CN112521344A - Method for producing bentazone - Google Patents
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Abstract
The invention discloses a method for producing bentazone, which has the following reaction mechanism: phthalic anhydride, urea and liquid alkali are subjected to condensation reaction, and then are subjected to esterification reaction with methanol and sodium hypochlorite at low temperature to produce methyl anthranilate. Isopropylamine and chlorosulfonic acid are used to generate isopropylamine sulfonic acid in the presence of dichloroethane, and an alkaline acid-binding agent is added to promote the forward reaction because hydrogen chloride is generated in the reaction process. The isopropylamine sulfonic acid and methyl anthranilate are subjected to salt forming reaction, and then react with sodium methoxide to generate bentazone sodium salt, and the bentazone sodium salt is obtained through acidification; the production method of bentazone has high conversion efficiency in different stages, and can raise the yield of bentazone.
Description
Technical Field
The invention relates to a production method, in particular to a bentazone production method.
Background
The bentazone is a selective seedling-killing herbicide and is used for treating stems and leaves of weeds in the seedling stage. The herbicide composition is mainly used for crops such as rice, soybean, peanut, wheat and the like, and can prevent and kill broadleaf weeds and cyperaceae weeds and remove annual broadleaf weeds and cyperaceae weeds. For example, polygonum aviculare, dayflower, flea decorated, cocklebur, broom cypress, abutilon, maidenhair, cleavers, shepherd's purse, descurainia (artemisia capillaris), purslane, cephalanoplos, polygonum, black nightshade, chickweed, cyperus rotundus, cyperus globifolius, cyperus esculentus, cyperus rotundus, and the like, so the production of the bentazone is very important, and the invention of the production method of the bentazone is necessary.
Disclosure of Invention
The invention provides a method for producing bentazone to solve the problems. The technical scheme adopted by the invention is as follows: a method for producing bentazone uses phthalic anhydride and urea as raw materials,
the reaction apparatus comprises: a condensation reaction kettle, a filter tank, a condensation liquid cooling kettle, a degradation kettle, a primary layering tank, a secondary layering tank, a mother liquid tank, a crude oil storage tank, a synthesis kettle, a hydrolysis layering kettle, a receiving tank, a hydrolysis water tank, a desolventizing kettle, a cyclization kettle and an acidification kettle;
the first step is as follows: adding the phthalic anhydride and the urea into the condensation reaction kettle, heating the condensation reaction kettle through steam, stirring the phthalic anhydride and the urea until the phthalic anhydride and the urea are completely molten, stopping heating the condensation reaction kettle, keeping the temperature of the condensation reaction kettle at 110-115 ℃, carrying out heat preservation reaction for 1h under normal pressure, and reacting the phthalic anhydride and the urea to generate phthalic acid ammonia, water and carbon dioxide, wherein the reaction process is as follows;
the second step is that: cooling the condensation reaction kettle to below 90 ℃;
cooling the condensation reaction kettle by using cold brine, and cooling to room temperature;
thirdly, adding liquid caustic soda with the concentration of 32% into the condensation reaction kettle, stirring and reacting for 1 hour, wherein the ammonium phthalate and the liquid caustic soda react to generate sodium benzoate, and the reaction process is as follows;
fourthly, filtering out impurities from the feed liquid through the filtering groove;
sending the filtered feed liquid to the condensation liquid cooling kettle to be cooled to 5 ℃;
the third step: transferring the material liquid in the condensation liquid cooling kettle to the degradation kettle;
cooling the degradation kettle to below-10 ℃ by freezing saline water;
thirdly, adding the methanol solution with the temperature below-10 ℃ into the degradation kettle, and keeping the temperature of the degradation kettle below-10 ℃;
fourthly, adding a sodium hypochlorite solution with the temperature below-10 ℃ into the degradation kettle, controlling the ambient temperature below 0 ℃ during adding, controlling the dripping process within 20-30 min, and carrying out heat preservation reaction for 40-60 min after dripping, wherein the reaction process is as follows;
the fourth step: adding hot water into the degradation kettle, and stirring until materials in the degradation kettle are dissolved;
transferring materials to the primary layering tank, and standing for 4 hours for layering to separate the materials into mother liquor and lower-layer oily matters;
pumping the lower layer oily matter into the secondary layering tank, and feeding the upper layer mother liquor into the mother liquor tank for recycling;
after the secondary layering tank is settled for 2-3 hours, the lower-layer oily matter is sent to a crude oil storage tank, and a small amount of water generated after settlement is sent to a mother liquid tank;
the fifth step: adding dichloroethane, isopropylamine and triethylamine acid-binding agent into the synthesis kettle, then adding the methyl anthranilate generated in the third step, stirring for 30min, and carrying out a sealed reaction; cooling the synthesis kettle to below 0 ℃ by freezing saline water;
secondly, chlorosulfonic acid is dripped into the synthesis kettle, the reaction temperature is controlled to be 0-20 ℃ in the dripping process, the temperature of the frozen brine is reduced after the dripping process is finished, and then the stirring process is continued for 30min, wherein the reaction process is as follows;
thirdly, cooling the synthesis kettle to below 10 ℃ through frozen saline water, dropwise adding phosphorus oxychloride into the synthesized product, and controlling the condensation reaction temperature to below 30 ℃ in the dropwise adding process; after the dropwise addition, the refrigeration of the frozen brine is closed, the temperature is kept and the stirring is carried out for 30min, and the reaction process is as follows;
fourthly, the condensation reaction in the previous step is sent into the hydrolysis layering kettle, the temperature is raised to 40 ℃, water is added for stirring for 30min, standing is carried out for 30min for layering, the hydrolysate in the upper layer enters the receiving tank, and the water layer enters the hydrolysis water tank for recycling;
and a sixth step: pumping the hydrolysate in the previous step into a desolventizing kettle, stirring, and steaming out dichloroethane at a temperature of less than 90 ℃ and under a pressure of-0.096 Mpa to-0.094 Mpa; after the steaming is finished, cooling to 55 ℃, adding methanol into the desolventizing kettle, and cooling the desolventizing kettle to 25 ℃ through frozen saline water;
transferring materials into the cyclization kettle, adding methanol into the cyclization kettle, and cooling the cyclization kettle to 25 ℃ through frozen brine; dropwise adding 30% sodium methoxide solution into the cyclization kettle, controlling the reaction temperature to be about 25 ℃ in the dropwise adding process, then stirring for 20min, preserving the temperature at 25 ℃ for 1.5h, and evaporating methanol under the conditions of less than 50 ℃, minus 0.096Mpa to minus 0.094Mpa after finishing preserving the temperature; after the methanol distillation is finished, adding water, stirring until the water is dissolved, and transferring the materials to the acidification kettle;
the reactions involved above are as follows:
and regulating the pH value of the ground bentazone to 6-7 by using hydrochloric acid, and after regulation, centrifugally discharging by using a centrifugal machine to obtain the solid bentazone raw powder wet material.
Compared with the prior art, the invention has the beneficial effects that:
1. the invention relates to a method for producing bentazone, which is characterized in that after phthalic anhydride, urea and liquid alkali are subjected to condensation reaction, the yield of a reaction product for generating sodium benzoate is about 98%, the conversion rate is about 98%, and the generation rate of the sodium benzoate is greatly improved.
2. According to the method for producing bentazone, methyl anthranilate is generated after sodium benzoate, methanol and sodium hypochlorite are subjected to esterification reaction, the yield of a reaction product is about 94%, the conversion rate is about 96%, and the generation rate of methyl anthranilate is greatly improved.
3. The invention relates to a bentazone production method, which comprises the steps of generating isopropylamine sulfonate by isopropylamine and chlorosulfonic acid in the presence of triethylamine acid-binding agent, and then carrying out synthetic reaction with methyl anthranilate and phosphorus oxychloride to generate a sulfonamide intermediate, wherein the yield of the reaction product is about 96 percent, the conversion rate is about 98 percent, and the generation rate of the sulfonamide intermediate is greatly improved.
4. The invention relates to a method for producing bentazone, wherein a sulfoamide intermediate and sodium methoxide are subjected to cyclization reaction to generate bentazone sodium salt, and the bentazone sodium salt is generated after acidification, so that the yield of a reaction product in the step is about 96%, the conversion rate is about 96%, and the generation rate of the bentazone is greatly improved.
5. According to the method for producing the bentazone, the high-efficiency conversion of each stage directly improves the high-efficiency generation of the bentazone, the generation rate of the bentazone is further improved, and the total yield is 80.65%.
Drawings
In order to more clearly illustrate the technical solution of the present invention, the drawings needed to be used in the embodiments will be briefly described below, and it is obvious to those skilled in the art that other drawings can be obtained according to the drawings without making any inventive changes.
FIG. 1 is an overall flow chart of the present invention.
Detailed Description
In order to make those skilled in the art better understand the technical solutions in the present application, the technical solutions in the embodiments of the present application will be described clearly and completely with reference to the accompanying drawings.
The core of the invention is to provide a method for producing bentazone, which has high efficiency conversion in each stage, directly improves the high efficiency generation of the bentazone, and further improves the generation rate of the bentazone.
FIG. 1 is an overall flow chart of the present invention. As shown in fig. 1, the reaction mechanism of the bentazone production in the invention is as follows: phthalic anhydride, urea and liquid alkali are subjected to condensation reaction, and then are subjected to esterification reaction with methanol and sodium hypochlorite at low temperature to produce methyl anthranilate. Isopropylamine and chlorosulfonic acid are used to generate isopropylamine sulfonic acid in the presence of dichloroethane, and an alkaline acid-binding agent is added to promote the forward reaction because hydrogen chloride is generated in the reaction process. The isopropylamine sulfonic acid and methyl anthranilate are subjected to salt forming reaction, and then reacted with sodium methoxide to generate bentazone sodium salt, and the bentazone sodium salt is obtained through acidification.
The production process of the bentazone water agent mainly comprises five procedures of condensation, esterification, synthesis, cyclization and triethylamine recovery.
1. Condensation: the benzoic anhydride, the urea and the liquid alkali are subjected to condensation reaction to generate sodium benzoate.
The main reaction formula is as follows:
the main side reaction formula is as follows:
the yield of the reaction product in the step is about 98 percent, and the conversion rate is about 98 percent. About 2% of phthalic anhydride produces o-dibenzoic acid as a side reaction of hydrolysis, which is carried over to the next step.
The process flow is illustrated as follows: adding phthalic anhydride and urea into a condensation reaction kettle, starting stirring, introducing steam into a kettle jacket for heating, stopping heating when the materials are completely molten, keeping the temperature at 110-115 ℃, and carrying out heat preservation reaction for 1 hour under normal pressure. Cooling circulating water to below 90 ℃, adding a certain amount of fresh water into the condensation reaction kettle through the high-level metering tank, continuously cooling the cooling water to about room temperature, adding a certain amount of 32% liquid alkali through the liquid alkali metering tank, stirring and reacting for 1h, putting feed liquid into the filter tank, pumping the feed liquid into the condensation liquid cooling kettle, and cooling the feed liquid to below 5 ℃ by using cooling brine for later use.
2. Esterification: sodium benzoate, methanol and sodium hypochlorite are subjected to esterification reaction to generate methyl anthranilate.
The main reaction formula is as follows:
the main side reactions are as follows:
the yield of the reaction product in the step is about 94 percent, and the conversion rate is about 96 percent. About 2% of methyl anthranilate remained in the wastewater, and about 4% of the side reaction sodium anthranilate remained in the wastewater.
The process flow is illustrated as follows: transferring the condensed materials to a degradation kettle, and continuously cooling to below-10 ℃ by using a freezing saline coil. Cooling the methanol solution and the sodium hypochlorite solution to below-10 ℃, adding the cooled methanol solution into a degradation kettle, dropwise adding the cooled sodium hypochlorite solution when the temperature in the degradation kettle is reduced to below-10 ℃, controlling the dropwise adding process to be 20-30 min, controlling the temperature below 0 ℃ after the dropwise adding is finished, continuing to perform heat preservation reaction for 40-60 min after the dropwise adding is finished, closing a coil pipe and a jacket to freeze brine, and blowing away by using air pressure. And then adding a certain amount of hot water into the degradation kettle, stirring and dissolving the materials, and transferring the materials to a primary layering tank. Standing for 4h for layering, pumping the lower layer oily matter into a secondary layering tank through a vacuum filtration tank, and pumping the upper layer mother liquor into a mother liquor tank by a pump for recovering methanol. And after the secondary layering tank is settled for 2-3 hours, metering the lower oily matter and pumping into a crude oil storage tank, and sending a small amount of water into a mother liquid tank. Rectifying the methanol-containing wastewater in the mother liquor tank to recover methanol, and then sending the methanol-containing wastewater to a wastewater treatment system for treatment.
3. Synthesizing: isopropylamine and chlorosulfonic acid generate isopropylamine sulfonate in the presence of triethylamine acid-binding agent, and then the isopropylamine sulfonate, methyl anthranilate and phosphorus oxychloride undergo a synthetic reaction to generate a sulfonamide intermediate.
The main reaction formula is as follows:
the main side reactions are as follows:
the yield of the reaction product in the step is about 96 percent, and the conversion rate is about 98 percent. About 2% of methyl anthranilate remains in dichloroethane and is carried into the next process, about 2% of side reaction sulfonamide methyl benzoate is decomposed by heating to generate methyl ester, and the methyl ester is carried into the next process along with the solvent, and the generated sulfonate is carried into the next process along with the water phase.
The process flow is illustrated as follows: adding a certain amount of 1, 2-dichloroethane, isopropylamine and triethylamine into a synthesis kettle from an overhead tank, adding a certain amount of methyl anthranilate into the synthesis kettle, stirring for 30min, sealing the synthesis kettle, cooling the kettle to below 0 ℃ by using frozen saline, dropwise adding chlorosulfonic acid into the synthesis kettle, and controlling the sulfonation reaction temperature to be 0-20 ℃ in the dropwise adding process; and after the dropwise addition is finished, closing the frozen saline water, and continuously stirring for 30min to obtain the sulfonation reaction solution. The hydrogen chloride generated in the synthesis process and triethylamine are subjected to neutralization reaction to generate triethylamine hydrochloride, and the reaction is promoted to be further carried out towards a required product. Cooling the synthesis kettle to below 10 ℃ by using frozen brine, dropwise adding phosphorus oxychloride into the synthesis kettle, and controlling the condensation reaction temperature to be below 30 ℃ in the dropwise adding process; and (4) stopping the frozen saline water after the dropwise addition is finished, and stirring for 30min under the condition of heat preservation to obtain a condensation reaction liquid. The hydrogen chloride generated in the condensation process and triethylamine are subjected to neutralization reaction to generate triethylamine hydrochloride, and the reaction is promoted to be further carried out towards a required product. Adding a certain amount of water into the hydrolysis layering kettle from a high-level water tank, starting stirring, slowly adding the condensation reaction liquid in the previous step into the hydrolysis layering kettle, hydrolyzing to remove excessive phosphorus oxychloride, and heating to about 40 ℃; and after hydrolysis is finished, stirring for 30min, standing for 30min for layering, separating an upper organic layer into a hydrolysis liquid receiving tank, separating a water layer into a hydrolysis water tank, and removing triethylamine for recovery.
4. Cyclization: and (3) carrying out cyclization reaction on the amine sulfonate intermediate and sodium methoxide to generate bentazone sodium salt, and acidifying to generate bentazone.
The main reaction formula is as follows:
the main side reactions are as follows:
the yield of the reaction product in the step is about 96 percent, and the conversion rate is about 96 percent. During the heat preservation reaction process of adding methanol and sodium methoxide into about 4 percent of sulfonic acid methyl aminobenzoate, the sulfonic acid methyl aminobenzoate is heated and decomposed when meeting water and remains in a methanol system and is finally brought into acidified centrifugal wastewater.
The process flow is illustrated as follows: pumping the organic layer in the hydrolysate receiving tank into a desolventizing kettle, stirring, and distilling off dichloroethane to enter a dichloroethane receiving tank (for feeding) under the conditions of less than 90 ℃ and minus 0.095 MPa; after the steaming is finished, cooling to 55 ℃, adding a certain amount of methanol into a desolventizing kettle, cooling the kettle to 25 ℃ by using frozen brine, transferring materials into a cyclization kettle, transferring the materials into the cyclization kettle, beginning to dropwise add 30% sodium methoxide methanol solution into the cyclization kettle, controlling the reaction temperature to be about 25 ℃ in the dropwise adding process, finishing the dropwise adding, stirring for 20min, preserving the temperature for 1.5h at 25 ℃, finishing the heat preservation, and distilling out the methanol into a methanol receiving tank under the conditions of less than 50 ℃ and-0.095 MPa. After the methanol distillation is finished, adding quantitative fresh water, stirring and dissolving, and transferring the materials to an acidification kettle. Adding a certain amount of water into an acidification kettle, adjusting the pH value to 6-7 with hydrochloric acid, after the adjustment, centrifugally discharging by using a centrifugal machine to obtain a solid bentazone raw powder wet material, sending the wet material to a flash evaporation drying packaging workshop, and treating the centrifugal wastewater decontamination water treatment system. The process can generate a tail gas G1-4 for recovering the dichloroethane noncondensable gas. There is a tail gas G1-5 of the recovered methanol non-condensable gas. There will be a tail gas G1-6 of the non-condensable gas of the bentazone drying water. Waste water W1-3 is generated after the product is centrifuged.
5. And (3) recovering triethylamine: neutralizing triethylamine hydrochloride with liquid alkali, and recovering triethylamine.
The main reaction formula is as follows:
the reaction in this step is non-reactive, and the yield and conversion rate are about 100%. About 4% of the ethylene dichloride removed by distillation undergoes side reactions and remains in the ethylene dichloride to be carried over to the next process.
The process flow is illustrated as follows: pumping a hydrolysis water tank process water into a triethylamine recovery kettle, dropwise adding alkali liquor into the kettle to adjust the pH value to be neutral, and controlling the temperature to be 60 ℃ in the dropwise adding process; after the dropwise addition, the temperature is raised, and the triethylamine is distilled and rectified. And (3) rectifying the triethylamine until the water content is less than or equal to 0.5 percent, wherein the qualified triethylamine is fed into a recovery tank for use in the synthesis process. The process generates the tail gas G1-3 of the triethylamine recovery non-condensable gas. The process can generate waste water W1-2 after triethylamine is recovered.
The total yield of the product is as follows: the total yield of the product is calculated by taking phthalic anhydride as a raw material, and the total yield of the bentazone raw powder is 80.65 percent.
Other embodiments of the present application will be apparent to those skilled in the art from consideration of the specification and practice of the application disclosed herein. This application is intended to cover any variations, uses, or adaptations of the invention following, in general, the principles of the application and including such departures from the present disclosure as come within known or customary practice in the art to which the invention pertains. It is intended that the specification and examples be considered as exemplary only, with a true scope of the disclosure being indicated by the following claims.
It will be understood that the present application is not limited to the precise arrangements described above and shown in the drawings and that various modifications and changes may be made without departing from the scope thereof. The above-described embodiments of the present application do not limit the scope of the present application.
Claims (5)
1. A method for producing bentazone is characterized in that: phthalic anhydride and urea are used as raw materials,
the reaction apparatus comprises: a condensation reaction kettle, a filter tank, a condensation liquid cooling kettle, a degradation kettle, a primary layering tank, a secondary layering tank, a mother liquid tank, a crude oil storage tank, a synthesis kettle, a hydrolysis layering kettle, a receiving tank, a hydrolysis water tank, a desolventizing kettle, a cyclization kettle and an acidification kettle;
the first step is as follows: adding the phthalic anhydride and the urea into the condensation reaction kettle, heating the condensation reaction kettle through steam, stirring the phthalic anhydride and the urea until the phthalic anhydride and the urea are completely molten, stopping heating the condensation reaction kettle, keeping the temperature of the condensation reaction kettle at 110-115 ℃, carrying out heat preservation reaction for 1h under normal pressure, and reacting the phthalic anhydride and the urea to generate phthalic acid ammonia, water and carbon dioxide, wherein the reaction process is as follows;
the second step is that: cooling the condensation reaction kettle to below 90 ℃;
cooling the condensation reaction kettle by using cold brine, and cooling to room temperature;
thirdly, adding liquid caustic soda with the concentration of 32% into the condensation reaction kettle, stirring and reacting for 1 hour, wherein the ammonium phthalate and the liquid caustic soda react to generate sodium benzoate, and the reaction process is as follows;
fourthly, filtering out impurities from the feed liquid through the filtering groove;
sending the filtered feed liquid to the condensation liquid cooling kettle to be cooled to 5 ℃;
the third step: transferring the material liquid in the condensation liquid cooling kettle to the degradation kettle;
cooling the degradation kettle to below-10 ℃ by freezing saline water;
thirdly, adding the methanol solution with the temperature below-10 ℃ into the degradation kettle, and keeping the temperature of the degradation kettle below-10 ℃;
fourthly, adding a sodium hypochlorite solution with the temperature below-10 ℃ into the degradation kettle, controlling the ambient temperature below 0 ℃ during adding, controlling the dripping process within 20-30 min, and carrying out heat preservation reaction for 40-60 min after dripping, wherein the reaction process is as follows;
the fourth step: adding hot water into the degradation kettle, and stirring until materials in the degradation kettle are dissolved;
transferring materials to the primary layering tank, and standing for 4 hours for layering to separate the materials into mother liquor and lower-layer oily matters;
pumping the lower layer oily matter into the secondary layering tank, and feeding the upper layer mother liquor into the mother liquor tank for recycling;
after the secondary layering tank is settled for 2-3 hours, the lower-layer oily matter is sent to a crude oil storage tank, and a small amount of water generated after settlement is sent to a mother liquid tank;
the fifth step: adding dichloroethane, isopropylamine and triethylamine acid-binding agent into the synthesis kettle, then adding the methyl anthranilate generated in the third step, stirring for 30min, and carrying out a sealed reaction; cooling the synthesis kettle to below 0 ℃ by freezing saline water;
secondly, chlorosulfonic acid is dripped into the synthesis kettle, the reaction temperature is controlled to be 0-20 ℃ in the dripping process, the temperature of the frozen brine is reduced after the dripping process is finished, and then the stirring process is continued for 30min, wherein the reaction process is as follows;
thirdly, cooling the synthesis kettle to below 10 ℃ through frozen saline water, dropwise adding phosphorus oxychloride into the synthesized product, and controlling the condensation reaction temperature to below 30 ℃ in the dropwise adding process; after the dropwise addition, the refrigeration of the frozen brine is closed, the temperature is kept and the stirring is carried out for 30min, and the reaction process is as follows;
fourthly, the condensation reaction in the previous step is sent into the hydrolysis layering kettle, the temperature is raised to 40 ℃, water is added for stirring for 30min, standing is carried out for 30min for layering, the hydrolysate in the upper layer enters the receiving tank, and the water layer enters the hydrolysis water tank for recycling;
and a sixth step: pumping the hydrolysate in the previous step into a desolventizing kettle, stirring, and steaming out dichloroethane at a temperature of less than 90 ℃ and under a pressure of-0.096 Mpa to-0.094 Mpa; after the steaming is finished, cooling to 55 ℃, adding methanol into the desolventizing kettle, and cooling the desolventizing kettle to 25 ℃ through frozen saline water;
transferring materials into the cyclization kettle, adding methanol into the cyclization kettle, and cooling the cyclization kettle to 25 ℃ through frozen brine; dropwise adding 30% sodium methoxide solution into the cyclization kettle, controlling the reaction temperature to be about 25 ℃ in the dropwise adding process, then stirring for 20min, preserving the temperature at 25 ℃ for 1.5h, and evaporating methanol under the conditions of less than 50 ℃, minus 0.096Mpa to minus 0.094Mpa after finishing preserving the temperature; after the methanol distillation is finished, adding water, stirring until the water is dissolved, and transferring the materials to the acidification kettle;
the reactions involved above are as follows:
and regulating the pH value of the ground bentazone to 6-7 by using hydrochloric acid, and after regulation, centrifugally discharging by using a centrifugal machine to obtain the solid bentazone raw powder wet material.
2. The bentazone production method according to claim 1, wherein a kettle jacket is externally sleeved on the condensation reaction kettle, and the condensation reaction kettle is heated by introducing steam into the kettle jacket.
3. The method for producing bentazone according to claim 1, wherein a high-level metering tank is installed in the condensation reaction kettle, and cooling water is added into the condensation reaction kettle through the high-level metering tank.
4. The bentazone production method according to claim 1, wherein the reaction apparatus further comprises: and the lower-layer oily substance is pumped into the secondary layering tank through the vacuum filtration tank.
5. The method for producing bentazone according to claim 1, wherein the mother liquor in the mother liquor tank contains methanol, and the mother liquor is rectified to recover methanol and then sent to a wastewater treatment system for treatment.
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| CN114989025A (en) * | 2022-05-30 | 2022-09-02 | 沈阳万菱生物技术有限公司 | Preparation method of 2-amino-6-methyl benzoate |
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