CN108997211A - A kind of method of solvent crystallisation by cooling separation 4- cyanopyridine - Google Patents
A kind of method of solvent crystallisation by cooling separation 4- cyanopyridine Download PDFInfo
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- CN108997211A CN108997211A CN201810673365.9A CN201810673365A CN108997211A CN 108997211 A CN108997211 A CN 108997211A CN 201810673365 A CN201810673365 A CN 201810673365A CN 108997211 A CN108997211 A CN 108997211A
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- Prior art keywords
- cyanopyridine
- cooling separation
- solvent
- crystallisation
- decolorization
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- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 238000002425 crystallisation Methods 0.000 title claims abstract description 39
- 238000001816 cooling Methods 0.000 title claims abstract description 26
- 239000002904 solvent Substances 0.000 title claims abstract description 26
- 238000000926 separation method Methods 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000002994 raw material Substances 0.000 claims abstract description 11
- 238000004042 decolorization Methods 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 10
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000001035 drying Methods 0.000 claims abstract description 3
- 239000012452 mother liquor Substances 0.000 claims abstract description 3
- 239000002002 slurry Substances 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims description 18
- 230000008025 crystallization Effects 0.000 abstract description 18
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 238000011084 recovery Methods 0.000 abstract description 2
- 239000002699 waste material Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 19
- 239000013078 crystal Substances 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 12
- 239000000203 mixture Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- -1 alkyl pyridine Chemical compound 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 235000005152 nicotinamide Nutrition 0.000 description 2
- 239000011570 nicotinamide Substances 0.000 description 2
- 229960003966 nicotinamide Drugs 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- PDNNQADNLPRFPG-UHFFFAOYSA-N N.[O] Chemical compound N.[O] PDNNQADNLPRFPG-UHFFFAOYSA-N 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229940072185 drug for treatment of tuberculosis Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 235000020939 nutritional additive Nutrition 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention discloses a kind of methods of solvent crystallisation by cooling separation 4- cyanopyridine, include the following steps: that the mixing cyanopyridine raw material containing nicotinonitrile and 4- cyanopyridine is carried out decolorization by (1) at high temperature；(2) the mixing cyanopyridine raw material after decolorization is dissolved in advantage solvent methanol in a crystallizer, is configured to supersaturated solution；(3) be cooled to final temperature to supersaturated solution with certain cooling rate is precipitated 4- cyanopyridine, 4- cyanopyridine enters filter with mixing cyanopyridine mother liquor crystallizer is discharged in a form of slurry, the two is separated in the filter, then obtains high-purity 4- cyanopyridine product after drying.The present invention only needs One-step crystallization after raw material decolorization since crystallisation by cooling separation has the advantage of low energy consumption, low cost, and product purity is up to 99.2% ~ 99.7%.Production cost of the invention is low, good in economic efficiency, while also solving the problem of waste recovery utilizes.
Description
Technical field
The present invention relates to a kind of methods of solvent crystallisation by cooling separation 4- cyanopyridine.
Background technique
Cyanopyridine be widely used in pesticide and pesticide intermediate, medical product and medicine intermediate, feed and its raw material,
The production fields such as fragrance.Cyanopyridine mixture is mainly derived from the ammoxidation synthesis of alkyl pyridine, there are two types of which contains
Isomer: nicotinonitrile and 4- cyanopyridine.Wherein, the important use of nicotinonitrile be hydrolyzed obtained niacin or
Niacinamide also can be used as intermediate for synthesizing derivative products nicotinate chromium as feed addictive and nutritional additive.4- cyano
Pyridine is mainly used for synthesizing anti-tuberculosis drugs rimifon as important medicine, dyestuff intermediate.In order to obtain required height
Purity intermediates raw material, it is necessary to carry out separation and purification.
The method that industrial separation mostly uses rectification under vacuum at present is divided from nicotinonitrile and 4- cyanopyridine mixed system
4- cyanopyridine is separated out to increase economic efficiency.Since there are a small amount of picolines in ammonia oxygen in 3/4- cyanopyridine mixture
Change the by-product-anti-maleic nitrile (2-Butenedinitritle(Trans-) generated in reaction process), its presence will be tight
The separation of cyanopyridine mixture system is interfered again.Anti-maleic nitrile holds very much in cyanopyridine mixture system rectifying separation process
Polymerization reaction easily occurs, generated polymer not only influences the variation of material component in rectifying column, and polymerization generated
Object easily blocks rectifier unit equipment and influences its normal operation, causes the inferior separating effect of 4- cyanopyridine in industrial production strong
People's will, and it is high to operate operating cost.Consider that manufacturing enterprise is usually by the 3/4- cyano pyrrole of the cyanopyridine containing 4- based on economic cost
Pyridine homologous mixture works as offal treatment, or directly as chemical spent material burning disposal, leads to cyanopyridine homologous mixture
Recovery utilization rate it is low, cause greatly waste and environmental pollution.
Summary of the invention
The purpose of the present invention is overcome the deficiencies of the prior art and provide a kind of solvent crystallisation by cooling separation 4- cyanopyridine
Method.This method has the advantages that high efficiency, high-purity, low cost, low energy consumption.
The present invention utilizes solvent crystallisation by cooling partition method, dissolves in a solvent according to cyanopyridine admixture of isomeric compound
The difference of degree carries out separation 4- cyanopyridine.
Technical scheme is as follows:
A kind of method of solvent crystallisation by cooling separation 4- cyanopyridine, it is characterised in that include the following steps:
(1) the mixing cyanopyridine raw material containing nicotinonitrile and 4- cyanopyridine is subjected to decolorization at high temperature；
(2) the mixing cyanopyridine raw material after decolorization is dissolved in advantage solvent (methanol) in a crystallizer, is configured to satiate
And solution；Advantage solvent methanol selected by the present invention is from methanol, ethyl alcohol, n-butanol, normal propyl alcohol, isobutanol, acetone, acetic acid
It is screened in this 8 kinds of ethyl ester and carbon tetrachloride.Screening be at identical temperature nicotinonitrile and 4- cyanopyridine in the solvent
In the biggish solvent of dissolubility difference.
(3) be cooled to final temperature to supersaturated solution with certain cooling rate is precipitated 4- cyanopyridine, 4-
Cyanopyridine enters filter with mixing cyanopyridine mother liquor crystallizer is discharged in a form of slurry, and the two obtains in the filter
Separation, then high-purity 4- cyanopyridine product is obtained after drying.
In the method for above-mentioned solvent crystallisation by cooling separation 4- cyanopyridine, the temperature of step (1) described decoloration is 80
DEG C, and with stirring in decolorization.
In the method for above-mentioned solvent crystallisation by cooling separation 4- cyanopyridine, the operating temperature range of the crystallizer is
50 ~ 5 DEG C, operating pressure is normal pressure.
In the method for above-mentioned solvent crystallisation by cooling separation 4- cyanopyridine, the operation temperature of the filter is 0 ~ 5
DEG C, operating pressure is normal pressure.
In the method for above-mentioned solvent crystallisation by cooling separation 4- cyanopyridine, step (3) cooling rate is 0.05 ~
0.3℃/min。
In the method for above-mentioned solvent crystallisation by cooling separation 4- cyanopyridine, the crystallizer has agitating device.
Compared with prior art, the invention has the following beneficial effects: the present invention using one-step method solvent crystallisation by cooling point
From 4- cyanopyridine.Since crystallisation by cooling separation has the advantage of low energy consumption, low cost, and a step is only needed after raw material decolorization
Crystallization, product purity is up to 99.2% ~ 99.7%.Method production cost of the invention is low, good in economic efficiency, while also solving useless
The problem of material recycles.
The present invention will be further described below by way of examples, but is not limited only to the present embodiment.
Specific embodiment
Embodiment 1:
Mixing cyanopyridine raw material containing nicotinonitrile and 4- cyanopyridine is decolourized in decoloration device at 80 DEG C,
The filtrate after filtration treatment is added in methanol again, prepare the solution that degree of supersaturation is 0.05 at 45 DEG C and continues to stir, is stirred
Rate is 150 rpm, and crystallization temperature is down to 5 DEG C from 50 DEG C, and rate of temperature fall is 0.05 DEG C/min, the crystal that final filter is precipitated
For 99.4% high-purity 4- cyanopyridine product.
Embodiment 2:
According to condition described in embodiment 1 and step, prepares solution degree of supersaturation at 45 DEG C and be changed to 0.1, stirring rate 150
Rpm, crystallization temperature are down to 5 DEG C from 50 DEG C, and rate of temperature fall is 0.05 DEG C/min, and the crystal that final filter is precipitated is 99.5% high
Purity 4- cyanopyridine product.
Embodiment 3:
According to condition described in embodiment 1 and step, prepares solution degree of supersaturation at 45 DEG C and be changed to 0.2, stirring rate 150
Rpm, crystallization temperature are down to 5 DEG C from 50 DEG C, and rate of temperature fall is 0.05 DEG C/min, and the crystal that final filter is precipitated is 99.4% high
Purity 4- cyanopyridine product.
Embodiment 4:
According to condition described in embodiment 1 and step, prepares solution degree of supersaturation at 45 DEG C and be changed to 0.3, stirring rate 150
Rpm, crystallization temperature are down to 5 DEG C from 50 DEG C, and rate of temperature fall is 0.05 DEG C/min, and the crystal that final filter is precipitated is 99.4% high
Purity 4- cyanopyridine product.
Embodiment 5:
According to condition described in embodiment 1 and step, preparing solution degree of supersaturation at 45 DEG C is 0.05, stirring rate 150
Rpm, crystallization temperature are down to 5 DEG C from 50 DEG C, and rate of temperature fall is changed to 0.1 DEG C/min, and the crystal that final filter is precipitated is 99.6% high
Purity 4- cyanopyridine product.
Embodiment 6:
According to condition described in embodiment 5 and step, prepares solution degree of supersaturation at 45 DEG C and be changed to 0.1, stirring rate 150
Rpm, crystallization temperature are down to 5 DEG C from 50 DEG C, and rate of temperature fall is 0.1 DEG C/min, and the crystal that final filter is precipitated is 99.7% high
Purity 4- cyanopyridine product.
Embodiment 7:
According to condition described in embodiment 6 and step, prepares solution degree of supersaturation at 45 DEG C and be changed to 0.2, stirring rate 150
Rpm, crystallization temperature are down to 5 DEG C from 50 DEG C, and rate of temperature fall is 0.1 DEG C/min, and the crystal that final filter is precipitated is 99.4% high-purity
Spend 4- cyanopyridine product.
Embodiment 8:
According to condition described in embodiment 7 and step, prepares solution degree of supersaturation at 45 DEG C and be changed to 0.3, stirring rate 150
Rpm, crystallization temperature are down to 5 DEG C from 50 DEG C, and rate of temperature fall is 0.1 DEG C/min, and the crystal that final filter is precipitated is 99.5% high
Purity 4- cyanopyridine product.
Embodiment 9:
According to condition described in embodiment 1 and step, preparing solution degree of supersaturation at 45 DEG C is 0.05, stirring rate 150
Rpm, crystallization temperature are down to 5 DEG C from 50 DEG C, and rate of temperature fall is changed to 0.2 DEG C/min, and the crystal that final filter is precipitated is 99.6% high
Purity 4- cyanopyridine product.
Embodiment 10:
According to condition described in embodiment 9 and step, prepares solution degree of supersaturation at 45 DEG C and be changed to 0.1, stirring rate 150
Rpm, crystallization temperature are down to 5 DEG C from 50 DEG C, and rate of temperature fall is 0.2 DEG C/min, and the crystal that final filter is precipitated is 99.2% high-purity
Spend 4- cyanopyridine product.
Embodiment 11:
According to condition described in embodiment 10 and step, prepares solution degree of supersaturation at 45 DEG C and be changed to 0.2, stirring rate 150
Rpm, crystallization temperature are down to 5 DEG C from 50 DEG C, and rate of temperature fall is 0.2 DEG C/min, and the crystal that final filter is precipitated is 99.3% high
Purity 4- cyanopyridine product.
Embodiment 12:
According to condition described in embodiment 11 and step, prepares solution degree of supersaturation at 45 DEG C and be changed to 0.3, stirring rate 150
Rpm, crystallization temperature are down to 5 DEG C from 50 DEG C, and rate of temperature fall is 0.2 DEG C/min, and the crystal that final filter is precipitated is 99.4% high
Purity 4- cyanopyridine product.
Embodiment 13:
According to condition described in embodiment 1 and step, preparing solution degree of supersaturation at 45 DEG C is 0.05, stirring rate 150
Rpm, crystallization temperature are down to 5 DEG C from 50 DEG C, and rate of temperature fall is changed to 0.3 DEG C/min, and the crystal that final filter is precipitated is 99.2% high
Purity 4- cyanopyridine product.
Embodiment 14:
According to condition described in embodiment 13 and step, prepares solution degree of supersaturation at 45 DEG C and be changed to 0.1, stirring rate 150
Rpm, crystallization temperature are down to 5 DEG C from 50 DEG C, and rate of temperature fall is 0.3 DEG C/min, and the crystal that final filter is precipitated is 99.6% high
Purity 4- cyanopyridine product.
Embodiment 15:
According to condition described in embodiment 13 and step, prepares solution degree of supersaturation at 45 DEG C and be changed to 0.2, stirring rate 150
Rpm, crystallization temperature are down to 5 DEG C from 50 DEG C, and rate of temperature fall is 0.3 DEG C/min, and the crystal that final filter is precipitated is 99.3% high
Purity 4- cyanopyridine product.
Embodiment 16:
According to condition described in embodiment 13 and step, prepares solution degree of supersaturation at 45 DEG C and be changed to 0.3, stirring rate 150
Rpm, crystallization temperature are down to 5 DEG C from 50 DEG C, and rate of temperature fall is 0.3 DEG C/min, and the crystal that final filter is precipitated is 99.5% high-purity
Spend 4- cyanopyridine product.
Claims (6)
1. a kind of method of solvent crystallisation by cooling separation 4- cyanopyridine, it is characterised in that include the following steps:
(1) the mixing cyanopyridine raw material containing nicotinonitrile and 4- cyanopyridine is subjected to decolorization at high temperature；
(2) the mixing cyanopyridine raw material after decolorization is dissolved in advantage solvent methanol in a crystallizer, is configured to supersaturation
Solution；
(3) be cooled to final temperature to supersaturated solution with certain cooling rate is precipitated 4- cyanopyridine, 4- cyano
Pyridine enters filter with mixing cyanopyridine mother liquor crystallizer is discharged in a form of slurry, and the two is divided in the filter
From, then high-purity 4- cyanopyridine product is obtained after drying.
2. the method for solvent crystallisation by cooling separation 4- cyanopyridine as described in claim 1, which is characterized in that step (1) institute
The temperature for stating decoloration is 80 DEG C, and with stirring in decolorization.
3. the method for solvent crystallisation by cooling separation 4- cyanopyridine as described in claim 1, which is characterized in that the crystallizer
Operating temperature range be 50 ~ 5 DEG C, operating pressure is normal pressure.
4. the method for solvent crystallisation by cooling separation 4- cyanopyridine as described in claim 1, which is characterized in that the filter
Operation temperature be 0 ~ 5 DEG C, operating pressure is normal pressure.
5. the method for solvent crystallisation by cooling separation 4- cyanopyridine as described in claim 1, which is characterized in that step (3) institute
Stating cooling rate is 0.05 ~ 0.3 DEG C/min.
6. the method for solvent crystallisation by cooling separation 4- cyanopyridine as described in claim 1, which is characterized in that the crystallizer
With agitating device.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201810673365.9A CN108997211A (en) | 2018-06-27 | 2018-06-27 | A kind of method of solvent crystallisation by cooling separation 4- cyanopyridine |
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| CN201810673365.9A CN108997211A (en) | 2018-06-27 | 2018-06-27 | A kind of method of solvent crystallisation by cooling separation 4- cyanopyridine |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110746352A (en) * | 2019-11-11 | 2020-02-04 | 安徽瑞邦生物科技有限公司 | Method for separating 4-cyanopyridine by solvent cooling crystallization |
| BE1027319B1 (en) * | 2019-08-01 | 2021-01-13 | Anhui Redpont Biotechnology Co Ltd | Process for the purification of 4-cyanopyridine by melt crystallization |
| CN114539143A (en) * | 2022-01-28 | 2022-05-27 | 安徽瑞邦生物科技有限公司 | Purification method of 4-cyanopyridine |
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| CN103467370A (en) * | 2013-09-12 | 2013-12-25 | 南通天泽化工有限公司 | Synthesis method of cyanopyridine and derivatives thereof |
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Cited By (4)
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|---|---|---|---|---|
| BE1027319B1 (en) * | 2019-08-01 | 2021-01-13 | Anhui Redpont Biotechnology Co Ltd | Process for the purification of 4-cyanopyridine by melt crystallization |
| CN110746352A (en) * | 2019-11-11 | 2020-02-04 | 安徽瑞邦生物科技有限公司 | Method for separating 4-cyanopyridine by solvent cooling crystallization |
| CN110746352B (en) * | 2019-11-11 | 2023-03-14 | 安徽瑞邦生物科技有限公司 | Method for separating 4-cyanopyridine by solvent cooling crystallization |
| CN114539143A (en) * | 2022-01-28 | 2022-05-27 | 安徽瑞邦生物科技有限公司 | Purification method of 4-cyanopyridine |
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Application publication date: 20181214 |