CN108299217A - A kind of process and system producing D-phenylalanine - Google Patents
A kind of process and system producing D-phenylalanine Download PDFInfo
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- CN108299217A CN108299217A CN201710025823.3A CN201710025823A CN108299217A CN 108299217 A CN108299217 A CN 108299217A CN 201710025823 A CN201710025823 A CN 201710025823A CN 108299217 A CN108299217 A CN 108299217A
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- phenylalanine
- kettle
- condensing crystallizing
- reaction kettle
- tartaric acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/34—Preparation of optical isomers by separation of optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Abstract
The invention discloses a kind of techniques and system producing D phenylalanines, after the D phenylalanine D tartaric acid double salt of gained is dissolved in water, ammonium hydroxide is added and adjusts its pH to the isoelectric point of D phenylalanines, then it is added in the raw water room of electrodialysis plant, when conductivity is zero or so, the aqueous solution of D phenylalanines in raw water room is imported in the first condensing crystallizing kettle, concentrated crystallization, centrifuge and be dried to obtain D phenylalanines, the D tartrate ions of cathode enriched chamber import in the second condensing crystallizing kettle, concentrated crystallization, centrifugation obtains D tartaric acid, the D tartaric acid of gained, which is returned again into the second reaction kettle, to be reused.The present invention is improved prior art and system, and isolated D phenylalanines are carried out to gained double salt using electrodialysis plant, simple to operate, the time is saved, high income, up to 85 90%, and methanol and triethylamine need not be used, advantage of lower cost, also environmental protection.
Description
Technical field
The present invention relates to a kind of processes and system producing D-phenylalanine.
Background technology
D-phenylalanine is a kind of important chiral amino acid, in medicine, chemical field extensive use.Such as, D- phenylpropyl alcohols ammonia
Acid be anti-diabetic nateglinide how (nateglinide), antineoplastic skin (octreotide) difficult to understand bent, AIDS drugs
The raw material of indinavir (indinavir), it is also possible to make chiral reagent or chiral intermediate.In addition, D-phenylalanine also may be used
To be used directly as drug, such as compressive resistance agent, control diabetic agent, anti-inflammatory and analgesic agents are may be used as, can also be used as
Chiral reagent or chiral intermediate.
Preparation method about D-phenylalanine has many reports, it is industrial at present mainly use by L-phenylalanine not
Symmetrical conversion prepares D-phenylalanine, and process system includes the first reaction kettle being sequentially connected, the first centrifuge, the first conveying
Machine, the second reaction kettle, the second centrifuge, second conveyor, third reaction kettle, Suction filtration device and condensing crystallizing kettle, utilize its work
When process system is produced, first L-phenylalanine, catalyst salicylide and solvent acetic acid are added to the first reaction kettle, by institute
The reactant obtained is sent into the second reaction kettle, and D- tartaric acid, after reaction, concentrated Crystallization Separation are added into the second reaction kettle
It obtains DL-phenylalanine and is sent into the second reaction kettle, D- tartaric acid, after reaction, concentrated knot are added into the second reaction kettle
Brilliant isolated D-phenylalanine D- tartaric acid double salt；D-phenylalanine D- tartaric acid double salt is sent into third reaction kettle,
Triethylamine is added into third reaction kettle again and methanol is dissociated, after being stirred to react 1-2h, D- tartaric acid is given birth to triethylamine
At salt because being precipitated insoluble in methanol, after Suction filtration device is filtered to remove, the obtained filtrate condensing crystallizing in condensing crystallizing kettle
After obtain D- tartaric acid, the triethylamine used is needed in the technique, it is expensive, of high cost, in addition, also needing using a large amount of molten
Agent methanol, not environmentally.
Invention content
The present invention provides a kind of process system producing D-phenylalanine, is improved to prior art system, utilizes electricity
Electrodialysis apparatus carries out isolated D-phenylalanine to gained double salt, simple to operate, saves the time, high income, up to 85-
90%, and without using triethylamine and solvent methanol, advantage of lower cost, environmental protection.
To solve the above-mentioned problems, the technical solution adopted in the present invention is such, a kind of D-phenylalanine that produces
Process includes the following steps：
1）After aldehydes catalyst and acetic acid the first reaction kettle of addition are stirred evenly, L-phenylalanine is added, after reaction, warp
Condensing crystallizing centrifuges to obtain DL-phenylalanine；
2）By step 1）It obtains DL-phenylalanine and is sent into the second reaction kettle, propionic acid and D- tartaric acid is added, after reaction, warp
Condensing crystallizing centrifuges to obtain D-phenylalanine D- tartaric acid double salt；
3）By step 2）Obtained D-phenylalanine D- tartrates are sent into third reaction kettle, and after being dissolved in water, ammonium hydroxide is added
Its pH is adjusted to the isoelectric point of D-phenylalanine；
4）Solution in third reaction kettle is added in the raw water room of electrodialysis plant, under the action of electric field, in raw water room
D- tartrate ions are attracted to cathode enriched chamber by force, and ammonium ion is then attracted to anode enriched chamber, D- phenylpropyl alcohols by force
Propylhomoserin solution then stays in diluting compartment, and when conductivity is zero or so, the aqueous solution of D-phenylalanine in raw water room is imported the
It is concentrated in one condensing crystallizing kettle to crystallize, centrifuge and be dried to obtain D-phenylalanine, the D- tartrate ions of cathode enriched chamber
It imports concentrated crystallization, centrifugation in the second condensing crystallizing kettle and obtains D- tartaric acid, the D- tartaric acid of gained is returned again to second anti-
It answers in kettle and reuses.
Preferably, step 3）Middle D-phenylalanine is 40-50 DEG C in the condensing crystallizing temperature of the first condensing crystallizing kettle；D- wine
Stone acid is 40-50 DEG C in the condensing crystallizing temperature of the second condensing crystallizing kettle.
Step 2）In, the weight ratio 2-3 of amount of water and D-phenylalanine salt D- tartaric acid double salt：1.
When electrodialysis plant works, control electrodialysis plant voltage is 24-25V.
Producing the process system of D-phenylalanine the present invention also provides a kind of, including be sequentially connected the first reaction kettle,
One centrifuge, the first conveyer, the second reaction kettle, the second centrifuge, second conveyor and third reaction kettle, the third are anti-
Kettle is answered to be connected with the raw water room import of electrodialysis plant by feed pipe, the raw water room outlet of electrodialysis plant is discharged by raw water
Pipe is connected with the first condensing crystallizing kettle, and the first condensing crystallizing kettle is connected with third centrifuge and vacuum drier successively,
The outlet of electrodialysis plant anion enriched chamber is connected by concentrated water discharge nozzle with the second condensing crystallizing kettle, the described second concentration
Crystallization kettle is connected with the 4th centrifuge, and the 4th centrifuge is connected by the 4th conveyer with the second reaction kettle.
The applicable present invention of existing electrodialysis plant, it is preferable that the electrodialysis plant includes electrodialysis cell, institute
The electrodialysis cell stated passes through the first cation-exchange membrane of belt supporting frame, the first anion-exchange membrane, the second cation-exchange membrane,
Two anion-exchange membranes are separated into 5 reative cells, respectively are anode chamber, anion enriched chamber, raw water room, cation concentration
Room and cathode chamber are provided with positive electrode in the anode chamber, negative electrode are provided in cathode chamber.
For the pH in on-line determination third reaction kettle, pH detection meters are provided in the third reaction kettle.
Advantageous effect：The present invention is improved prior art system and method, using electrodialysis plant to gained D- benzene
Alanine D- tartaric acid double salt is detached, and double salt is sent into reaction kettle after centrifugation, and water then is added into third reaction kettle,
Electrodialysis plant is added after ammonium hydroxide adjusts its pH value to the isoelectric point of D-phenylalanine, then by the solution in third reaction kettle
In raw water room, under the action of electric field, the D- tartrate ions in raw water room are attracted to cathode enriched chamber by force, ammonium root from
Son is attracted to anode enriched chamber by force, and D-phenylalanine solution then stays in diluting compartment, is finally imported into condensing crystallizing kettle
In concentrated crystallization obtain D-phenylalanine, the process system is simple to operate, saves the time, high income, up to 85-90%,
And without using methanol and expensive triethylamine, advantage of lower cost, environmental protection.
Description of the drawings
Fig. 1 is schematic structural view of the invention.
Specific implementation mode
In order to deepen the understanding of the present invention, below in conjunction with embodiment and attached drawing, the invention will be further described, should
Embodiment is only used for explaining the present invention, is not intended to limit the scope of the present invention..
A kind of process producing D-phenylalanine of embodiment 1, includes the following steps：
1）Acetic acid 1300kg and salicylide 5kg is added into the first dried reaction kettle, after stirring evenly, then throws raw material L-
Phenylalanine 500kg is warming up to 70 DEG C, and insulated and stirred 1 hour, after reaction terminates, concentrated crystallization centrifugation obtains DL- benzene
Alanine 450kg；
2）The 450kgDL- phenylalanines of gained are added in the second reaction kettle, the propionic acid and 410kgD- wine of 1500kg are added
Stone acid is warming up to 65 DEG C, and insulated and stirred 4 hours, after reaction terminates, concentrated crystallization centrifugation obtains D-phenylalanine D- wine
Stone acid double salt 810kg.
3）The 810kgD- phenylalanine D- tartaric acid double salt of gained is added in third reaction kettle, adds 1620kg water-soluble
Xie Hou is added ammonium hydroxide and adjusts its pH to the isoelectric point of D-phenylalanine（5.5）；
4）D-phenylalanine D- tartaric acid complex salt solutions in third reaction kettle are sent in the raw water room of electrodialysis plant,
It is 24.5 volts to control electrodialysis plant current density voltage, under the action of electric field, the D- tartrate ion quilts in raw water room
It is attracted to cathode enriched chamber by force, ammonium ion is then attracted to anode enriched chamber 14 by force, and D-phenylalanine solution then stays in
In diluting compartment, when conductivity is zero or so, the aqueous solution of D-phenylalanine in raw water room is imported in the first condensing crystallizing kettle
It is concentrated（Thickening temperature is 45 DEG C）It crystallizes, centrifuge, being dried to obtain 370kgD- phenylalanines, the D- tartaric acid of cathode enriched chamber
Radical ion imports concentrated crystallization in the second condensing crystallizing kettle（Thickening temperature is 45 DEG C）, centrifugation obtain 350kgD- tartaric acid, institute
D- tartaric acid is returned again into the second reaction kettle and is reused.
Embodiment 2
The first reaction kettle 1, first centrifugation that is a kind of to produce the process system of D-phenylalanine referring to Fig. 1, including being sequentially connected
Machine 111, the first conveyer 112, the second reaction kettle 2, the second centrifuge 221, second conveyor 222 and third reaction kettle 3 are described
Third reaction kettle 3 be connected with 13 import of raw water room of electrodialysis plant by feed pipe, the raw water room 13 of electrodialysis plant goes out
Mouthful be connected with the first condensing crystallizing kettle 5 by raw water discharge nozzle, the first condensing crystallizing kettle 5 successively with third centrifuge
331 are connected with vacuum drier 332, and the outlet of electrodialysis plant anion enriched chamber 12 is concentrated by concentrated water discharge nozzle and second
Crystallization kettle 6 is connected, and the second condensing crystallizing kettle 6 is connected with the 4th centrifuge 441, and the 4th centrifuge 441 is defeated by the 4th
Machine 442 is sent to be connected with the second reaction kettle 2.
Wherein, the electrodialysis plant includes electrodialysis cell, the electrodialysis cell by belt supporting frame first sun from
Proton exchange 7, the first anion-exchange membrane 8, the second cation-exchange membrane 9, the second anion-exchange membrane 10 are separated into 5 reactions
Room respectively is anode chamber 11, anion enriched chamber 12, raw water room 13, cationic enriched chamber 14 and cathode chamber 15, described
It is provided with positive electrode 16 in anode chamber 11, negative electrode 17 is provided in cathode chamber 15.
For the pH in on-line determination third reaction kettle, pH detection meters are provided in the third reaction kettle.
The course of work：Acetic acid and salicylide are added into the first dried reaction kettle 1, after stirring evenly, then throws raw material
L-phenylalanine, after should terminating, condensing crystallizing liquid obtains DL-phenylalanine after the centrifugation of the first centrifuge 111；By gained
DL-phenylalanine is added through the first conveyer 112 in the second reaction kettle 2, adds propionic acid and D- tartaric acid, heats up, reaction knot
Shu Yihou, condensing crystallizing liquid obtain D-phenylalanine D- tartaric acid double salt through the centrifugation of the second centrifuge 221；By the D- benzene of gained
Alanine D- tartaric acid double salt is delivered to through second conveyor 222 in third reaction kettle 3, and after being dissolved in water, ammonium hydroxide tune is added
Its pH is saved to the isoelectric point of D-phenylalanine（5.5）；By the D-phenylalanine D- tartaric acid complex salt solutions in third reaction kettle 3
It is sent in the raw water room 13 of electrodialysis plant, under the action of electric field, the D- tartrate ions in raw water room 13 are by by force
It is attracted to cathode enriched chamber 12, ammonium ion is then attracted to anode enriched chamber 14 by force, and D-phenylalanine solution then stays in original
In hydroecium 13, when conductivity is zero or so, illustrate that D- tartrate ions and ammonium ion respectively shift to cathode enriched chamber
12 and anode enriched chamber 14, at this time will in raw water room the aqueous solution of D-phenylalanine import it is concentrated in the first condensing crystallizing kettle 5
Crystallization, for the condensing crystallizing liquid of gained after the separation of third centrifuge 331, vacuum dried machine 332 obtains D-phenylalanine；Cathode
The D- tartrate ions of enriched chamber import condensing crystallizing in the second condensing crystallizing kettle 6, the condensing crystallizing liquid of gained through third from
Scheming 441 is centrifugally separating to obtain D- tartaric acid, and gained D- tartaric acid by third conveyer 442 through being back in the second reaction kettle
Recycling.
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
With within principle, any modification, equivalent replacement, improvement and so on should all be included in the protection scope of the present invention god.
Claims (8)
1. a kind of process of D-phenylalanine, which is characterized in that include the following steps：
1）After aldehydes catalyst and acetic acid the first reaction kettle of addition are stirred evenly, L-phenylalanine is added, after reaction, warp
Condensing crystallizing centrifuges to obtain DL-phenylalanine；
2）By step 1）It obtains DL-phenylalanine and is sent into the second reaction kettle, propionic acid and D- tartaric acid is added, after reaction, warp
Condensing crystallizing centrifuges to obtain D-phenylalanine D- tartaric acid double salt；
3）By step 2）Obtained D-phenylalanine D- tartaric acid double salt is sent into third reaction kettle, and after being dissolved in water, ammonia is added
Water adjusts its pH to the isoelectric point of D-phenylalanine；
4）D-phenylalanine D- tartrate solutions in third reaction kettle are added in the raw water room of electrodialysis plant, in electricity
Under the action of, the D- tartrate ions in raw water room are attracted to cathode enriched chamber by force, and ammonium ion is then inhaled by force
Anode enriched chamber is led to, D-phenylalanine solution then stays in diluting compartment, when conductivity is zero or so, by D- benzene in raw water room
The aqueous solution of alanine imports in the first condensing crystallizing kettle, and concentrated crystallization centrifuges and be dried to obtain D-phenylalanine, and cathode is dense
The D- tartrate ions of contracting room import in the second condensing crystallizing kettle, and concentrated crystallization, centrifugation obtain D- tartaric acid, the D- of gained
Tartaric acid is returned again into the second reaction kettle and is reused.
2. the production technology of production D-phenylalanine according to claim 1, which is characterized in that step 3）Middle D- tartaric acid
It it is 40-50 DEG C in the condensing crystallizing temperature of the second condensing crystallizing kettle.
3. a kind of practical equipment producing D-phenylalanine according to claim 1, which is characterized in that step 3）In
D-phenylalanine is 40-50 DEG C in the condensing crystallizing temperature of the first condensing crystallizing kettle.
4. the production technology of production D-phenylalanine according to claim 1, which is characterized in that step 2）In, amount of water
With the weight ratio 2-3 of D-phenylalanine salt D- tartaric acid double salt：1.
5. the production technology of production D-phenylalanine according to claim 1, which is characterized in that electrodialysis plant works
When, control electrodialysis plant voltage is 24-25V.
6. a kind of process system producing D-phenylalanine, which is characterized in that including be sequentially connected the first reaction kettle, first from
Scheming, the first conveyer, the second reaction kettle, the second centrifuge, second conveyor and third reaction kettle, the third reaction kettle
Be connected with the raw water room import of electrodialysis plant by feed pipe, the outlet of the raw water room of electrodialysis plant by raw water discharge nozzle with
First condensing crystallizing kettle is connected, and the first condensing crystallizing kettle is connected with third centrifuge and vacuum drier successively, electric osmose
The outlet of analysis apparatus anion enriched chamber is connected by concentrated water discharge nozzle with the second condensing crystallizing kettle, second condensing crystallizing
Kettle is connected with the 4th centrifuge, and the 4th centrifuge is connected by the 4th conveyer with the second reaction kettle.
7. a kind of process system producing D-phenylalanine according to claim 6, which is characterized in that the electrodialysis
Device includes electrodialysis cell, the electrodialysis cell by the first cation-exchange membrane of belt supporting frame, the first anion-exchange membrane,
Second cation-exchange membrane, the second anion-exchange membrane are separated into 5 reative cells, respectively are anode chamber, anion concentration
Room, raw water room, cationic enriched chamber and cathode chamber are provided with positive electrode in the anode chamber, negative electricity are provided in cathode chamber
Pole.
8. a kind of process system producing D-phenylalanine according to claim 6, which is characterized in that the third is anti-
It answers and is provided with pH detection meters in kettle.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201710025823.3A CN108299217A (en) | 2017-01-13 | 2017-01-13 | A kind of process and system producing D-phenylalanine |
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| CN201710025823.3A CN108299217A (en) | 2017-01-13 | 2017-01-13 | A kind of process and system producing D-phenylalanine |
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| CN201710025823.3A Pending CN108299217A (en) | 2017-01-13 | 2017-01-13 | A kind of process and system producing D-phenylalanine |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110467539A (en) * | 2019-08-30 | 2019-11-19 | 浙江普洛家园药业有限公司 | The method for splitting of one kind 2,6- dimethyltyrosine ester and its application |
| CN115253364A (en) * | 2022-08-10 | 2022-11-01 | 安徽海蓝生物科技有限公司 | Centrifugation process and centrifugation equipment for tartaric acid solution |
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| EP0937705A2 (en) * | 1998-02-20 | 1999-08-25 | Yamakawa Chemical Industry Co., Ltd. | Process for preparing D-alloisoleucine and intermediates for preparation |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115253364B (en) * | 2022-08-10 | 2023-10-31 | 安徽海蓝生物科技有限公司 | Centrifugal process and centrifugal equipment for tartaric acid solution |
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