CN106699596A - Preparation process of methoxyfenozide - Google Patents
Preparation process of methoxyfenozide Download PDFInfo
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- CN106699596A CN106699596A CN201611255498.1A CN201611255498A CN106699596A CN 106699596 A CN106699596 A CN 106699596A CN 201611255498 A CN201611255498 A CN 201611255498A CN 106699596 A CN106699596 A CN 106699596A
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- temperature
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- toluene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/04—Preparation of hydrazides
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- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation process of methoxyfenozide. The process comprises steps as follows: (1) a condensation reaction: tert-butylhydrazine hydrochloride and dichloroethane are added to a condensation kettle at the room temperature, a jacket is cooled to subzero 6 DEG C to subzero 5 DEG C with brine freezing water, a caustic soda liquid is dropwise added, the mixture is left to stand for layering, a water layer is separated out for wastewater treatment, an organic layer is kept at the temperature, 3-methoxy-2-methoxybenzoyl chloride is dropwise added, and the dropwise adding speed is controlled, so that the temperature of the kettle does not exceed 0 DEG C; after a reaction is performed for 7-9 h, if sampling analysis proves qualification, water is added for stirring again, the mixture is left to stand for layering, the water layer is sent for wastewater treatment, dichloroethane is separated out from the organic layer at 75-85 DEG C under the normal pressure condition, toluene is added for dissolution after the mixture is cooled to the room temperature, and a toluene solution of a condensation compound is obtained.
Description
Technical field
The present invention relates to a kind of preparation technology of methoxyfenozide.
Background technology
Methoxyfenozide is a kind of novel specific benzoyl hydrazine low toxic pesticide, is mainly used in preventing and treating lepidoptera pest
Larva, such as beet armyworm, lopper worm, prodenia litura, dish agree worm, bollworm, apple leaf miner, fall webworms, pine moth, looper
And the snout moth's larva of rice etc., applicable crops such as brassicaceous vegetable, solanaceous vegetables, melon, cotton, apple, peach, paddy rice, forest etc.,
Its high efficiency and environment friendly meets requirement and the development trend of modern.But now with methoxyfenozide adopt mostly
The mode prepared with streamline, production cost is of a relatively high, and substantial amounts of waste water is produced in production process, and blowdown difficulty is big, enters
One step increased the production burden of enterprise.
The content of the invention
The technical problems to be solved by the invention are to provide a kind of preparation technology of methoxyfenozide.
In order to solve the above technical problems, the technical solution adopted by the present invention is：The preparation technology of methoxyfenozide, including with
Lower step：（1）Condensation reaction：At room temperature, by Tertiary butyl hydrazine hydrochloride and dichloroethanes addition condensation kettle, chuck is logical to be freezed
Salt solution is cooled to -6 ~ -5 DEG C, and liquid caustic soda is added dropwise, and stratification separates water layer and goes wastewater treatment, and organic layer is kept at a temperature of this, drop
Plus 3- methoxyl group -2- methyl benzoyl chlorides, rate of addition is controlled, kettle temperature is no more than 0 DEG C；After reaction 7 ~ 9h hours,
Sampling analysis is qualified, adds water stirring, and static layering, water layer send wastewater treatment, condition of normal pressure of the organic layer at 75 ~ 85 DEG C
Lower abjection dichloroethanes, is down to after room temperature plus toluene dissolving, obtains the toluene liquid of condensation product；（2）Acylation reaction：At room temperature,
The toluene liquid of the condensation product that upper step is obtained is transferred in acylation kettle, and opening freezing makes temperature in the kettle drop to less than 0 DEG C, while drop
Plus 3,5- dimethyl benzoyl chlorides and liquid caustic soda, and temperature in the kettle is kept less than 0 DEG C, the PH values in control kettle are in faintly acid；
After 7 ~ 9h of reaction, sampling analysis is qualified, stratification, and water layer send wastewater treatment, and organic layer is under 100 ~ 120 DEG C of normal pressure
Distillation abjection toluene, is down to after room temperature plus first alcohol and water is recrystallized, and then carries out press filtration, on the one hand, the thing that press filtration is obtained
Material feeding rake type drier, is dried treatment at a temperature of 60 ~ 70 DEG C, and finished product is finally packed to obtain automatically；On the other hand,
The filtrate that press filtration is obtained is gone in methyl alcohol steaming distillation still, and azeotropic steams methanol aqueous solution under 70 ~ 80 DEG C of condition of normal pressure, circulation
For re-crystallization step.
Compared with prior art, it is an advantage of the invention that：Preparation technology of the invention is used and reclaims again intermediate raw material
The mode for utilizing, reduces production cost and wastewater treatment difficulty, and finished product purity is high, and course of reaction is easy to control, meets
Requirement prepared by modernization agricultural chemicals.
Specific embodiment
The technical solution adopted by the present invention is：The preparation technology of methoxyfenozide, comprises the following steps：（1）Condensation reaction：
At room temperature, by Tertiary butyl hydrazine hydrochloride and dichloroethanes addition condensation kettle, the logical chilled brine of chuck is cooled to -6 ~ -5 DEG C,
Liquid caustic soda is added dropwise, stratification separates water layer and goes wastewater treatment, and organic layer is kept at a temperature of this, 3- methoxyl group -2- first is added dropwise
Base chlorobenzoyl chloride, controls rate of addition, kettle temperature is no more than 0 DEG C；After reaction 7 ~ 9h hours, sampling analysis is qualified, adds
Water is stirred, and static layering, water layer send wastewater treatment, and organic layer is deviate from dichloroethanes, is down under 75 ~ 85 DEG C of condition of normal pressure
Add toluene dissolving after room temperature, obtain the toluene liquid of condensation product；（2）Acylation reaction：At room temperature, the condensation product for upper step being obtained
Toluene liquid is transferred in acylation kettle, and opening freezing makes temperature in the kettle drop to less than 0 DEG C, while 3,5- dimethyl phenacyls are added dropwise
Chlorine and liquid caustic soda, and temperature in the kettle is kept less than 0 DEG C, the PH values in control kettle are in faintly acid；After 7 ~ 9h of reaction, sampling point
Qualified, stratification is analysed, water layer send wastewater treatment, and organic layer distills abjection toluene under 100 ~ 120 DEG C of normal pressure, is down to room
Wen Houjia first alcohol and waters are recrystallized, and then carry out press filtration, on the one hand, the material feeding rake type drier that press filtration is obtained,
Treatment is dried at a temperature of 60 ~ 70 DEG C, finished product is finally packed to obtain automatically；On the other hand, the filtrate that press filtration is obtained removes methyl alcohol
Steam in distillation still, azeotropic steams methanol aqueous solution under 70 ~ 80 DEG C of condition of normal pressure, circulates for re-crystallization step.
For a person skilled in the art, it can still be carried out to the technical scheme described in foregoing embodiments
Modification, or carries out equivalent to which part technical characteristic, it is all within the spirit and principles in the present invention, made it is any
Modification, equivalent, improvement etc., should be included within the scope of the present invention.
Claims (1)
1. the preparation technology of methoxyfenozide, it is characterised in that：The technique is comprised the following steps：（1）Condensation reaction：In room
Under temperature, by Tertiary butyl hydrazine hydrochloride and dichloroethanes addition condensation kettle, the logical chilled brine of chuck is cooled to -6 ~ -5 DEG C, drop
Liquid feeding alkali, stratification separates water layer and goes wastewater treatment, and organic layer is kept at a temperature of this, and 3- methoxyl group -2- methyl is added dropwise
Chlorobenzoyl chloride, controls rate of addition, kettle temperature is no more than 0 DEG C；After reaction 7 ~ 9h hours, sampling analysis is qualified, adds
Water is stirred, and static layering, water layer send wastewater treatment, and organic layer is deviate from dichloroethanes, is down under 75 ~ 85 DEG C of condition of normal pressure
Add toluene dissolving after room temperature, obtain the toluene liquid of condensation product；
（2）Acylation reaction：At room temperature, by step（1）The toluene liquid of the condensation product for obtaining is transferred in acylation kettle, opens freezing
Temperature in the kettle is dropped to less than 0 DEG C, while 3,5- dimethyl benzoyl chlorides and liquid caustic soda is added dropwise, and keep temperature in the kettle to be less than
0 DEG C, the PH values in control kettle are in faintly acid；After 7 ~ 9h of reaction, sampling analysis is qualified, and stratification, water layer is sent at waste water
Reason, organic layer distills abjection toluene under 100 ~ 120 DEG C of normal pressure, is down to after room temperature plus first alcohol and water is recrystallized, so
After carry out press filtration, on the one hand, material that press filtration is obtained feeding rake type drier, place is dried at a temperature of 60 ~ 70 DEG C
Reason, finally packs to obtain finished product automatically；On the other hand, the filtrate that press filtration is obtained is gone in methyl alcohol distillation still, normal at 70 ~ 80 DEG C
Azeotropic steams methanol aqueous solution under the conditions of pressure, circulates for re-crystallization step.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611255498.1A CN106699596A (en) | 2016-12-30 | 2016-12-30 | Preparation process of methoxyfenozide |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611255498.1A CN106699596A (en) | 2016-12-30 | 2016-12-30 | Preparation process of methoxyfenozide |
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| CN106699596A true CN106699596A (en) | 2017-05-24 |
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| CN201611255498.1A Pending CN106699596A (en) | 2016-12-30 | 2016-12-30 | Preparation process of methoxyfenozide |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110698395A (en) * | 2019-10-22 | 2020-01-17 | 杭州百诚医药科技股份有限公司 | Preparation method of topiroxostat intermediate |
| CN113248351A (en) * | 2021-05-26 | 2021-08-13 | 绍兴上虞新银邦生化有限公司 | Preparation method of 6-chloro-2-methoxytoluene and synthetic process of methoxyfenozide |
| GB2612942A (en) * | 2021-09-16 | 2023-05-24 | Rotam Agrochem Int Co Ltd | A crystalline form of methoxyfenozide, a process for its preparation and use of the same |
-
2016
- 2016-12-30 CN CN201611255498.1A patent/CN106699596A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110698395A (en) * | 2019-10-22 | 2020-01-17 | 杭州百诚医药科技股份有限公司 | Preparation method of topiroxostat intermediate |
| CN110698395B (en) * | 2019-10-22 | 2021-05-25 | 杭州百诚医药科技股份有限公司 | Preparation method of topiroxostat intermediate |
| CN113248351A (en) * | 2021-05-26 | 2021-08-13 | 绍兴上虞新银邦生化有限公司 | Preparation method of 6-chloro-2-methoxytoluene and synthetic process of methoxyfenozide |
| GB2612942A (en) * | 2021-09-16 | 2023-05-24 | Rotam Agrochem Int Co Ltd | A crystalline form of methoxyfenozide, a process for its preparation and use of the same |
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| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20170524 |
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| WD01 | Invention patent application deemed withdrawn after publication |