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Method for preparing mandelic acid from styrene oxide

A technology for oxidizing styrene and mandelic acid, which is applied in the chemical industry and can solve the problems of large amount of waste water and the like

Inactive Publication Date: 2017-09-15
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction conditions of this method are mild, and the yield can reach more than 76%, but multiple extractions with ether are required in the production process, and the amount of waste water is relatively large

Method used

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  • Method for preparing mandelic acid from styrene oxide
  • Method for preparing mandelic acid from styrene oxide
  • Method for preparing mandelic acid from styrene oxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Get 240.3g (2mol) styrene oxide and join in the mixed solution of 500g ethylene glycol and 200g water, add the NY2 catalyst of 35g (Nanjing Technological University and Yangzi Petrochemical Production), after 140 ℃ of reaction 2 hours, underpressure distillation, concentrate, The catalyst, ethylene glycol and 271.5 g of phenyl glycol were recovered by filtration, with a yield of 98.3%.

[0041] In the sodium hydroxide solution (20%) of 250g (0.81mol) phenylethylene glycol and 430g, add 1.3g charcoal supported Pd-Au catalyst (CRI Catalyst Company, the loading capacity of Pd-Au is 0.5%, Pd / Au =0.3:2), stir evenly, heat to 90°C, feed air (40mL / min) while stirring, after reacting for 6 hours, add hydrochloric acid to adjust the pH value to 7-7.5, filter and recover the catalyst, add 100g Calcium chloride was filtered again to obtain calcium mandelic acid powder, the collected mandelic acid powder was acidified with dilute hydrochloric acid to pH=3-4, concentrated and crysta...

Embodiment 2

[0043] Get 800g (6.66mol) styrene oxide and join in the mixed solution of 800g ethylene glycol and 800g water, add 35g of NY2 and 55g NY3 catalyst, after reacting for 5 hours at 130 DEG C, distill under reduced pressure, concentrate, filter and recover catalyst, ethylene glycol Alcohol and collected phenyl glycol 870.4g, yield 94.6%.

[0044]In the sodium hydroxide solution (40%) of 850g (6.15mol) phenyl ethylene glycol and 1230g, add 85g charcoal supported Pd-Au catalyst (self-made, the load capacity of Pd-Au is 1.5%, Pd / Au=0.3: 1), stir evenly, heat to 95°C, feed air (60mL / min) while stirring, after reacting for 9 hours, add hydrochloric acid to adjust the pH value to 7-7.5, filter and recover the catalyst, add 680g calcium chloride to the filtrate , filtered again to obtain calcium mandelic acid powder, collected mandelic acid powder and acidified with dilute hydrochloric acid to pH = 3-4, concentrated and crystallized to obtain 925 g of mandelic acid, with a yield of 98.86...

Embodiment 3

[0046] Take 300g (2.5mol) of styrene oxide and add it to a mixed solution of 125g ethylene glycol and 375g water, add 125g of NY1 catalyst, react at 60°C for 14 hours, distill under reduced pressure, concentrate, filter and recover catalyst, ethylene glycol and collect 317.8 g of phenyl glycol, yield 92%.

[0047] In the sodium hydroxide solution (20%) of 300g (2.17mol) phenyl glycol and 520g, add 1.5g charcoal supported Pd-Au catalyst (self-made, the loading capacity of Pd-Au is 5%, Pd / Au=0.1 : 2), stir evenly, heat to 95°C, feed air (60mL / min) while stirring, after reacting for 2 hours, add hydrochloric acid to adjust the pH value to 7-7.5, filter and recover the catalyst, add 240g chloride Calcium, filtered again to obtain calcium mandelic acid powder, collected mandelic acid powder and acidified with dilute hydrochloric acid to pH = 3-4, concentrated and crystallized to obtain 325.6 g of mandelic acid, with a yield of 98.6%.

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Abstract

The invention provides a method for preparing mandelic acid from styrene oxide. The preparation method comprises the following steps: preparing phenyl glycol from styrene oxide through hydration under the catalysis of a NY-series catalyst; and introducing air for selective oxidation of mandelic acid from phenyl glycol under the action of an active carbon-loaded Pd-Au catalyst. The preparation method is characterized in that raw materials are mainly composed of styrene oxide, the NY-series catalyst and the active carbon-loaded Pd-Au catalyst. The preparation method for mandelic acid uses cheap and easily available raw materials and is simple in process, mild in conditions and high in product yield and product purity.

Description

technical field [0001] The invention belongs to the field of chemical industry and relates to a method for preparing mandelic acid from styrene oxide. technical background [0002] Mandelic acid, also known as mandelic acid, chemical name 1-hydroxyphenylacetic acid. 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 produce pesticides such as herbicides phenazine and phenazine; mandelic acid is also an important intermediate for the preparation of heterocyclic disperse dye 356. [0003] At present, there are three main methods for the synthesis of mandelic acid in industry. [0004] 1) Benzaldehyde Oxidation Method In this method, hydroxyphenylacetonitrile is first ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/265C07C59/50C07C29/10C07C33/20
CPCC07C29/10C07C51/265C07C59/50C07C33/20
Inventor 孙戒王海英
Owner NANJING UNIV OF TECH
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