CN104803990A - Production process of difenoconazole - Google Patents
Production process of difenoconazole Download PDFInfo
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- CN104803990A CN104803990A CN201510135403.1A CN201510135403A CN104803990A CN 104803990 A CN104803990 A CN 104803990A CN 201510135403 A CN201510135403 A CN 201510135403A CN 104803990 A CN104803990 A CN 104803990A
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- C07—ORGANIC CHEMISTRY
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Abstract
The invention discloses a production process of difenoconazole. The production process comprises steps as follows: etherification: parachlorophenol and solid potassium hydroxide which are well weighed and metered m-dichlorobenzene are put into an etherification reaction kettle, and etherate is obtained and transferred to a next procedure; acylation: etherate obtained in the etherification step, a small amount of aluminum trichloride and metered methylene dichloride are added to an acylation kettle to be stirred and mixed at the room temperature, acetyl chloride is dropwise added for a reaction, and acylate is obtained and transferred to a next procedure; cyclization: acylate obtained in the acylation step as well as propylene glycol and cyclohexane which are metered is put into a cyclization kettle at the room temperature, and materials are transferred to a next procedure after the materials are cooled to the room temperature by cooling water; bromination: a cyclization material is introduced into a bromination kettle at the room temperature, is bromized by dropwise adding bromine and is added with water for washing, waste water obtained through washing is sent for waste water treatment, and bromide is obtained and transferred to a next procedure; condensation: the bromide obtained in the bromination step, triazole, caustic soda flakes and dimethyl sulfoxide are put into a condensation reaction kettle. According to the production process of the difenoconazole, the reaction time of the process is shortened, the yield is increased, three wastes are fewer, and clean and environment-friendly production is realized.
Description
Technical field
The present invention relates to a kind of production technique of difenoconazole.
Background technology
For the production process route of difenoconazole, the patent No. be 200410065404.5 patent application document disclose a kind of synthesis route and be: 4-(4-chlorophenoxy)-2-chloro-acetophenone and 1, 2-propylene glycol ring-closure reaction generation cyclocomplex-suitable, the chloro-4-(2 of trans-3-, 4-dimethyl-1, 3-bis-Evil pentane-2-base) phenyl-4-chloro-phenyl-ether, under reaction has catalyzer tosic acid existent condition in a solvent, above-mentioned cyclocomplex and bromine reaction, generation bromide-suitable, the chloro-4-of trans-3-(4-methyl-2-brooethyl-1, 3-bis-Evil pentane-2-base) phenyl-4-chloro-phenyl-ether, above-mentioned bromide and 1,2,4-1-Sodium-1,2,4-Triazole, under potassiumiodide catalysis, react in polar solvent, and its concentration mass ratio is 15%-50%, obtained target compound.
The weak point of above-mentioned patented method is: 1, in the preparation process of starting raw material 4-(4-chlorophenoxy)-2-chloro-acetophenone, be difficult to reach desirable quality and yield, cause purification & isolation difficulty, thus greatly have impact on the content of difenoconazole crude product.This compound has very large hormesis to eyes, skin simultaneously, comparatively large to the hazard ratio of operator, be equipped with advanced shield.2, need in salify and neutralization reaction process with a large amount of organic solvents, lossy in recovery organic solvent process, easily cause topsoil.In addition in water washing process, a large amount of waste water of generation, more difficult qualified discharge.
Therefore, need to provide a kind of new technical scheme to solve the problems referred to above.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of production technique of difenoconazole.
For solving the problems of the technologies described above, the production technique of difenoconazole of the present invention, is characterized in that, comprises the following steps:
A, etherificate: the Meta Dichlorobenzene of the para-chlorophenol weighed up, solid potassium hydroxide and metering is dropped in etherifying reactor, jacket steam is warming up to 100-105 DEG C, normal pressure dehydration reaction 10-12h, after sampling analysis is qualified, water coolant filters after dropping to room temperature, filter residue containing Repone K delivers to fixed-end forces, filtrate is back to chuck in reactor and is heated to 140-142 DEG C, be decompressed to-0.090 to-0.092MPa after first normal pressure and deviate from excessive Meta Dichlorobenzene recovery, the etherate obtained proceeds to subsequent processing;
B, acidylate: the etherate at room temperature upper step obtained and a small amount of aluminum chloride add in acylation kettle and be uniformly mixed together with the methylene dichloride measured, drip Acetyl Chloride 98Min. to react, be 23-25 DEG C by chuck cooling water control temperature, after dropwising, the water adding 0 DEG C in still is hydrolyzed, control temperature is no more than 50 DEG C, the hydrogen chloride gas produced when acylation process and hydrolysis is connected to outdoor absorption by evacuated tube and makes hydrochloric acid, stratification after hydrolysis, water layer send wastewater treatment, organic layer is heated to 38-40 DEG C by chuck in still, air distillation is deviate from methylene dichloride and is applied mechanically, the acylate obtained proceeds to subsequent processing,
C, cyclization: in cyclization still, at room temperature drop into upper step acylate and the propylene glycol measured, hexanaphthene, chuck is heated to 80 DEG C of back flow reaction 10-12h, after sampling analysis is qualified, after cooling water temperature to room temperature, material is proceeded to next step operation;
D, bromination: at room temperature, cyclization material is driven in bromination still, opening clamp jacket water is lowered the temperature, drip bromine and carry out bromination, control temperature of reaction below 20 DEG C, the hydrogen bromide that bromination process produces is through absorbing by liquid caustic soda process, get after dropwising and analyse analysis, add water washing, washes send wastewater treatment, and the organic layer pump after cleaning is driven in still kettle, and jacket steam is warming up to 80 DEG C, be decompressed to-0.090 to-0.092MPa distillation after first normal pressure to deviate from hexanaphthene and apply mechanically, the bromide obtained proceeds to subsequent processing;
E, condensation: at room temperature, by the bromide that upper step obtains, triazole, sheet alkali drops in condensation reaction still together with dimethyl sulfoxide (DMSO), jacket steam temperature rising reflux 100 DEG C, after dehydration reaction 7-8h, after sampling analysis is qualified, continue to be warming up to 135-140 DEG C, be decompressed to-0.083 to-0.085MPa distillation deviate from dimethyl sulfoxide (DMSO) apply mechanically, room temperature is down in material chuck cooling after precipitation, add a certain amount of toluene and water stirring, stratification, water layer send wastewater treatment, organic layer is normal pressure in still, deviate from most of toluene for 110 DEG C, after precipitation, material chuck is refrigerated to room temperature crystallization, rake type drier sent into by material after filtering, 55-60 DEG C is carried out drying treatment, finally automatically pack to obtain finished product, filtrate send normal pressure in toluene distillation still, at 110 DEG C, Distillation recovery toluene is applied mechanically.
Reaction principle is as follows:
1, etherificate
2, acidylate
Hydrolysis
3, cyclization
4, bromination
Vent gas treatment
5, condensation
Beneficial effect of the present invention: by improving its operational path, shorten the technological reaction time, improve yield, the three wastes are few, realizes clean environment firendly and produces.
Embodiment
In order to deepen the understanding of the present invention, below the invention will be further described, this embodiment, only for explaining the present invention, does not form the restriction to protection scope of the present invention.
Embodiment 1
The production technique of difenoconazole, comprises the following steps:
A, etherificate: the Meta Dichlorobenzene of the para-chlorophenol weighed up, solid potassium hydroxide and metering is dropped in etherifying reactor, jacket steam is warming up to 100 DEG C, normal pressure dehydration reaction 10h, after sampling analysis is qualified, water coolant filters after dropping to room temperature, and the filter residue containing Repone K delivers to fixed-end forces, and filtrate is back to chuck in reactor and is heated to 140 DEG C, be decompressed to-0.090 MPa after first normal pressure and deviate from excessive Meta Dichlorobenzene recovery, the etherate obtained proceeds to subsequent processing;
B, acidylate: the etherate at room temperature upper step obtained and a small amount of aluminum chloride add in acylation kettle and be uniformly mixed together with the methylene dichloride measured, drip Acetyl Chloride 98Min. to react, it is 23 DEG C by chuck cooling water control temperature, after dropwising, the water adding 0 DEG C in still is hydrolyzed, control temperature is no more than 50 DEG C, the hydrogen chloride gas produced when acylation process and hydrolysis is connected to outdoor absorption by evacuated tube and makes hydrochloric acid, stratification after hydrolysis, water layer send wastewater treatment, organic layer is heated to 38 DEG C by chuck in still, air distillation is deviate from methylene dichloride and is applied mechanically, the acylate obtained proceeds to subsequent processing,
C, cyclization: in cyclization still, at room temperature drop into upper step acylate and the propylene glycol measured, hexanaphthene, chuck is heated to 80 DEG C of back flow reaction 10h, after sampling analysis is qualified, after cooling water temperature to room temperature, material is proceeded to next step operation;
D, bromination: at room temperature, cyclization material is driven in bromination still, opening clamp jacket water is lowered the temperature, drip bromine and carry out bromination, control temperature of reaction below 20 DEG C, the hydrogen bromide that bromination process produces is through absorbing by liquid caustic soda process, get after dropwising and analyse analysis, add water washing, washes send wastewater treatment, and the organic layer pump after cleaning is driven in still kettle, and jacket steam is warming up to 80 DEG C, be decompressed to-0.091 MPa distillation after first normal pressure to deviate from hexanaphthene and apply mechanically, the bromide obtained proceeds to subsequent processing;
E, condensation: at room temperature, by the bromide that upper step obtains, triazole, sheet alkali drops in condensation reaction still together with dimethyl sulfoxide (DMSO), jacket steam temperature rising reflux 100 DEG C, after dehydration reaction 7-8h, after sampling analysis is qualified, continue to be warming up to 135 DEG C, be decompressed to-0.083 MPa distillation deviate from dimethyl sulfoxide (DMSO) apply mechanically, room temperature is down in material chuck cooling after precipitation, add a certain amount of toluene and water stirring, stratification, water layer send wastewater treatment, organic layer is normal pressure in still, deviate from most of toluene for 110 DEG C, after precipitation, material chuck is refrigerated to room temperature crystallization, rake type drier sent into by material after filtering, 55 DEG C are carried out drying treatment, finally automatically pack to obtain finished product, filtrate send normal pressure in toluene distillation still, at 110 DEG C, Distillation recovery toluene is applied mechanically.
Embodiment 2
The production technique of difenoconazole, comprises the following steps:
A, etherificate: the Meta Dichlorobenzene of the para-chlorophenol weighed up, solid potassium hydroxide and metering is dropped in etherifying reactor, jacket steam is warming up to 102 DEG C, normal pressure dehydration reaction 11h, after sampling analysis is qualified, water coolant filters after dropping to room temperature, and the filter residue containing Repone K delivers to fixed-end forces, and filtrate is back to chuck in reactor and is heated to 140 DEG C, be decompressed to-0.091 MPa after first normal pressure and deviate from excessive Meta Dichlorobenzene recovery, the etherate obtained proceeds to subsequent processing;
B, acidylate: the etherate at room temperature upper step obtained and a small amount of aluminum chloride add in acylation kettle and be uniformly mixed together with the methylene dichloride measured, drip Acetyl Chloride 98Min. to react, it is 24 DEG C by chuck cooling water control temperature, after dropwising, the water adding 0 DEG C in still is hydrolyzed, control temperature is no more than 50 DEG C, the hydrogen chloride gas produced when acylation process and hydrolysis is connected to outdoor absorption by evacuated tube and makes hydrochloric acid, stratification after hydrolysis, water layer send wastewater treatment, organic layer is heated to 39 DEG C by chuck in still, air distillation is deviate from methylene dichloride and is applied mechanically, the acylate obtained proceeds to subsequent processing,
C, cyclization: in cyclization still, at room temperature drop into upper step acylate and the propylene glycol measured, hexanaphthene, chuck is heated to 80 DEG C of back flow reaction 11h, after sampling analysis is qualified, after cooling water temperature to room temperature, material is proceeded to next step operation;
D, bromination: at room temperature, cyclization material is driven in bromination still, opening clamp jacket water is lowered the temperature, drip bromine and carry out bromination, control temperature of reaction below 20 DEG C, the hydrogen bromide that bromination process produces is through absorbing by liquid caustic soda process, get after dropwising and analyse analysis, add water washing, washes send wastewater treatment, and the organic layer pump after cleaning is driven in still kettle, and jacket steam is warming up to 80 DEG C, be decompressed to-0.091MPa distillation after first normal pressure to deviate from hexanaphthene and apply mechanically, the bromide obtained proceeds to subsequent processing;
E, condensation: at room temperature, by the bromide that upper step obtains, triazole, sheet alkali drops in condensation reaction still together with dimethyl sulfoxide (DMSO), jacket steam temperature rising reflux 100 DEG C, after dehydration reaction 7-8h, after sampling analysis is qualified, continue to be warming up to 138 DEG C, be decompressed to-0.084 MPa distillation deviate from dimethyl sulfoxide (DMSO) apply mechanically, room temperature is down in material chuck cooling after precipitation, add a certain amount of toluene and water stirring, stratification, water layer send wastewater treatment, organic layer is normal pressure in still, deviate from most of toluene for 110 DEG C, after precipitation, material chuck is refrigerated to room temperature crystallization, rake type drier sent into by material after filtering, 58 DEG C are carried out drying treatment, finally automatically pack to obtain finished product, filtrate send normal pressure in toluene distillation still, at 110 DEG C, Distillation recovery toluene is applied mechanically.
Embodiment 3
The production technique of difenoconazole, comprises the following steps:
A, etherificate: the Meta Dichlorobenzene of the para-chlorophenol weighed up, solid potassium hydroxide and metering is dropped in etherifying reactor, jacket steam is warming up to 105 DEG C, normal pressure dehydration reaction 12h, after sampling analysis is qualified, water coolant filters after dropping to room temperature, and the filter residue containing Repone K delivers to fixed-end forces, and filtrate is back to chuck in reactor and is heated to 142 DEG C, be decompressed to-0.092MPa after first normal pressure and deviate from excessive Meta Dichlorobenzene recovery, the etherate obtained proceeds to subsequent processing;
B, acidylate: the etherate at room temperature upper step obtained and a small amount of aluminum chloride add in acylation kettle and be uniformly mixed together with the methylene dichloride measured, drip Acetyl Chloride 98Min. to react, it is 25 DEG C by chuck cooling water control temperature, after dropwising, the water adding 0 DEG C in still is hydrolyzed, control temperature is no more than 50 DEG C, the hydrogen chloride gas produced when acylation process and hydrolysis is connected to outdoor absorption by evacuated tube and makes hydrochloric acid, stratification after hydrolysis, water layer send wastewater treatment, organic layer is heated to 40 DEG C by chuck in still, air distillation is deviate from methylene dichloride and is applied mechanically, the acylate obtained proceeds to subsequent processing,
C, cyclization: in cyclization still, at room temperature drop into upper step acylate and the propylene glycol measured, hexanaphthene, chuck is heated to 80 DEG C of back flow reaction 12h, after sampling analysis is qualified, after cooling water temperature to room temperature, material is proceeded to next step operation;
D, bromination: at room temperature, cyclization material is driven in bromination still, opening clamp jacket water is lowered the temperature, drip bromine and carry out bromination, control temperature of reaction below 20 DEG C, the hydrogen bromide that bromination process produces is through absorbing by liquid caustic soda process, get after dropwising and analyse analysis, add water washing, washes send wastewater treatment, and the organic layer pump after cleaning is driven in still kettle, and jacket steam is warming up to 80 DEG C, be decompressed to 0.092MPa distillation after first normal pressure to deviate from hexanaphthene and apply mechanically, the bromide obtained proceeds to subsequent processing;
E, condensation: at room temperature, by the bromide that upper step obtains, triazole, sheet alkali drops in condensation reaction still together with dimethyl sulfoxide (DMSO), jacket steam temperature rising reflux 100 DEG C, after dehydration reaction 8h, after sampling analysis is qualified, continue to be warming up to 140 DEG C, be decompressed to-0.085MPa distillation deviate from dimethyl sulfoxide (DMSO) apply mechanically, room temperature is down in material chuck cooling after precipitation, add a certain amount of toluene and water stirring, stratification, water layer send wastewater treatment, organic layer is normal pressure in still, deviate from most of toluene for 110 DEG C, after precipitation, material chuck is refrigerated to room temperature crystallization, rake type drier sent into by material after filtering, 60 DEG C are carried out drying treatment, finally automatically pack to obtain finished product, filtrate send normal pressure in toluene distillation still, at 110 DEG C, Distillation recovery toluene is applied mechanically.
The present invention is by etherificate, acidylate, cyclization, bromination, condensation reaction, and shorten the technological reaction time, improve yield, the three wastes are few, realizes clean environment firendly and produces.
Claims (1)
1. the production technique of difenoconazole, is characterized in that, comprises the following steps:
A, etherificate: the Meta Dichlorobenzene of the para-chlorophenol weighed up, solid potassium hydroxide and metering is dropped in etherifying reactor, jacket steam is warming up to 100-105 DEG C, normal pressure dehydration reaction 10-12h, after sampling analysis is qualified, water coolant filters after dropping to room temperature, filter residue containing Repone K delivers to fixed-end forces, filtrate is back to chuck in reactor and is heated to 140-142 DEG C, be decompressed to-0.090 to-0.092MPa after first normal pressure and deviate from excessive Meta Dichlorobenzene recovery, the etherate obtained proceeds to subsequent processing;
B, acidylate: the etherate at room temperature upper step obtained and a small amount of aluminum chloride add in acylation kettle and be uniformly mixed together with the methylene dichloride measured, drip Acetyl Chloride 98Min. to react, be 23-25 DEG C by chuck cooling water control temperature, after dropwising, the water adding 0 DEG C in still is hydrolyzed, control temperature is no more than 50 DEG C, the hydrogen chloride gas produced when acylation process and hydrolysis is connected to outdoor absorption by evacuated tube and makes hydrochloric acid, stratification after hydrolysis, water layer send wastewater treatment, organic layer is heated to 38-40 DEG C by chuck in still, air distillation is deviate from methylene dichloride and is applied mechanically, the acylate obtained proceeds to subsequent processing,
C, cyclization: in cyclization still, at room temperature drop into upper step acylate and the propylene glycol measured, hexanaphthene, chuck is heated to 80 DEG C of back flow reaction 10-12h, after sampling analysis is qualified, after cooling water temperature to room temperature, material is proceeded to next step operation;
D, bromination: at room temperature, cyclization material is driven in bromination still, opening clamp jacket water is lowered the temperature, drip bromine and carry out bromination, control temperature of reaction below 20 DEG C, the hydrogen bromide that bromination process produces is through absorbing by liquid caustic soda process, get after dropwising and analyse analysis, add water washing, washes send wastewater treatment, and the organic layer pump after cleaning is driven in still kettle, and jacket steam is warming up to 80 DEG C, be decompressed to-0.090 to-0.092MPa distillation after first normal pressure to deviate from hexanaphthene and apply mechanically, the bromide obtained proceeds to subsequent processing;
E, condensation: at room temperature, by the bromide that upper step obtains, triazole, sheet alkali drops in condensation reaction still together with dimethyl sulfoxide (DMSO), jacket steam temperature rising reflux 100 DEG C, after dehydration reaction 7-8h, after sampling analysis is qualified, continue to be warming up to 135-140 DEG C, be decompressed to-0.083 to-0.085MPa distillation deviate from dimethyl sulfoxide (DMSO) apply mechanically, room temperature is down in material chuck cooling after precipitation, add a certain amount of toluene and water stirring, stratification, water layer send wastewater treatment, organic layer is normal pressure in still, deviate from most of toluene for 110 DEG C, after precipitation, material chuck is refrigerated to room temperature crystallization, rake type drier sent into by material after filtering, 55-60 DEG C is carried out drying treatment, finally automatically pack to obtain finished product, filtrate send normal pressure in toluene distillation still, at 110 DEG C, Distillation recovery toluene is applied mechanically.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107382979A (en) * | 2017-06-13 | 2017-11-24 | 周保东 | A kind of Difenoconazole molecular distillation process for purification |
| CN109593083A (en) * | 2018-12-28 | 2019-04-09 | 利民化工股份有限公司 | A kind of preparation method of difenoconazole nitrate |
| CN109970722A (en) * | 2019-05-06 | 2019-07-05 | 长沙鑫本药业有限公司 | A kind of synthesis technology of difenoconazole |
| CN110204534A (en) * | 2019-05-30 | 2019-09-06 | 浙江禾本科技有限公司 | A kind of refining methd of difenoconazole |
| CN111574493A (en) * | 2020-06-12 | 2020-08-25 | 青岛凯源祥化工有限公司 | Preparation method of bromide of substituted diphenyl ether |
| CN112300137A (en) * | 2020-08-24 | 2021-02-02 | 江苏禾本生化有限公司 | Synthetic method of high-purity difenoconazole |
| CN113861004A (en) * | 2021-11-03 | 2021-12-31 | 山东潍坊双星农药有限公司 | Catalytic synthesis method of difenoconazole intermediate difenone |
-
2015
- 2015-03-26 CN CN201510135403.1A patent/CN104803990A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107382979A (en) * | 2017-06-13 | 2017-11-24 | 周保东 | A kind of Difenoconazole molecular distillation process for purification |
| CN109593083A (en) * | 2018-12-28 | 2019-04-09 | 利民化工股份有限公司 | A kind of preparation method of difenoconazole nitrate |
| CN109593083B (en) * | 2018-12-28 | 2022-03-01 | 利民化学有限责任公司 | Preparation method of difenoconazole nitrate |
| CN109970722A (en) * | 2019-05-06 | 2019-07-05 | 长沙鑫本药业有限公司 | A kind of synthesis technology of difenoconazole |
| CN110204534A (en) * | 2019-05-30 | 2019-09-06 | 浙江禾本科技有限公司 | A kind of refining methd of difenoconazole |
| CN111574493A (en) * | 2020-06-12 | 2020-08-25 | 青岛凯源祥化工有限公司 | Preparation method of bromide of substituted diphenyl ether |
| CN112300137A (en) * | 2020-08-24 | 2021-02-02 | 江苏禾本生化有限公司 | Synthetic method of high-purity difenoconazole |
| CN112300137B (en) * | 2020-08-24 | 2022-03-25 | 江苏禾本生化有限公司 | Synthetic method of high-purity difenoconazole |
| CN113861004A (en) * | 2021-11-03 | 2021-12-31 | 山东潍坊双星农药有限公司 | Catalytic synthesis method of difenoconazole intermediate difenone |
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Application publication date: 20150729 |