Method for preparing benzenediol by catalyzing phenol to hydroxylation with liquid phase transition metal coordination compound salt

A technology for catalyzing phenol hydroxyl groups and transition metals, which is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc. It can solve the problems of large consumption of hydrogen peroxide, high safety performance requirements, and large phenol recovery load. Achieve the effects of inhibiting invalid decomposition, good selectivity and high raw material consumption

Inactive Publication Date: 2013-02-27
DONGHUA UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology describes a process called Hydroxylation reactions where it becomes challenged when controlling or reacts quickly due to difficulties such as back mixing during production. These issues make this type of chemical processes expensive and time consuming. To solve these problem, there have been developed different types of catalysis methods like palladium/platinum composites, platinum on carbon nanotubules, iron shell particles supported on silica gel, zeolite molecular sieve, ion exchange resins, acidic compounds, organometal acids, alkynols, amines, carboxamides, sulfones, nitroso groups, olefms, polycyclic rings containing heteroatoms, phthaleimine structures, quaternary immoniumsulfonates, tertiary alkenals, diketimes, naphtha bases, pyridazoles, thiazolidinediones, boronic ester derivatives, lithography agents, chelating agents, cyclohexene diameters, cyclodienanes, polysaccharides, nucleus sources, metathesis chemistry, and other similar materials used alone or together.

Problems solved by technology

This patents discusses various ways to make certain types of compounds called hydroquinalones from different sources like caffeynols, coumarins, napthrochromene, tanners, chalmers, pyridazenes, chromophores, ammonia nitriles, acids, bases, surfactants, solvents, resists, lubricity agents, adhesive properties, water treatment qualities, and environmental friendliness during processing operations. However, these traditional methods involve expensive starting materials, complicated procedures, long time consumptions, and heavy waste disposals. Therefore, new technologies involving more efficient and cost-effective routes towards producing specific type of hydrocinnoline without generating harmful substances would provide technical benefits over existing ones.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 2,500 grams of phenol, 1,700 milliliters of acetone, and 50 milliliters of iron, cobalt, and nickel acetate catalyst mixtures with a mass concentration of 30% in a 5,000-ml reaction kettle with heating, heat preservation device, cooling device, thermometer, and stirring device. , Stir and mix evenly and heat up to 50°C, then add 800ml of 27.5% hydrogen peroxide dropwise to the reaction solution within 0.5 hours, control the temperature of the reaction solution at 50±5°C during the dropping process, stir for one hour, and the reaction ends. Sampling analysis showed that the conversion rate of hydrogen peroxide was 54.1%, the conversion rate of phenol was 18.3%, the selectivity of hydroquinone was 82.0%, the conversion rate of hydrogen peroxide was 78.3%, and the product catechol / hydroquinone=1.8:1.

Embodiment 2

[0022] Add 2,500 grams of phenol, 1,700 milliliters of acetone, and 60 milliliters of iron, cobalt, and nickel acetate catalyst mixtures with a mass concentration of 20% in a 5,000-ml reaction kettle with heating, heat preservation device, cooling device, thermometer, and stirring device. , Stir and mix evenly and heat up to 50°C, then add 650ml of 35% hydrogen peroxide dropwise to the reaction solution within 1 hour, control the temperature of the reaction solution at 60±5°C during the dropping process, stir for 0.5 hours, and the reaction ends. Sampling analysis showed that the conversion rate of phenol was 17.6%, the selectivity of hydroquinone was 79.6%, the conversion rate of hydrogen peroxide was 52.1%, and the product catechol / hydroquinone=1.7:1.

Embodiment 3

[0024] Add 2500 grams of phenol sequentially in the reaction kettle that 5000ml has heating, insulation device, cooling unit, thermometer, stirring device, 1700 milliliters of acetones, mass concentration is 50 milliliters of iron, cobalt, copper sulfate catalyst mixed solution of 30%, Stir and mix evenly and raise the temperature to 50°C, then add 800 ml of 27.5% hydrogen peroxide dropwise into the reaction solution within 0.5 hours, control the temperature of the reaction solution at 70±5°C during the dropping process, stir the reaction for one hour, and the reaction ends. Sampling analysis showed that the conversion rate of phenol was 18.4%, the selectivity of hydroquinone was 80.7%, the conversion rate of hydrogen peroxide was 75.3%, and the product catechol / hydroquinone=2.2:1.

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PUM

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Abstract

The invention relates to a method for preparing benzenediol by catalyzing phenol to hydroxylation with a liquid phase transition metal coordination compound salt. The method comprises the steps of mixing phenol, solvent and catalyst uniformly, and at the pressure of 1-5 atm, increasing the temperature to 50-90 DEG C; and sectionally dropping hydrogen peroxide in the reaction solution in stages, and stirring the solution for reaction for 0.3-5 h, thus obtaining the benzenediol. The preparation method is low in cost, applicable to medium-low concentration hydrogen peroxide solution and good in selectivity, and the phenol hydroxylation and catalyzing method has high selectivity to benzenediol.

Description

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Claims

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Application Information

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Owner DONGHUA UNIV
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