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Method for continuously preparing bibenzyl by using microchannel reaction device

A technology of microchannel reaction and microchannel reactor, applied in chemical instruments and methods, chemical/physical/physicochemical reactors, condensation hydrocarbon production with dehydrocarbons, etc., can solve the need for metal catalysis, reaction process cycle Long and other problems, to achieve the effect of improving yield, good industrial scale-up potential, and high product yield

Active Publication Date: 2021-06-01
NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved in the present invention is: to overcome the problems of long reaction process period and metal catalysis in the traditional reaction system, and to provide a novel synthesis method of bibenzyl

Method used

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  • Method for continuously preparing bibenzyl by using microchannel reaction device
  • Method for continuously preparing bibenzyl by using microchannel reaction device
  • Method for continuously preparing bibenzyl by using microchannel reaction device

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Dissolve 1 mmol (0.092 g) of toluene and 0.2 mmol (0.074 g) of tetrabutylammonium iodide in 5 mL of dimethyl sulfoxide and 5 mL of water to obtain a homogeneous solution A, which is added to syringe pump a; 2 mmol of TBHP (70% , 0.257g) (tert-butyl hydroperoxide) 5mL dimethyl sulfoxide and 5mL water to obtain a homogeneous solution B, which was added to syringe pump b; the injection flow rates of syringe pumps a and b were both 0.5ml / min; Microchannel reactor reaction volume V=10ml, reaction time 10min; Microchannel reactor internal diameter is 0.5mm; The yield of the product calculated by the method was 82%, and bibenzyl was obtained after separation by column chromatography.

[0028] 1 H NMR (400MHz, Chloroform-d) δ7.22–7.16 (m, 4H), 7.11 (td, J=6.3, 1.5Hz, 6H), 2.83 (s, 4H).

[0029] 13 C NMR (101MHz, Chloroform-d) δ140.73, 127.41, 127.29, 124.87, 36.90.

[0030] HRMS(TOF)m / z[M+H] + Calcd for C 14 h 15 183.1168 found 183.1165.

Embodiment 2

[0032] Dissolve 1 mmol (0.092 g) of toluene and 0.1 mmol (0.037 g) of tetrabutylammonium iodide in 5 mL of dimethyl sulfoxide and 5 mL of water to obtain a homogeneous solution A, which is added to syringe pump a; 2 mmol of TBHP (70% , 0.257g) (tert-butyl hydroperoxide) 5mL dimethyl sulfoxide and 5mL water to obtain a homogeneous solution B, which was added to syringe pump b; the injection flow rates of syringe pumps a and b were both 0.5ml / min; Microchannel reactor reaction volume V=10ml, reaction time 10min; Microchannel reactor internal diameter is 0.5mm; The yield of the product calculated by the method was 70%, and bibenzyl was obtained after separation by column chromatography.

Embodiment 3

[0034] Dissolve 1 mmol (0.092 g) of toluene and 0.3 mmol (0.074 g) of tetrabutylammonium iodide in 5 mL of dimethyl sulfoxide and 5 mL of water to obtain a homogeneous solution A, which is added to syringe pump a; 2 mmol of TBHP (70% , 0.257g) (tert-butyl hydroperoxide) 5mL dimethyl sulfoxide and 5mL water to obtain a homogeneous solution B, which was added to syringe pump b; the injection flow rates of syringe pumps a and b were both 0.5ml / min; Microchannel reactor reaction volume V=10ml, reaction time 10min; Microchannel reactor internal diameter is 0.5mm; The yield of the product calculated by the method was 77%, and bibenzyl was obtained after separation by column chromatography.

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Abstract

The invention provides a method for continuously preparing bibenzyl by using a microchannel reaction device, wherein the method comprises the steps: by taking toluene as a reaction raw material, carrying out continuous reaction in the micro-channel reaction device in the presence of a catalyst, an oxidant and a solvent, and carrying out free radical self-coupling reaction to obtain bibenzyl II. The method provides a novel bibenzyl preparation method; the method has the advantages of simple process operation, safety, high efficiency and mild reaction conditions. The reaction process is shown as a reaction formula defined in the specification.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for continuously preparing bibenzyl by utilizing a microchannel reaction device. Background technique [0002] Bibenzyl compounds are commonly found in many natural products and have potential biological and agricultural activities. Some bibenzyl derivatives are used as raw materials for the synthesis of highly useful drug molecules, thus attracting the attention of many chemists. [0003] At present, the preparation methods of bibenzyl mainly include: (1) self-coupling of benzyl halides to synthesize bibenzyl, which can be found in literature (Org. Lett., 2014, 16, 3756); (2) nickel-catalyzed hydrogenation of olefins For the reaction, please refer to the literature (Chem.Eur.J.2020,26,6113-6117); (3) Noble metal catalyzed aluminum powder reduction of toluene to synthesize bibenzyl, please refer to the literature (Tetrahedron 72 (2016) 6943e6947); (4 ) Tita...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C2/84C07C15/18B01J19/00
CPCC07C2/84B01J19/0093C07C15/18
Inventor 李玉光季栋张锴孟繁荣花加伟郭凯
Owner NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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