RU2275376C2 - Способ получения 2-амино-4-[гидрокси(метил)фосфинил]масляной кислоты - Google Patents
Способ получения 2-амино-4-[гидрокси(метил)фосфинил]масляной кислоты Download PDFInfo
- Publication number
- RU2275376C2 RU2275376C2 RU2000107139/04A RU2000107139A RU2275376C2 RU 2275376 C2 RU2275376 C2 RU 2275376C2 RU 2000107139/04 A RU2000107139/04 A RU 2000107139/04A RU 2000107139 A RU2000107139 A RU 2000107139A RU 2275376 C2 RU2275376 C2 RU 2275376C2
- Authority
- RU
- Russia
- Prior art keywords
- formula
- carbon atoms
- stage
- alkyl
- hydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 title abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 40
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract description 33
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 15
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims abstract description 14
- 235000019270 ammonium chloride Nutrition 0.000 claims abstract description 13
- 239000011541 reaction mixture Substances 0.000 claims abstract description 11
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 8
- 150000002576 ketones Chemical class 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 5
- 150000001298 alcohols Chemical class 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 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 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- -1 methylphosphorus compound Chemical class 0.000 abstract description 28
- 239000000126 substance Substances 0.000 abstract description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract 1
- 230000002708 enhancing effect Effects 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 150000003863 ammonium salts Chemical class 0.000 description 12
- BGDOUYCSLAVFRE-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]-2-methylbutanoic acid Chemical compound OC(=O)C(N)(C)CCP(C)(O)=O BGDOUYCSLAVFRE-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000005219 aminonitrile group Chemical group 0.000 description 8
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical class C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 125000004438 haloalkoxy group Chemical group 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000005561 Glufosinate Substances 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- NYYLZXREFNYPKB-UHFFFAOYSA-N 1-[ethoxy(methyl)phosphoryl]oxyethane Chemical compound CCOP(C)(=O)OCC NYYLZXREFNYPKB-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000007059 Strecker synthesis reaction Methods 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- CDPKWOKGVUHZFR-UHFFFAOYSA-N dichloro(methyl)phosphane Chemical compound CP(Cl)Cl CDPKWOKGVUHZFR-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 0 CP(CCC(*)(C(O)=O)N)(O)=O Chemical compound CP(CCC(*)(C(O)=O)N)(O)=O 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- NSYAVDXCNTYNJL-UHFFFAOYSA-N OC(=O)C(N)(C)CCP(=O)CO Chemical compound OC(=O)C(N)(C)CCP(=O)CO NSYAVDXCNTYNJL-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- ICAIHGOJRDCMHE-UHFFFAOYSA-O ammonium cyanide Chemical compound [NH4+].N#[C-] ICAIHGOJRDCMHE-UHFFFAOYSA-O 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003017 phosphorus Chemical class 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657172—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and one oxygen atom being part of a (thio)phosphinic acid ester: (X = O, S)
-
- 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
-
- 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3211—Esters of acyclic saturated acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19736125A DE19736125A1 (de) | 1997-08-20 | 1997-08-20 | Verfahren zur Herstellung von Glufosinate und phosphorhaltige alpha-Aminonitrile als Zwischenprodukte |
| DE19736125.0 | 1997-08-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2000107139A RU2000107139A (ru) | 2001-12-20 |
| RU2275376C2 true RU2275376C2 (ru) | 2006-04-27 |
Family
ID=7839559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2000107139/04A RU2275376C2 (ru) | 1997-08-20 | 1998-08-08 | Способ получения 2-амино-4-[гидрокси(метил)фосфинил]масляной кислоты |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6359162B1 (OSRAM) |
| EP (1) | EP1005475B1 (OSRAM) |
| JP (1) | JP4519316B2 (OSRAM) |
| KR (1) | KR100674326B1 (OSRAM) |
| CN (1) | CN1261442C (OSRAM) |
| AR (1) | AR015932A1 (OSRAM) |
| AT (1) | ATE258180T1 (OSRAM) |
| AU (1) | AU756471B2 (OSRAM) |
| BR (1) | BR9811971B1 (OSRAM) |
| CA (1) | CA2301181C (OSRAM) |
| CO (1) | CO5031316A1 (OSRAM) |
| CZ (1) | CZ2000593A3 (OSRAM) |
| DE (2) | DE19736125A1 (OSRAM) |
| DK (1) | DK1005475T3 (OSRAM) |
| ES (1) | ES2214727T3 (OSRAM) |
| HU (1) | HUP0003501A3 (OSRAM) |
| IL (1) | IL134633A0 (OSRAM) |
| MY (1) | MY132853A (OSRAM) |
| PH (1) | PH11998002119A1 (OSRAM) |
| PL (1) | PL191587B1 (OSRAM) |
| PT (1) | PT1005475E (OSRAM) |
| RU (1) | RU2275376C2 (OSRAM) |
| TR (1) | TR200000456T2 (OSRAM) |
| TW (1) | TW530063B (OSRAM) |
| UA (1) | UA66806C2 (OSRAM) |
| WO (1) | WO1999009039A1 (OSRAM) |
| ZA (1) | ZA987465B (OSRAM) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2323223C2 (ru) * | 2002-03-21 | 2008-04-27 | Шеринг Акциенгезельшафт | Ингибиторы карбоксипептидазы b плазмы (крови) |
| RU2799336C2 (ru) * | 2019-01-11 | 2023-07-04 | СиДжей ЧеилДжеданг Корпорейшн | Способ получения промежуточного соединения L-глюфосината и L-глюфосината |
| US12252502B2 (en) | 2019-01-11 | 2025-03-18 | Cj Cheiljedang Corporation | L-glufosinate intermediate and L-glufosinate preparation method |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7795464B2 (en) | 2006-09-20 | 2010-09-14 | Meiji Seika Kaisha Ltd. | Method for producing α-amino acid including phosphorus and production intermediates thereof |
| BR112012026205A2 (pt) | 2010-04-14 | 2015-11-03 | Strategic Enzyme Applic Inc | processo para produção enzimática de um produto de fosfinotricina ou um precursor do mesmo |
| CN102372738B (zh) * | 2010-08-14 | 2017-11-10 | 武汉工程大学 | Lj反应在制备维蒂希试剂和草铵膦中的应用 |
| MY167395A (en) | 2011-09-30 | 2018-08-16 | Meiji Seika Pharma Co Ltd | Method for producing glufosinate p free acid |
| CN102372739B (zh) * | 2011-12-05 | 2017-06-16 | 河北威远生化农药有限公司 | 一种草铵膦的合成方法 |
| CN102399240A (zh) * | 2011-12-27 | 2012-04-04 | 江苏优士化学有限公司 | 一种改进的草铵膦及类似物的合成方法 |
| CN102399239A (zh) * | 2011-12-27 | 2012-04-04 | 江苏优士化学有限公司 | 一种草铵膦及类似物的合成方法 |
| CN103183707B (zh) * | 2011-12-30 | 2016-06-15 | 中化蓝天集团有限公司 | 一种草胺膦的制备方法 |
| CN102584893B (zh) * | 2012-02-07 | 2015-03-04 | 浙江工业大学 | 一种草铵膦的制备方法 |
| CN103374030B (zh) * | 2012-04-13 | 2016-03-23 | 浙江新安化工集团股份有限公司 | 一种制备草铵膦的方法及其中间体的制备方法 |
| CN103483379A (zh) * | 2013-09-26 | 2014-01-01 | 江苏辉丰农化股份有限公司 | 一种草铵膦酸的制备方法 |
| CN113264958A (zh) * | 2014-05-13 | 2021-08-17 | 拜耳作物科学股份公司 | 制备含磷羟腈的方法 |
| CN104558033B (zh) * | 2014-12-19 | 2016-05-18 | 浙江工业大学 | 一种l-草铵膦-n-羧酸酐及其制备和应用 |
| EP3288381A1 (en) | 2015-04-27 | 2018-03-07 | Bayer CropScience Aktiengesellschaft | Herbicide combinations comprising glufosinate and indaziflam |
| US10611785B2 (en) | 2015-09-02 | 2020-04-07 | Basf Se | Process for producing phosphorus-containing cyanohydrin esters |
| CN108026122B (zh) | 2015-09-02 | 2021-03-09 | 拜耳作物科学股份公司 | 制备含磷氰醇酯的方法 |
| CN108137628B (zh) | 2015-09-02 | 2020-10-09 | 拜耳农作物科学股份公司 | 制备含磷的氰醇酯的方法 |
| US10196410B2 (en) | 2015-09-02 | 2019-02-05 | Bayer Cropscience Aktiengesellschaft | Process for producing phosphorus-containing cyanohydrin esters |
| TWI721019B (zh) | 2015-09-29 | 2021-03-11 | 德商拜耳作物科學股份有限公司 | 製造膦酸酯之方法 |
| CN107236001A (zh) * | 2016-04-06 | 2017-10-10 | 四川省乐山市福华通达农药科技有限公司 | 一种膦醛的合成方法 |
| CN107417721B (zh) * | 2016-05-24 | 2019-05-28 | 四川福思达生物技术开发有限责任公司 | 一种氢氰酸加成工艺 |
| WO2018108797A1 (de) | 2016-12-15 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Verfahren zur herstellung von l-glufosinat oder dessen salzen unter verwendung von ephedrin |
| WO2018108794A1 (de) | 2016-12-15 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Verfahren zur herstellung von d-glufosinat oder dessen salzen unter verwendung von ephedrin |
| EP3392237B1 (de) | 2017-04-21 | 2019-10-02 | Evonik Degussa GmbH | Verfahren zur herstellung von acroleincyanhydrinen |
| CN111065270A (zh) * | 2017-07-18 | 2020-04-24 | 阿格里麦蒂斯有限责任公司 | L-草胺膦的生产方法 |
| KR102644410B1 (ko) | 2017-07-21 | 2024-03-06 | 바스프 에스이 | N-부틸(3-아미노-3-시아노프로필)메틸포스피네이트 및 (3-아미노-3-시아노프로필)메틸포스핀산 암모늄 염의 혼합물을 제공하기 위한 3-[n-부톡시(메틸)포스포릴]-1-시아노프로필 아세테이트의 반응에 의한 글루포시네이트의 제조 |
| US11220520B2 (en) | 2017-12-19 | 2022-01-11 | Basf Se | Method for preparing phosphorus-containing α-aminonitriles |
| CN109134534B (zh) * | 2018-08-08 | 2020-09-08 | 江苏好收成韦恩农化股份有限公司 | 一种3,3-二烷氧基丙基甲基膦酸酯简易制备方法 |
| KR102131687B1 (ko) * | 2018-09-10 | 2020-07-08 | 주식회사 휴런 | 파킨슨 병 진단 장치 및 방법 |
| CN111662326B (zh) * | 2019-03-05 | 2023-03-24 | 利尔化学股份有限公司 | 一种制备l-草铵膦的方法 |
| CN111662325B (zh) * | 2019-03-05 | 2023-03-24 | 利尔化学股份有限公司 | 一种制备l-草铵膦的方法 |
| CN111662324B (zh) * | 2019-03-05 | 2023-02-24 | 利尔化学股份有限公司 | 一种制备l-草铵膦的方法 |
| CN110003269B (zh) * | 2019-04-29 | 2022-04-05 | 利尔化学股份有限公司 | 低能耗生产草铵膦的方法 |
| CN110590836B (zh) * | 2019-09-30 | 2022-07-26 | 江苏七洲绿色化工股份有限公司 | 一种草铵膦中间体的合成方法 |
| CN112898338A (zh) * | 2019-12-04 | 2021-06-04 | 利尔化学股份有限公司 | 草铵膦中间体及草铵膦的制备方法 |
| CN111659330B (zh) * | 2020-04-23 | 2021-05-07 | 河北威远生物化工有限公司 | 一种连续化生产草铵膦的工艺与设备 |
| CN112358499A (zh) * | 2020-11-12 | 2021-02-12 | 江苏春江润田农化有限公司 | 一种草铵膦的合成方法 |
| PE20241062A1 (es) | 2021-04-01 | 2024-05-13 | Evonik Operations Gmbh | Procedimiento enzimatico para la produccion de l-glufosinato y sus fosfoesteres |
| EP4105335A1 (en) | 2021-06-16 | 2022-12-21 | Evonik Operations GmbH | Enzymatic method for the production of l-glufosinate p-alkyl esters |
| HUE068217T2 (hu) * | 2021-07-20 | 2024-12-28 | Lier Chemical Co Ltd | Glufozinát vagy analógjának elõállítására szolgáló eljárás |
| EP4151643A1 (en) | 2021-09-16 | 2023-03-22 | Evonik Operations GmbH | Improved process for production of phosphoesters of glufosinate precursors |
| CN114163472B (zh) * | 2021-11-27 | 2024-08-09 | 永农生物科学有限公司 | 醇溶剂下合成α-氨基腈的方法及草铵膦的合成方法 |
| WO2023174511A1 (en) | 2022-03-14 | 2023-09-21 | Evonik Operations Gmbh | Enzymatic method for the production of l-glufosinate p-esters |
| CN116789695B (zh) * | 2022-11-17 | 2024-03-29 | 永农生物科学有限公司 | 一种草铵膦的制备方法 |
| WO2024175643A1 (en) | 2023-02-23 | 2024-08-29 | Basf Se | A process for preparing l-glufosinate from cyanhydrine or cyanhydrine derivatives |
| WO2024256370A1 (en) | 2023-06-13 | 2024-12-19 | Basf Se | Synthesis of glufosinate using an amidase-based process |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0009022A1 (en) * | 1977-12-19 | 1980-03-19 | Meiji Seika Kaisha Ltd. | Processes for preparing D,L-2-amino-4((hydroxy)(methyl)phosphinoyl)-butyric acid and an acetal of an ester of 3-oxopropylmethyl phosphinic acid |
| US4521348A (en) * | 1978-11-11 | 1985-06-04 | Hoechst Aktiengesellschaft | Phosphorus-containing cyanohydrine derivatives |
| DE3508573A1 (de) * | 1985-03-11 | 1986-09-11 | Hoechst Ag, 6230 Frankfurt | Phosphorhaltige (alpha)-aminonitrile und verfahren zu ihrer herstellung |
| EP0292918A1 (en) * | 1987-05-26 | 1988-11-30 | Nissan Chemical Industries Ltd. | Process for producing phosphinylamino acid derivatives |
| RU2024536C1 (ru) * | 1992-01-09 | 1994-12-15 | Институт элементоорганических соединений РАН | 4-триметилсилоксиметилфосфинил -2- триметилсилокси -2-бутеннитрил в качестве полупродукта синтеза 4-метилгидроксифосфинил-2- кетобутановой кислоты, обладающей гербицидной активностью, и способы его получения |
-
1997
- 1997-08-20 DE DE19736125A patent/DE19736125A1/de not_active Withdrawn
-
1998
- 1998-08-08 PL PL338855A patent/PL191587B1/pl not_active IP Right Cessation
- 1998-08-08 WO PCT/EP1998/005053 patent/WO1999009039A1/de not_active Ceased
- 1998-08-08 BR BRPI9811971-0A patent/BR9811971B1/pt not_active IP Right Cessation
- 1998-08-08 AT AT98945195T patent/ATE258180T1/de not_active IP Right Cessation
- 1998-08-08 US US09/486,031 patent/US6359162B1/en not_active Expired - Lifetime
- 1998-08-08 EP EP98945195A patent/EP1005475B1/de not_active Expired - Lifetime
- 1998-08-08 CN CNB988082616A patent/CN1261442C/zh not_active Expired - Lifetime
- 1998-08-08 JP JP2000509718A patent/JP4519316B2/ja not_active Expired - Lifetime
- 1998-08-08 CZ CZ2000593A patent/CZ2000593A3/cs unknown
- 1998-08-08 ES ES98945195T patent/ES2214727T3/es not_active Expired - Lifetime
- 1998-08-08 DK DK98945195T patent/DK1005475T3/da active
- 1998-08-08 AU AU92598/98A patent/AU756471B2/en not_active Ceased
- 1998-08-08 PT PT98945195T patent/PT1005475E/pt unknown
- 1998-08-08 RU RU2000107139/04A patent/RU2275376C2/ru not_active IP Right Cessation
- 1998-08-08 CA CA002301181A patent/CA2301181C/en not_active Expired - Fee Related
- 1998-08-08 IL IL13463398A patent/IL134633A0/xx not_active IP Right Cessation
- 1998-08-08 DE DE59810636T patent/DE59810636D1/de not_active Expired - Lifetime
- 1998-08-08 HU HU0003501A patent/HUP0003501A3/hu unknown
- 1998-08-08 UA UA2000031510A patent/UA66806C2/uk unknown
- 1998-08-08 TR TR2000/00456T patent/TR200000456T2/xx unknown
- 1998-08-08 KR KR1020007001687A patent/KR100674326B1/ko not_active Expired - Lifetime
- 1998-08-18 MY MYPI98003746A patent/MY132853A/en unknown
- 1998-08-18 CO CO98046950A patent/CO5031316A1/es unknown
- 1998-08-18 AR ARP980104072A patent/AR015932A1/es active IP Right Grant
- 1998-08-18 TW TW087113567A patent/TW530063B/zh not_active IP Right Cessation
- 1998-08-19 ZA ZA987465A patent/ZA987465B/xx unknown
- 1998-08-19 PH PH11998002119A patent/PH11998002119A1/en unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0009022A1 (en) * | 1977-12-19 | 1980-03-19 | Meiji Seika Kaisha Ltd. | Processes for preparing D,L-2-amino-4((hydroxy)(methyl)phosphinoyl)-butyric acid and an acetal of an ester of 3-oxopropylmethyl phosphinic acid |
| US4521348A (en) * | 1978-11-11 | 1985-06-04 | Hoechst Aktiengesellschaft | Phosphorus-containing cyanohydrine derivatives |
| DE3508573A1 (de) * | 1985-03-11 | 1986-09-11 | Hoechst Ag, 6230 Frankfurt | Phosphorhaltige (alpha)-aminonitrile und verfahren zu ihrer herstellung |
| EP0292918A1 (en) * | 1987-05-26 | 1988-11-30 | Nissan Chemical Industries Ltd. | Process for producing phosphinylamino acid derivatives |
| RU2024536C1 (ru) * | 1992-01-09 | 1994-12-15 | Институт элементоорганических соединений РАН | 4-триметилсилоксиметилфосфинил -2- триметилсилокси -2-бутеннитрил в качестве полупродукта синтеза 4-метилгидроксифосфинил-2- кетобутановой кислоты, обладающей гербицидной активностью, и способы его получения |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2323223C2 (ru) * | 2002-03-21 | 2008-04-27 | Шеринг Акциенгезельшафт | Ингибиторы карбоксипептидазы b плазмы (крови) |
| RU2799336C2 (ru) * | 2019-01-11 | 2023-07-04 | СиДжей ЧеилДжеданг Корпорейшн | Способ получения промежуточного соединения L-глюфосината и L-глюфосината |
| RU2812725C2 (ru) * | 2019-01-11 | 2024-02-01 | СиДжей ЧеилДжеданг Корпорейшн | Способ получения L-глюфосината |
| US12252502B2 (en) | 2019-01-11 | 2025-03-18 | Cj Cheiljedang Corporation | L-glufosinate intermediate and L-glufosinate preparation method |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2275376C2 (ru) | Способ получения 2-амино-4-[гидрокси(метил)фосфинил]масляной кислоты | |
| SU682097A3 (ru) | Гербицидное средство | |
| US4422982A (en) | Method for preparation of N-phosphonomethylglycine | |
| US4400330A (en) | Method for preparation of N-phosphonomethylglycine | |
| ES2225764T3 (es) | Procedimiento para obtencion de acido n-fosfono-metiliminodiacetico. | |
| US4415503A (en) | Method for preparation of N-phosphonomethylglycine | |
| US4428888A (en) | Method for preparation of N-phosphonomethylglycine | |
| KR930002412B1 (ko) | N-아실-아미노메틸 포스포네이트의 제조방법 | |
| AU2002244510B2 (en) | Insecticide and method of controlling insects | |
| JPH09241284A (ja) | 新規なオキシアザホスホリン誘導体 | |
| WO2022264043A1 (en) | One pot process for preparation of a chiral amino acid | |
| MXPA00001773A (en) | Method for producing glufosinates and intermediate products for the same | |
| CA1228596A (en) | Method for preparation of n-phosphonomethylglycine or salts | |
| US5591861A (en) | Optically active ω-halo-2-amino-alkanecarboxylic acid derivatives, process for the preparation thereof and their use for the preparation of optically active phosphorus-containing α-amino acids | |
| EP0207690A1 (en) | N-Substituted glutamic acid derivative and process for production and use thereof | |
| SU1662997A1 (ru) | Бутиловый эфир этил-1-(фениламино)циклогексилфосфиновой кислоты, про вл ющий гербицидную активность |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD4A | Correction of name of patent owner | ||
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20090809 |