CN114031637B - Method for continuously hydrolyzing glyphosate - Google Patents

Method for continuously hydrolyzing glyphosate Download PDF

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CN114031637B
CN114031637B CN202111308664.0A CN202111308664A CN114031637B CN 114031637 B CN114031637 B CN 114031637B CN 202111308664 A CN202111308664 A CN 202111308664A CN 114031637 B CN114031637 B CN 114031637B
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glyphosate
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CN114031637A (en
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陈建平
董乃胜
陈祥斌
鲍锡莲
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Anhui Dongzhi Guangxin Agrochemical Co Ltd
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Anhui Dongzhi Guangxin Agrochemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
    • C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0215—Sulfur-containing compounds
    • B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0272—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255
    • B01J31/0274—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255 containing silicon
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0272—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255
    • B01J31/0275—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255 also containing elements or functional groups covered by B01J31/0201 - B01J31/0269
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention relates to a method for continuously hydrolyzing glyphosate, which belongs to the technical field of pesticide preparation and comprises the following steps: firstly, sequentially adding methanol, paraformaldehyde and triethylamine into a condensation kettle, heating to 35-50 ℃, and cooling after the reaction liquid is clarified; adding glycine, heating to 50-60 ℃, and cooling after the reaction liquid is clarified; adding dimethyl phosphite, heating to 45-55 ℃, and cooling after the reaction liquid is clarified to obtain condensation liquid; and secondly, adding an acid catalyst into the obtained condensation liquid at the temperature of 20-25 ℃ to react at the temperature of 40-50 ℃. According to the invention, the modified carrier is used as a raw material, and p-toluenesulfonic acid is loaded to prepare the acidic catalyst, so that the generation of chloride salt is avoided from the source, the alkali consumption is reduced, and the cleanliness of the production process is realized. Meanwhile, the process flow is shortened, and the energy consumption is reduced.

Description

Method for continuously hydrolyzing glyphosate
Technical Field
The invention belongs to the technical field of pesticide preparation, and particularly relates to a method for continuously hydrolyzing glyphosate.
Background
Glyphosate is a non-selective, residue-free, biocidal herbicide, very effective against many years of rooting weeds, widely used in rubber, mulberry, tea, orchards and sugarcane fields. Mainly inhibit enolpyruvylshikimin phosphate synthase in plants, thereby inhibiting the conversion of shikimin into phenylalanine, tyrosine and tryptophan, and interfering protein synthesis, leading to death of plants. Glyphosate is combined with metal ions such as iron, aluminum and the like to lose activity, and has no adverse effect on hidden seeds in soil and soil microorganisms.
The glyphosate is mainly prepared from raw materials such as dimethyl phosphite, methanol, hydrochloric acid and the like through the reaction processes of depolymerization, condensation, esterification, acidolysis and the like. However, the process end mother liquor wastewater contains a large amount of Cl -、Na+、PO4 -4 plasma, wherein Cl - is from the hydrochloric acid hydrolysis process in the glyphosate production process; na + is generated in the process of adding alkali into filtrate for neutralization; PO 3 -4 is a major side reaction product from glyphosate production. Cl - has the characteristics of small ionic radius and strong penetrability, and is easy to be adsorbed on a passivation film to form soluble chloride to corrode metal equipment.
Disclosure of Invention
In order to solve the technical problems in the background art, the invention provides a method for continuously hydrolyzing glyphosate.
The aim of the invention can be achieved by the following technical scheme:
A process for the continuous hydrolysis of glyphosate comprising the steps of:
first step, condensation: sequentially adding methanol, paraformaldehyde and triethylamine into a condensation kettle, heating to 35-50 ℃, and cooling to 30-40 ℃ after the reaction liquid is clarified; adding glycine, heating to 50-60 ℃, and cooling to 35-40 ℃ after the reaction liquid is clarified; adding dimethyl phosphite, heating to 45-55 ℃, cooling to 30-45 ℃ after the reaction liquid is clarified, and obtaining condensation liquid;
second, hydrolysis: adding an acid catalyst into the obtained condensation liquid at the temperature of 20-25 ℃, then heating to 40-50 ℃, reacting for 7 hours, and after the reaction is finished, filtering, crystallizing, suction filtering, washing and drying to obtain the glyphosate raw material.
Further, the dosage ratio of methanol, paraformaldehyde, triethylamine, glycine and dimethyl phosphite is 20mL:1.5g:2.5g:2-3g:3.5g; the dosage mass ratio of the acid catalyst to the glycine is 1:2-3.
Further, the acidic catalyst is prepared by the steps of:
Adding p-toluenesulfonic acid into deionized water at 80 ℃, then adding a modified carrier, stirring for 20-24h, evaporating the solvent after stirring, and then drying for 2h at 120 ℃ to obtain an acidic catalyst; the dosage ratio of the p-toluenesulfonic acid, deionized water and the modified carrier is 5g:100mL:6-7g.
Further, the modified support is prepared by the steps of:
Step S11, mixing diatomite and a sodium hydroxide aqueous solution, stirring and mixing for 1h at the temperature of 25 ℃, and then performing reduced pressure suction filtration, washing with deionized water and drying to obtain a solid a; the step is to activate diatomite;
S12, mixing a solid a with absolute ethyl alcohol, performing ultrasonic dispersion for 3min under the condition of 40kHz to obtain a suspension, adding 3-aminopropyl triethoxysilane into the suspension, adjusting the pH value to 6 by acetic acid, stirring for 24h under the condition of 40 ℃, performing suction filtration after stirring, washing by using ethyl alcohol and deionized water, drying at 40 ℃ to constant weight after washing is finished to obtain a solid b, and introducing amino on the solid a by using a silane coupling agent 3-aminopropyl triethoxysilane;
Step S13, mixing epichlorohydrin, ethylene glycol and boron trifluoride, stirring and reacting for 2 hours at 40 ℃, then adding tri (2-amino ethyl) amine and isopropanol, heating and refluxing for reacting for 4 hours, and concentrating under reduced pressure to remove a solvent after the reaction is finished to obtain an intermediate 1;
The reaction process is as follows:
Step S14, mixing the intermediate 1, tetrahydrofuran and triethylamine, adding phosphorus oxychloride at 20 ℃, stirring and reacting for 5 hours, then adding the solid b, keeping the temperature unchanged, and continuing stirring and reacting for 5 hours to obtain the modified carrier. Introducing amino groups on the surface of diatomite to obtain a solid b; the intermediate 1 reacts with phosphorus oxychloride and then reacts with the solid b to obtain the modified carrier containing the phosphate surfactant structure.
Further, the concentration of the aqueous sodium hydroxide solution in step S11 was 0.5mol/L, and the ratio of the amount of diatomaceous earth to the aqueous sodium hydroxide solution was 1g:25mL;
In the step S12, the dosage ratio of the solid a, the 3-aminopropyl triethoxysilane and the absolute ethyl alcohol is 1g:0.6g:20mL;
The ratio of epichlorohydrin, ethylene glycol, tris (2-aminoethyl) amine, isopropyl alcohol and boron trifluoride in the amount of 0.1mol in step S13: 0.1mol:0.1mol:100mL:0.5g;
The dosage ratio of intermediate 1, phosphorus oxychloride, tetrahydrofuran, solid b and triethylamine in step S14 was 2.5g:3g:50mL:5g:1g.
The invention has the beneficial effects that:
According to the invention, the modified carrier is used as a raw material, and p-toluenesulfonic acid is loaded to prepare the acidic catalyst, so that the generation of chloride salt is avoided from the source, the alkali consumption is reduced, and the cleanliness of the production process is realized. Meanwhile, the process flow is shortened, and the energy consumption is reduced.
The acid catalyst contains the obtained surfactant structure containing phosphate, the reaction condition is milder, the generation of side reaction is reduced, the side reaction is inhibited, and the yield is improved under the condition that other processes for synthesizing glyphosate are the same. The phosphate group has excellent alkali resistance and good biodegradability, and the generated wastewater is easy to treat, so that the cost is greatly reduced. The acid catalyst obtained after the loading is easier to recycle, and the continuity of the hydrolysis process is ensured.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
Preparing a modified carrier:
Step S11, mixing diatomite and a sodium hydroxide aqueous solution, stirring and mixing for 1h at the temperature of 25 ℃, and then performing reduced pressure suction filtration, washing with deionized water and drying to obtain a solid a; wherein the concentration of the sodium hydroxide aqueous solution is 0.5mol/L, and the dosage ratio of the diatomite to the sodium hydroxide aqueous solution is 1g:25mL;
s12, mixing a solid a with absolute ethyl alcohol, performing ultrasonic dispersion for 3min under the condition of 40kHz to obtain a suspension, adding 3-aminopropyl triethoxysilane into the suspension, adjusting the pH value to 6 by acetic acid, stirring for 24h under the condition of 40 ℃, performing suction filtration after stirring, washing by using ethyl alcohol and deionized water, and drying to constant weight at 40 ℃ after washing is finished to obtain a solid b; wherein the dosage ratio of the solid a, the 3-aminopropyl triethoxysilane and the absolute ethyl alcohol is 1g:0.6g:20mL;
Step S13, mixing epichlorohydrin, ethylene glycol and boron trifluoride, stirring and reacting for 2 hours at 40 ℃, then adding tri (2-amino ethyl) amine and isopropanol, heating and refluxing for reacting for 4 hours, and concentrating under reduced pressure to remove a solvent after the reaction is finished to obtain an intermediate 1; wherein, the dosage ratio of the epichlorohydrin, the ethylene glycol, the tri (2-amino ethyl) amine, the isopropanol and the boron trifluoride is 0.1mol:0.1mol:0.1mol:100mL:0.5g;
Step S14, mixing the intermediate 1, tetrahydrofuran and triethylamine, adding phosphorus oxychloride at 20 ℃, stirring and reacting for 5 hours, then adding the solid b, keeping the temperature unchanged, and continuing stirring and reacting for 5 hours to obtain a modified carrier; the dosage ratio of intermediate 1, phosphorus oxychloride, tetrahydrofuran, solid b and triethylamine was 2.5g:3g:50mL:5g:1g. Wherein, the dosage ratio of the intermediate 1, phosphorus oxychloride, tetrahydrofuran, solid b and triethylamine is 2.5g:3g:50mL:5g:1g.
Example 2
Preparation of an acid catalyst:
Adding p-toluenesulfonic acid into deionized water at 80 ℃, then adding a modified carrier, stirring for 20 hours, evaporating the solvent after stirring, and then drying for 2 hours at 120 ℃ to obtain an acidic catalyst; the dosage ratio of the p-toluenesulfonic acid, deionized water and the modified carrier is 5g:100mL:6g; the modified support was prepared as in example 1.
Example 3
Preparation of an acid catalyst:
Adding p-toluenesulfonic acid into deionized water at 80 ℃, then adding a modified carrier, stirring for 24 hours, evaporating the solvent after stirring is finished, and then drying for 2 hours at 120 ℃ to obtain an acidic catalyst; the dosage ratio of the p-toluenesulfonic acid, deionized water and the modified carrier is 5g:100mL:7g; the modified support was prepared as in example 1.
Example 4
A process for the continuous hydrolysis of glyphosate comprising the steps of:
First step, condensation: sequentially adding methanol, paraformaldehyde and triethylamine into a condensation kettle, heating to 35 ℃, and cooling to 30 ℃ after the reaction liquid is clarified; adding glycine, heating to 50 ℃, and cooling to 35 ℃ after the reaction liquid is clarified; adding dimethyl phosphite, heating to 45 ℃, cooling to 30 ℃ after the reaction liquid is clarified, and obtaining condensation liquid;
second, hydrolysis: and (3) adding an acid catalyst into the obtained condensation liquid at the temperature of 20 ℃, heating to 40 ℃, reacting for 7 hours, and filtering, crystallizing, suction filtering, washing and drying after the reaction is finished to obtain the glyphosate raw medicine. The yield of the product was 88.2%.
Wherein, the dosage ratio of the methanol, the paraformaldehyde, the triethylamine, the glycine and the dimethyl phosphite is 20mL:1.5g:2.5g:2g:3.5g; the dosage ratio of the acid catalyst to glycine is 1:2. the acidic catalyst was prepared in example 3.
Example 5
A process for the continuous hydrolysis of glyphosate comprising the steps of:
first step, condensation: sequentially adding methanol, paraformaldehyde and triethylamine into a condensation kettle, heating to 40 ℃, and cooling to 35 ℃ after the reaction liquid is clarified; adding glycine, heating to 55 ℃, and cooling to 35 ℃ after the reaction liquid is clarified; adding dimethyl phosphite, heating to 50 ℃, cooling to 35 ℃ after the reaction liquid is clarified, and obtaining condensation liquid;
Second, hydrolysis: and (3) adding an acid catalyst into the obtained condensation liquid at the temperature of 20 ℃, heating to 45 ℃, reacting for 7 hours, and filtering, crystallizing, suction filtering, washing and drying after the reaction is finished to obtain the glyphosate raw medicine. The yield of the product was 88.5%.
Wherein, the dosage ratio of the methanol, the paraformaldehyde, the triethylamine, the glycine and the dimethyl phosphite is 20mL:1.5g:2.5g:3g:3.5g; the dosage ratio of the acid catalyst to glycine is 1:2. the acidic catalyst was prepared in example 3.
Example 6
A process for the continuous hydrolysis of glyphosate comprising the steps of:
First step, condensation: sequentially adding methanol, paraformaldehyde and triethylamine into a condensation kettle, heating to 50 ℃, and cooling to 40 ℃ after the reaction liquid is clarified; adding glycine, heating to 60 ℃, and cooling to 40 ℃ after the reaction liquid is clarified; adding dimethyl phosphite, heating to 55 ℃, cooling to 45 ℃ after the reaction liquid is clarified, and obtaining condensation liquid;
Second, hydrolysis: and (3) adding an acid catalyst into the obtained condensation liquid at the temperature of 25 ℃, heating to 50 ℃, reacting for 7 hours, and filtering, crystallizing, suction filtering, washing and drying after the reaction is finished to obtain the glyphosate raw medicine. The yield of the product was 88.1%.
Wherein, the dosage ratio of the methanol, the paraformaldehyde, the triethylamine, the glycine and the dimethyl phosphite is 20mL:1.5g:2.5g:3g:3.5g; the dosage ratio of the acid catalyst to glycine is 1:3. the acidic catalyst was prepared in example 3.
Comparative example 1
Adding p-toluenesulfonic acid into deionized water at 80 ℃, then adding diatomite, stirring for 24 hours, evaporating the solvent after stirring, and then drying for 2 hours at 120 ℃ to obtain an acidic catalyst; the dosage ratio of the p-toluenesulfonic acid, deionized water and diatomite is 5g:100mL:7g.
Comparative example 2
The acid catalyst of example 5 was converted to the sample of comparative example 1, and the remaining materials and preparation process were kept unchanged. The yield of the product was 72.5%.
As can be seen from the product yields of examples 4-6 and comparative example 2, the yields were improved when the acid catalyst of the present invention was added, with the other processes of glyphosate synthesis being the same.
In the description of the present specification, the descriptions of the terms "one embodiment," "example," "specific example," and the like, mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the present invention. In this specification, schematic representations of the above terms do not necessarily refer to the same embodiments or examples. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The foregoing is merely illustrative and explanatory of the invention, as various modifications and additions may be made to the particular embodiments described, or in a similar manner, by those skilled in the art, without departing from the scope of the invention or exceeding the scope of the invention as defined in the claims.

Claims (4)

1. A method for continuously hydrolyzing glyphosate, comprising the steps of:
Firstly, sequentially adding methanol, paraformaldehyde and triethylamine into a condensation kettle, heating to 35-50 ℃, and cooling to 30-40 ℃ after the reaction liquid is clarified; adding glycine, heating to 50-60 ℃, and cooling to 35-40 ℃ after the reaction liquid is clarified; adding dimethyl phosphite, heating to 45-55 ℃, cooling to 30-45 ℃ after the reaction liquid is clarified, and obtaining condensation liquid; the dosage ratio of methanol, paraformaldehyde, triethylamine, glycine and dimethyl phosphite is 20mL:1.5g:2.5g:2-3g:3.5g; the dosage mass ratio of the acid catalyst to the glycine is 1:2-3;
Secondly, adding an acid catalyst into the obtained condensation liquid at the temperature of 20-25 ℃, reacting at the temperature of 40-50 ℃, and filtering, crystallizing, suction filtering, washing and drying after the reaction is finished to obtain a glyphosate raw medicine;
The acid catalyst is prepared by the following steps:
step S11, mixing diatomite and a sodium hydroxide aqueous solution, stirring and mixing for 1h at the temperature of 25 ℃, and then performing reduced pressure suction filtration, washing with deionized water and drying to obtain a solid a;
s12, mixing a solid a with absolute ethyl alcohol, performing ultrasonic dispersion for 3min under the condition of 40kHz to obtain a suspension, adding 3-aminopropyl triethoxysilane into the suspension, adjusting the pH value to 6 by acetic acid, stirring for 24h under the condition of 40 ℃, performing suction filtration after stirring, washing by using ethyl alcohol and deionized water, and drying to constant weight at 40 ℃ after washing is finished to obtain a solid b;
Step S13, mixing epichlorohydrin, ethylene glycol and boron trifluoride, stirring and reacting for 2 hours at 40 ℃, then adding tri (2-aminoethyl) amine and isopropanol, and heating and refluxing for reacting for 4 hours to obtain an intermediate 1;
Step S14, mixing the intermediate 1, tetrahydrofuran and triethylamine, adding phosphorus oxychloride at 20 ℃, stirring and reacting for 5 hours, then adding the solid b, keeping the temperature unchanged, and continuing stirring and reacting for 5 hours to obtain a modified carrier; adding p-toluenesulfonic acid into deionized water at 80 ℃, then adding a modified carrier, stirring for 20-24h, and performing post-treatment to obtain the acidic catalyst.
2. A process for the continuous hydrolysis of glyphosate as claimed in claim 1 wherein the reaction time in the second step is 7 hours.
3. The method for continuous hydrolysis of glyphosate as recited in claim 1, wherein the post-treatment during the preparation of the acidic catalyst comprises: after stirring, the solvent was evaporated to dryness and dried at 120℃for 2h.
4. The continuous hydrolysis method of glyphosate as claimed in claim 1, wherein the concentration of the aqueous sodium hydroxide solution in step S11 is 0.5mol/L, and the ratio of diatomite to the aqueous sodium hydroxide solution is 1g:25mL;
In the step S12, the dosage ratio of the solid a, the 3-aminopropyl triethoxysilane and the absolute ethyl alcohol is 1g:0.6g:20mL;
The ratio of epichlorohydrin, ethylene glycol, tris (2-aminoethyl) amine, isopropyl alcohol and boron trifluoride in the amount of 0.1mol in step S13: 0.1mol:0.1mol:100mL:0.5g;
The dosage ratio of intermediate 1, phosphorus oxychloride, tetrahydrofuran, solid b and triethylamine in step S14 was 2.5g:3g:50mL:5g:1g.
CN202111308664.0A 2021-11-05 2021-11-05 Method for continuously hydrolyzing glyphosate Active CN114031637B (en)

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CN101704844A (en) * 2009-04-27 2010-05-12 南通泰禾化工有限公司 Method for preparing glyphosate by alkyl phosphite
CN101875671A (en) * 2009-04-28 2010-11-03 苏州佳辉化工有限公司 Synthesis method of glyphosate
CN103421043A (en) * 2012-10-31 2013-12-04 上海理工大学 Hydrosis process improvement method for synthesizing glyphosate by alkyl ester process
CN103554181A (en) * 2013-11-22 2014-02-05 重庆紫光化工股份有限公司 Method for catalyzed synthesis of N-(phosphonomethyl) iminodiacetic acid by p-toluenesulfonic acid
CN109942626A (en) * 2019-04-19 2019-06-28 山东润博生物科技有限公司 A kind of synthetic method of glyphosate
CN113185548A (en) * 2021-05-10 2021-07-30 浙江新安化工集团股份有限公司 Glyphosate synthesis method for improving utilization rate of dimethyl phosphite

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN2015DN01080A (en) * 2012-07-17 2015-06-26 Straitmark Holding Ag

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101704844A (en) * 2009-04-27 2010-05-12 南通泰禾化工有限公司 Method for preparing glyphosate by alkyl phosphite
CN101875671A (en) * 2009-04-28 2010-11-03 苏州佳辉化工有限公司 Synthesis method of glyphosate
CN103421043A (en) * 2012-10-31 2013-12-04 上海理工大学 Hydrosis process improvement method for synthesizing glyphosate by alkyl ester process
CN103554181A (en) * 2013-11-22 2014-02-05 重庆紫光化工股份有限公司 Method for catalyzed synthesis of N-(phosphonomethyl) iminodiacetic acid by p-toluenesulfonic acid
CN109942626A (en) * 2019-04-19 2019-06-28 山东润博生物科技有限公司 A kind of synthetic method of glyphosate
CN113185548A (en) * 2021-05-10 2021-07-30 浙江新安化工集团股份有限公司 Glyphosate synthesis method for improving utilization rate of dimethyl phosphite

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