IL97046A - Process for the production of N-phosphonomethylglycine - Google Patents

Process for the production of N-phosphonomethylglycine

Info

Publication number: IL97046A
Authority: IL; Israel
Prior art keywords: compound; acid; amount; metabisulfite; phosphonomethyliminodiacetic acid
Prior art date: 1990-01-26

Application number

IL9704691A

Other languages

English (en)

Hebrew (he)

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.)

1990-01-26

Filing date

1991-01-25

Publication date

1995-10-31

1990-06-25 Priority claimed from US07/543,002 external-priority patent/US5047579A/en

1991-01-25 Application filed by Monsanto Co filed Critical Monsanto Co

1995-10-31 Publication of IL97046A publication Critical patent/IL97046A/en

Links

238000000034 method Methods 0.000 title claims abstract description 48
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title 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 46
-1 metabisulfite compound Chemical class 0.000 claims abstract description 31
150000002978 peroxides Chemical class 0.000 claims abstract description 24
239000005078 molybdenum compound Substances 0.000 claims abstract description 12
150000002752 molybdenum compounds Chemical class 0.000 claims abstract description 12
230000003647 oxidation Effects 0.000 claims abstract description 5
238000007254 oxidation reaction Methods 0.000 claims abstract description 5
239000000543 intermediate Substances 0.000 claims description 29
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 22
239000003054 catalyst Substances 0.000 claims description 12
230000003197 catalytic effect Effects 0.000 claims description 10
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical group [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims description 10
229940001584 sodium metabisulfite Drugs 0.000 claims description 10
235000010262 sodium metabisulphite Nutrition 0.000 claims description 10
229910052783 alkali metal Inorganic materials 0.000 claims description 5
235000018660 ammonium molybdate Nutrition 0.000 claims description 5
APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 claims description 4
239000011609 ammonium molybdate Substances 0.000 claims description 4
229940010552 ammonium molybdate Drugs 0.000 claims description 4
235000015393 sodium molybdate Nutrition 0.000 claims description 4
239000011684 sodium molybdate Substances 0.000 claims description 3
TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 claims description 2
238000002360 preparation method Methods 0.000 abstract description 5
238000006243 chemical reaction Methods 0.000 description 18
239000000243 solution Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 8
150000001875 compounds Chemical class 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
229910052750 molybdenum Inorganic materials 0.000 description 5
239000011733 molybdenum Substances 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000007789 gas Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
150000001204 N-oxides Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000002002 slurry Substances 0.000 description 3
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
239000011133 lead Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
150000002751 molybdenum Chemical class 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910052709 silver Inorganic materials 0.000 description 2
239000004332 silver Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000011135 tin Substances 0.000 description 2
229910052718 tin Inorganic materials 0.000 description 2
NPNBMYIARMQHND-UHFFFAOYSA-N 2-[ethyl(phosphono)amino]acetic acid Chemical compound C(C)N(CC(=O)O)P(=O)(O)O NPNBMYIARMQHND-UHFFFAOYSA-N 0.000 description 1
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
QWMFKVNJIYNWII-UHFFFAOYSA-N 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(Br)C=N1 QWMFKVNJIYNWII-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
241000380130 Ehrharta erecta Species 0.000 description 1
239000004471 Glycine Substances 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
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
XUFUCDNVOXXQQC-UHFFFAOYSA-L azane;hydroxy-(hydroxy(dioxo)molybdenio)oxy-dioxomolybdenum Chemical compound N.N.O[Mo](=O)(=O)O[Mo](O)(=O)=O XUFUCDNVOXXQQC-UHFFFAOYSA-L 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
PCAXGMRPPOMODZ-UHFFFAOYSA-N disulfurous acid, diammonium salt Chemical compound [NH4+].[NH4+].[O-]S(=O)S([O-])(=O)=O PCAXGMRPPOMODZ-UHFFFAOYSA-N 0.000 description 1
229940097068 glyphosate Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 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
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 description 1
239000000463 material Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
239000003863 metallic catalyst Substances 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
229940043349 potassium metabisulfite Drugs 0.000 description 1
235000010263 potassium metabisulphite Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
150000004685 tetrahydrates Chemical class 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)]
- C07F9/3804—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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

IL9704691A 1990-01-26 1991-01-25 Process for the production of N-phosphonomethylglycine IL97046A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
AUPJ833990		1990-01-26
US07/543,002 US5047579A (en)	1990-01-26	1990-06-25	Process for producing n-phosphonomethylglycine

Publications (1)

Publication Number	Publication Date
IL97046A true IL97046A (en)	1995-10-31

Family

ID=25643807

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9704691A IL97046A (en)	1990-01-26	1991-01-25	Process for the production of N-phosphonomethylglycine

Country Status (12)

Country	Link
EP (1)	EP0439445B1 (de)
JP (1)	JPH0692425B2 (de)
AT (1)	ATE126519T1 (de)
CA (1)	CA2034901C (de)
DE (1)	DE69112088T2 (de)
DK (1)	DK0439445T3 (de)
ES (1)	ES2027199T3 (de)
HU (1)	HU208700B (de)
IE (1)	IE74198B1 (de)
IL (1)	IL97046A (de)
MY (1)	MY104616A (de)
NZ (1)	NZ236894A (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5023369A (en) *	1990-06-25	1991-06-11	Monsanto Company	Process for producing N-phosphonomethylglycine
MXPA02001049A (es) *	1999-08-11	2002-08-20	Basf Ag	Procedimiento para preparar fosfonometilglicina.
AU6837300A (en) *	1999-08-11	2001-03-13	Basf Aktiengesellschaft	Method for the production of phosphonomethylglycine
US7390920B2 (en)	2002-02-14	2008-06-24	Monsanto Technology Llc	Oxidation catalyst and process
BRPI0413586A (pt)	2003-08-14	2006-10-17	Monsanto Technology Llc	catalisadores contendo metal de transição e processo para a preparação dos mesmos e uso como catalisadores de oxidação e de desidrogenação
BRPI0608355B1 (pt)	2005-02-17	2016-05-24	Monsanto Technology Llc	processo para oxidação de ácido n-(fosfonometil) iminodiacético ou seu sal e catalisador de oxidação

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3954848A (en) *	1972-05-31	1976-05-04	Monsanto Company	Process for producing N-phosphonomethyl glycine
HU187347B (en) *	1981-07-31	1985-12-28	Mta Koezponti Kemiai Kutato In	Process for preparing n-phosphonomethyl-glycine by means of the catalytic oxidation of n-phosphonomethyl-imino-diacetic acid
US4853159A (en) *	1987-10-26	1989-08-01	Monsanto Company	Process for producing N-phosphonomethylglycine

1991
- 1991-01-24 AT AT91870015T patent/ATE126519T1/de not_active IP Right Cessation
- 1991-01-24 JP JP3006990A patent/JPH0692425B2/ja not_active Expired - Lifetime
- 1991-01-24 DE DE69112088T patent/DE69112088T2/de not_active Expired - Lifetime
- 1991-01-24 CA CA002034901A patent/CA2034901C/en not_active Expired - Lifetime
- 1991-01-24 NZ NZ236894A patent/NZ236894A/en unknown
- 1991-01-24 MY MYPI91000119A patent/MY104616A/en unknown
- 1991-01-24 IE IE24791A patent/IE74198B1/en not_active IP Right Cessation
- 1991-01-24 EP EP91870015A patent/EP0439445B1/de not_active Expired - Lifetime
- 1991-01-24 DK DK91870015.4T patent/DK0439445T3/da active
- 1991-01-24 ES ES91870015T patent/ES2027199T3/es not_active Expired - Lifetime
- 1991-01-24 HU HU91261A patent/HU208700B/hu not_active IP Right Cessation
- 1991-01-25 IL IL9704691A patent/IL97046A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE69112088D1 (de)	1995-09-21
HU208700B (en)	1993-12-28
ES2027199T1 (es)	1992-06-01
HU910261D0 (en)	1991-08-28
CA2034901C (en)	1996-07-02
HK1007147A1 (en)	1999-04-01
DE69112088T2 (de)	1996-02-29
EP0439445A1 (de)	1991-07-31
IE74198B1 (en)	1997-07-16
NZ236894A (en)	1992-12-23
ATE126519T1 (de)	1995-09-15
IE910247A1 (en)	1991-07-31
ES2027199T3 (es)	1995-12-01
MY104616A (en)	1994-04-30
EP0439445B1 (de)	1995-08-16
JPH04210992A (ja)	1992-08-03
CA2034901A1 (en)	1991-07-27
JPH0692425B2 (ja)	1994-11-16
DK0439445T3 (da)	1995-12-27

Legal Events

Date	Code	Title
1996-03-31	FF	Patent granted
1997-04-15	KB	Patent renewed
2001-06-14	KB	Patent renewed
2005-11-20	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
EP0464018B1 (de)	1995-10-04	Verfahren zur Herstellung von N-Phosphonmethylglyzin
EP0464017B1 (de)	1995-10-04	Verfahren zur Herstellung von N-Phosphonmethylglyzin
HK1007146B (en)	1999-04-01	Process for producing n-phosphonomethylglycine
US5095140A (en)	1992-03-10	Peroxide process for producing N-phosphonomethylglycine
US5077431A (en)	1991-12-31	Peroxide process for producing n-phosphonomethylglycine
EP0439445B1 (de)	1995-08-16	Verfahren zur Herstellung von N-Phosphonmethylglyzin
US5047579A (en)	1991-09-10	Process for producing n-phosphonomethylglycine
US5077430A (en)	1991-12-31	Peroxide process for producing N-phosphonomethylglycine
HK1007147B (en)	1999-04-01	Process for producing n-phosphonomethylglycine
HK1007145B (en)	1999-04-01	Peroxide process for producing n-phosphonomethylglycine
EP0490862B1 (de)	1996-01-24	Verfahren zur Herstellung von N-Phosphonomethylglyzin
EP0483098B1 (de)	1996-01-31	Verfahren zur Herstellung von N-Phosphonomethylglycin