CN113429347A - Preparation method of high-purity mefenpyr-diethyl - Google Patents
Preparation method of high-purity mefenpyr-diethyl Download PDFInfo
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- CN113429347A CN113429347A CN202110475542.4A CN202110475542A CN113429347A CN 113429347 A CN113429347 A CN 113429347A CN 202110475542 A CN202110475542 A CN 202110475542A CN 113429347 A CN113429347 A CN 113429347A
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- mefenpyr
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- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 238000005886 esterification reaction Methods 0.000 claims abstract description 18
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 18
- 239000007787 solid Substances 0.000 claims abstract description 16
- 238000006193 diazotization reaction Methods 0.000 claims abstract description 13
- 238000005070 sampling Methods 0.000 claims abstract description 9
- 238000005303 weighing Methods 0.000 claims abstract description 9
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000002844 melting Methods 0.000 claims abstract description 6
- 230000008018 melting Effects 0.000 claims abstract description 6
- 238000004806 packaging method and process Methods 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
- 238000003756 stirring Methods 0.000 claims description 35
- 239000000463 material Substances 0.000 claims description 30
- 238000005086 pumping Methods 0.000 claims description 30
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 238000001816 cooling Methods 0.000 claims description 20
- 235000010288 sodium nitrite Nutrition 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000012954 diazonium Substances 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 13
- 230000032050 esterification Effects 0.000 claims description 12
- 239000012267 brine Substances 0.000 claims description 10
- 239000000498 cooling water Substances 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 10
- 150000001989 diazonium salts Chemical class 0.000 claims description 10
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 10
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 10
- 238000000967 suction filtration Methods 0.000 claims description 8
- 150000007857 hydrazones Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 6
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 claims description 5
- 238000007599 discharging Methods 0.000 claims description 5
- RDULEYWUGKOCMR-UHFFFAOYSA-N ethyl 2-chloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(C)=O RDULEYWUGKOCMR-UHFFFAOYSA-N 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 5
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 5
- 239000011736 potassium bicarbonate Substances 0.000 claims description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 5
- 235000010265 sodium sulphite Nutrition 0.000 claims description 5
- 238000004065 wastewater treatment Methods 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 4
- 238000003828 vacuum filtration Methods 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 description 2
- PQKBPHSEKWERTG-UHFFFAOYSA-N Fenoxaprop ethyl Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-UHFFFAOYSA-N 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of high-purity mefenpyr-diethyl, which comprises the steps of obtaining mefenpyr-diethyl solid by adopting diazotization reaction esterification reaction and cyclization reaction, drying or melting and slicing, obtaining the mefenpyr-diethyl, packaging, weighing, sampling, analyzing, numbering and warehousing.
Description
Technical Field
The invention relates to the field of pesticides, and particularly relates to a preparation method of high-purity mefenpyr-diethyl.
Background
The mefenpyr-diethyl is a chemical product with the molecular formula of C16H18Cl2N2O 4. The fenoxaprop-ethyl is a safener for wheat, barley and the like, the existing mefenpyr-diethyl is not high enough in purity in the preparation process, the effect of the mefenpyr-diethyl is often not exerted in the use process, the performance of pesticides is affected, the crop yield is low, and the loss is caused.
Disclosure of Invention
The invention aims to provide a preparation method of high-purity mefenpyr-diethyl, aiming at overcoming the defects in the prior art and solving the problems in the prior art.
In order to achieve the purpose, the invention provides the following technical scheme: a preparation method of high-purity mefenpyr-diethyl comprises the following specific steps:
s1: diazotization reaction;
s2: performing esterification reaction;
s3: and (3) carrying out cyclization reaction.
As a preferred technical solution of the present invention, the specific step in S1 is:
s11: putting water into a metering tank, putting a sodium nitrite preparation kettle, stirring, putting sodium nitrite, fully dissolving, pumping a sodium nitrite solution into the metering tank;
s12: pumping hydrochloric acid into a metering tank from a hydrochloric acid transfer tank, and putting into a diazotization kettle; firstly stirring, then adding 2, 4-dichloroaniline, and opening a kettle jacket to refrigerate brine for cooling;
s13: and when the temperature of the kettle is reduced to below 5 ℃, beginning to dropwise add the sodium sulfite solution, controlling the reaction temperature to be 0-5 ℃, ending dropwise adding within about 10 hours, preserving the temperature for 0.5 hour, and informing an esterification post to pass the materials after ending.
As a preferred technical solution of the present invention, the specific step in S2 is:
s21: pumping 2-chloroacetoacetic acid ethyl ester into an esterification kettle in vacuum, putting water into a metering tank and then into the kettle, stirring, and cooling water;
s22: feeding the diazonium salt from the diazonium kettle into a metering tank, beginning to dropwise add the diazonium salt, controlling the reaction temperature to be 20-35 ℃, and dropwise adding for about 10 hours;
s23: after the reaction is finished, the materials are put into a suction filtration tank, vacuum filtration is carried out, the solid is centrifuged again, the filtrate is sent to a wastewater treatment station, the solid wet material is the intermediate hydrazone, and the intermediate hydrazone is packaged, weighed, sampled and analyzed, and handed over to the next station for use.
As a preferred technical solution of the present invention, the specific step in S3 is:
s31: putting water into a cyclization kettle, stirring, and putting potassium bicarbonate;
s32: pumping ethyl methacrylate into a cyclization kettle, adding the chlorohydrazone, and stirring for reaction at 30-40 ℃ for 12 hours;
s33: after the reaction is finished, the materials are fed into a desolventizing kettle, steam is released from a kettle jacket, and redundant ethyl methacrylate is desolventized under negative pressure and recycled; the negative pressure desolventizing temperature is not more than 118 ℃, and cooling water is opened for cooling after desolventizing is finished;
s34: pumping methanol from a methanol storage tank into a metering tank, and adding the methanol when the temperature is reduced to about 50 ℃; fully stirring, feeding the materials to a crystallization kettle, starting stirring, and starting a jacket of the crystallization kettle to freeze brine for cooling and crystallizing;
s35: cooling to below 0 deg.c, discharging material and centrifuging, and pumping mother liquid into methanol distilling still; drying or melting the solid, slicing to obtain the product of the mefenpyr-diethyl, packaging, weighing, sampling, analyzing, numbering and warehousing.
The invention has the beneficial effects that: the process can rapidly prepare the mefenpyr-diethyl by adopting diazotization, esterification and cyclization reactions, can improve the purity of the mefenpyr-diethyl, improves the preparation efficiency, saves time, improves the yield, saves the cost and increases the income.
Detailed Description
The following detailed description of the preferred embodiments of the present invention is provided to enable those skilled in the art to more readily understand the advantages and features of the present invention and to clearly define the scope of the invention.
Example 1: the invention provides a technical scheme that: a preparation method of high-purity mefenpyr-diethyl comprises the following specific steps:
s1: diazotization reaction;
s11: putting water into a metering tank, putting a sodium nitrite preparation kettle, stirring, putting sodium nitrite, fully dissolving, pumping a sodium nitrite solution into the metering tank;
s12: pumping hydrochloric acid into a metering tank from a hydrochloric acid transfer tank, and putting into a diazotization kettle; firstly stirring, then adding 2, 4-dichloroaniline, and opening a kettle jacket to refrigerate brine for cooling;
s13: when the temperature of the kettle is reduced to below 5 ℃, beginning to dropwise add the sodium sulfite solution, controlling the reaction temperature to be 2 ℃, ending the dropwise adding within about 10 hours, preserving the temperature for 0.5 hour, and informing an esterification post to pass the materials after the dropwise adding is ended;
s2: performing esterification reaction;
s21: pumping 2-chloroacetoacetic acid ethyl ester into an esterification kettle in vacuum, putting water into a metering tank and then into the kettle, stirring, and cooling water;
s22: feeding the diazonium salt from the diazonium kettle into a metering tank, beginning to dropwise add the diazonium salt, controlling the reaction temperature to be 20 ℃, and dropwise adding for about 10 hours;
s23: after the reaction is finished, putting the materials into a suction filtration tank, carrying out vacuum suction filtration, centrifuging the solid again, removing the filtrate from a wastewater treatment station to obtain a solid wet material, namely the intermediate hydrazone, bagging, weighing, sampling, analyzing and transferring to the next station for use;
s3: performing cyclization reaction;
s31: putting water into a cyclization kettle, stirring, and putting potassium bicarbonate;
s32: pumping the ethyl methacrylate into a cyclization kettle, adding the chlorohydrazone, and stirring for reaction at 30 ℃ for 12 hours;
s33: after the reaction is finished, the materials are fed into a desolventizing kettle, steam is released from a kettle jacket, and redundant ethyl methacrylate is desolventized under negative pressure and recycled; the negative pressure desolventizing temperature is not more than 118 ℃, and cooling water is opened for cooling after desolventizing is finished;
s34: pumping methanol from a methanol storage tank into a metering tank, and adding the methanol when the temperature is reduced to about 50 ℃; fully stirring, feeding the materials to a crystallization kettle, starting stirring, and starting a jacket of the crystallization kettle to freeze brine for cooling and crystallizing;
s35: cooling to below 0 deg.c, discharging material and centrifuging, and pumping mother liquid into methanol distilling still; drying or melting the solid, slicing to obtain the product of the mefenpyr-diethyl, packaging, weighing, sampling, analyzing, numbering and warehousing.
Example 2: a preparation method of high-purity mefenpyr-diethyl,
the method comprises the following specific steps:
s1: diazotization reaction;
s11: putting water into a metering tank, putting a sodium nitrite preparation kettle, stirring, putting sodium nitrite, fully dissolving, pumping a sodium nitrite solution into the metering tank;
s12: pumping hydrochloric acid into a metering tank from a hydrochloric acid transfer tank, and putting into a diazotization kettle; firstly stirring, then adding 2, 4-dichloroaniline, and opening a kettle jacket to refrigerate brine for cooling;
s13: when the temperature of the kettle is reduced to below 5 ℃, beginning to dropwise add the sodium sulfite solution, controlling the reaction temperature to be 4 ℃, ending the dropwise adding within about 10 hours, preserving the temperature for 0.5 hour, and informing an esterification post to pass the materials after the dropwise adding is ended;
s2: performing esterification reaction;
s21: pumping 2-chloroacetoacetic acid ethyl ester into an esterification kettle in vacuum, putting water into a metering tank and then into the kettle, stirring, and cooling water;
s22: feeding the diazonium salt from the diazonium kettle into a metering tank, beginning to dropwise add the diazonium salt, controlling the reaction temperature to be 30 ℃, and dropwise adding for about 10 hours;
s23: after the reaction is finished, putting the materials into a suction filtration tank, carrying out vacuum suction filtration, centrifuging the solid again, removing the filtrate from a wastewater treatment station to obtain a solid wet material, namely the intermediate hydrazone, bagging, weighing, sampling, analyzing and transferring to the next station for use;
s3: performing cyclization reaction;
s31: putting water into a cyclization kettle, stirring, and putting potassium bicarbonate;
s32: pumping the ethyl methacrylate into a cyclization kettle, adding the chlorohydrazone, and stirring to react for 12 hours at 35 ℃;
s33: after the reaction is finished, the materials are fed into a desolventizing kettle, steam is released from a kettle jacket, and redundant ethyl methacrylate is desolventized under negative pressure and recycled; the negative pressure desolventizing temperature is not more than 118 ℃, and cooling water is opened for cooling after desolventizing is finished;
s34: pumping methanol from a methanol storage tank into a metering tank, and adding the methanol when the temperature is reduced to about 50 ℃; fully stirring, feeding the materials to a crystallization kettle, starting stirring, and starting a jacket of the crystallization kettle to freeze brine for cooling and crystallizing;
s35: cooling to below 0 deg.c, discharging material and centrifuging, and pumping mother liquid into methanol distilling still; drying or melting the solid, slicing to obtain the product of the mefenpyr-diethyl, packaging, weighing, sampling, analyzing, numbering and warehousing.
Example 3: a preparation method of high-purity mefenpyr-diethyl,
s1: diazotization reaction;
s11: putting water into a metering tank, putting a sodium nitrite preparation kettle, stirring, putting sodium nitrite, fully dissolving, pumping a sodium nitrite solution into the metering tank;
s12: pumping hydrochloric acid into a metering tank from a hydrochloric acid transfer tank, and putting into a diazotization kettle; firstly stirring, then adding 2, 4-dichloroaniline, and opening a kettle jacket to refrigerate brine for cooling;
s13: when the temperature of the kettle is reduced to below 5 ℃, beginning to dropwise add the sodium sulfite solution, controlling the reaction temperature to be 5 ℃, ending the dropwise adding within about 10 hours, preserving the temperature for 0.5 hour, and informing an esterification post to feed the materials after the dropwise adding is ended;
s2: performing esterification reaction;
s21: pumping 2-chloroacetoacetic acid ethyl ester into an esterification kettle in vacuum, putting water into a metering tank and then into the kettle, stirring, and cooling water;
s22: feeding the diazonium salt from the diazo kettle to a metering tank, beginning to dropwise add the diazonium salt, controlling the reaction temperature to be 35 ℃, and dropwise adding for about 10 hours;
s23: after the reaction is finished, putting the materials into a suction filtration tank, carrying out vacuum suction filtration, centrifuging the solid again, removing the filtrate from a wastewater treatment station to obtain a solid wet material, namely the intermediate hydrazone, bagging, weighing, sampling, analyzing and transferring to the next station for use;
s3: performing cyclization reaction;
s31: putting water into a cyclization kettle, stirring, and putting potassium bicarbonate;
s32: pumping the ethyl methacrylate into a cyclization kettle, adding the chlorohydrazone, and stirring to react for 12 hours at 40 ℃;
s33: after the reaction is finished, the materials are fed into a desolventizing kettle, steam is released from a kettle jacket, and redundant ethyl methacrylate is desolventized under negative pressure and recycled; the negative pressure desolventizing temperature is not more than 118 ℃, and cooling water is opened for cooling after desolventizing is finished;
s34: pumping methanol from a methanol storage tank into a metering tank, and adding the methanol when the temperature is reduced to about 50 ℃; fully stirring, feeding the materials to a crystallization kettle, starting stirring, and starting a jacket of the crystallization kettle to freeze brine for cooling and crystallizing;
s35: cooling to below 0 deg.c, discharging material and centrifuging, and pumping mother liquid into methanol distilling still; drying or melting the solid, slicing to obtain the product of the mefenpyr-diethyl, packaging, weighing, sampling, analyzing, numbering and warehousing.
The process can rapidly prepare the mefenpyr-diethyl by adopting diazotization, esterification and cyclization reactions, can improve the purity of the mefenpyr-diethyl, improves the preparation efficiency, saves time, improves the yield, saves the cost and increases the income.
The above examples only show some embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention.
Claims (4)
1. The preparation method of the high-purity mefenpyr-diethyl is characterized by comprising the following specific steps of:
s1: diazotization reaction;
s2: performing esterification reaction;
s3: and (3) carrying out cyclization reaction.
2. The method for preparing high-purity mefenpyr-diethyl according to claim 1, which is characterized in that: the specific steps in S1 are:
s11: putting water into a metering tank, putting a sodium nitrite preparation kettle, stirring, putting sodium nitrite, fully dissolving, pumping a sodium nitrite solution into the metering tank;
s12: pumping hydrochloric acid into a metering tank from a hydrochloric acid transfer tank, and putting into a diazotization kettle; firstly stirring, then adding 2, 4-dichloroaniline, and opening a kettle jacket to refrigerate brine for cooling;
s13: and when the temperature of the kettle is reduced to below 5 ℃, beginning to dropwise add the sodium sulfite solution, controlling the reaction temperature to be 0-5 ℃, ending dropwise adding within about 10 hours, preserving the temperature for 0.5 hour, and informing an esterification post to pass the materials after ending.
3. The method for preparing high-purity mefenpyr-diethyl according to claim 1, which is characterized in that: the specific steps in S2 are:
s21: pumping 2-chloroacetoacetic acid ethyl ester into an esterification kettle in vacuum, putting water into a metering tank and then into the kettle, stirring, and cooling water;
s22: feeding the diazonium salt from the diazonium kettle into a metering tank, beginning to dropwise add the diazonium salt, controlling the reaction temperature to be 20-35 ℃, and dropwise adding for about 10 hours;
s23: after the reaction is finished, the materials are put into a suction filtration tank, vacuum filtration is carried out, the solid is centrifuged again, the filtrate is sent to a wastewater treatment station, the solid wet material is the intermediate hydrazone, and the intermediate hydrazone is packaged, weighed, sampled and analyzed, and handed over to the next station for use.
4. The method for preparing high-purity mefenpyr-diethyl according to claim 1, which is characterized in that: the specific steps in S3 are:
s31: putting water into a cyclization kettle, stirring, and putting potassium bicarbonate;
s32: pumping ethyl methacrylate into a cyclization kettle, adding the chlorohydrazone, and stirring for reaction at 30-40 ℃ for 12 hours;
s33: after the reaction is finished, the materials are fed into a desolventizing kettle, steam is released from a kettle jacket, and redundant ethyl methacrylate is desolventized under negative pressure and recycled; the negative pressure desolventizing temperature is not more than 118 ℃, and cooling water is opened for cooling after desolventizing is finished;
s34: pumping methanol from a methanol storage tank into a metering tank, and adding the methanol when the temperature is reduced to about 50 ℃; fully stirring, feeding the materials to a crystallization kettle, starting stirring, and starting a jacket of the crystallization kettle to freeze brine for cooling and crystallizing;
s35: cooling to below 0 deg.c, discharging material and centrifuging, and pumping mother liquid into methanol distilling still; drying or melting the solid, slicing to obtain the product of the mefenpyr-diethyl, packaging, weighing, sampling, analyzing, numbering and warehousing.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114989040A (en) * | 2022-07-07 | 2022-09-02 | 南京正荣医药化学有限公司 | Synthetic method of mefenpyr-diethyl intermediate |
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|---|---|---|---|---|
| CN102816118A (en) * | 2012-06-13 | 2012-12-12 | 江苏天容集团股份有限公司 | Catalytic synthesis method of mefenpyr-diethyl |
| US20170158641A1 (en) * | 2015-12-02 | 2017-06-08 | Rotam Agrochem International Company Limited | Novel form of mefenpyr-diethyl, a process for its preparation and use of the same |
| CN110003107A (en) * | 2019-04-28 | 2019-07-12 | 东华大学 | A kind of synthetic method of mefenpyrdiethyl |
| CN111592493A (en) * | 2020-05-30 | 2020-08-28 | 上海赫腾精细化工有限公司 | Preparation method of mefenpyr-diethyl |
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2021
- 2021-04-29 CN CN202110475542.4A patent/CN113429347A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102816118A (en) * | 2012-06-13 | 2012-12-12 | 江苏天容集团股份有限公司 | Catalytic synthesis method of mefenpyr-diethyl |
| US20170158641A1 (en) * | 2015-12-02 | 2017-06-08 | Rotam Agrochem International Company Limited | Novel form of mefenpyr-diethyl, a process for its preparation and use of the same |
| CN110003107A (en) * | 2019-04-28 | 2019-07-12 | 东华大学 | A kind of synthetic method of mefenpyrdiethyl |
| CN111592493A (en) * | 2020-05-30 | 2020-08-28 | 上海赫腾精细化工有限公司 | Preparation method of mefenpyr-diethyl |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114989040A (en) * | 2022-07-07 | 2022-09-02 | 南京正荣医药化学有限公司 | Synthetic method of mefenpyr-diethyl intermediate |
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