CN103755661A - Separating and refining method of 2-chloro-5-chloromethylthiazole - Google Patents
Separating and refining method of 2-chloro-5-chloromethylthiazole Download PDFInfo
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- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or 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
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Abstract
The invention relates to a separating and refining method of 2-chloro-5-chloromethylthiazole. High-purity 2-chloro-5-chloromethylthiazole is prepared through a crystallization method by taking crude 2-chloro-5-chloromethylthiazole as a raw material. The method comprises the following steps: (1) washing with water; (2) performing adsorbing and color-removing; (3) performing pressure filtration; (4) desolventizing; (5) adding an organic solvent; (6) crystallizing with a crystallization device, heating and melting; collecting to obtain high-purity 2-chloro-5-chloromethylthiazole. High-purity 2-chloro-5-chloromethylthiazole is prepared through the crystallization method of the self-made crystallization device according to the characteristics of low melting point of 2-chloro-5-chloromethylthiazole and high melting point of impurities. The separating method is simple, the production purity is high, the quality is stable, the energy consumption is low, the three-waste output is low, and the green chemical industry development requirements are met.
Description
Technical field
The present invention relates to a kind of separation and refining method of 2-chloro-5-chloromethyl thiazole, belong to fine chemical technology field.
Background technology
The character of 1.1 2-chloro-5-chloromethyl thiazoles and purposes
English name: 2-Chloro-5-chloromethylthiazole CAS:105827-91-6
Molecular weight: 168; Fusing point: 29.5 °~30.0 ℃
Structural formula:
Industrial goods content: 98%, weak yellow liquid.
2-chloro-5-chloromethyl thiazole is the important intermediate of synthetic s-generation anabasine insecticide Diacloden, clothianidin.
The Technology of 1.2 existing preparation 2-chloro-5-chloromethyl thiazoles and the subject matter of existence
At present, the Technology of refining 2-chloro-5-chloromethyl thiazole mainly contains following two kinds.
Directly rectification method: the main reaction of synthetic 2-chloro-5-chloromethyl thiazole is directly carried out rectification under vacuum after having reacted, and by the variation of cut temperature, fraction in intercepting, can obtain the product of content in 98.0% left and right.
Hydrochloric acid salt forming method: be mainly utilize 2-chloro-5-chloromethyl thiazole can with hydrochloric acid in hydrogenchloride salify, and the not characteristic of salify of impurity, through salify, layering, extraction, the mode of rectifying obtains the product of content >99.0%.
The problem that these separation methods exist is as follows:
Foreign matter content is high, unstable product quality: during direct rectifying, because the boiling point of impurity and 2-chloro-5-chloromethyl thiazole approaches, not easily separated, cause product content not high, if rising stage number, 2-chloro-5-chloromethyl thiazole has again the characteristic of temperature-sensitive, and the level of residue that distillation obtains increases greatly.
Wastewater flow rate is large, and waste water is difficult: hydrochloric acid salt forming method utilizes product and hydrogenchloride salify, and the not characteristic of salify of impurity separates both, then obtains high-content product through rectifying.What in salification process, use is more than 36% concentrated hydrochloric acid, in the process of 2-chloro-5-chloromethyl thiazole hydrochloride hydrolysis, needs a large amount of water to dilute, and recycling organic solvent extracts 2-chloro-5-chloromethyl thiazole from diluted acid.The a large amount of dilute acid concentrations that form are in 18% left and right, and a large amount of organism is contained in the inside, and the recycling cost of this part diluted acid is very high, and difficulty is very large.
In sum, the novel method of research and develop that a kind of product purity is high, steady quality, separation method is simple, energy consumption is low, three wastes generation is little separation and purification 2-chloro-5-chloromethyl thiazole crude product being prepared high purity 2-chloro-5-chloromethyl thiazole is particularly important.
Summary of the invention
The object of this invention is to provide a kind of refining 2-chloro-5-chloromethyl thiazole crude product and prepare the novel method of high purity 2-chloro-5-chloromethyl thiazole.Be specially a kind of preparation method of high purity 2-chloro-5-chloromethyl thiazole, this separation method is simple, product purity is high, steady quality, separation method is simple, energy consumption is low, three wastes generation is little, is a kind of preparation method who meets green chemical industry demand for development.
2-chloro-5-chloromethyl thiazole crude product: after 2-chloro-5-chloromethyl thiazole building-up reactions completes, by the organic phase obtaining after solvent underpressure distillation, 2-chloro-5-chloromethyl thiazole content 78~80%.
The technical scheme that realizes above-mentioned purpose is:
A process for purification for 2-chloro-5-chloromethyl thiazole, take 2-chloro-5-chloromethyl thiazole crude product as raw material, prepares highly purified 2-chloro-5-chloromethyl thiazole by crystallization process, and step is as follows.
(1) washing: in washing kettle, in solvent, add in batches water to wash 2-chloro-5-chloromethyl thiazole dissolving crude product, pH value=6~7 of washing organic phase;
(2) absorption removes look: in the organic phase obtaining to step (1), add decolorizing adsorbent, keep stirring certain hour under certain temperature, become light yellow to mother liquor color from deep yellow;
(3) press filtration: material is transferred to filter-pressing cauldron, carries out press filtration, the faint yellow organic phase being press-filtered out enters holding tank, and the filter cake in filter-pressing cauldron is transferred to other equipment, and preferably regenerates to reuse;
(4) precipitation: the material in step (3) holding tank is transferred to precipitation still, and precipitation reduces pressure in the situation that keeping certain pressure and certain temperature;
(5) add organic solvent: in precipitation still, add organic solvent, stir, keep 40 ℃ of left and right of temperature of charge;
(6) crystallization apparatus crystallization, intensification fusing: the material in precipitation still is transferred to the crystallization apparatus that can overturn, pass through crystallisation by cooling, be warming up to the temperature slightly higher than fusing point and be incubated sweating again, upset crystallization apparatus, makes material be poured onto screen plate, filters; Be warmed up to fusing point, all solids in melting plant, collects and obtains highly purified 2-chloro-5-chloromethyl thiazole again.
As of the present invention preferred, the solvent using in step (1) is one or more mixed solutions in methylene dichloride, ethylene dichloride, trichloromethane, toluene, ethyl acetate.
As present invention further optimization, the solvent using in step (1) is preferably a kind of or its mixed solution in toluene, ethylene dichloride.
As of the present invention preferred, in step (2), decolorizing adsorbent is the composition of one or more adsorbents such as molecular sieve, silica gel, gac, macroporous adsorbent resin; The mass ratio of decolorizing adsorbent and material is 1~25:100, more preferably 5~15:100; Decolorization adsorption temperature is 10~90 ℃, more preferably 25~60 ℃; Churning time is 1~6 hour, more preferably 3~5 hours.
As of the present invention preferred, in step (4), precipitation pressure is-0.05~0.095bar, more preferably-0.08~0.095bar; Precipitation temperature is 40~100 ℃, more preferably 50~85 ℃; Preferably distilling off solvent is directly applied mechanically, in step (1), dissolved 2-chloro-5-chloromethyl thiazole crude product.
As of the present invention preferred, in step (5), organic solvent is acetone, methylene dichloride, 1,2-ethylene dichloride, chloroform, methyl alcohol, ethanol, ethyl acetate, N, the composition of one or more organic solvents such as dinethylformamide, dimethyl sulfoxide (DMSO), N-Methyl pyrrolidone, be preferably the composition of one or more solvents in methyl alcohol, ethyl acetate, methylene dichloride, N-Methyl pyrrolidone, more preferably in the composition of methyl alcohol, ethyl acetate, methylene dichloride, two kinds of solvents of N-Methyl pyrrolidone, volume ratio is 1:5~5:1, more preferably 1:2~2:1; The mass ratio of organic solvent and material is 1~50:150, more preferably 10~25:150.As of the present invention preferred, the crystallization apparatus that in step (6), use can be overturn, comprise kettle (1), mother liquor opening for feed (2), be arranged in kettle (1) and kettle (1) vertically can be divided into two-part screen plate (3), be arranged at the rotating shaft (4) of the outside horizontal direction of kettle (1), from kettle (1) outside, extend to the inner dwang (5) of kettle (1), discharge port (6), it is characterized in that: mother liquor opening for feed (2) and dwang (5) are positioned at a side of screen plate (3), discharge port (6) is positioned at the opposite side of screen plate (3), dwang (5) is vertical with screen plate (3) and can be mobile with respect to screen plate (3), and dwang (5) front end is equipped with the cross bar (7) that is parallel to screen plate.
As present invention further optimization, at the upper connection of rotating device of rotating shaft (4), can be by whole kettle (1) take rotating shaft (4) as rotation axis Rotate 180 °.As present invention further optimization, dwang (5) is positioned at the medium position of the horizontal direction of kettle (1), and the maximum of dwang (5) stretches into distance and determines according to the size of kettle (1) design; Cross bar (7) is flat-shaped, and length regulates according to the number of material.
As of the present invention further preferred, preferably 10~30 centimetres of cross bar (7) length, the maximum of telescopic rotary bar (5) stretches into distance to be advisable apart from (3) 2~5 centimetres of screen plates.
As present invention further optimization, other parts of kettle (1) bottom are level and smooth crystallising part, screen plate (3) is installed on kettle (1) top, directly over screen plate (3), be provided with discharge port (6), screen plate (3) has certain order number, order number is preferably: 50~800 orders, more preferably 350~500 orders.As present invention further optimization, kettle (1), with chuck, can pass into the hot and cold medium between-30~180 ℃; The setup of entrances and exits of hot and cold medium is in the adjacent locations of rotating shaft (4).
As present invention further optimization, open dwang (5), its rotation is also mobile to screen plate (3), and front end is equipped with the cross bar (7) that is parallel to screen plate upper screen plate (3) material of piling up is bulldozed.
The mechanism of sweating (sweating) effect is that crystal is maintained than at the slightly high temperature of its fusing point, allows the low melting point impurity of crystals constantly melt and to flow out, thereby crystal is purified.
The present invention is by utilizing 2-chloro-5-chloromethyl thiazole fusing point low, and the characteristic that impurity fusing point is high, prepares highly purified 2-chloro-5-chloromethyl thiazole by the method for self-control crystallization apparatus crystallization.Separation method of the present invention is simple, product purity is high, steady quality, separation method is simple, energy consumption is low, three wastes generation is little, is a kind of preparation method who meets green chemical industry demand for development.
Accompanying drawing explanation
Fig. 1 is process flow sheet of the present invention
Fig. 2 is the crystallization apparatus schematic diagram using in crystallisation process of the present invention
Fig. 3 is the schematic diagram after 180 ° of the crystallization apparatus upsets used in crystallisation process of the present invention
Element and Reference numeral:
1, kettle; 2, mother liquor opening for feed; 3, screen plate; 4, rotating shaft; 5, dwang; 6 discharge ports; 7, cross bar.
Embodiment
Embodiment 1
(1) washing: in washing kettle, be dissolved in 300kg ethylene dichloride in 400kg2-chloro-5-chloromethyl thiazole crude product, add in batches 900kg water to wash, pH value=6~7 of washing organic phase, after washing, separate lower floor's organic phase;
(2) absorption removes look: in the material obtaining to step (1), add 50kg gac, stir 3 hours at 40 ℃, become light yellow to mother liquor color from deep yellow;
(3) press filtration: the material that step (2) is obtained is transferred to filter-pressing cauldron, carries out press filtration, the faint yellow material being press-filtered out enters holding tank;
(4) precipitation: the material in step (3) holding tank is transferred to precipitation still, and under the pressure of-0.06~-0.07bar, 50~60 ℃ distill out ethylene dichloride, obtain ethylene dichloride and can directly overlap for step (1) as dissolution solvent;
(5) add compounded organic solvent: in precipitation still, add 50kg compounded organic solvent methyl alcohol: methylene dichloride=1:1, the organic solvent of (volume ratio), stirs, keep 40 ℃ of left and right of temperature of charge;
(6) crystallization apparatus crystallization, intensification fusing: the material in precipitation still is transferred to the kettle 1 of the crystallization apparatus that can overturn, slowly passes into 5 ℃ of cold water in chuck, make material in 3 hours, be cooled to 5~10 ℃, crystallization finishes; In chuck, slowly pass into 25~32 ℃ of warm water, make crystallized stock insulation 2 hours, after insulation finishes, 1 to 180 ° of kettle slowly overturns take rotating shaft 4 as rotation axis, material is slowly poured onto on screen plate 3, open dwang 5, its rotation is also moved to screen plate 3, and the cross bar 7 of its front end is bulldozed the material that is deposited in screen plate 3 surfaces, open vacuum, carry out suction filtration, the material that suction filtration goes out enters impurity holding tank, after suction filtration finishes for 2 hours; Kettle 1 chuck passes into 45~50 ℃ of warm water, by all material meltings in kettle, collects liquid phase and enters product-collecting tank, obtains highly purified 2-chloro-5-chloromethyl thiazole, content 99.6%.
Embodiment 2
(1) washing: in washing kettle, be dissolved in 150kg toluene in 400kg2-chloro-5-chloromethyl thiazole crude product, add in batches 900kg water to wash, pH value=6~7 of washing organic phase, after washing, separate lower floor's organic phase;
(2) absorption removes look: in the material obtaining to step (1), add 25kg macroporous adsorbent resin, stir 3 hours at 35 ℃, become light yellow to mother liquor color from deep yellow;
(3) press filtration: the material that step (2) is obtained is transferred to filter-pressing cauldron, carries out press filtration, the faint yellow material being press-filtered out enters holding tank;
(4) precipitation: the material in step (3) holding tank is transferred to precipitation still, and under the pressure of-0.08~-0.095bar, 65~75 ℃ go out toluene distillation, obtain toluene and can directly overlap for step (1) as dissolution solvent;
(5) add organic solvent: to adding 45kg ethyl acetate in precipitation still: N-Methyl pyrrolidone=1:4(volume ratio) organic solvent, stir, keep 40 ℃ of left and right of temperature of charge;
(6) crystallization apparatus crystallization, intensification fusing: the material in precipitation still is transferred to the kettle 1 of the crystallization apparatus that can overturn, slowly passes into 5 ℃ of cold water in chuck, make material in 3 hours, be cooled to 5~10 ℃, crystallization finishes; In chuck, slowly pass into 25~32 ℃ of warm water, make crystallized stock insulation 2 hours, after insulation finishes, 1 to 180 ° of kettle slowly overturns take rotating shaft 4 as rotation axis, material is slowly poured onto on screen plate 3, open dwang 5, its rotation is also moved to screen plate 3, and the cross bar 7 of front end is bulldozed the material that is deposited in screen plate 3 surfaces, open vacuum, carry out suction filtration, the material that suction filtration goes out enters impurity holding tank, after suction filtration finishes for 2 hours; Kettle 1 chuck passes into 45~50 ℃ of warm water, by all material meltings in kettle, collects liquid phase and enters product-collecting tank, obtains highly purified 2-chloro-5-chloromethyl thiazole, content 99.7%.
Embodiment 3
(1) washing: in washing kettle, be dissolved in 150kg toluene in 400kg2-chloro-5-chloromethyl thiazole crude product, add in batches 900kg water to wash, pH value=6~7 of washing organic phase, after washing, separate lower floor's organic phase;
(2) absorption removes look: in the material obtaining to step (1), add 30kg gac, stir 3 hours at 45 ℃, become light yellow to mother liquor color from deep yellow;
(3) press filtration: the material that step (2) is obtained is transferred to filter-pressing cauldron, carries out press filtration, the faint yellow material being press-filtered out enters holding tank;
(4) precipitation: the material in step (3) holding tank is transferred to precipitation still, and under the pressure of-0.08~-0.095bar, 65~75 ℃ go out toluene distillation, obtain toluene and can directly overlap for step (1) as dissolution solvent;
(5) add organic solvent: to adding 60kg methyl alcohol in precipitation still: N-Methyl pyrrolidone=1.25:1(volume ratio) organic solvent, stir, keep 40 ℃ of left and right of temperature of charge;
(6) crystallization apparatus crystallization, intensification fusing: the material in precipitation still is transferred to the kettle 1 of the crystallization apparatus that can overturn, slowly passes into 5 ℃ of cold water in chuck, make material in 3 hours, be cooled to 5~10 ℃, crystallization finishes; In chuck, slowly pass into 25~32 ℃ of warm water, make crystallized stock insulation 2 hours, after insulation finishes, 1 to 180 ° of kettle slowly overturns take rotating shaft 4 as rotation axis, material is slowly poured onto on screen plate 3, open dwang 5, its rotation is also moved to screen plate 3, and the cross bar 7 of front end is bulldozed the material that is deposited in screen plate 3 surfaces, open vacuum, carry out suction filtration, the material that suction filtration goes out enters impurity holding tank, after suction filtration finishes for 2 hours; Kettle 1 chuck passes into 45~50 ℃ of warm water, by all material meltings in kettle, collects liquid phase and enters product-collecting tank, obtains highly purified 2-chloro-5-chloromethyl thiazole, content 99.7%.
Claims (10)
1. a separation and refining method for 2-chloro-5-chloromethyl thiazole, is take 2-chloro-5-chloromethyl thiazole crude product as raw material, by crystallization process, prepares highly purified 2-chloro-5-chloromethyl thiazole, and step is as follows:
(1) washing: in washing kettle, in solvent, add in batches water to wash 2-chloro-5-chloromethyl thiazole dissolving crude product, pH value=6~7 of washing organic phase;
(2) absorption removes look: in the organic phase obtaining to step (1), add decolorizing adsorbent, keep stirring certain hour under certain temperature, become light yellow to mother liquor color from deep yellow;
(3) press filtration: material is transferred to filter-pressing cauldron, carries out press filtration, the faint yellow organic phase being press-filtered out enters holding tank, and the filter cake in filter-pressing cauldron is transferred to other equipment, and preferably regenerates to reuse;
(4) precipitation: the material in step (3) holding tank is transferred to precipitation still, and precipitation reduces pressure in the situation that keeping certain pressure and certain temperature;
(5) add organic solvent; In precipitation still, add organic solvent, stir, keep 40 ℃ of left and right of temperature of charge;
(6) crystallization apparatus crystallization, intensification fusing: the material in precipitation still is transferred to the crystallization apparatus that can overturn, pass through crystallisation by cooling, be warming up to the temperature slightly higher than fusing point and be incubated sweating again, upset crystallization apparatus, makes material be poured onto screen plate, filters; Be warmed up to fusing point, all solids in melting plant, collects and obtains highly purified 2-chloro-5-chloromethyl thiazole again.
2. according to the separation and refining method of the 2-chloro-5-chloromethyl thiazole described in claims 1, it is characterized in that: in step (1), solvent is one or more mixed solutions in methylene dichloride, ethylene dichloride, trichloromethane, toluene, ethyl acetate; Be preferably a kind of or its mixed solution in toluene, ethylene dichloride.
3. according to the separation and refining method of the 2-chloro-5-chloromethyl thiazole described in claims 1 or 2, it is characterized in that: step (2) decolorizing adsorbent is the composition of one or more adsorbents such as molecular sieve, silica gel, gac, macroporous adsorbent resin; The mass ratio of decolorizing adsorbent and material is 1~25:100, is preferably 5~15:100; Decolorization adsorption temperature is 10~90 ℃, is preferably 25~60 ℃; Churning time is 1~6 hour, is preferably 3~5 hours.
4. according to the separation and refining method of the 2-chloro-5-chloromethyl thiazole described in claims 1-3 any one, it is characterized in that: in step (4), precipitation pressure is-0.05~-0.095bar, is preferably-0.08~-0.095bar; Precipitation temperature is 40~100 ℃, is preferably 50~85 ℃; Preferably distilling off solvent is directly applied mechanically, in step (1), dissolved 2-chloro-5-chloromethyl thiazole crude product.
5. according to the separation and refining method of the 2-chloro-5-chloromethyl thiazole described in claims 1-4 any one, it is characterized in that: step (5) organic solvent is acetone, methylene dichloride, 1, 2-ethylene dichloride, chloroform, methyl alcohol, ethanol, ethyl acetate, N, dinethylformamide, dimethyl sulfoxide (DMSO), the composition of one or more solvents such as N-Methyl pyrrolidone, be preferably methyl alcohol, ethyl acetate, methylene dichloride, the composition of one or more solvents in N-Methyl pyrrolidone, more preferably methyl alcohol, ethyl acetate, methylene dichloride, the composition of two kinds of solvents in N-Methyl pyrrolidone and volume ratio are 1:5~5:1, be preferably 1:2~2:1, the mass ratio of organic solvent and material is 1~50:150, is preferably 10~25:150.
6. according to the separation and refining method of the 2-chloro-5-chloromethyl thiazole described in claims 1-5 any one, it is characterized in that: the crystallizer that can overturn that step (6) is used comprises kettle (1), mother liquor opening for feed (2), be arranged in kettle (1) and kettle (1) vertically can be divided into two-part screen plate (3), be arranged at the rotating shaft (4) of the outside horizontal direction of kettle (1), from kettle (1) outside, extend to the inner dwang (5) of interior kettle (1), discharge port (6), it is characterized in that: mother liquor opening for feed (2) and dwang (5) are positioned at screen plate (3) one sides, discharge port (6) is positioned at screen plate (3) opposite side, dwang (5) is vertical with screen plate (3) and can be mobile with respect to screen plate (3), and dwang (5) front end is equipped with the cross bar (7) that is parallel to screen plate.
7. according to the separation and refining method of the 2-chloro-5-chloromethyl thiazole described in claims 6, it is characterized in that:
At the upper connection of rotating device of rotating shaft (4), can be by whole kettle (1) take rotating shaft (4) as rotation axis Rotate 180 °.
8. according to the separation and refining method of the 2-chloro-5-chloromethyl thiazole described in claims 6 or 7, it is characterized in that: dwang (5) is positioned at the medium position of the horizontal direction of kettle (1), the maximum of rotatable bar (5) stretches into distance and determines according to the size of kettle (1) design; Cross bar (7) is flat-shaped, and length regulates according to the number of material; Preferably 10~30 centimetres of cross bar (7) length, the maximum of telescopic rotary bar (5) stretches into distance to be advisable apart from (3) 2~5 centimetres of screen plates.
9. according to the separation and refining method of the 2-chloro-5-chloromethyl thiazole described in claims 6-8 any one, it is characterized in that: other parts of kettle (1) bottom are level and smooth crystallising part, screen plate (3) is installed on kettle (1) top, directly over screen plate (3), be provided with discharge port (6), screen plate (3) has certain order number, order number is preferably: 50~800 orders, more preferably 350~500 orders.
10. according to the separation and refining method of the 2-chloro-5-chloromethyl thiazole described in claims 6-9 any one, it is characterized in that:
Kettle (1), with chuck, can pass into the hot and cold medium between-30~180 ℃; The setup of entrances and exits of hot and cold medium is in the adjacent locations of rotating shaft (4).
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Cited By (3)
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CN112480023A (en) * | 2020-12-09 | 2021-03-12 | 怀仁市普惠生物科技有限公司 | Method for synthesizing dichloro pentachloromethyl thiazole |
CN115109008A (en) * | 2022-07-05 | 2022-09-27 | 山西玉龙化工有限公司 | Method for prolonging reuse of toluene solvent in preparation of 2-chloro-5-chloromethyl thiazole |
CN115636800A (en) * | 2022-10-31 | 2023-01-24 | 河北美邦膜科技有限公司 | Purification method of dichloro pentachloromethyl thiazole |
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张海滨等: "2-氯-5-氯甲基-1,3-噻唑提纯新方法", 《精细化工中间体》 * |
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CN112480023A (en) * | 2020-12-09 | 2021-03-12 | 怀仁市普惠生物科技有限公司 | Method for synthesizing dichloro pentachloromethyl thiazole |
CN115109008A (en) * | 2022-07-05 | 2022-09-27 | 山西玉龙化工有限公司 | Method for prolonging reuse of toluene solvent in preparation of 2-chloro-5-chloromethyl thiazole |
CN115109008B (en) * | 2022-07-05 | 2024-02-06 | 山西玉龙化工有限公司 | Method for prolonging toluene solvent application in preparation of 2-chloro-5-chloromethylthiazole |
CN115636800A (en) * | 2022-10-31 | 2023-01-24 | 河北美邦膜科技有限公司 | Purification method of dichloro pentachloromethyl thiazole |
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