IL103646A - Hydrogenation of enzymatically produced mixtures of glyoxylic / aminomethylphosphonic acids - Google Patents

Hydrogenation of enzymatically produced mixtures of glyoxylic / aminomethylphosphonic acids

Info

Publication number: IL103646A
Authority: IL; Israel
Prior art keywords: acid; reaction; catalyst; hydrogenation; glyoxylic
Prior art date: 1991-11-06

Application number

IL10364692A

Other languages

English (en)

Hebrew (he)

Other versions

IL103646A0 (en

Original Assignee

Du Pont

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.)

1991-11-06

Filing date

1992-11-05

Publication date

1996-10-16

1991-11-06 Priority claimed from US07/788,683 external-priority patent/US5135860A/en

1991-11-06 Priority claimed from US07/788,648 external-priority patent/US5180846A/en

1992-11-05 Application filed by Du Pont filed Critical Du Pont

1993-04-04 Publication of IL103646A0 publication Critical patent/IL103646A0/xx

1996-10-16 Publication of IL103646A publication Critical patent/IL103646A/en

Links

HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 title claims description 157
MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 title claims description 63
239000000203 mixture Substances 0.000 title claims description 33
238000005984 hydrogenation reaction Methods 0.000 title claims description 17
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 110
108010062584 glycollate oxidase Proteins 0.000 claims description 49
102000016938 Catalase Human genes 0.000 claims description 43
108010053835 Catalase Proteins 0.000 claims description 43
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 38
238000000034 method Methods 0.000 claims description 36
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
230000003647 oxidation Effects 0.000 claims description 30
238000007254 oxidation reaction Methods 0.000 claims description 30
239000001301 oxygen Substances 0.000 claims description 30
229910052760 oxygen Inorganic materials 0.000 claims description 30
239000003054 catalyst Substances 0.000 claims description 29
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 20
239000007864 aqueous solution Substances 0.000 claims description 18
230000008569 process Effects 0.000 claims description 18
239000000243 solution Substances 0.000 claims description 17
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 13
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
238000000354 decomposition reaction Methods 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 4
229910052759 nickel Inorganic materials 0.000 claims description 4
239000007868 Raney catalyst Substances 0.000 claims description 3
229910000564 Raney nickel Inorganic materials 0.000 claims description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
238000011065 in-situ storage Methods 0.000 claims description 3
102100038837 2-Hydroxyacid oxidase 1 Human genes 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 66
229960004275 glycolic acid Drugs 0.000 description 52
102100038838 2-Hydroxyacid oxidase 2 Human genes 0.000 description 43
238000004128 high performance liquid chromatography Methods 0.000 description 41
102000004190 Enzymes Human genes 0.000 description 38
108090000790 Enzymes Proteins 0.000 description 38
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 32
FVTCRASFADXXNN-SCRDCRAPSA-N flavin mononucleotide Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-SCRDCRAPSA-N 0.000 description 29
229940013640 flavin mononucleotide Drugs 0.000 description 29
FVTCRASFADXXNN-UHFFFAOYSA-N flavin mononucleotide Natural products OP(=O)(O)OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-UHFFFAOYSA-N 0.000 description 29
239000011768 flavin mononucleotide Substances 0.000 description 29
235000019231 riboflavin-5'-phosphate Nutrition 0.000 description 29
AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 26
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 20
230000000694 effects Effects 0.000 description 19
150000001412 amines Chemical class 0.000 description 14
239000000872 buffer Substances 0.000 description 14
230000002255 enzymatic effect Effects 0.000 description 14
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 12
241000228245 Aspergillus niger Species 0.000 description 11
241000219315 Spinacia Species 0.000 description 11
235000009337 Spinacia oleracea Nutrition 0.000 description 11
-1 ethylenediamine Chemical class 0.000 description 11
150000003839 salts Chemical class 0.000 description 9
238000004458 analytical method Methods 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
108030001056 (S)-2-hydroxy-acid oxidases Proteins 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
238000013019 agitation Methods 0.000 description 5
229910001873 dinitrogen Inorganic materials 0.000 description 5
239000011521 glass Substances 0.000 description 5
238000011084 recovery Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
229910019142 PO4 Inorganic materials 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
239000012736 aqueous medium Substances 0.000 description 4
239000002585 base Substances 0.000 description 4
238000003760 magnetic stirring Methods 0.000 description 4
230000001590 oxidative effect Effects 0.000 description 4
235000021317 phosphate Nutrition 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
238000005070 sampling Methods 0.000 description 4
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
238000013022 venting Methods 0.000 description 4
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 3
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
FSVCELGFZIQNCK-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)glycine Chemical compound OCCN(CCO)CC(O)=O FSVCELGFZIQNCK-UHFFFAOYSA-N 0.000 description 3
238000003556 assay Methods 0.000 description 3
239000007998 bicine buffer Substances 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
150000002466 imines Chemical class 0.000 description 3
230000002452 interceptive effect Effects 0.000 description 3
238000002955 isolation Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
230000009467 reduction Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
244000061176 Nicotiana tabacum Species 0.000 description 2
235000002637 Nicotiana tabacum Nutrition 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
OZZZWMYVGXXIMQ-UHFFFAOYSA-N aminomethylphosphonic acid;oxaldehydic acid Chemical compound OC(=O)C=O.NCP(O)(O)=O OZZZWMYVGXXIMQ-UHFFFAOYSA-N 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
230000007423 decrease Effects 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
229910001882 dioxygen Inorganic materials 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000002374 hemiaminals Chemical class 0.000 description 2
230000002363 herbicidal effect Effects 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
230000006872 improvement Effects 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
PKAUICCNAWQPAU-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetic acid;n-methylmethanamine Chemical compound CNC.CC1=CC(Cl)=CC=C1OCC(O)=O PKAUICCNAWQPAU-UHFFFAOYSA-N 0.000 description 1
OORRCVPWRPVJEK-UHFFFAOYSA-N 2-oxidanylethanoic acid Chemical compound OCC(O)=O.OCC(O)=O OORRCVPWRPVJEK-UHFFFAOYSA-N 0.000 description 1
235000000832 Ayote Nutrition 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
240000004244 Cucurbita moschata Species 0.000 description 1
235000009854 Cucurbita moschata Nutrition 0.000 description 1
235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
239000005562 Glyphosate Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
241001464837 Viridiplantae Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
150000004705 aldimines Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
238000012742 biochemical analysis Methods 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000000539 dimer Substances 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
235000019797 dipotassium phosphate Nutrition 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
239000006260 foam Substances 0.000 description 1
LXFSGRVKYHMMDN-UHFFFAOYSA-N formic acid 2-hydroxyacetic acid oxaldehydic acid oxalic acid Chemical compound C(CO)(=O)O.C(CO)(=O)O.C(C(=O)O)(=O)O.C(=O)O.C(C=O)(=O)O LXFSGRVKYHMMDN-UHFFFAOYSA-N 0.000 description 1
229940015043 glyoxal Drugs 0.000 description 1
229940097068 glyphosate Drugs 0.000 description 1
235000021384 green leafy vegetables Nutrition 0.000 description 1
150000002373 hemiacetals Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
229940102253 isopropanolamine Drugs 0.000 description 1
239000012035 limiting reagent Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
210000004962 mammalian cell Anatomy 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
239000000178 monomer Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
229910052762 osmium Inorganic materials 0.000 description 1
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
238000005949 ozonolysis reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical class [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
235000015136 pumpkin Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 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
229910052707 ruthenium Inorganic materials 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
239000002699 waste material Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/373—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in doubly bound form
- 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
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/42—Hydroxy-carboxylic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Biochemistry (AREA)
General Chemical & Material Sciences (AREA)
Microbiology (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Oil, Petroleum & Natural Gas (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL10364692A 1991-11-06 1992-11-05 Hydrogenation of enzymatically produced mixtures of glyoxylic / aminomethylphosphonic acids IL103646A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US78864091A	1991-11-06	1991-11-06
US07/788,683 US5135860A (en)	1991-11-06	1991-11-06	Process for preparing glyoxylic acid/aminomethylphosphonic acid mixtures
US07/788,648 US5180846A (en)	1991-11-06	1991-11-06	Hydrogenation of enzymatically-produced glycolic acid/aminomethylphosphonic acid mixtures

Publications (2)

Publication Number	Publication Date
IL103646A0 IL103646A0 (en)	1993-04-04
IL103646A true IL103646A (en)	1996-10-16

Family

ID=27419857

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
IL10364692A IL103646A (en)	1991-11-06	1992-11-05	Hydrogenation of enzymatically produced mixtures of glyoxylic / aminomethylphosphonic acids
IL10364592A IL103645A (en)	1991-11-06	1992-11-05	Enzymatic preparation of N-) phosphonomethyl (glycine

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
IL10364592A IL103645A (en)	1991-11-06	1992-11-05	Enzymatic preparation of N-) phosphonomethyl (glycine

Country Status (16)

Country	Link
EP (4)	EP0541333A1 (fr)
JP (2)	JPH07501940A (fr)
CN (2)	CN1073481A (fr)
AU (2)	AU673146B2 (fr)
BR (2)	BR9206884A (fr)
CA (2)	CA2123079C (fr)
CZ (2)	CZ111394A3 (fr)
DE (1)	DE69210771T2 (fr)
ES (1)	ES2087460T3 (fr)
HU (2)	HUT71955A (fr)
ID (1)	ID1002B (fr)
IL (2)	IL103646A (fr)
MX (2)	MX9206363A (fr)
MY (1)	MY130099A (fr)
NZ (2)	NZ245012A (fr)
WO (2)	WO1993009243A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0541333A1 (fr) *	1991-11-06	1993-05-12	E.I. Du Pont De Nemours And Company	Hydrogénation de mélanges de l'acide glyoxylique/aminométhylphosphonique obtenues par voie enzymatique
BR9408601A (pt) *	1993-03-03	1997-11-25	Du Pont	Processo para preparação de uma mistura de ácido glioxilico e ácido aminometilfosfónico
CA2163515A1 (fr) *	1993-05-28	1994-12-08	David Leroy Anton	Methode pour preparer des melanges acide glyoxylique/aminomethylphosphonate dialkylique
AU7211994A (en) *	1993-07-01	1995-01-24	E.I. Du Pont De Nemours And Company	Glycolate oxidase production
AU7316294A (en) *	1993-07-01	1995-01-24	E.I. Du Pont De Nemours And Company	Microbial transformants of (hansenula) that express glycolate oxidase and catalase
AU674619B2 (en) *	1994-12-15	1997-01-02	Jack Newman	Stereoscopic micromirror display
WO2022133719A1 (fr) *	2020-12-22	2022-06-30	Rhodia Operations	Procédé de production d'acide glycolique

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL48619A (en) *	1974-12-11	1978-04-30	Monsanto Co	Process for the production of n-(phosphonomethyl)-glycine compounds
IL48639A (en) *	1974-12-11	1978-06-15	Monsanto Co	Process for the production of carbonylaldiminomethanephosphosphonates
HUT41415A (en) *	1984-12-28	1987-04-28	Monsanto Co	Process for preparing n-phosphono-methyl-glycine derivatives
EP0496799B1 (fr) *	1989-10-16	1993-09-08	E.I. Du Pont De Nemours And Company	Production d'acide glyoxylique par oxydation enzymatique d'acide glycolique
EP0541333A1 (fr) *	1991-11-06	1993-05-12	E.I. Du Pont De Nemours And Company	Hydrogénation de mélanges de l'acide glyoxylique/aminométhylphosphonique obtenues par voie enzymatique

1992
- 1992-11-03 EP EP92310064A patent/EP0541333A1/fr not_active Withdrawn
- 1992-11-03 WO PCT/US1992/009420 patent/WO1993009243A1/fr not_active Ceased
- 1992-11-03 DE DE69210771T patent/DE69210771T2/de not_active Expired - Fee Related
- 1992-11-03 CZ CZ941113A patent/CZ111394A3/cs unknown
- 1992-11-03 HU HU9401416A patent/HUT71955A/hu unknown
- 1992-11-03 AU AU30616/92A patent/AU673146B2/en not_active Expired - Fee Related
- 1992-11-03 JP JP5508669A patent/JPH07501940A/ja active Pending
- 1992-11-03 BR BR9206884A patent/BR9206884A/pt not_active Application Discontinuation
- 1992-11-03 CA CA002123079A patent/CA2123079C/fr not_active Expired - Fee Related
- 1992-11-03 EP EP92310063A patent/EP0545553B1/fr not_active Expired - Lifetime
- 1992-11-03 HU HU9401419A patent/HUT71271A/hu unknown
- 1992-11-03 CA CA002123081A patent/CA2123081C/fr not_active Expired - Fee Related
- 1992-11-03 JP JP50866893A patent/JP3315119B2/ja not_active Expired - Fee Related
- 1992-11-03 ES ES92310063T patent/ES2087460T3/es not_active Expired - Lifetime
- 1992-11-03 EP EP92924227A patent/EP0611398A1/fr active Pending
- 1992-11-03 EP EP92924228A patent/EP0611399A1/fr active Pending
- 1992-11-03 WO PCT/US1992/009419 patent/WO1993009242A1/fr not_active Ceased
- 1992-11-03 AU AU30617/92A patent/AU658956B2/en not_active Ceased
- 1992-11-03 BR BR9206882A patent/BR9206882A/pt not_active Application Discontinuation
- 1992-11-03 CZ CZ941114A patent/CZ111494A3/cs unknown
- 1992-11-04 MY MYPI92002001A patent/MY130099A/en unknown
- 1992-11-04 NZ NZ245012A patent/NZ245012A/en not_active IP Right Cessation
- 1992-11-04 NZ NZ245011A patent/NZ245011A/en not_active IP Right Cessation
- 1992-11-05 IL IL10364692A patent/IL103646A/en not_active IP Right Cessation
- 1992-11-05 MX MX9206363A patent/MX9206363A/es not_active Application Discontinuation
- 1992-11-05 IL IL10364592A patent/IL103645A/en not_active IP Right Cessation
- 1992-11-05 MX MX9206362A patent/MX9206362A/es unknown
- 1992-11-06 CN CN92114382A patent/CN1073481A/zh active Pending
- 1992-11-06 ID IDP497492A patent/ID1002B/id unknown
- 1992-11-06 CN CN92114383A patent/CN1073482A/zh active Pending

Also Published As

Publication number	Publication date
CA2123079C (fr)	2005-01-25
BR9206882A (pt)	1995-06-13
CN1073482A (zh)	1993-06-23
HU9401416D0 (en)	1994-08-29
EP0541333A1 (fr)	1993-05-12
JPH07504084A (ja)	1995-05-11
EP0611398A1 (fr)	1994-08-24
IL103645A (en)	1996-10-31
CA2123081C (fr)	2003-02-25
HUT71955A (en)	1996-02-28
CZ111394A3 (en)	1994-12-15
NZ245012A (en)	1995-05-26
AU3061692A (en)	1993-06-07
DE69210771T2 (de)	1996-12-12
CA2123081A1 (fr)	1993-05-13
WO1993009242A1 (fr)	1993-05-13
AU658956B2 (en)	1995-05-04
CZ111494A3 (en)	1994-12-15
BR9206884A (pt)	1995-07-11
CN1073481A (zh)	1993-06-23
IL103646A0 (en)	1993-04-04
JPH07501940A (ja)	1995-03-02
EP0545553B1 (fr)	1996-05-15
ID1002B (id)	1996-10-10
AU673146B2 (en)	1996-10-31
JP3315119B2 (ja)	2002-08-19
EP0545553A1 (fr)	1993-06-09
WO1993009243A1 (fr)	1993-05-13
HU9401419D0 (en)	1994-08-29
ES2087460T3 (es)	1996-07-16
HUT71271A (en)	1995-11-28
MY130099A (en)	2007-06-29
CA2123079A1 (fr)	1993-05-13
EP0611399A1 (fr)	1994-08-24
NZ245011A (en)	1995-05-26
AU3061792A (en)	1993-06-07
DE69210771D1 (de)	1996-06-20
MX9206362A (es)	1993-06-01
MX9206363A (es)	1994-02-28
IL103645A0 (en)	1993-04-04

Legal Events

Date	Code	Title	Description
1997-03-18	FF	Patent granted
1999-11-30	RH	Patent void

Publication	Publication Date	Title
CA2165940C (fr)	2005-09-13	Methode de preparation d'acide pyruvique
CZ11194A3 (en)	1995-02-15	Module differential switch
EP0545553B1 (fr)	1996-05-15	Préparation enzymatique de N-(phosphonométhyl)-glycine
US5135860A (en)	1992-08-04	Process for preparing glyoxylic acid/aminomethylphosphonic acid mixtures
US5180846A (en)	1993-01-19	Hydrogenation of enzymatically-produced glycolic acid/aminomethylphosphonic acid mixtures
CA2067382C (fr)	2002-05-14	Production d'acide glyoxylique a partir d'acide glycolique
US5559020A (en)	1996-09-24	Process for preparing glyoxylic acid/dialkyl aminomethylphosphonate mixtures
US5262314A (en)	1993-11-16	Enzymatic oxidation of glycolic acid in the presence of non-enzymatic catalyst for decomposing hydrogen peroxide
US5221621A (en)	1993-06-22	Production of glyoxylic acid from glycolic acid
EP0706577B1 (fr)	1997-08-27	Procede de preparation ameliore de melanges d'acides glyoxylique/aminomethylphosphonique au moyen d'un double transformant microbien
WO1996000793A1 (fr)	1996-01-11	Melanges d'acide glycolique et d'acide aminomethylphosphonique prepares a l'aide d'un transformant microbien