A method for preparing mandelic acid from trichloroisocyanuric acid chlorostyrene

A technology of trichloroisocyanuric acid chlorostyrene and trichloroisocyanuric acid, which is applied in the direction of carboxylate preparation, carbon-based compound preparation, chemical instruments and methods, etc., can solve the problem of high price, outdated methods and environmental pollution Large and other problems, to achieve the effect of less waste discharge and short production process

Active Publication Date: 2021-12-31
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] At present, domestic reports on the synthesis of mandelic acid mainly use benzaldehyde and acetophenone as raw materials, which are expensive, and the methods used are relatively backward and cause great environmental pollution.

Method used

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  • A method for preparing mandelic acid from trichloroisocyanuric acid chlorostyrene
  • A method for preparing mandelic acid from trichloroisocyanuric acid chlorostyrene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] S1. Add styrene, ethylene glycol dimethyl ether and water into a three-necked flask, add trichloroisocyanuric acid, heat up to complete the reaction, cool the reaction solution to room temperature, filter, and recover the filtered white solid for use. The filtrate was extracted with dichloromethane, the organic layer was collected, and the solvent was evaporated to dryness under reduced pressure to obtain 2,2-dichloroacetophenone.

[0034] S2. Hydrolyze 2,2-dichloroacetophenone in a sodium hydroxide solution under stirring, adjust the pH to 2-3 with hydrochloric acid, and cool to precipitate the product mandelic acid.

Embodiment 2

[0036] S1. Dissolve 1.04g (10mmol) of styrene in a mixed solution of ethylene glycol dimethyl ether and water, slowly add 1.3eq of trichloroisocyanuric acid in an ice bath, heat up to 70°C, and continue to stir the reaction to the end of the reaction. The reaction solution was cooled to room temperature, filtered, added to the filtrate, extracted with dichloromethane, filtered, and spin-dried to obtain 1.31 g of 2,2-dichloroacetophenone, and the white solid cyanuric acid was recovered by filtration, with a recovery rate of 95%.

[0037] S2, take 10ml of sodium hydroxide solution with a mass fraction of 10%, slowly add the crude product in the step (2) dropwise, the temperature is controlled at 50°C, keep it warm for one hour, then adjust the pH to 1-2 with hydrochloric acid, add 0.1g of activated carbon fades, heat preservation for one hour, and 1.06g of crystals precipitate out.

Embodiment 3

[0039] S1. Dissolve 1.04g (10mmol) of styrene in a mixed solution of ethylene glycol dimethyl ether and water, slowly add 1.5eq of trichloroisocyanuric acid in an ice bath, heat up to 70°C, and continue to stir the reaction to the end of the reaction. The reaction solution was cooled to room temperature, filtered, added to the filtrate, extracted with dichloromethane, filtered, and spin-dried to obtain 1.59 g of 2,2-dichloroacetophenone, and the white solid cyanuric acid was recovered by filtration, with a recovery rate of 95%.

[0040] S2, take 10ml of sodium hydroxide solution with a mass fraction of 10%, slowly add the crude product in the step (1) dropwise, the temperature is controlled at 50°C, keep it warm for one hour, then adjust the pH to 1-2 with hydrochloric acid, add 0.1g of activated carbon fades, heat preservation for one hour, and 1.27g of crystals precipitate out.

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Abstract

The invention relates to the technical field of compound preparation, and provides a method for preparing mandelic acid from trichloroisocyanuric acid chlorinated styrene. The invention uses styrene as a basic raw material, trichloroisocyanuric acid as a chlorination agent, and ethylene glycol A mixed solution of alcohol dimethyl ether, methanol, ethanol, and water is used as a solvent, and the strong oxidizing and chlorinating properties of trichloroisocyanuric acid are used to directly oxidize and chlorinate styrene into 2,2-dichloroacetophenone in one step , and then hydrolyze 2,2-dichloroacetophenone to obtain mandelic acid. After the reaction of trichloroisocyanuric acid, cyanuric acid is generated to be recovered. Compared with the prior art, the present invention has significant advantages: (1) adopts cheap, less toxic and non-irritating styrene as raw material. (2) Trichloroisocyanuric acid reacts to generate cyanuric acid, which can be chlorinated to generate trichloroisocyanuric acid for recycling. (3) The production process is short, the waste discharge is less, and it is environmentally friendly and green.

Description

technical field [0001] The invention relates to the technical field of compound preparation, in particular to a method for preparing mandelic acid from chlorostyrene trichloroisocyanurate. Background technique [0002] Mandelic acid, whose scientific name is α-hydroxyphenylacetic acid, also known as phenylglycolic acid or mandelic acid, has a chemical formula of C8H8O3, a molecular weight of 152.15, and a melting point of 118-121°C. It is easily soluble in water and ethanol. [0003] Mandelic acid structural formula: [0004] [0005] Mandelic acid is mainly used in dyes, medicine, cosmetics and other fields. Mandelic acid is an important intermediate widely used in medicine, pesticides, dyes and cosmetics. In medicine, mandelic acid can be used to produce urotropine mandelic acid, a urinary tract bactericide, cyclomandelate, a peripheral vasodilator, hydroxybenzazole, etc. Mandeloyl chloride, pemoline, etc. It can also further generate acetophenone acid, and then pro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/00C07C59/50C07C45/00C07C45/28C07C45/63C07C49/80
CPCC07C51/00C07C45/00C07C45/28C07C45/63C07C59/50C07C49/80
Inventor 杨运旭申奥
Owner UNIV OF SCI & TECH BEIJING
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