CN106083926A - A kind of synthetic method of glufosinate-ammonium intermediate alkyl di-phosphate ester compound - Google Patents
A kind of synthetic method of glufosinate-ammonium intermediate alkyl di-phosphate ester compound Download PDFInfo
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- CN106083926A CN106083926A CN201610460751.0A CN201610460751A CN106083926A CN 106083926 A CN106083926 A CN 106083926A CN 201610460751 A CN201610460751 A CN 201610460751A CN 106083926 A CN106083926 A CN 106083926A
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- glufosinate
- ammonium
- phosphate ester
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- 229910019142 PO4 Inorganic materials 0.000 title claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 13
- 239000010452 phosphate Substances 0.000 title claims abstract description 13
- 238000010189 synthetic method Methods 0.000 title claims abstract description 12
- 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 title claims abstract 10
- 238000000034 method Methods 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims description 23
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 11
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- UAYWVJHJZHQCIE-UHFFFAOYSA-L Zinc iodide Inorganic materials I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- -1 alkyl phosphoric acid diester Chemical class 0.000 abstract description 6
- 239000007983 Tris buffer Substances 0.000 abstract description 5
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract description 5
- 238000006467 substitution reaction Methods 0.000 abstract description 5
- NSWQJASYEPJGJA-UHFFFAOYSA-N CCOP(C)(O)OCC.CNC(S)=N Chemical compound CCOP(C)(O)OCC.CNC(S)=N NSWQJASYEPJGJA-UHFFFAOYSA-N 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 4
- 150000008282 halocarbons Chemical class 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- ZBMRKNMTMPPMMK-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid;azane Chemical compound [NH4+].CP(O)(=O)CCC(N)C([O-])=O ZBMRKNMTMPPMMK-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- 238000010792 warming Methods 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000009413 insulation Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 5
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 5
- 229960003750 ethyl chloride Drugs 0.000 description 5
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 4
- CDPKWOKGVUHZFR-UHFFFAOYSA-N dichloro(methyl)phosphane Chemical compound CP(Cl)Cl CDPKWOKGVUHZFR-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- AVXBTEZHGRNURI-UHFFFAOYSA-N CN=C(N)S.CN=C(N)S.COP(O)O Chemical compound CN=C(N)S.CN=C(N)S.COP(O)O AVXBTEZHGRNURI-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004176 ammonification Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- NSSMTQDEWVTEKN-UHFFFAOYSA-N diethoxy(methyl)phosphane Chemical compound CCOP(C)OCC NSSMTQDEWVTEKN-UHFFFAOYSA-N 0.000 description 1
- UTZAXPKCGJZGLB-UHFFFAOYSA-N diethyl methyl phosphite Chemical compound CCOP(OC)OCC UTZAXPKCGJZGLB-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- FFXFVWSZUMGPNE-UHFFFAOYSA-N ethoxymethylphosphonic acid Chemical class CCOCP(O)(O)=O FFXFVWSZUMGPNE-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4021—Esters of aromatic acids (P-C aromatic linkage)
-
- 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)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
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 discloses the synthetic method of a kind of glufosinate-ammonium intermediate alkyl di-phosphate ester compound.The method, with tris phosphite and halogenated hydrocarbons or alcohol or the substitution reaction of phenol, obtains glufosinate-ammonium intermediate alkyl di-phosphate ester.The present invention for raw material with tris phosphite carries out substitution reaction obtain corresponding product alkyl phosphoric acid diester with halogenated hydrocarbons or alcohol or phenol at a certain temperature, this product prepares glufosinate-ammonium further, change the technique that existing employing methylisothiouronium methylphosphite diethylester prepares glufosinate-ammonium, production cost is low, safety and environmental protection, avoids the danger in course of industrialization simultaneously.
Description
Technical field
The present invention relates to the synthetic method of a kind of organic phosphorus compound, be specifically related to a kind of herbicide glufosinate-ammonium intermediate alkane
The synthetic method of base di-phosphate ester compound.
Background technology
Glufosinate-ammonium (glufosinate-ammonium), is changed in the eighties of last century Development and Production eighties by Hoechest company
Formal name used at school claims 4-[hydroxyl (methyl) phosphono]-DL-high lactamine, also known as glufosinate-ammonium ammonium salt, for phosphorus acid herbicides.
Along with the exploitation upsurge of domestic glufosinate-ammonium, classical route gradually emerges the water surface.Hoechst is at US6359162B1
Patent proposes with methylisothiouronium methylphosphite diethylester and acrolein reaction obtain acetal product again through cyanogen generation, ammonification should obtain α-ammonia
Base nitrile compounds, then hydrolysis obtains glufosinate-ammonium；More domestic producers are with diethyl methyl-phosphonite and glycol dibromide
Or 1,2-dichloroethanes does Arbusov phosphine and obtains ethoxyl methyl phosphonic acids 2-halo ethyl ester, with this intermediate to DEAM (acetyl ammonia
Propylmalonic acid diethylester) alkylation, then hydrolysis decarboxylation obtains glufosinate-ammonium.
In above-mentioned several preparation methoies, the intermediate of glufosinate-ammonium is methylisothiouronium methylphosphite diethylester, and methylisothiouronium methylphosphite two
What the current document of synthesis of ethyl ester was reported mainly has Grignard and methyl dichloro phosphorus method, wherein alkyl halide magnesium in grignard reaction
Avoiding water, security performance is low, and yield is the highest, and large-scale production difficulty is big；The synthesis difficulty of methyl dichloro phosphorus is big, it is difficult to protect for a long time
Depositing, and methyl dichloro phosphorus synthesizing methyl diethyl phosphite needs special equipment, equipment investment cost is high.
Summary of the invention
The present invention uses with tris phosphite and halogenated hydrocarbons or the substitution reaction of alcohol, obtains glufosinate-ammonium intermediate alkyl phosphoric acid
Diester, for providing a kind of process route glufosinate-ammonium synthetic route simple, low cost, safety and environmental protection significant.This
The synthetic method of bright glufosinate-ammonium intermediate alkyl di-phosphate ester compound, reduces production cost, simplifies operating process, keeps away simultaneously
Exempt from the danger in course of industrialization.
The present invention's is a kind of with tris phosphite and halogenated hydrocarbons or alcohol or the substitution reaction of phenol, obtains glufosinate-ammonium intermediate alkane
Base di-phosphate ester, is specifically shown in following formula:
The above-mentioned purpose of the present invention is achieved through the following technical solutions:
The synthetic method of the glufosinate-ammonium intermediate alkyl di-phosphate ester compound of a kind of formula (I) of the present invention, by compound
II reacts under certain condition with compound III, produces substituent I,
Wherein, R1For the alkyl or phenyl of C1～C6, R2 is the one in methyl, ethyl or phenyl；Compound III molecule
One during X is halogen or hydroxyl in formula.
Further, in described method, reaction temperature is 80-150 DEG C, preferably 100-120 DEG C.
Further, in described method, compound II and the amount of the material of compound III are than being (1-2): 1.
Further, in described compound III, X is hydroxyl, with ZnI2It is solvent for catalyst, THF, and compound II,
Compound III, ZnI2It is (1-1.5): 1:(1-2 with the amount ratio of the material of THF): (2-5).
Compared with prior art, what the present invention produced has the technical effect that
1) present invention carries out substitution reaction with compound III with tris phosphite at a certain temperature for raw material and obtains phase
The product alkyl phosphoric acid diester answered, this product prepares glufosinate-ammonium further, changes existing employing methylisothiouronium methylphosphite diethylester system
The technique of standby glufosinate-ammonium, production cost is low, safety and environmental protection, avoids the danger in course of industrialization simultaneously；
2) the technique linking of the present invention is in order, easy and simple to handle, simplifies technological process, and the work greatly reducing workman is strong
Degree, improves labor efficiency.
Detailed description of the invention
Raw material of the present invention is the sold chemical raw material in market, below in conjunction with specific embodiment, to the present invention
It is described in detail, in order to be better understood from present disclosure.
Embodiment 1
In 500ml reactor, add the NSC 5284 of 166g (1mol), be gradually heating to 100 DEG C of insulations, to instead
In answering still, metering is passed through 25.25g (0.5mol) chloromethanes, and atmospheric pressure reflux reaction 2h, reaction is down to room temperature, by reactant liquor after terminating
Put into four-hole boiling flask to be warming up to 120 DEG C and distillate ethyl chloride and other low-boiling-point substances, distill 2-3h, then be down to room temperature, obtain colourless liquid
Body 136.4g (0.89mol), content 94.4%.
Embodiment 2
In 500ml reactor, add the NSC 5284 of 166g (1mol), be gradually heating to 100 DEG C of insulations, to instead
In answering still, metering adds 32.25g (0.5mol) ethyl chloride, and atmospheric pressure reflux reaction 2h, reaction is down to room temperature, by reactant liquor after terminating
Put into four-hole boiling flask to be warming up to 120 DEG C and distillate ethyl chloride and other low-boiling-point substances, distill 2-3h, then be down to room temperature, obtain colourless liquid
Body 143.7g (0.866mol), content 92.1%.
Embodiment 3
In 500ml reactor, add the NSC 5284 of 166g (1mol), be gradually heating to 100 DEG C of insulations, to instead
In answering still, metering adds 56.25g (0.5mol) chlorobenzene, and atmospheric pressure reflux reaction 2h, reaction is down to room temperature after terminating；Reactant liquor is put
It is warming up to 120 DEG C in entering four-hole boiling flask and distillates ethyl chloride and other low-boiling-point substances, distill 2-3h.After being down to room temperature, obtain colourless liquid
198.3g (0.927mol), content 94.9%.
Embodiment 4
500ml reactor adds the NSC 6513 of 124g (1mol), is gradually heating to 100 DEG C of insulations, to reaction
In still, metering adds 56.25g (0.5mol) chlorobenzene, and atmospheric pressure reflux reaction 2h, reaction is down to room temperature after terminating；Reactant liquor is put into
It is warming up to 120 DEG C in four-hole boiling flask and distillates chloromethanes and other low-boiling-point substances, distill 2-3h.After being down to room temperature, obtain colourless liquid
170.8g (0.918mol), content 93.6%.
Embodiment 5
47.75g (0.25mol) ZnI is added in 500ml reactor2With 72.11g (1mol) THF, gradually stir and divide
Do not add 62.25g (0.375mol) NSC 5284 and 8g (0.25mol) methanol, normal pressure, be warming up to 75 DEG C of back flow reaction
16h, reaction is down to room temperature after terminating；Being reduced pressure by reactant liquor after precipitation, with dichloromethane washing, filter, filtrate is concentrated to give colourless
Liquid 52.6g (0.346mol), content 86.9%.
Embodiment 6
In 500ml reactor, add the NSC 6513 of 124g (1mol), be gradually heating to 100 DEG C of insulations, to instead
In answering still, metering is passed through 25.25g (0.5mol) chloromethanes, and atmospheric pressure reflux reaction 2h, reaction is down to room temperature, by reactant liquor after terminating
Put into four-hole boiling flask to be warming up to 120 DEG C and distillate chloromethanes and other low-boiling-point substances, distill 2-3h, then be down to room temperature, obtain colourless liquid
Body 109.1g (0.88mol), content 92.1%.
Embodiment 7
In 500ml reactor, add the NSC 6513 of 124g (1mol), be gradually heating to 100 DEG C of insulations, to instead
In answering still, metering adds 32.25g (0.5mol) ethyl chloride, and atmospheric pressure reflux reaction 2h, reaction is down to room temperature, by reactant liquor after terminating
Put into four-hole boiling flask to be warming up to 120 DEG C and distillate chloromethanes and other low-boiling-point substances, distill 2-3h, then be down to room temperature, obtain colourless liquid
Body 113.5g (0.82mol), content 90.8%.
Embodiment 8
47.75g (0.25mol) ZnI is added in 500ml reactor2With 72.11g (1mol) THF, gradually stir and divide
Do not add 46.5g (0.375mol) NSC 6513 and 8g (0.25mol) methanol, normal pressure, be warming up to 75 DEG C of back flow reaction
16h, reaction is down to room temperature after terminating；Being reduced pressure by reactant liquor after precipitation, with dichloromethane washing, filter, filtrate is concentrated to give colourless
Liquid 41.9g (0.338mol), content 89.0%.
Embodiment 9
47.75g (0.25mol) ZnI is added in 500ml reactor2With 72.11g (1mol) THF, gradually stir and divide
Do not add 46.5g (0.375mol) NSC 5284 and 23.5g (0.25mol) phenol, normal pressure, be warming up to 75 DEG C of back flow reaction
16h, reaction is down to room temperature after terminating；Being reduced pressure by reactant liquor after precipitation, with dichloromethane washing, filter, filtrate is concentrated to give colourless
Liquid 75.8g (0.354mol), content 92.7%.
Claims (5)
1. the synthetic method of a glufosinate-ammonium intermediate alkyl di-phosphate ester compound, it is characterised in that by compound II and change
Compound III reacts under certain condition, produces substituent I,
Wherein, R1For the alkyl or phenyl of C1～C6, R2For the one in methyl, ethyl or phenyl；X in compound III molecular formula
For the one in halogen or hydroxyl.
The synthetic method of glufosinate-ammonium intermediate alkyl di-phosphate ester compound the most according to claim 1, it is characterised in that
In described method, reaction temperature is 80-150 DEG C.
The synthetic method of glufosinate-ammonium intermediate alkyl di-phosphate ester compound the most according to claim 2, it is characterised in that
In described method, reaction temperature is 100-120 DEG C.
The synthetic method of glufosinate-ammonium intermediate alkyl di-phosphate ester compound the most according to claim 1, it is characterised in that
In described method, compound II and the amount of the material of compound III are than being (1-2): 1.
The synthetic method of glufosinate-ammonium intermediate alkyl di-phosphate ester compound the most according to claim 1, it is characterised in that
In described compound III, X is hydroxyl, need to use ZnI2Catalysis, THF are solvent, and compound II, compound III, ZnI2With THF's
The amount of material is than being (1-1.5): 1:(1-2): (2-5).
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110003269A (en) * | 2019-04-29 | 2019-07-12 | 利尔化学股份有限公司 | The method of low energy consumption production glufosinate-ammonium |
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|---|---|---|---|---|
| CN105237567A (en) * | 2015-11-09 | 2016-01-13 | 河北工业大学 | Arylmethyl phosphonate preparation method |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110003269A (en) * | 2019-04-29 | 2019-07-12 | 利尔化学股份有限公司 | The method of low energy consumption production glufosinate-ammonium |
| CN110003269B (en) * | 2019-04-29 | 2022-04-05 | 利尔化学股份有限公司 | Method for producing glufosinate-ammonium with low energy consumption |
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Application publication date: 20161109 |