JPH08510447A - 2−メチル−1,5−ジアミノペンタンの触媒環化による3−メチルピペリジンおよび3−メチルピリジンの製造方法 - Google Patents
2−メチル−1,5−ジアミノペンタンの触媒環化による3−メチルピペリジンおよび3−メチルピリジンの製造方法Info
- Publication number
- JPH08510447A JPH08510447A JP6521673A JP52167394A JPH08510447A JP H08510447 A JPH08510447 A JP H08510447A JP 6521673 A JP6521673 A JP 6521673A JP 52167394 A JP52167394 A JP 52167394A JP H08510447 A JPH08510447 A JP H08510447A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- methyl
- diaminopentane
- hours
- methylpiperidine
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/08—Preparation by ring-closure
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/12—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with only hydrogen atoms attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.2−メチル−1,5−ジアミノペンタンから気相において3−メチル ピペリジンを製造する方法において、ガス状の2−メチル−1,5−ジアミノペ ンタンを、温度300〜400℃で、大気を超える圧力0〜10バールで、活性 成分としてAlおよび(または)Si元素のうち少なくとも一つの酸化物を含み 、表面の酸性および塩基性の中心の比が2を超え、比表面積が40m2/gを超え る触媒を通すことを特徴とする製造方法。 2.使用する触媒が、活性化Al2O3またはアルミニウム/シリコン混合 酸化物であることを特徴とする請求の範囲第1項に記載の製造方法。 3.使用する触媒が、天然または合成ゼオライトであることを特徴とする 請求の範囲第1項に記載の製造方法。 4.3−メチルピリジンを製造する方法において、初めに、出発原料2− メチル−1,5−ジアミノペンタンから、気相において、300〜400℃、大 気を超える圧力0〜10バールで、活性成分としてAlおよび(または)Siの うち少なくとも一つの酸化物を含み、表面の酸性および塩基性の中心の比が2を 超え、比表面積が40m2/gを超える触媒を通すことによって3−メチルピペリ ジンが製造され、続いて、その結果生じた3−メチルピペリジンを、脱水素触媒 を、好ましくは220〜400℃で、通過させることを特徴とする製造方法。 5.使用する脱水素触媒が、支持体上の貴金属であることを特徴とする請 求の範囲第4項に記載の製造方法。 6.使用する貴金属が、パラジウムまたは白金であることを特徴とする請 求の範囲第5項に記載の製造方法。 7.使用する脱水素触媒が、可溶性のパラジウム錯体とのイオン交換によ って製造される、非晶質アルミニウム/ケイ素酸化物上のパラジウムであること を特徴とする請求の範囲第6項に記載の製造方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1014/93-0 | 1993-04-02 | ||
CH101493 | 1993-04-02 | ||
CH37/94-3 | 1994-01-06 | ||
CH3794A CH686135A5 (de) | 1994-01-06 | 1994-01-06 | Verfahren zur Herstellung von 3-Methylpiperidin und 3-Methylpyridin. |
PCT/EP1994/001005 WO1994022824A1 (de) | 1993-04-02 | 1994-03-30 | Verfahren zur herstellung von 3-methylpiperidin und 3-methylpyridin durch katalytische cyclisierung von 2-methyl-1, 5-diaminopentan |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH08510447A true JPH08510447A (ja) | 1996-11-05 |
JP3520519B2 JP3520519B2 (ja) | 2004-04-19 |
Family
ID=25683321
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP52167394A Expired - Fee Related JP3520519B2 (ja) | 1993-04-02 | 1994-03-30 | 2−メチル−1,5−ジアミノペンタンの触媒環化による3−メチルピペリジンおよび3−メチルピリジンの製造方法 |
Country Status (27)
Country | Link |
---|---|
US (1) | US5714610A (ja) |
EP (1) | EP0691955B1 (ja) |
JP (1) | JP3520519B2 (ja) |
KR (1) | KR100276748B1 (ja) |
AT (1) | ATE153658T1 (ja) |
BG (1) | BG62767B1 (ja) |
BR (1) | BR9405915A (ja) |
CA (1) | CA2159586C (ja) |
CZ (1) | CZ287321B6 (ja) |
DE (1) | DE59402925D1 (ja) |
DK (1) | DK0691955T3 (ja) |
EE (1) | EE03176B1 (ja) |
ES (1) | ES2104377T3 (ja) |
FI (1) | FI112473B (ja) |
GE (1) | GEP20012441B (ja) |
GR (1) | GR3024294T3 (ja) |
HR (1) | HRP940211B1 (ja) |
IL (1) | IL109173A (ja) |
LV (1) | LV12129B (ja) |
NO (1) | NO303937B1 (ja) |
PL (1) | PL177347B1 (ja) |
RO (2) | RO117914B1 (ja) |
RU (1) | RU2127726C1 (ja) |
SK (1) | SK281702B6 (ja) |
TW (1) | TW239129B (ja) |
UA (1) | UA42717C2 (ja) |
WO (1) | WO1994022824A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013507246A (ja) * | 2009-10-16 | 2013-03-04 | ロンザ リミテッド | メチルピリジンの調製のための触媒 |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GEP20012441B (en) * | 1993-04-02 | 2001-05-25 | Lonza Ag | Process for Preparing 3-Methylpiperidine and 3-Methylpyridine |
ZA968485B (en) * | 1995-11-01 | 1997-05-20 | Lonza Ag | Process for preparing nicotinamide |
CH689831A5 (de) * | 1995-11-07 | 1999-12-15 | Eprova Ag | Stabile kristalline Tetrahydrofolsaeure-Salze. |
DE10144631A1 (de) * | 2001-09-11 | 2003-03-27 | Basf Ag | Verfahren zur Herstellung von Pyrrol und Pyridin |
US6995112B2 (en) * | 2002-11-08 | 2006-02-07 | Chevron U.S.A. Inc. | Highly homogeneous amorphous silica-alumina catalyst composition |
CN102164895A (zh) * | 2008-09-26 | 2011-08-24 | 帝斯曼知识产权资产管理有限公司 | 3-甲基吡啶的制备方法 |
US8530664B2 (en) * | 2009-10-16 | 2013-09-10 | Lonza Ltd. | Catalysts for the preparation of methylpyridine |
RU2474473C1 (ru) * | 2011-09-16 | 2013-02-10 | Российская Федерация, От Имени Которой Выступает Министерство Промышленности И Торговли Российской Федерации | КАТАЛИЗАТОР, СПОСОБ ЕГО ПРИГОТОВЛЕНИЯ И СПОСОБ ПОЛУЧЕНИЯ β-ПИКОЛИНА |
CN103044317B (zh) * | 2013-01-07 | 2015-07-29 | 清华大学 | 制备3-甲基吡啶的方法和系统 |
CN104841475B (zh) * | 2014-02-17 | 2018-09-11 | 凯赛(金乡)生物材料有限公司 | 一种用于制备哌啶的改性分子筛催化剂及其制备方法和应用 |
CN112010802B (zh) * | 2020-08-13 | 2022-03-29 | 浙江新和成股份有限公司 | 3-甲基吡啶的连续制备方法 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB755534A (en) * | 1953-12-16 | 1956-08-22 | Ici Ltd | Catalytic cyclisation of pentamethylene diamine |
FR1115492A (fr) * | 1953-12-16 | 1956-04-25 | Ici Ltd | Fabrication de la pipéridine et de la pyridine |
US3903079A (en) * | 1971-08-27 | 1975-09-02 | Celanese Corp | Production of polymethylenimines by cycloammonolysis |
DE2519529B2 (de) * | 1975-05-02 | 1979-08-09 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von 3-Methylpyridin |
FR2503156A1 (fr) * | 1981-04-01 | 1982-10-08 | Rhone Poulenc Spec Chim | Procede de preparation de pyridine et de pyridines substituees |
CH654576A5 (en) * | 1982-07-29 | 1986-02-28 | Lonza Ag | Process for the preparation of 3-methylpyridine |
GB8425969D0 (en) * | 1984-10-15 | 1984-11-21 | Ici Plc | Heterocyclic compounds |
US5179014A (en) * | 1985-01-08 | 1993-01-12 | Nitto Chemical Industry Co., Ltd. | Process for the preparation of amides using microorganisms |
JPS61162193A (ja) * | 1985-01-08 | 1986-07-22 | Nitto Chem Ind Co Ltd | 微生物によるアミド類の製造法 |
DD274631A5 (de) * | 1987-09-18 | 1989-12-27 | Kk | Verfahren zur biologischen herstellung von amiden |
US5149816A (en) * | 1988-07-11 | 1992-09-22 | Reilly Industries | High temperature process for selective production of 3-methylpyridine |
IL90918A (en) * | 1988-07-11 | 1993-05-13 | Reilly Ind Inc | Process for selective production of 3-methylpyridine |
US5258305A (en) * | 1991-09-13 | 1993-11-02 | Nitto Chemical Industry Co., Ltd. | Manufacture of optically active 2-phenylpropionic acid and 2-phenylpropionamide from the nitrile using Rhodococcus equi |
GEP20012441B (en) * | 1993-04-02 | 2001-05-25 | Lonza Ag | Process for Preparing 3-Methylpiperidine and 3-Methylpyridine |
CZ338596A3 (en) * | 1994-05-23 | 1997-07-16 | Lonza Ag | Catalytic mixture for oxidative amonolysis of alkyl pyridines, process of its preparation and use |
-
1994
- 1994-03-25 GE GEAP19941824A patent/GEP20012441B/en unknown
- 1994-03-30 UA UA95094345A patent/UA42717C2/uk unknown
- 1994-03-30 CZ CZ19952542A patent/CZ287321B6/cs not_active IP Right Cessation
- 1994-03-30 ES ES94913092T patent/ES2104377T3/es not_active Expired - Lifetime
- 1994-03-30 US US08/525,744 patent/US5714610A/en not_active Expired - Lifetime
- 1994-03-30 DE DE59402925T patent/DE59402925D1/de not_active Expired - Lifetime
- 1994-03-30 WO PCT/EP1994/001005 patent/WO1994022824A1/de active IP Right Grant
- 1994-03-30 CA CA002159586A patent/CA2159586C/en not_active Expired - Lifetime
- 1994-03-30 RO RO95-01676A patent/RO117914B1/ro unknown
- 1994-03-30 AT AT94913092T patent/ATE153658T1/de active
- 1994-03-30 RO ROA200201005A patent/RO121267B1/ro unknown
- 1994-03-30 PL PL94311006A patent/PL177347B1/pl unknown
- 1994-03-30 BR BR9405915A patent/BR9405915A/pt not_active IP Right Cessation
- 1994-03-30 EP EP94913092A patent/EP0691955B1/de not_active Expired - Lifetime
- 1994-03-30 JP JP52167394A patent/JP3520519B2/ja not_active Expired - Fee Related
- 1994-03-30 KR KR1019950704170A patent/KR100276748B1/ko not_active IP Right Cessation
- 1994-03-30 HR HR940211A patent/HRP940211B1/xx not_active IP Right Cessation
- 1994-03-30 SK SK1226-95A patent/SK281702B6/sk not_active IP Right Cessation
- 1994-03-30 DK DK94913092.6T patent/DK0691955T3/da not_active Application Discontinuation
- 1994-03-30 RU RU95121817A patent/RU2127726C1/ru active
- 1994-03-30 IL IL10917394A patent/IL109173A/en not_active IP Right Cessation
- 1994-04-23 TW TW083103633A patent/TW239129B/zh not_active IP Right Cessation
- 1994-06-29 EE EE9400069A patent/EE03176B1/xx not_active IP Right Cessation
-
1995
- 1995-09-29 NO NO953896A patent/NO303937B1/no not_active IP Right Cessation
- 1995-09-29 FI FI954660A patent/FI112473B/fi not_active IP Right Cessation
- 1995-10-25 BG BG100095A patent/BG62767B1/bg unknown
-
1997
- 1997-07-30 GR GR970401943T patent/GR3024294T3/el unknown
-
1998
- 1998-05-28 LV LVP-98-124A patent/LV12129B/lv unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013507246A (ja) * | 2009-10-16 | 2013-03-04 | ロンザ リミテッド | メチルピリジンの調製のための触媒 |
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