A photocatalytic one-step method for preparing bibenzyl compounds

A technology of photocatalysis and bibenzyls, which is applied in the field of photocatalytic one-step preparation of bibenzyls from toluene derivatives, can solve the problems of toxicity, large amount of catalyst used, and high cost of raw materials, and achieve simple and safe operation process and high product quality. The effect of broadening the variety and making it simple

Active Publication Date: 2021-01-22
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] At present, there are many problems in the preparation route of bibenzyl compounds, such as high toxicity of raw materials, large amount of catalyst used and not recyclable, high cost of raw materials, use of a large number of dangerous, toxic, environment-polluting and highly corrosive raw materials or homogeneous catalysts, etc.

Method used

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  • A photocatalytic one-step method for preparing bibenzyl compounds
  • A photocatalytic one-step method for preparing bibenzyl compounds
  • A photocatalytic one-step method for preparing bibenzyl compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0039] In a 5ml quartz glass reaction tube, add 1.0ml toluene respectively, weigh 10mg ZnIn 2 S 4 Catalyze the reaction, replace the reaction tube with argon gas and seal it, and illuminate it with a 1.8W LED (450-460nm) at room temperature for 12 hours. After the reaction, the product is detected by chromatography, and the mass spectrum of the product is compared with the standard mass spectrum. Figure 1 Sincerely. After the reaction, the toluene is distilled off, and the toluene is recycled. The yield of 1,2-diphenylethane is 0.75g (g catalyst) -1 , with a selectivity of 85%. The catalyst preparation steps are the same as in Example 2, and the preparation raw material components are shown in Table 1.

Embodiment 2

[0041] In a 5ml quartz glass reaction tube, add 1.0ml toluene respectively, weigh 10mg Ru-ZnIn 2 S 4 -0.5 catalyzes the reaction, replaces the reaction tube with argon gas and seals it, and irradiates it with a 1.8W LED (450-460nm) at room temperature for 12 hours. After the reaction, the product is detected by chromatography, and the product mass spectrum and standard mass spectrum Figure 1 Sincerely. After the reaction, the toluene is distilled off, and the toluene is recycled. The yield of 1,2-diphenylethane is 2.16g (g catalyst) -1 , with a selectivity of 80%.

[0042] Ru-ZnIn 2 S 4 The -0.5 catalyst was prepared by a one-step hydrothermal method. 294mg of zinc sulfate heptahydrate, 624mg of indium trichloride tetrahydrate, 260mg of cetyl ammonium bromide and 0.538mg of RuCl 3 Add it to 20mL of water; add 605mg of thioacetamide after stirring for half an hour; continue stirring for half an hour and then heat it in water at 160°C for 20h. After cooling to room temp...

Embodiment 3

[0044] In a 100ml quartz glass reaction bottle, add 20ml toluene respectively, weigh 200mg Ru-ZnIn 2 S 4 -0.5 catalyzes the reaction, replaces the reaction bottle with argon gas and seals it, and irradiates it with a xenon lamp (>420nm, radiant flux 28.8W) at room temperature for 8 hours. After the reaction, the product is detected by chromatography, and the product mass spectrum and standard mass spectrum Figure 1 Sincerely. After the reaction, the toluene is distilled off, and the toluene is recycled. The yield of 1,2-diphenylethane is 15.9g (g catalyst) -1 , selectivity 74%. The catalyst preparation steps are the same as in Example 2, and the preparation raw material components are shown in Table 1.

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Abstract

The invention relates to a brand new low-cost method for synthesis of bibenzyl compounds. The method adopts green and clean light energy as the reaction energy, and takes toluene or a toluene derivative as the raw material to prepare bibenzyl compounds under the catalysis of a solid photocatalyst. The method is carried out at room temperature, and can prepare bibenzyl compounds directly by illumination. The reaction process includes: mixing a toluene derivative, a catalyst and a solvent, then putting the mixture into a pressure-resistant quartz container (larger than 1MPa), and performing replacement with inert gas, conducting illumination stirring at room temperature, and carrying out reaction for 1 or more hour. At the end of the reaction, the catalyst can be easily separated from the reaction system and can be recycled repeatedly, the reaction product can be separated by crystallization, and the yield of bibenzyl compounds can reach 3.21g (g catalyst)<-1>h<-1>. The method can be used for direct preparation of 1, 2-diphenylethane and natural bibenzyl drugs.

Description

technical field [0001] The invention relates to a photocatalytic one-step method for preparing bibenzyl compounds from toluene derivatives, in particular to basic reaction processes such as photocatalytic direct dehydrogenation and coupling of toluene. Background technique [0002] Bibenzyl compounds are important intermediates in the synthesis of fine chemicals, and can be used in chemical industries such as flame retardant, leather processing, fluorescent whitening, fuel, and pharmaceuticals. The sulfonated reaction product of 1,2-diphenylethane is an excellent tanning agent in the leather processing industry. In addition, the dehydrogenation and oxidation products (such as 1,2-diphenylethylene, diacetophenone) produced from 1,2-diphenylethane can be used to synthesize fluorescent whitening agents and dyes. Due to its high boiling point, high thermal stability and large heat carrying capacity, 1,2-diphenylethane is an excellent heat transfer oil and has been used in the p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/00C07D207/323C07D307/36C07C2/76C07C15/18C07C41/30C07C43/205C07C17/269C07C25/18C07C37/11C07C39/16C07C43/23B01J27/045
Inventor 王峰罗能超侯婷婷王敏
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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