DE1470067A1 - Verfahren zur Herstellung von Alkylpyridinbasen - Google Patents
Verfahren zur Herstellung von AlkylpyridinbasenInfo
- Publication number
- DE1470067A1 DE1470067A1 DE19641470067 DE1470067A DE1470067A1 DE 1470067 A1 DE1470067 A1 DE 1470067A1 DE 19641470067 DE19641470067 DE 19641470067 DE 1470067 A DE1470067 A DE 1470067A DE 1470067 A1 DE1470067 A1 DE 1470067A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- activated
- picoline
- alpha
- acetaldehyde
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title description 6
- -1 alkyl pyridine Chemical compound 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims description 37
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 239000011777 magnesium Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- 239000012808 vapor phase Substances 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 3
- VIJYFGMFEVJQHU-UHFFFAOYSA-N aluminum oxosilicon(2+) oxygen(2-) Chemical compound [O-2].[Al+3].[Si+2]=O VIJYFGMFEVJQHU-UHFFFAOYSA-N 0.000 claims description 2
- 159000000003 magnesium salts Chemical class 0.000 claims description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 27
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000003213 activating effect Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 4
- 229910052814 silicon oxide Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- GLPMHULIKFGNIJ-UHFFFAOYSA-N cadmium(2+);dioxido(dioxo)chromium Chemical compound [Cd+2].[O-][Cr]([O-])(=O)=O GLPMHULIKFGNIJ-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- DNNLEMIRRGUGOZ-UHFFFAOYSA-N oxygen(2-);thorium(4+) Chemical class [O-2].[O-2].[Th+4] DNNLEMIRRGUGOZ-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910003452 thorium oxide Inorganic materials 0.000 description 1
- VGBPIHVLVSGJGR-UHFFFAOYSA-N thorium(4+);tetranitrate Chemical compound [Th+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VGBPIHVLVSGJGR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C07D213/06—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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/12—Silica and alumina
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1178663 | 1963-06-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1470067A1 true DE1470067A1 (de) | 1972-03-30 |
Family
ID=11137836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641470067 Pending DE1470067A1 (de) | 1963-06-06 | 1964-05-26 | Verfahren zur Herstellung von Alkylpyridinbasen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE648910A (enrdf_load_stackoverflow) |
| DE (1) | DE1470067A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1396796A (enrdf_load_stackoverflow) |
| GB (1) | GB1042268A (enrdf_load_stackoverflow) |
| NL (1) | NL6405359A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2703070A1 (de) * | 1977-01-26 | 1978-07-27 | Degussa | Verfahren zur herstellung von 3-methylpyridin |
| DE2703049C2 (de) * | 1977-01-26 | 1987-04-16 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Pyridin und 3-Methylpyridin |
| DE2703069A1 (de) * | 1977-01-26 | 1978-07-27 | Degussa | Verfahren zur herstellung von 2-methylpyridin und 3-methylpyridin |
-
1964
- 1964-05-14 NL NL6405359A patent/NL6405359A/xx unknown
- 1964-05-26 GB GB21710/64A patent/GB1042268A/en not_active Expired
- 1964-05-26 DE DE19641470067 patent/DE1470067A1/de active Pending
- 1964-05-28 FR FR976190A patent/FR1396796A/fr not_active Expired
- 1964-06-05 BE BE648910D patent/BE648910A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6405359A (enrdf_load_stackoverflow) | 1964-12-07 |
| FR1396796A (fr) | 1965-04-23 |
| BE648910A (enrdf_load_stackoverflow) | 1964-12-07 |
| GB1042268A (en) | 1966-09-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2427191C3 (de) | Katalysator und Verfahren zur Herstellung aromatischer Nitrile | |
| DE1470067A1 (de) | Verfahren zur Herstellung von Alkylpyridinbasen | |
| DE975008C (de) | Verfahren zur Herstellung von Phosphatueberzuegen auf Zink und dessen Legierungen | |
| DE68924852T2 (de) | Verfahren zur herstellung von pyridinbasen und katalysator zur durchführung des verfahrens. | |
| DE60015313T2 (de) | Verfahren zur oxidierung von benzol und/oder toluol zu phenol und/oder cresol | |
| DE2713316A1 (de) | Verfahren zur herstellung reinweisser 2-chlornikotinsaeure | |
| DE3504732A1 (de) | Verfahren zur herstellung eines gemisches von phosphornitridchlorid-oligomeren | |
| DE2203384B2 (de) | Kontinuierliches Verfahren zur Herstellung von Pyridin und beta-Picolin | |
| DE3879789T2 (de) | Verfahren zur Herstellung von 2,6-Dichlorpyridin. | |
| DE3222780C2 (enrdf_load_stackoverflow) | ||
| DE851185C (de) | Verfahren zur Herstellung ungesaettigter Nitrile | |
| DE1067435B (de) | Verfahren zur Herstellung von Cyanpyridinen | |
| DE613402C (de) | Verfahren zur Darstellung von 4-Pyridylpyridiniumdichlorid | |
| DE2122299A1 (de) | Verfahren zur Herstellung von wasserfreiem Chromsesquioxid durch Reduktion einer sechswertigen Chromverbindung | |
| DE2054773A1 (de) | Verfahren zur Herstellung von Pjridin und Alkylpyndinen aus Aldehyden und Ammoniak | |
| DE890046C (de) | Verfahren zur Herstellung tertiaerer Amine, die einen Thiophenrest enthalten | |
| DE2160673C3 (de) | Verfahren zur Herstellung von 4-Cyanoimidazol-5-carboxyamid bzw. S-Cyanoimidazol-4-carboxyamid | |
| DE1445974C (de) | Verfahren zur Herstellung von Pyridin | |
| DE1255661B (de) | Kontinuierliches Verfahren zur Herstellung von Pyridin und 3-Picolin | |
| DE1445918C (de) | Verfahren zur Herstellung von gegebenenfalls durch eine oder mehrere niedermolekulare Alkylgruppen substituierten Bipyridylen | |
| DE2411057C3 (de) | Oxydationskatalysator und Verfahren zu seiner Herstellung | |
| AT216507B (de) | Verfahren zur Dehydrierung von Alkylpyridinen zu Alkenylpyridinen | |
| DE1770841A1 (de) | Verfahren zur Herstellung von Cyanpyridinen | |
| DE1951587C (enrdf_load_stackoverflow) | ||
| DE890797C (de) | Verfahren zur Herstellung heterocyclische^ ein einziges Stickstoffatom 'im Ring enthaltender Sechsringvenbindungen |