方法。
- メチルメルカプタンに対する有機塩基のモル比が0.001〜0.01である、請求項4に記載の方法。
- アクロレインに対するメチルメルカプタンのモル比が0.9〜2である、前記請求項のいずれか一つに記載の方法。
- アクロレインに対するメチルメルカプタンのモル比が1〜1.2である、請求項6に記載の方法。
- 触媒が更に有機酸を含有している、前記請求項のいずれか一つに記載の方法。
- 有機酸はギ酸、酢酸、プロパン酸及びブタン酸から選ばれる、請求項8に記載の方法。
- 有機酸は酢酸である、請求項9に記載の方法。
- 有機酸に対する触媒のモル比は0.1〜2である請求項8〜10のいずれか一つに記載の方法。
- 有機酸に対する触媒のモル比は0.2〜1である請求項11に記載の方法。
- 20〜70℃の温度で行われる、前記請求項のいずれか一つに記載の方法。
- 30〜50℃の温度で行われる、請求項13に記載の方法。
- 大気圧下で行われる、前記請求項のいずれか一つに記載の方法。
- (a)メチルメルカプタンとアクロレインを含有する反応媒体を有機塩基(この有機塩基はN-アルキルモルホリン化合物である)からなる触媒の存在下で反応させることにより3-メチルチオプロパナールと上記触媒とを含有する生成物流を生成させる第1工程;及び(b)上記生成物流を触媒の存在下でシアン化水素と反応させ、それによって、2-ヒドロキシ-4-(メチルチオ)ブタンニトリルを製造する第2工程からなる、2-ヒドロキシ-4-(メチルチオ)ブタンニトリルの製造方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP20020356211 EP1413573A1 (en) | 2002-10-24 | 2002-10-24 | Process for the production of 3-methylthiopropanal |
PCT/IB2003/004557 WO2004037774A1 (en) | 2002-10-24 | 2003-10-14 | Process for the production of 3-methylthiopropanal |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2006515834A JP2006515834A (ja) | 2006-06-08 |
JP2006515834A5 JP2006515834A5 (ja) | 2010-04-22 |
JP4521277B2 true JP4521277B2 (ja) | 2010-08-11 |
Family
ID=32050124
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004546263A Expired - Fee Related JP4521277B2 (ja) | 2002-10-24 | 2003-10-14 | 3−メチルチオプロパナールの製造方法 |
Country Status (21)
Country | Link |
---|---|
US (1) | US7256315B2 (ja) |
EP (2) | EP1413573A1 (ja) |
JP (1) | JP4521277B2 (ja) |
KR (1) | KR100984125B1 (ja) |
CN (1) | CN1277816C (ja) |
AR (1) | AR041714A1 (ja) |
AT (1) | ATE371642T1 (ja) |
AU (1) | AU2003267771A1 (ja) |
BR (1) | BR0315385A (ja) |
CA (1) | CA2495746A1 (ja) |
DE (1) | DE60316011T2 (ja) |
ES (1) | ES2291662T3 (ja) |
MX (1) | MXPA05004158A (ja) |
MY (1) | MY134665A (ja) |
NO (1) | NO20052471L (ja) |
PL (1) | PL375101A1 (ja) |
RU (1) | RU2336266C2 (ja) |
TW (1) | TWI319391B (ja) |
UA (1) | UA78613C2 (ja) |
WO (1) | WO2004037774A1 (ja) |
ZA (1) | ZA200501389B (ja) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101258128A (zh) * | 2005-09-12 | 2008-09-03 | 住友化学株式会社 | 制备4-(甲硫基)丁-1,2-二醇的方法 |
DE102008042932A1 (de) * | 2008-10-17 | 2010-04-22 | Evonik Degussa Gmbh | Herstellung und Verwendung von Methionylmethionin als Futtermitteladditiv für Fische und Krustentiere |
FR2938535B1 (fr) | 2008-11-20 | 2012-08-17 | Arkema France | Procede de fabrication de methylmercaptopropionaldehyde et de methionine a partir de matieres renouvelables |
JP5182199B2 (ja) * | 2009-04-06 | 2013-04-10 | 住友化学株式会社 | 3−メチルチオプロパナールの製造方法 |
JP5182198B2 (ja) * | 2009-04-06 | 2013-04-10 | 住友化学株式会社 | 3−メチルチオプロパナールの製造方法 |
JP5402864B2 (ja) * | 2010-07-20 | 2014-01-29 | 住友化学株式会社 | 3−メチルチオプロパナールの製造方法 |
CN109160893A (zh) * | 2018-10-15 | 2019-01-08 | 禄丰天宝磷化工有限公司 | 一种甲硒基丙醛的制备方法 |
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 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2427582A (en) * | 1944-09-27 | 1947-09-16 | Du Pont | Beta (acylthio) aldehydes and ketones and their preparation |
US2776996A (en) * | 1955-12-22 | 1957-01-08 | Du Pont | Manufacture of beta-methylmercaptopropionaldehyde |
FR2314917A1 (fr) * | 1975-06-20 | 1977-01-14 | Rhone Poulenc Ind | Procede de fabrication de l'aldehyde beta-methylthiopropionique |
JPS57197262A (en) * | 1981-05-29 | 1982-12-03 | Res Dev Corp Of Japan | Production of optically active beta-arylthio or alkylthioketone |
JP3219544B2 (ja) * | 1992-05-21 | 2001-10-15 | ダイセル化学工業株式会社 | 2−ヒドロキシ−4−メチルチオブタン酸の製造法 |
MY109603A (en) * | 1992-05-21 | 1997-03-31 | Daicel Chem | Process for producing 2-hydroxy-4-methylthiobutanoic acid |
US5637766A (en) * | 1993-06-08 | 1997-06-10 | Novus International, Inc. | Process for the preparation of 3-(methylthio) propanal |
US5663409A (en) * | 1995-06-07 | 1997-09-02 | Novus International, Inc. | Process for the preparation of 3-(methylthio) propanal and 2-hydroxy-4-(methylthio) butanenitrile |
US5696282A (en) * | 1996-03-26 | 1997-12-09 | Phillips Petroleum Company | Process for producing organosulfur compounds |
-
2002
- 2002-10-24 EP EP20020356211 patent/EP1413573A1/en not_active Withdrawn
-
2003
- 2003-10-14 DE DE60316011T patent/DE60316011T2/de not_active Expired - Lifetime
- 2003-10-14 JP JP2004546263A patent/JP4521277B2/ja not_active Expired - Fee Related
- 2003-10-14 UA UAA200504636A patent/UA78613C2/uk unknown
- 2003-10-14 US US10/524,548 patent/US7256315B2/en not_active Expired - Lifetime
- 2003-10-14 AT AT03748466T patent/ATE371642T1/de not_active IP Right Cessation
- 2003-10-14 PL PL03375101A patent/PL375101A1/xx not_active IP Right Cessation
- 2003-10-14 MX MXPA05004158A patent/MXPA05004158A/es not_active Application Discontinuation
- 2003-10-14 CN CNB2003801015894A patent/CN1277816C/zh not_active Expired - Fee Related
- 2003-10-14 KR KR1020057007069A patent/KR100984125B1/ko active IP Right Grant
- 2003-10-14 CA CA002495746A patent/CA2495746A1/en not_active Abandoned
- 2003-10-14 WO PCT/IB2003/004557 patent/WO2004037774A1/en active IP Right Grant
- 2003-10-14 AU AU2003267771A patent/AU2003267771A1/en not_active Abandoned
- 2003-10-14 ES ES03748466T patent/ES2291662T3/es not_active Expired - Lifetime
- 2003-10-14 EP EP03748466A patent/EP1556343B1/en not_active Expired - Lifetime
- 2003-10-14 RU RU2005105040/04A patent/RU2336266C2/ru active
- 2003-10-14 BR BR0315385-1A patent/BR0315385A/pt not_active IP Right Cessation
- 2003-10-17 TW TW092128917A patent/TWI319391B/zh not_active IP Right Cessation
- 2003-10-20 MY MYPI20033986A patent/MY134665A/en unknown
- 2003-10-24 AR ARP030103885A patent/AR041714A1/es not_active Application Discontinuation
-
2005
- 2005-02-16 ZA ZA200501389A patent/ZA200501389B/en unknown
- 2005-05-23 NO NO20052471A patent/NO20052471L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
EP1413573A1 (en) | 2004-04-28 |
MY134665A (en) | 2007-12-31 |
AU2003267771A1 (en) | 2004-05-13 |
ZA200501389B (en) | 2006-07-26 |
CA2495746A1 (en) | 2004-05-06 |
UA78613C2 (en) | 2007-04-10 |
TW200413299A (en) | 2004-08-01 |
KR20050067423A (ko) | 2005-07-01 |
TWI319391B (en) | 2010-01-11 |
NO20052471L (no) | 2005-07-25 |
DE60316011D1 (de) | 2007-10-11 |
RU2005105040A (ru) | 2005-10-27 |
KR100984125B1 (ko) | 2010-09-28 |
ES2291662T3 (es) | 2008-03-01 |
PL375101A1 (en) | 2005-11-14 |
US20050240048A1 (en) | 2005-10-27 |
EP1556343A1 (en) | 2005-07-27 |
DE60316011T2 (de) | 2008-05-15 |
CN1705641A (zh) | 2005-12-07 |
BR0315385A (pt) | 2005-08-23 |
US7256315B2 (en) | 2007-08-14 |
EP1556343B1 (en) | 2007-08-29 |
NO20052471D0 (no) | 2005-05-23 |
CN1277816C (zh) | 2006-10-04 |
WO2004037774A1 (en) | 2004-05-06 |
JP2006515834A (ja) | 2006-06-08 |
AR041714A1 (es) | 2005-05-26 |
MXPA05004158A (es) | 2005-08-03 |
ATE371642T1 (de) | 2007-09-15 |
RU2336266C2 (ru) | 2008-10-20 |
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