CN109970501B - New preparation method of 1, 2-diphenylethane - Google Patents
New preparation method of 1, 2-diphenylethane Download PDFInfo
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- 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
- B01J31/0281—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 the nitrogen being a ring member
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Abstract
The invention discloses a preparation method of 1, 2-diphenylethane. Uniformly mixing benzene, ethylene oxide and acidic hybrid mesoporous material supported imidazole ionic liquid in a reaction container, and then adding the mixture to the reaction container at a temperature of 20-90 DEG CoAnd C, stirring and reacting for 1-10 hours to obtain 1, 2-diphenylethane, filtering to separate a product phase and a catalyst phase, distilling the filtrate, and recrystallizing the crude product with methanol to obtain a pure product. According to the invention, the acidic hybrid mesoporous material supported imidazole ionic liquid is used as the catalyst, so that the catalyst has high activity, high catalytic efficiency and good stability, and can be conveniently recycled; the reaction product has high yield, the reaction process is simple and convenient to operate, and the reaction environment is green and safe, so that the preparation method is environment-friendly.
Description
Technical Field
The invention relates to a novel environment-friendly method for preparing 1, 2-diphenylethane by catalyzing acidic hybrid mesoporous material supported imidazole ionic liquid, belonging to the technical field of fine chemical engineering.
Technical Field
1, 2-diphenylethane is an important fine organic synthesis intermediate, and can be applied to the production of medicines, flame retardants, fluorescent whitening agents, dyes and the like. At present, the main method for producing 1, 2-diphenylethane at home and abroad is a Friedel-crafts alkylation reaction method, benzene and 1, 2-dichloroethane are subjected to alkylation reaction under the condition of aluminum trichloride serving as a catalyst to obtain (CN109160869A), the process has the advantages of wide raw material source, high yield and high product purity, but the reaction is carried out under the anhydrous condition, the reaction process has the problems of low selectivity, a large amount of hydrogen chloride gas generated by the reaction pollutes the environment and corrodes equipment, the catalyst cannot be recovered, the operation cost is high and the like. In patent CN109456138A, compound ionic liquid is used as a catalyst to catalyze benzene and 1, 2-dichloroethane to generate alkylation reaction in a liquid phase to generate 1, 2-diphenylethane, and the compound ionic liquid is a mixed liquid of aluminum trichloride ionic liquid and ferric trichloride ionic liquid. Although the ionic liquid catalysis method has higher reaction efficiency, the dosage of benzene is greatly excessive in order to keep higher selectivity in the reaction process, which greatly increases the operation cost; in addition, a large amount of hydrogen chloride gas is generated in the reaction, so that the problems of environmental pollution, equipment corrosion and the like are difficult to completely avoid. Other synthesis methods for 1, 2-diphenylethane are the warz-chloride coupling (chemical and engineering techniques, 2010,31(6):45-48), the geiger-chloride coupling (US2392595A), the benzyl chloride (iron powder) coupling (CN 101318873A; CN101643384A), the benzoin reduction reaction, (JP3232825B), the alkylation of benzene with ethylene oxide (chemical and engineering techniques, 2010,31(6): 45-48). The Wutz coupling method reaction needs a large amount of metal sodium, has serious potential safety hazard problem and is very easy to cause fire and explosion; although the Grignard reagent coupling method has high product yield and good purity, the reaction needs anhydrous operation, the cost is high, the safety control is difficult to realize, and the industrial production is difficult to realize; the catalyst can not be recovered in the coupling reaction process of benzyl chloride (iron powder), the waste water in the process is large, and the environmental protection pressure is large; the catalyst palladium in the benzoin reduction method is expensive, the production cost is high, the reaction steps are long, and the post-treatment is troublesome; although the alkylation method of benzene and ethylene oxide solves the problem of corrosion pollution of alkylation reaction, the reaction has the problems of low yield, low selectivity and the like. Therefore, the research and development of a novel and efficient environment-friendly preparation method of the 1, 2-diphenylethane has very important significance.
Disclosure of Invention
In order to solve the technical problems, the invention provides a method for preparing 1, 2-diphenylethane by an efficient and environment-friendly alkylation reaction, and a target is prepared by catalyzing benzene and ethylene oxide to perform a Friedel-crafts alkylation reaction by using an acidic hybrid mesoporous material loaded imidazole ionic liquid.
The chemical reaction principle and the structure of the preparation method of the acidic hybrid mesoporous material supported ionic liquid catalyst are as follows:
the anion Y of the ionic liquid in the general formula can be FeCl4,AlCl4,TiCl5,RhCl4,RuCl4,InCl4And (4) negative ions.
Uniformly mixing benzene, ethylene oxide and acidic hybrid mesoporous material supported imidazole ionic liquid in a reaction container, stirring and reacting for 1-10 hours at 20-90 ℃ to obtain 1, 2-diphenylethane, separating a product phase and a catalyst phase by filtering, distilling filtrate, recrystallizing a crude product by methanol, and drying to obtain a pure product.
The molar ratio of the materials used is ethylene oxide: the ratio of benzene to benzene is 1: 2-12, and the dosage of the acidic hybrid mesoporous material supported imidazole ionic liquid is 1-40% of the mass of the benzene material.
In the preferred scheme, the molar ratio of the ethylene oxide to the benzene is 1: 2-8; the amount of the catalyst is 2-20% of the mass of the benzene material.
The reaction temperature is controlled to be 20-90 ℃, and the reaction time is controlled to be 1-10 hours. Preferably, the reaction temperature is controlled to be 30-80 ℃, and the reaction time is controlled to be 2-8 hours.
The ethylene oxide is an ethylene oxide water solution, and the mass percent concentration of the ethylene oxide is 10-99%, and the preferred mass percent concentration is 30-95%.
The catalyst is one of acidic hybrid mesoporous material supported imidazolium ferric chloride salt ionic liquid, acidic hybrid mesoporous material supported imidazolium aluminum chloride salt ionic liquid, acidic hybrid mesoporous material supported imidazolium titanium chloride salt ionic liquid, acidic hybrid mesoporous material supported imidazolium rhodium chloride salt ionic liquid, acidic hybrid mesoporous material supported imidazolium ruthenium chloride salt ionic liquid and acidic hybrid mesoporous material supported imidazolium indium chloride salt ionic liquid.
According to the method for preparing the 1, 2-diphenylethane through the catalytic alkylation reaction of the acidic hybrid mesoporous material supported imidazole ionic liquid, after the reaction is finished, a product phase and a catalyst phase can be separated through filtration, a filtrate is distilled, a crude product is recrystallized through methanol and dried to obtain a pure product, the solid catalyst can be recycled without being treated, and the solid catalyst can be fed in proportion for the next batch of catalytic reaction.
The catalytic reaction principle of the invention is as follows:
according to the method for preparing 1, 2-diphenylethane provided by the invention, the key technology is that the prepared acidic hybridization mesoporous material loaded imidazole ionic liquid is adopted to catalyze benzene and ethylene oxide to carry out Friedel-crafts alkylation reaction to obtain the 1, 2-diphenylethane.
Compared with the prior catalytic reaction technology, the invention has the advantages that: (1) the acidic hybrid mesoporous material supported imidazole ionic liquid catalyst has high catalytic activity and good stability, and can be conveniently recycled. (2) The method is green and efficient, the reaction efficiency is obviously improved, the highest yield of the 1, 2-diphenylethane can reach 82%, and the highest purity can reach 98.5%. (3) The whole reaction system is heterogeneous catalysis, the product phase and the catalyst phase are separated simply, the operation process is simplified, an organic solvent and an additive are not required to be added in the reaction process, and the reaction system is safe and environment-friendly.
Detailed Description
The present invention will be described in further detail with reference to the following examples, but the present invention is not limited thereto.
Example 1
Benzene (0.3mol), 50% ethylene oxide (0.1mol) and acidic hybrid mesoporous material supported imidazole ferric chloride salt ionic liquid (2.0g) are added into a round-bottom flask, heated to 45 ℃, and stirred for reaction for 3 hours. The product phase and the catalyst phase can be separated by filtration, the filtrate is distilled, the crude product is recrystallized by methanol and dried to obtain the product 1, 2-diphenylethane with the yield of 52 percent. The LC-MS analysis result shows that the purity of the 1, 2-diphenylethane is 93.7 percent.
Example 2
Benzene (0.3mol), 70% ethylene oxide (0.1mol) and acidic hybrid mesoporous material supported imidazole aluminum chloride salt ionic liquid (2.0g) are added into a round-bottom flask, heated to 45 ℃, and stirred for reaction for 4 hours. The product phase and the catalyst phase can be separated by filtration, the filtrate is distilled, the crude product is recrystallized by methanol and dried to obtain the product 1, 2-diphenylethane with the yield of 64 percent. The LC-MS analysis result shows that the purity of the 1, 2-diphenylethane is 96.4 percent.
Example 3
Benzene (0.4mol), 80% ethylene oxide (0.1mol) and acidic hybrid mesoporous material supported imidazole titanium chloride ionic liquid (2.0g) are added into a round-bottom flask, heated to 40 ℃, and stirred for reaction for 4 hours. The product phase and the catalyst phase can be separated by filtration, the filtrate is distilled, the crude product is recrystallized by methanol and dried to obtain the product 1, 2-diphenylethane with the yield of 78 percent. The LC-MS analysis result shows that the purity of the 1, 2-diphenylethane is 96.8 percent.
Example 4
Benzene (0.4mol), 80% ethylene oxide (0.1mol) and acidic hybrid mesoporous material supported imidazole rhodium chloride ionic liquid (2.5g) are added into a round-bottom flask, heated to 50 ℃, and stirred for reaction for 6 hours. The product phase and the catalyst phase can be separated by filtration, the filtrate is distilled, the crude product is recrystallized by methanol and dried to obtain the product 1, 2-diphenylethane with the yield of 63 percent. The LC-MS analysis result shows that the purity of the 1, 2-diphenylethane is 97.3 percent.
Example 5
Benzene (0.4mol), 90% ethylene oxide (0.1mol) and acidic hybrid mesoporous material supported imidazole ruthenium chloride ionic liquid (2.5g) are added into a round-bottom flask, heated to 45 ℃, and stirred for reaction for 3 hours. The product phase and the catalyst phase can be separated by filtration, the filtrate is distilled, the crude product is recrystallized by methanol and dried to obtain the product 1, 2-diphenylethane with the yield of 71 percent. The LC-MS analysis result shows that the purity of the 1, 2-diphenylethane is 97.1 percent.
Example 6
Benzene (0.4mol), 90% ethylene oxide (0.1mol) and acidic hybrid mesoporous material supported imidazole indium chloride ionic liquid (3.0g) are added into a round-bottom flask, heated to 45 ℃, and stirred for reaction for 5 hours. The product phase and the catalyst phase can be separated by filtration, the filtrate is distilled, the crude product is recrystallized by methanol and dried to obtain the product 1, 2-diphenylethane with the yield of 79 percent. The LC-MS analysis result shows that the purity of the 1, 2-diphenylethane is 97.7 percent.
Example 7
Benzene (0.5mol), 90% ethylene oxide (0.1mol) and acidic hybrid mesoporous material supported imidazole titanium chloride ionic liquid (3.5g) are added into a round-bottom flask, heated to 40 ℃, and stirred for reaction for 4 hours. The product phase and the catalyst phase can be separated by filtration, the filtrate is distilled, the crude product is recrystallized by methanol and dried to obtain the product 1, 2-diphenylethane with the yield of 82 percent. The LC-MS analysis result shows that the purity of the 1, 2-diphenylethane is 98.1 percent.
Example 8
Benzene (0.5mol), 90% ethylene oxide (0.1mol) and acidic hybrid mesoporous material supported imidazole ruthenium chloride ionic liquid (3.5g) are added into a round-bottom flask, heated to 45 ℃, and stirred for reaction for 3 hours. The product phase and the catalyst phase can be separated by filtration, the filtrate is distilled, the crude product is recrystallized by methanol and dried to obtain the product 1, 2-diphenylethane with the yield of 77 percent. The LC-MS analysis result shows that the purity of the 1, 2-diphenylethane is 97.8 percent.
Example 9
Benzene (0.5mol), 90% ethylene oxide (0.1mol) and acidic hybrid mesoporous material supported imidazole indium chloride ionic liquid (3.5g) are added into a round-bottom flask, heated to 45 ℃, and stirred for reaction for 5 hours. The product phase and the catalyst phase can be separated by filtration, the filtrate is distilled, the crude product is recrystallized by methanol and dried to obtain the product 1, 2-diphenylethane with the yield of 80 percent. The LC-MS analysis result shows that the purity of the 1, 2-diphenylethane is 98.5 percent.
Example 10
The catalyst in the example 6 is recovered, the catalytic alkylation reaction is carried out according to the conditions in the example 6, the recovered catalyst is repeatedly used for 8 times, and the experimental result shows that the activity of the catalyst is not reduced, the yield of the 1, 2-diphenylethane is 70-78%, and the purity of the 1, 2-diphenylethane is more than 96.0%.
Example 11
The catalyst in the example 7 is recovered, the catalytic alkylation reaction is carried out according to the conditions in the example 7, the recovered catalyst is repeatedly used for 8 times, and the experimental result shows that the activity of the catalyst is not reduced, the yield of the 1, 2-diphenylethane is 75-82%, and the purity of the 1, 2-diphenylethane is more than 96.5%.
Example 12
The catalyst in the example 9 is recovered, the catalytic alkylation reaction is carried out according to the conditions in the example 9, the recovered catalyst is repeatedly used for 8 times, and the experimental result shows that the activity of the catalyst is not reduced, the yield of the 1, 2-diphenylethane is 73-79%, and the purity of the 1, 2-diphenylethane is more than 97.0%.
Claims (7)
1. A preparation method of 1, 2-diphenylethane is characterized in that benzene, ethylene oxide and acidic hybrid mesoporous material supported imidazole ionic liquid are uniformly mixed in a reaction container, then the mixture is stirred and reacted for 1-10 hours at the temperature of 20-90 ℃ to prepare the 1, 2-diphenylethane, a product phase and a catalyst phase can be separated through filtration, filtrate is distilled, a crude product is recrystallized through methanol and dried to obtain a pure product, and the chemical reaction principle and the structure of the preparation method of the acidic hybrid mesoporous material supported ionic liquid catalyst are as follows:
2. the process for the preparation of 1, 2-diphenylethane as claimed in claim 1, wherein the molar ratio of the materials used is ethylene oxide: the ratio of benzene to benzene is 1: 2-12, and the dosage of the acidic hybrid mesoporous material supported imidazole ionic liquid is 1-40% of the mass of the benzene material.
3. The method for preparing 1, 2-diphenylethane as claimed in claim 2, wherein the molar ratio of ethylene oxide to benzene is 1: 2-8; the amount of the catalyst is 2-20% of the mass of the benzene material.
4. The method for producing 1, 2-diphenylethane as claimed in claim 1, wherein the reaction temperature is controlled to 20 to 90 ℃ and the reaction time is controlled to 1 to 10 hours.
5. The method for preparing 1, 2-diphenylethane as claimed in claim 4, wherein the reaction temperature is controlled to 30-80 ℃ and the reaction time is controlled to 2-8 hours.
6. The method for preparing 1, 2-diphenylethane as claimed in claim 1, wherein the ethylene oxide is an aqueous solution of ethylene oxide, and the concentration of the ethylene oxide is 10-99% by mass.
7. The method for preparing 1, 2-diphenylethane as claimed in claim 1, wherein the ethylene oxide is an aqueous solution of ethylene oxide, and the concentration of the ethylene oxide is 30-95% by mass.
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| CN102603451A (en) * | 2012-02-28 | 2012-07-25 | 南开大学 | Method for preparing diphenylethane catalyzed by mixed liquid of concentrated sulfuric acid and ion liquid |
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| Esterification of the Primary Benzylic C−H Bonds with Carboxylic Acids Catalyzed by Ionic Iron(III) Complexes Containing an Imidazolinium Cation;Bing Lu,et al.;《Organic Letters》;20170215;第19卷(第5期);全文 * |
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