CN107445920A - A kind of production method of bentazone raw pesticide - Google Patents
A kind of production method of bentazone raw pesticide Download PDFInfo
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- CN107445920A CN107445920A CN201710634542.8A CN201710634542A CN107445920A CN 107445920 A CN107445920 A CN 107445920A CN 201710634542 A CN201710634542 A CN 201710634542A CN 107445920 A CN107445920 A CN 107445920A
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- Prior art keywords
- dichloroethanes
- bentazone
- raw pesticide
- production method
- bentazone raw
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention discloses a kind of production method of bentazone raw pesticide, comprise the following steps：Isatoic anhydride, dichloroethanes and isopropylamine are reacted, is then washed with saturated sodium carbonate and sloughs dichloroethanes, obtain adjacent amino N isopropylbenzamide solution；α picolines are added in adjacent amino N isopropylbenzamide with dichloroethanes and mixed, sulfur trioxide, acid amides dichloroethanes, catalyst and POCl3 solution is added dropwise, after being heated to backflow, it is cooled to room temperature, after hydrolysis alkali cleaning, washing, extracted with sig water, be layered to obtain bentazone sodium salt, it is acidified, filter to obtain faint yellow solid thing, drying bentazone raw pesticide.A kind of production method of bentazone raw pesticide proposed by the present invention, step is few, it is simple to operate, alkali, acid are not used in production process, environmental pollution is small, and production efficiency is high, and the yield of gained bentazone raw pesticide can reach more than 90%, the high purity more than 98.5% of bentazone raw pesticide, it is adapted to industrialized production.
Description
Technical field
The present invention relates to agricultural chemical compound technical field, more particularly to a kind of production method of bentazone raw pesticide.
Background technology
Bentazone is a kind of important herbicide after seedling, its entitled 3- isopropyls-(1H)-benzo -2,1 of chemistry, 3- thiophenes two
Piperazine -4- ketone -2,2- dioxide, it is initially researched and developed successfully by BASF Corp. of Germany and worldwide largely used.
It is a kind of selective killing type herbicide after seedling, and for weeds seedling stage cauline leaf process, the medical instrument has contact strong, selection
Property is good, the features such as seeing careless herbicide, is mainly used in the crops such as rice, soybean, peanut, wheat, prevents and kill off broad leaved weed and Cyperaceae is miscellaneous
Grass is invalid to grassy weed.In the prior art, the preparation technology of bentazone raw pesticide is more using the Bentazon two after synthesis washing
The extraction acidifying washing of chloroethanes solution alkali, and the methods of alkali extraction acidizing extraction concentration.The above method, production cost height be present, it is raw
Production method is complicated, and working condition is harsh, substantial amounts of brine waste pollution is also easy to produce in production process, dust pollution is serious, and institute
It is low to obtain product yield, the problems such as purity is low.Based on above statement, the present invention proposes a kind of production method of bentazone raw pesticide.
The content of the invention
The invention aims to solve shortcoming present in prior art, and a kind of life of the bentazone raw pesticide proposed
Production method.
A kind of production method of bentazone raw pesticide, comprises the following steps：
S1, adjacent amino-N-isopropylbenzamide preparation：Isatoic anhydride is dissolved in dichloroethanes, is added dropwise in heating different
Propylamine, after being warming up to 48~65 DEG C, 0.5~1h is incubated, is then washed with saturated sodium carbonate and sloughs dichloroethanes, obtain light yellow neighbour
Amino-N-isopropylbenzamide solution；
S2, bentazone raw pesticide preparation：Adjacent amino-the N- that α-methylpyridine is added to gained in step S1 with dichloroethanes is different
Mixed in propyl benzamide, sulfur trioxide is added dropwise and generates translucent milky double salt, after stirring 0.4~0.8h at room temperature,
Preheated acid amides dichloroethanes is added, is stirred to after separating out crystalloid acid amides pyridine. sulfur trioxide double salt, adds catalyst,
POCl3 solution is added dropwise again, is heated to flowing back, after reacting 2~3h, is cooled to room temperature, after hydrolysis alkali cleaning, washing, uses diluted alkaline
Liquid extracts, and is layered to obtain bentazone sodium salt, acidified, filter to obtain faint yellow solid thing, drying bentazone raw pesticide.
Preferably, the process route of the production method is as follows：
。
Preferably, the mass ratio of the isatoic anhydride in the step S1, dichloroethanes and isopropylamine is 2~4:2~2.8:1
~2.
Preferably, the catalyst in the step S2 is that mass ratio is 2~2.8:The mixing of 1 Macrogol 600 and KI
Thing.
Preferably, the mass ratio of α-methylpyridine, dichloroethanes and sulfur trioxide is 2~2.5 in the step S2:0.8
~1.8:1~2.
Preferably, the mass ratio of the acid amides dichloroethanes in the step S2, catalyst and POCl3 solution be 1~
1.5:0.3~0.8:2~3.
A kind of production method of bentazone raw pesticide proposed by the present invention, step is few, simple to operate, is not used in production process
Alkali, acid, environmental pollution is small, and production efficiency is high, and the yield of gained bentazone raw pesticide can reach more than 90%, bentazone raw pesticide
High purity more than 98.5%, it is adapted to industrialized production, is worthy to be popularized.
Brief description of the drawings
Fig. 1 proposes a kind of process chart of the production method of bentazone raw pesticide for the present invention.
Embodiment
The present invention is made with reference to specific embodiment further to explain.
Embodiment one
A kind of production method of bentazone raw pesticide proposed by the present invention, comprises the following steps：
S1, adjacent amino-N-isopropylbenzamide preparation：Isatoic anhydride is dissolved in dichloroethanes, is added dropwise in heating different
Propylamine, after being warming up to 48 DEG C, 0.5h is incubated, is then washed with saturated sodium carbonate and sloughs dichloroethanes, obtain light yellow adjacent amino-N-
Isopropylbenzamide solution, wherein, the mass ratio of isatoic anhydride, dichloroethanes and isopropylamine is 2:2:1；
S2, bentazone raw pesticide preparation：Adjacent amino-the N- that α-methylpyridine is added to gained in step S1 with dichloroethanes is different
Mixed in propyl benzamide, sulfur trioxide is added dropwise and generates translucent milky double salt, after stirring 0.4h at room temperature, add warp
The acid amides dichloroethanes of preheating, stir to after separating out crystalloid acid amides pyridine. sulfur trioxide double salt, add catalyst, then be added dropwise
POCl3 solution, it is heated to flowing back, after reacting 2h, is cooled to room temperature, after hydrolysis alkali cleaning, washing, is extracted with sig water, point
Layer bentazone sodium salt, acidified, filter to obtain faint yellow solid thing, drying bentazone raw pesticide, wherein, catalyst is quality
Than for 2:1 Macrogol 600 and KI mixture, the mass ratio of α-methylpyridine, dichloroethanes and sulfur trioxide is 2:
0.8:1, the mass ratio of acid amides dichloroethanes, catalyst and POCl3 solution is 1:0.3:2.
Embodiment two
A kind of production method of bentazone raw pesticide proposed by the present invention, comprises the following steps：
S1, adjacent amino-N-isopropylbenzamide preparation：Isatoic anhydride is dissolved in dichloroethanes, is added dropwise in heating different
Propylamine, after being warming up to 60 DEG C, 0.8h is incubated, is then washed with saturated sodium carbonate and sloughs dichloroethanes, obtain light yellow adjacent amino-N-
Isopropylbenzamide solution, wherein, the mass ratio of isatoic anhydride, dichloroethanes and isopropylamine is 3.5:2.6:1.8；
S2, bentazone raw pesticide preparation：Adjacent amino-the N- that α-methylpyridine is added to gained in step S1 with dichloroethanes is different
Mixed in propyl benzamide, sulfur trioxide is added dropwise and generates translucent milky double salt, after stirring 0.7h at room temperature, add warp
The acid amides dichloroethanes of preheating, stir to after separating out crystalloid acid amides pyridine. sulfur trioxide double salt, add catalyst, then be added dropwise
POCl3 solution, it is heated to flowing back, after reacting 2.8h, is cooled to room temperature, after hydrolysis alkali cleaning, washing, is extracted with sig water,
It is layered to obtain bentazone sodium salt, acidified, filter to obtain faint yellow solid thing, drying bentazone raw pesticide, wherein, catalyst is matter
Amount is than being 2.6:1 Macrogol 600 and KI mixture, the mass ratio of α-methylpyridine, dichloroethanes and sulfur trioxide are
2.4:1.5:1.8, the mass ratio of acid amides dichloroethanes, catalyst and POCl3 solution is 1.4:0.7:2.8.
Embodiment three
A kind of production method of bentazone raw pesticide proposed by the present invention, comprises the following steps：
S1, adjacent amino-N-isopropylbenzamide preparation：Isatoic anhydride is dissolved in dichloroethanes, is added dropwise in heating different
Propylamine, after being warming up to 52 DEG C, 0.6h is incubated, is then washed with saturated sodium carbonate and sloughs dichloroethanes, obtain light yellow adjacent amino-N-
Isopropylbenzamide solution, wherein, the mass ratio of isatoic anhydride, dichloroethanes and isopropylamine is 2.5:2.2:1.2；
S2, bentazone raw pesticide preparation：Adjacent amino-the N- that α-methylpyridine is added to gained in step S1 with dichloroethanes is different
Mixed in propyl benzamide, sulfur trioxide is added dropwise and generates translucent milky double salt, after stirring 0.5h at room temperature, add warp
The acid amides dichloroethanes of preheating, stir to after separating out crystalloid acid amides pyridine. sulfur trioxide double salt, add catalyst, then be added dropwise
POCl3 solution, it is heated to flowing back, after reacting 2.2h, is cooled to room temperature, after hydrolysis alkali cleaning, washing, is extracted with sig water,
It is layered to obtain bentazone sodium salt, acidified, filter to obtain faint yellow solid thing, drying bentazone raw pesticide, wherein, catalyst is matter
Amount is than being 2.2:1 Macrogol 600 and KI mixture, the mass ratio of α-methylpyridine, dichloroethanes and sulfur trioxide are
2.1:1:1.2 the mass ratio of acid amides dichloroethanes, catalyst and POCl3 solution is 1.1:0.4:2.2.
Example IV
A kind of production method of bentazone raw pesticide proposed by the present invention, comprises the following steps：
S1, adjacent amino-N-isopropylbenzamide preparation：Isatoic anhydride is dissolved in dichloroethanes, is added dropwise in heating different
Propylamine, after being warming up to 65 DEG C, 1h is incubated, is then washed with saturated sodium carbonate and sloughs dichloroethanes, it is different to obtain light yellow adjacent amino-N-
Propyl amine aqueous solution, wherein, the mass ratio of isatoic anhydride, dichloroethanes and isopropylamine is 4: 2.8: 2；
S2, bentazone raw pesticide preparation：Adjacent amino-the N- that α-methylpyridine is added to gained in step S1 with dichloroethanes is different
Mixed in propyl benzamide, sulfur trioxide is added dropwise and generates translucent milky double salt, after stirring 0.8h at room temperature, add warp
The acid amides dichloroethanes of preheating, stir to after separating out crystalloid acid amides pyridine. sulfur trioxide double salt, add catalyst, then be added dropwise
POCl3 solution, it is heated to flowing back, after reacting 3h, is cooled to room temperature, after hydrolysis alkali cleaning, washing, is extracted with sig water, point
Layer bentazone sodium salt, acidified, filter to obtain faint yellow solid thing, drying bentazone raw pesticide, wherein, catalyst is quality
Than for 2.8:1 Macrogol 600 and KI mixture, the mass ratio of α-methylpyridine, dichloroethanes and sulfur trioxide are
2.5: 1.8:2, the mass ratio of acid amides dichloroethanes, catalyst and POCl3 solution is 1.5: 0.8: 3.
Embodiment five
A kind of production method of bentazone raw pesticide proposed by the present invention, comprises the following steps：
S1, adjacent amino-N-isopropylbenzamide preparation：Isatoic anhydride is dissolved in dichloroethanes, is added dropwise in heating different
Propylamine, after being warming up to 56 DEG C, 0.8h is incubated, is then washed with saturated sodium carbonate and sloughs dichloroethanes, obtain light yellow adjacent amino-N-
Isopropylbenzamide solution, wherein, the mass ratio of isatoic anhydride, dichloroethanes and isopropylamine is 3:2.4:1.5；
S2, bentazone raw pesticide preparation：Adjacent amino-the N- that α-methylpyridine is added to gained in step S1 with dichloroethanes is different
Mixed in propyl benzamide, sulfur trioxide is added dropwise and generates translucent milky double salt, after stirring 0.6h at room temperature, add warp
The acid amides dichloroethanes of preheating, stir to after separating out crystalloid acid amides pyridine. sulfur trioxide double salt, add catalyst, then be added dropwise
POCl3 solution, it is heated to flowing back, after reacting 2.5h, is cooled to room temperature, after hydrolysis alkali cleaning, washing, is extracted with sig water,
It is layered to obtain bentazone sodium salt, acidified, filter to obtain faint yellow solid thing, drying bentazone raw pesticide, wherein, catalyst is matter
Amount is than being 2.4:1 Macrogol 600 and KI mixture, the mass ratio of α-methylpyridine, dichloroethanes and sulfur trioxide are
2.2:1.4:1.5, the mass ratio of acid amides dichloroethanes, catalyst and POCl3 solution is 1.2:0.5:2.5.
The foregoing is only a preferred embodiment of the present invention, but protection scope of the present invention be not limited thereto,
Any one skilled in the art the invention discloses technical scope in, technique according to the invention scheme and its
Inventive concept is subject to equivalent substitution or change, should all be included within the scope of the present invention.
Claims (6)
1. a kind of production method of bentazone raw pesticide, it is characterised in that comprise the following steps：
S1, adjacent amino-N-isopropylbenzamide preparation：Isatoic anhydride is dissolved in dichloroethanes, is added dropwise in heating different
Propylamine, after being warming up to 48~65 DEG C, 0.5~1h is incubated, is then washed with saturated sodium carbonate and sloughs dichloroethanes, obtain light yellow neighbour
Amino-N-isopropylbenzamide solution；
S2, bentazone raw pesticide preparation：Adjacent amino-the N- that α-methylpyridine is added to gained in step S1 with dichloroethanes is different
Mixed in propyl benzamide, sulfur trioxide is added dropwise and generates translucent milky double salt, after stirring 0.4~0.8h at room temperature,
Preheated acid amides dichloroethanes is added, is stirred to after separating out crystalloid acid amides pyridine. sulfur trioxide double salt, adds catalyst,
POCl3 solution is added dropwise again, is heated to flowing back, after reacting 2~3h, is cooled to room temperature, after hydrolysis alkali cleaning, washing, uses diluted alkaline
Liquid extracts, and is layered to obtain bentazone sodium salt, acidified, filter to obtain faint yellow solid thing, drying bentazone raw pesticide.
A kind of 2. production method of bentazone raw pesticide according to claim 1, it is characterised in that the work of the production method
Skill route is as follows：
。
A kind of 3. production method of bentazone raw pesticide according to claim 1, it is characterised in that the indigo in the step S1
The mass ratio of red acid acid anhydride, dichloroethanes and isopropylamine is 2~4:2~2.8:1~2.
A kind of 4. production method of bentazone raw pesticide according to claim 1, it is characterised in that urging in the step S2
Agent is that mass ratio is 2~2.8:1 Macrogol 600 and KI mixture.
A kind of 5. production method of bentazone raw pesticide according to claim 1, it is characterised in that α in the step S2-
The mass ratio of picoline, dichloroethanes and sulfur trioxide is 2~2.5:0.8~1.8:1~2.
A kind of 6. production method of bentazone raw pesticide according to claim 1, it is characterised in that the acyl in the step S2
The mass ratio of amine dichloroethanes, catalyst and POCl3 solution is 1~1.5:0.3~0.8:2~3.
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| CN201710634542.8A CN107445920A (en) | 2017-07-29 | 2017-07-29 | A kind of production method of bentazone raw pesticide |
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| CN201710634542.8A CN107445920A (en) | 2017-07-29 | 2017-07-29 | A kind of production method of bentazone raw pesticide |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112079793A (en) * | 2020-09-23 | 2020-12-15 | 江苏剑牌农化股份有限公司 | Refining process and equipment for batch production of bentazon |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4139700A (en) * | 1977-07-27 | 1979-02-13 | Monsanto Company | Process for the preparation of bicyclothiadiazinones |
| CN1063688A (en) * | 1991-01-28 | 1992-08-19 | 南开大学 | The synthetic method of Bentazon herbicide |
| CN101863858A (en) * | 2010-06-07 | 2010-10-20 | 江苏绿利来股份有限公司 | Synthetic method of bentazone |
| CN101967109A (en) * | 2010-09-01 | 2011-02-09 | 合肥星宇化学有限责任公司 | Synthesis method of bentazone midbody 2-amino-N-isopropylbenzamide |
-
2017
- 2017-07-29 CN CN201710634542.8A patent/CN107445920A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4139700A (en) * | 1977-07-27 | 1979-02-13 | Monsanto Company | Process for the preparation of bicyclothiadiazinones |
| CN1063688A (en) * | 1991-01-28 | 1992-08-19 | 南开大学 | The synthetic method of Bentazon herbicide |
| CN101863858A (en) * | 2010-06-07 | 2010-10-20 | 江苏绿利来股份有限公司 | Synthetic method of bentazone |
| CN101967109A (en) * | 2010-09-01 | 2011-02-09 | 合肥星宇化学有限责任公司 | Synthesis method of bentazone midbody 2-amino-N-isopropylbenzamide |
Non-Patent Citations (1)
| Title |
|---|
| 顾林玲 等: "除草剂灭草松的市场及开发进展", 《世界农药》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112079793A (en) * | 2020-09-23 | 2020-12-15 | 江苏剑牌农化股份有限公司 | Refining process and equipment for batch production of bentazon |
| CN112079793B (en) * | 2020-09-23 | 2023-08-01 | 江苏剑牌农化股份有限公司 | Refining process and equipment for mass production of bentazone |
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Application publication date: 20171208 |