CN1110677A - Synthetic technology of phenylacetic acid - Google Patents

Synthetic technology of phenylacetic acid Download PDF

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Publication number
CN1110677A
CN1110677A CN 94119654 CN94119654A CN1110677A CN 1110677 A CN1110677 A CN 1110677A CN 94119654 CN94119654 CN 94119654 CN 94119654 A CN94119654 A CN 94119654A CN 1110677 A CN1110677 A CN 1110677A
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China
Prior art keywords
toluylic acid
phenylacetamide
vinylbenzene
phenylacetic acid
acid
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CN 94119654
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Chinese (zh)
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潘则林
赵萍
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Individual
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Abstract

The process for synthesizing phenylacetic acid from waste polystyrene or styrene and phenylacetamide features simple technology, easily available raw materials, no pollution and high productivity.

Description

Synthetic technology of phenylacetic acid
The present invention proposes a kind of novel process of toluylic acid synthetic.
Toluylic acid is widely used as the intermediate of medicine, agricultural chemicals and spices etc.The maximum of domestic and international application are penicillin G fermention medium additive, in order to improve the overall yield of penicillin G.In addition, also can make the raw material of plant-growth regulator.Along with the continuous increase of toluylic acid purposes and consumption, supply more and more tight slightlyly, especially China is basically by import.For this reason, the author is doing a large amount of research to the production technique of toluylic acid, has explored a more rational synthesis technique.
The object of the present invention is achieved like this.With the deposed polystyrene is raw material, and depolymerization is a vinylbenzene, again through the phenylacetamide hydrolysis, promptly gets toluylic acid.Its reaction process is as follows:
Figure 941196542_IMG1
This technology has raw material and is easy to get, and production technique is simple, and production process is pollution-free, no violent in toxicity, characteristics such as productive rate height.
Traditional toluylic acid production technique (fine chemistry industry goods handbook, 1988) is to be raw material with toluene, generates benzyl cyanide with chlorine, sodium cyanide (potassium) reaction, after hydrolysis obtains toluylic acid.Its reaction process is as follows:
Figure 941196542_IMG2
The shortcoming of this technology is the prussiate that needs to use severe toxicity in the reaction process, brings harm and pollution for operator and environment.The again medicine production process that are used for of toluylic acid, enrichment and residually all can bring in various degree harm to the mankind make this production method be restricted like this, but this technology is still continued to use in present production both domestic and external more.
In order to overcome above shortcoming, promoting toluylic acid uses more widely, chemist has spent the research that a large amount of energy drops into this technology, explored several method (the Japan special permission 57-35819 of synthesize phenylacetic acid, US4575561, Ger offen2259072,1972-12-02 etc.) all because of in various degree the defective that exists, cause the production of toluylic acid and use to obtain restriction.
Embodiment 1:
(1) cinnamic preparation: a cover water distilling apparatus is installed, add the deposed polystyrene 100g that pulverizes, control liquid temperature is more than 340 ℃, collect the overhead product more than 340 ℃, this overhead product is vinylbenzene, but color is dark, impurity is also more, leave standstill 3h after the vitriol oil that can add 5% volume mixes, with the removal of impurity, then with saturated aqueous common salt and and clear water respectively give a baby a bath on the third day after its birth time, behind the anhydrous sodium sulfate drying, add stopper, BP145-146 ℃ overhead product is collected in air distillation, gets vinylbenzene 89g, yield 89%, n 251.5436.
(2) preparation of phenylacetamide: in a reaction vessel, add vinylbenzene 21.7g, sulphur 37.5g, ammoniacal liquor 50ml, ethanol 30ml, under agitation, temperature of reaction is controlled at 93-95 ℃, reacts 3-4 hour.Reduce to room temperature then, change distillation into, steam liquid, stop heating, be cooled to room temperature, use 500ml water hot extraction 3 times, leave standstill adularescent plate crystal 26.7g after the solution decolouring after the extraction, yield is 94%, M.P.157-158 ℃, and B.P.280-290 ℃ (decomposition), C 8H 9NO(calculated value: C:71.11, H:6.67, N:10.37, O:11.85, measured value: C:71.18, H:6.59, N:10.29, O:11.95), IRv C=01680CM -1, v NH23350CM -1, 3180CM -1, v C6H51580CM -1
(3) preparation of toluylic acid: the phenylacetamide 100g with above-mentioned preparation, add water 150ml, hydrochloric acid 80ml, reflux 2h, being chilled to has precipitation to separate out after room temperature leaves standstill.After the filtration,, get the glossiness crystallization 84g of white plates, yield 84%, M.P.76.5 ℃, B.P.265 ℃ (decomposition), IR v with 1: 2 aqueous ethanolic solution recrystallization C=01710CM -1, v OH3190CM -1, v C6H51586CM -1, C 8H 8O 2(calculated value: C:71.11, H:6.67, N:10.37, O:11.85, measured value: C:71.18, H:6.59, N:10.29, O:11.95).
Embodiment 2: if the deposed polystyrene source is not for a long time, can adopt vinylbenzene is raw material, 2. 3. gets final product with step through embodiment 1 described step, has saved equipment and reactions steps like this.

Claims (4)

1, a kind of toluylic acid synthetic novel process, technology comprises that deposed polystyrene is cracked into vinylbenzene, the preparation and the phenylacetamide of phenylacetamide are hydrolyzed into toluylic acid.Its inventive features is the new synthetic process that proposes a kind of toluylic acid, and deposed polystyrene passes through depolymerization, oxidation, is hydrolyzed into toluylic acid.
2, method according to claim 1, its feature are by the deposed polystyrene thermo-cracking, and temperature is cracked into vinylbenzene more than 340 ℃.
3, method according to claim 1, by vinylbenzene, sulphur, ammoniacal liquor, industrial alcohol is prepared phenylacetamide.
4, method according to claim 1 is prepared toluylic acid by the acidic hydrolysis of phenylacetamide.
CN 94119654 1994-12-15 1994-12-15 Synthetic technology of phenylacetic acid Pending CN1110677A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN 94119654 CN1110677A (en) 1994-12-15 1994-12-15 Synthetic technology of phenylacetic acid

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Application Number Priority Date Filing Date Title
CN 94119654 CN1110677A (en) 1994-12-15 1994-12-15 Synthetic technology of phenylacetic acid

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CN1110677A true CN1110677A (en) 1995-10-25

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CN 94119654 Pending CN1110677A (en) 1994-12-15 1994-12-15 Synthetic technology of phenylacetic acid

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102012224021A1 (en) 2012-05-09 2013-11-14 Lanzhou Institute Of Chemical Physics, Chinese Academy Of Sciences A process for the synthesis of phenylacetic acid by carbonylation of toluene
CN109956862A (en) * 2017-12-22 2019-07-02 四川科瑞德凯华制药有限公司 Sodium phenylacetate crystal form A and its preparation method and application
CN111217698A (en) * 2020-01-20 2020-06-02 伊犁川宁生物技术有限公司 Preparation method of phenylacetic acid reference substance
CN113200841A (en) * 2021-04-21 2021-08-03 嘉兴学院 Novel process for synthesizing racemic naproxen based on Heck coupling

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102012224021A1 (en) 2012-05-09 2013-11-14 Lanzhou Institute Of Chemical Physics, Chinese Academy Of Sciences A process for the synthesis of phenylacetic acid by carbonylation of toluene
US8921591B2 (en) 2012-05-09 2014-12-30 Lanzhou Institute Of Chemical Physics, Chinese Academy Of Sciences Process for synthesizing phenylacetic acid by carbonylation of toluene
CN109956862A (en) * 2017-12-22 2019-07-02 四川科瑞德凯华制药有限公司 Sodium phenylacetate crystal form A and its preparation method and application
CN111217698A (en) * 2020-01-20 2020-06-02 伊犁川宁生物技术有限公司 Preparation method of phenylacetic acid reference substance
CN113200841A (en) * 2021-04-21 2021-08-03 嘉兴学院 Novel process for synthesizing racemic naproxen based on Heck coupling

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