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Synthetic method for ultraviolet absorbent namely 4,4'-dihexyloxybenzophenone

A technology for the chemistry of dihexyloxybenzophenone and dihexyloxybenzophenone is applied in the field of synthesis of ultraviolet light absorbers to achieve the beneficial effects of less three wastes, suppression of side reactions, and environmental and producer labor protection.

Active Publication Date: 2017-09-05
RUDONG JINKANGTAI CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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There are few reports on the synthesis of the title compound

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  • Synthetic method for ultraviolet absorbent namely 4,4'-dihexyloxybenzophenone
  • Synthetic method for ultraviolet absorbent namely 4,4'-dihexyloxybenzophenone

Examples

Experimental program
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Embodiment 1

[0019] (1) Add 51.8g (0.375mol) of p-hydroxybenzoic acid to 100ml of cyclohexane, add dropwise 35.30g (0.45mol) of acetyl chloride at 30-35°C, and keep the reaction at 35-40°C for 2 hours after dropping. Atmospheric pressure distillation recovered excess acetyl chloride and solvent cyclohexane, and ethanol was added for recrystallization to obtain 65.5 g of p-acetoxybenzoic acid, with a yield of 97%;

[0020] (2) Add 65.5g (0.36mol) of p-acetoxybenzoic acid, 35.8g (0.38mol) of phenol, phosphorus oxychloride 66 (0.43mol), and 98g (0.72mol) of zinc chloride into 180ml of dichlorobenzene , keep the reaction at 65-70°C for 2 hours, cool down to 30°C, pour it into 300ml of ice water in a trickle, let stand to remove the water, then wash with water until neutral; add 90ml of 28% ammonia water dropwise into the organic phase at 10-15°C , dripping and reacting at room temperature for 3 hours, standing to remove water, adding water and azeotropically distilling off the solvent dichloro...

Embodiment 2

[0024] (1) Add 51.8g (0.375mol) of p-hydroxybenzoic acid to 100ml of cyclohexane, add dropwise 36.10g (0.46mol) of acetyl chloride at 30-35°C, and keep the reaction at 35-40°C for 2 hours after dropping. Atmospheric distillation recovers excess acetyl chloride and solvent cyclohexane, and ethanol is added for recrystallization to obtain 65.4 g of p-acetoxybenzoic acid with a yield of 97%;

[0025] (2) Add 65.4g (0.36mol) of p-acetoxybenzoic acid, 37.7g (0.4mol) of phenol, 67.5g (0.44mol) of phosphorus oxychloride, and 98g (0.72mol) of zinc chloride into 180ml of dichlorobenzene , keep the reaction at 65-70°C for 2 hours, cool down to 30°C, pour it into 300ml of ice water in a trickle, let stand to remove the water, then wash with water until neutral; add 90ml of 28% ammonia water dropwise into the organic phase at 10-15°C After dripping and reacting at room temperature for 3 hours, let it stand to remove water, add water again and azeotropically distill off the solvent dichlor...

Embodiment 3

[0029] (1) Add 51.8g (0.375mol) of p-hydroxybenzoic acid to 100ml of cyclohexane, add dropwise 34.50g (0.44mol) of acetyl chloride at 30-35°C, and keep the reaction at 35-40°C for 2 hours after dropping. Atmospheric pressure distillation recovered excess acetyl chloride and solvent cyclohexane, and ethanol was added for recrystallization to obtain 65.5 g of p-acetoxybenzoic acid, with a yield of 97%;

[0030] (2) Add 65.5g (0.36mol) of p-acetoxybenzoic acid, 35.8g (0.39mol) of phenol, phosphorus oxychloride 66 (0.43mol), and 104g (0.73mol) of zinc chloride into 180ml of dichlorobenzene , keep the reaction at 65-70°C for 2 hours, cool down to 30°C, pour it into 300ml of ice water in a trickle, let it stand to remove the water, and then wash it until neutral; add 120ml of 28% ammonia water to the organic phase at 10-15°C , dripping and reacting at room temperature for 3 hours, standing to remove water, adding water and azeotropically distilling off the solvent dichlorobenzene, f...

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Abstract

The invention discloses a synthetic method for an ultraviolet absorbent namely 4,4'-dihexyloxybenzophenone. The method comprises the following steps: with p-hydroxybenzoic acid as a starting material, carrying out acetylation to protect hydroxy; carrying out a Fredel-Crafts reaction of p-acetoxybenzoic acid and phenol under the catalysis of zinc chloride and phosphorus oxychloride so as to synthesize an intermediate namely phenyl p-hydroxybenzoate; then carrying out deacetylation to remove the protective group, and carrying out Fries rearrangement so as to prepare an intermediate namely 4,4-dihydroxybenzophenone; and forming a salt with 4,4-dihydroxybenzophenone and potassium carbonate, and carrying out a Williamson reaction of 1-bromohexane and the potassium salt of 4,4-dihydroxybenzophenone through catalysis of tetrabutylammonium bromide so as to synthesize the 4,4'-dihexyloxybenzophenone. The synthetic method provided by the invention has the advantages of mild reaction conditions, normal pressure, medium and low temperature, stable quality control, high raw material conversion rate, effective inhibition of side reactions, fewer three wastes, light pollution, and facilitation of protecting the environment and labor of a producer.

Description

technical field [0001] The invention relates to a synthesis method of an ultraviolet absorber, in particular to a synthesis method of an ultraviolet absorber 4,4'-dioxyloxybenzophenone. Background technique [0002] Ultraviolet absorbers (benzophenone derivatives) are widely used functional additives for polymer materials, which can strongly absorb ultraviolet rays, and are also widely used in daily chemical, pharmaceutical, pesticide, plastic, coating and other fields. As the destruction of the earth's ozone layer becomes more and more serious, the radiation of the sun's ultraviolet rays on the earth becomes more and more intense. Therefore, ultraviolet absorbers are one of the indispensable functional additives for various polymer materials and skin protection products. In recent years, the demand for high-quality ultraviolet absorbers has been increasing at home and abroad. Internationally, such as: containing sulfonic acid, amine-based heterobenzodiazodiphenyl ultraviol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/14C07C69/157C07C67/287C07C69/94C07C67/31C07C45/54C07C49/83C07C45/64C07C49/84C08K5/07
CPCC07C45/54C07C45/64C07C67/14C07C67/287C07C67/31C08K5/07C07C69/157C07C69/94C07C49/83C07C49/84Y02P20/55
Inventor 郭徐良万学明
Owner RUDONG JINKANGTAI CHEM CO LTD
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