Synthesis method of 2, 2'-dihydroxy-4, 4'-dimethoxybenzophenone

A technology of dimethoxybenzophenone and a synthesis method is applied in the synthesis field of water-soluble ultraviolet absorbers, and can solve the problems of unsafe operation, high investment cost, highly toxic phosgene and the like

Inactive Publication Date: 2012-01-25
HUBEI POLYTECHNIC UNIV
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Problems solved by technology

The traditional method of synthesizing this type of compound is mainly the phosgene method, but phosgene is highly toxic, unsafe to operate, the investment cost in industrialization is too high and because it is a gas, it is not convenient for transportation and storage, which is not conducive to the development of green chemistry. develop

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  • Synthesis method of 2, 2'-dihydroxy-4, 4'-dimethoxybenzophenone
  • Synthesis method of 2, 2'-dihydroxy-4, 4'-dimethoxybenzophenone
  • Synthesis method of 2, 2'-dihydroxy-4, 4'-dimethoxybenzophenone

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Experimental program
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Effect test

Embodiment 1

[0019] Synthesis of 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, the operation steps are as follows:

[0020] The first reaction: Take 13.8g of isophthalic ether and place it in a three-necked flask, add 0.15g of azoisobutyronitrile as a catalyst, add magnets and set up the device; add 30ml of oxalyl chloride to the flask, adjust the temperature and Stirring; Control the temperature at 70-80℃ and react for 1.5 hours; stop the reaction, add water to hydrolyze oxalyl chloride, filter and collect the intermediate product and dry, the intermediate product 2,2'4,4'-tetramethoxybenzophenone infrared The map is like figure 1 , 1 HNMR (400MHz, DMSO-d6) δ: 7.35-7.30 (m, 2H), 6.56 (s, 4H), 3.81 (s, 6H), 3.58 (s, 6H);

[0021] The second step reaction: 30g AlCl 3 And the intermediate product of the first step in the flask, then add 100ml of dichloroethane, stir and control the temperature; control the temperature at 50°C for 2-3 hours; after stopping the reaction, add water for hydrolysis, liqu...

Embodiment 2

[0023] The first step of the reaction; take 13.8g of isophthalic ether and place it in a three-necked flask, add 0.16g of azoisobutyronitrile catalyst, add magnets and set up the device; add 30ml of oxalyl chloride to the flask, adjust the temperature and stir ; Control the temperature at 70-80℃ and react for 1.5 hours; stop the reaction, add water to hydrolyze oxalyl chloride, filter and collect the intermediate product and dry; the intermediate product 2,2'4,4'-tetramethoxybenzophenone infrared spectrum Such as figure 1 ;

[0024] The second step of the reaction: 30g ZnCl 2 And the intermediate product of the first step in the flask, then add 100ml of dichloroethane, stir and control the temperature; control the temperature at about 50℃ for 2-3 hours; after stopping the reaction, add water for hydrolysis, liquid separation, rotary evaporation, By recrystallization, the product 2,2'-dihydroxy-4,4'-dimethoxybenzophenone was obtained, the content detected by HPLC was 99.1%, and th...

Embodiment 3

[0026] The first reaction: Take 13.8g of isophthalic ether and place it in a three-necked flask, add 0.14g of azoisobutyronitrile catalyst, add magnets and set up the device; add 30ml of oxalyl chloride to the flask, adjust the temperature and stir ; Control the temperature at 70-80℃ and react for 1.5 hours; stop the reaction, add water to hydrolyze oxalyl chloride, filter and collect the intermediate product and dry; the intermediate product 2,2'4,4'-tetramethoxybenzophenone infrared spectrum Such as figure 1 ;

[0027] The second step reaction: 30g AlCl 3 Put 100ml of chlorobenzene with the intermediate product of the first step in a flask, stir and control the temperature: control the temperature at 50°C for 2-3 hours; after stopping the reaction, add water for hydrolysis, liquid separation, rotary evaporation and recrystallization, The product 2,2'-dihydroxy-4,4'-dimethoxybenzophenone was obtained, the content detected by HPLC was 99.0%, and the yield was 67%. The infrared s...

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Abstract

The invention relates to a synthesis method of 2, 2'-dihydroxy-4, 4'-dimethoxybenzophenone. The method comprises the following steps: 1) enabling m-dimethoxybenzene and oxalyl chloride to react in the presence of a catalyst at the temperature of 70-80 DEG C for getting an intermediate product 2, 2', 4, 4'-tetramethoxy benzophenone, wherein the weight ratio of the m-dimethoxybenzene to the oxalyl chloride is 1:1-20, the used catalyst is azo isobutyronitrile or benzoyl peroxide, and the using quantity of the catalyst is 0.5%-2% of the weight of the m-dimethoxybenzene; and 2) enabling the obtained intermediate product and Lewis acid to react under the condition of taking an organic reagent as a solvent, wherein the reaction temperature is 50 DEG C and the reaction time is 2-3 hours; and stopping the reaction, adding water for hydrolysis, skimming, performing rotary evaporation and recrystallizing to get the 2, 2'-dihydroxy-4, 4'-dimethoxybenzophenone. The Lewis acid is one of AlCl3, ZnCl2, BF3 and polyphosphoric acid; and the organic reagent is one of dichloroethane, toluene, xylene, nitrobenzene and chlorobenzene. According to the method, the reaction temperature is appropriate, the catalyst is simple and easy to get, the using quantity of the catalyst is low, the environmental pollution is small, and the method is closest to the requirements of green chemistry.

Description

Technical field [0001] The present invention relates to a method for synthesizing water-soluble ultraviolet absorbers, in particular to a method for synthesizing benzophenone ultraviolet absorbing 2,2'-dihydroxy-4,4'-dimethoxybenzophenone. Background technique [0002] Benzophenone compounds are important organic intermediates, which can strongly absorb ultraviolet light and are widely used in daily chemical, pharmaceutical, pesticide, plastic, coating and other fields. The traditional method of synthesizing this type of compound is mainly the phosgene method, but phosgene is highly toxic and unsafe to operate. The investment cost in industrialization is too high. Because it is a gas, it is not convenient for transportation and storage, which is not conducive to green chemistry. development of. The invention provides a synthetic method with less environmental pollution and high product yield. Summary of the invention [0003] The purpose of the present invention is to provide a ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/84C07C45/65
Inventor 王志刚王治国秦少华孙明刚卢志高李琼王千
Owner HUBEI POLYTECHNIC UNIV
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