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Preparation method of 2,6-diphenyl phenol

A diphenylphenol, tubular technology, applied in the preparation of organic compounds, chemical instruments and methods, bulk chemical production, etc., can solve the problems of difficult separation of products and catalysts, low mechanical strength of catalysts, difficult control of operating conditions, etc. , to achieve the effect of high mechanical strength, easy to control, and not easy to coke

Active Publication Date: 2012-05-16
718TH RES INST OF CHINA SHIPBUILDING INDAL CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The advantage of this process is that the raw material cyclohexanone is economical, less environmental pollution, less process steps, and suitable for large-scale industrial production; the disadvantage is that after the first step cyclohexanone is self-condensed under the action of a catalyst to obtain trimer ketone, the second step In the second step, Pd / C catalyst is added to the trimerone container, and the dehydrogenation reaction is carried out at 260-290 ° C to prepare 2,6-diphenylphenol. The operating conditions are not easy to control, the continuity is poor, the mechanical strength of the catalyst is low, and it is easy to coke. Product and catalyst are difficult to separate

Method used

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  • Preparation method of 2,6-diphenyl phenol
  • Preparation method of 2,6-diphenyl phenol
  • Preparation method of 2,6-diphenyl phenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] With reference to the method described in the article "Study on the Synthesis of 2,6-Diphenylphenol Intermediates" published on the 30th to 34th pages of the first phase of "Ship Defense Chemical" in 2009 by Xu Donghai, etc., using cyclohexanone as Raw materials for synthesis of tripolyketone. Connect a condenser to a 250mL three-neck flask, add 98.2g cyclohexanone and 40mL toluene, heat to 150°C, add 0.28g potassium hydroxide as a catalyst, and reflux at 150°C for 2.5 hours. After the reaction stops, use the reaction product 10% hydrochloric acid solution neutralization, separation of water layer, drying, vacuum distillation, collecting fractions at different temperatures, the mass fraction of the product obtained is 12.6% cyclohexanone, 35.6% dimer ketone, 50.6% trimer ketone, 1.2 % high boilers.

Embodiment 2

[0024] A tubular fixed-bed reactor with an aspect ratio of 10:1 is placed in a heating furnace, and the tubular fixed-bed reactor is filled with 5% Pd / Al 2 o 3 Catalyst, the reaction temperature is controlled at 290 ° C, protected by nitrogen, and after the temperature is stable, the trimerketone prepared in Example 1 is input from the lower port of the tubular fixed bed reactor with a pump, and the liquid hourly space velocity is 2.9h -1 , relying on the pressure of the pump, the trimeric ketone flows out from the upper port of the tubular fixed-bed reactor after being reacted by the catalyst, and collects the reactant flowing out; adopts the external standard method, analyzes the reactant with HPLC, and the analysis condition is: column Temperature is 30 ℃, mobile phase is 80% methanol aqueous solution, and mobile phase flow rate is 0.5ml / min, and analysis result is as follows: Based on the mass of described reactant as 100%, wherein tripolyketone is 6.9%, 2-cyclohexyl -6-p...

Embodiment 3

[0026] A tubular fixed-bed reactor with an aspect ratio of 5:1 is placed in a heating furnace, and alumina is loaded into the tubular fixed-bed reactor as a catalyst with a carrier palladium content of 5%, the reaction temperature is controlled at 290 ° C, and nitrogen gas Protection, after the temperature is stable, the trimerketone prepared in Example 1 is input from the lower port of the tubular fixed bed reactor with a pump, and the liquid hourly space velocity is 2.9h -1 , relying on the pressure of the pump, the trimeric ketone flows out from the upper port of the tubular fixed-bed reactor after being reacted by the catalyst, and collects the reactant flowing out; adopts the external standard method, analyzes the reactant with HPLC, and the analysis condition is: column Temperature is 30 ℃, mobile phase is 80% methanol aqueous solution, and mobile phase flow rate is 0.5ml / min, and analysis result is as follows: The mass of described reactant is 100%, and wherein, trimeron...

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Abstract

The invention relates to a preparation method of 2,6-diphenyl phenol. The preparation method is characterized in that 2,6-diphenyl phenol is prepared in a tubular fixed bed reactor aiming at overcoming the defects that operating conditions are difficult to control, continuity is poor, mechanical strength of a catalyst is low, the catalyst is easy to coke and products and the catalyst are difficult to separate in the prior art; the catalyst is loaded, temperature is controlled to be 250-300 DEG C, shielding gas is introduced to realize gas shielding, trimeric ketone obtained through cyclohexanone self-condensation reaction is added into the tubular fixed bed reactor, liquid hourly space velocity is 0.1-10 / h, the trimeric ketone flows out from the tubular fixed bed reactor after reaction is carried out in the presence of the catalyst, reaction product flowed out is collected, the reaction product is recrystallized in solvent, and vacuum filtering and drying are carried out, thus 2,6-diphenyl phenol is obtained. The preparation method provided by the invention has the advantages that raw materials are economic, continuous operation can be realized, the preparation method is convenient to control, the mechanical strength of the catalyst is high, the catalyst is difficult to coke and can be completely separated from the product, per-pass conversion of the trimeric ketone is high, and yield of the target product is high.

Description

technical field [0001] The present invention relates to a kind of preparation method of 2,6-diphenylphenol, specifically, relate to a kind of preparation method of the 2,6-diphenylphenol that takes cyclohexanone self-condensation trimer ketone as raw material . Background technique [0002] 2,6-diphenylphenol (2,6-diphenylphenol, referred to as DPP) is an important chemical raw material, the appearance is white crystalline powder, the melting point is 101 ℃ ~ 103 ℃, slightly soluble in water, easily soluble in methanol, Organic solvents such as ethanol, acetone, benzene, dichlorobenzene, and trichloroethylene, and alkaline solutions. It is widely used in the fields of dyes, insecticides, narcotics, adsorption materials, special engineering plastics, insulating materials and antioxidants. With the continuous expansion of the use of 2,6-diphenylphenol in recent years, the demand has increased rapidly, and the development prospect is extremely broad. [0003] In recent decad...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/15C07C37/07
CPCY02P20/52
Inventor 陈欢张洪彬许东海
Owner 718TH RES INST OF CHINA SHIPBUILDING INDAL CORP
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