CN1110677A - Synthetic technology of phenylacetic acid - Google Patents
Synthetic technology of phenylacetic acid Download PDFInfo
- 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
- Authority
- CN
- China
- Prior art keywords
- toluylic acid
- phenylacetamide
- vinylbenzene
- phenylacetic acid
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000005516 engineering process Methods 0.000 title claims abstract description 8
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title abstract description 6
- 229960003424 phenylacetic acid Drugs 0.000 title abstract description 3
- 239000003279 phenylacetic acid Substances 0.000 title abstract description 3
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000004793 Polystyrene Substances 0.000 claims abstract description 7
- 229920002223 polystyrene Polymers 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 238000005336 cracking Methods 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 6
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000002699 waste material Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940056360 penicillin g Drugs 0.000 description 2
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- FJMMZJZTJGGXHX-UHFFFAOYSA-N potassium sodium dicyanide Chemical compound [K+].[C-]#N.[Na+].[C-]#N FJMMZJZTJGGXHX-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 231100000004 severe toxicity Toxicity 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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
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:
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:
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.
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 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 94119654 CN1110677A (en) | 1994-12-15 | 1994-12-15 | Synthetic technology of phenylacetic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1110677A true CN1110677A (en) | 1995-10-25 |
Family
ID=5039312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 94119654 Pending CN1110677A (en) | 1994-12-15 | 1994-12-15 | Synthetic technology of phenylacetic acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1110677A (en) |
Cited By (4)
| 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 |
-
1994
- 1994-12-15 CN CN 94119654 patent/CN1110677A/en active Pending
Cited By (5)
| 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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| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
| WD01 | Invention patent application deemed withdrawn after publication |