CN104130180A - Method for preparing N-vinyl carbazole - Google Patents
Method for preparing N-vinyl carbazole Download PDFInfo
- Publication number
- CN104130180A CN104130180A CN201410364002.9A CN201410364002A CN104130180A CN 104130180 A CN104130180 A CN 104130180A CN 201410364002 A CN201410364002 A CN 201410364002A CN 104130180 A CN104130180 A CN 104130180A
- Authority
- CN
- China
- Prior art keywords
- vinylcarbazole
- preparing
- carbazole
- reaction
- vinyl carbazole
- 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
- SDFLTYHTFPTIGX-UHFFFAOYSA-N C[n]1c2ccccc2c2c1cccc2 Chemical compound C[n]1c2ccccc2c2c1cccc2 SDFLTYHTFPTIGX-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N c1ccc2[nH]c3ccccc3c2c1 Chemical compound c1ccc2[nH]c3ccccc3c2c1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
Abstract
The invention discloses a method for preparing N-vinyl carbazole. The method comprises the following reactions: carrying out a reaction of carbazole and acetylene to produce N-vinyl carbazole under conditions of taking DMSO as a solvent and adjusting the pH value with KOH, wherein the reaction temperature is 160-170 DEG C. The method has the advantages of simple process, easy operation, low cost, and high product yield.
Description
Technical field
The present invention relates to the synthetic of a kind of organic compound, relate in particular to a kind of method of the N-of preparation vinylcarbazole.
Background technology
The molecular formula of N-vinylcarbazole is C14H11N, and the application of N-vinylcarbazole is for producing the low photographic material of argentiferous, manufactures the record-breaking achievement without silver-colored medium and novel recording system and Novel process of high hypersensitization.
The polymkeric substance of N-vinylcarbazole is the organic materials with photoconductivity, and the xerox light sensitive plate coating with it has good photocopying effect to bluish voilet drawing and the more image of gradation; Comply without darkroom with the holographic photograph and picture of the thermoplastic of its figure system, can original position aobvious clear and reuse; With the illumination radical polymerization sensitive materials of its preparation, its light sensitivity reaches the degree of silver salt material, can carry out high-speed photograph.
The main method complexity of at present synthetic N-vinylcarbazole, cost is high, and yield is low, and product purity is not high simultaneously; Therefore,, for addressing the above problem, spy provides a kind of new technical scheme.
Summary of the invention
The object of this invention is to provide a kind of technique simple, consume low, the N-vinylcarbazole preparation method that yield is high.
The present invention is achieved by the following technical solutions:
Prepare a method for N-vinylcarbazole, by following reaction composition: make solvent with acetylene at DMSO by carbazole, KOH regulates reaction under the condition of pH value to produce N-vinylcarbazole:
Further, temperature of reaction is 160～170 DEG C.
Further, comprise developping agent, PE: EA=10: 1.
Further, the intake of described acetylene be carbazole reaction complete till.
The invention has the beneficial effects as follows: technique is simple, easy to operate, and cost is low, and product yield is high.
Embodiment
Reaction of the present invention is specific as follows:
By following reaction composition: make solvent with acetylene at DMSO by carbazole, KOH regulates reaction under the condition of pH value to produce N-vinylcarbazole:
Embodiment
The carbazole that takes 50g is dissolved in the DMSO of 100ml (dimethyl sulfoxide (DMSO)), and heating makes it to dissolve completely.Solution is poured in the there-necked flask of 500ml, claimed 2g potassium hydroxide to add in solution.Be warmed up to 160 DEG C, start to pass into acetylene, until raw material consumption is complete, (TLC (PE: EA=10: 1)), cooling, DMSO is removed in underpressure distillation, then by 175 DEG C/5mmHg of lobe pump underpressure distillation collection product N-vinylcarbazole.Finally obtain sterling 46.2g (yield 80%).
Claims (4)
1. a method of preparing N-vinylcarbazole, is characterized in that: by following reaction composition: make solvent with acetylene at DMSO by carbazole, KOH regulates reaction under the condition of pH value to produce N-vinylcarbazole:
2. a kind of method of preparing N-vinylcarbazole according to claim 1, is characterized in that: temperature of reaction is 160～170 DEG C.
3. a kind of method of preparing N-vinylcarbazole according to claim 1, is characterized in that: comprise developping agent, PE: EA=10: 1.
4. a kind of method of preparing N-vinylcarbazole according to claim 1, is characterized in that: the intake of described acetylene be carbazole reaction complete till.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410364002.9A CN104130180A (en) | 2014-07-25 | 2014-07-25 | Method for preparing N-vinyl carbazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410364002.9A CN104130180A (en) | 2014-07-25 | 2014-07-25 | Method for preparing N-vinyl carbazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104130180A true CN104130180A (en) | 2014-11-05 |
Family
ID=51803077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410364002.9A Pending CN104130180A (en) | 2014-07-25 | 2014-07-25 | Method for preparing N-vinyl carbazole |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104130180A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107488140A (en) * | 2017-10-10 | 2017-12-19 | 厦门大学 | A kind of synthetic method of N ethyl carbazoles |
| CN108794381A (en) * | 2018-05-08 | 2018-11-13 | 中国科学院青岛生物能源与过程研究所 | A method of preparing N- vinyl carbazoles |
| CN110386895A (en) * | 2019-07-19 | 2019-10-29 | 河南省科学院化学研究所有限公司 | A method of synthesis N- vinyl carbazole |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2426465A (en) * | 1945-11-27 | 1947-08-26 | Gen Electric | Method of preparing n-vinyl carbazole |
| US3479392A (en) * | 1960-12-23 | 1969-11-18 | Grace W R & Co | Production of unsaturated ethers and esters |
| GB1275415A (en) * | 1968-12-16 | 1972-05-24 | British Oxygen Co Ltd | Preparation of n-vinyl carbazole |
| US3679700A (en) * | 1970-05-13 | 1972-07-25 | Borden Inc | Preparation of n-vinyl carbazole |
| CN103570606A (en) * | 2012-07-23 | 2014-02-12 | 上海永鸿实业集团化学科技有限公司 | Method for preparing carbazole and vinyl carbazole |
-
2014
- 2014-07-25 CN CN201410364002.9A patent/CN104130180A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2426465A (en) * | 1945-11-27 | 1947-08-26 | Gen Electric | Method of preparing n-vinyl carbazole |
| US3479392A (en) * | 1960-12-23 | 1969-11-18 | Grace W R & Co | Production of unsaturated ethers and esters |
| GB1275415A (en) * | 1968-12-16 | 1972-05-24 | British Oxygen Co Ltd | Preparation of n-vinyl carbazole |
| US3679700A (en) * | 1970-05-13 | 1972-07-25 | Borden Inc | Preparation of n-vinyl carbazole |
| CN103570606A (en) * | 2012-07-23 | 2014-02-12 | 上海永鸿实业集团化学科技有限公司 | Method for preparing carbazole and vinyl carbazole |
Non-Patent Citations (3)
| Title |
|---|
| 丁博，等: "9-乙烯基咔唑合成研究", 《化学工程与装备》, no. 2, 28 February 2013 (2013-02-28), pages 5 - 7 * |
| 张文龙，等: "用咔唑单体合成乙烯咔唑工艺的研究", 《塑料助剂》, no. 2, 31 December 2011 (2011-12-31), pages 26 - 29 * |
| 熊裕堂: "常压乙烯化法合成单体N-乙烯咔唑的研究", 《精细化工》, vol. 11, no. 3, 31 December 1994 (1994-12-31) * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107488140A (en) * | 2017-10-10 | 2017-12-19 | 厦门大学 | A kind of synthetic method of N ethyl carbazoles |
| CN108794381A (en) * | 2018-05-08 | 2018-11-13 | 中国科学院青岛生物能源与过程研究所 | A method of preparing N- vinyl carbazoles |
| CN110386895A (en) * | 2019-07-19 | 2019-10-29 | 河南省科学院化学研究所有限公司 | A method of synthesis N- vinyl carbazole |
| CN110386895B (en) * | 2019-07-19 | 2022-11-01 | 河南省科学院化学研究所有限公司 | Method for synthesizing N-vinyl carbazole |
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Legal Events
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|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20141105 |