CN110386895B - Method for synthesizing N-vinyl carbazole - Google Patents
Method for synthesizing N-vinyl carbazole Download PDFInfo
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- CN110386895B CN110386895B CN201910652859.3A CN201910652859A CN110386895B CN 110386895 B CN110386895 B CN 110386895B CN 201910652859 A CN201910652859 A CN 201910652859A CN 110386895 B CN110386895 B CN 110386895B
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- Prior art keywords
- carbazole
- synthesizing
- vinyl carbazole
- vinylcarbazole
- methylbutynol
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The invention provides a new method for synthesizing N-vinyl carbazole, belonging to the field of organic synthesis. The method comprises the following steps: under the alkaline condition of KOH, carbazole reacts with methylbutynol in an ethanol solvent to generate N-vinyl carbazole, and the reaction temperature is 75-80 ℃. The method has the advantages of mild conditions, simple and safe operation, low cost, high yield and the like.
Description
Technical Field
The invention relates to a method for synthesizing N-vinyl carbazole, belonging to the field of organic synthesis.
Background
N-vinyl carbazole is an important nitrogen-containing aromatic heterocyclic compound, has special photoelectric characteristics, accords with the performance of organic photoelectric functional materials, has a strong intramolecular electron transfer function, has good thermal stability, is an important intermediate for synthesizing photoelectric materials, and is widely used for liquid crystal display materials.
At present, N-vinyl carbazole is applied to the synthesis of polyvinyl carbazole (PVK), the PVK is a classic and important polymer which takes hole conduction as a main component, and an electrostatic copying light-sensitive plate coated by the PVK has a good copying effect on bluish purple drawings and images with more gradation of color tones; the thermoplastic holographic photographic picture coated by the resin can be developed in situ and reused without dark room operation; the light sensitivity of the prepared light irradiation free radical polymerization photosensitive material reaches the effect of a silver salt material, and rapid photography can be carried out.
PVK can also be used as high-temp. resistant electric insulating material, and can be made into high-frequency insulating material by means of compression moulding, and also can be made into film, and can be used for replacing mica.
It can be seen that the demand for N-vinylcarbazole is greater in the market. Currently, there are many methods for synthesizing N-vinylcarbazole, and these methods can be roughly classified into five types: (1) Carbazole and acetylene react directly to produce N-vinylcarbazole. (2) Carbazole potassium salt and vinyl chloride react at high temperature to directly obtain N-vinyl carbazole. (3) Carbazole and ethylene oxide react under alkaline conditions to generate N- (beta-hydroxyethyl) carbazole, and the N- (beta-hydroxyethyl) carbazole reacts in a potassium hydroxide ethanol solution to obtain N-vinyl carbazole. (4) Carbazole and 1, 2-dichloroethane firstly generate N- (beta-chloroethyl) carbazole under an alkaline condition, and then dehydrochlorination is carried out under the alkaline condition to obtain N-vinylcarbazole. (5) Carbazole and trimethylsilylacetylene react under alkaline conditions to produce N-vinylcarbazole. Among the above methods, the main reaction substrates of the methods (1), (2) and (3) are gases, high temperature and high pressure are required, the risk coefficient is increased, the requirement on equipment is high, the cost is increased, and the method (3) has long steps and low yield; the method (4) has the advantages that the reaction is carried out step by step, the experimental difficulty is increased, the yield is influenced, and meanwhile, the product purity is not high; the trimethylsilylacetylene used as the raw material in the method (5) is expensive and too high in cost, and is not suitable for industrial production.
Therefore, in order to overcome the disadvantages of the above-mentioned synthesis methods, improvements in the synthesis methods of N-vinylcarbazole are required.
Disclosure of Invention
The invention aims to provide a novel process for synthesizing N-vinylcarbazole, which can be used for safely and safely synthesizing N-vinylcarbazole under mild conditions at low cost with high yield.
To achieve the purpose of the invention, the method comprises the following steps: reacting carbazole and methylbutynol in an ethanol solvent under the alkaline condition of KOH to generate N-vinyl carbazole:
the molar ratio of carbazole to methylbutynol is preferably 1.
The reaction temperature of the process is preferably 75 to 80 ℃.
The invention has the advantages that:
the method for synthesizing the N-vinyl carbazole by taking the methylbutinol as a reaction substrate for the first time has the advantages of mild reaction conditions, simple and safe operation, low methylbutinol cost and high yield, and is suitable for industrial production.
Detailed Description
The present invention will be described in further detail with reference to specific examples
Example 1
Adding 300ml of ethanol solvent into a 500ml reaction bottle, then sequentially adding 83g of carbazole, 30g of potassium hydroxide and 46g of methylbutynol under stirring, gradually heating to 75 ℃, detecting the reaction process by using a gas phase, stopping the reaction when the gas phase peak of the carbazole serving as a raw material completely disappears, distilling under reduced pressure to remove most of the solvent, and then carrying out suction filtration and washing to obtain 88g of a solid crude product (the yield is 91%).
The solid crude product is completely dissolved in a proper amount of ethanol which is heated to reflux, then the mixture is stood to room temperature, white crystals are separated out, the mixture is filtered and dried at room temperature, and 78g of white crystals are obtained (yield is 81%).
Example 2
Adding 1.2L of ethanol solvent into a 2L reaction bottle, then sequentially adding 334g of carbazole, 120g of potassium hydroxide and 185g of methylbutynol while stirring, gradually heating to 80 ℃, detecting the reaction process by using a gas phase, stopping the reaction when the gas phase peak of the raw material carbazole is completely disappeared, carrying out reduced pressure distillation to remove most of the solvent, and then carrying out suction filtration and washing to obtain 348g of a solid crude product (yield is 90%).
The crude solid product is completely dissolved in a proper amount of ethanol heated to reflux, then the mixture is stood to room temperature, white crystals are separated out, the mixture is filtered and dried at room temperature, and 309g of white crystals are obtained (the yield is 80%).
Claims (3)
1. The method for synthesizing the N-vinyl carbazole is characterized by comprising the following steps: under the alkaline condition of KOH, carbazole reacts with methylbutynol in an ethanol solvent to generate N-vinyl carbazole:
2. the method for synthesizing N-vinylcarbazole according to claim 1, characterized in that the molar ratio of carbazole to methylbutynol is 1.
3. The method for synthesizing N-vinylcarbazole according to claim 1, characterized in that the reaction temperature is 75 to 80 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910652859.3A CN110386895B (en) | 2019-07-19 | 2019-07-19 | Method for synthesizing N-vinyl carbazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910652859.3A CN110386895B (en) | 2019-07-19 | 2019-07-19 | Method for synthesizing N-vinyl carbazole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110386895A CN110386895A (en) | 2019-10-29 |
| CN110386895B true CN110386895B (en) | 2022-11-01 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201910652859.3A Active CN110386895B (en) | 2019-07-19 | 2019-07-19 | Method for synthesizing N-vinyl carbazole |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20080036483A (en) * | 2006-10-23 | 2008-04-28 | 삼성에스디아이 주식회사 | Organoelectroluminescent compound and organoelectroluminescent device employing the same |
| CN104130180A (en) * | 2014-07-25 | 2014-11-05 | 南通市华峰化工有限责任公司 | Method for preparing N-vinyl carbazole |
| CN107112380A (en) * | 2015-01-09 | 2017-08-29 | 东丽株式会社 | Photo-electric conversion element and use its imaging sensor |
-
2019
- 2019-07-19 CN CN201910652859.3A patent/CN110386895B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20080036483A (en) * | 2006-10-23 | 2008-04-28 | 삼성에스디아이 주식회사 | Organoelectroluminescent compound and organoelectroluminescent device employing the same |
| CN104130180A (en) * | 2014-07-25 | 2014-11-05 | 南通市华峰化工有限责任公司 | Method for preparing N-vinyl carbazole |
| CN107112380A (en) * | 2015-01-09 | 2017-08-29 | 东丽株式会社 | Photo-electric conversion element and use its imaging sensor |
Non-Patent Citations (3)
| Title |
|---|
| Novel Diethynylcarbazole Macrocycles: Synthesis and Optoelectronic Properties;Tianyue Zhao et al.;《J.Org.Chem.》;20060824;第71卷;第7424页SCHEME 1、SCHEME 2 * |
| N-乙烯基咔唑的合成新工艺研究;刘长春 等;《河南科学》;20200630;第38卷(第6期);第886-890页 * |
| Substrate-Controlled Regio- and Stereoselective Synthesis of (Z)- and (E)-N-Styrylated Carbazoles, Aza-carbazoles, and γ-Carbolines via Hydroamination of Alkynes;Vineeta Garg et al.;《J.Org.Chem.》;20180824;第83卷;第11693页Table 3 * |
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| CN110386895A (en) | 2019-10-29 |
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