JP5283897B2 - カルボン酸の脱カルボキシのための連続方法 - Google Patents
カルボン酸の脱カルボキシのための連続方法 Download PDFInfo
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- JP5283897B2 JP5283897B2 JP2007328947A JP2007328947A JP5283897B2 JP 5283897 B2 JP5283897 B2 JP 5283897B2 JP 2007328947 A JP2007328947 A JP 2007328947A JP 2007328947 A JP2007328947 A JP 2007328947A JP 5283897 B2 JP5283897 B2 JP 5283897B2
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- Prior art keywords
- decarboxylation
- formula
- carboxylic acid
- solvent
- water
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- 0 CNC(*)C(O)=O Chemical compound CNC(*)C(O)=O 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
R2=水素、アルキル、シクロアルキル]のカルボン酸の脱カルボキシのための連続方法であって、
I.溶媒中のカルボニル化合物を触媒として反応温度で装入し、
II.式Iのカルボン酸を水溶液、水性懸濁液として、又は水を含有する固形物として、前記触媒に反応区域中で計量供給し、
かつ
III.CO2、溶媒、水及び、式IIの所望の反応生成物及び/又は式IIIのアニオン
のカルボン酸が使用される。特にとりわけ有利には、本発明による方法において、リシン及びオルニチンから選択されたα−アミノ酸が使用される。
ジベンジルトルエン400.0g、イソホロン8.0g(0.06mol)及び脱泡剤4.0g(Wacker社のSilikonoel AK 350)を、内部温度計、撹拌シャフト(Ruehrhuelse)及び撹拌モータを有する翼付き撹拌機(Fluegelruehrer)、カルボン酸水溶液の計量供給のための1lのTelabポンプ、ラシヒリングで充填された10cmの長さの鏡面加工したカラム、水分離器、頂部温度のための取り付け具及び冷却器を有する2lの二重壁の、円柱状の反応容器中に装入し、撹拌下で加熱し、その際サーモスタットでのオイル供給温度(Oelvorlauftemperatur)は240℃であった。全体として、計量供給速度199g/hでもって、50%のリシン水溶液1195g(L−リシン 4.09molに相当)をポンプを用いてこの底部中に計量供給導入した。
Claims (6)
- 式I
R2=水素、アルキル、シクロアルキル]のカルボン酸の脱カルボキシのための連続方法であって、
I.150〜390℃の沸点を有する溶媒中のカルボニル化合物を触媒として反応温度で装入し、
II.式Iのカルボン酸を水溶液、水性懸濁液として、又は水を含有する固形物として、この触媒溶液に計量供給し、かつ
III.CO2、溶媒、水及び、式IIの所望の反応生成物及び/又は式IIIのアニオン
- 溶媒が、水連行作用を有することを特徴とする、請求項1記載の方法。
- カルボン酸の使用量に対して、触媒0.005〜10Moleq.を使用することを特徴とする、請求項1又は2記載の方法。
- カルボン酸の使用量に対して、触媒0.008〜0.05Moleq.を使用することを特徴とする、請求項3項記載の方法。
- 反応混合物に、脱泡剤を添加することを特徴とする、請求項1から4までのいずれか1項記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102006060908A DE102006060908A1 (de) | 2006-12-20 | 2006-12-20 | Kontinuierliches Verfahren zur Decarboxylierung von Carbonsäuren |
DE102006060908.5 | 2006-12-20 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008156355A JP2008156355A (ja) | 2008-07-10 |
JP5283897B2 true JP5283897B2 (ja) | 2013-09-04 |
Family
ID=39204647
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007328947A Expired - Fee Related JP5283897B2 (ja) | 2006-12-20 | 2007-12-20 | カルボン酸の脱カルボキシのための連続方法 |
Country Status (10)
Country | Link |
---|---|
US (1) | US7485756B2 (ja) |
EP (1) | EP1939168B1 (ja) |
JP (1) | JP5283897B2 (ja) |
KR (1) | KR101474562B1 (ja) |
CN (1) | CN101205160B (ja) |
AT (1) | ATE444277T1 (ja) |
DE (2) | DE102006060908A1 (ja) |
ES (1) | ES2332243T3 (ja) |
MX (1) | MX2007012351A (ja) |
TW (1) | TWI412511B (ja) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102006060908A1 (de) | 2006-12-20 | 2008-07-03 | Evonik Degussa Gmbh | Kontinuierliches Verfahren zur Decarboxylierung von Carbonsäuren |
JP6015494B2 (ja) * | 2013-03-01 | 2016-10-26 | 宇部興産株式会社 | アルキレンポリアミンの製造方法 |
US10487042B2 (en) | 2013-03-14 | 2019-11-26 | University Of Georgia Research Foundation, Inc. | Method for solvent-free decarboxylation of amino acids via imine formation |
US10118898B2 (en) | 2013-03-14 | 2018-11-06 | University Of Georgia Research Foundation, Inc. | Method for decarboxylation of amino acids via imine formation |
US9452954B2 (en) | 2013-03-14 | 2016-09-27 | University Of Georgia Research Foundation, Inc. | Method for decarboxylation of amino acids via imine formation |
CN103739552B (zh) * | 2014-01-24 | 2015-08-26 | 国药一心制药有限公司 | 二盐酸组胺的制备方法 |
CN105272994B (zh) * | 2015-11-09 | 2018-01-05 | 贝利化学(张家港)有限公司 | 一种反应装置 |
CN105968123B (zh) * | 2015-11-09 | 2018-09-25 | 贝利化学(张家港)有限公司 | 一种泡沫金属微反应器连续脱羧方法 |
EP3604268A4 (en) | 2017-03-28 | 2020-10-28 | Covestro Intellectual Property GmbH & Co. KG | ALIPHATIC AMINE, ITS PREPARATION PROCESS AND ITS APPLICATIONS |
WO2019008594A1 (en) * | 2017-07-03 | 2019-01-10 | Jubilant Generics Limited | CONTINUOUS PROCESS FOR THE PREPARATION OF 2- (1H-IMIDAZOL-4-YL) ETHANAMINE AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS |
US10889549B2 (en) | 2017-07-03 | 2021-01-12 | Jubilant Generics Limited | Continuous process for the preparation of 2-(1H-imidazol-4-yl) ethanamine and pharmaceutically acceptable salts thereof |
CN109836335B (zh) * | 2019-03-15 | 2021-11-05 | 宁波中科远东催化工程技术有限公司 | 戊二胺连续提纯装置及其连续提纯方法 |
CN110963923B (zh) * | 2019-12-16 | 2022-10-25 | 郑州中科新兴产业技术研究院 | 一种l-赖氨酸一步化学脱羧制备1,5-戊二胺的方法 |
CN111072493B (zh) * | 2019-12-19 | 2023-07-14 | 西安近代化学研究所 | 一种一步法制备1,5-戊二胺的方法 |
CN111087309B (zh) * | 2019-12-19 | 2023-03-21 | 西安近代化学研究所 | 一种一步法制备2-甲基丁胺的方法 |
CN112125809B (zh) * | 2020-10-14 | 2023-04-18 | 郑州中科新兴产业技术研究院 | 赖氨酸脱羧连续制备戊二胺的方法 |
Family Cites Families (14)
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JPS6023328A (ja) * | 1983-07-19 | 1985-02-05 | Sankyo Co Ltd | 脱炭酸反応 |
JP2862632B2 (ja) | 1990-04-26 | 1999-03-03 | キヤノン株式会社 | 基板の縦型搬送装置 |
JP3401295B2 (ja) * | 1993-08-10 | 2003-04-28 | ダイセル化学工業株式会社 | ハロゲン化脂肪族カルボニル化合物の製造方法 |
JP3710514B2 (ja) * | 1995-03-29 | 2005-10-26 | 株式会社日本触媒 | 2,3,5,6−テトラフルオロアニリンの製造方法 |
DE19627411A1 (de) | 1996-07-09 | 1998-01-15 | Bayer Ag | Verfahren zur Decarboxylierung halogenierter aromatischer Carbonsäuren |
FR2780966B1 (fr) * | 1998-07-10 | 2000-09-08 | Rhodia Chimie Sa | Procede de recuperation de composes dans les produits lourds issus de leur fabrication |
JP4139082B2 (ja) * | 1998-12-23 | 2008-08-27 | マキシム ファーマシューティカルス,インコーポレイテッド | ヒスタミンジヒドロクロリドの合成 |
JP4665185B2 (ja) | 2000-02-09 | 2011-04-06 | 東レ・ファインケミカル株式会社 | アミン類の製造法 |
JP4196620B2 (ja) * | 2002-04-08 | 2008-12-17 | 東レ株式会社 | ポリアミド原料用カダベリンの製造方法 |
JP2005029542A (ja) * | 2003-07-11 | 2005-02-03 | Toyohashi University Of Technology | 高温高圧水を用いたグルタミン酸からのγ−アミノ酪酸の合成方法 |
US7256161B2 (en) * | 2003-11-13 | 2007-08-14 | Chevron Oronite Company Llc | Process for making group II metal carbonated, overbased Mannich condensation products of alkylphenols |
US7223873B2 (en) * | 2004-03-30 | 2007-05-29 | Daisco Co., Ltd | Process for preparing amines |
JP2005314375A (ja) * | 2004-03-30 | 2005-11-10 | Daiso Co Ltd | アミン類の製造法 |
DE102006060908A1 (de) | 2006-12-20 | 2008-07-03 | Evonik Degussa Gmbh | Kontinuierliches Verfahren zur Decarboxylierung von Carbonsäuren |
-
2006
- 2006-12-20 DE DE102006060908A patent/DE102006060908A1/de not_active Withdrawn
-
2007
- 2007-10-04 MX MX2007012351A patent/MX2007012351A/es active IP Right Grant
- 2007-10-25 EP EP07119244A patent/EP1939168B1/de not_active Not-in-force
- 2007-10-25 ES ES07119244T patent/ES2332243T3/es active Active
- 2007-10-25 DE DE502007001622T patent/DE502007001622D1/de active Active
- 2007-10-25 AT AT07119244T patent/ATE444277T1/de not_active IP Right Cessation
- 2007-12-13 TW TW096147685A patent/TWI412511B/zh not_active IP Right Cessation
- 2007-12-18 KR KR1020070133196A patent/KR101474562B1/ko not_active IP Right Cessation
- 2007-12-19 CN CN2007101603133A patent/CN101205160B/zh not_active Expired - Fee Related
- 2007-12-20 JP JP2007328947A patent/JP5283897B2/ja not_active Expired - Fee Related
- 2007-12-20 US US11/961,109 patent/US7485756B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US20080214864A1 (en) | 2008-09-04 |
US7485756B2 (en) | 2009-02-03 |
KR20080058206A (ko) | 2008-06-25 |
TWI412511B (zh) | 2013-10-21 |
MX2007012351A (es) | 2008-10-28 |
KR101474562B1 (ko) | 2014-12-18 |
EP1939168A1 (de) | 2008-07-02 |
CN101205160A (zh) | 2008-06-25 |
JP2008156355A (ja) | 2008-07-10 |
EP1939168B1 (de) | 2009-09-30 |
DE502007001622D1 (de) | 2009-11-12 |
ATE444277T1 (de) | 2009-10-15 |
DE102006060908A1 (de) | 2008-07-03 |
ES2332243T3 (es) | 2010-01-29 |
CN101205160B (zh) | 2012-01-18 |
TW200902480A (en) | 2009-01-16 |
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