GB966264A - Production of alkyl pyridines - Google Patents
Production of alkyl pyridinesInfo
- Publication number
- GB966264A GB966264A GB3129861A GB3129861A GB966264A GB 966264 A GB966264 A GB 966264A GB 3129861 A GB3129861 A GB 3129861A GB 3129861 A GB3129861 A GB 3129861A GB 966264 A GB966264 A GB 966264A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyridine
- ethyl
- mixture
- ketone
- alumina
- 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
- -1 alkyl pyridines Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- GFYHSKONPJXCDE-UHFFFAOYSA-N 2,3,5-trimethylpyridine Chemical compound CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 abstract 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 239000000377 silicon dioxide Substances 0.000 abstract 2
- COHDGTRFTKHYSJ-UHFFFAOYSA-N 2-Ethyl-5-methylpyridine Chemical compound CCC1=CC=C(C)C=N1 COHDGTRFTKHYSJ-UHFFFAOYSA-N 0.000 abstract 1
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 abstract 1
- SAVPSRHNNQVBLW-UHFFFAOYSA-N 3,5-diethylpyridine Chemical compound CCC1=CN=CC(CC)=C1 SAVPSRHNNQVBLW-UHFFFAOYSA-N 0.000 abstract 1
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical group CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 abstract 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 abstract 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 229910052793 cadmium Inorganic materials 0.000 abstract 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 abstract 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 abstract 1
- 229910052804 chromium Inorganic materials 0.000 abstract 1
- 239000011651 chromium Substances 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 abstract 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000011133 lead Substances 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 229910052750 molybdenum Inorganic materials 0.000 abstract 1
- 239000011733 molybdenum Substances 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229910052709 silver Inorganic materials 0.000 abstract 1
- 239000004332 silver Substances 0.000 abstract 1
- ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 abstract 1
- 239000011135 tin Substances 0.000 abstract 1
- 229910052718 tin Inorganic materials 0.000 abstract 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052721 tungsten Inorganic materials 0.000 abstract 1
- 239000010937 tungsten Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
Landscapes
- Pyridine Compounds (AREA)
Abstract
Alkyl pyridines are prepared by heating together in the vapour phase, a mixture of formaldehyde, ammonia, an aliphatic ketone with two methylene groups adjacent to the carbonyl carbon atom, and a saturated aliphatic aldehyde with two or more carbon atoms in the molecule. The mixture may be heated at from 300-500 DEG C. and a condensation catalyst, e.g. silica, alumina or a mixture of silica and alumina, optionally with titania, zirconia, ceria or thoria, or compounds of zinc, cadmium, tin, lead, tungsten, nickel, cobalt, chromium, molybdenum, iron, palladium or silver. The aldehyde may be acetaldehyde, propionaldehyde and n-butyraldehyde, and the ketones, acetone, methylethyl ketone and diethyl ketone. Examples describe the production of pyridine bases comprising, 5-ethyl-2-methyl and 2-ethyl-5-methyl pyridine, 3,5-diethyl pyridine, 2,3,5-trimethyl pyridine, 2:5-, 3:5-, 2:6- and 2:4-butidine, a - and g -picoline, pyridine, 2-ethyl pyridine, and 2:4:6-collidine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3129861A GB966264A (en) | 1961-08-31 | 1961-08-31 | Production of alkyl pyridines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3129861A GB966264A (en) | 1961-08-31 | 1961-08-31 | Production of alkyl pyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB966264A true GB966264A (en) | 1964-08-06 |
Family
ID=10321056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3129861A Expired GB966264A (en) | 1961-08-31 | 1961-08-31 | Production of alkyl pyridines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB966264A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0371615A1 (en) * | 1988-10-28 | 1990-06-06 | Nepera, Inc. | High yield synthesis of pyridine and/or alkylpyridine(s) via condensation of ternary mixtures of aldehydes and/or ketones with ammonia |
| US5013843A (en) * | 1990-06-07 | 1991-05-07 | Nepera, Inc. | High yield of pyridine and/or alkylpyridine(s) in condensation reaction of ternary aldehydes and/or ketones with ammonia |
| US6770643B2 (en) | 1999-12-24 | 2004-08-03 | Aventis Pharma Limited | Azaindoles |
| US6897207B2 (en) | 2001-06-21 | 2005-05-24 | Aventis Pharmaceuticals Inc. | Azaindoles |
-
1961
- 1961-08-31 GB GB3129861A patent/GB966264A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0371615A1 (en) * | 1988-10-28 | 1990-06-06 | Nepera, Inc. | High yield synthesis of pyridine and/or alkylpyridine(s) via condensation of ternary mixtures of aldehydes and/or ketones with ammonia |
| US5013843A (en) * | 1990-06-07 | 1991-05-07 | Nepera, Inc. | High yield of pyridine and/or alkylpyridine(s) in condensation reaction of ternary aldehydes and/or ketones with ammonia |
| US6770643B2 (en) | 1999-12-24 | 2004-08-03 | Aventis Pharma Limited | Azaindoles |
| US7227020B2 (en) | 1999-12-24 | 2007-06-05 | Aventis Pharma Limited | Azaindoles |
| US6897207B2 (en) | 2001-06-21 | 2005-05-24 | Aventis Pharmaceuticals Inc. | Azaindoles |
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