CN113943233A - Preparation method of environment-friendly fomesafen - Google Patents
Preparation method of environment-friendly fomesafen Download PDFInfo
- Publication number
- CN113943233A CN113943233A CN202010787912.3A CN202010787912A CN113943233A CN 113943233 A CN113943233 A CN 113943233A CN 202010787912 A CN202010787912 A CN 202010787912A CN 113943233 A CN113943233 A CN 113943233A
- Authority
- CN
- China
- Prior art keywords
- fomesafen
- friendly
- environment
- preparation
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/80—Mixtures of different zeolites
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/72—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing iron group metals, noble metals or copper
- B01J29/76—Iron group metals or copper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/72—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing iron group metals, noble metals or copper
- B01J29/76—Iron group metals or copper
- B01J29/763—CHA-type, e.g. Chabazite, LZ-218
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a preparation method of environment-friendly fomesafen, and relates to the field of fomesafen synthesis. 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid, methylsulfonamide and solid phosgene are synthesized under the action of dichloroethane to obtain the fomesafen. By changing an acylating agent and a synthesis process, the problem of environmental pollution caused by the traditional phosphorus oxychloride as the acylating agent is solved, and the safe and environment-friendly synthesis and preparation of fomesafen are realized. In addition, by improving the catalyst, the conversion rate and the reaction speed are improved, and the influence of the color of the metal chloride salt on the product quality is reduced.
Description
Technical Field
The invention relates to the field of fomesafen synthesis, in particular to a synthesis and preparation method of environment-friendly fomesafen.
Background
Fomesafen, namely 5- (2-chloro-alpha, alpha-trifluoro-p-tolyloxy) -N-methylsulfonyl-2-nitrobenzamide, has the effective component content of 95 percent and is an off-white powdery solid. Melting point 218-221 ℃, density: 1.28g/cm3, vapor pressure less than 0.1mpa (50 ℃), is a post-emergence herbicide for soybean and peanut fields with high selectivity, can effectively prevent and kill broad-leaved weeds and cyperus rotundus in the soybean and peanut fields, and can also be used for preventing and killing broad-leaved weeds in orchards and rubber plantation. It also has certain control effect on gramineous weeds. Can be absorbed by the roots and leaves of the weeds, so that the weeds are quickly withered and yellow to die, and the pesticide effect is not influenced after the weeds are sprayed for 4 to 6 hours and is safe to the soybeans. Therefore, the application range is wide and the dosage is large.
The existing method for synthesizing fomesafen uses phosphorus oxychloride as an acylating agent in one-step amination synthesis, the phosphorus oxychloride has high toxicity, and a byproduct pollutes the environment. Phosphorus oxychloride has high toxicity, is easy to decompose water, releases large amount of heat and hydrogen chloride, and has strong corrosivity. When the paint is stored, the sealing is not good, moisture absorption is easy to occur, a large amount of white smoke is generated, and the paint has corrosivity, environmental pollution and potential safety hazard. The phosphorus oxychloride generates phosphoric acid and hydrochloric acid in the synthesis process, which not only has strong corrosivity, but also is difficult to treat, and the phosphorus-containing wastewater is not friendly to the environment. There is therefore a need for a more environmentally friendly synthetic process.
Disclosure of Invention
The invention aims to provide a preparation method of environment-friendly fomesafen, which solves the problem of environmental pollution caused by the traditional phosphorus oxychloride as an acylating agent by changing an acylating agent and a synthesis process, realizes the synthesis preparation of the safe and environment-friendly fomesafen, and simultaneously improves the conversion rate and the reaction speed and reduces the influence of the color of chlorinated metal salt on the product quality by designing a catalyst.
In order to realize the technical effects, the application discloses a preparation method of environment-friendly fomesafen, which is characterized in that 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid, methylsulfonamide and solid phosgene are synthesized under the action of dichloroethane to obtain the fomesafen.
Further comprises the following steps:
(1) feeding materials for reaction, namely dispersing 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid by using dichloroethane as a solvent, adding methylsulfonamide after the dichloroethane is qualified with water, then adding solid phosgene at a constant speed, and keeping the temperature below 90 ℃ for reaction for 1-2 hours after the solid phosgene is added;
(2) carrying out synthesis reaction, heating to 90-120 ℃, continuing to react, adding seed crystal after a period of time, and continuing to keep the temperature for 10-12 hours to complete the synthesis;
(3) and (3) separating crystals, cooling, crystallizing, filtering, washing and drying the crystals to obtain the finished fomesafen.
In a further synthesis reaction step a zeolite supporting a chlorinated metal salt is used as catalyst.
Further the chloride metal salt is selected from one or more of ferric chloride, cupric chloride and zinc chloride.
Further the zeolite loaded with chloride metal salt is prepared by the following steps:
(a) mixing CHA type molecular sieve and AEI type molecular sieve according to the proportion of 1 (1-2), and placing in water to form a mixture;
(b) flattening the mixture, drying, adding a metal chloride salt aqueous solution into the dried mixture, and adjusting to a proper metal chloride salt loading amount;
(c) after the mixture mixed with the chloride metal salt is pressed and formed, the zeolite catalyst loaded with the chloride metal salt is obtained through calcination at 400-600 ℃.
Further, the loading amount of the chlorinated metal salt is 2-4% of the mass of the CHA type molecular sieve and the AEI type molecular sieve.
In the further synthesis reaction step, the temperature is raised to 90-120 ℃, the catalyst is added for continuous reaction, the catalyst is separated after 6-8 hours, and then the seed crystal is added for continuous heat preservation till the total time is 10-12 hours.
The further catalyst is added in an amount of 0.5-4% by weight based on the weight of 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid.
Further, the amount of the methylsulfonamide and the solid phosgene is added in excess relative to the amount of 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid.
Further, the adding molar weight ratio of the 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid, the methylsulfonamide and the solid phosgene is 1 (1-1.2) to 0.34-0.4.
The invention has the beneficial effects that:
solid phosgene is used for replacing phosphorus oxychloride as an acylating agent, so that the method is safe and environment-friendly. The solid phosgene has strong stability, is easy to transport and store, and the raw material is solid and is easy to accurately measure; the reaction condition is mild, high temperature and high pressure do not exist, and the reaction products are carbon dioxide, hydrogen chloride and hydrogen chloride which can be absorbed into hydrochloric acid, so that phosphorus-containing wastewater is not generated, and the acyl chloride agent is harmless to the environment and belongs to an environment-friendly acyl chloride agent.
The zeolite loaded with the metal chloride salt is used as the catalyst, so that the conversion rate and the conversion speed can be improved, and the influence of the color of the traditional metal chloride salt on a finished product is reduced through the loading of the zeolite.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below. It is obvious that the drawings in the following description are some embodiments of the invention, and that for a person skilled in the art, other drawings can be derived from them without inventive effort.
FIG. 1 is a process flow diagram of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention. It is to be understood that the embodiments described are only a few embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The structural formula of the solid phosgene is shown as formula I:
(formula I)
The structural formula of the nitride is shown as formula II:
(formula II)
The reaction principle is as follows:
preparation of chloride metal salt loaded zeolites:
(a) mixing CHA type molecular sieve and AEI type molecular sieve according to the proportion of 1 (1-2), and placing in water to form a mixture;
(b) flattening the mixture, drying, adding a metal chloride salt aqueous solution into the dried mixture, and adjusting to a proper metal chloride salt loading amount;
(c) after the mixture mixed with the chloride metal salt is pressed and formed, the zeolite catalyst loaded with the chloride metal salt is obtained through calcination at 400-600 ℃.
The chlorinated metal salt is copper chloride, and the loading amount is 3% of the mass of the CHA type molecular sieve and the AEI type molecular sieve.
The first embodiment is as follows:
referring to figure 1, the compound 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid is used to synthesize fomesafen with methyl sulfonamide and solid phosgene under the action of dichloroethane. Transferring the extracted 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid dichloroethane to a reaction kettle, adding 383 parts of 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid, adding 114 parts of methylsulfonamide after the dichloroethane is qualified with water, adding 118 parts of solid phosgene at a constant speed, keeping the temperature below 90 ℃, keeping the temperature for 2 hours after the solid phosgene is completely added, adding seed crystals, continuing to perform heat preservation reaction at 120 ℃ for 12 hours, then cooling, adding water, filtering and drying to obtain the fomesafen finished product. The mass fraction of the finished fomesafen is 416 parts.
It can be seen that the ratio of the charge amount of 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid to the charge amount of methylsulfonamide and phosgene solids was about 1:1.2:0.4, and the yield of fomesafen relative to 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid was 94.9%. The product is colorless crystals.
Example two:
referring to figure 1, the compound 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid is used to synthesize fomesafen with methyl sulfonamide and solid phosgene under the action of dichloroethane. Transferring the extracted 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid dichloroethane to a reaction kettle, adding 383 parts of 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid, adding 104 parts of methylsulfonamide after the dichloroethane is qualified with water, adding 109 parts of solid phosgene at a constant speed, keeping the temperature below 90 ℃, keeping the temperature for 2 hours after the solid phosgene is added, adding seed crystals, continuing to perform heat preservation reaction at 120 ℃ for 12 hours, then cooling, adding water, filtering and drying to obtain the fomesafen finished product. The mass fraction of the finished fomesafen is 409 portions.
It can be seen that the ratio of the charge amount of 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid to the charge amount of methylsulfonamide and phosgene solids was about 1:1.1:0.37, and the yield of fomesafen relative to 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid was 93.3%. The product is colorless crystals.
Example three:
referring to figure 1, the compound 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid is used to synthesize fomesafen with methyl sulfonamide and solid phosgene under the action of dichloroethane. Transferring the 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid dichloroethane after extraction to a reaction kettle, adding 383 parts of 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid, adding 114 parts of methylsulfonamide after the dichloroethane is qualified with water, adding 118 parts of solid phosgene at a constant speed, keeping the temperature below 90 ℃, keeping the temperature for 2 hours after the solid phosgene is added, adding 8 parts of catalyst for reaction at the temperature of 100 ℃ and 120 ℃ for 8 hours to remove the catalyst, continuing the reaction for 10 hours until the total time, then cooling, adding water, filtering and drying to obtain the fomesafen finished product. The mass fraction of the finished fomesafen is 428 parts.
It can be seen that the charging ratio of 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid to methylsulfonamide and phosgene solids was about 1:1.2:0.4, the amount of catalyst added relative to 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid was 2%, and the yield of fomesafen relative to 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid was 97.7%. The product is colorless crystals.
Example four:
referring to figure 1, the compound 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid is used to synthesize fomesafen with methyl sulfonamide and solid phosgene under the action of dichloroethane. Transferring the 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid dichloroethane after extraction to a reaction kettle, adding 383 parts of 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid, adding 104 parts of methylsulfonamide after the dichloroethane is qualified with water, adding 109 parts of solid phosgene at a constant speed, keeping the temperature below 90 ℃, keeping the temperature for 2 hours after the solid phosgene is added, adding 8 parts of catalyst for reaction at the temperature of 100 ℃ and 120 ℃ for 8 hours to remove the catalyst, continuing the reaction for 10 hours until the total time, then cooling, adding water, filtering and drying to obtain the fomesafen finished product. The mass fraction of the finished fomesafen is weighed to be 420 parts.
It can be seen that the charging ratio of 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid to methylsulfonamide and phosgene solids was about 1:1.1:0.37, the amount of catalyst added relative to 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid was 2%, and the yield of fomesafen relative to 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid was 95.8%. The product is colorless crystals.
Comparative example one:
referring to figure 1, the compound 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid is used to synthesize fomesafen with methyl sulfonamide and solid phosgene under the action of dichloroethane. Transferring the extracted 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid dichloroethane to a reaction kettle, adding 383 parts of 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid, adding 114 parts of methylsulfonamide after the dichloroethane is qualified with water, adding 118 parts of solid phosgene at a constant speed, keeping the temperature below 90 ℃, keeping the temperature for 2 hours after the solid phosgene is added, adding 0.24 part of copper chloride for reaction at the temperature of 100 ℃ and 120 ℃ until the total time is 10 hours, then cooling, adding water, filtering and drying to obtain the fomesafen finished product. The mass fraction of the finished fomesafen is 426 parts by weight.
It can be seen that the charge ratio of 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid to methylsulfonamide and phosgene solids was about 1:1.2:0.4, the amount of copper chloride added was 2% in terms of catalyst relative to 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid, and the yield of fomesafen relative to 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid was 97.2%. The product appeared slightly blue.
The synthesis preparation method of the environment-friendly fomesafen disclosed by the invention uses the solid phosgene to replace phosphorus oxychloride as an acylating agent, so that the method is safe and environment-friendly. The solid phosgene has strong stability, is easy to transport and store, and the raw material is solid and is easy to accurately measure; the reaction condition is mild, high temperature and high pressure do not exist, and the reaction products are carbon dioxide, hydrogen chloride and hydrogen chloride which can be absorbed into hydrochloric acid, so that phosphorus-containing wastewater is not generated, and the acyl chloride agent is harmless to the environment and belongs to an environment-friendly acyl chloride agent.
The zeolite loaded with the metal chloride salt is used as the catalyst, so that the conversion rate and the conversion speed can be improved, and the influence of the color of the traditional metal chloride salt on a finished product is reduced through the loading of the zeolite.
The above-mentioned embodiments are merely illustrative of the preferred embodiments of the present invention, and do not limit the scope of the present invention, and various modifications and improvements of the technical solution of the present invention by those skilled in the art without departing from the spirit of the present invention should fall within the protection scope defined by the claims of the present invention.
Claims (10)
1. A preparation method of environment-friendly fomesafen is characterized by comprising the following steps: 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid, methylsulfonamide and solid phosgene are synthesized under the action of dichloroethane to obtain the fomesafen.
2. The preparation method of the environment-friendly fomesafen according to claim 1, characterized by comprising the following steps:
(1) feeding materials for reaction, namely dispersing 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid by using dichloroethane as a solvent, adding methylsulfonamide after the dichloroethane is qualified with water, then adding solid phosgene at a constant speed, and keeping the temperature below 90 ℃ for reaction for 1-2 hours after the solid phosgene is added;
(2) carrying out synthesis reaction, heating to 90-120 ℃, continuing to react, adding seed crystal after a period of time, and continuing to keep the temperature for 10-12 hours to complete the synthesis;
(3) and (3) separating crystals, cooling, crystallizing, filtering, washing and drying the crystals to obtain the finished fomesafen.
3. The preparation method of the environment-friendly fomesafen according to claim 2, characterized in that: the zeolite carrying a chlorinated metal salt is used as a catalyst in the synthesis reaction step.
4. The preparation method of the environment-friendly fomesafen as claimed in claim 3, characterized in that: the chloride metal salt is selected from one or more of copper chloride and zinc chloride.
5. The preparation method of the environment-friendly fomesafen as claimed in claim 3, characterized in that: the zeolite loaded with the chloride metal salt is prepared by the following steps:
(a) mixing CHA type molecular sieve and AEI type molecular sieve according to the proportion of 1 (1-2), and placing in water to form a mixture;
(b) flattening the mixture, drying, adding a metal chloride salt aqueous solution into the dried mixture, and adjusting to a proper metal chloride salt loading amount;
(c) after the mixture mixed with the chloride metal salt is pressed and formed, the zeolite catalyst loaded with the chloride metal salt is obtained through calcination at 400-600 ℃.
6. The method for preparing environment-friendly fomesafen according to claim 5, characterized in that: the loading capacity of the chlorinated metal salt is 2-4% of the mass of the CHA type molecular sieve and the AEI type molecular sieve.
7. The preparation method of the environment-friendly fomesafen as claimed in claim 3, characterized in that: in the step of the synthetic reaction, the temperature is raised to 90-120 ℃, the catalyst is added for continuous reaction, the catalyst is separated after 6-8 hours, and the seed crystal is added for continuous heat preservation until the total time is 10-12 hours.
8. The preparation method of the environment-friendly fomesafen as claimed in claim 3, characterized in that: the addition amount of the catalyst is 0.5-4% of the weight of the 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid.
9. The preparation method of the environment-friendly fomesafen according to claim 1, characterized in that: the amount of the methylsulfonamide and the solid phosgene is excessive relative to the amount of the 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid.
10. The method for preparing environment-friendly fomesafen according to claim 9, characterized in that: the adding molar weight ratio of the 5- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-nitrobenzoic acid, the methyl sulfonamide and the solid phosgene is 1 (1-1.2) to 0.34-0.4.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010787912.3A CN113943233A (en) | 2020-08-07 | 2020-08-07 | Preparation method of environment-friendly fomesafen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010787912.3A CN113943233A (en) | 2020-08-07 | 2020-08-07 | Preparation method of environment-friendly fomesafen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113943233A true CN113943233A (en) | 2022-01-18 |
Family
ID=79326954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010787912.3A Pending CN113943233A (en) | 2020-08-07 | 2020-08-07 | Preparation method of environment-friendly fomesafen |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113943233A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0003416A1 (en) * | 1978-01-19 | 1979-08-08 | Imperial Chemical Industries Plc | Diphenyl ether compounds useful as herbicides; methods of using them, processes for preparing them, and herbicidal compositions containing them |
| EP0668260A1 (en) * | 1994-02-17 | 1995-08-23 | Zeneca Limited | Process for phosgenation in the presence of acetonitrile |
| CN102030655A (en) * | 2010-10-21 | 2011-04-27 | 上虞颖泰精细化工有限公司 | Synthesis method of diphenyl ether derivate, combined production method of oxyfluorfen and acifluorfen and synthesis method of oxyfluorfen |
| CN103387524A (en) * | 2013-07-23 | 2013-11-13 | 山东科源化工有限公司 | Preparation method of fomesafen |
-
2020
- 2020-08-07 CN CN202010787912.3A patent/CN113943233A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0003416A1 (en) * | 1978-01-19 | 1979-08-08 | Imperial Chemical Industries Plc | Diphenyl ether compounds useful as herbicides; methods of using them, processes for preparing them, and herbicidal compositions containing them |
| EP0668260A1 (en) * | 1994-02-17 | 1995-08-23 | Zeneca Limited | Process for phosgenation in the presence of acetonitrile |
| CN102030655A (en) * | 2010-10-21 | 2011-04-27 | 上虞颖泰精细化工有限公司 | Synthesis method of diphenyl ether derivate, combined production method of oxyfluorfen and acifluorfen and synthesis method of oxyfluorfen |
| CN103387524A (en) * | 2013-07-23 | 2013-11-13 | 山东科源化工有限公司 | Preparation method of fomesafen |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH618682A5 (en) | ||
| CN113943233A (en) | Preparation method of environment-friendly fomesafen | |
| US5744424A (en) | Plant growth promoter composition comprising N-6-benzyladenine, an alcohol, and a metal hydroxide | |
| US2931716A (en) | Method for handling liquid materials and for granulating and conditioning solids | |
| KR20210028670A (en) | Method for producing a high purity salt of cis-cyclohexane-1,2-dicarboxylic acid | |
| US3050439A (en) | Stable anhydrous disodium ethylene bisdithiocarbamate | |
| WO2009125435A2 (en) | Improved sulfur formulation suitable for organic agriculture | |
| JPH0515672B2 (en) | ||
| CN106259324B (en) | Glyphosate dimethylamine salt water-soluble granule and preparation method thereof | |
| KR100510084B1 (en) | watersoluble Calcium complex and manufacturing method thereof | |
| US3251875A (en) | N-nitroso derivatives | |
| JP2015525727A (en) | Continuous process for producing free-flowing solid acidic P / K fertilizer | |
| ITMI20012269A1 (en) | PROCESS OF PRODUCTION OF A BORON SALT AND ITS USE IN AGRICULTURAL FIELD | |
| IL37390A (en) | Imidazolyl-alkyl-thiophosphates and thiophosphonates,their manufacture and their use as pesticides | |
| JPH09227258A (en) | Production of molded fertilizer and molded fertilizer | |
| CA1135272A (en) | Maufacture of sodium hydrogen divalproate | |
| CN104291308A (en) | Production method for preparing tricalcium phosphate and coproducing special fertilizer for rye | |
| CN104413055A (en) | Preparation method of propaphos | |
| CN105949237A (en) | Preparation method for glyphosate dimethylamine salt active compound | |
| CN104413013A (en) | Preparation method of pyridaben | |
| CN112521211A (en) | High-tower pesticide-fertilizer containing dinotefuran and monosultap and application thereof | |
| CN107473953A (en) | A kind of method for melting the D of separating-purifying 2,4 acid | |
| CN108112580A (en) | A kind of all you and atrazine microemulsion | |
| DE2540127A1 (en) | SCHAEDLING INHIBITOR | |
| JPS57188551A (en) | N-(p-chloro-alpha-methylbenzyl)-alpha-bromo-tert-pentylacetamide, its preparation, and agricultural and horticultural fungicide containing said compound as active component |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |