CN108864181A - A kind of method of synthesis O, O- dimethyl disulfide substituted phosphate - Google Patents
A kind of method of synthesis O, O- dimethyl disulfide substituted phosphate Download PDFInfo
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- CN108864181A CN108864181A CN201810836759.1A CN201810836759A CN108864181A CN 108864181 A CN108864181 A CN 108864181A CN 201810836759 A CN201810836759 A CN 201810836759A CN 108864181 A CN108864181 A CN 108864181A
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- Prior art keywords
- dimethyl disulfide
- substituted phosphate
- synthesis
- disulfide substituted
- reaction
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- WQOXQRCZOLPYPM-UHFFFAOYSA-N Dimethyl disulfide Natural products CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 229910019142 PO4 Inorganic materials 0.000 title claims abstract description 41
- 239000010452 phosphate Substances 0.000 title claims abstract description 41
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 34
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 22
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 70
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 239000012452 mother liquor Substances 0.000 claims abstract description 14
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims description 31
- 239000000463 material Substances 0.000 claims description 21
- 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
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 12
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 12
- 238000009413 insulation Methods 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 238000005360 mashing Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 16
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract description 3
- 239000007795 chemical reaction product 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 3
- 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
- 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
- 241000894006 Bacteria Species 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
- 238000003556 assay Methods 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
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 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
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 1
- 239000003987 organophosphate pesticide Substances 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
- 238000003756 stirring Methods 0.000 description 1
- 239000006273 synthetic pesticide Substances 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 chemosynthesis technical fields, and in particular to the synthetic method of a kind of O, O- dimethyl disulfide substituted phosphate.Synthesis O of the present invention, the method of O- dimethyl disulfide substituted phosphate, on the basis of art methods, pass through the further screening to appropriate catalysts, and by the way that the mode being added dropwise in sulfide mother liquor into methanol solution is added in the catalyst, the content and yield of target product are further improved；Simultaneously, the step of entire process that methanol is added dropwise all carries out under the conditions of tiny structure, the dropwise addition methanol is reacted carries out under the conditions of 25-35 DEG C of relatively low temperature, and under the conditions of 30-50mmHg tiny structure, the evolution for being conducive to reaction product hydrogen sulfide effectively facilitates reaction forward progress.
Description
Technical field
The invention belongs to chemosynthesis technical fields, and in particular to the synthesis side of a kind of O, O- dimethyl disulfide substituted phosphate
Method.
Background technique
O, O- dimethyl disulfide substituted phosphate, abbreviation methyl sulfide are important organophosphorus pesticide intermediate, can be direct
Synthetic pesticide Rogor, malathion, phosmet, phenthoate dimephenthoate cidial, herbicide anilofos, the organic phosphorus agricultures such as fungicide gram bacterium is strong
Medicine.O, O- dimethyl disulfide substituted phosphate can also obtain another important organic phosphorus intermediate-i.e. O by chlorination reaction,
O- dimethyl thiophosphoryl chloride.
O is produced in the prior art, and the method for O- dimethyl disulfide substituted phosphate is mainly carried out by phosphorus pentasulfide and methanol
Esterification and be made, i.e., by a certain amount of sulfide mother liquor, phosphorus pentasulfide and catalyst be added reactor tank in, in stirring bar
Under part control temperature in 40-45 DEG C of dropwises addition methanol, continue to be stirred to react in 50-55 DEG C after being added dropwise to complete, cooling discharging to obtain the final product at
Product, the yield of product is 75% or so under normal conditions.But in this method, on the one hand, the dropping temperature of methanol is higher, another
Aspect, for technique mostly using pyridine or tetramethyl ammonium chloride as catalyst, the catalyst is not high for the yield of product, and easily leads to
Impurity level is more in the synthetic reaction of later period malathion.Therefore, a kind of higher synthesis O of product yield, O- dimethyl are developed
The method of phosphorodithioate has positive meaning.
Summary of the invention
For this purpose, technical problem to be solved by the present invention lies in a kind of synthesis O is provided, O- dimethyl disulfide substituted phosphate
Method, to solve O in the prior art, the lower problem of O- dimethyl disulfide substituted phosphate synthetic method product yield.
In order to solve the above technical problems, a kind of synthesis O of the present invention, the method for O- dimethyl disulfide substituted phosphate,
Include the following steps：
(1) in the presence of methyl sulfide mother liquor, phosphorus pentasulfide is added, is sufficiently stirred, obtains reaction material liquid A；
(2) it takes catalyst to be added into methanol solution, mixes, obtain reaction material liquid B；
(3) under the conditions of tiny structure, the reaction material liquid B that the step (2) obtains is added dropwise to what the step (1) obtained
In reaction material liquid A；And after being added dropwise to complete, insulation reaction is carried out, required O, O- dimethyl disulfide substituted phosphate are obtained.
In the step (2), the catalyst is the mixture of pyridine and 4-dimethylaminopyridine.
In the catalyst, the mass ratio of the pyridine and 4-dimethylaminopyridine is 1：0.5-1.5.
The mass ratio of the catalyst and the phosphorus pentasulfide is 1-2.5：1000.
The molar ratio of the phosphorus pentasulfide and methanol is 1：4.02-4.05.
In the step (3), the step of dropwise reaction feed liquid B is when the reaction material liquid A is heated to 25-35 DEG C
Start to carry out.
In the step (3), the temperature of the insulation reaction step is 50-55 DEG C.
The tiny structure is control vacuum degree 30-50mmHg.
In the step (3), further include the steps that extracting the hydrogen sulfide that reaction generates out and being absorbed with lye.
In the step (1), further include the steps that carrying out the reaction material liquid A into mashing processing.
The method of synthesis O of the present invention, O- dimethyl disulfide substituted phosphate is led on the basis of art methods
The further screening to appropriate catalysts is crossed, and is added dropwise to sulfide mother liquor into methanol solution by being added the catalyst
In mode, further improve the content and yield of target product；Meanwhile the entire process that methanol is added dropwise is all in tiny structure
Under the conditions of the step of carrying out, the dropwise addition methanol is reacted carried out under the conditions of 25-35 DEG C of relatively low temperature, and 30-
Under the conditions of 50mmHg tiny structure, be conducive to the evolution of reaction product hydrogen sulfide, effectively facilitate reaction forward progress.It is of the present invention
O, the method for O- dimethyl disulfide substituted phosphate are synthesized, product assay 96-98%, product yield 96-97% are effectively improved existing
There is in technical method the problem that synthetic product content is low, yield is low.
Specific embodiment
Embodiment 1
The method of synthesis O described in the present embodiment, O- dimethyl disulfide substituted phosphate, includes the following steps：
(1) 1500kg methyl sulfide mother liquor is added into reaction kettle, then the vulcanization of 1000kg five two is added into reaction kettle
0.5h is sufficiently stirred in phosphorus, and carries out mashing processing 1h, so that phosphorus pentasulfide and methyl sulfide mother liquor is become pulpous state, obtains anti-
Answer feed liquid A；
(2) pyridine of 0.5kg DMAP and 0.5kg is taken to mix as catalyst, addition is mixed into 580kg methanol, obtained
Reaction material liquid B；
(3) pressure condition for controlling the reaction kettle is 30mmHg vacuum degree, and by the reaction material liquid A in reaction kettle
25 DEG C are warming up to, and starts that the reaction material liquid B is added dropwise into reaction kettle；And after being added dropwise to complete, the reaction kettle is heated up
To 50 DEG C of progress insulation reaction 1h, the hydrogen sulfide gas generated in reaction process using the continuous extraction of micro-vacuum state, and
Hydrogen sulfide gas is absorbed with lye, after reaction, obtains required O, O- dimethyl disulfide substituted phosphate.
It is computed, O in reactant, the content 96.5% of O- dimethyl disulfide substituted phosphate, calculating product yield is
96.3%.
Embodiment 2
The method of synthesis O described in the present embodiment, O- dimethyl disulfide substituted phosphate, includes the following steps：
(1) 1500kg methyl sulfide mother liquor is added into reaction kettle, then the vulcanization of 1000kg five two is added into reaction kettle
0.5h is sufficiently stirred in phosphorus, and carries out mashing processing 1h, so that phosphorus pentasulfide and methyl sulfide mother liquor is become pulpous state, obtains anti-
Answer feed liquid A；
(2) pyridine of 1.5kg DMAP and 1kg is taken to mix as catalyst, addition is mixed into 584kg methanol, is obtained anti-
Answer feed liquid B；
(3) pressure condition for controlling the reaction kettle is 30mmHg vacuum degree, and by the reaction material liquid A in reaction kettle
30 DEG C are warming up to, and starts that the reaction material liquid B is added dropwise into reaction kettle；And after being added dropwise to complete, the reaction kettle is heated up
To 55 DEG C of progress insulation reaction 1h, the hydrogen sulfide gas generated in reaction process using the continuous extraction of micro-vacuum state, and
Hydrogen sulfide gas is absorbed with lye, after reaction, obtains required O, O- dimethyl disulfide substituted phosphate.
It is computed, O in reactant, the content 96.6% of O- dimethyl disulfide substituted phosphate, calculating product yield is
96.4%.
Embodiment 3
The method of synthesis O described in the present embodiment, O- dimethyl disulfide substituted phosphate, includes the following steps：
(1) 1500kg methyl sulfide mother liquor is added into reaction kettle, then the vulcanization of 1000kg five two is added into reaction kettle
0.5h is sufficiently stirred in phosphorus, and carries out mashing processing 1h, so that phosphorus pentasulfide and methyl sulfide mother liquor is become pulpous state, obtains anti-
Answer feed liquid A；
(2) pyridine of 0.8kg DMAP and 1kg is taken to mix as catalyst, addition is mixed into 581kg methanol, is obtained anti-
Answer feed liquid B；
(3) pressure condition for controlling the reaction kettle is 40mmHg vacuum degree, and by the reaction material liquid A in reaction kettle
35 DEG C are warming up to, and starts that the reaction material liquid B is added dropwise into reaction kettle；And after being added dropwise to complete, the reaction kettle is heated up
To 55 DEG C of progress insulation reaction 1h, the hydrogen sulfide gas generated in reaction process using the continuous extraction of micro-vacuum state, and
Hydrogen sulfide gas is absorbed with lye, after reaction, obtains required O, O- dimethyl disulfide substituted phosphate.
It is computed, O in reactant, the content 97.5% of O- dimethyl disulfide substituted phosphate, calculating product yield is
96.6%.
Embodiment 4
The method of synthesis O described in the present embodiment, O- dimethyl disulfide substituted phosphate, includes the following steps：
(1) 1500kg methyl sulfide mother liquor is added into reaction kettle, then the vulcanization of 1000kg five two is added into reaction kettle
0.5h is sufficiently stirred in phosphorus, and carries out mashing processing 1h, so that phosphorus pentasulfide and methyl sulfide mother liquor is become pulpous state, obtains anti-
Answer feed liquid A；
(2) pyridine of 1kg DMAP and 1kg is taken to mix as catalyst, addition is mixed into 582kg methanol, reacted
Feed liquid B；
(3) pressure condition for controlling the reaction kettle is 40mmHg vacuum degree, and by the reaction material liquid A in reaction kettle
25 DEG C are warming up to, and starts that the reaction material liquid B is added dropwise into reaction kettle；And after being added dropwise to complete, the reaction kettle is heated up
To 55 DEG C of progress insulation reaction 1h, the hydrogen sulfide gas generated in reaction process using the continuous extraction of micro-vacuum state, and
Hydrogen sulfide gas is absorbed with lye, after reaction, obtains required O, O- dimethyl disulfide substituted phosphate.
It is computed, O in reactant, the content 98% of O- dimethyl disulfide substituted phosphate, calculating product yield is 97%.
Comparative example 1
O is synthesized described in this comparative example, the method for O- dimethyl disulfide substituted phosphate is with embodiment 4, and difference is only that, institute
It states and the reaction material liquid A is made in the methyl sulfide mother liquor that catalyst is directly added into step (1), and in the step (3)
The methanol of corresponding amount is only directly added dropwise.
It is computed, O in reactant, the content 91.1% of O- dimethyl disulfide substituted phosphate, calculating product yield is
91.9%.
Comparative example 2
O is synthesized described in this comparative example, the method for O- dimethyl disulfide substituted phosphate is with embodiment 4, and difference is only that, institute
It states in step (3), a dropping step and insulation reaction carry out under room temperature.
It is computed, O in reactant, the content 93.3% of O- dimethyl disulfide substituted phosphate, calculating product yield is
93.8%.
Obviously, the above embodiments are merely examples for clarifying the description, and does not limit the embodiments.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or
It changes.There is no necessity and possibility to exhaust all the enbodiments.And it is extended from this it is obvious variation or
It changes still within the protection scope of the invention.
Claims (10)
1. a kind of method of synthesis O, O- dimethyl disulfide substituted phosphate, which is characterized in that include the following steps：
(1) in the presence of methyl sulfide mother liquor, phosphorus pentasulfide is added, is sufficiently stirred, obtains reaction material liquid A；
(2) it takes catalyst to be added into methanol solution, mixes, obtain reaction material liquid B；
(3) under the conditions of tiny structure, the reaction material liquid B that the step (2) obtains is added dropwise to the reaction that the step (1) obtains
In feed liquid A；And after being added dropwise to complete, insulation reaction is carried out, required O, O- dimethyl disulfide substituted phosphate are obtained.
2. the method for synthesis O according to claim 1, O- dimethyl disulfide substituted phosphate, which is characterized in that the step
(2) in, the catalyst is the mixture of pyridine and 4-dimethylaminopyridine.
3. the method for synthesis O according to claim 2, O- dimethyl disulfide substituted phosphate, which is characterized in that the catalysis
In agent, the mass ratio of the pyridine and 4-dimethylaminopyridine is 1：0.5-1.5.
4. the method for synthesis O according to claim 2 or 3, O- dimethyl disulfide substituted phosphate, which is characterized in that described
The mass ratio of catalyst and the phosphorus pentasulfide is 1-2.5：1000.
5. the method for synthesis O according to claim 1-4, O- dimethyl disulfide substituted phosphate, which is characterized in that
The molar ratio of the phosphorus pentasulfide and methanol is 1：4.02-4.05.
6. the method for synthesis O according to claim 1-5, O- dimethyl disulfide substituted phosphate, which is characterized in that
In the step (3), the step of dropwise reaction feed liquid B be start when the reaction material liquid A is heated to 25-35 DEG C into
Row.
7. the method for synthesis O according to claim 6, O- dimethyl disulfide substituted phosphate, which is characterized in that the step
(3) in, the temperature of the insulation reaction step is 50-55 DEG C.
8. the method for synthesis O according to claim 6 or 7, O- dimethyl disulfide substituted phosphate, which is characterized in that described
Tiny structure is control vacuum degree 30-50mmHg.
9. according to the described in any item synthesis O of claim 6-8, the method for O- dimethyl disulfide substituted phosphate, which is characterized in that
In the step (3), further include the steps that extracting the hydrogen sulfide that reaction generates out and being absorbed with lye.
10. the method for -9 described in any item synthesis O according to claim 1, O- dimethyl disulfide substituted phosphate, feature exist
In further including the steps that carrying out the reaction material liquid A mashing processing in the step (1).
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 |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810836759.1A CN108864181B (en) | 2018-07-26 | 2018-07-26 | Method for synthesizing O, O-dimethyl phosphorodithioate |
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| Publication Number | Publication Date |
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| CN108864181A true CN108864181A (en) | 2018-11-23 |
| CN108864181B CN108864181B (en) | 2021-04-13 |
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Cited By (2)
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| CN111440211A (en) * | 2020-04-28 | 2020-07-24 | 宁波大学科学技术学院 | Method for catalytically synthesizing malathion by one-pot method |
| CN116874524A (en) * | 2023-06-12 | 2023-10-13 | 河南嘉颖生物科技有限公司 | Continuous production process and device for high-purity O, O-dialkyl thiophosphate |
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| CN116874524A (en) * | 2023-06-12 | 2023-10-13 | 河南嘉颖生物科技有限公司 | Continuous production process and device for high-purity O, O-dialkyl thiophosphate |
| 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 |
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