CN109134389A - The purification process of 2,5- pyrazine dicarboxylic acids and obtained 2,5- pyrazine dicarboxylic acids - Google Patents
The purification process of 2,5- pyrazine dicarboxylic acids and obtained 2,5- pyrazine dicarboxylic acids Download PDFInfo
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- CN109134389A CN109134389A CN201811104411.XA CN201811104411A CN109134389A CN 109134389 A CN109134389 A CN 109134389A CN 201811104411 A CN201811104411 A CN 201811104411A CN 109134389 A CN109134389 A CN 109134389A
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- dicarboxylic acids
- mixed solution
- pyrazine dicarboxylic
- sediment
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
One kind 2, the purification process of 5- pyrazine dicarboxylic acids, include: weighing 2, 5- pyrazine dicarboxylic acids, it is placed in beaker, 2 are loaded with Ammonia addition, in the beaker of 5- pyrazine dicarboxylic acids, so that 2, 5- pyrazine dicarboxylic acids is completely dissolved, to obtain the first mixed solution, first mixed solution is separated by chromatographic column, to obtain the second mixed solution, third mixed solution is formed to the second mixed solution addition hydrochloric acid, and make its pH value 1, third mixed solution is stood, so that the sediment in third mixed solution starts to generate precipitating, third mixed solution is filtered, sediment is separated by third mixed solution, sediment is cleaned, to remove the hydrochloric acid remained on sediment and be cleaned using acetone to sediment, and the sediment after cleaning is dried, To obtain 2,5- pyrazine dicarboxylic acids after purification.A kind of 2,5- pyrazine dicarboxylic acids purified using purification process, the general formula with the structure as shown in formula (1):
Description
Technical field
The present invention is to be related to the purification process of one kind 2,5- pyrazine dicarboxylic acids, in particular to medicine intermediate or section
Learn the purification process of the reagent of class research.
Background technique
2,5- pyrazine dicarboxylic acids (PYRAZINE-2,5-DICARBOXYLIC ACID) be all used to as medicine intermediate or
It is the reagent for scientific research, impure more by 2, the 5- pyrazine dicarboxylic acids crude product bought on the market at present, product
It is in yellow or brown, and the granular size of crystal is uneven more.However, either synthetic drug or as scientific research
Reagent requires the good raw material or reagent of quality, and the purity of the accuracy or drug that can improve result of study is even
The pharmacological property of drug is only held, therefore, containing too polymictic defect pole for presently commercially available 2,5- pyrazine dicarboxylic acids need find
Suitable mode solves.
Summary of the invention
It is a primary object of the present invention to open one kind for commercially available 2,5- pyrazine dicarboxylic acids (PYRAZINE-2,5-
DICARBOXYLIC ACID) purification process, contained impurity is removed in 2,5- pyrazine dicarboxylic acids using chromatography, is improved
The problem of purity of 2,5- pyrazine dicarboxylic acids, solves in the prior art, and 2,5- pyrazine dicarboxylic acids contain impurity.
Another object of the present invention is to be purified for commercially available 2,5- pyrazine dicarboxylic acids, to control 2,5- pyrazine two
The crystalline size size of carboxylic acid, solves in the prior art, the crystal size partial size of 2,5- pyrazine dicarboxylic acids problem bigger than normal.
Another object of the present invention is by obtained 2, the 5- pyrazine dicarboxylic acids of purification process disclosed in this invention,
As the raw material sources of coating fluid, the advantage is that the light transmittance that can have height, thus can as large-scale window, and
Visible rays field artificial adjustment light transmittance can also obstruct 99% or more ultraviolet light, delay taking off for furniture or fiber product
The color time, and to the reflection characteristic near infrared ray field to indoor energy conservation 30% or more.
Another object of the present invention is to pass through obtained 2, the 5- pyrazine dicarboxylic acids of purification process disclosed in this invention,
Because it can stop the characteristics such as ultraviolet light, adjusting visible rays light transmittance, reflection infrared ray, it can be used for the day of the various vehicles
Window.Especially vehicle dormer window, to the light transmittance adjustable range of visible rays in 2-40%, to solar heat have it is effective stop it is special
Property, pleasant driving environment is built to interior driver.
According to above-mentioned purpose, the present invention discloses the purification process of one kind 2,5- pyrazine dicarboxylic acids, includes: weighing 1000g's
2,5- pyrazine dicarboxylic acids are placed in beaker, with ammonium hydroxide (NH4OH) burning for being loaded with 2,5- pyrazine dicarboxylic acids is added in solution
In cup, until 2,5- pyrazine dicarboxylic acids is dissolved completely in Ammonia, it is molten to obtain the first mixed solution, be mixed first
Liquid is separated by chromatographic column, to obtain the second mixed solution, add hydrochloric acid to the second mixed solution to form third mixing
Solution, hydrochloric acid addition is until the pH value of third mixed solution is 1, and is stirred simultaneously to third mixed solution, is mixed to third
Solution left standstill is closed, so that the sediment in third mixed solution starts to generate precipitating, be filtered to third mixed solution, will be sunk
Starch is separated by third mixed solution, is cleaned using the first clean solution to sediment, remains in precipitating to remove
Hydrochloric acid on object and sediment is cleaned using the second clean solution, and the sediment after cleaning is dried, with
The 2,5- pyrazine dicarboxylic acids purified.
According to the above, the present invention using chromatography by impurity by doing preliminary separation in 2,5- pyrazine dicarboxylic acids, then
Remaining impurity acid is washed away using hydrochloric acid and is removed, by the available purity of way of purification disclosed in this invention higher 2,5-
The purity and reliability of the drug of synthesis can be improved as medical intermediate, be used for as R&D institution for pyrazine dicarboxylic acids
The accuracy of experimental data can be improved in the reagent of research experiment, solves in the prior art, 2, the 5- pyrazine two containing impurity
Defect caused by carboxylic acid.
Detailed description of the invention
Fig. 1 is technology disclosed according to the present invention, indicates the step flow chart of 2,5- pyrazine dicarboxylic acids purification process.
Specific embodiment
In order to make the purpose of the present invention, technical characteristic and advantage, can more correlative technology field personnel understood, and be able to
Implement the present invention, cooperates appended schema herein, specifically illustrates technical characteristic and embodiment of the invention, and enumerate preferable reality
Apply example further explanation.It is not also needed with the schema hereinafter compareed to express signal related with feature of present invention
It is completely drawn according to practical situation.And the technology well-known to those skilled in the art involved in the explanation of this case embodiment
Content is also no longer stated.
The present invention proposes that the concept purified to 2,5- pyrazine dicarboxylic acids is primarily due to the 2,5- by obtaining on the market
Pyrazine dicarboxylic acids is crude product, has the general formula of the structure as shown in formula (1):
And the crystal particle diameter size of commercially available 2,5- pyrazine dicarboxylic acids is uneven, and 2, the crystal color of 5- pyrazine dicarboxylic acids is presented
Yellow or brown, with more impurity, if the purity of drug after composition is not yet as the raw material of synthetic drug
Height, reliability reduce, and also influence drug quality；If or the reagent then 2,5- pyrazine dicarboxylic acids as R&D institution's experiment
Impurity be easy influence experimental data accuracy.Therefore the present invention disclose a kind of utilization chromatography for 2,5- pyrazine dicarboxylic acids
In impurity by being removed in 2,5- pyrazine dicarboxylic acids, and again penetrate pickling mode, remove remaining impurity, and can control
The crystal particle diameter size for making 2,5- pyrazine dicarboxylic acids obtains 2, the 5- pyrazine dicarboxylic acids of purity is high, detailed purifying step whereby
It is rapid as described below.
Please refer to Fig. 1.According to Fig. 1 disclosed herein technology, indicate 2,5- pyrazine dicarboxylic acids purification process step
Rapid flow chart.Step 10: previously prepared concentration is the ammonium hydroxide (NH of 2N4OH) solution.In this step 10, by 3500ml's
Distilled water pours into the flask of 4L, then the ammonium hydroxide that 500ml concentration is 25% is poured into the flask for being loaded with distilled water, mixes
Uniformly, the ammonium hydroxide (NH that concentration is 2N is obtained4OH) solution, and the bottleneck of flask is sealed with plug, give subsequent step
It is spare.
Step 12: weighing commercially available 2,5- pyrazine dicarboxylic acids weight 1000g and be placed in a beaker.
Step 14: the ammonium hydroxide (NH that will previously prepare, concentration is 2N4OH) solution, which pours into, is loaded with 2,5- pyrazine two
In the beaker of carboxylic acid, until 2, the 5- pyrazine dicarboxylic acids in beaker is dissolved completely in Ammonia, and it is mixed to obtain first
Close solution.In this step, chemical equation is as described under formula (2):
Wherein, the left side of formula (2) be by commercially available 2,5- pyrazine dicarboxylic acids and Ammonia hybrid reaction so that
Carboxyl (the COO in carboxylic acid group (COOH) in 2,5- pyrazine dicarboxylic acids?) and ammonium ion (NH4 +) bond, and the hydrogen in carboxylic acid group
Ion (H+) with Ammonia in hydroxide ion (OH?) bond generation water (H2O).Therefore, in the first mixed solution
Main ingredient be formula (2) left side structure and water.
Then, step 16: the first mixed solution being chromatographed using chromatography to isolate in the first mixed solution
Impurity.In step 16, the first mixed solution is subjected to chromatography by chromatography tubing string, it is molten in the first mixing to isolate
Impurity in liquid, wherein the flow velocity of the mobile phase of chromatographic column is 10-20cc/min, and preferable flow velocity is 10cc/min.Specifically
For, when 2,5- pyrazine dicarboxylic acids is dissolved completely in Ammonia, the impurity that 2,5- pyrazine dicarboxylic acids are had also can
It is dissolved in Ammonia simultaneously, by chromatography, by impurity by being precipitated in the first mixed solution to obtain by separation
Second mixed solution, in an embodiment of the present invention, the stationary phase of chromatographic column used in chromatography is active carbon, mobile phase the
One mixed solution, i.e. 2,5- pyrazine dicarboxylic acids are dissolved completely in the mixed solution after Ammonia.
Then step 18: hydrochloric acid is added to the second mixed solution for having carried out chromatography and is stirred to form third mixing
Solution, it is 1 i.e. stopping addition that wherein hydrochloric acid, which is added to the pH-value (pH value) of third mixed solution,.In step 18, salt is added
The reaction equation such as formula (3) of acid to the second mixed solution for having been subjected to chromatography is described:
Wherein, during the left side of formula (3) is reacted with hydrochloric acid, solution can begin to change into milky, and hydrochloric acid (HCl) mentions
Hydrogen ion (the H of confession+) can be with the carboxyl (COO in the chemical formula of left side?) combine, and ammonium ion (NH4 +) can with the chlorine in hydrochloric acid from
Son (Cl?) combine, and be precipitated into chlorination ammonium salt (NH4Cl), so that foring 2,5- pyrazine dicarboxylic acids again in third mixed solution,
Chemical formula i.e. on the right side of formula (3):But 2,5- pyrazine dicarboxylic acids at this time has been
By product after purification.In addition, the concentration of added hydrochloric acid is 37% in this step.It therefore, can by above-mentioned reaction equation (3)
To learn, the purpose for adding hydrochloric acid is will further to carry out pickling in the second mixed solution for having carried out chromatography, will
Impurity is precipitated in the second mixed solution by having carried out chromatography, and (hydrochloric acid and has carried out in third mixed solution
The mixed solution of second mixed solution of chromatography) in, further to purify 2,5- pyrazine dicarboxylic acids, furthermore penetrate hydrochloric acid
The step of addition, can control the crystal particle diameter size of 2,5- pyrazine dicarboxylic acids.
Following step 20: third mixed solution is stood, and is sunk so that the sediment in third mixed solution starts to generate
It forms sediment, in this step 20, the time of standing is 10-16 hours, and preferable time of repose is 12 hours.
Step 22: third mixed solution being filtered, sediment is separated by third mixed solution.When third is mixed
Close and begin with crystal and generate precipitating by being precipitated in third mixed solution after solution left standstill, at this time in order to by sediment by the
It is separated in three mixed solutions, is reached using funnel especially Buchner funnel, sediment is filtered out and comes and is placed in
On Buchner funnel, filtrate (i.e. third mixed solution) can be contained in clean beaker.In this step, in order to ensure all
Sediment can be filtered out by third mixed solution Lai can be duplicate by filtered filtrate (third mixed solution)
It is filtered by funnel.
Step 24: sediment being cleaned using the first clean solution, to remove the hydrochloric acid remained on sediment.In
In this step, using the first clean solution such as distilled water, the especially distilled water of ice, temperature is -5 DEG C, for filtering out and holding
The sediment being placed on funnel is cleaned, and is filtered.The purpose of this step is, the hydrochloric acid that will remain on sediment
Removing is cleaned, and clean number does not limit.In an embodiment of the present invention, since 2,5- pyrazine dicarboxylic acids has centainly
Water solubility, step 24 be added ice distilled water be in order to preferably by Precipitation.
Then step 26: sediment is cleaned using the second clean solution, and the sediment after cleaning is done
It is dry, with 2, the 5- pyrazine dicarboxylic acids purified.Step 26 is the later progress of and then step 24, utilizes the second clean solution
Such as acetone, it is poured on the step of sediment being placed on funnel does further cleaning, and similarly filtered, cleaned
Number can be 2-6 times, but do not limit, at least 4 times in general practical operation, cleaning for the first time and clean for second,
And filtered, and third time and the 4th cleaning, it is drained after filtering, by the sediment after filtering and tentatively draining
2, the 5- pyrazine dicarboxylic acids that can be obtained after purification is dried, it is identical as formula (1) with general formula,
And after above-mentioned step 26 is using the second clean solution cleaning sediment, it can also include giving sediment
Stand, the upper end of funnel is covered in using filter paper, allow the acetone as the second clean solution to be volatilized and by sediment
It removes.
Finally, will it is dry after and purified 2,5- pyrazine dicarboxylic acids be directly placed into storage bottle and stored or used
Storage bottle is put into after Yan Portland grinding to be stored.
In addition, can be applied to for utilizing obtained 2, the 5- pyrazine dicarboxylic acids of purification process disclosed in this invention
Coating fluid, since the crystal color of purified 2,5- pyrazine dicarboxylic acids is blue, when as coating fluid, with height
Light transmittance.Therefore, 2, the 5- pyrazine dicarboxylic acids obtained using purification process disclosed in this invention can be made into large-scale window, excellent
Point is: 1, the curtain that can be replaced protection privacy, obstruct solar heat, so can also be used as building materials window.It can be in visible rays
Field artificial adjustment light transmittance can also obstruct 99% or more ultraviolet light, can delay the fading time of furniture or fiber product, and
And to the reflection characteristic near infrared ray field to indoor energy conservation 30% or more.2, the product is because of its blocking ultraviolet light, tune
The characteristics such as visible rays light transmittance, reflection infrared ray are saved, can be used for the skylight of the various vehicles.Especially vehicle dormer window, it is right
The light transmittance adjustable range of visible rays has effective barrier properties in 2-40%, to solar heat, to interior driver battalion
Make pleasant driving environment.
According to the above, the present invention using chromatography by impurity by doing preliminary separation in 2,5- pyrazine dicarboxylic acids, then
Remaining impurity acid is washed away using hydrochloric acid and is removed, by the available purity of way of purification disclosed in this invention higher 2,5-
The purity and reliability of the drug of synthesis can be improved as medical intermediate, be used for as R&D institution for pyrazine dicarboxylic acids
The accuracy of experimental data can be improved in the reagent of research experiment, solves in the prior art, 2, the 5- pyrazine two containing impurity
Defect caused by carboxylic acid.
The foregoing is merely the preferred embodiments of the invention, the interest field that is not intended to limit the invention；More than simultaneously
Description, the special personage of correlative technology field should can be illustrated and be implemented, thus other without departing from it is disclosed it
The lower equivalent change or modification completed of spirit, should be included in claim.
Claims (10)
1. one kind 2, the purification process of 5- pyrazine dicarboxylic acids, which is characterized in that the purification process packet of 2, the 5- pyrazine dicarboxylic acids
Include following steps:
(1) 2, the 5- pyrazine dicarboxylic acids for weighing 1000g, is placed in beaker；
(2) ammonium hydroxide (NH is used4OH) solution addition is loaded in the beaker of 2, the 5- pyrazine dicarboxylic acids, until described
2,5- pyrazine dicarboxylic acids are dissolved completely in the Ammonia, to obtain the first mixed solution；
(3) first mixed solution is separated by chromatographic column, to obtain the second mixed solution；
(4) hydrochloric acid is added to second mixed solution to form third mixed solution, the hydrochloric acid addition is until the third
The pH value of mixed solution is 1, and is stirred simultaneously to the third mixed solution；
(5) the third mixed solution is stood, so that the sediment in the third mixed solution starts to generate precipitating；
(6) the third mixed solution is filtered, the sediment is separated by the third mixed solution；
(7) sediment is cleaned using the first clean solution, to remove the salt remained on the sediment
Acid；And
(8) sediment is cleaned using the second clean solution, and the sediment after cleaning is dried, with
The 2,5- pyrazine dicarboxylic acids purified.
2. the purification process of 2,5- pyrazine dicarboxylic acids as described in claim 1, which is characterized in that the stationary phase of the chromatographic column
It can be active carbon.
3. the purification process of 2,5- pyrazine dicarboxylic acids as described in claim 1, which is characterized in that the mobile phase of the chromatographic column
It can be first mixed solution.
4. the purification process of 2,5- pyrazine dicarboxylic acids as claimed in claim 3, which is characterized in that the stream of the chromatographic column
The flow velocity of dynamic phase is 10-20cc/min.
5. the purification process of 2,5- pyrazine dicarboxylic acids as described in claim 1, which is characterized in that the third mixed solution
Time of repose is 10-15 hours.
6. the purification process of 2,5- pyrazine dicarboxylic acids as described in claim 1, which is characterized in that the first clean solution is
Distilled water.
7. the purification process of 2,5- pyrazine dicarboxylic acids as described in claim 1, which is characterized in that the second clean solution is
Acetone.
8. the purification process of 2,5- pyrazine dicarboxylic acids as described in claim 1, which is characterized in that cleaned using described second molten
It is 2-6 times that liquid, which carries out wash number to the sediment,.
9. the purification process of 2,5- pyrazine dicarboxylic acids as described in claim 1, which is characterized in that described in being utilized in step (7)
Second clean solution allows to further including the sediment after cleaning after the sediment and between step (8) and stood
The second clean solution evaporation and remove.
10. 2,5- pyrazine two prepared by a kind of purification process using 2,5- pyrazine dicarboxylic acids as claimed in claims 1-9
Carboxylic acid, the general formula with the structure as shown in formula (1):
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111689910A (en) * | 2020-06-19 | 2020-09-22 | 江苏铁锚玻璃股份有限公司 | Method for removing impurity iodine in pyrazine compound |
| CN114394943A (en) * | 2022-01-04 | 2022-04-26 | 江苏铁锚玻璃股份有限公司 | Method for purifying insoluble solid dicarboxylic acid |
| CN115403529A (en) * | 2022-09-26 | 2022-11-29 | 济南悟通生物科技有限公司 | Purification method of 2, 5-pyrazine dicarboxylic acid by-product |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4871736A (en) * | 1986-11-25 | 1989-10-03 | The Ohio State University | Stereoisomeric tricyclic bis(dioxopiperazines) and pharmaceutical compositions |
| JP2018090531A (en) * | 2016-12-02 | 2018-06-14 | 日立化成テクノサービス株式会社 | Method for producing heteroaromatic carboxylic acid |
-
2018
- 2018-09-21 CN CN201811104411.XA patent/CN109134389A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4871736A (en) * | 1986-11-25 | 1989-10-03 | The Ohio State University | Stereoisomeric tricyclic bis(dioxopiperazines) and pharmaceutical compositions |
| JP2018090531A (en) * | 2016-12-02 | 2018-06-14 | 日立化成テクノサービス株式会社 | Method for producing heteroaromatic carboxylic acid |
Non-Patent Citations (1)
| Title |
|---|
| W. J. SCHUT ET AL.: "INVESTIGATIONS ON PYRAZINE DERIVATIVES. VII On the conversion of pyrazine 2,5-dicarboxylic acid into some derivatives of 2-aminopyrazine 5-carboxylic acid", 《RECUEIL》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111689910A (en) * | 2020-06-19 | 2020-09-22 | 江苏铁锚玻璃股份有限公司 | Method for removing impurity iodine in pyrazine compound |
| CN111689910B (en) * | 2020-06-19 | 2022-03-08 | 江苏铁锚玻璃股份有限公司 | Method for removing impurity iodine in pyrazine compound |
| CN114394943A (en) * | 2022-01-04 | 2022-04-26 | 江苏铁锚玻璃股份有限公司 | Method for purifying insoluble solid dicarboxylic acid |
| CN115403529A (en) * | 2022-09-26 | 2022-11-29 | 济南悟通生物科技有限公司 | Purification method of 2, 5-pyrazine dicarboxylic acid by-product |
| CN115403529B (en) * | 2022-09-26 | 2023-06-13 | 济南悟通生物科技有限公司 | Purification method of 2, 5-pyrazine dicarboxylic acid byproduct |
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Application publication date: 20190104 |