Method for preparation of bibenzyl compounds by photocatalytic one-step process

A compound and photocatalytic technology, applied in the preparation of organic compounds, organic chemical methods, chemical instruments and methods, etc., can solve the problems of toxicity, large amount of catalyst usage, high cost of raw materials, etc., achieve simple and safe operation process, and broaden product categories , prepare simple effects

Active Publication Date: 2019-06-18
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • 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

Method used

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  • Method for preparation of bibenzyl compounds by photocatalytic one-step process
  • Method for preparation of bibenzyl compounds by photocatalytic one-step process
  • Method for preparation of bibenzyl compounds by photocatalytic one-step process

Examples

Experimental program
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Effect test

Embodiment 1

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

Embodiment 2

[0041] In a 5ml quartz glass reaction tube, add 1.0ml toluene and weigh 10mg Ru-ZnIn 2 S 4 -0.5 Catalyze the reaction, replace the reaction tube with argon and seal it, and the radiant flux of 1.8W LED (450~460nm) at room temperature is illuminated for 12h. After the reaction is over, the product is detected by chromatography. The product mass spectrum and standard mass spectrum Figure one To. After the reaction, toluene is distilled out, and the toluene is recycled. The yield of 1,2-diphenylethane is 2.16g (g catalyst) -1 , The selectivity is 80%.

[0042] Ru-ZnIn 2 S 4 -0.5 catalyst is prepared by one-step hydrothermal method. 294mg zinc sulfate heptahydrate, 624mg indium trichloride tetrahydrate, 260mg cetylammonium bromide and 0.538mg RuCl 3 Add to 20mL of water; add 605mg of thioacetamide after stirring for half an hour; continue stirring for half an hour and then hydrothermally heat at 160°C for 20 hours. After cooling to room temperature, the crude Ru-ZnIn 2 S 4 -0.5 Th...

Embodiment 3

[0044] In a 100ml quartz glass reaction flask, add 20ml toluene and weigh 200mg Ru-ZnIn 2 S 4 -0.5 Catalyze the reaction, replace the reaction flask with argon and seal it, normal temperature xenon lamp (> 420nm, radiant flux 28.8W) illumination for 8h, after the reaction, the product is detected by chromatography, the product mass spectrum and standard mass spectrum Figure one To. After the reaction, toluene is distilled out, and the toluene is recycled. The yield of 1,2-diphenylethane is 15.9g (g catalyst) -1 , The selectivity is 74%. The catalyst preparation steps are the same as in Example 2, and the 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, and specifically relates to basic reaction processes such as direct photocatalytic dehydrogenation and coupling of toluene. Background technique [0002] Bibenzyl compounds are important intermediates for the synthesis of fine chemicals and can be used in chemical industries such as flame retardant, leather processing, fluorescent whitening, fuel, and medicine. The sulfonation product of 1,2-diphenylethane is an excellent tanning agent in the leather processing industry. In addition, the dehydrogenation products produced from 1,2-diphenylethane as raw materials (such as 1,2-stilbene, benzophenone) can be used to synthesize fluorescent brighteners 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 pharmaceutical and che...

Claims

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Application Information

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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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