CN106565779A - Novel synthesis process of methyl phosphorus dichloride - Google Patents
Novel synthesis process of methyl phosphorus dichloride Download PDFInfo
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- CN106565779A CN106565779A CN201610989024.3A CN201610989024A CN106565779A CN 106565779 A CN106565779 A CN 106565779A CN 201610989024 A CN201610989024 A CN 201610989024A CN 106565779 A CN106565779 A CN 106565779A
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- Prior art keywords
- methyl dichloro
- dichloro phosphorus
- ternary complexes
- new technique
- serosity
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- CDPKWOKGVUHZFR-UHFFFAOYSA-N dichloro(methyl)phosphane Chemical compound CP(Cl)Cl CDPKWOKGVUHZFR-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims abstract description 20
- 230000015572 biosynthetic process Effects 0.000 title abstract description 6
- 238000003786 synthesis reaction Methods 0.000 title abstract description 6
- 239000000843 powder Substances 0.000 claims abstract description 28
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 25
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 24
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 24
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 20
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 15
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000011780 sodium chloride Substances 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 238000004821 distillation Methods 0.000 claims abstract description 8
- 239000011812 mixed powder Substances 0.000 claims abstract description 5
- 239000004411 aluminium Substances 0.000 claims description 21
- 230000002194 synthesizing effect Effects 0.000 claims description 9
- 238000010668 complexation reaction Methods 0.000 claims description 2
- 238000005516 engineering process Methods 0.000 claims description 2
- 238000009413 insulation Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000007787 solid Substances 0.000 abstract description 13
- 239000000463 material Substances 0.000 abstract description 4
- 210000004911 serous fluid Anatomy 0.000 abstract 2
- 230000007547 defect Effects 0.000 abstract 1
- 238000004321 preservation Methods 0.000 abstract 1
- 239000011343 solid material Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 6
- 238000006073 displacement reaction Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000004576 sand Substances 0.000 description 5
- 239000002002 slurry Substances 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910000951 Aluminide Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000007036 catalytic synthesis reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- SWRNIYAQKATHDJ-UHFFFAOYSA-N dichloro(dichlorophosphanyl)phosphane Chemical compound ClP(Cl)P(Cl)Cl SWRNIYAQKATHDJ-UHFFFAOYSA-N 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- -1 methyl chloride aluminum Chemical compound 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/52—Halophosphines
-
- 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
- C07F9/50—Organo-phosphines
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/5063—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds
- C07F9/5068—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds from starting materials having the structure >P-Hal
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)
- Crystallography & Structural Chemistry (AREA)
Abstract
The invention discloses a novel synthesis process of methyl phosphorus dichloride. According to the technical scheme of the method provided by the invention, aluminum trichloride, chloromethane and phosphorus trichloride are subjected to reaction to obtain a solid ternary complex. The solid ternary complex is heated to 140 DEG C and then a small amount of aluminum powders is added. After the heat preservation process for a certain period of time, the ternary complex is turned into a serous fluid and the serous fluid is slowly added into the pre-heated mixed powders of sodium chloride and aluminum powders. The distillation is conducted while reacting, and then fractions of 80-82 DEG C are collected. In this way, the high-purity methyl phosphorus dichloride is obtained. Based on the novel synthesis process, the defects that solid materials are hard to be continuously added, and materials easily stick onto the wall of a container in the prior art can be avoided. The sufficient reaction of materials is ensured, so that the novel synthesis process has a wide application prospect.
Description
Technical field
This patent belongs to pesticide intermediate preparing technical field, and in particular to a kind of glufosinate-ammonium intermediate methyl dichloro phosphorus
New technique for synthesizing.
Background technology
Methyl dichloro phosphorus is the liquid that a kind of water white transparency has intense irritation smell, and chance water is inflammable and discharges chlorine
Change hydrogen, can be used to prepare new and effective herbicide glufosinate-ammonium.
At present the synthetic method of methyl dichloro phosphorus had had many reports, according to methane donor come point, have methane method,
Iodomethane complexometry, chloromethanes complexometry and some other synthetic methods.Methane method be with methane and Phosphorous chloride. as raw material,
Catalytic synthesis of methyl phosphorus dichloride under high temperature, current document report are more.Wherein U.S.Patent 4,518,538 [P] .1985-
5-21. adopts methane and Phosphorous chloride. for raw material, with carbon tetrachloride as initiator, anti-under 500-650 DEG C and 3-6bar pressure
Methyl dichloro phosphorus should be prepared, has the disadvantage that reaction temperature is high, energy consumption is larger, and product methyl dichloro phosphorus and raw material Phosphorous chloride.
Boiling point is close to, and separation costs are very high.U.S.Patent 3,840,576 [P] .1974-10-8. is proposed by aluminium powder and chloromethanes
Methyl sesquialter aluminide is prepared for raw material and methyl chloride aluminum is generated with aluminum chloride effect, then coordinate with Phosphorous chloride. reaction preparation
Thing CH3PCl2·AlCl3, decomplexing obtains methyl dichloro phosphorus, yield 80%.Have the disadvantage that operating procedure is more, and methyl sesquialter chlorination
Thing is unstable.Li Yiming, Du Xiaohua, Yang Hongwu, etc. the synthesis [J] of methyl dichloro phosphorus. pesticide, 2011,50 (2):97-99.
Sym.-tetrachloroethane is adopted for solvent, the synthetic method with chloromethanes, aluminum chloride and Phosphorous chloride. as raw material, first 80
6h is reacted under the conditions of DEG C and obtains ternary complexes, then aluminium reducing is used under the conditions of 140 DEG C, react to distill and produced
Product methyl dichloro phosphorus, total recovery is 76.2%.The aluminium powder and Sodium Chloride that reduction decomplexing process is added is solid, and this reaction
Process very exothermic, solid mode feed and are difficult to precise control reaction process, and industrialization is dangerous higher.Patent
201610095303.5 pairs of this methods are improved, and using petroleum ether as solvent, add diethyl phthalate etc.
Yield is brought up to 91% by catalyst, but fails to improve feed way, and the catalyst for adding increased offal treatment hardly possible
Degree.
The content of the invention
Present invention aim at providing a kind of change charging order and mode to solve the methyl two of the deficiencies in the prior art
Phosphorus chloride new technique for synthesizing.
What the synthetic method adopted by its technical problem of solution of the invention was carried out successively according to the following steps：
Being reacted by aluminum chloride, Phosphorous chloride. and chloromethanes for ormal weight is added in the reactor closed equipped with solvent
The ternary complexes of generation, control ternary complexes add the aluminium powder of ormal weight in uniform temperature, stir 15-50min, will
Solid complex becomes serosity, then serosity is incubated the Sodium Chloride and aluminum being slowly continuously added into after preheating at an established temperature
In the mixed-powder of powder, border ring distillation in side is collected 80-82 DEG C of fraction and just obtains methyl dichloro phosphorus product.
Wherein：Ternary complexes are converted into the 0.1%-1.0% that the consumption of aluminium powder used by serosity is ternary complexes quality；
It is 140-160 DEG C to keep the ternary complexes temperature for generating is reacted by aluminum chloride, Phosphorous chloride. and chloromethanes；Serosity insulation temperature
Spend for 100-150 DEG C；The mixed-powder preheating temperature of aluminium powder and Sodium Chloride is 120-160 DEG C.
The phosphorus dichloride product purity of present invention synthesis is determined using gas chromatogram area normalization method.
Beneficial effect：Present invention, avoiding the various problems that solid charging is produced；
(1) by ternary complexes be converted into it is counter after liquid be added in aluminium powder and solid sodium chloride, reaction is easily controlled, and is protected
The conversion ratio of ternary complexes is demonstrate,proved
(2), after changing feed way, the part moment of instillation is reduced decomplexing, discharges methyl dichloro phosphorus, carries significantly
High mass-transfer efficiency, it is to avoid solid charging is difficult to serialization, material and is easily stained with the paste drawback such as on the wall, it is ensured that thing
Material mutually fully reacts, and generates unexpected good effect.Under conditions of catalyst need not being added, can be by methyl dichloro
Change phosphrus reagent and lift more than 94%.
Specific embodiment：
Below embodiments of the invention are elaborated, the present embodiment premised on technical solution of the present invention under carry out reality
Apply, give detailed embodiment and specific operating process, but protection scope of the present invention is not limited to following embodiments.
Embodiment 1：
Using 1L dichloromethane as solvent, 400.5g aluminum chlorides, 536.3g Phosphorous chloride .s are added in closed reactor,
It is passed through nitrogen displacement and goes out air, then be passed through 300g chloromethanes, 6h is reacted at 80 DEG C, desolventizing obtains white sand shape ternary complexation
Ternary complexes are heated to 150 DEG C by thing 950g, are added 3.0g aluminium powders, are stirred, and after 40min, solid gradually melts to be formed
Serosity.
Serosity is incubated at 150 DEG C, is slowly added into and is preheating in 140 DEG C of slightly excessive aluminium powder and sodium chloride powder,
Side border ring distillation obtains the methyl dichloro phosphorus of methyl dichloro phosphorus product 335g contents 94.87%, yield 94.87%.
Embodiment 2：
Using 1L dichloromethane as solvent, 400.5g aluminum chlorides, 536.3g Phosphorous chloride .s are added in closed reactor,
It is passed through nitrogen displacement and goes out air, 300g chloromethanes reacts 6h at 80 DEG C, and desolventizing obtains white sand shape ternary complexes
Ternary complexes are heated to 140 DEG C by 952g, are added 6.0g aluminium powders, are stirred, and after 50min, solid gradually melts to form slurry
Liquid.
Serosity is incubated at 100 DEG C, is slowly added into and is preheating in 160 DEG C of slightly excessive aluminium powder and sodium chloride powder,
Side border ring distillation obtains the methyl dichloro phosphorus of 327g contents 99.5%, yield 92.70%.
Embodiment 3：
Using 1L dichloromethane as solvent, 400.5g aluminum chlorides, 536.3g Phosphorous chloride .s are added in closed reactor,
It is passed through nitrogen displacement and goes out air, 300g chloromethanes reacts 6h at 80 DEG C, and desolventizing obtains white sand shape ternary complexes
Ternary complexes are heated to 160 DEG C by 951g, are added 2.0g aluminium powders, are stirred, and after 20min, solid gradually melts to form slurry
Liquid.
Serosity is incubated at 120 DEG C, is slowly added into and is preheating in 150 DEG C of slightly excessive aluminium powder and sodium chloride powder,
Side border ring distillation obtains the methyl dichloro phosphorus that 317g contents are 99.1%, yield 89.50%.
Embodiment 4：
Using 1L dichloromethane as solvent, 400.5g aluminum chlorides, 536.3g Phosphorous chloride .s are added in closed reactor,
It is passed through nitrogen displacement and goes out air, 300g chloromethanes reacts 6h at 80 DEG C, and desolventizing obtains white sand shape ternary complexes
Ternary complexes are heated to 155 DEG C by 948g, are added 8.0g aluminium powders, are stirred, and after 15min, solid gradually melts to form slurry
Liquid.
Serosity is incubated at 140 DEG C, is slowly added into and is preheating in 140 DEG C of slightly excessive aluminium powder and sodium chloride powder,
Side border ring distillation obtains the methyl dichloro phosphorus that 319g contents are 99.7%, yield 90.61%.
Embodiment 5：
Using 1L dichloromethane as solvent, 400.5g aluminum chlorides, 536.3g Phosphorous chloride .s are added in closed reactor,
It is passed through nitrogen displacement and goes out air, 300g chloromethanes reacts 6h at 80 DEG C, and desolventizing obtains white sand shape ternary complexes
Ternary complexes are heated to 150 DEG C by 950g, are added 4.0g aluminium powders, are stirred, and after 30min, solid gradually melts to form slurry
Liquid.
Serosity is incubated at 150 DEG C, is slowly added into and is preheating in 170 DEG C of slightly excessive aluminium powder and sodium chloride powder,
Side border ring distillation obtains 297g methyl dichloro phosphorus, content 99.5%, yield 84.19%.
Claims (6)
1. a kind of methyl dichloro phosphorus new technique for synthesizing, it is characterised in that：Which adopts the technology that what is carried out according to the following steps:
Ormal weight is added in closed reactor is reacted the ternary complexation for generating by aluminum chloride, Phosphorous chloride. and chloromethanes
Thing, control ternary complexes add the aluminium powder of ormal weight, stirring certain hour (15-50min), by solid-state in uniform temperature
Coordination compound becomes serosity, then serosity insulation is slowly continuously added into Sodium Chloride and aluminium powder after preheating at an established temperature
In mixed-powder, border ring distillation in side is collected 80-82 DEG C of fraction and just obtains methyl dichloro phosphorus product.
2. methyl dichloro phosphorus new technique for synthesizing according to claim 1, it is characterised in that：Ternary complexes are converted into
The consumption of aluminium powder used by serosity is the 0.1%-1.0% of ternary complexes quality.
3. methyl dichloro phosphorus new technique for synthesizing according to claim 1, it is characterised in that：Keep by aluminum chloride, trichlorine
Change the ternary complexes temperature control of phosphorus and chloromethanes reaction generation at 140-160 DEG C.
4. a kind of methyl dichloro phosphorus new technique for synthesizing according to claim 1, it is characterised in that：Serosity holding temperature is
100-150℃。
5. a kind of methyl dichloro phosphorus new technique for synthesizing according to claim 1, it is characterised in that：Aluminium powder and Sodium Chloride
Mixed-powder preheating temperature is 120-160 DEG C.
6. a kind of methyl dichloro phosphorus new technique for synthesizing according to claim 1, it is characterised in that：Ternary complexes and aluminum
Powder reaction mixing time is 15-50min.
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| CN201610989024.3A CN106565779B (en) | 2016-11-10 | 2016-11-10 | A kind of methyl dichloro phosphorus new technique for synthesizing |
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| CN201610989024.3A CN106565779B (en) | 2016-11-10 | 2016-11-10 | A kind of methyl dichloro phosphorus new technique for synthesizing |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107602608A (en) * | 2017-09-26 | 2018-01-19 | 安徽国星生物化学有限公司 | A kind of preparation method of diethyl methyl-phosphonite |
| CN107912446A (en) * | 2017-12-02 | 2018-04-17 | 南通江山农药化工股份有限公司 | Recycling salt containing glyphosate, Trimethyl phosphite prepares the method and its device of glufosinate-ammonium composite pesticide |
| CN108864190A (en) * | 2018-08-01 | 2018-11-23 | 河北威远生物化工有限公司 | A method of producing alkyl phosphorus dichloride |
| CN109705160A (en) * | 2019-02-25 | 2019-05-03 | 安徽国星生物化学有限公司 | A kind of synthetic method of methyl dichloro phosphorus |
| CN112028937A (en) * | 2020-09-03 | 2020-12-04 | 浙江新安化工集团股份有限公司 | Preparation method and preparation system for synthesizing methyl phosphine dichloride through one-step method |
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| CN106046052A (en) * | 2016-06-27 | 2016-10-26 | 安徽国星生物化学有限公司 | Synthesis method of glufosinate-ammonium intermediate methylphosphorus dichloride |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107602608A (en) * | 2017-09-26 | 2018-01-19 | 安徽国星生物化学有限公司 | A kind of preparation method of diethyl methyl-phosphonite |
| CN107912446A (en) * | 2017-12-02 | 2018-04-17 | 南通江山农药化工股份有限公司 | Recycling salt containing glyphosate, Trimethyl phosphite prepares the method and its device of glufosinate-ammonium composite pesticide |
| CN108864190A (en) * | 2018-08-01 | 2018-11-23 | 河北威远生物化工有限公司 | A method of producing alkyl phosphorus dichloride |
| CN108864190B (en) * | 2018-08-01 | 2020-08-07 | 河北威远生物化工有限公司 | Method for producing alkyl phosphorus dichloride |
| CN109705160A (en) * | 2019-02-25 | 2019-05-03 | 安徽国星生物化学有限公司 | A kind of synthetic method of methyl dichloro phosphorus |
| CN109705160B (en) * | 2019-02-25 | 2021-05-14 | 安徽国星生物化学有限公司 | Synthesis method of methyl phosphorus dichloride |
| CN112028937A (en) * | 2020-09-03 | 2020-12-04 | 浙江新安化工集团股份有限公司 | Preparation method and preparation system for synthesizing methyl phosphine dichloride through one-step method |
| CN112028937B (en) * | 2020-09-03 | 2021-05-14 | 浙江新安化工集团股份有限公司 | Preparation method and preparation system for synthesizing methyl phosphine dichloride through one-step method |
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| CN106565779B (en) | 2018-06-19 |
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