IL94496A - Process for the production of -N phosphonomethylglycine - Google Patents

Process for the production of -N phosphonomethylglycine

Info

Publication number: IL94496A
Authority: IL; Israel
Prior art keywords: guinone; quinone; catalyst; molar; concentration
Prior art date: 1989-05-25

Application number

IL9449690A

Other languages

English (en)

Hebrew (he)

Other versions

IL94496A0 (en

Original Assignee

Monsanto Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-05-25

Filing date

1990-05-24

Publication date

1994-05-30

1990-05-24 Application filed by Monsanto Co filed Critical Monsanto Co

1991-03-10 Publication of IL94496A0 publication Critical patent/IL94496A0/xx

1994-05-30 Publication of IL94496A publication Critical patent/IL94496A/en

Links

238000000034 method Methods 0.000 title claims abstract description 42
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims abstract description 25
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims abstract description 39
AZIHIQIVLANVKD-UHFFFAOYSA-N N-(phosphonomethyl)iminodiacetic acid Chemical compound OC(=O)CN(CC(O)=O)CP(O)(O)=O AZIHIQIVLANVKD-UHFFFAOYSA-N 0.000 claims abstract description 30
150000003839 salts Chemical class 0.000 claims abstract description 30
239000003054 catalyst Substances 0.000 claims abstract description 23
239000007789 gas Substances 0.000 claims abstract description 18
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 14
229910001882 dioxygen Inorganic materials 0.000 claims abstract description 14
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 12
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 10
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 10
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 9
229910017052 cobalt Inorganic materials 0.000 claims abstract description 8
239000010941 cobalt Substances 0.000 claims abstract description 8
229910052684 Cerium Inorganic materials 0.000 claims abstract description 7
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims abstract description 7
238000004519 manufacturing process Methods 0.000 claims abstract description 7
229910052720 vanadium Inorganic materials 0.000 claims abstract description 7
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 5
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052782 aluminium Inorganic materials 0.000 claims abstract description 5
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052804 chromium Inorganic materials 0.000 claims abstract description 5
239000011651 chromium Substances 0.000 claims abstract description 5
229910052742 iron Inorganic materials 0.000 claims abstract description 5
229910052759 nickel Inorganic materials 0.000 claims abstract description 5
229910052707 ruthenium Inorganic materials 0.000 claims abstract description 5
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims abstract 4
GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims abstract 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 claims description 9
-1 hydroxy, carboxy, amino Chemical group 0.000 claims description 7
229910052751 metal Inorganic materials 0.000 claims description 7
239000002184 metal Substances 0.000 claims description 7
239000002002 slurry Substances 0.000 claims description 6
150000004059 quinone derivatives Chemical class 0.000 claims description 5
229910021645 metal ion Inorganic materials 0.000 claims description 4
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
ATMCYVLYKYHSJF-UHFFFAOYSA-N 2-(phosphonomethylimino)acetic acid Chemical compound OC(=O)C=NCP(O)(O)=O ATMCYVLYKYHSJF-UHFFFAOYSA-N 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 2
239000012429 reaction media Substances 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims 2
229910052739 hydrogen Inorganic materials 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract description 3
229910052750 molybdenum Inorganic materials 0.000 abstract description 3
239000011733 molybdenum Substances 0.000 abstract description 3
238000006243 chemical reaction Methods 0.000 description 34
150000004056 anthraquinones Chemical class 0.000 description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
239000001301 oxygen Substances 0.000 description 11
229910052760 oxygen Inorganic materials 0.000 description 11
238000007254 oxidation reaction Methods 0.000 description 10
239000000243 solution Substances 0.000 description 9
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 7
230000003647 oxidation Effects 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 5
229960004337 hydroquinone Drugs 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 4
241000196324 Embryophyta Species 0.000 description 3
238000013019 agitation Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
150000004053 quinones Chemical class 0.000 description 3
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
229940076442 9,10-anthraquinone Drugs 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000003125 aqueous solvent Substances 0.000 description 2
150000004054 benzoquinones Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
HZGMNNQOPOLCIG-UHFFFAOYSA-N chrysene-5,6-dione Chemical compound C12=CC=CC=C2C(=O)C(=O)C2=C1C=CC1=CC=CC=C21 HZGMNNQOPOLCIG-UHFFFAOYSA-N 0.000 description 2
229940044175 cobalt sulfate Drugs 0.000 description 2
229910000361 cobalt sulfate Inorganic materials 0.000 description 2
KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000002815 homogeneous catalyst Substances 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
229910000510 noble metal Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 description 1
KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 1
229940105324 1,2-naphthoquinone Drugs 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
CVBKKNGZEKPPGO-UHFFFAOYSA-N 2-[carboxymethyl(phosphono)amino]acetic acid Chemical compound OC(=O)CN(P(O)(O)=O)CC(O)=O CVBKKNGZEKPPGO-UHFFFAOYSA-N 0.000 description 1
WPYWLOUBBQYLCD-UHFFFAOYSA-N 2-[formyl(phosphonomethyl)amino]acetic acid Chemical compound OC(=O)CN(C=O)CP(O)(O)=O WPYWLOUBBQYLCD-UHFFFAOYSA-N 0.000 description 1
QJICNAUCGTWDHE-UHFFFAOYSA-N 2-[methyl(phosphono)amino]acetic acid Chemical compound OP(=O)(O)N(C)CC(O)=O QJICNAUCGTWDHE-UHFFFAOYSA-N 0.000 description 1
JEGXLJDYOKKUNM-UHFFFAOYSA-N 3-(2-phenylethenyl)cyclohexa-3,5-diene-1,2-dione Chemical class O=C1C(=O)C=CC=C1C=CC1=CC=CC=C1 JEGXLJDYOKKUNM-UHFFFAOYSA-N 0.000 description 1
FPFSGDXIBUDDKZ-UHFFFAOYSA-N 3-decyl-2-hydroxycyclopent-2-en-1-one Chemical compound CCCCCCCCCCC1=C(O)C(=O)CC1 FPFSGDXIBUDDKZ-UHFFFAOYSA-N 0.000 description 1
PCFMUWBCZZUMRX-UHFFFAOYSA-N 9,10-Dihydroxyanthracene Chemical compound C1=CC=C2C(O)=C(C=CC=C3)C3=C(O)C2=C1 PCFMUWBCZZUMRX-UHFFFAOYSA-N 0.000 description 1
RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
150000004058 9,10-anthraquinones Chemical class 0.000 description 1
YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical class C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229910021555 Chromium Chloride Inorganic materials 0.000 description 1
239000005562 Glyphosate Substances 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
108010077895 Sarcosine Proteins 0.000 description 1
229910021550 Vanadium Chloride Inorganic materials 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
239000003570 air Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
RGHILYZRVFRRNK-UHFFFAOYSA-N anthracene-1,2-dione Chemical class C1=CC=C2C=C(C(C(=O)C=C3)=O)C3=CC2=C1 RGHILYZRVFRRNK-UHFFFAOYSA-N 0.000 description 1
239000013011 aqueous formulation Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000012431 aqueous reaction media Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
LHMRXAIRPKSGDE-UHFFFAOYSA-N benzo[a]anthracene-7,12-dione Chemical compound C1=CC2=CC=CC=C2C2=C1C(=O)C1=CC=CC=C1C2=O LHMRXAIRPKSGDE-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
XVQUFOXACWQJMY-UHFFFAOYSA-N chrysene-6,12-dione Chemical compound C1=CC=C2C(=O)C=C3C4=CC=CC=C4C(=O)C=C3C2=C1 XVQUFOXACWQJMY-UHFFFAOYSA-N 0.000 description 1
229940011182 cobalt acetate Drugs 0.000 description 1
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
229910001981 cobalt nitrate Inorganic materials 0.000 description 1
229910000428 cobalt oxide Inorganic materials 0.000 description 1
QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
BZRRQSJJPUGBAA-UHFFFAOYSA-L cobalt(ii) bromide Chemical compound Br[Co]Br BZRRQSJJPUGBAA-UHFFFAOYSA-L 0.000 description 1
IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
LBFUKZWYPLNNJC-UHFFFAOYSA-N cobalt(ii,iii) oxide Chemical compound [Co]=O.O=[Co]O[Co]=O LBFUKZWYPLNNJC-UHFFFAOYSA-N 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
PLXSXOUOWRGVOZ-UHFFFAOYSA-L dibromocobalt;hexahydrate Chemical compound O.O.O.O.O.O.Br[Co]Br PLXSXOUOWRGVOZ-UHFFFAOYSA-L 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000008246 gaseous mixture Substances 0.000 description 1
229940097068 glyphosate Drugs 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
239000002638 heterogeneous catalyst Substances 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
235000002908 manganese Nutrition 0.000 description 1
229940071125 manganese acetate Drugs 0.000 description 1
229940099596 manganese sulfate Drugs 0.000 description 1
235000007079 manganese sulphate Nutrition 0.000 description 1
239000011702 manganese sulphate Substances 0.000 description 1
UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
PCWMTXMBFZQDHV-UHFFFAOYSA-N naphthalene-1,4,5,8-tetrone Chemical compound O=C1C=CC(=O)C2=C1C(=O)C=CC2=O PCWMTXMBFZQDHV-UHFFFAOYSA-N 0.000 description 1
SLBHRPOLVUEFSG-UHFFFAOYSA-N naphthalene-2,6-dione Chemical compound O=C1C=CC2=CC(=O)C=CC2=C1 SLBHRPOLVUEFSG-UHFFFAOYSA-N 0.000 description 1
JJICAJDVPJCZAY-UHFFFAOYSA-N naphtho[1,2-b]phenanthrene-7,14-dione Chemical compound C1=CC=CC2=C3C(=O)C4=CC=C(C=CC=C5)C5=C4C(=O)C3=CC=C21 JJICAJDVPJCZAY-UHFFFAOYSA-N 0.000 description 1
UQPSGBZICXWIAG-UHFFFAOYSA-L nickel(2+);dibromide;trihydrate Chemical compound O.O.O.Br[Ni]Br UQPSGBZICXWIAG-UHFFFAOYSA-L 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000005429 oxyalkyl group Chemical group 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
RPESBQCJGHJMTK-UHFFFAOYSA-I pentachlorovanadium Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[V+5] RPESBQCJGHJMTK-UHFFFAOYSA-I 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
SCOAVUHOIJMIBW-UHFFFAOYSA-N phenanthrene-1,2-dione Chemical class C1=CC=C2C(C=CC(C3=O)=O)=C3C=CC2=C1 SCOAVUHOIJMIBW-UHFFFAOYSA-N 0.000 description 1
POZPGRADIOPGIR-UHFFFAOYSA-N phenanthrene-1,4-dione Chemical class C1=CC2=CC=CC=C2C2=C1C(=O)C=CC2=O POZPGRADIOPGIR-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000002468 redox effect Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
WYRXRHOISWEUST-UHFFFAOYSA-K ruthenium(3+);tribromide Chemical compound [Br-].[Br-].[Br-].[Ru+3] WYRXRHOISWEUST-UHFFFAOYSA-K 0.000 description 1
YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003681 vanadium Chemical class 0.000 description 1
VLOPEOIIELCUML-UHFFFAOYSA-L vanadium(2+);sulfate Chemical compound [V+2].[O-]S([O-])(=O)=O VLOPEOIIELCUML-UHFFFAOYSA-L 0.000 description 1
ZOYIPGHJSALYPY-UHFFFAOYSA-K vanadium(iii) bromide Chemical compound [V+3].[Br-].[Br-].[Br-] ZOYIPGHJSALYPY-UHFFFAOYSA-K 0.000 description 1
AGFASGGUHBOODX-UHFFFAOYSA-L vanadyl sulfate dihydrate Chemical compound O.O.[V+2]=O.[O-]S([O-])(=O)=O AGFASGGUHBOODX-UHFFFAOYSA-L 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)]
- C07F9/44—Amides thereof
- 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)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof
- 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)]

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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)
Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL9449690A 1989-05-25 1990-05-24 Process for the production of -N phosphonomethylglycine IL94496A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/356,484 US4937376A (en)	1989-05-25	1989-05-25	Process for producing N-phosphonomethylglycine

Publications (2)

Publication Number	Publication Date
IL94496A0 IL94496A0 (en)	1991-03-10
IL94496A true IL94496A (en)	1994-05-30

Family

ID=23401619

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9449690A IL94496A (en)	1989-05-25	1990-05-24	Process for the production of -N phosphonomethylglycine

Country Status (14)

Country	Link
US (1)	US4937376A (fr)
EP (1)	EP0399985B1 (fr)
JP (1)	JPH068306B2 (fr)
KR (1)	KR930005260B1 (fr)
AT (1)	ATE116652T1 (fr)
AU (1)	AU623011B2 (fr)
BR (1)	BR9002448A (fr)
CA (1)	CA2017504A1 (fr)
DE (1)	DE69015697T2 (fr)
HU (1)	HU209649B (fr)
IE (1)	IE901877L (fr)
IL (1)	IL94496A (fr)
NZ (1)	NZ233794A (fr)
ZA (1)	ZA904003B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5072033A (en) *	1990-12-11	1991-12-10	Monsanto Company	Process for producing N-phosphonomethylglycine
US5912391A (en) *	1997-11-17	1999-06-15	General Electric Company	Method for hydroxylating aromatic compounds
US6274760B1 (en)	2000-03-14	2001-08-14	Monsanto Co.	Preparation of formylphosphonic acid from tertiary aminomethylphosphonic acid N-oxides
US6441223B1 (en) *	2000-11-30	2002-08-27	Monsanto Technology Llc	Method of making phosphorus-containing compounds and products thereof
EP2875038A1 (fr) *	2012-07-17	2015-05-27	Straitmark Holding AG	Procédé de synthèse d'acide n-phosphonométhyliminodiacétique

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3950402A (en) *	1972-05-31	1976-04-13	Monsanto Company	Process for producing N-phosphonomethyl glycine
US3954848A (en) *	1972-05-31	1976-05-04	Monsanto Company	Process for producing N-phosphonomethyl glycine
US3969398A (en) *	1974-05-01	1976-07-13	Monsanto Company	Process for producing N-phosphonomethyl glycine
US4853159A (en) *	1987-10-26	1989-08-01	Monsanto Company	Process for producing N-phosphonomethylglycine

1989
- 1989-05-25 US US07/356,484 patent/US4937376A/en not_active Expired - Fee Related
1990
- 1990-05-21 AT AT90870076T patent/ATE116652T1/de not_active IP Right Cessation
- 1990-05-21 DE DE69015697T patent/DE69015697T2/de not_active Expired - Fee Related
- 1990-05-21 EP EP90870076A patent/EP0399985B1/fr not_active Expired - Lifetime
- 1990-05-23 ZA ZA904003A patent/ZA904003B/xx unknown
- 1990-05-24 BR BR909002448A patent/BR9002448A/pt not_active Application Discontinuation
- 1990-05-24 IL IL9449690A patent/IL94496A/en not_active IP Right Cessation
- 1990-05-24 AU AU55875/90A patent/AU623011B2/en not_active Ceased
- 1990-05-24 KR KR1019900007528A patent/KR930005260B1/ko not_active Expired - Fee Related
- 1990-05-24 NZ NZ233794A patent/NZ233794A/en unknown
- 1990-05-24 IE IE901877A patent/IE901877L/xx unknown
- 1990-05-24 JP JP2135162A patent/JPH068306B2/ja not_active Expired - Lifetime
- 1990-05-24 HU HU903183A patent/HU209649B/hu not_active IP Right Cessation
- 1990-05-24 CA CA002017504A patent/CA2017504A1/fr not_active Abandoned

Also Published As

Publication number	Publication date
EP0399985A2 (fr)	1990-11-28
NZ233794A (en)	1992-09-25
US4937376A (en)	1990-06-26
ATE116652T1 (de)	1995-01-15
JPH0320289A (ja)	1991-01-29
KR900018127A (ko)	1990-12-20
AU623011B2 (en)	1992-04-30
BR9002448A (pt)	1991-08-06
CA2017504A1 (fr)	1990-11-25
DE69015697T2 (de)	1995-06-22
IE901877L (en)	1990-11-25
ZA904003B (en)	1991-06-26
HU903183D0 (en)	1990-10-28
HUT53910A (en)	1990-12-28
EP0399985A3 (fr)	1991-05-29
JPH068306B2 (ja)	1994-02-02
KR930005260B1 (ko)	1993-06-17
IL94496A0 (en)	1991-03-10
EP0399985B1 (fr)	1995-01-04
DE69015697D1 (de)	1995-02-16
AU5587590A (en)	1990-11-29
HU209649B (en)	1994-09-28

Legal Events

Date	Code	Title	Description
1997-02-18	RH	Patent void

Publication	Publication Date	Title
US4853159A (en)	1989-08-01	Process for producing N-phosphonomethylglycine
JPH0798829B2 (ja)	1995-10-25	タングステン触媒を用いたｎ−ホスホノメチルグリシンの製造方法
EP0412074B1 (fr)	1994-12-28	Procédé pour produire la N-phosphonométhylglycine
US4898972A (en)	1990-02-06	Process for producing N-phosphonomethylglycine
EP0399985B1 (fr)	1995-01-04	Procédé pour produire la N-phosphonométhyl glycine
US5072033A (en)	1991-12-10	Process for producing N-phosphonomethylglycine
US5061820A (en)	1991-10-29	Process for producing N-phosphonomethylgylcine
HK1007144B (en)	1999-04-01	Process for producing n-phosphonomethylglycine