CN107698433A - The preparation method of phenylacetic acid - Google Patents
The preparation method of phenylacetic acid Download PDFInfo
- Publication number
- CN107698433A CN107698433A CN201710818270.7A CN201710818270A CN107698433A CN 107698433 A CN107698433 A CN 107698433A CN 201710818270 A CN201710818270 A CN 201710818270A CN 107698433 A CN107698433 A CN 107698433A
- Authority
- CN
- China
- Prior art keywords
- phenylacetic acid
- preparation
- sodium
- reaction
- obtains
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention proposes a kind of preparation method of phenylacetic acid, comprises the following steps：1) benzyl chloride and Cymag are added in reactor, are warming up to 60~120 DEG C of progress cyanogenations, the reaction time is 2~12h, obtains water-oil phase, and it is at the middle and upper levels benzene acetonitrile crude product, and lower floor is waste water layer；2) add highly basic into the crude product of benzene acetonitrile or strong base solution is hydrolyzed, hydrolysis temperature is 40~120 DEG C, control reaction end PH=8~13, obtains sodium phenylacetate and ammonia, wherein ammonia enters absorption system；3) add sulfuric acid in the sodium phenylacetate obtained to step 2) or hydrochloric acid is acidified, reaction temperature is 20~80 DEG C, is defined by reaction end PH=1~2, and reaction terminates rear product crystallization and separated out, and carries out separation of solid and liquid and obtains phenylacetic acid.The preparation method can fast and effeciently prepare phenylacetic acid, and cost ineffective benefit is good.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of preparation method of phenylacetic acid.
Background technology
Phenylacetic acid is a kind of important organic compound, because it has the typical reaction of carboxyl, methylene hydrogen and phenyl ring,
A variety of intermediates can be generated, thus it is extensive in sector applications such as medicine, spices, agricultural chemicals, especially in penicillin Nacl
There is huge demand in production.
At present, up to tens of kinds of the synthetic route of phenylacetic acid, wherein common are：Sodium cyanide method, styrene method, acetophenone
Method and benzylic halides carbonyl process.Chinese patent application 201611110169.8 provides a kind of bioanalysis and prepares phenylacetic acid
Method, it comprises the following steps：Benzene acetonitrile is divided into some batches, the volume per batch is equal, at regular intervals will be a collection of
Secondary benzene acetonitrile is added in conversion fluid, is then reacted under conditions of pH is 6.0~9.0 and temperature is 20~40 DEG C, is treated last consignment of
The conversion ratio of secondary benzene acetonitrile reaches adds next batch afterwards to a certain degree, treats that the conversion ratio of the benzene acetonitrile of last batch reaches
Terminating reaction after to a certain degree, obtains phenylacetic acid；The conversion fluid is included containing the E.coli works for secreting MG nitrilases
Journey bacterium.The preparation technology needs to cause using bioengineered strain that its cost is higher, and operating procedure is harsher, to staff training
It is it is required that high.
The content of the invention
The present invention proposes a kind of preparation method of phenylacetic acid, and the preparation method can fast and effeciently prepare phenylacetic acid,
And cost ineffective benefit is good.
The technical proposal of the invention is realized in this way：
A kind of preparation method of phenylacetic acid, comprises the following steps：
1) benzyl chloride and Cymag are added in reactor, are warming up to 60~120 DEG C of progress cyanogenations, reaction time
For 2~12h, water-oil phase is obtained, it is at the middle and upper levels benzene acetonitrile crude product, and lower floor is waste water layer；
2) add highly basic into the crude product of benzene acetonitrile or strong base solution is hydrolyzed, hydrolysis temperature is 40~120 DEG C, control
Reaction end PH=8~13 processed, sodium phenylacetate and ammonia are obtained, wherein ammonia enters absorption system；
3) add sulfuric acid in the sodium phenylacetate obtained to step 2) or hydrochloric acid is acidified, reaction temperature is 20~80
DEG C, it is defined by reaction end PH=1~2, reaction terminates rear product crystallization and separated out, and carries out separation of solid and liquid and obtains phenylacetic acid.
Preferably, the mol ratio of the benzyl chloride in the step 1) and Cymag is 0.9~1.2:1.
Preferably, the highly basic is sodium hydroxide, potassium hydroxide, potassium carbonate or sodium carbonate, and the strong base solution is hydrogen
Sodium hydroxide solution, potassium hydroxide solution, solution of potassium carbonate or sodium carbonate liquor.
Preferably, the concentration of the sodium hydroxide in the sodium hydroxide solution is 32wt%.
Preferably, the mol ratio of benzene acetonitrile and highly basic is 0.8~1.1:1.
Preferably, the mass concentration of the sulfuric acid is 30~98%, and the mass concentration of the hydrochloric acid is 30%.
Beneficial effects of the present invention：
1st, after the phenylacetic acid drying that the present invention is prepared, phenylacetic acid content >=99% is measured.
2nd, preparation method of the present invention can fast and effeciently prepare phenylacetic acid, and cost ineffective benefit is good.
Embodiment
Embodiment 1
A kind of preparation method of phenylacetic acid, comprises the following steps：
1) by benzyl chloride and Cymag, (mol ratio of benzyl chloride and Cymag is 1.1:1) it is added in reactor, heats up
To 100 DEG C of progress cyanogenations, reaction time 8h, water-oil phase is obtained, it is at the middle and upper levels benzene acetonitrile crude product, and lower floor is waste water
Layer；
2) 32wt% sodium hydroxide solutions are added into the crude product of benzene acetonitrile, and (mol ratio of benzene acetonitrile and sodium hydroxide is
0.9:1) it is hydrolyzed, hydrolysis temperature is 90 DEG C, controls reaction end PH=10, obtains sodium phenylacetate and ammonia, wherein ammonia
Into absorption system；
3) add the hydrochloric acid that mass concentration is 30% in the sodium phenylacetate obtained to step 2) to be acidified, reaction temperature is
60 DEG C, it is defined by reaction end PH=1.5, reaction terminates rear product crystallization and separated out, and carries out separation of solid and liquid and obtains phenylacetic acid, enters one
Step drying obtains dried phenylacetic acid.
Embodiment 2
A kind of preparation method of phenylacetic acid, comprises the following steps：
1) by benzyl chloride and Cymag, (mol ratio of benzyl chloride and Cymag is 1.2:1) it is added in reactor, heats up
To 120 DEG C of progress cyanogenations, reaction time 2h, water-oil phase is obtained, it is at the middle and upper levels benzene acetonitrile crude product, and lower floor is waste water
Layer；
2) 32wt% potassium hydroxide solutions are added into the crude product of benzene acetonitrile, and (mol ratio of benzene acetonitrile and potassium hydroxide is
1.1:1) it is hydrolyzed, hydrolysis temperature is 100 DEG C, controls reaction end PH=8, obtains sodium phenylacetate and ammonia, wherein ammonia
Into absorption system；
3) add the sulfuric acid that mass concentration is 30% in the sodium phenylacetate obtained to step 2) to be acidified, reaction temperature is
50 DEG C, it is defined by reaction end PH=1, reaction terminates rear product crystallization and separated out, and carries out separation of solid and liquid and obtains phenylacetic acid, further
Drying obtains dried phenylacetic acid.
Embodiment 3
A kind of preparation method of phenylacetic acid, comprises the following steps：
1) by benzyl chloride and Cymag, (mol ratio of benzyl chloride and Cymag is 0.9:1) it is added in reactor, heats up
To 60 DEG C of progress cyanogenations, reaction time 12h, water-oil phase is obtained, it is at the middle and upper levels benzene acetonitrile crude product, and lower floor is waste water
Layer；
2) 32wt% potassium hydroxide solutions are added into the crude product of benzene acetonitrile, and (mol ratio of benzene acetonitrile and potassium hydroxide is
0.8:1) it is hydrolyzed, hydrolysis temperature is 40 DEG C, controls reaction end PH=13, obtains sodium phenylacetate and ammonia, wherein ammonia
Into absorption system；
3) add the sulfuric acid that mass concentration is 60% in the sodium phenylacetate obtained to step 2) to be acidified, reaction temperature is
80 DEG C, it is defined by reaction end PH=2, reaction terminates rear product crystallization and separated out, and carries out separation of solid and liquid and obtains phenylacetic acid.
Embodiment 4
A kind of preparation method of phenylacetic acid, comprises the following steps：
1) benzyl chloride and Cymag are added in reactor, are warming up to 80 DEG C of progress cyanogenations, reaction time 6h,
Water-oil phase is obtained, it is at the middle and upper levels benzene acetonitrile crude product, and lower floor is waste water layer；
2) 32wt% sodium hydroxide solutions are added into the crude product of benzene acetonitrile, and (mol ratio of benzene acetonitrile and sodium hydroxide is 1:
1) it is hydrolyzed, hydrolysis temperature is 60 DEG C, controls reaction end PH=12, obtains sodium phenylacetate and ammonia, and wherein ammonia enters
Absorption system；
3) add the hydrochloric acid that mass concentration is 15% in the sodium phenylacetate obtained to step 2) to be acidified, reaction temperature is
20 DEG C, it is defined by reaction end PH=2, reaction terminates rear product crystallization and separated out, and carries out separation of solid and liquid and obtains phenylacetic acid, further
Drying obtains dried phenylacetic acid.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
God any modification, equivalent substitution and improvements made etc., should be included in the scope of the protection with principle.
Claims (6)
1. a kind of preparation method of phenylacetic acid, it is characterised in that comprise the following steps：
1) benzyl chloride and Cymag are added in reactor, are warming up to 60~120 DEG C of progress cyanogenations, reaction time 2
~12h, obtains water-oil phase, and it is at the middle and upper levels benzene acetonitrile crude product, and lower floor is waste water layer；
2) add highly basic into the crude product of benzene acetonitrile or strong base solution is hydrolyzed, hydrolysis temperature is 40~120 DEG C, and control is anti-
Terminal PH=8~13 are answered, obtain sodium phenylacetate and ammonia, wherein ammonia enters absorption system；
3) adding sulfuric acid in the sodium phenylacetate obtained to step 2) or hydrochloric acid is acidified, reaction temperature is 20~80 DEG C, with
Reaction end PH=1~2 are defined, and reaction terminates rear product crystallization and separated out, and carries out separation of solid and liquid and obtains phenylacetic acid.
2. the preparation method of phenylacetic acid according to claim 1, it is characterised in that benzyl chloride and cyanogen in the step 1)
The mol ratio for changing sodium is 0.9~1.2:1.
3. the preparation method of phenylacetic acid according to claim 1, it is characterised in that the highly basic is sodium hydroxide, hydrogen-oxygen
Change potassium, potassium carbonate or sodium carbonate, the strong base solution be sodium hydroxide solution, potassium hydroxide solution, solution of potassium carbonate or
Sodium carbonate liquor.
4. the preparation method of phenylacetic acid according to claim 3, it is characterised in that the hydrogen in the sodium hydroxide solution
The concentration of sodium oxide molybdena is 32wt%.
5. the preparation method of phenylacetic acid according to claim 1, it is characterised in that the mol ratio of benzene acetonitrile and highly basic is
0.8~1.1:1.
6. the preparation method of phenylacetic acid according to claim 1, it is characterised in that the mass concentration of the sulfuric acid be 30~
98%, the mass concentration of the hydrochloric acid is 30%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710818270.7A CN107698433A (en) | 2017-09-12 | 2017-09-12 | The preparation method of phenylacetic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710818270.7A CN107698433A (en) | 2017-09-12 | 2017-09-12 | The preparation method of phenylacetic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107698433A true CN107698433A (en) | 2018-02-16 |
Family
ID=61172629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710818270.7A Pending CN107698433A (en) | 2017-09-12 | 2017-09-12 | The preparation method of phenylacetic acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107698433A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112574065A (en) * | 2020-12-30 | 2021-03-30 | 宁波职业技术学院 | Preparation method of (benzene-1, 3, 5-triacyl) acetonitrile |
| CN113801014A (en) * | 2021-07-30 | 2021-12-17 | 四川信乙化工有限公司 | Preparation process of phenylacetic acid |
| CN116332744A (en) * | 2023-03-24 | 2023-06-27 | 湖北旭捷新材料科技有限公司 | Preparation method of 5-oxo-caproic acid |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013098146A1 (en) * | 2011-12-29 | 2013-07-04 | Bayer Intellectual Property Gmbh | Fungicidal 3-[(1,3-thiazol-4-ylmethoxyimino)(phenyl)methyl]-2-substituted-1,2,4-oxadiazol-5(2h)-one derivatives |
| CN104402698A (en) * | 2014-10-29 | 2015-03-11 | 柳州丰康泰科技有限公司 | 2-(4-methylphenyl)propionic acid syntehsis method |
| CN105218401A (en) * | 2015-09-21 | 2016-01-06 | 河北诚信有限责任公司 | The method of continuous processing synthesis benzyl cyanide |
| CN106278861A (en) * | 2016-08-24 | 2017-01-04 | 河北诚信有限责任公司 | A kind of method preparing substituted phenylacetic acid |
| CN106278859A (en) * | 2016-08-24 | 2017-01-04 | 河北诚信有限责任公司 | A kind of production technology of high-quality phenylacetic acid |
| CN106366019A (en) * | 2016-08-31 | 2017-02-01 | 河北诚信有限责任公司 | Continuous cyaniding method in benzyl cyanide production |
| CN106431911A (en) * | 2016-09-28 | 2017-02-22 | 黄石市利福达医药化工有限公司 | Preparation and purification methods of 4-biphenylacetic acid |
| CN107001278A (en) * | 2014-10-08 | 2017-08-01 | Ucb生物制药私人有限公司 | Tetrahydro isoquinoline derivative |
-
2017
- 2017-09-12 CN CN201710818270.7A patent/CN107698433A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013098146A1 (en) * | 2011-12-29 | 2013-07-04 | Bayer Intellectual Property Gmbh | Fungicidal 3-[(1,3-thiazol-4-ylmethoxyimino)(phenyl)methyl]-2-substituted-1,2,4-oxadiazol-5(2h)-one derivatives |
| CN107001278A (en) * | 2014-10-08 | 2017-08-01 | Ucb生物制药私人有限公司 | Tetrahydro isoquinoline derivative |
| CN104402698A (en) * | 2014-10-29 | 2015-03-11 | 柳州丰康泰科技有限公司 | 2-(4-methylphenyl)propionic acid syntehsis method |
| CN105218401A (en) * | 2015-09-21 | 2016-01-06 | 河北诚信有限责任公司 | The method of continuous processing synthesis benzyl cyanide |
| CN106278861A (en) * | 2016-08-24 | 2017-01-04 | 河北诚信有限责任公司 | A kind of method preparing substituted phenylacetic acid |
| CN106278859A (en) * | 2016-08-24 | 2017-01-04 | 河北诚信有限责任公司 | A kind of production technology of high-quality phenylacetic acid |
| CN106366019A (en) * | 2016-08-31 | 2017-02-01 | 河北诚信有限责任公司 | Continuous cyaniding method in benzyl cyanide production |
| CN106431911A (en) * | 2016-09-28 | 2017-02-22 | 黄石市利福达医药化工有限公司 | Preparation and purification methods of 4-biphenylacetic acid |
Non-Patent Citations (2)
| Title |
|---|
| 刘树文主编: "《合成香料技术手册》", 31 July 2000, 中国轻工业出版社 * |
| 康文通等: "相转移催化合成苯乙腈的研究", 《河北工业科技》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112574065A (en) * | 2020-12-30 | 2021-03-30 | 宁波职业技术学院 | Preparation method of (benzene-1, 3, 5-triacyl) acetonitrile |
| CN113801014A (en) * | 2021-07-30 | 2021-12-17 | 四川信乙化工有限公司 | Preparation process of phenylacetic acid |
| CN116332744A (en) * | 2023-03-24 | 2023-06-27 | 湖北旭捷新材料科技有限公司 | Preparation method of 5-oxo-caproic acid |
| CN116332744B (en) * | 2023-03-24 | 2023-12-12 | 湖北旭捷新材料科技有限公司 | Preparation method of 5-oxo-caproic acid |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108997106A (en) | The preparation method of phenylacetic acid | |
| CN103333047B (en) | Preparation method of dichloropropanol | |
| CN107698433A (en) | The preparation method of phenylacetic acid | |
| CN104372017B (en) | A kind of method and application for improving genetic engineering bacterium isoprene and its derivative yield | |
| CN107473931A (en) | The production method of benzyl chloride | |
| CN107311868B (en) | Method for preparing p-tert-butyl methyl benzoate | |
| CN104263713A (en) | Tistrella mobilis, halohydrin dehalogenase, gene, vector, recombinant strain and application of halohydrin dehalogenase | |
| CN105037139A (en) | Preparation method for 2-phenylpropionic acid | |
| CN105316273B (en) | One plant without the L-Aspartic acid enzyme recombination bacillus coli and its construction method of malic acid by-product and application | |
| CN105837432A (en) | Novel preparation method of 3,5-dichlorobenzoyl chloride | |
| CN106380383B (en) | A kind of synthetic method of 2- hexenoic aldehyde | |
| CN104072357A (en) | Synthetic method for difluoroethanoic acid | |
| CN106518631A (en) | Preparing method for veratrole | |
| CN105779513A (en) | Method for producing succinic acid by recombinant escherichia coli through fermentation by using glycerol as carbon source | |
| CN107828752B (en) | Saccharopolyase, preparation method and application in production of alpha-arbutin | |
| CN110791467B (en) | Recombinant bacterium for producing acetylacetone and construction method and application thereof | |
| CN104311404A (en) | Method for producing cinnamyl aldehyde | |
| US10252985B2 (en) | Solvent-free green ammoximation process based on film distribution | |
| CN114702391A (en) | Method for preparing cyclopropylamine by performing Hofmann rearrangement by using hydrogen peroxide | |
| CN109206304B (en) | Preparation method of 2, 2-dimethoxypropane | |
| CN113651786A (en) | Method for synthesizing 6-hydroxy-2-ethyl-2H-pyrone- [3] by catalyzing alpha-furylpropanol oxidation and product | |
| CN108640822A (en) | The preparation method and 4- vinyl guaiacols of 4- vinyl guaiacols | |
| CN105646191B (en) | A kind of method for preparing fragrant dimethyl chloride | |
| CN106478390A (en) | A kind of method that pinacolone is prepared by chlorinated special pentane and formaldehyde condensation reaction | |
| CN104447329A (en) | Preparation method of 2-chloroacetoacetic acid ethyl ester |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20180216 |
|
| RJ01 | Rejection of invention patent application after publication |