CN115093331A - Extraction process of benzylamine in high boiling point organic matter discharged from phenylglycine production - Google Patents
Extraction process of benzylamine in high boiling point organic matter discharged from phenylglycine production Download PDFInfo
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- CN115093331A CN115093331A CN202210846897.4A CN202210846897A CN115093331A CN 115093331 A CN115093331 A CN 115093331A CN 202210846897 A CN202210846897 A CN 202210846897A CN 115093331 A CN115093331 A CN 115093331A
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- benzylamine
- point organic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
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- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a process for extracting benzylamine from high-boiling-point organic matters discharged in phenylglycine production. The phenylglycine production process produces high boiling point organics which are typically disposed of as solid waste. The invention comprises the following steps: (1) adding solid sodium hydroxide into the high boiling point organic matter, adjusting the pH value to be more than 14, and changing the benzylamine from a sulfate state to a free benzylamine; (2) vacuum distilling, collecting 85-95 deg.C fraction with benzylamine as main ingredient under-0.09 MPa vacuum degree. The invention realizes an innovative method for obtaining benzylamine, which extracts benzylamine with economic value from high boiling point organic matters generated in the phenylglycine production process and sells the benzylamine as a byproduct; the economic value is maximized, and the discharge amount of solid wastes is reduced.
Description
Technical Field
The invention belongs to the field of wastewater treatment in a production process of a medical intermediate phenylglycine, and particularly relates to a process for extracting benzylamine from high-boiling-point organic matters discharged in the production of phenylglycine.
Background
The production process of phenylglycine comprises the working sections of synthesis, resolution, hydrolysis and the like; wherein the resolution process requires high temperature racemization (104-; in the racemization process, phenylglycine can generate decarboxylation reaction to generate a byproduct benzylamine; along with the increase of the number of times of mechanically applying the split mother liquor, the concentration of benzylamine is higher and higher, and can even reach 48% at the highest; after the split mother liquor can not be used mechanically, starting batch transfer; the byproduct benzylamine enters MVR along with the wastewater for concentration, and the byproduct ammonium sulfate is generated; when the wastewater is concentrated to a certain degree, organic matters such as benzylamine with high boiling point and the like can be discharged periodically; this high boiling point organic material is typically disposed of as solid waste.
Because benzylamine is used as an intermediate of dyes, medicines and polymers, the benzylamine can also be used for preparing the mafenide. If the byproduct benzylamine can be extracted and sold as qualified commodity, certain economic value can be generated. In order to achieve the purposes, an extraction process of benzylamine in high-boiling-point organic matters is developed, waste can be utilized, and the value is maximized.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides the process for extracting benzylamine from high-boiling-point organic matters discharged in phenylglycine production, which realizes the maximization of economic value and reduces the discharge amount of solid wastes.
Therefore, the invention adopts the following technical scheme: the extraction process of benzylamine from high boiling point organic matter exhausted from phenylglycine production is characterized by comprising the following steps: (1) adding solid sodium hydroxide into the high boiling point organic matter, adjusting the pH to be more than 14, and changing the benzylamine from a sulfate state to a free benzylamine; (2) vacuum distilling, and collecting 85-95 deg.C fraction with benzylamine as main ingredient under-0.09 MPa.
Preferably, the mass ratio of the high-boiling-point organic matter to the solid sodium hydroxide is 7-8: 1.
Preferably, the reduced pressure distillation is divided into two steps, wherein in the first step, the reaction kettle is used for carrying out crude distillation under the vacuum degree of-0.09 MPa, and all fractions below 100 ℃ are collected; the second step is to carry out rectification by a rectifying tower under the vacuum degree of-0.09 MPa, and respectively collect fractions with the temperature below 60 ℃ and the temperature between 85 ℃ and 95 ℃; wherein the high-boiling fraction at 85-95 deg.C is benzylamine.
Preferably, the residual liquid after the crude distillation and the rectification is barreled while hot and is treated as solid waste, and the fraction below 60 ℃ during the rectification is directly subjected to biochemical treatment.
The invention realizes an innovative method for obtaining benzylamine, which extracts benzylamine with economic value from high boiling point organic matters generated in the phenylglycine production process and sells the benzylamine as a byproduct; the economic value is maximized, and the discharge amount of solid wastes is reduced.
Detailed Description
The present invention is described in further detail below.
In the production process of phenylglycine, when the phenylglycine is racemized at high temperature, a decarboxylation side reaction can occur to produce benzylamine, and the reaction equation is as follows:
due to the process conditions, racemization inevitably requires the use of higher temperatures, so that decarboxylation side reactions occur, and the consumption of phenylglycine thus produced reaches 150-160kg/t, which is surprising.
Through detection, after the waste water produced in the phenylglycine production is concentrated by MVR to obtain a byproduct ammonium sulfate, the concentration of benzylamine in the generated high-boiling-point organic matter (by an external standard method) is up to 45-50%. And the yield of the high-boiling-point organic matters reaches 2t/d, and the high-boiling-point organic matters are treated as solid wastes at present.
For this purpose, the invention adopts the following specific embodiments to treat the high boiling point organic matter:
example 1: 800 g of high boiling point organic matter (45% of benzylamine) is taken, 100 g of caustic soda flakes is added and stirred until dissolution. The distillation was carried out under reduced pressure, and the whole fraction at 100 ℃ or lower was collected under a vacuum of-0.09 MPa to obtain 320g of a light brown liquid. Through HPLC analysis, the content of benzylamine by an area normalization method is 97.12 percent, and the content of benzylamine by an external standard method is 53.8 percent; the water content was 45.5% by Karl Fischer method.
Carrying out reduced pressure distillation on 320g of collected light brown liquid by using a rectification column under the vacuum degree of-0.09 MPa, collecting fractions below 60 ℃ to obtain 125 g of colorless liquid, and detecting by an HPLC (high performance liquid chromatography) external standard method to ensure that the content of benzylamine is 0.4%; collecting 85-95 deg.C fraction to obtain 170 g light amber liquid, and detecting by HPLC external standard method to obtain benzylamine content of 99.11%. And (3) putting the residual liquid after crude distillation and rectification into a barrel while the residual liquid is hot, and performing biochemical treatment on the residual liquid as solid waste, wherein the fraction below 60 ℃ is subjected to rectification directly.
Example 2: 800 g of high boiling point organic matter (benzylamine content 45%) is taken, 100 g of caustic soda flakes is added and stirred until dissolution. Carrying out reduced pressure distillation, collecting fractions below 60 ℃ under the vacuum degree of-0.09 MPa to obtain 130 g of colorless liquid, and detecting by an HPLC (high performance liquid chromatography) external standard method to obtain 1.4% of benzylamine; and collecting the fraction between 85 and 95 ℃ to obtain 163 grams of light amber liquid, wherein the content of benzylamine by the normalization method is 98.99 percent through HPLC detection.
Comparative example 1: 800 g of high boiling point organic matter (benzylamine content 45%) is taken, 100 g of caustic soda flakes is added and stirred until dissolution. Carrying out reduced pressure distillation, collecting fractions below 80 ℃ under the vacuum degree of-0.06 MPa to obtain 100 g of colorless liquid, and detecting by an HPLC (high performance liquid chromatography) external standard method to obtain 22.4% of benzylamine; fractions between 60 and 110 ℃ are collected to obtain 200 g of light amber liquid, and the benzylamine content is 78.06 percent by HPLC external standard detection.
It can be seen from the above examples that the technical scheme of example 1 is adopted to achieve the highest yield of benzylamine, and the technical scheme of the invention can realize the extraction of benzylamine from high-boiling-point organic substances, and the benzylamine can be sold as a byproduct; the economic value is maximized, and the discharge amount of solid wastes is reduced.
The foregoing shows and describes the general principles and broad features of the present invention and advantages thereof. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed.
Claims (4)
1. The extraction process of benzylamine from high boiling point organic matter exhausted from phenylglycine production is characterized by comprising the following steps: (1) adding solid sodium hydroxide into the high boiling point organic matter, adjusting the pH to be more than 14, and changing the benzylamine from a sulfate state to a free benzylamine; (2) vacuum distilling, and collecting 85-95 deg.C fraction with benzylamine as main ingredient under-0.09 MPa.
2. The benzylamine extraction process of claim 1, wherein the mass ratio of the high-boiling-point organic matter to the solid sodium hydroxide is 7-8: 1.
3. The benzylamine extraction process according to claim 1 or 2, wherein the vacuum distillation is performed in two steps, and in the first step, a reaction kettle is used for performing crude distillation under a vacuum degree of-0.09 MPa, and all fractions at a temperature of 100 ℃ or lower are collected; the second step is to carry out rectification by a rectifying tower under the vacuum degree of-0.09 MPa, and respectively collect fractions with the temperature below 60 ℃ and the temperature between 85 ℃ and 95 ℃; wherein the high-boiling fraction at 85-95 deg.C is benzylamine.
4. A process for extracting benzylamine according to claim 3, wherein the residue after the crude distillation and rectification is barrelled while hot and used as solid waste, and the fraction below 60 ℃ during rectification is subjected to biochemical treatment directly.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210846897.4A CN115093331A (en) | 2022-07-19 | 2022-07-19 | Extraction process of benzylamine in high boiling point organic matter discharged from phenylglycine production |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210846897.4A CN115093331A (en) | 2022-07-19 | 2022-07-19 | Extraction process of benzylamine in high boiling point organic matter discharged from phenylglycine production |
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| CN115093331A true CN115093331A (en) | 2022-09-23 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1008594A (en) * | 1963-07-03 | 1965-10-27 | Nat Res Dev | Process for the production of amines |
| CN1552694A (en) * | 2003-05-30 | 2004-12-08 | 上海实业化工有限公司 | Preparation of D-(-)-1-benzene amino acetic acid |
| CN114516811A (en) * | 2022-03-07 | 2022-05-20 | 浙江云涛生物技术股份有限公司 | Method for racemization reaction of phenylglycine in alkaline environment |
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2022
- 2022-07-19 CN CN202210846897.4A patent/CN115093331A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1008594A (en) * | 1963-07-03 | 1965-10-27 | Nat Res Dev | Process for the production of amines |
| CN1552694A (en) * | 2003-05-30 | 2004-12-08 | 上海实业化工有限公司 | Preparation of D-(-)-1-benzene amino acetic acid |
| CN114516811A (en) * | 2022-03-07 | 2022-05-20 | 浙江云涛生物技术股份有限公司 | Method for racemization reaction of phenylglycine in alkaline environment |
Non-Patent Citations (3)
| Title |
|---|
| KIMIAKI ISOBE ET AL.: ""Photodecarboxylation of Arylacetic Acids"", 《CHEM. PHARM.BULL.》, vol. 40, no. 8, pages 2188 - 2190 * |
| SHAH NAWAZ KHAN ET AL.: ""A General Method for Photocatalytic Decarboxylative Hydroxylation of Carboxylic Acids"", 《J. ORG. CHEM.》, vol. 85, pages 5019 - 5026 * |
| 李佳霖 等: ""氨基酸脱羧反应研究进展"", 《精细化工》, vol. 36, no. 8, pages 1501 - 1506 * |
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