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A method for synthesizing diphenylmethanol by catalytic hydrogenation of benzophenone

A technology of benzophenone and benzhydryl alcohol, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of hydroxyl compounds, etc., can solve the problems of unrealizable benzyl alcohol process, many wastes, poor quality, etc., and achieve improvement Target product selectivity, faster reaction speed, and less inactivation effects

Active Publication Date: 2021-07-27
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The earliest production process of diphenylmethanol was zinc powder reduction, and then developed into aluminum powder reduction. These two methods have many wastes, low production capacity, poor quality and high energy consumption.
[0006] The catalytic hydrogenation process is a green synthesis process, but when benzophenone is hydrogenated to synthesize benzphenyl alcohol, it is often prone to excessive hydrogenation to form diphenylmethane, and the process of catalytic hydrogenation to synthesize benzphenyl alcohol has not been realized in industry

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] (1) Weigh 10g of mesoporous carbon (particle size is 1000 mesh, specific surface area is 1300m 2 / g, the average pore diameter is 3nm) mixed with 1.5g urea evenly, and treated at 1000°C for 5h under nitrogen atmosphere to obtain 10g nitrogen-doped mesoporous carbon (particle size is 1000 mesh, specific surface area is 1300m 2 / g, the average pore diameter is 3nm, and the nitrogen content is 3.5wt%). Prepare it in 100ml of deionized water to make a slurry at a temperature of 25°C, and slowly add 10ml of H 2 PdCl 4 Solution (the Pd content is 0.05g / ml, namely 0.47mmol / ml), stirred for 0.5h; the pH value of the solution was adjusted to 8 with 10wt% KOH solution, and the temperature was lowered to room temperature, filtered, and the filter residue was washed with deionized water until Neutral to get filter cake;

[0033] (2) The filter cake obtained in step (2) is configured into 80ml slurry at 80°C, 0.9g of 85wt% hydrazine hydrate solution (23.9mmol) is added dropwise, ...

Embodiment 2

[0035] (1) Weigh 10g of mesoporous carbon (with a particle size of 800 mesh and a specific surface area of ​​1500m 2 / g, the average pore diameter is 2nm) mixed with 0.5g urea evenly, and treated at 700°C for 40h under nitrogen atmosphere to obtain 10g nitrogen-doped mesoporous carbon (particle size is 800 mesh, specific surface area is 1500m 2 / g, average pore diameter of 2nm, nitrogen content of 1.2wt%). Prepare it in 100ml of deionized water to make a slurry at a temperature of 100°C, and slowly add 10ml of Na 2 PdCl 4 solution (Pd content is 0.01g / ml, namely 0.094mmol / ml), stirred for 2h; the pH value of the solution was adjusted to 8.5 with 10wt% NaOH solution, and the temperature was lowered to room temperature, filtered, and the filter residue was washed with deionized water to medium sex;

[0036] (2) The filter cake obtained in step (1) is configured into a 50ml slurry at 100°C, 14g of 40wt% formaldehyde (186.7mmol) is added dropwise, stirred for 0.5h, filtered, an...

Embodiment 3

[0038] (1) Weigh 10g of mesoporous carbon (particle size is 100 mesh, specific surface area is 1600m 2 / g, average pore diameter 10nm) and 1.1g urea were mixed evenly, and treated at 1100°C for 25h under argon atmosphere to obtain 10g nitrogen-doped mesoporous carbon (particle size: 100 mesh, specific surface area: 1600m 2 / g, average pore diameter 10nm, nitrogen content 3.0wt%). It was prepared in 100ml of deionized water to make a slurry at a temperature of 40°C, and 4ml of H 2 PdCl 4 Solution (the Pd content is 0.2g / ml, namely 1.88mmol / ml), stirred for 10h; the pH value of the solution was adjusted to 9 with ammonia water, and the temperature was lowered to room temperature, filtered, and the filter residue was washed with deionized water until neutral to obtain a filter cake ;

[0039](2) The filter cake obtained in step (1) is configured into a 100ml slurry at 20°C, 30g of 30wt% formic acid (195.7mmol) is added dropwise, stirred for 50h, filtered, and the filter cake i...

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Abstract

A method for synthesizing diphenylmethanol by catalytic hydrogenation of benzophenone, the method uses a nitrogen-doped mesoporous carbon-supported palladium catalyst, and the nitrogen-doped mesoporous carbon-supported palladium catalyst consists of a nitrogen-doped mesoporous carbon support and metal palladium on the load carrier; the particle size of the nitrogen-doped mesoporous carbon is 100-1000 mesh, and the specific surface area is 600-1800m 2 / g, the average pore diameter is 2.0-20nm, the nitrogen element in the nitrogen-doped mesoporous carbon is directly doped into the carbon skeleton or connected with the carbon material by N-C bonds, and the nitrogen element content is 0.5-10wt%; The loading amount of palladium in the nitrogen-doped mesoporous carbon-supported palladium catalyst is 2-8 wt%. The nitrogen-doped mesoporous carbon-supported palladium catalyst used in the present invention exhibits high catalytic activity, high product selectivity and high stability in the catalytic hydrogenation of benzophenone to synthesize diphenylmethanol.

Description

[0001] (1) Technical field [0002] The invention relates to a method for synthesizing benzphenyl alcohol by catalytic hydrogenation of benzophenone. [0003] (2) Background technology [0004] Diphenylmethanol, also known as α-phenylbenzyl alcohol, is an important organic intermediate, mainly used in the synthesis of diphenhydramine (antihistamine), dimenhydrinate (antihistamine, Chengyunning) , cyclizine (antihistamine), diphenylraline (antihistamine), benzotropine (anticholinergic), modafinil (antidepressant), cinnarizine (vasodilator), Synthesis of drfenib (central nervous system stimulant) and other drugs. [0005] The synthesis of benzhydryl alcohol is mainly obtained through the reduction of benzophenone. The earliest production process of diphenylmethanol was zinc powder reduction, and then developed into aluminum powder reduction. These two methods have many wastes, low production capacity, poor quality and high energy consumption. The current production process is ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C33/24C07C29/145B01J27/24
CPCB01J27/24C07C29/145C07C33/24
Inventor 张群峰李康马磊卢春山丰枫李小年
Owner ZHEJIANG UNIV OF TECH
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