CN106565779B - A kind of methyl dichloro phosphorus new technique for synthesizing - Google Patents
A kind of methyl dichloro phosphorus new technique for synthesizing Download PDFInfo
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- CN106565779B CN106565779B CN201610989024.3A CN201610989024A CN106565779B CN 106565779 B CN106565779 B CN 106565779B CN 201610989024 A CN201610989024 A CN 201610989024A CN 106565779 B CN106565779 B CN 106565779B
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- methyl dichloro
- phosphorus
- ternary complexes
- dichloro phosphorus
- aluminium powder
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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 abstract description 12
- 230000002194 synthesizing effect Effects 0.000 title abstract description 6
- 239000000843 powder Substances 0.000 claims abstract description 29
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 26
- 239000004411 aluminium Substances 0.000 claims abstract description 26
- 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
- 239000002002 slurry Substances 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 15
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000007787 solid Substances 0.000 claims abstract description 13
- 239000011780 sodium chloride Substances 0.000 claims abstract description 12
- 239000011812 mixed powder Substances 0.000 claims abstract description 5
- 238000004821 distillation Methods 0.000 claims abstract description 3
- 238000005516 engineering process Methods 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 4
- 238000004321 preservation Methods 0.000 abstract description 3
- 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
- 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
- -1 stir evenly Substances 0.000 description 5
- 238000010189 synthetic method Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 230000000694 effects Effects 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
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 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
- 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
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical class ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000013459 approach Methods 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
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000536 complexating effect Effects 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
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 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
- 239000003446 ligand Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 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
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- 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 the new technique for synthesizing of methyl dichloro phosphorus, this method is will to be heated to 140 DEG C by alchlor, chloromethanes and phosphorus trichloride solid-state ternary complexes obtained by the reaction, ternary complexes become slurries after adding in a small amount of aluminium powder heat preservation a period of time, this slurries is slowly added into the sodium chloride and aluminium powder mixed-powder equipped with preheating, 80 82 DEG C of fractions are collected in side border ring distillation, obtain the methyl dichloro phosphorus of high-purity.Using this new technique for synthesizing, avoid solid charging and be difficult to serialization, material and be easily stained with the paste drawbacks such as on the wall, it is ensured that material mutually fully reacts, and is with a wide range of applications.
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 releases chlorine
Change hydrogen, available for preparing new and effective herbicide glufosinate-ammonium.
The synthetic method of methyl dichloro phosphorus had had many reports at present, according to methane donor come point, have methane method,
Iodomethane complexometry, chloromethanes complexometry and some other synthetic methods.Methane method be using methane and phosphorus trichloride as raw material,
Catalytic synthesis of methyl phosphorus dichloride under high temperature, document report is more at present.Wherein U.S.Patent 4,518,538 [P] .1985-
5-21. uses methane and phosphorus trichloride as raw material, anti-under 500-650 DEG C and 3-6bar pressure using carbon tetrachloride as initiator
Methyl dichloro phosphorus should be prepared, shortcoming is reaction temperature height, and energy consumption is larger, and product methyl dichloro phosphorus and raw material phosphorus trichloride
Boiling point approaches, 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 and alchlor effect generation methyl chloride aluminium are prepared, then preparation cooperation is reacted with phosphorus trichloride for raw material
Object CH3PCl2·AlCl3, decomplexing obtains methyl dichloro phosphorus, yield 80%.Shortcoming is that operating procedure is more, and methyl sesquialter chlorination
Object is unstable.Li Yiming, Du Xiaohua, Yang Hongwu wait synthesis [J] pesticides of methyl dichloro phosphorus, 2011,50 (2):97-99.
It is solvent using 1,1,2,2- tetrachloroethanes, using chloromethanes, alchlor and phosphorus trichloride as the synthetic method of raw material, first 80
6h is reacted under the conditions of DEG C and obtains ternary complexes, is then distilled and is produced while reacting with aluminium reducing under the conditions of 140 DEG C
Product methyl dichloro phosphorus, total recovery 76.2%.The aluminium powder and sodium chloride for restoring the addition of decomplexing process are solids, and this reaction
Process very exothermic, solid mode, which feeds, to be difficult to accurately control reaction process, and industrialization is dangerous higher.Patent
201610095303.5 pairs of this methods are improved, and using petroleum ether as solvent, add in diethyl phthalate etc.
Yield is increased to 91% by catalyst, but fails to improve feed way, and the catalyst added in increases offal treatment hardly possible
Degree.
Invention content
Present invention aims at provide 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.
Synthetic method carries out according to the following steps successively used by its technical problem of present invention solution：
Being reacted by alchlor, phosphorus trichloride and chloromethanes for specified amount is added in the reaction kettle closed equipped with solvent
The ternary complexes of generation, control ternary complexes add the aluminium powder of specified amount in certain temperature, stir 15-50min, will
Solid complex becomes slurries, then slurries heat preservation is slowly continuously added into sodium chloride and aluminium after preheating at an established temperature
In the mixed-powder of powder, border ring distillation in side collects 80-82 DEG C of fraction and just obtains methyl dichloro phosphorus product.
Wherein：The dosage that ternary complexes are converted into aluminium powder used in slurries is the 0.1%-1.0% of ternary complexes quality；
It is 140-160 DEG C to keep the ternary complexes temperature by the reaction generation of alchlor, phosphorus trichloride and chloromethanes；Slurries heat preservation temperature
Spend is 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 that the present invention synthesizes is measured using gas-chromatography area normalization method.
Advantageous effect：The invention avoids the various problems that solid charging generates；
(1) by ternary complexes be converted into it is counter after liquid be added in aluminium powder and solid sodium chloride, reaction is easier to control, and is protected
The conversion ratio of ternary complexes is demonstrate,proved
(2) after changing feed way, the ligand moment of instillation is reduced decomplexing, releases methyl dichloro phosphorus, carries significantly
High mass-transfer efficiency avoids solid charging and is difficult to serialization, material and be easily stained with the paste drawbacks such as on the wall, it is ensured that object
Material mutually fully reaction, produces unexpected good effect.It does not need to add under conditions of catalyst, it can be by methyl dichloro
Change phosphrus reagent to be promoted to more than 94%.
Specific embodiment：
It elaborates below to the embodiment of the present invention, the present embodiment is lower based on the technical solution of the present invention to carry out in fact
It applies, gives 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 alchlors, 536.3g phosphorus trichlorides are added in closed reaction kettle,
It is passed through nitrogen and displaces air, then be passed through 300g chloromethanes, 6h is reacted at 80 DEG C, desolventizing obtains white sand shape ternary complexing
Ternary complexes are heated to 150 DEG C, add in 3.0g aluminium powders, stir evenly, solid gradually melts to be formed after 40min by object 950g
Slurries.
Slurries are kept the temperature at 150 DEG C, are slowly added into the slightly excessive aluminium powder and sodium chloride powder for being preheating to 140 DEG C,
Side border ring distills to obtain 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 alchlors, 536.3g phosphorus trichlorides are added in closed reaction kettle,
It is passed through nitrogen and displaces 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, add in 6.0g aluminium powders, stir evenly, solid gradually melts to form slurry after 50min by 952g
Liquid.
Slurries are kept the temperature at 100 DEG C, are slowly added into the slightly excessive aluminium powder and sodium chloride powder for being preheating to 160 DEG C,
Side border ring distills to obtain the methyl dichloro phosphorus of 327g contents 99.5%, yield 92.70%.
Embodiment 3：
Using 1L dichloromethane as solvent, 400.5g alchlors, 536.3g phosphorus trichlorides are added in closed reaction kettle,
It is passed through nitrogen and displaces 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, add in 2.0g aluminium powders, stir evenly, solid gradually melts to form slurry after 20min by 951g
Liquid.
Slurries are kept the temperature at 120 DEG C, are slowly added into the slightly excessive aluminium powder and sodium chloride powder for being preheating to 150 DEG C,
Side border ring distills to obtain the methyl dichloro phosphorus that 317g contents are 99.1%, yield 89.50%.
Embodiment 4：
Using 1L dichloromethane as solvent, 400.5g alchlors, 536.3g phosphorus trichlorides are added in closed reaction kettle,
It is passed through nitrogen and displaces 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, add in 8.0g aluminium powders, stir evenly, solid gradually melts to form slurry after 15min by 948g
Liquid.
Slurries are kept the temperature at 140 DEG C, are slowly added into the slightly excessive aluminium powder and sodium chloride powder for being preheating to 140 DEG C,
Side border ring distills to obtain the methyl dichloro phosphorus that 319g contents are 99.7%, yield 90.61%.
Embodiment 5：
Using 1L dichloromethane as solvent, 400.5g alchlors, 536.3g phosphorus trichlorides are added in closed reaction kettle,
It is passed through nitrogen and displaces 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, add in 4.0g aluminium powders, stir evenly, solid gradually melts to form slurry after 30min by 950g
Liquid.
Slurries are kept the temperature at 150 DEG C, are slowly added into the slightly excessive aluminium powder and sodium chloride powder for being preheating to 170 DEG C,
Side border ring distills to obtain 297g methyl dichloro phosphorus, content 99.5%, yield 84.19%.
Claims (6)
1. a kind of methyl dichloro phosphorus synthesis technology, it is characterised in that：It adopts the technology that is carried out according to the following steps:
The ternary by the reaction generation of alchlor, phosphorus trichloride and chloromethanes that specified amount is added in closed reaction kettle is complexed
Object, control ternary complexes add the aluminium powder of specified amount in certain temperature, stir 15-50min, solid complex is become
Slurries, then slurries are kept the temperature to the mixed-powder for being slowly continuously added into the sodium chloride after preheating and aluminium powder at an established temperature
In, border ring distillation in side collects 80-82 DEG C of fraction and just obtains methyl dichloro phosphorus product.
2. methyl dichloro phosphorus synthesis technology according to claim 1, it is characterised in that：Ternary complexes are converted into slurry
The dosage of aluminium powder used in liquid is the 0.1%-1.0% of ternary complexes quality.
3. methyl dichloro phosphorus synthesis technology according to claim 1, it is characterised in that：It keeps by alchlor, tri-chlorination
Phosphorus and the ternary complexes temperature of chloromethanes reaction generation are controlled at 140-160 DEG C.
4. methyl dichloro phosphorus synthesis technology according to claim 1, it is characterised in that：Slurries holding temperature is 100-
150℃。
5. methyl dichloro phosphorus synthesis technology according to claim 1, it is characterised in that：The mixed powder of aluminium powder and sodium chloride
Last preheating temperature is 120-160 DEG C.
6. methyl dichloro phosphorus synthesis technology according to claim 1, it is characterised in that：Ternary complexes are reacted with aluminium powder
Mixing time is 15-50min.
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107602608B (en) * | 2017-09-26 | 2019-04-16 | 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 |
| 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 |
| 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 |
| 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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| JPH07242682A (en) * | 1994-02-28 | 1995-09-19 | Nippon Soda Co Ltd | Production of dihalogenoalkylphosphane |
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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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| JPH07242682A (en) * | 1994-02-28 | 1995-09-19 | Nippon Soda Co Ltd | Production of dihalogenoalkylphosphane |
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