Method for synthesizing mandelic acid

A technology of mandelic acid and mixed solution is applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylates, etc., can solve the problems of backward adopting methods, large environmental pollution, high price, etc., and achieves short production process flow, The effect of low waste discharge and low toxicity

Active Publication Date: 2021-02-05
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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  • Method for synthesizing mandelic acid
  • Method for synthesizing mandelic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0033]S1. Add styrene, ethylene glycol dimethyl ether and water into a three-necked flask, add trichloroisocyanuric acid, heat up the reaction to the end, 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 under reduced pressure to obtain 2,2-dichloroacetophenone.

[0034]S2. Under stirring conditions, hydrolyze 2,2-dichloroacetophenone in a sodium hydroxide solution, adjust the pH to 2-3 with hydrochloric acid, and cool to precipitate 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 under ice bath conditions, heat to 70°C, continue to stir and react To the end of the reaction. The reaction solution was cooled to room temperature, filtered, the filtrate was added, extracted with dichloromethane, filtered, and spin-dried to obtain 1.31 g of 2,2-dichloroacetophenone. The white solid cyanuric acid was filtered out and recovered, with a recovery rate of 95%.

[0037]S2. Take 10ml of sodium hydroxide solution with a mass fraction of 10%, and slowly add the crude product in step (2) dropwise. The temperature is controlled at 50°C and the temperature is kept for one hour. Then the pH is adjusted to 1-2 with hydrochloric acid, and then added 0.1g of activated carbon faded, and after keeping it for one hour, 1.06g of crystals precipitated.

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 under ice bath conditions, heat to 70°C, continue to stir and react To the end of the reaction. The reaction solution was cooled to room temperature, filtered, the filtrate was added, extracted with dichloromethane, filtered, and spin-dried to obtain 1.59 g of 2,2-dichloroacetophenone. The white solid cyanuric acid was filtered out and recovered, with a recovery rate of 95%.

[0040]S2. Take 10ml of sodium hydroxide solution with a mass fraction of 10%, and slowly add the crude product in step (1) dropwise. The temperature is controlled at 50°C and kept for one hour. Then the pH is adjusted to 1-2 with hydrochloric acid and added 0.1g of activated carbon faded, and after holding for one hour, 1.27g of crystals precipitated.

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Abstract

The invention relates to the technical field of compound preparation, and provides a method for synthesizing mandelic acid, which comprises the following steps: by using styrene as a basic raw material, trichloroisocyanuric acid as a chlorinating agent and a mixed solution of ethylene glycol dimethyl ether, methanol, ethanol and water as a solvent, synthesizing mandelic acid by using the strong oxidizing property and chlorinating property of trichloroisocyanuric acid; directly oxidizing styrene in one step and chlorinating to obtain 2, 2-dichloroacetophenone, and hydrolyzing 2, 2-dichloroacetophenone to obtain mandelic acid; and reacting trichloroisocyanuric acid to generate cyanuric acid for recycling. Compared with the prior art, the invention has the following remarkable advantages: (1)styrene with low price, low toxicity and no irritation is used as a raw material; and (2) trichloroisocyanuric acid reacts to generate cyanuric acid, and trichloroisocyanuric acid can be generated through chlorination for recycling; and (3) the production process is short in flow, less in waste discharge, environment-friendly and green.

Description

Technical field[0001]The invention relates to the technical field of compound preparation, in particular to a method for synthesizing mandelic acid.Background technique[0002]Mandelic acid, whose scientific name is α-hydroxyphenylacetic acid, is also called phenylglycolic acid or mandelic acid. Its chemical formula is C8H8O3, its molecular weight is 152.15, and its melting point is 118-121℃. It is easily soluble in water and ethanol.[0003]Structural formula of mandelic acid:[0004][0005]Mandelic acid is mainly used in many fields such as dyes, medicines, and cosmetics. Mandelic acid is an important intermediate widely used in medicine, pesticides, dyes and cosmetics. In medicine, mandelic acid can be used to produce urinary tract fungicide drugs urotropine mandelic acid, peripheral vasodilator cyclic mandelate, eye drops hydroxybenzazole, etc. It can also be used to produce gustyrol esters and acetyl groups. Mandelic chloride, pemoline, etc. It can further generate acetophenone acid t...

Claims

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Application Information

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Patent Type & Authority Applications(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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