CN108864181B - Method for synthesizing O, O-dimethyl phosphorodithioate - Google Patents
Method for synthesizing O, O-dimethyl phosphorodithioate Download PDFInfo
- Publication number
- CN108864181B CN108864181B CN201810836759.1A CN201810836759A CN108864181B CN 108864181 B CN108864181 B CN 108864181B CN 201810836759 A CN201810836759 A CN 201810836759A CN 108864181 B CN108864181 B CN 108864181B
- Authority
- CN
- China
- Prior art keywords
- reaction
- catalyst
- synthesizing
- dimethyl phosphorodithioate
- methanol
- 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.)
- Active
Links
- CZGGKXNYNPJFAX-UHFFFAOYSA-N Dimethyldithiophosphate Chemical compound COP(S)(=S)OC CZGGKXNYNPJFAX-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 23
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 83
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 14
- 239000007788 liquid Substances 0.000 claims description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 16
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 13
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 12
- 239000012452 mother liquor Substances 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 238000004321 preservation Methods 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 238000010009 beating Methods 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 16
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000243 solution Substances 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 239000010413 mother solution Substances 0.000 abstract description 2
- 238000012216 screening Methods 0.000 abstract description 2
- 238000010189 synthetic method Methods 0.000 abstract description 2
- 239000007789 gas Substances 0.000 description 8
- 239000000376 reactant Substances 0.000 description 6
- 238000004537 pulping Methods 0.000 description 5
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000005086 pumping Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000005949 Malathion Substances 0.000 description 2
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 2
- 229960000453 malathion Drugs 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- NXQDBZGWYSEGFL-UHFFFAOYSA-N Anilofos Chemical compound COP(=S)(OC)SCC(=O)N(C(C)C)C1=CC=C(Cl)C=C1 NXQDBZGWYSEGFL-UHFFFAOYSA-N 0.000 description 1
- 239000005947 Dimethoate Substances 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- 239000005921 Phosmet Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- NBAUXRCSDWYKRP-UHFFFAOYSA-N dimethyl phosphorochloridothioate Chemical compound COP(Cl)(=O)SC NBAUXRCSDWYKRP-UHFFFAOYSA-N 0.000 description 1
- WWJJVKAEQGGYHJ-UHFFFAOYSA-N dimethyl thiophosphate Chemical compound COP(O)(=S)OC WWJJVKAEQGGYHJ-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003987 organophosphate pesticide Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Classifications
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/17—Esters of thiophosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
Abstract
The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthetic method of O, O-dimethyl phosphorodithioate. The method for synthesizing the O, O-dimethyl phosphorodithioate further improves the content and the yield of a target product by further screening a proper catalyst and adding the catalyst into a methanol solution and dropwise adding the catalyst into a sulfide mother solution on the basis of the method in the prior art; meanwhile, the whole process of dripping methanol is carried out under the condition of micro negative pressure, so that the step of dripping methanol for reaction can be carried out under the condition of lower temperature of 25-35 ℃, and the reaction product hydrogen sulfide can be favorably escaped under the condition of 30-50mmHg micro negative pressure, and the forward progress of the reaction is effectively promoted.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthetic method of O, O-dimethyl phosphorodithioate.
Background
O, O-dimethyl phosphorodithioate, methyl sulfide for short, is an important organophosphorus pesticide intermediate, and can be directly used for synthesizing organophosphorus pesticides such as dimethoate, malathion, phosmet, phenthoate, herbicide anilofos, bactericide, germicide, etc. The O, O-dimethyl phosphorodithioate can also obtain another important organophosphorus intermediate, namely O, O-dimethyl thiophosphoryl chloride, through chlorination reaction.
The method for producing O, O-dimethyl thiophosphate in the prior art is mainly prepared by esterification reaction of phosphorus pentasulfide and methanol, namely, a certain amount of sulfide mother liquor, phosphorus pentasulfide and a catalyst are added into a reaction tank, methanol is dripped under the stirring condition at the temperature of 40-45 ℃, the stirring reaction is continued at the temperature of 50-55 ℃ after the dripping is finished, and the finished product is obtained after cooling and discharging, wherein the yield of the product is about 75% in the general case. However, in this method, on the one hand, the dropping temperature of methanol is high, and on the other hand, pyridine or tetramethylammonium chloride is often used as a catalyst in the process, and this catalyst is not high in yield of the product and tends to cause a large amount of impurities in the synthesis reaction of malathion at the later stage. Therefore, the development of a method for synthesizing O, O-dimethyl phosphorodithioate with higher product yield has positive significance.
Disclosure of Invention
Therefore, the technical problem to be solved by the invention is to provide a method for synthesizing O, O-dimethyl phosphorodithioate, so as to solve the problem of low product yield of the O, O-dimethyl phosphorodithioate synthesis method in the prior art.
In order to solve the technical problems, the method for synthesizing the O, O-dimethyl phosphorodithioate comprises the following steps:
(1) adding phosphorus pentasulfide in the presence of methyl sulfide mother liquor, and fully stirring to obtain reaction feed liquid A;
(2) adding a catalyst into the methanol solution, and uniformly mixing to obtain reaction feed liquid B;
(3) dropwise adding the reaction material liquid B obtained in the step (2) into the reaction material liquid A obtained in the step (1) under a micro-negative pressure condition; and after the dropwise addition is finished, carrying out heat preservation reaction to obtain the required O, O-dimethyl phosphorodithioate.
In the step (2), the catalyst is a mixture of pyridine and 4-dimethylaminopyridine.
In the catalyst, the mass ratio of the pyridine to the 4-dimethylaminopyridine is 1: 0.5-1.5.
The mass ratio of the catalyst to the phosphorus pentasulfide is 1-2.5: 1000.
the molar ratio of the phosphorus pentasulfide to the methanol is 1: 4.02-4.05.
In the step (3), the step of dropwise adding the reaction material liquid B is started when the reaction material liquid A is heated to 25-35 ℃.
In the step (3), the temperature of the heat preservation reaction step is 50-55 ℃.
The micro negative pressure is controlled at the vacuum degree of 30-50 mmHg.
And (3) extracting hydrogen sulfide generated by the reaction and absorbing the hydrogen sulfide by alkali liquor.
The step (1) further comprises the step of carrying out pulping treatment on the reaction feed liquid A.
The method for synthesizing the O, O-dimethyl phosphorodithioate further improves the content and the yield of a target product by further screening a proper catalyst and adding the catalyst into a methanol solution and dropwise adding the catalyst into a sulfide mother solution on the basis of the method in the prior art; meanwhile, the whole process of dripping methanol is carried out under the condition of micro negative pressure, so that the step of dripping methanol for reaction can be carried out under the condition of lower temperature of 25-35 ℃, and the reaction product hydrogen sulfide can be favorably escaped under the condition of 30-50mmHg micro negative pressure, and the forward progress of the reaction is effectively promoted. The method for synthesizing the O, O-dimethyl phosphorodithioate has the advantages that the product content is 96-98%, the product yield is 96-97%, and the problems of low product synthesis content and low yield in the prior art are effectively solved.
Detailed Description
Example 1
The method for synthesizing O, O-dimethyl phosphorodithioate described in this example includes the following steps:
(1) adding 1500kg of methyl sulfide mother liquor into a reaction kettle, adding 1000kg of phosphorus pentasulfide into the reaction kettle, fully stirring for 0.5h, and pulping for 1h to enable the phosphorus pentasulfide and the methyl sulfide mother liquor to be in a slurry state to obtain reaction feed liquid A;
(2) mixing 0.5kg of DMAP and 0.5kg of pyridine as a catalyst, adding the mixture into 580kg of methanol, and uniformly mixing to obtain reaction feed liquid B;
(3) controlling the pressure condition of the reaction kettle to be 30mmHg vacuum degree, heating the reaction feed liquid A in the reaction kettle to 25 ℃, and beginning to dropwise add the reaction feed liquid B into the reaction kettle; and after the dropwise addition is finished, heating the reaction kettle to 50 ℃ for heat preservation reaction for 1h, continuously pumping hydrogen sulfide gas generated by the reaction in the reaction process by using a micro negative pressure state, absorbing the hydrogen sulfide gas by using alkali liquor, and obtaining the required O, O-dimethyl phosphorodithioate after the reaction is finished.
The calculated content of O, O-dimethyl phosphorodithioate in the reactant is 96.5%, and the calculated product yield is 96.3%.
Example 2
The method for synthesizing O, O-dimethyl phosphorodithioate described in this example includes the following steps:
(1) adding 1500kg of methyl sulfide mother liquor into a reaction kettle, adding 1000kg of phosphorus pentasulfide into the reaction kettle, fully stirring for 0.5h, and pulping for 1h to enable the phosphorus pentasulfide and the methyl sulfide mother liquor to be in a slurry state to obtain reaction feed liquid A;
(2) mixing 1.5kg of DMAP and 1kg of pyridine as a catalyst, adding the mixture into 584kg of methanol, and uniformly mixing to obtain reaction feed liquid B;
(3) controlling the pressure condition of the reaction kettle to be 30mmHg vacuum degree, heating the reaction material liquid A in the reaction kettle to 30 ℃, and beginning to dropwise add the reaction material liquid B into the reaction kettle; and after the dropwise addition is finished, heating the reaction kettle to 55 ℃ for heat preservation reaction for 1h, continuously pumping hydrogen sulfide gas generated by the reaction in the reaction process by using a micro negative pressure state, absorbing the hydrogen sulfide gas by using alkali liquor, and obtaining the required O, O-dimethyl phosphorodithioate after the reaction is finished.
The calculated content of O, O-dimethyl phosphorodithioate in the reactant is 96.6%, and the calculated product yield is 96.4%.
Example 3
The method for synthesizing O, O-dimethyl phosphorodithioate described in this example includes the following steps:
(1) adding 1500kg of methyl sulfide mother liquor into a reaction kettle, adding 1000kg of phosphorus pentasulfide into the reaction kettle, fully stirring for 0.5h, and pulping for 1h to enable the phosphorus pentasulfide and the methyl sulfide mother liquor to be in a slurry state to obtain reaction feed liquid A;
(2) mixing 0.8kg of DMAP and 1kg of pyridine as a catalyst, adding the mixture into 581kg of methanol, and uniformly mixing to obtain reaction feed liquid B;
(3) controlling the pressure condition of the reaction kettle to be 40mmHg vacuum degree, heating the reaction material liquid A in the reaction kettle to 35 ℃, and beginning to dropwise add the reaction material liquid B into the reaction kettle; and after the dropwise addition is finished, heating the reaction kettle to 55 ℃ for heat preservation reaction for 1h, continuously pumping hydrogen sulfide gas generated by the reaction in the reaction process by using a micro negative pressure state, absorbing the hydrogen sulfide gas by using alkali liquor, and obtaining the required O, O-dimethyl phosphorodithioate after the reaction is finished.
The calculated content of O, O-dimethyl phosphorodithioate in the reactant is 97.5%, and the calculated product yield is 96.6%.
Example 4
The method for synthesizing O, O-dimethyl phosphorodithioate described in this example includes the following steps:
(1) adding 1500kg of methyl sulfide mother liquor into a reaction kettle, adding 1000kg of phosphorus pentasulfide into the reaction kettle, fully stirring for 0.5h, and pulping for 1h to enable the phosphorus pentasulfide and the methyl sulfide mother liquor to be in a slurry state to obtain reaction feed liquid A;
(2) mixing 1kg of DMAP and 1kg of pyridine as a catalyst, adding the catalyst into 582kg of methanol, and uniformly mixing to obtain reaction feed liquid B;
(3) controlling the pressure condition of the reaction kettle to be 40mmHg vacuum degree, heating the reaction material liquid A in the reaction kettle to 25 ℃, and beginning to dropwise add the reaction material liquid B into the reaction kettle; and after the dropwise addition is finished, heating the reaction kettle to 55 ℃ for heat preservation reaction for 1h, continuously pumping hydrogen sulfide gas generated by the reaction in the reaction process by using a micro negative pressure state, absorbing the hydrogen sulfide gas by using alkali liquor, and obtaining the required O, O-dimethyl phosphorodithioate after the reaction is finished.
The calculated content of O, O-dimethyl phosphorodithioate in the reactant is 98%, and the calculated product yield is 97%.
Comparative example 1
The method for synthesizing O, O-dimethyl phosphorodithioate in the comparative example is the same as that in example 4, except that the catalyst is directly added into the methyl sulfide mother liquor in the step (1) to prepare the reaction feed liquid A, and only a corresponding amount of methanol is directly added dropwise in the step (3).
The calculated content of O, O-dimethyl phosphorodithioate in the reactant is 91.1%, and the calculated product yield is 91.9%.
Comparative example 2
The method for synthesizing O, O-dimethyl phosphorodithioate in this comparative example is the same as example 4 except that in the step (3), the dropping step and the incubation reaction are both performed at normal temperature.
The calculated content of O, O-dimethyl phosphorodithioate in the reactant is 93.3%, and the calculated product yield is 93.8%.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (3)
1. A method for synthesizing O, O-dimethyl phosphorodithioate is characterized by comprising the following steps:
(1) adding phosphorus pentasulfide in the presence of methyl sulfide mother liquor, and fully stirring to obtain reaction feed liquid A;
(2) adding a catalyst into the methanol solution, and uniformly mixing to obtain reaction feed liquid B; the catalyst is a mixture of pyridine and 4-dimethylaminopyridine;
(3) heating the reaction material liquid A to 25-35 ℃, and dropwise adding the reaction material liquid B obtained in the step (2) into the reaction material liquid A obtained in the step (1) under the condition of micro negative pressure; after the dropwise addition is finished, carrying out heat preservation reaction to obtain the required O, O-dimethyl phosphorodithioate; in the catalyst, the mass ratio of the pyridine to the 4-dimethylaminopyridine is 1: 0.5-1.5; the mass ratio of the catalyst to the phosphorus pentasulfide is 1-2.5: 1000, parts by weight; the molar ratio of the phosphorus pentasulfide to the methanol is 1: 4.02-4.05; in the step (3), the temperature of the heat preservation reaction step is 50-55 ℃; the micro negative pressure is controlled at the vacuum degree of 30-50 mmHg.
2. The method for synthesizing O, O-dimethyldithiophosphate according to claim 1, wherein the step (3) further comprises a step of extracting hydrogen sulfide produced by the reaction and absorbing the hydrogen sulfide with an alkali solution.
3. The method for synthesizing O, O-dimethyldithiophosphate according to claim 1 or 2, characterized in that step (1) further comprises a step of subjecting the reaction feed liquid A to a beating treatment.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810836759.1A CN108864181B (en) | 2018-07-26 | 2018-07-26 | Method for synthesizing O, O-dimethyl phosphorodithioate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810836759.1A CN108864181B (en) | 2018-07-26 | 2018-07-26 | Method for synthesizing O, O-dimethyl phosphorodithioate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108864181A CN108864181A (en) | 2018-11-23 |
| CN108864181B true CN108864181B (en) | 2021-04-13 |
Family
ID=64305870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810836759.1A Active CN108864181B (en) | 2018-07-26 | 2018-07-26 | Method for synthesizing O, O-dimethyl phosphorodithioate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108864181B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111440211B (en) * | 2020-04-28 | 2023-02-07 | 宁波大学科学技术学院 | Method for catalytically synthesizing malathion by one-pot method |
| CN116874524B (en) * | 2023-06-12 | 2024-05-10 | 河南嘉颖生物科技有限公司 | Continuous production process and device for high-purity O, O-dialkyl thiophosphate |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5625192A (en) * | 1979-08-09 | 1981-03-10 | Nippon Chem Ind Co Ltd:The | Purification of o,o-dialkyl dithiophosphate |
| CN1702073A (en) * | 2004-05-24 | 2005-11-30 | 姚文刚 | Process for synthesizing O,O'-alkyl thiophosphoric acid |
| CN101293897A (en) * | 2008-06-06 | 2008-10-29 | 武汉工程大学 | Method for preparing O,O-ethyl thioether substituted phosphorus oxychloride |
| WO2009007998A1 (en) * | 2007-07-09 | 2009-01-15 | Suven Life Sciences Limited | Process for the preparation of malathion and its intermediate |
| CN101538282A (en) * | 2009-04-09 | 2009-09-23 | 湖北仙隆化工股份有限公司 | Preparation method of imidan |
| CN102584892A (en) * | 2011-12-27 | 2012-07-18 | 湖北仙隆化工股份有限公司 | Method for preparing O, O-diethyl chlorothiophosphate |
| CN106083921A (en) * | 2016-06-29 | 2016-11-09 | 江苏新农化工有限公司 | One prepares the method for O, O diethyl sulfo-phosphoryl chloride |
| CN107312032A (en) * | 2017-08-09 | 2017-11-03 | 重庆华歌生物化学有限公司 | O, O diethyl sulfo-phosphoryl chloride and preparation method thereof |
| CN107955034A (en) * | 2017-10-25 | 2018-04-24 | 江苏腾龙生物药业有限公司 | A kind of preparation process of Rogor active compound |
-
2018
- 2018-07-26 CN CN201810836759.1A patent/CN108864181B/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5625192A (en) * | 1979-08-09 | 1981-03-10 | Nippon Chem Ind Co Ltd:The | Purification of o,o-dialkyl dithiophosphate |
| CN1702073A (en) * | 2004-05-24 | 2005-11-30 | 姚文刚 | Process for synthesizing O,O'-alkyl thiophosphoric acid |
| WO2009007998A1 (en) * | 2007-07-09 | 2009-01-15 | Suven Life Sciences Limited | Process for the preparation of malathion and its intermediate |
| CN101293897A (en) * | 2008-06-06 | 2008-10-29 | 武汉工程大学 | Method for preparing O,O-ethyl thioether substituted phosphorus oxychloride |
| CN101538282A (en) * | 2009-04-09 | 2009-09-23 | 湖北仙隆化工股份有限公司 | Preparation method of imidan |
| CN102584892A (en) * | 2011-12-27 | 2012-07-18 | 湖北仙隆化工股份有限公司 | Method for preparing O, O-diethyl chlorothiophosphate |
| CN106083921A (en) * | 2016-06-29 | 2016-11-09 | 江苏新农化工有限公司 | One prepares the method for O, O diethyl sulfo-phosphoryl chloride |
| CN107312032A (en) * | 2017-08-09 | 2017-11-03 | 重庆华歌生物化学有限公司 | O, O diethyl sulfo-phosphoryl chloride and preparation method thereof |
| CN107955034A (en) * | 2017-10-25 | 2018-04-24 | 江苏腾龙生物药业有限公司 | A kind of preparation process of Rogor active compound |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108864181A (en) | 2018-11-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108864181B (en) | Method for synthesizing O, O-dimethyl phosphorodithioate | |
| CA3106821C (en) | Process for preparation of o, o-dimethyl phosphoramidothioate and n-(methoxy-methylsulfanylphosphoryl) acetamide | |
| CN102887919A (en) | Production method of triphenylphosphine | |
| CN108558941B (en) | Method for preparing 2-chloroethyl phosphoric acid di (2-chloroethyl) ester through rearrangement reaction | |
| CN104804034A (en) | Preparation method of butyltin tris(2-ethylhexanoate) catalyst | |
| KR20180048661A (en) | Process for producing phosphorus-containing cyanohydrin esters | |
| CN113004325A (en) | Method for tubular continuous synthesis of (3-acetoxy-3-cyanopropyl) -methyl alkyl phosphinate | |
| KR20180045012A (en) | Process for producing phosphorus-containing cyanohydrin esters | |
| CN115260231A (en) | Method for continuously producing O, O-dimethyl phosphorodithioate | |
| CN101195640B (en) | Method for continuous production of 0,0-dimethyl thiophosphoryl chloride | |
| CN101372497A (en) | Preparation of O,O-diethyl-O-(3,5,6- trichloro-2-pyridinyl)thiophosphate | |
| US3897523A (en) | Continuous process for producing dialkyl phosphorochloridothionates | |
| TW201722975A (en) | Process for producing phosphorus-containing cyanohydrin esters | |
| CN106916068B (en) | Simple and convenient benzalkonium chloride production method | |
| CN112159428B (en) | System and method for continuously producing diethyl methylphosphonite | |
| WO2022180555A1 (en) | A process for production of acephate | |
| US6127566A (en) | Process for the synthesis of O,O-dimethyl phosphoroamidothioate | |
| US2851476A (en) | Process of making phosphates | |
| CN111362904A (en) | Preparation method of imidacloprid | |
| KR20190129416A (en) | A synthesis method of gliflozin using continuous process | |
| CN112707933A (en) | Preparation method of N-N-propyl thiophosphoryl triamide suitable for industrial production | |
| CN104402927B (en) | A kind of take 4 chloro pyridine as the method for raw material one pot process Chlorpyrifos 94 and the composite catalyst of use | |
| CN103708433A (en) | Preparation method for phosphorous acid | |
| CN103121936B (en) | Continuous malic acid synthesizing device and preparation method of malic acid | |
| US2891085A (en) | Process for production of |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |