CA2552158A1 - Catalyst for synthesis of 2- and 4-picolines, process for preparing 2- and 4-picoline and process for preparing the catalyst - Google Patents

Catalyst for synthesis of 2- and 4-picolines, process for preparing 2- and 4-picoline and process for preparing the catalyst Download PDF

Info

Publication number
CA2552158A1
CA2552158A1 CA002552158A CA2552158A CA2552158A1 CA 2552158 A1 CA2552158 A1 CA 2552158A1 CA 002552158 A CA002552158 A CA 002552158A CA 2552158 A CA2552158 A CA 2552158A CA 2552158 A1 CA2552158 A1 CA 2552158A1
Authority
CA
Canada
Prior art keywords
acid
catalyst
range
alumina
group
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
Application number
CA002552158A
Other languages
French (fr)
Other versions
CA2552158C (en
Inventor
Pashupati Dutta
Subhash Chandra Roy
Shyam Kishor Roy
Tarun Kanti Goswami
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
Individual
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 Individual filed Critical Individual
Publication of CA2552158A1 publication Critical patent/CA2552158A1/en
Application granted granted Critical
Publication of CA2552158C publication Critical patent/CA2552158C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
    • B01J21/04—Alumina
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • B01J21/08—Silica
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/12—Silica and alumina
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/16—Clays or other mineral silicates
    • 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
    • B01J23/002—Mixed oxides other than spinels, e.g. perovskite
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
    • B01J27/198—Vanadium
    • B01J27/199—Vanadium with chromium, molybdenum, tungsten or polonium
    • 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
    • C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
    • C07D213/10—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from acetaldehyde or cyclic polymers thereof
    • 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
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Catalysts (AREA)

Abstract

The present invention provides a catalyst comprising a composite of a heteropolyacid impregnated on a support for the synthesis of 2- and 4-picolines and a process for the preparation thereof and use thereof for the synthesis of 2- and 4-picolines.

Claims (17)

1. A catalyst useful for synthesis of 2- and 4- Picolines which comprises a heteropoly acid selected from the group consisting of silicotungstic acid, phosphotungstic acid, phosphomolybdic acid and vanadotungstic acid provided on a support.
2. A catalyst as claimed in claim 1 wherein the support is selected from the group consisting of silica gel, alumina, silica-alumina, clays and montmorillonite.
3. A process for the preparation of a catalyst useful for the synthesis of 2-and 4-picolines, the process comprising dissolving a heteropoly acid in distilled water; mixing the resulting mixture with desired amount of a binder to obtain a slurry; stirring the slurry till uniform impregnation is achieved; drying the slurry in air at 200-250°C
for a time period in the range of 0.5 to 1.5 hours; further heating the slurry at a temperature in the range of 300 to 400°C for time period in the range of 0.5 to 1.5 hours and cooling the resultant product to room temperature in a desiccator to get the desired catalyst.
4. A process as claimed in claim 3 wherein the heteropolyacid is selected from the group consisting of silicotungstic acid, phosphotungstic acid, phosphomolybdic acid and vanadotungstic acid.
5. A process as claimed in claim 3 wherein the binder is selected from the group consisting of silica, alumina, silica-alumina, clays and montmorillonite.
6. A process as claimed in claim 3 wherein the heteropoly acid is dissolved in distilled water in a ratio of 0.5:4.5 (w/w).
7. A process as claimed in claim 3 wherein the binder comprises silica gel of mesh size 6-14.
8. A process as claimed in claim 3 wherein the slurry is stirred for a time period in the range of 30-40 minutes.
9. A process for the preparation of 2- and 4- picolines which comprises reacting acetaldehyde and ammonia under heat in the presence of a catalyst comprising a composite of a heteropolyacid impregnated on a support, the catalyst being present in an amount in the range of 5 to 15 wt %, and separating the 2- and 4- picoline formed.
10. A process as claimed in claim 9 wherein the acetaldehyde and ammonia are taken in a ratio of 0.8 to 1.2 (w/w) and are reacted at a temperature in the range of 300 to 500°C.
11. A process as claimed in claim 9 wherein the reaction is carried out in a glass reactor.
12. A process as claimed in claim 9 wherein weight hourly space velocity of the acetaldehyde and ammonia is maintained in the range of 0.1 to 10 g/g of catalyst.
13. A process as claimed in claim 12 wherein the weight hourly space velocity of the acetaldehyde and ammonia is maintained in the range of 1 to 3 g/g of the catalyst.
14. A process as claimed in claim 9 wherein the the 2- and 4-picolines are separated by fractional distillation.
15. A process as claimed in claim 9 wherein the heteropolyacid is selected from the group consisting of silicotungstic acid, phosphotungstic acid, phosphomolybdic acid and vanadotungstic acid.
16. A process as claimed in claim 9 wherein the binder is selected from the group consisting of silica, alumina, silica-alumina, clays and montmorillonite.
17. A process as claimed in claim 9 wherein the binder comprises silica gel of mesh size 6-14.
CA2552158A 2003-12-31 2003-12-31 Catalyst for synthesis of 2- and 4-picolines, process for preparing 2- and 4-picoline and process for preparing the catalyst Expired - Fee Related CA2552158C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IN2003/000467 WO2005063389A1 (en) 2003-12-31 2003-12-31 Catalyst for synthesis of 2-and 4-picolines, process for preparing 2- and 4-picoline and process for preparing the catalyst

Publications (2)

Publication Number Publication Date
CA2552158A1 true CA2552158A1 (en) 2005-07-14
CA2552158C CA2552158C (en) 2010-06-22

Family

ID=34717583

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2552158A Expired - Fee Related CA2552158C (en) 2003-12-31 2003-12-31 Catalyst for synthesis of 2- and 4-picolines, process for preparing 2- and 4-picoline and process for preparing the catalyst

Country Status (5)

Country Link
EP (1) EP1708811A1 (en)
CN (1) CN100448534C (en)
AU (1) AU2003300723B2 (en)
CA (1) CA2552158C (en)
WO (1) WO2005063389A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100446857C (en) * 2006-11-02 2008-12-31 武汉理工大学 Method for preparing heteropoly acid/ordered mesic porous silicon oxide catalyst, and its application
CN107983398B (en) * 2017-10-27 2020-07-17 苏州盖德精细材料有限公司 Production method of nano-attapulgite composite catalyst for preparing 3-methylpyridine
CN110586187B (en) * 2019-10-11 2022-05-13 沧州那瑞化学科技有限公司 Supported phosphotungstic acid catalyst, and preparation method and application thereof

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2463466A (en) * 1948-09-29 1949-03-01 Socony Vacuum Oil Co Inc Production of nitriles
CA1333793C (en) * 1988-09-30 1995-01-03 Gerald L. Goe Pyridine base synthesis process and catalyst for same
GB9419387D0 (en) * 1994-09-26 1994-11-09 Bp Chem Int Ltd Olefin hydration process
CN1093000C (en) * 1996-12-27 2002-10-23 吉林化学工业公司研究院 Catalyst for ether pyrolysis isobutylene and applications
US5856575A (en) * 1997-01-22 1999-01-05 Council Of Scientific Industrial Research Process for the preparation of N-acetyl aminophenols
US5994550A (en) * 1998-12-30 1999-11-30 Mobil Oil Corporation Pyridine/picoline production process

Also Published As

Publication number Publication date
EP1708811A1 (en) 2006-10-11
AU2003300723A1 (en) 2005-07-21
CN100448534C (en) 2009-01-07
WO2005063389A1 (en) 2005-07-14
AU2003300723B2 (en) 2010-01-14
CA2552158C (en) 2010-06-22
CN1886195A (en) 2006-12-27

Similar Documents

Publication Publication Date Title
RU2563649C2 (en) Method of producing zeolite-based catalyst for converting methanol into olefins
Wang et al. Knoevenagel condensation catalyzed by USY zeolite
CA2552158A1 (en) Catalyst for synthesis of 2- and 4-picolines, process for preparing 2- and 4-picoline and process for preparing the catalyst
JPH0625110A (en) Method of synthesizing alkylamine using montmorillonite
CA1230618A (en) Preparation of dienes by dehydration of aldehydes
US5387702A (en) Process for the preparation of cabofuran
JP2872790B2 (en) Method for producing lower fatty acid ester
US8529869B2 (en) Catalysts and method for the hydroamination of olefins
JP2003529577A (en) Process for producing a mixture of methylene dianiline and its higher analog products
JP3132063B2 (en) Process for producing triethylenediamines and piperazines
MXPA98000124A (en) Process for the manufacturing of methylamine
US4395554A (en) Process for producing alpha-picoline
US7514559B2 (en) Catalyst for synthesis of 2- and 4-picolines
JP2002508006A (en) Method for producing methylamine using chabazite catalyst
JPH05301842A (en) Production of lower fatty acid ester
JPH0748319A (en) Production of dialkyl carbonate
JP2850636B2 (en) Method for producing lower fatty acid ester
RU2328343C2 (en) Catalyst for synthesising 2-and 4-picolines, method for producing 2-and 4-picolines and method for producing catalyst
RU2767907C1 (en) Catalyst for alkylation of benzene with propylene to isopropylbenzene and method for producing same
RU2780406C2 (en) Method for production of vinyl-n-butyl ester
US5780686A (en) Process for preparing 4-oxa-amines
NZ548652A (en) Catalyst for synthesis of 2-and 4-picolines, process for preparing 2- and 4-picoline and process for preparing the catalyst
JPH0251412B2 (en)
JPH062230B2 (en) Process for producing N-alkylaniline and catalyst for the process
KR101331456B1 (en) Silica-alumina catalyst treated with fluorine and method for preparing cumene using same

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20181231