DE2729009A1 - Verfahren zur herstellung von cyanopyridinen aus piperidinen - Google Patents
Verfahren zur herstellung von cyanopyridinen aus piperidinenInfo
- Publication number
- DE2729009A1 DE2729009A1 DE19772729009 DE2729009A DE2729009A1 DE 2729009 A1 DE2729009 A1 DE 2729009A1 DE 19772729009 DE19772729009 DE 19772729009 DE 2729009 A DE2729009 A DE 2729009A DE 2729009 A1 DE2729009 A1 DE 2729009A1
- Authority
- DE
- Germany
- Prior art keywords
- vanadium compound
- alkylpiperidine
- carrier
- reactor
- oxidized
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000003053 piperidines Chemical class 0.000 title description 7
- 150000003682 vanadium compounds Chemical class 0.000 claims description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 5
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 claims description 5
- 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
- 239000011148 porous material Substances 0.000 claims description 5
- HHUIAYDQMNHELC-UHFFFAOYSA-N [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O HHUIAYDQMNHELC-UHFFFAOYSA-N 0.000 claims description 4
- DRLFSUDDXLQHJT-UHFFFAOYSA-N 2,3-dimethylpiperidine Chemical compound CC1CCCNC1C DRLFSUDDXLQHJT-UHFFFAOYSA-N 0.000 claims description 2
- ICBFNPPCXPMCBP-UHFFFAOYSA-N 2,5-dimethylpiperidine Chemical compound CC1CCC(C)NC1 ICBFNPPCXPMCBP-UHFFFAOYSA-N 0.000 claims description 2
- YLUDSYGJHAQGOD-UHFFFAOYSA-N 3-ethylpiperidine Chemical compound CCC1CCCNC1 YLUDSYGJHAQGOD-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 239000004411 aluminium Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-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
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- QOZOFODNIBQPGN-UHFFFAOYSA-N 2,4-dimethylpiperidine Chemical compound CC1CCNC(C)C1 QOZOFODNIBQPGN-UHFFFAOYSA-N 0.000 description 1
- NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-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
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 239000007806 chemical reaction intermediate 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
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000005078 molybdenum compound Substances 0.000 description 1
- 150000002752 molybdenum compounds Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000003039 volatile agent Substances 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
- C07D213/60—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
-
- 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
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/613—10-100 m2/g
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/63—Pore volume
- B01J35/633—Pore volume less than 0.5 ml/g
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/701,694 US4057552A (en) | 1976-07-01 | 1976-07-01 | Production of cyanopyridines from piperidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2729009A1 true DE2729009A1 (de) | 1978-01-12 |
Family
ID=24818308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772729009 Withdrawn DE2729009A1 (de) | 1976-07-01 | 1977-06-28 | Verfahren zur herstellung von cyanopyridinen aus piperidinen |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4057552A (enExample) |
| JP (1) | JPS5822115B2 (enExample) |
| BE (1) | BE856303A (enExample) |
| BR (1) | BR7704283A (enExample) |
| CA (1) | CA1063609A (enExample) |
| CH (1) | CH634054A5 (enExample) |
| DE (1) | DE2729009A1 (enExample) |
| FR (1) | FR2356639A1 (enExample) |
| GB (1) | GB1573683A (enExample) |
| IT (1) | IT1083075B (enExample) |
| NL (1) | NL179054C (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4721789A (en) * | 1984-12-05 | 1988-01-26 | The Standard Oil Company | Oxidative cyclization of 2-methylglutaronitrile to 3-cyanopyridine |
| JP2615819B2 (ja) * | 1988-04-28 | 1997-06-04 | 三菱瓦斯化学株式会社 | シアノピリジンの製造法 |
| TW577876B (en) * | 1997-01-29 | 2004-03-01 | Reilly Ind Inc | Processes for producing 3-cyanopyridine from 2-methyl-1,5-pentanediamine |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2592123A (en) * | 1948-09-28 | 1952-04-08 | Socony Vacuum Oil Co Inc | Production of pyridine nitriles |
| US3555021A (en) * | 1967-02-21 | 1971-01-12 | Merck & Co Inc | Process for the preparation of heterocyclic nitriles |
| US3544617A (en) * | 1967-12-27 | 1970-12-01 | Showa Denko Kk | Process for the manufacture of aromatic 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 US05/701,694 patent/US4057552A/en not_active Expired - Lifetime
-
1977
- 1977-06-27 GB GB26880/77A patent/GB1573683A/en not_active Expired
- 1977-06-28 JP JP52077723A patent/JPS5822115B2/ja not_active Expired
- 1977-06-28 DE DE19772729009 patent/DE2729009A1/de not_active Withdrawn
- 1977-06-29 FR FR7719938A patent/FR2356639A1/fr active Granted
- 1977-06-29 NL NLAANVRAGE7707231,A patent/NL179054C/xx not_active IP Right Cessation
- 1977-06-30 BE BE178940A patent/BE856303A/xx not_active IP Right Cessation
- 1977-06-30 BR BR7704283A patent/BR7704283A/pt unknown
- 1977-06-30 CH CH807277A patent/CH634054A5/de not_active IP Right Cessation
- 1977-06-30 CA CA281,848A patent/CA1063609A/en not_active Expired
- 1977-06-30 IT IT68518/77A patent/IT1083075B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| NL179054C (nl) | 1986-07-01 |
| GB1573683A (en) | 1980-08-28 |
| IT1083075B (it) | 1985-05-21 |
| BE856303A (fr) | 1977-10-17 |
| BR7704283A (pt) | 1978-03-28 |
| US4057552A (en) | 1977-11-08 |
| NL7707231A (nl) | 1978-01-03 |
| CA1063609A (en) | 1979-10-02 |
| FR2356639A1 (fr) | 1978-01-27 |
| CH634054A5 (de) | 1983-01-14 |
| JPS5822115B2 (ja) | 1983-05-06 |
| JPS535173A (en) | 1978-01-18 |
| FR2356639B1 (enExample) | 1982-09-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8127 | New person/name/address of the applicant |
Owner name: THE LUMMUS CO., 07003 BLOOMFIELD, N.J., US |
|
| 8139 | Disposal/non-payment of the annual fee |