CN103755661B - A kind of separation and refining method of 2-chloro-5-chloromethyl thiazole - Google Patents
A kind of separation and refining method of 2-chloro-5-chloromethyl thiazole Download PDFInfo
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- CN103755661B CN103755661B CN201410045648.0A CN201410045648A CN103755661B CN 103755661 B CN103755661 B CN 103755661B CN 201410045648 A CN201410045648 A CN 201410045648A CN 103755661 B CN103755661 B CN 103755661B
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- 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 present invention relates to the separation and refining method of a kind of 2 chlorine 5 5-chloromethyl thiazoles, it is with 2 chlorine 5 5-chloromethyl thiazole crude products as raw material, preparing highly purified 2 chlorine 5 5-chloromethyl thiazoles by crystallization process, through step (1) washing, (2) absorption removes color, (3) filter pressing, (4) precipitation, (5) add organic solvent, the crystallization of (6) crystallization apparatus, heat up fusing；Collection obtains highly purified 2 chlorine 5 5-chloromethyl thiazoles.The present invention is by utilizing 2 chlorine 5 5-chloromethyl thiazole fusing points low, and the characteristic that impurity fusing point is high, the method crystallized by self-control crystallization apparatus prepares highly purified 2 chlorine 5 5-chloromethyl thiazoles.The separation method of the present invention is simple, product purity is high, steady quality, separation method are simple, energy consumption is low, three wastes generation amount is little, is a kind of preparation method meeting green chemical industry demand for development.
Description
Technical field
The present invention relates to the separation and refining method of a kind of 2-chloro-5-chloromethyl thiazole, belong to technical field of fine.
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 DEG C
Structural formula:
Industrial goods content: 98%, weak yellow liquid.
2-chloro-5-chloromethyl thiazole is synthesis second filial generation anabasine insecticide Diacloden, the important intermediate of clothianidin.
The 1.2 existing Technology preparing 2-chloro-5-chloromethyl thiazole and the subject matters of existence
At present, the Technology of refined 2-chloro-5-chloromethyl thiazole mainly has following two.
Directly rectification method: after the primary response of synthesis 2-chloro-5-chloromethyl thiazole has reacted, directly carry out rectification under vacuum,
By the change of fraction temperature, fraction in intercepting, the product that content is about 98.0% can be obtained.
Hydrochloric acid salt forming method: salt can be become with the hydrogen chloride in hydrochloric acid mainly by 2-chloro-5-chloromethyl thiazole, and impurity is not
Become the characteristic of salt, pass through into salt, layering, extract, the mode of rectification obtains content > product of 99.0%.
The problem that these separation methods exist is as follows:
Impurity content is high, unstable product quality: directly during rectification, due to the boiling of impurity Yu 2-chloro-5-chloromethyl thiazole
Point is close, is not readily separated, causes product content the highest, if rising high tray-number, 2-chloro-5-chloromethyl thiazole has again temperature-sensitive
Characteristic, the level of residue that distillation obtains is greatly increased.
Wastewater flow rate is big, and waste water is difficult: hydrochloric acid salt forming method utilizes product to become salt with hydrogen chloride, and impurity does not become the spy of salt
Property, both are separated, then obtains high-load product through rectification.The concentrated hydrochloric acid of more than 36% is used in salification process,
During the hydrolysis of 2-chloro-5-chloromethyl thiazole hydrochlorate, needing substantial amounts of water to be diluted, recycling organic solvent is by 2-
Chloro-5-chloromethyl thiazole extracts from diluted acid.The a large amount of dilute acid concentrations formed are about 18%, and the inside is contained substantial amounts of organic
Thing, the recycling cost of this part diluted acid is the highest, and difficulty is the biggest.
In sum, research and develop a kind of product purity height, steady quality, separation method is simple, energy consumption is low, three wastes generation amount is little
Separation and purification 2-chloro-5-chloromethyl thiazole crude product to prepare the new method of high-purity 2-chloro-5-chloromethyl thiazole particularly important.
Summary of the invention
It is an object of the invention to provide a kind of refined 2-chloro-5-chloromethyl thiazole crude product and prepare high-purity 2-chloro-5-chloromethane
The new method of base thiazole.Being specially the preparation method of a kind of high-purity 2-chloro-5-chloromethyl thiazole, this separation method is simple, product
Product purity height, steady quality, separation method is simple, energy consumption is low, three wastes generation amount is little, is that one meets green chemical industry demand for development
Preparation method.
2-chloro-5-chloromethyl thiazole crude product: after 2-chloro-5-chloromethyl thiazole synthetic reaction completes, distills solvent under reduced pressure
After the organic facies that obtains, 2-chloro-5-chloromethyl thiazole content 78～80%.
The technical scheme realizing above-mentioned purpose is:
The process for purification of a kind of 2-chloro-5-chloromethyl thiazole, with 2-chloro-5-chloromethyl thiazole crude product as raw material, by knot
Crystallization prepares highly purified 2-chloro-5-chloromethyl thiazole, and step is as follows.
(1) washing: in washing kettle, by 2-chloro-5-chloromethyl thiazole dissolving crude product in solvent, adds water in batches and enters
Row washing, pH value=6～7 of washing organic facies；
(2) absorption is except color: add decolorizing adsorbent in the organic facies that step (1) obtains, and keeps stirring under uniform temperature
Certain time, become light yellow to mother solution color from buff；
(3) filter pressing: transfer the material into filter-pressing cauldron, carries out filter pressing, and the faint yellow organic facies being press-filtered out enters collecting tank, pressure
Filter cake in filter still is transferred to other equipment, and preferably carries out regenerating with recycling；
(4) precipitation: the material in step (3) collecting tank is transferred to precipitation still, is keeping certain pressure and a constant temperature
The precipitation that reduces pressure is carried out in the case of degree；
(5) organic solvent is added: in precipitation still, add organic solvent, stir, keep temperature of charge about 40 DEG C；
(6) crystallization apparatus crystallization, intensification fusing: the material in precipitation still is transferred to the crystallization apparatus that can overturn, warp
Supercooling crystallizes, is warming up to the temperature more slightly higher than fusing point again and is incubated diaphoresis, overturns crystallization apparatus, makes material be poured onto filtration
Plate, filters；It is warmed up to more than fusing point again, all solids in melting plant, collect and obtain highly purified 2-chloro-5-chloromethane
Base thiazole.
Preferred as the present invention, the solvent used in step (1) is dichloromethane, dichloroethanes, chloroform, first
One or more mixed liquors in benzene, ethyl acetate.
It is preferably the one in toluene, dichloroethanes as the solvent used in present invention further optimization, step (1)
Or its mixed liquor.
Preferred as the present invention, in step (2), decolorizing adsorbent is molecular sieve, silica gel, activated carbon, macroporous adsorbent resin
Compositions Deng one or more adsorbents；The mass ratio of decolorizing adsorbent and material is 1～25:100, more preferably 5～
15:100；Decolorization adsorption temperature is 10～90 DEG C, more preferably 25～60 DEG C；Mixing time is 1～6 hour, more preferably 3～
5 hours.
Preferred as the present invention, in step (4), precipitation pressure is-0.05～0.095bar, more preferably-0.08～
0.095bar；Precipitation temperature is 40～100 DEG C, more preferably 50～85 DEG C；Preferably distilling off solvent is directly applied mechanically, in step
(1) 2-chloro-5-chloromethyl thiazole crude product is dissolved in.
Preferred as the present invention, in step (5) organic solvent be acetone, dichloromethane, 1,2-dichloroethanes, chloroform,
One or more are organic for methanol, ethanol, ethyl acetate, N,N-dimethylformamide, dimethyl sulfoxide, N-Methyl pyrrolidone etc.
The group of one or more solvents in the compositions of solvent, preferably methanol, ethyl acetate, dichloromethane, N-Methyl pyrrolidone
In compound, the more preferably compositions of methanol, ethyl acetate, dichloromethane, two kinds of solvents of N-Methyl pyrrolidone, volume ratio is
1:5～5:1, more preferably 1:2～2:1；Organic solvent is 1～50:150 with the mass ratio of material, more preferably 10～25:
150.Preferred as the present invention, uses the crystallization apparatus that can overturn, including kettle (1), mother liquor mouth in step (6)
(2), be arranged in kettle (1) and can be two-part screen plate (3) by kettle (1) vertical separation, be arranged at kettle (1) outside
Horizontal direction rotating shaft (4), extend to the internal rotation bar (5) of kettle (1), discharging opening (6) from kettle (1) is outside, it is special
Levy and be: mother liquor mouth (2) and rotation bar (5) are positioned at the side of screen plate (3), and discharging opening (6) is positioned at the another of screen plate (3)
Side；Rotation bar (5) is vertical with screen plate (3) and can move relative to screen plate (3), and rotates bar (5) front end equipped with parallel
Cross bar (7) in screen plate.
As present invention further optimization, rotating shaft (4) connects tumbler, can be by whole kettle (1) to turn
Axle (4) is that rotary shaft rotates 180 °.As present invention further optimization, rotation bar (5) is positioned at the horizontal direction of kettle (1)
Medium position, rotates depending on the maximum of bar (5) stretches into the size that distance designs according to kettle (1)；Cross bar (7) is flat-shaped, length
According to material number be adjusted.
Further preferred as the present invention, cross bar (7) length preferably 10～30 centimetres, telescopic rotary bar (5)
Maximum stretches into distance and is advisable with distance screen plate (3) 2～5 centimetres.
As present invention further optimization, other parts of kettle (1) bottom are smooth crystalline portion, on kettle (1)
Portion installs and is provided with discharging opening (6) directly over screen plate (3), screen plate (3), and screen plate (3) has certain mesh number, and mesh number is preferred
For: 50～800 mesh, more preferably 350～500 mesh.As present invention further optimization, kettle (1) is with chuck, Ke Yitong
Enter the hot and cold medium between-30～180 DEG C；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, opening and rotate bar (5), its rotation is also mobile to screen plate (3), front end equipped with
Upper for screen plate (3) material piled up is bulldozed by the cross bar (7) being parallel to screen plate.
The mechanism that diaphoresis (sweating) acts on is to be maintained by crystal at a temperature of more slightly higher than its fusing point, allows crystals
Low-melting impurities constantly melt and flow out, so that 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, by self-control crystallization dress
The method putting crystallization prepares highly purified 2-chloro-5-chloromethyl thiazole.The separation method of the present invention is simple, product purity is high, matter
Amount is stable, separation method is simple, energy consumption is low, three wastes generation amount is little, is a kind of preparation method meeting green chemical industry demand for development.
Accompanying drawing explanation
Fig. 1 is the process chart of the present invention
Fig. 2 is the crystallization apparatus schematic diagram used in crystallization process of the present invention
Fig. 3 is the schematic diagram after the crystallization apparatus used in crystallization process of the present invention overturns 180 °
Element and reference:
1, kettle；2, mother liquor mouth；3, screen plate；4, rotating shaft；5, bar is rotated；6 discharging openings；7, cross bar.
Detailed description of the invention
Embodiment 1
(1) washing: in washing kettle, be dissolved in 300kg dichloroethanes in 400kg2-chloro-5-chloromethyl thiazole crude product
In, add 900kg water in batches and wash, pH value=6～7 of washing organic facies, after washing, separate lower floor's organic facies；
(2) absorption is except color: add 50kg activated carbon in the material that step (1) obtains, stirring 3 hours at 40 DEG C, extremely
Mother solution color is become light yellow from buff；
(3) filter pressing: the material that step (2) obtains is transferred to filter-pressing cauldron, carries out filter pressing, the faint yellow material being press-filtered out enters
Enter collecting tank；
(4) precipitation: the material in step (3) collecting tank is transferred to precipitation still, at the pressure of-0.06～-0.07bar
Under, dichloroethanes is distilled out by 50～60 DEG C, obtains dichloroethanes and can directly overlap for step (1) as dissolution solvent；
(5) compounded organic solvent is added: addition 50kg compounded organic solvent methanol in precipitation still: dichloromethane=1:1,
The organic solvent of (volume ratio), stirs, and keeps temperature of charge about 40 DEG C.
(6) crystallization apparatus crystallization, intensification fusing: the material in precipitation still is transferred to the still of the crystallization apparatus that can overturn
Body 1, is slowly introducing 5 DEG C of cold water in chuck so that material was cooled to 5～10 DEG C in 3 hours, and crystallization terminates；In chuck slowly
It is passed through 25～32 DEG C of warm water, makes crystallized stock be incubated 2 hours, after insulation terminates, slowly overturn kettle 1 with rotating shaft 4 for rotary shaft
To 180 °, making material slowly be poured onto on screen plate 3, open and rotate bar 5, its rotation is also moved to screen plate 3, the horizontal stroke of its front end
The material being deposited in screen plate 3 surface is bulldozed by bar 7, opens vacuum, carries out sucking filtration, and the material that sucking filtration goes out enters impurity and collects
Tank, after sucking filtration terminates for 2 hours；Kettle 1 chuck is passed through 45～50 DEG C of warm water, by all material melts in kettle, collects liquid phase
Enter product collecting tank, obtain 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, point
Batch adds 900kg water and washes, pH value=6～7 of washing organic facies, after washing, separates lower floor's organic facies；
(2) absorption is except color: add 25kg macroporous adsorbent resin in the material that step (1) obtains, and stirs 3 little at 35 DEG C
Time, become light yellow to mother solution color from buff；
(3) filter pressing: the material that step (2) obtains is transferred to filter-pressing cauldron, carries out filter pressing, the faint yellow material being press-filtered out enters
Enter collecting tank；
(4) precipitation: the material in step (3) collecting tank is transferred to precipitation still, at the pressure of-0.08～-0.095bar
Under, toluene distillation is gone out by 65～75 DEG C, obtains toluene and can directly overlap for step (1) as dissolution solvent；
(5) organic solvent is added: addition 45kg ethyl acetate in precipitation still: N-Methyl pyrrolidone=1:4(volume ratio)
Organic solvent, stir, keep temperature of charge about 40 DEG C；
(6) crystallization apparatus crystallization, intensification fusing: the material in precipitation still is transferred to the still of the crystallization apparatus that can overturn
Body 1, is slowly introducing 5 DEG C of cold water in chuck so that material was cooled to 5～10 DEG C in 3 hours, and crystallization terminates；In chuck slowly
It is passed through 25～32 DEG C of warm water, makes crystallized stock be incubated 2 hours, after insulation terminates, slowly overturn kettle 1 with rotating shaft 4 for rotary shaft
To 180 °, making material slowly be poured onto on screen plate 3, open and rotate bar 5, its rotation is also moved to screen plate 3, the cross bar of front end
The material being deposited in screen plate 3 surface is bulldozed by 7, opens vacuum, carries out sucking filtration, and the material that sucking filtration goes out enters impurity collecting tank,
After sucking filtration terminates for 2 hours；Kettle 1 chuck is passed through 45～50 DEG C of warm water, by all material melts 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, point
Batch adds 900kg water and washes, pH value=6～7 of washing organic facies, after washing, separates lower floor's organic facies；
(2) absorption is except color: add 30kg activated carbon in the material that step (1) obtains, stirring 3 hours at 45 DEG C, extremely
Mother solution color is become light yellow from buff；
(3) filter pressing: the material that step (2) obtains is transferred to filter-pressing cauldron, carries out filter pressing, the faint yellow material being press-filtered out enters
Enter collecting tank；
(4) precipitation: the material in step (3) collecting tank is transferred to precipitation still, at the pressure of-0.08～-0.095bar
Under, toluene distillation is gone out by 65～75 DEG C, obtains toluene and can directly overlap for step (1) as dissolution solvent；
(5) organic solvent is added: addition 60kg methanol in precipitation still: N-Methyl pyrrolidone=1.25:1(volume ratio)
Organic solvent, stir, keep temperature of charge about 40 DEG C；
(6) crystallization apparatus crystallization, intensification fusing: the material in precipitation still is transferred to the still of the crystallization apparatus that can overturn
Body 1, is slowly introducing 5 DEG C of cold water in chuck so that material was cooled to 5～10 DEG C in 3 hours, and crystallization terminates；In chuck slowly
It is passed through 25～32 DEG C of warm water, makes crystallized stock be incubated 2 hours, after insulation terminates, slowly overturn kettle 1 with rotating shaft 4 for rotary shaft
To 180 °, making material slowly be poured onto on screen plate 3, open and rotate bar 5, its rotation is also moved to screen plate 3, the cross bar of front end
The material being deposited in screen plate 3 surface is bulldozed by 7, opens vacuum, carries out sucking filtration, and the material that sucking filtration goes out enters impurity collecting tank,
After sucking filtration terminates for 2 hours；Kettle 1 chuck is passed through 45～50 DEG C of warm water, by all material melts in kettle, collects liquid phase and enters
Product collecting tank, obtains highly purified 2-chloro-5-chloromethyl thiazole, content 99.7%.
Claims (8)
1. a separation and refining method for 2-chloro-5-chloromethyl thiazole, is with 2-chloro-5-chloromethyl thiazole crude product as raw material, logical
Crossing crystallization process and prepare 2-chloro-5-chloromethyl thiazole, step is as follows:
(1) washing: in washing kettle, by 2-chloro-5-chloromethyl thiazole dissolving crude product in solvent, adds water in batches and carries out water
Wash, pH value=6～7 of washing organic facies；
(2) absorption is except color: add decolorizing adsorbent in the organic facies that step (1) obtains, and keeps stirring under uniform temperature certain
Time, become light yellow to mother solution color from buff；
(3) filter pressing: transfer the material into filter-pressing cauldron, carries out filter pressing, and the faint yellow organic facies being press-filtered out enters collecting tank, filter-pressing cauldron
In filter cake be transferred to other equipment, and optionally carry out regenerating with recycling；
(4) precipitation: the material in step (3) collecting tank is transferred to precipitation still, is keeping certain pressure and uniform temperature
In the case of carry out reduce pressure precipitation；
(5) organic solvent is added: in precipitation still, add organic solvent, stir, keep temperature of charge about 40 DEG C；
(6) crystallization apparatus crystallization, intensification fusing: the material in precipitation still is transferred to the crystallization apparatus that can overturn, through supercool
But crystallize, be warming up to the temperature more slightly higher than fusing point again and be incubated diaphoresis, overturn crystallization apparatus, make material be poured onto screen plate, enter
Row filters；It is warmed up to more than fusing point again, all solids in melting plant, collect and obtain 2-chloro-5-chloromethyl thiazole；
Described crystallization apparatus includes kettle (1), mother liquor mouth (2), be arranged in kettle (1) and can by kettle (1) vertically
It is divided into two-part screen plate (3), is arranged at the rotating shaft (4) of the outside horizontal direction of kettle (1), prolongs from kettle (1) is outside
Extend the internal rotation bar (5) of interior kettle (1), discharging opening (6), it is characterised in that: mother liquor mouth (2) and rotation bar (5) position
In screen plate (3) side, discharging opening (6) is positioned at screen plate (3) opposite side；Rotate bar (5) vertical with screen plate (3) and can be relative
Mobile in screen plate (3), and rotate bar (5) front end equipped with being parallel to the cross bar (7) of screen plate, rotating shaft (4) connects rotation
Device, can by whole kettle (1) with rotating shaft (4) be rotary shaft rotate 180 °.
The separation and refining method of 2-chloro-5-chloromethyl thiazole the most according to claim 1, it is characterised in that: step (1)
In, solvent is one or more mixed liquors in dichloromethane, dichloroethanes, chloroform, toluene, ethyl acetate.
The separation and refining method of 2-chloro-5-chloromethyl thiazole the most according to claim 1 and 2, it is characterised in that: step
(2) compositions of one or more during decolorizing adsorbent is molecular sieve, silica gel, activated carbon, macroporous adsorbent resin；Decolorization adsorption
Temperature is 10～90 DEG C；Mixing time is 1～6 hour.
4. according to the separation and refining method of the 2-chloro-5-chloromethyl thiazole described in any one of claim 1-2, it is characterised in that:
In step (4), precipitation pressure is-0.05～-0.095bar；Precipitation temperature is 40～100 DEG C；Distilling off solvent is the most direct
Apply mechanically dissolving 2-chloro-5-chloromethyl thiazole crude product in step (1).
5. according to the separation and refining method of the 2-chloro-5-chloromethyl thiazole described in any one of claim 1-2, it is characterised in that:
Step (5) organic solvent is acetone, dichloromethane, 1,2-dichloroethanes, chloroform, methanol, ethanol, ethyl acetate, N, N-diformazan
One or more solvents in base Methanamide, dimethyl sulfoxide, N-Methyl pyrrolidone.
The separation and refining method of 2-chloro-5-chloromethyl thiazole the most according to claim 1, it is characterised in that: described knot
Brilliant device transfer lever (5) is positioned at the medium position of the horizontal direction of kettle (1), the maximum of rotatable bar (5) stretch into distance away from
Screen plate (3) 2～5 centimetres；Cross bar (7) is flat-shaped, length 10～30 centimetres.
The separation and refining method of 2-chloro-5-chloromethyl thiazole the most according to claim 1, it is characterised in that: kettle (1) end
Other parts of portion are smooth crystalline portion, and kettle (1) top is installed and is provided with discharging opening directly over screen plate (3), screen plate (3)
(6), screen plate (3) mesh number is: 50～800 mesh.
The separation and refining method of 2-chloro-5-chloromethyl thiazole the most according to claim 1, it is characterised in that: kettle (1) carries
There is chuck, the hot and cold medium can being passed through between-30～180 DEG C；The setup of entrances and exits of hot and cold medium closes on rotating shaft (4)
Position.
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| 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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| 2-氯-5-氯甲基-1,3-噻唑提纯新方法;张海滨等;《精细化工中间体》;20061031;第36卷(第5期);第50-51页 * |
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