NO841910L - Fremgangsmaate for fremstilling av n-fosfonometylglycin - Google Patents
Fremgangsmaate for fremstilling av n-fosfonometylglycinInfo
- Publication number
- NO841910L NO841910L NO841910A NO841910A NO841910L NO 841910 L NO841910 L NO 841910L NO 841910 A NO841910 A NO 841910A NO 841910 A NO841910 A NO 841910A NO 841910 L NO841910 L NO 841910L
- Authority
- NO
- Norway
- Prior art keywords
- acid
- npmg
- salt
- iminourea
- npmida
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 45
- 238000002360 preparation method Methods 0.000 title claims description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 51
- 239000002253 acid Substances 0.000 claims description 43
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 38
- FDQQNNZKEJIHMS-UHFFFAOYSA-N 3,4,5-trimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1C FDQQNNZKEJIHMS-UHFFFAOYSA-N 0.000 claims description 35
- 238000007254 oxidation reaction Methods 0.000 claims description 31
- 229960004198 guanidine Drugs 0.000 claims description 30
- 230000003647 oxidation Effects 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 13
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 12
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 8
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910001882 dioxygen Inorganic materials 0.000 claims description 5
- 229910052736 halogen Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 claims description 4
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 60
- 235000002639 sodium chloride Nutrition 0.000 description 32
- 239000000047 product Substances 0.000 description 19
- -1 aminophosphine compound Chemical class 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 14
- 239000001301 oxygen Substances 0.000 description 14
- 229910052760 oxygen Inorganic materials 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000006227 byproduct Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- SSOCDAQSBVOZDA-UHFFFAOYSA-N iminourea;hydrochloride Chemical compound Cl.NC(=O)N=N SSOCDAQSBVOZDA-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 239000004009 herbicide Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- SGVDYFNFBJGOHB-UHFFFAOYSA-N 2-[methyl(phosphonomethyl)amino]acetic acid Chemical compound OC(=O)CN(C)CP(O)(O)=O SGVDYFNFBJGOHB-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- 238000006485 reductive methylation reaction Methods 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 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
- 238000006547 Leuckart Thiophenol synthesis reaction Methods 0.000 description 2
- AZIHIQIVLANVKD-UHFFFAOYSA-N N-(phosphonomethyl)iminodiacetic acid Chemical class OC(=O)CN(CC(O)=O)CP(O)(O)=O AZIHIQIVLANVKD-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- OEQIWRPSYDTREZ-UHFFFAOYSA-N formaldehyde;iminourea Chemical class O=C.NC(=O)N=N OEQIWRPSYDTREZ-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000002357 guanidines Chemical class 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical class OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 2
- HSMRCPIZVMDSHN-UHFFFAOYSA-N methylaminomethylphosphonic acid Chemical compound CNCP(O)(O)=O HSMRCPIZVMDSHN-UHFFFAOYSA-N 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AYRCKUXVQHNYRW-UHFFFAOYSA-N 1,1,2-triethylguanidine Chemical compound CCN=C(N)N(CC)CC AYRCKUXVQHNYRW-UHFFFAOYSA-N 0.000 description 1
- NQOFYFRKWDXGJP-UHFFFAOYSA-N 1,1,2-trimethylguanidine Chemical compound CN=C(N)N(C)C NQOFYFRKWDXGJP-UHFFFAOYSA-N 0.000 description 1
- FXQVBOJLSKRNLL-UHFFFAOYSA-N 1,2-bis(4-methylphenyl)guanidine Chemical compound C1=CC(C)=CC=C1NC(N)=NC1=CC=C(C)C=C1 FXQVBOJLSKRNLL-UHFFFAOYSA-N 0.000 description 1
- JGGFDEJXWLAQKR-UHFFFAOYSA-N 1,2-diaminoguanidine Chemical compound NNC(N)=NN JGGFDEJXWLAQKR-UHFFFAOYSA-N 0.000 description 1
- MCMBEBOHGREEOP-UHFFFAOYSA-N 1,2-diethylguanidine Chemical compound CCNC(=N)NCC MCMBEBOHGREEOP-UHFFFAOYSA-N 0.000 description 1
- LINDOXZENKYESA-UHFFFAOYSA-N 1,2-dimethylguanidine Chemical compound CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 1
- ATMCYVLYKYHSJF-UHFFFAOYSA-N 2-(phosphonomethylimino)acetic acid Chemical compound OC(=O)C=NCP(O)(O)=O ATMCYVLYKYHSJF-UHFFFAOYSA-N 0.000 description 1
- KEWLVUBYGUZFKX-UHFFFAOYSA-N 2-ethylguanidine Chemical compound CCNC(N)=N KEWLVUBYGUZFKX-UHFFFAOYSA-N 0.000 description 1
- KMMKKNKMHUQJAW-UHFFFAOYSA-N 2-methylaminoethylphosphonic acid Chemical compound CNCCP(O)(O)=O KMMKKNKMHUQJAW-UHFFFAOYSA-N 0.000 description 1
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 238000006824 Eschweiler-Clarke methylation reaction Methods 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 238000004364 calculation method Methods 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
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- QYXHJMXBZWOTJN-UHFFFAOYSA-N formaldehyde;guanidine Chemical compound O=C.NC(N)=N QYXHJMXBZWOTJN-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960002523 mercuric chloride Drugs 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000003007 phosphonic acid derivatives Chemical class 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 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
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)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL68716A IL68716A (en) | 1983-05-17 | 1983-05-17 | Process for producing n-phosphonomethylglycine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO841910L true NO841910L (no) | 1984-11-19 |
Family
ID=11054267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO841910A NO841910L (no) | 1983-05-17 | 1984-05-11 | Fremgangsmaate for fremstilling av n-fosfonometylglycin |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4507250A (ja) |
| EP (1) | EP0125363A1 (ja) |
| JP (1) | JPS59219298A (ja) |
| KR (1) | KR840009313A (ja) |
| AU (1) | AU559641B2 (ja) |
| BR (1) | BR8402458A (ja) |
| CS (1) | CS244136B2 (ja) |
| DK (1) | DK225184A (ja) |
| ES (1) | ES8507320A1 (ja) |
| FI (1) | FI841813A (ja) |
| GR (1) | GR79865B (ja) |
| HU (1) | HUT34758A (ja) |
| IL (1) | IL68716A (ja) |
| MX (1) | MX158086A (ja) |
| NO (1) | NO841910L (ja) |
| PL (1) | PL247721A1 (ja) |
| PT (1) | PT78589B (ja) |
| ZA (1) | ZA843503B (ja) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4579689A (en) * | 1985-02-11 | 1986-04-01 | Monsanto Company | Oxidation with coated catalyst |
| US4582650A (en) * | 1985-02-11 | 1986-04-15 | Monsanto Company | Oxidation with encapsulated co-catalyst |
| US4696772A (en) * | 1985-02-28 | 1987-09-29 | Monsanto Company | Amine oxidation using carbon catalyst having oxides removed from surface |
| US5580841A (en) * | 1985-05-29 | 1996-12-03 | Zeneca Limited | Solid, phytoactive compositions and method for their preparation |
| US5468718A (en) * | 1985-10-21 | 1995-11-21 | Ici Americas Inc. | Liquid, phytoactive compositions and method for their preparation |
| US5047079A (en) * | 1986-08-18 | 1991-09-10 | Ici Americas Inc. | Method of preparation and use of solid, phytoactive compositions |
| US4853159A (en) * | 1987-10-26 | 1989-08-01 | Monsanto Company | Process for producing N-phosphonomethylglycine |
| NZ231897A (en) | 1988-12-30 | 1992-09-25 | Monsanto Co | Dry water-soluble granular composition comprising glyphosate and a liquid surfactant |
| US5023369A (en) * | 1990-06-25 | 1991-06-11 | Monsanto Company | Process for producing N-phosphonomethylglycine |
| IL101539A (en) | 1991-04-16 | 1998-09-24 | Monsanto Europe Sa | Mono-ammonium salts of the history of N phosphonomethyl glycyl which are not hygroscopes, their preparations and pesticides containing |
| DE19500121A1 (de) * | 1995-01-04 | 1996-07-11 | Bayer Ag | Verfahren zur Herstellung von N-Phosphonomethylglycin |
| NZ502397A (en) * | 1997-07-22 | 2002-04-26 | Monsanto Co | Storage stable high-loaded ammonium glyphosate and surfactant formulations |
| NZ502499A (en) * | 1997-07-30 | 2001-11-30 | Monsanto Co | Herbicide consisting of glyphosate composition and polyamine derivatives |
| ITTO980048A1 (it) * | 1998-01-20 | 1999-07-20 | Ipici Spa | Composizioni erbicide, procedimenti per la loro preparazione ed impieghi |
| EP1062221B1 (en) * | 1998-02-12 | 2006-05-10 | Monsanto Technology LLC | Process for making glyphosate by oxidizing n-substituted glyphosates |
| US6232494B1 (en) | 1998-02-12 | 2001-05-15 | Monsanto Company | Process for the preparation of N-(phosphonomethyl)glycine by oxidizing N-substituted N-(phosphonomethyl)glycine |
| WO1999040785A1 (en) * | 1998-02-13 | 1999-08-19 | Monsanto Company | Storage-stable composition containing exogenous chemical substance and siloxane surfactant |
| US6417133B1 (en) | 1998-02-25 | 2002-07-09 | Monsanto Technology Llc | Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions |
| GB9819693D0 (en) | 1998-09-10 | 1998-11-04 | Zeneca Ltd | Glyphosate formulation |
| NZ511853A (en) | 1998-11-23 | 2003-12-19 | Monsanto Co | Compact storage and shipping system for glyphosate herbicide |
| DE69920035T2 (de) | 1998-11-23 | 2005-09-15 | Monsanto Technology Llc. | Hochkonzentrierte wässrige glyphosatzusammensetzungen |
| EP1135024B1 (en) | 1998-11-30 | 2004-12-29 | Flamel Technologies | Promoting biological effectiveness of exogenous chemical substances in plants |
| US6369001B1 (en) | 1999-08-11 | 2002-04-09 | Monsanto Technology, Llc | Microemulsion coformulation of a graminicide and a water-soluble herbicide |
| US6746976B1 (en) | 1999-09-24 | 2004-06-08 | The Procter & Gamble Company | Thin until wet structures for acquiring aqueous fluids |
| JP5433120B2 (ja) | 1999-09-30 | 2014-03-05 | モンサント テクノロジー エルエルシー | 向上した安定性を有するパッケージミックス農薬組成物 |
| US7135437B2 (en) | 2000-05-19 | 2006-11-14 | Monsanto Technology Llc | Stable liquid pesticide compositions |
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| US6992045B2 (en) | 2000-05-19 | 2006-01-31 | Monsanto Technology Llc | Pesticide compositions containing oxalic acid |
| US7015351B2 (en) * | 2000-05-22 | 2006-03-21 | Monsanto Technology Llc | Reaction systems for making N-(phosphonomethyl) glycine compounds |
| US6300323B1 (en) | 2000-08-08 | 2001-10-09 | Ishihara Sangyo Kaisha, Ltd. | (Poly)ethereal ammonium salts of herbicides bearing acidic moieties and their use as herbicides |
| US6921834B2 (en) | 2002-05-22 | 2005-07-26 | Dow Agrosciences Llc | Continuous process for preparing N-phosphonomethyl glycine |
| US20050037924A1 (en) * | 2002-08-31 | 2005-02-17 | Monsanto Technology Llc | Sodium glyphosate compositions and process for their preparation |
| WO2004019684A2 (en) * | 2002-08-31 | 2004-03-11 | Monsanto Technology Llc | Process for the preparation of a dry pesticidal composition containing a dicarbodylate component |
| AR037559A1 (es) * | 2002-11-19 | 2004-11-17 | Atanor S A | Una formulacion herbicida solida de n-fosfonometilglicina, bajo la forma de polvo, granulos o escamas, soluble o dispersable en agua, y el procedimiento para preparar dicha composicion |
| WO2006031938A2 (en) * | 2004-09-15 | 2006-03-23 | Monsanto Technology Llc | Oxidation catalyst and its use for catalyzing liquid phase oxidation reactions |
| US7223718B2 (en) * | 2005-03-07 | 2007-05-29 | Falcon Lab Llc | Enhanced glyphosate herbicidal concentrates |
| US20070049498A1 (en) * | 2005-09-01 | 2007-03-01 | Brigance Mickey R | Agricultural compositions which enhance performance of herbicides |
| US8252953B2 (en) | 2008-05-01 | 2012-08-28 | Monsanto Technology Llc | Metal utilization in supported, metal-containing catalysts |
| BRPI0914226B1 (pt) * | 2008-06-18 | 2021-01-19 | Stepan Company | concentrado contendo sal de glifosato de carga ultra alta, método para fabricação do mesmo e método para controlar vegetação indesejada |
| PL2337452T3 (pl) | 2008-07-03 | 2015-05-29 | Monsanto Technology Llc | Połączenia derywatyzowanych sacharydowych środków powierzchniowo czynnych i środków powierzchniowo czynnych stanowiących tlenek eteroaminy jako adiuwanty do herbicydów |
| AR074976A1 (es) * | 2008-09-29 | 2011-03-02 | Monsanto Technology Llc | Formulaciones de glifosfato que contienen agentes tensioactivos de amidoalquilaminas |
| CA2766374C (en) | 2009-06-30 | 2017-10-03 | Monsanto Technology Llc | N-phosphonomethylglycine guanidine derivative salts |
| US20110071027A1 (en) * | 2009-09-18 | 2011-03-24 | Volker Heide | High strength aqueous glyphosate salt concentrates and methods |
| JP5529831B2 (ja) * | 2010-12-22 | 2014-06-25 | ダウ グローバル テクノロジーズ エルエルシー | グリホサート化合物とｉｐｂｃとの相乗的組み合わせ |
| CN109310095A (zh) | 2016-05-11 | 2019-02-05 | 孟山都技术公司 | 含酰胺基烷基胺表面活性剂的草甘膦制剂 |
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| EP3628160A1 (en) | 2018-09-25 | 2020-04-01 | KWS SAAT SE & Co. KGaA | Use of glyphosate herbicide for controlling unwanted vegetation in beta vulgaris growing areas |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3954848A (en) * | 1972-05-31 | 1976-05-04 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
| US3950402A (en) * | 1972-05-31 | 1976-04-13 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
| US3969398A (en) * | 1974-05-01 | 1976-07-13 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
| US3907652A (en) * | 1974-10-30 | 1975-09-23 | Monsanto Co | Electrooxidation of phosphonomethyl amines |
| MX4703E (es) * | 1976-12-20 | 1982-08-04 | Monsanto Co | Procedimiento mejorado para la preparacion de mono y disales de n-fosfonometilglicina |
| HU184168B (en) * | 1979-05-11 | 1984-07-30 | Mta Koezponti Kemiai Kutato In | Process for producing n-bracket-phosphono-methyl-bracket closed-glycine |
| IL65187A (en) * | 1982-03-08 | 1985-03-31 | Geshuri Lab Ltd | N-phosphonomethylglycine derivatives,processes for their preparation and herbicidal compositions containing them |
| IL66824A0 (en) * | 1982-06-25 | 1982-12-31 | Geshuri Lab Ltd | Process for producing n-phosphonomethylglycine derivatives and herbicidal compounds and compositions prepared thereby |
-
1983
- 1983-05-17 IL IL68716A patent/IL68716A/xx unknown
- 1983-08-04 EP EP83304517A patent/EP0125363A1/en not_active Withdrawn
-
1984
- 1984-05-07 FI FI841813A patent/FI841813A/fi not_active Application Discontinuation
- 1984-05-07 DK DK225184A patent/DK225184A/da not_active Application Discontinuation
- 1984-05-09 AU AU27818/84A patent/AU559641B2/en not_active Ceased
- 1984-05-09 ZA ZA843503A patent/ZA843503B/xx unknown
- 1984-05-09 GR GR74661A patent/GR79865B/el unknown
- 1984-05-11 HU HU841849A patent/HUT34758A/hu unknown
- 1984-05-11 CS CS843509A patent/CS244136B2/cs unknown
- 1984-05-11 US US06/609,213 patent/US4507250A/en not_active Expired - Fee Related
- 1984-05-11 NO NO841910A patent/NO841910L/no unknown
- 1984-05-12 ES ES532472A patent/ES8507320A1/es not_active Expired
- 1984-05-16 PT PT78589A patent/PT78589B/pt unknown
- 1984-05-16 KR KR1019840002652A patent/KR840009313A/ko not_active Application Discontinuation
- 1984-05-17 BR BR8402458A patent/BR8402458A/pt unknown
- 1984-05-17 JP JP59100363A patent/JPS59219298A/ja active Pending
- 1984-05-17 MX MX8003A patent/MX158086A/es unknown
- 1984-05-17 PL PL24772184A patent/PL247721A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL247721A1 (en) | 1985-03-26 |
| US4507250A (en) | 1985-03-26 |
| EP0125363A1 (en) | 1984-11-21 |
| FI841813A0 (fi) | 1984-05-07 |
| CS244136B2 (en) | 1986-07-17 |
| PT78589A (en) | 1984-06-01 |
| ES532472A0 (es) | 1985-10-01 |
| GR79865B (ja) | 1984-10-31 |
| CS350984A2 (en) | 1985-08-15 |
| AU2781884A (en) | 1984-11-22 |
| KR840009313A (ko) | 1984-12-26 |
| BR8402458A (pt) | 1985-04-02 |
| ES8507320A1 (es) | 1985-10-01 |
| IL68716A (en) | 1987-03-31 |
| DK225184D0 (da) | 1984-05-07 |
| PT78589B (en) | 1986-06-26 |
| HUT34758A (en) | 1985-04-28 |
| IL68716A0 (en) | 1983-09-30 |
| DK225184A (da) | 1984-11-18 |
| AU559641B2 (en) | 1987-03-19 |
| JPS59219298A (ja) | 1984-12-10 |
| FI841813A (fi) | 1984-11-18 |
| MX158086A (es) | 1989-01-06 |
| ZA843503B (en) | 1985-02-27 |
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