CN110407872A - The method of alkyl chlorination phosphonic acids list alkyl ester co-producing high-purity phosphorus oxychloride - Google Patents
The method of alkyl chlorination phosphonic acids list alkyl ester co-producing high-purity phosphorus oxychloride Download PDFInfo
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- CN110407872A CN110407872A CN201910676467.0A CN201910676467A CN110407872A CN 110407872 A CN110407872 A CN 110407872A CN 201910676467 A CN201910676467 A CN 201910676467A CN 110407872 A CN110407872 A CN 110407872A
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- Prior art keywords
- alkyl
- phosphorus oxychloride
- chlorination
- phosphonic acids
- solvent
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 title claims abstract description 96
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 27
- 238000005660 chlorination reaction Methods 0.000 title claims abstract description 26
- 125000005907 alkyl ester group Chemical group 0.000 title claims abstract description 24
- 150000003009 phosphonic acids Chemical class 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 17
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims abstract description 16
- -1 alkyl phosphonic acid Chemical compound 0.000 claims abstract description 14
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims abstract description 12
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000011084 recovery Methods 0.000 claims abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- 238000010025 steaming Methods 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 230000006837 decompression Effects 0.000 claims 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- YHQMSHVVGOSZEW-UHFFFAOYSA-N 1-dimethoxyphosphorylethane Chemical compound CCP(=O)(OC)OC YHQMSHVVGOSZEW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- STUSTWKEFDQFFZ-UHFFFAOYSA-N Chlordimeform Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-UHFFFAOYSA-N 0.000 description 1
- NJLHHACGWKAWKL-UHFFFAOYSA-N ClP(Cl)=O Chemical compound ClP(Cl)=O NJLHHACGWKAWKL-UHFFFAOYSA-N 0.000 description 1
- CGSLYBDCEGBZCG-UHFFFAOYSA-N Octicizer Chemical compound C=1C=CC=CC=1OP(=O)(OCC(CC)CCCC)OC1=CC=CC=C1 CGSLYBDCEGBZCG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XFDJMIHUAHSGKG-UHFFFAOYSA-N chlorethoxyfos Chemical compound CCOP(=S)(OCC)OC(Cl)C(Cl)(Cl)Cl XFDJMIHUAHSGKG-UHFFFAOYSA-N 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003987 organophosphate pesticide Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000008031 plastic plasticizer Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B25/00—Phosphorus; Compounds thereof
- C01B25/10—Halides or oxyhalides of phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/42—Halides thereof
- C07F9/425—Acid or estermonohalides thereof, e.g. RP(=X)(YR)(Hal) (X, Y = O, S; R = H, or hydrocarbon group)
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)
- Inorganic Chemistry (AREA)
Abstract
The invention discloses a kind of methods of alkyl chlorination phosphonic acids list alkyl ester co-producing high-purity phosphorus oxychloride, the following steps are included: (1) reacts phosphorus pentachloride and alkyl phosphonic acid dialkyl in a solvent, the mixture of alkyl chlorination phosphonic acids list alkyl ester and phosphorus oxychloride containing solvent is obtained；Gas phase monochloro methane or monochlorethane are generated in reaction process；(2) the gas phase monochloro methane or monochlorethane, solvent, alkyl chlorination phosphonic acids list alkyl ester and the phosphorus oxychloride that generate in reaction are separated and recovered.The present invention is to prepare alkyl chlorination phosphonic acids list alkyl ester simultaneously with phosphorus pentachloride and alkyl phosphonic acid dialkyl reaction, produce the mixture of a large amount of phosphorus oxychloride and solvent, have found suitable recovery method, the phosphorus oxychloride of co-producing high-purity, it can get preferable economic benefit, while reducing the discharge of the three wastes.
Description
Technical field
The present invention relates to a kind of methods of alkyl chlorination phosphonic acids list alkyl ester co-producing high-purity phosphorus oxychloride.
Background technique
Phosphorus oxychloride is the raw material for manufacturing organophosphorus pesticide Spanon, it can also be used to produce diphenyl 2 ethylhexyl phosphate, phosphoric acid
The phosphates such as triethyl and production plastic plasticizer, are alternatively arranged as the chlorinating agent, catalyst and uranium ore extractant of organic synthesis, In
There is important application in Chemical Manufacture.
Phosphorus pentachloride is a kind of important chlorination reagent, it can with hydroxy compounds, carboxylic acid, carbonyls, alkene,
Compound, sulfonic acid and its salt, silicon compound containing lone pair electrons etc. carry out chlorination reaction, and the activity of phosphorus pentachloride is very big, it
Displacement reaction is fiercer, and reaction generates phosphorus oxychloride.
Summary of the invention
It is abundant to phosphorus oxychloride during preparing alkyl chlorination phosphonic acids list alkyl ester that the purpose of the present invention is to provide one kind
The method of the alkyl chlorination phosphonic acids list alkyl ester co-producing high-purity phosphorus oxychloride of recycling.
The technical solution of the invention is as follows:
A kind of method of alkyl chlorination phosphonic acids list alkyl ester co-producing high-purity phosphorus oxychloride, it is characterized in that: the following steps are included:
(1) phosphorus pentachloride and alkyl phosphonic acid dialkyl are reacted in a solvent, obtains the alkyl chlorination containing solvent
The mixture of phosphonic acids list alkyl ester and phosphorus oxychloride；Gas phase monochloro methane or monochlorethane are generated in reaction process；
Reaction equation:
(2) to the gas phase monochloro methane or monochlorethane generated in reaction, using pressure recovery after condensation, washing, drying；
(3) mixture of alkyl chlorination the phosphonic acids list alkyl ester and phosphorus oxychloride containing solvent generated to reaction, is subtracted
Pressure distillation, steaming thing are the mixture of solvent and phosphorus oxychloride, and residue is alkyl chlorination phosphonic acids list alkyl ester；
(4) atmospheric distillation is carried out to the mixture of step (3) obtained solvent and phosphorus oxychloride, first steamed low-boiling molten
Agent can be back to next secondary response, and remaining is phosphorus oxychloride and a small amount of high-boiling-point impurity, then is evaporated under reduced pressure, and reception evaporates
Part obtains high-purity phosphorus oxychloride.
The reaction temperature of step (1) is -30~30 DEG C；Phosphorus pentachloride is to be added portionwise under nitrogen protection or molten with solvent
It is added dropwise after being added dropwise or dissolve after solution.
Solvent described in step (1) be the halogenated alkanes such as methylene chloride, 1,2- dichloroethanes, carbon tetrachloride, carbon disulfide,
Hexamethylene, benzene, toluene etc..
Alkyl phosphonic acid dialkyl described in step (1) refers toThe alkyl such as R=-CH3 ,-C2H5 replace alkane
Base, R1=-CH3 ,-C2H5；R, R1 can be identical or different.
The molal weight of alkyl phosphonic acid dialkyl and phosphorus oxychloride ratio is 1:0.99~1.05 in step (1)；
The method of step (4) rectifying separates solvent and phosphorus oxychloride, then is evaporated under reduced pressure, and receives fraction, obtains
The phosphorus oxychloride of high-purity.
The present invention is produced while preparing alkyl chlorination phosphonic acids list alkyl ester with phosphorus pentachloride and alkyl phosphonic acid dialkyl reaction
The mixture for having given birth to a large amount of phosphorus oxychloride and solvent has found suitable recovery method, and the phosphorus oxychloride of co-producing high-purity can
Preferable economic benefit is obtained, while reducing the discharge of the three wastes.The present invention is raw using phosphorus pentachloride and alkyl phosphonic acid dialkyl
At the mixture of alkyl chlorination phosphonic acids list alkyl ester and phosphorus oxychloride, further according to the different physical characteristic of material in mixture, technology
Step-by-step processing is carried out to property, to produce the phosphorus oxychloride of high-content while corresponding phosphonic chloride is made.
Below with reference to embodiment, the invention will be further described.
Specific embodiment
Embodiment 1:
By in 150ml dichloroethanes and 40g dimethyl methyl phosphonate investment tetra- mouthfuls of reaction flasks of 500ml, starting is stirred, simultaneously
Cooling feed liquid is to 0 DEG C or so, under nitrogen protection, phosphorus pentachloride 68g is added in three times, controls 0-5 DEG C of feed liquid temperature, finish,
It carrying out insulation reaction 0.5 hour, is then evaporated under reduced pressure, steaming thing is the mixture 225g of dichloroethanes and phosphorus oxychloride,
Residue is 47g methyl chloride methyl-phosphonate；To the gas phase monochloro methane generated in reaction, using condensation, washing, it is dry after press
It retracts and receives；The mixture of atmospheric distillation solvent 225g dichloroethanes and phosphorus oxychloride first steams low boiling point dichloroethanes 170g, can
It is back to next secondary response；Remaining is phosphorus oxychloride and a small amount of high-boiling-point impurity, then is evaporated under reduced pressure, and receives fraction and obtains three
Chlorethoxyfos 43g, detection level 98.1%, remaining high-boiling components 8g.
Embodiment 2:
By in 150ml dichloroethanes and 44.5g ethylphosphonic acid dimethyl ester investment tetra- mouthfuls of reaction flasks of 500ml, starting is stirred, together
When cooling feed liquid to 0 DEG C or so, under nitrogen protection, phosphorus pentachloride 68g is added in three times, controls 0-5 DEG C of feed liquid temperature, add
Finish, carry out insulation reaction 0.5 hour, be then evaporated under reduced pressure, steaming thing is the mixture of dichloroethanes and phosphorus oxychloride
226g, residue are 50g ethylmercury chloride methyl-phosphonate；To the gas phase monochloro methane generated in reaction, using condensation, washing, do
Pressure recovery after dry；The mixture of atmospheric distillation solvent 226g dichloroethanes and phosphorus oxychloride, first steams low boiling point dichloroethanes
171g can be back to next secondary response；Remaining is phosphorus oxychloride and a small amount of high-boiling-point impurity, then is evaporated under reduced pressure, and is received
Fraction obtains phosphorus oxychloride 42g, detection level 98.3%, remaining high-boiling components 8.2g.
Claims (6)
1. a kind of method of alkyl chlorination phosphonic acids list alkyl ester co-producing high-purity phosphorus oxychloride, it is characterized in that: the following steps are included:
(1) phosphorus pentachloride and alkyl phosphonic acid dialkyl are reacted in a solvent, obtains the alkyl chlorination phosphonic acids containing solvent
The mixture of single alkyl ester and phosphorus oxychloride；Gas phase monochloro methane or monochlorethane are generated in reaction process；
(2) to the gas phase monochloro methane or monochlorethane generated in reaction, using pressure recovery after condensation, washing, drying；
(3) mixture of alkyl chlorination the phosphonic acids list alkyl ester and phosphorus oxychloride containing solvent generated to reaction, carries out decompression steaming
It evaporates, steaming thing is the mixture of solvent and phosphorus oxychloride, and residue is alkyl chlorination phosphonic acids list alkyl ester；
(4) atmospheric distillation is carried out to the mixture of step (3) obtained solvent and phosphorus oxychloride, first steams low-boiling solvent,
It can be back to next secondary response, remaining is phosphorus oxychloride and a small amount of high-boiling-point impurity, then is evaporated under reduced pressure, and receives fraction and obtains
High-purity phosphorus oxychloride.
2. the method for alkyl chlorination phosphonic acids list alkyl ester co-producing high-purity phosphorus oxychloride according to claim 1, it is characterized in that:
The reaction temperature of step (1) is -30~30 DEG C；Phosphorus pentachloride is to be added portionwise or drip under nitrogen protection after being dissolved with solvent
Add.
3. the method for alkyl chlorination phosphonic acids list alkyl ester co-producing high-purity phosphorus oxychloride according to claim 1, it is characterized in that:
Solvent described in step (1) be include methylene chloride, 1,2- dichloroethanes, the halogenated alkane of carbon tetrachloride, carbon disulfide, hexamethylene
Alkane, benzene or toluene.
4. the method for alkyl chlorination phosphonic acids list alkyl ester co-producing high-purity phosphorus oxychloride according to claim 1, it is characterized in that:
Alkyl phosphonic acid dialkyl described in step (1) refers toR=-CH3、-C2H5Equal alkyl replace alkyl, R1=-
CH3、-C2H5；R,R1It can be identical or different.
5. the method for alkyl chlorination phosphonic acids list alkyl ester co-producing high-purity phosphorus oxychloride according to claim 1, it is characterized in that:
The molal weight of alkyl phosphonic acid dialkyl and phosphorus oxychloride ratio is 1:0.99~1.05 in step (1).
6. the method for alkyl chlorination phosphonic acids list alkyl ester co-producing high-purity phosphorus oxychloride according to claim 1, it is characterized in that:
The method of step (4) rectifying separates solvent and phosphorus oxychloride, then is evaporated under reduced pressure, and receives fraction, obtains high-purity
Phosphorus oxychloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910676467.0A CN110407872A (en) | 2019-07-25 | 2019-07-25 | The method of alkyl chlorination phosphonic acids list alkyl ester co-producing high-purity phosphorus oxychloride |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910676467.0A CN110407872A (en) | 2019-07-25 | 2019-07-25 | The method of alkyl chlorination phosphonic acids list alkyl ester co-producing high-purity phosphorus oxychloride |
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| Publication Number | Publication Date |
|---|---|
| CN110407872A true CN110407872A (en) | 2019-11-05 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910676467.0A Pending CN110407872A (en) | 2019-07-25 | 2019-07-25 | The method of alkyl chlorination phosphonic acids list alkyl ester co-producing high-purity phosphorus oxychloride |
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|---|---|
| CN (1) | CN110407872A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100522967C (en) * | 2002-02-01 | 2009-08-05 | 阿里亚德基因治疗公司 | Phosphorus-containing compounds & uses thereof |
-
2019
- 2019-07-25 CN CN201910676467.0A patent/CN110407872A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100522967C (en) * | 2002-02-01 | 2009-08-05 | 阿里亚德基因治疗公司 | Phosphorus-containing compounds & uses thereof |
Non-Patent Citations (3)
| Title |
|---|
| YONG XU等: "Chemical Synthesis and Molecular Recognition of ChemicalSynthesis and Molecular Recognition of Phosphatase-Resistant Analogues of Phosphatidylinositol-3-phosphate", 《J.AM.CHEM.SOC.》 * |
| 尹志刚 主编: "《有机磷化合物》", 31 March 2011, 北京：化学工业出版社 * |
| 赵临襄 主编: "《化学制药工艺学 （第4版）》", 31 August 2015, 北京:中国医药科技出版社 * |
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Application publication date: 20191105 |