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WO2004041785A1 - Procede de preparation de vinylpyridine a partir de picoline sur des zeolites modifies - Google Patents

Procede de preparation de vinylpyridine a partir de picoline sur des zeolites modifies Download PDF

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Publication number
WO2004041785A1
WO2004041785A1 PCT/IB2002/004653 IB0204653W WO2004041785A1 WO 2004041785 A1 WO2004041785 A1 WO 2004041785A1 IB 0204653 W IB0204653 W IB 0204653W WO 2004041785 A1 WO2004041785 A1 WO 2004041785A1
Authority
WO
WIPO (PCT)
Prior art keywords
picoline
zsm
vinylpyridine
catalyst
modified
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.)
Ceased
Application number
PCT/IB2002/004653
Other languages
English (en)
Inventor
Shivanand Janardan Kulkarni
Gangapuram Madhavi
Venkataraman Viswanathan
Kondapuram Vijaya Raghavan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Council of Scientific and Industrial Research CSIR
Original Assignee
Council of Scientific and Industrial Research CSIR
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Council of Scientific and Industrial Research CSIR filed Critical Council of Scientific and Industrial Research CSIR
Priority to EP02779826A priority Critical patent/EP1565439A1/fr
Priority to PCT/IB2002/004653 priority patent/WO2004041785A1/fr
Priority to AU2002343158A priority patent/AU2002343158A1/en
Priority to JP2004549391A priority patent/JP4545593B2/ja
Publication of WO2004041785A1 publication Critical patent/WO2004041785A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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

Definitions

  • the main objective of the present invention is to provide a process for the synthesis of vinylpyridines over modified zeolites in a heterogeneous eco-friendly method.
  • Another objective ⁇ of the present invention is to provide a process for the preparation of 2-vinylpyridine in high yield and high selectivity.
  • the present invention provides an improved process for the preparation of vinylpyridine from corresponding picoline over modified zeolite catalyst in vapour phase which comprises reacting picoline with formaldehyde with a molar ratio of formaldehyde to . picoline in the range of 1:1. to 4:1, at a temperature ranging between 200°
  • one of the reactant picoline is selected from 2-picoline and 4-picoline.
  • the precursor to modify ZSM-5 catalyst by potassium ion or other elements is varied like KO l Bu, KOH, KF, KNO 3 , K 3 PO 4 and KOAc to improve the yield ,and selectivity of vinylpyridine.
  • the calcination temperature of modified zeolite is varied from 400°C to ⁇ 7:0Q?C.'
  • the experimental conditions are as explained in Example-15.
  • the weight of calcium was 3wt% in ZSM-5 catalyst.
  • the liquid product selectivity of 4-vinylpyridine was 83.9% at 37.2% conversion of 4-picoline during i

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé amélioré et non polluant de préparation de vinylpyridine à partir de la picoline correspondante sur un catalyseur zéolitique modifié en phase vapeur. Ce procédé consiste à faire réagir la picoline avec du formaldéhyde, le rapport molaire entre le formaldéhyde et la picoline étant compris entre 1:1 et 4:1, à une température comprise entre 200 DEG C et 450 DEG C, à une vitesse spatiale comprise entre 0,25 h.<-1> et 1,00 h.<-1> sur un catalyseur zéolitique modifié commercial pour obtenir un rendement et une sélectivité élevés du produit souhaité.
PCT/IB2002/004653 2002-11-06 2002-11-06 Procede de preparation de vinylpyridine a partir de picoline sur des zeolites modifies Ceased WO2004041785A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP02779826A EP1565439A1 (fr) 2002-11-06 2002-11-06 Procede de preparation de vinylpyridine a partir de picoline sur des zeolites modifies
PCT/IB2002/004653 WO2004041785A1 (fr) 2002-11-06 2002-11-06 Procede de preparation de vinylpyridine a partir de picoline sur des zeolites modifies
AU2002343158A AU2002343158A1 (en) 2002-11-06 2002-11-06 Process for the preparation of vinylpyridine from picoline over modified zeolites
JP2004549391A JP4545593B2 (ja) 2002-11-06 2002-11-06 変性ゼオライト上でピコリンからビニルピリジンを製造する方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IB2002/004653 WO2004041785A1 (fr) 2002-11-06 2002-11-06 Procede de preparation de vinylpyridine a partir de picoline sur des zeolites modifies

Publications (1)

Publication Number Publication Date
WO2004041785A1 true WO2004041785A1 (fr) 2004-05-21

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2002/004653 Ceased WO2004041785A1 (fr) 2002-11-06 2002-11-06 Procede de preparation de vinylpyridine a partir de picoline sur des zeolites modifies

Country Status (4)

Country Link
EP (1) EP1565439A1 (fr)
JP (1) JP4545593B2 (fr)
AU (1) AU2002343158A1 (fr)
WO (1) WO2004041785A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112028817A (zh) * 2019-12-18 2020-12-04 上海中西三维药业有限公司 一种2-乙烯基吡啶的制备方法
CN112108177A (zh) * 2020-09-11 2020-12-22 北京弗莱明科技有限公司 一种乙烯基氮苯的制备方法
CN118577209A (zh) * 2024-08-01 2024-09-03 淄博奥固特科技有限公司 一种高收率2-乙烯基吡啶的合成工艺

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3316929A1 (de) * 1983-05-09 1984-11-15 Hoechst Ag, 6230 Frankfurt Verfahren zur herstellung von styrol und ethylbenzol aus toluol
WO2002034720A1 (fr) * 2000-10-20 2002-05-02 Reilly Industries, Inc. Procede de preparation d'heterocycles portant des substituants vinyliques

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3316929A1 (de) * 1983-05-09 1984-11-15 Hoechst Ag, 6230 Frankfurt Verfahren zur herstellung von styrol und ethylbenzol aus toluol
WO2002034720A1 (fr) * 2000-10-20 2002-05-02 Reilly Industries, Inc. Procede de preparation d'heterocycles portant des substituants vinyliques

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; ARCHIER, D. ET AL: "Lateral-chain methylation of toluene over boron and/or zinc modified cesium-X zeolite", XP002233944, retrieved from STN Database accession no. 123:8888 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; KONOVAL'CHIKOV, O. D. ET AL: "Simultaneous production of ethylbenzene and styrene", XP002233942, retrieved from STN Database accession no. 73:110317 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; MOON, S. K. ET AL: "Influence of methanol-decomposition in the side-chain alkylation of toluene with methanol", XP002233945, retrieved from STN Database accession no. 109:210601 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; WU, CHUANCHANG ET AL: "Relationship between the acid-base properties of zeolite surface and the activity of side-chain alkylation of toluene with methanol", XP002233943, retrieved from STN Database accession no. 111:235517 *
GAODENG XUEXIAO HUAXUE XUEBAO (1989), 10(4), 383-6 *
HWAHAK KONGHAK (1987), 25(6), 601-6 *
PROC. INT. ZEOLITE CONF., 9TH (1993), MEETING DATE 1992, VOLUME 2, 525-34. EDITOR(S): VON BALLMOOS, RONALD;HIGGINS, JOHN B.; TREACY, MICHAEL M. J. PUBLISHER: BUTTERWORTH-HEINEMANN, BOSTON, MASS. *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112028817A (zh) * 2019-12-18 2020-12-04 上海中西三维药业有限公司 一种2-乙烯基吡啶的制备方法
CN112028817B (zh) * 2019-12-18 2023-10-03 上海中西三维药业有限公司 一种2-乙烯基吡啶的制备方法
CN112108177A (zh) * 2020-09-11 2020-12-22 北京弗莱明科技有限公司 一种乙烯基氮苯的制备方法
CN118577209A (zh) * 2024-08-01 2024-09-03 淄博奥固特科技有限公司 一种高收率2-乙烯基吡啶的合成工艺

Also Published As

Publication number Publication date
JP2006515569A (ja) 2006-06-01
EP1565439A1 (fr) 2005-08-24
AU2002343158A1 (en) 2004-06-07
JP4545593B2 (ja) 2010-09-15

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