CN105837508B - A kind of crystallization and purification technique of pyraclostrobin condensation intermediate - Google Patents
A kind of crystallization and purification technique of pyraclostrobin condensation intermediate Download PDFInfo
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- CN105837508B CN105837508B CN201610295320.3A CN201610295320A CN105837508B CN 105837508 B CN105837508 B CN 105837508B CN 201610295320 A CN201610295320 A CN 201610295320A CN 105837508 B CN105837508 B CN 105837508B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
Abstract
The invention discloses a kind of crystallization and purification techniques of pyraclostrobin condensation intermediate：By weight, 80 100 parts of pyraclostrobin condensation intermediate is added in into crystallization kettle, 400 1000 parts of absolute methanol and 20 25 parts of N, N dimethylformamides, it is warming up to 60 80 DEG C, flow back 30 60min, cooling down is to 35 45 DEG C, 35 parts of triethylamines are added dropwise, temperature is maintained at 35 45 DEG C, continue to stir 15 30min, make greenhouse cooling to 38 DEG C, insulated and stirred 12 hours, it filters, mother liquor is collected to mother liquor tank, filter cake is eluted twice with 38 DEG C of a small amount of absolute methanol, take out filter cake, it is placed in drying in oven, intermediate crystallizations object is condensed up to the pyraclostrobin of high-purity.The crystallization effect of the present invention is good, and not only crystallized product purity is high, but also crystallization yield is high；Device therefor is simple, suitable for industrialized production, can generate significant economic benefit.
Description
Technical field
The invention belongs to pesticide production technology fields, are related to a kind of crystallization and purification work of pyraclostrobin condensation intermediate
Skill.
Background technology
Pyraclostrobin also known as pyraclostrobin, English common name：Pyraclostrobin, chemical name：N-[2-[[1-
(4- chlorphenyls) pyrazole-3-yl] oxygen methyl] phenyl]-N- methoxy carbamate methyl esters.Pyraclostrobin belongs to methoxy propyl
Alkene bactericide of phosphate (phosphinium) ester mainly acts on the mitochondria of fungi, prevents electron transmission so as to which fungi be inhibited to grow.Pyraclostrobin
All types of fungal pathogens can be prevented, wide sterilization spectrum is mainly used for preventing uncinula necator, downy mildew；Wheat powdery mildew,
Rust；Leaf rust of barley；The black leaf cecospora spot of banana；The diseases such as tomato morning, late blight.Pyraclostrobin includes wheat to various crop
Class, grape, fruit tree, the multiple diseases of vegetables are effective.
The synthesis of pyraclostrobin is mainly with parachloroanilinum, sodium sulfite, methyl acrylate, ortho-methylnitrobenzene, chloro-carbonic acid
Methyl esters, dimethyl suflfate etc. be raw material, successively by diazotising, reduction, acidification neutralization, Cyclization, oxidation, bromination, condensation,
It restores, be esterified, methylate, finally obtained product pyraclostrobin.
Condensation process therein is the oxidation product obtained using oxidation operation --- pyrazoles alcohol and bromination process obtain
Brominated product --- o-nitrobenzyl bromide is raw material, and condensation reaction occurs under the conditions of Sodium Hydroxide Alkaline heating, obtains
Product is pyraclostrobin condensation intermediate.The entitled pyrazoles nitrobenzene of intermediate is condensed, molecular formula is：C16H12O3N3CL,
Chemical name：2- [(N-4 chlorphenyls) -1H- pyrazole-3-yl oxygen methyl]-nitrobenzene.The pure of condensation intermediate is found in actual production
Degree is larger to the impurities affect of subsequent reactions product and final products, usually, is condensed the purity of intermediate in a certain range
Between, purity often declines 1%, the purity of subsequent reduzate will be caused to decline about 1.5%, the purity of esterification products declines
About 2%, the purity of final products pyraclostrobin declines about 3.5%, and it is very unfavorable that the purifying of final products is refined in this way.
Invention content
The purpose of the present invention is to provide a kind of effective crystallization and purification technique, to improve pyraclostrobin condensation intermediate
Purity.
In order to achieve the above objectives, the present invention uses following technical solutions.
A kind of crystallization and purification technique of pyraclostrobin condensation intermediate：
By weight, 80-100 parts of pyraclostrobin condensation intermediates are added in into crystallization kettle, then are pumped into 400-1000
The absolute methanol and 20-25 parts of n,N-Dimethylformamide of part, open stirring, are warming up to 60-80 DEG C, and flow back 30-60min,
Cooling down is to 35-45 DEG C, then 3-5 parts of triethylamines are slowly added dropwise into crystallization kettle, and after being added dropwise, temperature is maintained at 35-45
DEG C, continue to stir 15-30min, slow cooling, rate of temperature fall is controlled in 5-10 DEG C/h, and making greenhouse cooling, heat preservation is stirred to 3-8 DEG C
It mixes 1-2 hours, filters, mother liquor is collected to mother liquor tank, and filter cake is eluted twice with 3-8 DEG C of a small amount of absolute methanol, takes out filter cake, put
In drying in oven intermediate crystallizations object is condensed to get the pyraclostrobin of high-purity.
A kind of crystallization and purification technique of pyraclostrobin condensation intermediate, wherein the methanol in crystalline mother solution by walking as follows
Rapid recycling：Mother liquor tank stirring is opened, dilute hydrochloric acid is slowly added into mother liquor tank, mother liquor pH is adjusted to neutrality, is heated to 45-60
DEG C, it is concentrated under reduced pressure into no methanol and steams, stop concentration, the raw material of the methanol of recycling as next group Crystallization Procedure.
Advantages of the present invention：1st, crystallization and purification technique device therefor of the invention is simple, suitable for industrialized production；2nd, originally
The crystallization effect of invention is good, and the purity of crystal can be made to reach 95%-99%；3rd, using crystallization processes of the present invention, knot
For the yield of brilliant object between 91%-96%, crystallization yield is high.
Specific embodiment
With reference to specific embodiment, the present invention will be further described in detail, but protection domain of the presently claimed invention
It is not limited to the described range of specific embodiment.
Embodiment 1：
A kind of crystallization and purification technique of pyraclostrobin condensation intermediate：
By weight, 80 parts are added in into crystallization kettle, the pyraclostrobin that purity is 94.3% is condensed intermediate, then pump
The absolute methanol and 20 parts of n,N-Dimethylformamide, unlatching stirring for entering 400 parts are warming up to 60-80 DEG C, and flow back 30-
60min, cooling down is to 35-45 DEG C, then 3 parts of triethylamines are slowly added dropwise into crystallization kettle, and after being added dropwise, temperature is maintained at
35-45 DEG C, continue to stir 15-30min, slow cooling, rate of temperature fall is controlled in 5-10 DEG C/h, makes greenhouse cooling to 3-8 DEG C, is protected
Temperature stirring 1-2 hours, filters, and mother liquor is collected to mother liquor tank, and filter cake is eluted twice with 3-8 DEG C of a small amount of absolute methanol, takes out filter
Cake is placed in drying in oven and is condensed intermediate crystallizations object to get the pyraclostrobin of high-purity.
A kind of crystallization and purification technique of pyraclostrobin condensation intermediate, wherein the methanol in crystalline mother solution by walking as follows
Rapid recycling：Mother liquor tank stirring is opened, dilute hydrochloric acid is slowly added into mother liquor tank, mother liquor pH is adjusted to neutrality, is heated to 45-60
DEG C, it is concentrated under reduced pressure into no methanol and steams, stop concentration, the raw material of the methanol of recycling as next group Crystallization Procedure.
Embodiment 2：
A kind of crystallization and purification technique of pyraclostrobin condensation intermediate：
By weight, 80 parts are added in into crystallization kettle, the pyraclostrobin that purity is 93.6% is condensed intermediate, then pump
The absolute methanol and 20 parts of n,N-Dimethylformamide, unlatching stirring for entering 600 parts are warming up to 60-80 DEG C, and flow back 30-
60min, cooling down is to 35-45 DEG C, then 3 parts of triethylamines are slowly added dropwise into crystallization kettle, and after being added dropwise, temperature is maintained at
35-45 DEG C, continue to stir 15-30min, slow cooling, rate of temperature fall is controlled in 5-10 DEG C/h, makes greenhouse cooling to 3-8 DEG C, is protected
Temperature stirring 1-2 hours, filters, and mother liquor is collected to mother liquor tank, and filter cake is eluted twice with 3-8 DEG C of a small amount of absolute methanol, takes out filter
Cake is placed in drying in oven and is condensed intermediate crystallizations object to get the pyraclostrobin of high-purity.
Remaining is the same as embodiment 1.
Embodiment 3：
A kind of crystallization and purification technique of pyraclostrobin condensation intermediate：
By weight, 80 parts are added in into crystallization kettle, the pyraclostrobin that purity is 91.8% is condensed intermediate, then pump
The absolute methanol and 25 parts of n,N-Dimethylformamide, unlatching stirring for entering 800 parts are warming up to 60-80 DEG C, and flow back 30-
60min, cooling down is to 35-45 DEG C, then 5 parts of triethylamines are slowly added dropwise into crystallization kettle, and after being added dropwise, temperature is maintained at
35-45 DEG C, continue to stir 15-30min, slow cooling, rate of temperature fall is controlled in 5-10 DEG C/h, makes greenhouse cooling to 3-8 DEG C, is protected
Temperature stirring 1-2 hours, filters, and mother liquor is collected to mother liquor tank, and filter cake is eluted twice with 3-8 DEG C of a small amount of absolute methanol, takes out filter
Cake is placed in drying in oven and is condensed intermediate crystallizations object to get the pyraclostrobin of high-purity.
Remaining is the same as embodiment 1.
Embodiment 4：
A kind of crystallization and purification technique of pyraclostrobin condensation intermediate：
By weight, 80 parts are added in into crystallization kettle, the pyraclostrobin that purity is 90.4% is condensed intermediate, then pump
The absolute methanol and 20-25 parts of n,N-Dimethylformamide, unlatching stirring for entering 1000 parts are warming up to 60-80 DEG C, and flow back 30-
60min, cooling down is to 35-45 DEG C, then 5 parts of triethylamines are slowly added dropwise into crystallization kettle, and after being added dropwise, temperature is maintained at
35-45 DEG C, continue to stir 15-30min, slow cooling, rate of temperature fall is controlled in 5-10 DEG C/h, makes greenhouse cooling to 3-8 DEG C, is protected
Temperature stirring 1-2 hours, filters, and mother liquor is collected to mother liquor tank, and filter cake is eluted twice with 3-8 DEG C of a small amount of absolute methanol, takes out filter
Cake is placed in drying in oven and is condensed intermediate crystallizations object to get the pyraclostrobin of high-purity.
Remaining is the same as embodiment 1.
Embodiment 5：
A kind of crystallization and purification technique of pyraclostrobin condensation intermediate：
By weight, 90 parts are added in into crystallization kettle, the pyraclostrobin that purity is 90.4% is condensed intermediate, then pump
The absolute methanol and 20 parts of n,N-Dimethylformamide, unlatching stirring for entering 400 parts are warming up to 60-80 DEG C, and flow back 30-
60min, cooling down is to 35-45 DEG C, then 3 parts of triethylamines are slowly added dropwise into crystallization kettle, and after being added dropwise, temperature is maintained at
35-45 DEG C, continue to stir 15-30min, slow cooling, rate of temperature fall is controlled in 5-10 DEG C/h, makes greenhouse cooling to 3-8 DEG C, is protected
Temperature stirring 1-2 hours, filters, and mother liquor is collected to mother liquor tank, and filter cake is eluted twice with 3-8 DEG C of a small amount of absolute methanol, takes out filter
Cake is placed in drying in oven and is condensed intermediate crystallizations object to get the pyraclostrobin of high-purity.
Remaining is the same as embodiment 1.
Embodiment 6：
A kind of crystallization and purification technique of pyraclostrobin condensation intermediate：
By weight, 90 parts are added in into crystallization kettle, the pyraclostrobin that purity is 91.8% is condensed intermediate, then pump
The absolute methanol and 20 parts of n,N-Dimethylformamide, unlatching stirring for entering 600 parts are warming up to 60-80 DEG C, and flow back 30-
60min, cooling down is to 35-45 DEG C, then 3 parts of triethylamines are slowly added dropwise into crystallization kettle, and after being added dropwise, temperature is maintained at
35-45 DEG C, continue to stir 15-30min, slow cooling, rate of temperature fall is controlled in 5-10 DEG C/h, makes greenhouse cooling to 3-8 DEG C, is protected
Temperature stirring 1-2 hours, filters, and mother liquor is collected to mother liquor tank, and filter cake is eluted twice with 3-8 DEG C of a small amount of absolute methanol, takes out filter
Cake is placed in drying in oven and is condensed intermediate crystallizations object to get the pyraclostrobin of high-purity.
Remaining is the same as embodiment 1.
Embodiment 7：
A kind of crystallization and purification technique of pyraclostrobin condensation intermediate：
By weight, 90 parts are added in into crystallization kettle, the pyraclostrobin that purity is 93.6% is condensed intermediate, then pump
The absolute methanol and 25 parts of n,N-Dimethylformamide, unlatching stirring for entering 800 parts are warming up to 60-80 DEG C, and flow back 30-
60min, cooling down is to 35-45 DEG C, then 5 parts of triethylamines are slowly added dropwise into crystallization kettle, and after being added dropwise, temperature is maintained at
35-45 DEG C, continue to stir 15-30min, slow cooling, rate of temperature fall is controlled in 5-10 DEG C/h, makes greenhouse cooling to 3-8 DEG C, is protected
Temperature stirring 1-2 hours, filters, and mother liquor is collected to mother liquor tank, and filter cake is eluted twice with 3-8 DEG C of a small amount of absolute methanol, takes out filter
Cake is placed in drying in oven and is condensed intermediate crystallizations object to get the pyraclostrobin of high-purity.
Remaining is the same as embodiment 1.
Embodiment 8：
A kind of crystallization and purification technique of pyraclostrobin condensation intermediate：
By weight, 90 parts are added in into crystallization kettle, the pyraclostrobin that purity is 94.3% is condensed intermediate, then pump
The absolute methanol and 25 parts of n,N-Dimethylformamide, unlatching stirring for entering 1000 parts are warming up to 60-80 DEG C, and flow back 30-
60min, cooling down is to 35-45 DEG C, then 5 parts of triethylamines are slowly added dropwise into crystallization kettle, and after being added dropwise, temperature is maintained at
35-45 DEG C, continue to stir 15-30min, slow cooling, rate of temperature fall is controlled in 5-10 DEG C/h, makes greenhouse cooling to 3-8 DEG C, is protected
Temperature stirring 1-2 hours, filters, and mother liquor is collected to mother liquor tank, and filter cake is eluted twice with 3-8 DEG C of a small amount of absolute methanol, takes out filter
Cake is placed in drying in oven and is condensed intermediate crystallizations object to get the pyraclostrobin of high-purity.
Remaining is the same as embodiment 1.
Embodiment 9：
A kind of crystallization and purification technique of pyraclostrobin condensation intermediate：
By weight, 100 parts are added in into crystallization kettle, the pyraclostrobin that purity is 91.8% is condensed intermediate, then pump
The absolute methanol and 20 parts of n,N-Dimethylformamide, unlatching stirring for entering 400 parts are warming up to 60-80 DEG C, and flow back 30-
60min, cooling down is to 35-45 DEG C, then 3 parts of triethylamines are slowly added dropwise into crystallization kettle, and after being added dropwise, temperature is maintained at
35-45 DEG C, continue to stir 15-30min, slow cooling, rate of temperature fall is controlled in 5-10 DEG C/h, makes greenhouse cooling to 3-8 DEG C, is protected
Temperature stirring 1-2 hours, filters, and mother liquor is collected to mother liquor tank, and filter cake is eluted twice with 3-8 DEG C of a small amount of absolute methanol, takes out filter
Cake is placed in drying in oven and is condensed intermediate crystallizations object to get the pyraclostrobin of high-purity.
Remaining is the same as embodiment 1.
Embodiment 10：
A kind of crystallization and purification technique of pyraclostrobin condensation intermediate：
By weight, 100 parts are added in into crystallization kettle, the pyraclostrobin that purity is 93.6% is condensed intermediate, then pump
The absolute methanol and 20 parts of n,N-Dimethylformamide, unlatching stirring for entering 600 parts are warming up to 60-80 DEG C, and flow back 30-
60min, cooling down is to 35-45 DEG C, then 3 parts of triethylamines are slowly added dropwise into crystallization kettle, and after being added dropwise, temperature is maintained at
35-45 DEG C, continue to stir 15-30min, slow cooling, rate of temperature fall is controlled in 5-10 DEG C/h, makes greenhouse cooling to 3-8 DEG C, is protected
Temperature stirring 1-2 hours, filters, and mother liquor is collected to mother liquor tank, and filter cake is eluted twice with 3-8 DEG C of a small amount of absolute methanol, takes out filter
Cake is placed in drying in oven and is condensed intermediate crystallizations object to get the pyraclostrobin of high-purity.
Remaining is the same as embodiment 1.
Embodiment 11：
A kind of crystallization and purification technique of pyraclostrobin condensation intermediate：
By weight, 100 parts are added in into crystallization kettle, the pyraclostrobin that purity is 94.3% is condensed intermediate, then pump
The absolute methanol and 25 parts of n,N-Dimethylformamide, unlatching stirring for entering 800 parts are warming up to 60-80 DEG C, and flow back 30-
60min, cooling down is to 35-45 DEG C, then 5 parts of triethylamines are slowly added dropwise into crystallization kettle, and after being added dropwise, temperature is maintained at
35-45 DEG C, continue to stir 15-30min, slow cooling, rate of temperature fall is controlled in 5-10 DEG C/h, makes greenhouse cooling to 3-8 DEG C, is protected
Temperature stirring 1-2 hours, filters, and mother liquor is collected to mother liquor tank, and filter cake is eluted twice with 3-8 DEG C of a small amount of absolute methanol, takes out filter
Cake is placed in drying in oven and is condensed intermediate crystallizations object to get the pyraclostrobin of high-purity.
Remaining is the same as embodiment 1.
Embodiment 12：
A kind of crystallization and purification technique of pyraclostrobin condensation intermediate：
By weight, 100 parts are added in into crystallization kettle, the pyraclostrobin that purity is 90.4% is condensed intermediate, then pump
The absolute methanol and 25 parts of n,N-Dimethylformamide, unlatching stirring for entering 1000 parts are warming up to 60-80 DEG C, and flow back 30-
60min, cooling down is to 35-45 DEG C, then 5 parts of triethylamines are slowly added dropwise into crystallization kettle, and after being added dropwise, temperature is maintained at
35-45 DEG C, continue to stir 15-30min, slow cooling, rate of temperature fall is controlled in 5-10 DEG C/h, makes greenhouse cooling to 3-8 DEG C, is protected
Temperature stirring 1-2 hours, filters, and mother liquor is collected to mother liquor tank, and filter cake is eluted twice with 3-8 DEG C of a small amount of absolute methanol, takes out filter
Cake is placed in drying in oven and is condensed intermediate crystallizations object to get the pyraclostrobin of high-purity.
Remaining is the same as embodiment 1.
With the weight after crystallization before condensation intermediate crystallizations by weighing embodiment 1-12, crystallization yield is calculated, is passed through
HPLC detection condensation intermediate crystallizations before with the purity after crystallization, chromatographic condition：Chromatographic column 250-C18, mobile phase 80（Methanol）:
20（Water）, Detection wavelength 270nm, flow velocity 1ml/min the results are shown in Table 1.
It can obtain to draw a conclusion by table 1：1st, the purity of pyraclostrobin condensation intermediate is from average 92.5% before crystallization
Average 97.6% be increased to after crystallization, purification effect is notable；2nd, the yield of crystallization has been up to 96.0%, average yield
94.2%, crystallization yield is high；3rd, the purity before the crystallization of pyraclostrobin condensation intermediate is higher, and the purity after crystallization is higher.
Influence of the purity of pyraclostrobin condensation intermediate to subsequent reactions：
Respectively using the substance before and after the pyraclostrobin condensation intermediate crystallizations described in embodiment 1-4 as raw material, after progress
Continuous reduction reaction, esterification and methylation reaction obtains final products pyraclostrobin, and pyrazoles ether bacterium is detected by HPLC
The purity of ester, chromatographic condition：Chromatographic column 250-C18, mobile phase 80（Methanol）:20（Water）, Detection wavelength 270nm, flow velocity 1ml/
Min the results are shown in Table 2.
It can obtain to draw a conclusion by table 2：The average purity of condensation intermediate before crystallization is 92.5%, as raw material
Obtained pyraclostrobin average purity is 77.0%；The average purity of condensation intermediate after crystallization is 97.8%, as original
It is 95.5% to expect the obtained average purity of pyraclostrobin；The purity of condensation intermediate is increased to crystallization by 92.5% before crystallizing
Afterwards 97.8%, so that it may so that the purity of final products pyraclostrobin is increased to 95.5% by 77.0%, be equivalent to condensation intermediate
Purity often improve 1%, the purity of pyraclostrobin can improve about 3.5%, pass through to crystallize in this way and improve condensation intermediate
Purity, it is possible to greatly simplify subsequent purification procedures, generate good economic benefit.
Claims (1)
1. a kind of crystallization and purification technique of pyraclostrobin condensation intermediate, it is characterised in that：By weight, into crystallization kettle
Add in 90 parts, the pyraclostrobin that purity is 94.3% is condensed intermediate, then be pumped into 1000 parts of absolute methanol and 25 parts of N, N-
Dimethylformamide opens stirring, is warming up to 60-80 DEG C, and flow back 30-60min, and cooling down is to 35-45 DEG C, then to crystallization kettle
In 5 parts of triethylamines are slowly added dropwise, after being added dropwise, temperature is maintained at 35-45 DEG C, continue stir 15-30min, slow cooling, drop
Warm rate control is in 5-10 DEG C/h, and making greenhouse cooling, insulated and stirred 1-2 hours filters, and mother liquor is collected to mother liquor tank to 3-8 DEG C,
Filter cake is eluted twice with 3-8 DEG C of a small amount of absolute methanol, is taken out filter cake, is placed in pyrazoles ether of the drying in oven to get high-purity
Bacterium ester condensation intermediate crystallizations object；Methanol wherein in crystalline mother solution recycles as follows：Mother liquor tank stirring is opened, to mother
Dilute hydrochloric acid is slowly added in flow container, mother liquor pH is adjusted to neutrality, is heated to 45-60 DEG C, is concentrated under reduced pressure into no methanol and steams, stop
Concentration, the raw material of the methanol of recycling as next group Crystallization Procedure.
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| DE19732692C2 (en) * | 1997-07-30 | 2001-01-18 | Basf Ag | Process for the preparation of 2- (pyrazolyl-3'-oxymethylene) nitrobenzenes |
| CN104211641B (en) * | 2014-08-19 | 2016-08-24 | 山东康乔生物科技有限公司 | A kind of synthesis technique of pyraclostrobin |
| CN104496905A (en) * | 2014-12-29 | 2015-04-08 | 京博农化科技股份有限公司 | Preparation method of 2-[(N-4-chlorophenyl)-3-pyrazolyloxymethyl]nitrobenzene |
| CN105111148A (en) * | 2015-08-10 | 2015-12-02 | 安徽国星生物化学有限公司 | 2-[(N-para-chlorophenyl)-3-pyrazole oxymethyl]nitrobenzene and preparation method therefor and application thereof |
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