CA1063608A - Preparation of pyridines and nicotinonitrile from piperidines - Google Patents
Preparation of pyridines and nicotinonitrile from piperidinesInfo
- Publication number
- CA1063608A CA1063608A CA281,743A CA281743A CA1063608A CA 1063608 A CA1063608 A CA 1063608A CA 281743 A CA281743 A CA 281743A CA 1063608 A CA1063608 A CA 1063608A
- Authority
- CA
- Canada
- Prior art keywords
- vanadia
- piperidine
- supported
- support
- pyridine
- 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
Links
- 150000003053 piperidines Chemical class 0.000 title claims abstract description 13
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 title abstract description 21
- 150000003222 pyridines Chemical class 0.000 title description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 65
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 49
- 239000003054 catalyst Substances 0.000 claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 34
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims abstract description 10
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 claims abstract description 7
- -1 alkyl piperidine Chemical compound 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 17
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 239000011148 porous material Substances 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 230000008929 regeneration Effects 0.000 claims description 6
- 238000011069 regeneration method Methods 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- 229910001882 dioxygen Inorganic materials 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 4
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 claims 2
- 238000005915 ammonolysis reaction Methods 0.000 abstract description 8
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 abstract description 3
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 description 15
- 238000006356 dehydrogenation reaction Methods 0.000 description 14
- 230000000875 corresponding effect Effects 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 230000007246 mechanism Effects 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 3
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- 241000288748 Chrysochloridae Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
- ICBFNPPCXPMCBP-UHFFFAOYSA-N 2,5-dimethylpiperidine Chemical compound CC1CCC(C)NC1 ICBFNPPCXPMCBP-UHFFFAOYSA-N 0.000 description 1
- NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 description 1
- BKOWRYQHXXBRPV-UHFFFAOYSA-N 2-ethylpiperidine Chemical compound [CH2]CC1CCCCN1 BKOWRYQHXXBRPV-UHFFFAOYSA-N 0.000 description 1
- YLUDSYGJHAQGOD-UHFFFAOYSA-N 3-ethylpiperidine Chemical compound CCC1CCCNC1 YLUDSYGJHAQGOD-UHFFFAOYSA-N 0.000 description 1
- KWHPWBXOLZTZMJ-UHFFFAOYSA-N 4-ethylpiperidine Chemical compound CCC1CCNCC1 KWHPWBXOLZTZMJ-UHFFFAOYSA-N 0.000 description 1
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 1
- XOFNHZHCGBPVGJ-UHFFFAOYSA-N 5-ethyl-2-methylpiperidine Chemical compound CCC1CCC(C)NC1 XOFNHZHCGBPVGJ-UHFFFAOYSA-N 0.000 description 1
- 241000731807 Anadia Species 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 241001255830 Thema Species 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
-
- 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
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/20—Vanadium, niobium or tantalum
- B01J23/22—Vanadium
-
- 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
- C07D213/60—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/701,693 US4051140A (en) | 1976-07-01 | 1976-07-01 | Preparation of pyridines and nicotinonitrile from piperidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1063608A true CA1063608A (en) | 1979-10-02 |
Family
ID=24818303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA281,743A Expired CA1063608A (en) | 1976-07-01 | 1977-06-30 | Preparation of pyridines and nicotinonitrile from piperidines |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4051140A (https=) |
| JP (1) | JPS5822114B2 (https=) |
| BE (1) | BE856302A (https=) |
| BR (1) | BR7704282A (https=) |
| CA (1) | CA1063608A (https=) |
| CH (1) | CH631443A5 (https=) |
| DE (1) | DE2729072A1 (https=) |
| FR (1) | FR2356638A1 (https=) |
| GB (1) | GB1583187A (https=) |
| IT (1) | IT1083074B (https=) |
| NL (1) | NL178788C (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3107755A1 (de) * | 1981-02-28 | 1982-09-16 | Degussa Ag, 6000 Frankfurt | Katalysatoren fuer die herstellung von 3-cyanpyridin |
| FR2503156A1 (fr) * | 1981-04-01 | 1982-10-08 | Rhone Poulenc Spec Chim | Procede de preparation de pyridine et de pyridines substituees |
| US4407734A (en) * | 1981-08-10 | 1983-10-04 | W. R. Grace & Co. | Spray dried vanadia catalyst and method of preparing it |
| JPH01288266A (ja) * | 1988-05-17 | 1989-11-20 | Nippon T-Paul:Kk | 殺菌消毒方法 |
| US4935521A (en) * | 1989-04-06 | 1990-06-19 | E. I. Du Pont De Nemours And Company | Preparation of 3-picoline |
| TW577876B (en) * | 1997-01-29 | 2004-03-01 | Reilly Ind Inc | Processes for producing 3-cyanopyridine from 2-methyl-1,5-pentanediamine |
| US6118003A (en) * | 1998-01-29 | 2000-09-12 | Reilly Industries, Inc. | Processes for producing 3-cyanopyridine from 2-methyl-1,5-pentanediamine |
| DE19931115A1 (de) | 1999-07-06 | 2001-01-11 | Bayer Ag | Racemisierung von R, S-Dioxo-Benzylpyrrolopiperidin |
| US8022167B2 (en) * | 2006-12-21 | 2011-09-20 | Aaron Minter | Process for the synthesis of diaminopyridines from glutaronitriles |
| US7999057B2 (en) | 2008-07-08 | 2011-08-16 | E. I. Du Pont De Nemours And Company | Gas-phase process for the synthesis of diaminopyridines from glutaronitriles |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3555021A (en) * | 1967-02-21 | 1971-01-12 | Merck & Co Inc | Process for the preparation of heterocyclic nitriles |
| US3925447A (en) * | 1971-05-26 | 1975-12-09 | Lummus Co | Production of nitriles |
| US3929811A (en) * | 1973-11-15 | 1975-12-30 | Lummus Co | Production of pyridine nitriles and carboxylic acids |
-
1976
- 1976-07-01 US US05/701,693 patent/US4051140A/en not_active Expired - Lifetime
-
1977
- 1977-06-24 JP JP52076053A patent/JPS5822114B2/ja not_active Expired
- 1977-06-27 GB GB26879/77A patent/GB1583187A/en not_active Expired
- 1977-06-28 DE DE19772729072 patent/DE2729072A1/de not_active Withdrawn
- 1977-06-29 FR FR7719937A patent/FR2356638A1/fr active Granted
- 1977-06-29 NL NLAANVRAGE7707230,A patent/NL178788C/xx not_active IP Right Cessation
- 1977-06-30 BE BE178939A patent/BE856302A/xx not_active IP Right Cessation
- 1977-06-30 BR BR7704282A patent/BR7704282A/pt unknown
- 1977-06-30 CH CH807377A patent/CH631443A5/de not_active IP Right Cessation
- 1977-06-30 IT IT68517/77A patent/IT1083074B/it active
- 1977-06-30 CA CA281,743A patent/CA1063608A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7707230A (nl) | 1978-01-03 |
| NL178788B (nl) | 1985-12-16 |
| BE856302A (fr) | 1977-10-17 |
| GB1583187A (en) | 1981-01-21 |
| NL178788C (nl) | 1986-05-16 |
| IT1083074B (it) | 1985-05-21 |
| JPS5822114B2 (ja) | 1983-05-06 |
| CH631443A5 (de) | 1982-08-13 |
| BR7704282A (pt) | 1978-03-28 |
| DE2729072A1 (de) | 1978-01-12 |
| JPS535172A (en) | 1978-01-18 |
| FR2356638A1 (fr) | 1978-01-27 |
| US4051140A (en) | 1977-09-27 |
| FR2356638B1 (https=) | 1982-07-23 |
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