CN113956258B - Preparation method of indolo [2,3-A ] carbazole by adopting acidic ionic liquid - Google Patents
Preparation method of indolo [2,3-A ] carbazole by adopting acidic ionic liquid Download PDFInfo
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0285—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre also containing elements or functional groups covered by B01J31/0201 - B01J31/0274
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Abstract
The invention discloses a preparation method of indolo [2,3-A ] carbazole, which comprises the following steps: 1, 2-cyclohexanedione and phenylhydrazine hydrochloride are used as starting materials, a solvent A and a solvent B are used as mixed solvents, and catalytic reaction is carried out in the presence of an acidic ionic liquid catalyst to prepare the indolo [2,3-A ] carbazole, wherein the reaction formula is shown as follows; wherein the solvent A is an alcohol solvent, and the solvent B is water. The preparation method adopts the sulfonic acid type ionic liquid as a catalyst, so that the reaction can be carried out at the low temperature of 50-80 ℃, the adopted sulfonic acid type ionic liquid can be recycled, the mixed solvent of alcohols and water does not belong to a high boiling point solvent, the reaction yield can be greatly improved, and the technical problems of high reaction temperature, high solvent boiling point, severe reaction condition and high energy consumption in the prior art can be solved.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent material synthesis, in particular to a preparation method of indolo [2,3-A ] carbazole by adopting acidic ionic liquid.
Background
An OLED (Organic Light-Emitting Diode) is an Organic electroluminescent device with a multi-layer structure, which can be applied to the fields of display and illumination, and is a third generation display technology based on electroluminescence after CRT (cathode ray tube) and LCD (liquid crystal) display. As a new display technology, OLED is currently in the early stage of industrial explosion, and according to the development history of the display technology, the next ten years or the age that OLED is gradually dominant will be. The indolo [2,3-A ] carbazole compounds have excellent optical and electrical properties, and have been widely focused and studied in recent years. Therefore, research on synthesis of indolo [2,3-A ] carbazole is of great importance for the development of OLED industry. According to literature reports, indolo [2,3-A ] carbazole mainly has the following synthetic routes.
Route one: patent KR2011011579 reports a synthetic method of indolo [2,3-a ] carbazole: 1, 2-cyclohexanedione and phenylhydrazine hydrochloride are used as raw materials, and the indolo [2,3-A ] carbazole is obtained through two-step reaction under the action of strong acid such as sulfuric acid, trifluoroacetic acid and the like, and the yield is 77%.
Route two: patent US20140291628 discloses and reports a synthesis method of indolo [2,3-A ] carbazole, which takes p-dibromobenzene as a raw material, and prepares indolo [2,3-A ] carbazole through three steps of nitration, suzuki coupling and triethyl phosphite cyclization, wherein the total reaction yield is about 50%.
Route three: in 2015, panesar et al reported a method for synthesizing indolo [2,3-a ] carbazole from 2, 3-diindolmethane: under the catalysis of sulfuric acid, 2, 3-diindolmethane and trimethyl orthoformate are synthesized into indolo [2,3-A ] carbazole in one step, and the yield is 82%.
The above synthetic route has the following disadvantages or drawbacks:
route one: the synthesis steps are short, but a large amount of strong acid is used in the reaction process to generate a large amount of acid waste liquid, and the defects of long reaction time, low yield, low product purity and the like exist.
Route two: the adopted raw materials are cheap and easy to obtain, but the reaction steps are long, the yield is low, and in the last step of ring closure, triethyl phosphite is used, so that the smell is large, a large amount of by-products such as triphenylphosphine oxide and the like are generated after the reaction, and the environmental protection problem is outstanding; and the reaction is required to be carried out at a high temperature of 180 ℃, so that the final product has darker color and high purification difficulty.
Route three: the reaction condition is mild, the product can be obtained through one-step reaction, but the used raw material 2, 3-diindolylmethane is not easy to obtain, and the price is high, so that the production cost is high, and the industrial production value is not realized.
In addition, the existing preparation methods of other indolo [2,3-A ] carbazole also have the technical problems of high reaction temperature, high boiling point of solvent, harsh reaction conditions and high energy consumption.
Therefore, there is a need to continuously study the synthesis method of indolo [2,3-A ] carbazole in order to obtain a more economical, green and efficient industrial production method of indolo [2,3-A ] carbazole.
The information disclosed in this background section is only for enhancement of understanding of the general background of the invention and should not be taken as an acknowledgement or any form of suggestion that this information forms the prior art already known to a person of ordinary skill in the art.
Disclosure of Invention
The invention aims to provide a preparation method of indolo [2,3-A ] carbazole, which can solve the technical problems of high reaction temperature, high boiling point of a solvent, harsh reaction conditions and high energy consumption in the prior art.
In order to achieve the above object, the present invention provides a method for preparing indolo [2,3-a ] carbazole, comprising: 1, 2-cyclohexanedione and phenylhydrazine hydrochloride are used as starting materials, a solvent A and a solvent B are used as mixed solvents, and catalytic reaction is carried out in the presence of an acidic ionic liquid catalyst to prepare the indolo [2,3-A ] carbazole, wherein the reaction formula is shown as follows; wherein the solvent A is an alcohol solvent, and the solvent B is water;
in an embodiment of the invention, the ionic liquid catalyst is a sulfonic acid type ionic liquid. The sulfonic acid type ionic liquid can be recycled.
In one embodiment of the present invention, the sulfonic acid type ionic liquid is [ (CH) 2 ) 3 SO 3 HMIM][HSO 4 ]Or [ (CH) 2 ) 3 SO 3 HMIM][CF 3 SO 4 ]The method comprises the steps of carrying out a first treatment on the surface of the Wherein [ (CH) 2 ) 3 SO 3 HMIM][HSO 4 ]Or [ (CH) 2 ) 3 SO 3 HMIM][CF 3 SO 4 ]The structural formula is as follows:
in an embodiment of the present invention, the alcohol solvent is one or more of methanol, ethanol, and isopropanol. The adopted solvents of methanol, ethanol and isopropanol have low boiling points and low reaction temperature, so that the energy consumption of the reaction is low, and the production cost is reduced.
In one embodiment of the present invention, the molar ratio of phenylhydrazine hydrochloride to 1, 2-cyclohexanedione is 1 (2.1 to 2.0).
In one embodiment of the present invention, the mass ratio of the ionic liquid catalyst to 1, 2-cyclohexanedione is (0.01 to 0.05): 1.
In one embodiment of the present invention, the mass ratio of the mixed solvent to 1, 2-cyclohexanedione is (5-10): 1.
In one embodiment of the present invention, the mass ratio of the solvent A to the solvent B is (8-9): 1.
In one embodiment of the present invention, the reaction temperature of the catalytic reaction is 50 to 80 ℃; and/or the catalytic reaction is carried out under the condition of stirring and heat preservation for 12-24 hours.
In one embodiment of the invention, the indolo [2,3-A ] carbazole is finally prepared to obtain an indolo [2,3-A ] carbazole product through filtration and crystallization; preferably, the above crystallization is performed by using a mixed solvent of tetrahydrofuran and ethanol.
The invention discloses a preparation method of specific indolo [2,3-A ] carbazole, which comprises the following steps:
(1) Feeding: under the protection of nitrogen, adding 1, 2-cyclohexanedione, phenylhydrazine hydrochloride, an ionic liquid catalyst and a solvent into a reaction system, wherein the molar ratio of the phenylhydrazine hydrochloride to the 1, 2-cyclohexanedione is (2.1-2.0): 1; the ionic liquid catalyst is [ (CH 2) 3SO3HMIM ] [ HSO4] or [ (CH 2) 3SO3HMIM ] [ CF3SO4]; the solvent A is methanol, ethanol or isopropanol, and the solvent B is water; the molar ratio of the ionic liquid catalyst to the 1, 2-cyclohexanedione is (0.01-0.05): 1; the mass ratio of the mixed solvent to the 1, 2-cyclohexanedione is (10-20): 1, and the mass ratio of the solvent A to the solvent B is (8-9): 1; (2) reaction: after the material is fed, the temperature is raised to 50-80 ℃, the stirring rotation speed is 600rpm, the heat preservation reaction is carried out for 12-24 hours, after the reaction is finished, the reaction liquid is filtered, the crude product of the indolo [2,3-A ] carbazole is obtained after filtration, and the crude product is crystallized by a mixed solvent of tetrahydrofuran and ethanol to obtain the indolo [2,3-A ] carbazole product.
And concentrating the filtrate to recover the solvent to obtain the ionic liquid which can be recycled.
Compared with the prior art, the invention has the following advantages:
(1) The invention adopts the acidic ionic liquid, especially the sulfonic acid ionic liquid, as the catalyst, can be carried out at the low temperature of 50-80 ℃, if the reaction is carried out under the condition of not adopting the sulfonic acid ionic liquid, the reaction temperature can be carried out only by reaching 150-200 ℃, and the adopted sulfonic acid ionic liquid can be recycled, so that the high-purity product can be obtained by simple filtration and crystallization in the post-treatment.
(2) The mixed solvent of alcohols and water does not belong to a high boiling point solvent, nonpolar solvents such as decalin, diethylbenzene and diphenyl ether with boiling points exceeding 150 ℃ are avoided, the reaction yield can be greatly improved, and the addition of the solvent water improves the activity of the acidic ionic liquid catalyst, so that the reaction speed is further accelerated, and the reaction yield and selectivity are improved.
In a word, the invention takes 1, 2-cyclohexanedione and phenylhydrazine hydrochloride as starting materials, and prepares the indolo [2,3-A ] carbazole through one-step reaction under the catalysis of acidic ionic liquid, compared with the prior art, the invention has the advantages of greatly reduced reaction temperature, mild reaction condition, short reaction step, recyclable catalyst, low production cost and environmental protection, and solves the technical problems of too high reaction temperature, high boiling point of solvent, harsh reaction condition and high energy consumption in the prior art.
Detailed Description
The following detailed description of specific embodiments of the invention is, but it should be understood that the invention is not limited to specific embodiments.
Throughout the specification and claims, unless explicitly stated otherwise, the term "comprise" or variations thereof such as "comprises" or "comprising", etc. will be understood to include the stated element or component without excluding other elements or components.
Example 1: preparation method of indolo [2,3-A ] carbazole
In a 2L reactor, 56.6g of 1, 2-cyclohexanedione (99%, 0.5 mol), 150.4g of phenylhydrazine hydrochloride (99%, 1.03 mol) and 0.57g of [ (CH) were introduced under nitrogen 2 ) 3 SO 3 HMIM][CF 3 SO 4 ](99%), 510g of methanol, 57g of water; after the material is fed, the temperature is raised to 50 ℃, the stirring speed is 600rpm, and the reaction is kept for 24 hours; after the reaction is finished, the reaction solution is filtered, a filter cake is washed by 100mL of methanol to obtain a crude product, and 125.9g of indolo [2,3-A ] is obtained by crystallizing the crude product by a mixed solvent of tetrahydrofuran and ethanol in a volume ratio of 1:1]Carbazole content is more than or equal to 99.99%, yield is 98.2%; wherein, the filtrate is used for recovering the solvent to obtain 0.88g of recovered ionic liquid [ (CH) 2 ) 3 SO 3 HMIM][CF 3 SO 4 ]。
Example 2: preparation method of indolo [2,3-A ] carbazole
56.6g of the mixture was introduced into a 2L reactor under nitrogen atmosphere1, 2-cyclohexanedione (99%, 0.5 mol), 153.4g of phenylhydrazine hydrochloride (99%, 1.05 mol), 2.83g of [ (CH) 2 ) 3 SO 3 HMIM][HSO 4 ](99%), 403g of ethanol, 50g of water; after the material is fed, the temperature is raised to 80 ℃, the stirring speed is 600rpm, and the heat preservation reaction is carried out for 12 hours; after the reaction is finished, the reaction solution is filtered, a filter cake is washed by 100mL of ethanol to obtain a crude product, and the crude product is crystallized by a mixed solvent of tetrahydrofuran and ethanol in a volume ratio of 1:1 to obtain 123.2g of indolo [2,3-A]Carbazole content is more than or equal to 99.99%, yield is 96.1%; wherein, 4.82g of recovered ionic liquid [ (CH) is obtained after the filtrate is used for recovering the solvent 2 ) 3 SO 3 HMIM][HSO 4 ]。
Example 3: preparation method of indolo [2,3-A ] carbazole
In a 2L reactor, 56.6g of 1, 2-cyclohexanedione (99%, 0.5 mol), 150.4g of phenylhydrazine hydrochloride (99%, 1.03 mol) and 0.57g of [ (CH) were introduced under nitrogen 2 ) 3 SO 3 HMIM][CF 3 SO 4 ](99%), 510g of methanol, 57g of water; after the material is fed, heating to 60 ℃, stirring at 600rpm, and reacting for 20hr; after the reaction is finished, the reaction solution is filtered, a filter cake is washed by 100mL of methanol to obtain a crude product, and 125.1g of indolo [2,3-A ] is obtained by crystallizing the crude product by a mixed solvent of tetrahydrofuran and ethanol in a volume ratio of 1:1]Carbazole content is more than or equal to 99.99%, yield is 97.6%; wherein, the filtrate is used for recovering the solvent to obtain 1.12g of recovered ionic liquid [ (CH) 2 ) 3 SO 3 HMIM][CF 3 SO 4 ]。
Example 4: preparation method of indolo [2,3-A ] carbazole
In a 2L reactor, 56.6g of 1, 2-cyclohexanedione (99%, 0.5 mol), 153.4g of phenylhydrazine hydrochloride (99%, 1.05 mol) and 2.83g of [ (CH) are introduced under nitrogen 2 ) 3 SO 3 HMIM][HSO 4 ](99%), 509g of isopropanol, 57g of water; after the material is fed, the temperature is raised to 70 ℃, the stirring speed is 600rpm, and the reaction is kept for 15 hours; after the reaction is finished, the reaction solution is filtered, a filter cake is washed by 100mL of ethanol to obtain a crude product, and 125.7g of indolo [2,3-A ] is obtained by crystallizing the crude product by a mixed solvent of tetrahydrofuran and ethanol in a volume ratio of 1:1]Carbazole with the content more than or equal to 99.99 percent,yield 98.1%; wherein, 4.61g of recovered ionic liquid [ (CH) is obtained after the filtrate is used for recovering the solvent 2 ) 3 SO 3 HMIM][HSO 4 ]。
Comparative example 1: preparation method of indolo [2,3-A ] carbazole
The only difference between this comparative example 1 and example 1 is that: no sulfonic acid type ionic liquid [ (CH) 2 ) 3 SO 3 HMIM][CF 3 SO 4 ]As catalysts, instead non-sulphonic acid ionic liquids [ BMIM ] are used][HSO 4 ](1-butyl-3-methylimidazole bisulfate).
In a 2L reactor, 56.6g of 1, 2-cyclohexanedione (99%, 0.5 mol), 150.4g of phenylhydrazine hydrochloride (99%, 1.03 mol), 0.57g of [ BMIM ] are introduced under nitrogen][HSO 4 ](1-butyl-3-methylimidazole bisulfate) (99%), 510g of methanol, 57g of water; after the material is fed, the temperature is raised to 50 ℃, the stirring speed is 600rpm, and the reaction is kept for 24 hours; after the reaction is finished, the reaction solution is filtered, a filter cake is washed by 100mL of methanol to obtain a crude product, and the crude product is crystallized by a mixed solvent of tetrahydrofuran and ethanol in a volume ratio of 1:1 to obtain 81.3g of indolo [2,3-A]Carbazole content 98% and yield 62.2%.
Therefore, the ionic liquid catalyst adopted by the invention is the sulfonic acid type ionic liquid specially selected for the reaction system, and the addition of the sulfonic acid group enhances the acidity of the ionic liquid, so that the catalytic effect is obviously improved; if the ionic liquid without sulfonic acid groups is not added, the technical effect of high yield and high purity of the invention cannot be realized.
Comparative example 2: preparation method of indolo [2,3-A ] carbazole
The only difference between this comparative example 1 and example 1 is that: no mixed solvent is used, only a single solvent of methanol is used, and no water is used.
In a 2L reactor, 56.6g of 1, 2-cyclohexanedione (99%, 0.5 mol), 150.4g of phenylhydrazine hydrochloride (99%, 1.03 mol) and 0.57g of [ (CH) were introduced under nitrogen 2 ) 3 SO 3 HMIM][CF 3 SO 4 ](99%), 566g of methanol; after the material is fed, the temperature is raised to 50 ℃, the stirring speed is 600rpm, and the quality is ensuredReacting at a temperature for 24hr; after the reaction is finished, the reaction solution is filtered, a filter cake is washed by 100mL of methanol to obtain a crude product, and the crude product is crystallized by a mixed solvent of tetrahydrofuran and ethanol in a volume ratio of 1:1 to obtain 94.5g of indolo [2,3-A]Carbazole content 98% and yield 72.26%.
It follows that the addition of water is critical in the present invention, and that the yield of the reaction is greatly reduced if no water is added using a single solvent.
Recycling of sulfonic acid type ionic liquid catalyst:
the ionic liquid catalyst can be recycled, and can still maintain high yield of reaction, thereby being environment-friendly and saving cost.
The ionic liquid catalyst recovered in example 1 was used, the reaction procedure in example 1 was repeated, the catalyst was used 3 times, and the reaction conditions were as follows.
TABLE 1 acidic ionic liquids [ (CH) 2 ) 3 SO 3 HMIM][CF 3 SO 4 ]Applying the reaction result
Therefore, the acidic ionic liquid adopted by the invention still has good catalytic effect after being recycled for a plurality of times and reused for reaction, and the product content can still reach more than 99.99 percent, and the yield reaches more than 97 percent.
The foregoing descriptions of specific exemplary embodiments of the present invention are presented for purposes of illustration and description. It is not intended to limit the invention to the precise form disclosed, and obviously many modifications and variations are possible in light of the above teaching. The exemplary embodiments were chosen and described in order to explain the specific principles of the invention and its practical application to thereby enable one skilled in the art to make and utilize the invention in various exemplary embodiments and with various modifications as are suited to the particular use contemplated. It is intended that the scope of the invention be defined by the claims and their equivalents.
Claims (2)
1. A method for preparing indolo [2,3-a ] carbazole, which is characterized by comprising the following steps: 1, 2-cyclohexanedione and phenylhydrazine hydrochloride are used as starting materials, a solvent A and a solvent B are used as mixed solvents, catalytic reaction is carried out in the presence of an acidic ionic liquid catalyst to prepare the indolo [2,3-A ] carbazole, and finally the indolo [2,3-A ] carbazole is prepared, filtered and crystallized to obtain the indolo [2,3-A ] carbazole product, wherein the reaction formula is shown as the following formula;
wherein the solvent A is an alcohol solvent, the solvent B is water, the ionic liquid catalyst is a sulfonic acid type ionic liquid, and the sulfonic acid type ionic liquid is [ (CH) 2 ) 3 SO 3 HMIM][HSO 4 ]Or [ (CH) 2 ) 3 SO 3 HMIM][CF 3 SO 3 ]The structural formula is as follows:
the mass ratio of the ionic liquid catalyst to the 1, 2-cyclohexanedione is (0.01-0.05) 1; the alcohol solvent is one or more of methanol, ethanol and isopropanol; the mass ratio of the solvent A to the solvent B is (8-9) 1; the mass ratio of the mixed solvent to the 1, 2-cyclohexanedione is (5-10) 1; the reaction temperature of the catalytic reaction is 50-80 ℃; and/or the catalytic reaction is carried out under the conditions of stirring and heat preservation for 12-24 hours; the crystallization adopts a mixed solvent of tetrahydrofuran and ethanol for crystallization.
2. The process according to claim 1, wherein the molar ratio of phenylhydrazine hydrochloride to 1, 2-cyclohexanedione is from (2.1 to 2.0): 1.
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| Yong-Zhou Hu.An Efficient and General Synthesis of Indolo[2,3-a]carbazoles Using the Fischer Indole Synthesis.《LETTER》.2005,42-48. * |
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