GB534494A - Improvements in or relating to the manufacture of heterocyclic bases - Google Patents
Improvements in or relating to the manufacture of heterocyclic basesInfo
- Publication number
- GB534494A GB534494A GB2735539A GB2735539A GB534494A GB 534494 A GB534494 A GB 534494A GB 2735539 A GB2735539 A GB 2735539A GB 2735539 A GB2735539 A GB 2735539A GB 534494 A GB534494 A GB 534494A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reaction
- reactants
- reaction zone
- heterocyclic bases
- paraldehyde
- 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
- 125000000623 heterocyclic group Chemical group 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 3
- 239000000376 reactant Substances 0.000 abstract 3
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- -1 aliphatic aldehydes Chemical class 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 abstract 2
- 229960003868 paraldehyde Drugs 0.000 abstract 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000005642 Oleic acid Substances 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
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 238000010924 continuous production Methods 0.000 abstract 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 abstract 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
534,494. Heterocyclic bases. DISTILLERS CO., Ltd., STANLEY, H. M., and YOUELL, J. E. Oct. 6, 1939, No. 27355. [Class 2 (iii)] A process for the continuous production of heterocyclic bases containing nitrogen in the ring consists in reacting in the liquid phase, at temperatures between 180‹ and 250‹C., aliphatic aldehydes and ammonia or aliphatic amines, which are mixed together in or near to the reaction zone, whereby long contact between the reactants while their temperature is below reaction temperature is avoided. The reactants are preferably supplied to the reaction zone in the form of pre-heated liquid streams which are mixed together in or near the reaction zone, and the reaction is carried out in a pressure coil immersed in a liquid bath maintained at the reaction temperature. A small quantity of an emulsifying agent, e.g. oleic acid, is preferably added to one of the reactants. Suitable aldehydes for the reaction are acetaldehyde, crotonaldehyde, butyraldehyde and simple polymers of these, e.g. paraldehyde. Methylamine is specified as an amine. In examples, pyridine bases(chiefly 2-methyl-5-ethylpyridine) are obtained by reacting paraldehyde with aqueous ammonia. Specifications 146,869, 147,000, 147,101, 332,623 and 334,193, [all in Class 2 (iii)], are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2735539A GB534494A (en) | 1939-10-06 | 1939-10-06 | Improvements in or relating to the manufacture of heterocyclic bases |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2735539A GB534494A (en) | 1939-10-06 | 1939-10-06 | Improvements in or relating to the manufacture of heterocyclic bases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB534494A true GB534494A (en) | 1941-03-07 |
Family
ID=10258257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2735539A Expired GB534494A (en) | 1939-10-06 | 1939-10-06 | Improvements in or relating to the manufacture of heterocyclic bases |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB534494A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2523580A (en) * | 1944-12-11 | 1950-09-26 | Phillips Petroleum Co | Production of alkyl pyridines |
| US2605264A (en) * | 1944-02-25 | 1952-07-29 | Shell Dev | Process for the production of pyridines |
| DE897408C (en) * | 1950-11-12 | 1953-11-19 | Degussa | Process for the production of tanning agents from ª ‡, ª ‰ -unsaturated aldehydes and nitrogen compounds |
| US2700042A (en) * | 1952-08-30 | 1955-01-18 | Robert S Aries | Production of pyridine and beta picoline |
| US2717897A (en) * | 1951-03-28 | 1955-09-13 | Union Carbide & Carbon Corp | Process for making substituted pyridines |
| US2766287A (en) * | 1949-10-31 | 1956-10-09 | Ruhrchemie Ag | Production of nitrogenous aldehyde condensation products |
| US2844583A (en) * | 1952-10-20 | 1958-07-22 | Celanese Corp | Production of 2-methyl-5-ethylpyridine |
| US2934537A (en) * | 1954-02-12 | 1960-04-26 | Francis E Cislak | Process of preparing pyridine and 3-picoline |
| US4337342A (en) * | 1980-05-23 | 1982-06-29 | Lonza Ltd. | Process for the preparation of 3-picoline |
-
1939
- 1939-10-06 GB GB2735539A patent/GB534494A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2605264A (en) * | 1944-02-25 | 1952-07-29 | Shell Dev | Process for the production of pyridines |
| US2523580A (en) * | 1944-12-11 | 1950-09-26 | Phillips Petroleum Co | Production of alkyl pyridines |
| US2766287A (en) * | 1949-10-31 | 1956-10-09 | Ruhrchemie Ag | Production of nitrogenous aldehyde condensation products |
| DE897408C (en) * | 1950-11-12 | 1953-11-19 | Degussa | Process for the production of tanning agents from ª ‡, ª ‰ -unsaturated aldehydes and nitrogen compounds |
| US2717897A (en) * | 1951-03-28 | 1955-09-13 | Union Carbide & Carbon Corp | Process for making substituted pyridines |
| US2700042A (en) * | 1952-08-30 | 1955-01-18 | Robert S Aries | Production of pyridine and beta picoline |
| US2844583A (en) * | 1952-10-20 | 1958-07-22 | Celanese Corp | Production of 2-methyl-5-ethylpyridine |
| US2934537A (en) * | 1954-02-12 | 1960-04-26 | Francis E Cislak | Process of preparing pyridine and 3-picoline |
| US4337342A (en) * | 1980-05-23 | 1982-06-29 | Lonza Ltd. | Process for the preparation of 3-picoline |
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