CN101962344B - Method for purifying tetrachloroisophthalonitrile crystal - Google Patents
Method for purifying tetrachloroisophthalonitrile crystal Download PDFInfo
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- CN101962344B CN101962344B CN200910055257.6A CN200910055257A CN101962344B CN 101962344 B CN101962344 B CN 101962344B CN 200910055257 A CN200910055257 A CN 200910055257A CN 101962344 B CN101962344 B CN 101962344B
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- CN
- China
- Prior art keywords
- purifying
- temperature
- tetrachloroisophthalonitrile
- termil
- toluene
- Prior art date
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- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 21
- 239000013078 crystal Substances 0.000 title abstract 2
- 239000012535 impurity Substances 0.000 claims abstract description 13
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002994 raw material Substances 0.000 claims abstract description 9
- 238000001035 drying Methods 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 55
- 238000004090 dissolution Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000009413 insulation Methods 0.000 claims description 6
- 239000002826 coolant Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 8
- 238000000746 purification Methods 0.000 abstract description 8
- 239000000463 material Substances 0.000 abstract description 5
- 238000003756 stirring Methods 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 239000000498 cooling water Substances 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 238000007670 refining Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000002791 soaking Methods 0.000 description 3
- 238000012797 qualification Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000005747 Chlorothalonil Substances 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000750 industrial fungicide Substances 0.000 description 1
- LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 231100000817 safety factor Toxicity 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- -1 sterilant Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for purifying tetrachloroisophthalonitrile crystal, which comprises the following steps of: putting a harmful substance-containing raw material tetrachloroisophthalonitrile into a dissolving kettle filled with an organic solvent, and starting a stirring device for stirring and mixing; raising the temperature in the dissolving kettle to between 85 and 90 DEG C, keeping the temperature and reacting for 1 to 1.5 hours, and reducing the temperature of the dissolving kettle to between 20 and 30 DEG C by using cooling water; and finally, separating by using a centrifugal machine, drying the obtained wet material to prepare finished tetrachloroisophthalonitrile. Compared with the prior art, the method has the advantages of simple operation, higher purification rate, high bioactivity of the obtained product, purity of more than or equal to 99 percent, yield of more than or equal to 95 percent, main impurity hexachlorobenzene content of less than or equal to 10mg/kg and dimethylbenzene undissolved substance content of less than 0.3 percent.
Description
Technical field
The present invention relates to a kind of method of crystallization and purification, especially relate to a kind of method of purifying tetrachloroisophthalcrystale crystale.
Background technology
Termil is through superchlorination, to be obtained in fluidized-bed by Isophthalodinitrile.Termil, English chlorothalonil by name, popular name m-tetrachlorophthalodinitrile, is a kind of wide-spectrum bactericide of high-efficiency low-toxicity, its Main Function is that prevention farm crop are subject to infecting of fungi; Also be used as the protective agent of industrial fungicide, fruit antistaling agent, sterilant, coating and cakingagent simultaneously.World market is significantly improved to the requirement of m-tetrachlorophthalodinitrile inner quality at present, except content and outward appearance, lay special stress on objectionable impurities hexachlorobenzene content is less than 10mg/kg, for also not having report can produce such product in reaction process, so can only be with refining the method for purifying.
Summary of the invention
Object of the present invention is exactly a kind of method that simple to operate, purifying tetrachloroisophthalcrystale crystale that purification rate is higher is provided in order to overcome the defect that above-mentioned prior art exists.
Object of the present invention can be achieved through the following technical solutions:
A kind of method of purifying tetrachloroisophthalcrystale crystale, it is characterized in that, the method comprises the following steps: the raw material termil that contains objectionable impurities is placed in to the dissolution kettle that organic solvent is housed, unlatching whipping appts is uniformly mixed, then the temperature in dissolution kettle is risen to 85-90 ℃, insulation reaction 1-1.5h, is then cooled to 20-30 ℃ with water coolant by dissolution kettle, finally use whizzer separated, the wet feed the obtaining termil that gets product after drying.
Described objectionable impurities is Perchlorobenzene.
In described raw material termil, the concentration expressed in percentage by weight of daconil M is 90-95%.
Described organic solvent is toluene.
Compared with prior art, the present invention is simple to operate, and purification rate is higher, and the product biological activity of acquisition is high, purity >=99%, yield >=95%, major impurity hexachlorobenzene content≤10mg/kg, dimethylbenzene insolubles < 0.3%.
Accompanying drawing explanation
Fig. 1 is the process flow sheet of embodiment 1.
Embodiment
Below in conjunction with the drawings and specific embodiments, the present invention is described in detail.
Embodiment 1
A kind of method of purifying tetrachloroisophthalcrystale crystale, the schema of the method as shown in Figure 1, comprise the following steps: the raw material termil that contains objectionable impurities Perchlorobenzene is placed in to the dissolution kettle that toluene is housed, the concentration expressed in percentage by weight of daconil M is 90%, objectionable impurities hexachlorobenzene content is 40mg/kg, unlatching whipping appts is uniformly mixed, then the temperature in dissolution kettle is risen to 85 ℃, insulation reaction 1h, then with water coolant, dissolution kettle is cooled to 20 ℃, finally use whizzer separated, the wet feed the obtaining termil that gets product after drying, centrifugal remaining liquid is collected raffinate wherein through precipitation, remainder enters condenser condenses, be placed in again solvent trough, add after new toluene, be directed into continuation in dissolution kettle and dissolve raw material termil.
Under certain conditions of mixture ratios, make material dissolve completely, must improve temperature, consider holding capacity and the safety factors of equipment, by operation, regulate and control, temperature is risen to 85 ℃, more termil (m-tetrachlorophthalodinitrile) is dissolved.
If the in the situation that of solvent burden ratio deficiency, material can not dissolve completely, but in high-temperature zone, the part of failing to dissolve relatively easily becomes small-particle from macrobead, thereby the part Perchlorobenzene (HCB) adsorbing in material is separated out, molten in toluene.From lab scale situation, also can find out, in the situation that other condition is identical, high-temperature zone soaking time is long, and the HCB content of product is low, and high-temperature zone soaking time is short, and the HCB content of product is high.Therefore increase high-temperature zone soaking time, by original 0.5h, be increased to 1h.
At present, centrifuging temperature is 25 ℃, by statistics, finds, is cooled to 25 ℃ from 30 ℃, on average need use 1-1.5h.Because: in the time of 25 ℃, the solubleness of m-tetrachlorophthalodinitrile in toluene is about 5.5g, and in the time of 30 ℃, the solubleness of m-tetrachlorophthalodinitrile in toluene is about 6.14g, and poor solubility is apart from little; When low temperature, crystallization rate is very low; The residence time of toluene after centrifugal in mother liquor pond is very short, and at low temperatures, in the very short time, the material that can separate out seldom, can not cause very large impact to yield, 30 ℃ centrifugal, the time of therefore saving can be used for high-temperature zone insulation.
Because the fusing point high (being about 230 ℃) of HCB, solubleness in toluene are very large (25 ℃ time, be about 120g/kg), therefore, after centrifugal, in product, the residual quantity of toluene is very large on the impact of quality product, therefore under existence conditions, strengthen centrifugally operated, reduce the residual quantity of toluene in product as far as possible.
In toluene, the content of HCB is very large on the impact of m-tetrachlorophthalodinitrile, in lab scale, due to the impact of filtering, goes out m-tetrachlorophthalodinitrile during crystallization and contain HCB and exceed 10mg/kg when HCB content is high in toluene.Aborning, toluene is only applied mechanically once, then carries out falling film evaporation precipitation, so just the HCB precipitation in toluene can be removed.
Testing data is as following table:
From upper table data, can find out, in the situation that other condition is constant, the HCB containing in m-tetrachlorophthalodinitrile while refining for the third time has defective phenomenon to occur, therefore cancel for the third time, refines, and only retains the refining purification of secondary (a time fresh toluene is once applied mechanically toluene).
(1) twice refining purification efficiency: (2.682/2.8) * 100%=95.7%
(2) twice refining purification qualification rate: 100% (HCB < 10ppm)
(3) twice refining purification dimethylbenzene qualification rate reach 100% (dimethylbenzene insolubles < 0.3%)
Embodiment 2
A kind of method of purifying tetrachloroisophthalcrystale crystale, the method comprises the following steps: the raw material termil that contains objectionable impurities Perchlorobenzene is placed in to the dissolution kettle that toluene is housed, the concentration expressed in percentage by weight of daconil M is 95%, objectionable impurities hexachlorobenzene content is 200mg/kg, unlatching whipping appts is uniformly mixed, then the temperature in dissolution kettle is risen to 90 ℃, insulation reaction 1.5h, then with water coolant, dissolution kettle is cooled to 30 ℃, finally use whizzer separated, the wet feed the obtaining termil that gets product after drying.
Embodiment 3
A kind of method of purifying tetrachloroisophthalcrystale crystale, the method comprises the following steps: the raw material termil that contains objectionable impurities Perchlorobenzene is placed in to the dissolution kettle that toluene is housed, the concentration expressed in percentage by weight of daconil M is 92%, objectionable impurities hexachlorobenzene content is 150mg/kg, unlatching whipping appts is uniformly mixed, then the temperature in dissolution kettle is risen to 88 ℃, insulation reaction 1.5h, then with water coolant, dissolution kettle is cooled to 25 ℃, finally use whizzer separated, the wet feed the obtaining termil that gets product after drying.
Claims (3)
1. the method for a purifying tetrachloroisophthalcrystale crystale, it is characterized in that, the method comprises the following steps: the raw material termil that contains objectionable impurities is placed in to the dissolution kettle that organic solvent is housed, unlatching whipping appts is uniformly mixed, then the temperature in dissolution kettle is risen to 85-90 ℃, insulation reaction 1-1.5h, then with water coolant, dissolution kettle is cooled to 20-30 ℃, finally use whizzer separated, the wet feed the obtaining termil that gets product after drying, described objectionable impurities is Perchlorobenzene.
2. the method for a kind of purifying tetrachloroisophthalcrystale crystale according to claim 1, is characterized in that, in described raw material termil, the concentration expressed in percentage by weight of daconil M is 90-95%.
3. the method for a kind of purifying tetrachloroisophthalcrystale crystale according to claim 1, is characterized in that, described organic solvent is toluene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910055257.6A CN101962344B (en) | 2009-07-23 | 2009-07-23 | Method for purifying tetrachloroisophthalonitrile crystal |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910055257.6A CN101962344B (en) | 2009-07-23 | 2009-07-23 | Method for purifying tetrachloroisophthalonitrile crystal |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101962344A CN101962344A (en) | 2011-02-02 |
| CN101962344B true CN101962344B (en) | 2014-07-16 |
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| CN200910055257.6A Expired - Fee Related CN101962344B (en) | 2009-07-23 | 2009-07-23 | Method for purifying tetrachloroisophthalonitrile crystal |
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Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447407B (en) * | 2014-12-08 | 2016-08-17 | 江阴苏利化学股份有限公司 | A kind of method preparing the hexachlorobenzene content Bravo less than 10ppm |
| CN108721935B (en) * | 2017-04-14 | 2021-02-09 | 上海泰禾国际贸易有限公司 | Trapping device and process for production of o-chlorobenzonitrile |
| CN108329235B (en) * | 2018-03-02 | 2020-10-02 | 天津赛普泰克科技有限公司 | Process for producing high-purity chlorothalonil |
| CN109265365B (en) * | 2018-12-06 | 2021-11-19 | 江苏新河农用化工有限公司 | Continuous rectification and purification process for high-content chlorothalonil |
| CN109438284B (en) * | 2018-12-06 | 2021-12-07 | 江苏新河农用化工有限公司 | Continuous rectification purification process for low-content chlorothalonil |
| CN109796371A (en) * | 2019-02-22 | 2019-05-24 | 江苏新河农用化工有限公司 | A kind of crystallization and purification technique of Bravo |
| CN116199601B (en) * | 2023-05-06 | 2023-08-11 | 山东大成生物化工有限公司 | Refining and purifying process of high-content chlorothalonil |
-
2009
- 2009-07-23 CN CN200910055257.6A patent/CN101962344B/en not_active Expired - Fee Related
Non-Patent Citations (2)
| Title |
|---|
| 低含量百菌清原药的提纯;杨建春;《湖南化工》;19990831;第29卷(第4期);29-30 * |
| 杨建春.低含量百菌清原药的提纯.《湖南化工》.1999,第29卷(第4期),29-30. |
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| CN101962344A (en) | 2011-02-02 |
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Granted publication date: 20140716 |