GB717799A - Production of n-vinyl ª-pyrrolidone - Google Patents
Production of n-vinyl ª-pyrrolidoneInfo
- Publication number
- GB717799A GB717799A GB21139/52A GB2113952A GB717799A GB 717799 A GB717799 A GB 717799A GB 21139/52 A GB21139/52 A GB 21139/52A GB 2113952 A GB2113952 A GB 2113952A GB 717799 A GB717799 A GB 717799A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrrolidone
- hydroxyethyl
- vinyl
- activated alumina
- water
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
Abstract
A process for the production of N-vinyl a -pyrrolidone comprises subjecting N-b -hydroxyethyl a -pyrrolidone to dehydration. N-b -Hydroxyethyl-a -pyrrolidone is obtained by reacting ethanolamine with g -butyrolactone, with distillation of water from the reaction mixture, suitably at 200 DEG to 250 DEG C., the initial product being N-b -hydroxyethyl-g -hydroxybutyramide. The dehydration, which is preferably carried out in the presence of a dehydrating catalyst, may be carried out in the liquid or vapour phase. In the liquid phase the N-b -hydroxyethyl a -pyrrolidone may be passed downward through a chamber filled with particles of the catalyst heated to 200 DEG to 400 DEG C., preferably 320 DEG to 350 DEG C. Alternatively the N-b -hydroxyethyl a -pyrrolidone may be added to a liquid such as mineral oil, diphenyl or diphenyl oxide which contains suspended finely divided catalyst and is maintained at reaction temperature; the water and N-vinyl a -pyrrolidone are preferably distilled off at 150 to 300 mm. and the process may be operated continuously. Vapour phase dehydration is preferably effected at 250 DEG to 350 DEG C. and at pressures below 100 mm. Basic or neutral catalysts are suitable. Specified are calcium oxide, aluminium oxide, and a mixture of aluminium oxide, iron oxide and potassium hydroxide. Hourly space velocities of 500 to 4000, preferably 2600, in the vapour phase process and of 150 to 300 in the first-mentioned liquid phase process are suitable. In examples N-vinyl-a -pyrrolidone is prepared by (1) passing N-b -hydroxyethyl a -pyrrolidone (the product obtained from the reaction of ethanolamine and g -butyolactone at 200 DEG to 250 DEG C. with distillation of water) downwards over activated alumina particles heated to 270 DEG to 290 DEG C.; (2) passing N-b -hydroxyethyl a -pyrrolidone vapour over activated alumina at 300 DEG to 340 DEG C.; (3) gradually adding N-b -hydroxyethyl a -pyrrolidone to activated alumina particles suspended in white mineral oil heated to 320 DEG to 350 DEG C., with condensation of the evolved vapours; (4) heating ethanolamine and g -butyrolactone at 200 DEG to 250 DEG C. with distillation of water from the mixture, and passing the vaporized residue over activated alumina at 290 DEG to 335 DEG C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US717799XA | 1951-08-24 | 1951-08-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB717799A true GB717799A (en) | 1954-11-03 |
Family
ID=22103537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21139/52A Expired GB717799A (en) | 1951-08-24 | 1952-08-22 | Production of n-vinyl ª-pyrrolidone |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB717799A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1094061A1 (en) * | 1999-10-22 | 2001-04-25 | Nippon Shokubai Co., Ltd. | Process for recovering N-Vinyl-2-Pyrrolidone |
| US7037412B2 (en) * | 2002-02-20 | 2006-05-02 | Nippon Shokubai Co., Ltd. | Method for preparing deodorized N-vinyl-2-pyrrolidone |
-
1952
- 1952-08-22 GB GB21139/52A patent/GB717799A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1094061A1 (en) * | 1999-10-22 | 2001-04-25 | Nippon Shokubai Co., Ltd. | Process for recovering N-Vinyl-2-Pyrrolidone |
| US6436243B1 (en) | 1999-10-22 | 2002-08-20 | Nippon Shokubai Co Ltd | Process for recovering N-vinyl-2-pyrrolidone |
| KR100591046B1 (en) * | 1999-10-22 | 2006-06-19 | 가부시키가이샤 닛폰 쇼쿠바이 | Process for recovering n-vinyl-2-pyrrolidone |
| US7037412B2 (en) * | 2002-02-20 | 2006-05-02 | Nippon Shokubai Co., Ltd. | Method for preparing deodorized N-vinyl-2-pyrrolidone |
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