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    Recovery Noble Metais

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    pedro

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    United States Patent 168766332 0 10 Patent No: US 7,687,663 B2 Scaia et al. (45) Date of Patent: Mar. 30, 2010 (5!) RECOVERY OF NoBL From 3078489 A 81976 Hagen AQUEOUS PROCESS STREAMS torean A Rive Siner (75) inventors: Mark D. Sea, St Louis, MO (US) A 191876 Bed eta David R. Eaton, Kikwood, MO ( A 121876 Grates etal Roger Jc Hockstra, St Lots, MO (US) ete En A. Haupfear,St-Chales MO (US) Aen a (73) Assianeo: Monsanto Technology LLC, St.Louis, (Continved) MO FORFIGN PATENT DOCUMENTS (4). Notice: Sobjoct i any disclaimer, the term ofthis yp caer patents extended or adjusted under 35 : TIS. 154 by 720 days (Continsed) ae oritpR PUBLICATIONS Seas: Gans, M: is, S: Pasa, P "Cononton of (22) Filed: Now. 14,2008 Cu) and Gpptou athe Wate-Goaht er Fc00TD Irie Molar Sete om ant TXATS Senta our « Prior Publication Data ‘tot oto ant sre Sec. 200% pp 389 a 302 US 20060105248 AI May 18,2006 (Continsed) ated US. Application Date Primary Examiner Sika A Witherspoon Related U.S. Application Ds Assistant Examiner—Chukwuma O Nwaonichs (60) Provisional aplication No, 60627.668, ed on Now. (P4)dtorny Agent. or Firm Seige Powers PJosph 12,2008 A Shaper s) mer 6 asTract Ci 522 00601) feo juster 56217, 502/10 This invention senealy relates to process fr recovering Oe reesei aed ‘Maxi, sltbilzcd noble met om ajusus proces seams in Said re at ci ee eth ps Soames atl example, by noble metal-catalyzed oxidation of an (66) References Cited ¥(poophonmstyiminoiacte aid substrate. The po USS. PATENT DOCUMENTS, amos A 301974 rane s9q@a98 A 711976 Hershman ess includes contacting the aqueous process stream with ‘be metal adsorption media such as an ionexcha remove solubilized noble metal from the process stream, 29 Claims, 2 Drawing Sheets ppm Pt Ptin column effluent ‘500 1000 mloluted 1500 2000 US 7,687,663 B2 Page 2 US. PATENT DOCUMENTS, 5902185 A 4199 De Boer S3n8253 A 41994 Awaalla ta 44060,040 4/1978 “Thomas ea S209 A 71994 Hanet al 077800 A W197S Pekaet al SBIR A 1904 Kohe 4001586 A 41978 Walle S3s8300 A 101904 Want omit A S978 Diet ea S3S4458 A 101004 Wang eal A GII97S Swinkels ea. Shotaag A T1904 McDowlett eta A S197 wands ta S$ 11/1998 Kobr A 81978 Lakeetal A 41995. Groves ta A UNOS MacGregor A $1995 Kanget al i2se2 A 121978 Ghisinghell et Saigo A 81908 ure 4162950 A 71979 MacGregor Sqaseat A 81995 Kohe 4216012 A 81980 Kroeiak S440307 A 910995 Hunter eta 4239853 A 121980. Retmaniak et al S(608863 A 21007 Kuby etal 4257807 A “3981. Drobot Sieur A 21997 Smith 4261736 A 41981 Valentin ta Sii2431 A V1997 Waddellet a 426531 A D981 Tochavelore a Si26.647 A $1997 Kohe 4300317 A L981 Mock 567219 A 91997 Hunterstal 4337225 A 6L1982 Poly ta 5490806 A 11/1997 Suneriand et ASH) AS11983 Wenn S788936 ‘71998 Thon ta A827 A 6:1983 Quick Som23s A 1098 Kohe Sso768s A 81983 Winkler sta Sso73a4e A 101998 Wall eta 4400250 881983 Faitunt Spwox A ‘81999 Vimig etal, 4412.89 A 11/1983 Hateld etal Spa2008 A $1999 Sehisuo etal 4426251 A “1198S duet 008,140 A * 121999 Morgenstem etal oon 86217 S4s0I88 A $988 Kawau 2001. Vimg oa Saoves7 A 201085 Hated eta {6252498 BL $2001 Morgensem aa 44510027 A 411985 Waewonowski ea 274s BL $2001. Kiesler 451159 A 41985. Stephenson OBISSL2 BL 12001 Fleming eal 4526618 A TH985. Bethe a 6364931 BL “42002 Robinson eal S'SHR7O1 A 101985 Fletcher et GAL BL 72002 ‘hiker 457128 A 21986. Keroot eta 6417138 BL 72002 Boner 45e1650 A 41986 Felthouwe 6440198 BL $2002 Krofhak eta 45027 A G.1086 Russa 6444010 BL 92002 Watanabe 412388 A 911086 Mitac a 458018 BL 92002 Cuit 4624087 A L1086 Chow 6300231 BL 122002 Wan 4.662513 A SI1987 Woog 658137 B2 42003 Faone otal 41566212 A 51987 Lowa a 60008 BL 62003 Lidell 4470052 A GI19K7 Staley Gseee2 B2 72003 Leiber eal 469672 A 911087 Chow {6603039 BL 82003 Foner ta 4728313 A 21088 “Adamson G500818 BE $2008 Hite ea sos Ar6si A 21088 Grate 027308 B2 82008 Leiber 1726939 A 2/1988, Touro {5986005 2 102005 ether ArI8s19 A 101088 Posie 7.179936 B2* 22007 Hayprear etal sou17 SSLM007 A989 Line a 20020068886 AL 62002 tlapfen etal. S119 Sop doovon26329 Al 22004 Ekman tal S990 White doowo1o26ss Al* S2008 Brown etal 504913 A W199 Linetat A 21990 Behnam eta FOREIGN PATENT DOCUMENTS, X— H1900 Dickson X1990 Conegy eal P 2001243 102001 A 21991 Lineal P ao2o7i9s A 4/2002 ‘4992207 A 2901 Dsmall eta ® aovsoorsia A 1/2008 048290 A 911991 Harve al Wo wooo AL 22000 soso A 1/1902 Gallup etal 5087740 A 2/1992 Smith (OTHER PUBLICATIONS Suonss2 A 411992 Alen etal Silesis A $1992 Rina Appleton, ot a, “Amino Acid Complexes of Pltinun(1V) 1 SUIS A 611002 Hochela ta Trimethypatinan TV) Complexes with Clyeinate, minodaceat, SUATRAL A 91992. Wileoxom N-Mathyliminodacete, Nislicette, and ikyleniine: Susi2a4 A 911992 Malou eat Tetsacett,” Inorganica Chimica Aca, 1978, pp. 8959, so. 9, SUGO7IL A 11/1992. Afkinon Switzer 5179228 “11995. Marin Ramon ‘Appleton, "Donor Atom Preferences in Compleses of Platinum snd S201942 A 4/1993 Demopoutos eta Palladiam with Amino Acids and Related Molecles” Coordination A 51993 Pacha ta (Chemistry Reviews 165, 1997. pp 313-359. SX 5i1993 Hyde a Appicion, ct al, "Multinciear NMR. Study of Reactions of A @1008 er “Mathyiphosphonic Aci CHPO;H and (Amina) Phosponic A 91003 Breley etal, Acids, NICH.) POsH, (@-13). With the c-Diam A 101993. Motjima etl ‘minediaquapainuiatt) "Caton and cis-Diane ‘A 101093 awa etal ‘minh lroxoplatiaund)" Inorganic Chemisty, 1985, pp. 720 A * 101999 Gefen TSI 728-vol 28.No. 6, Brisbane, Ausealis ‘A 21908 Gefvet Appleton, tal. “NMI Specta of Ininabis (meslenephosphonic A 1004 Duyresteya etal ‘cd, HN(CH,PO,H), and Related Ligamde and of Theis Con US 7,687,663 B2 Page 3 exes with Patinn()” Inoganie Chemisty 1986, pp 720-734 tol 25.No. 6, Brisbane, Avs ‘Appleton, al, “Platinum Compleses with Iminoiceate ant (ediyfimino) Diacease, studing” Genuine Merion Com exer” Inorganic Chenin, 1985, pp 04672, vo 24, No. 5, Diistane, Ansan Appleton al, “Pstiaus (1) Complexes wih Glycine as n Oxy fen-Bound Unidenate Ligand” 1 Chem. Soe, Chem Come 1983, pp 911913, Bosbane, Avaralin, Crystal Strates of hice Dimtypatinam{1V) Complexes with 24Phosphonamayl) Gysine Coowlinsted Facial. Inorganic ‘Chemisty, 1994, pp 444-455, vo. 33, No.3, Brisbane, Avalia Appleton, otal, "Reactions of Pinuncl}) Aqua Compleses. 3. Malinuicar (8, 9, "C, and "H) NM Stuy of Reactions of Aqua and Hydoxo Completes wih Glyeine and (Mtstinino) Diaceti Acid Inorganie Chemistry, 1988, pp. 673.677, vol. 24, Nos, Brisbane, Asli Bate & al. "Synthesis, Spectroscopy. and Theoretical Stes of Platina) Phosphate Complexes” Chem Soe Dalton, 2002, 1998-1902, vol. 9. Baha, tal. "Compleces of Platinum) and Palladium with Ainomethyiphosphonie Acid and Glyyaminomthyipaosphonk. Aci" Chem Soe Dalton, 1997 pp. 2621-2625, vo. Dow Chemical Corsaay, "Cokin Separations Using Rens and Adsobents Tech Fact Lab Gade Fe. 2001 pp 13 Dow Chemical Company, “Dowex fon Exchange Resins Equitsam Tnatherm Testing for Lied Phase Application” Aplicaion Infor. ‘ation Leaflet May 197, Dow Chemical Company “Dowex M43 fon Exchange Resin Cor ‘oso Control wth Dowee Mel3 lon Exchange Reta” Application Information Leaflet, Fb, 1098 rickson, etal, “Eqiltrium and Kinetic Studies of Monoaquo Complexes of Plaimura) I. Formation from Comesponding Coro Species by Hyatt Inorganic Chery, 1987, pp. 92 997, vo 26, No.7 Franz, et al. “Gyphosse: A Unique Global aici” Ameican Chemie Society Monograph 189, 1997, pp. 233-202. Gru, "Precious Metal Recovery rom Spent Catalysts" Pinu Metals Kev. 2003, pp 163-165, vl 47, No.4 Hou, eal. “mpaoved Profiabity Tough ReSource Recovery” yoarton Enginerng, Dee 203 MeGarvey, & al, "Removal and Recovery of Metals by on Exchange” Catalog, 1988, pp. 10. Nagao ct al. "Platinum Complexes with Diglycie:X-ay Cys tal Stoctre, ON NMR Specta, and Growtinibory Activ ‘Aginat Mouse Math A Sol Tumor in Vivo Inorg Chem 36,1997, pp 4195-4201, vo. 19, Purlite “ASO? Macroporous Strong Base Anion Exchange Resin (Wor the removal of cellidal sila)” Techneal Daa Product Deserqtion. pr. 198 Sopays al, “Metal Complexes wih N-(Phosphonomets) Giyeine(Glphosatey The Preparation and Characezaton of tbe (Group 2 Metal Comploces with Glyphosate and theCrystal Stlcture of Barium Glyphosate Diyite,”AusualianJoumal of Chemisty, 2000, pp. 7-51 vol 83.No.2 ‘Schule al, “Sythe and Characterization of Palladi)aad Platina)” Complexes Containing Water Solble Hybrid Phosphine-Phosphonte Ligand” Inorganic Chama, 196, pp 67176723, vo. 38, No.2 * cited by examiner US 7,687,663 B2 Sheet 1 of 2 Mar. 30, 2010 US. Patent =) 6 otas 5 seag [a] Savor | = (erew sopea1 uonepxo sojetodeng ae; t e T OIA US. Patent Mar. 30,2010 Sheet 2 of 2 US 7,687,663 B2 FIG. 2 Ptin column effluent ppm Pt oO 500 1000 1500 2000 2500 ml eluted US 7,687,663 B2 1 RECOVERY OF NOBLE METALS FROM AQUEOUS PROCESS STREAMS REFERENCE TO RELATED APPLICATION ‘Tis application claims benefit of US, provisional appi- ‘ation Ser, No, 60/627,668 fled Nov. 12, 2004, the entire disclosure of which is incorporated herein by reference. PIELD OP THE INVENTION ‘The present invention relates generally to techniques for recovering solubilized noble metals from aqueous process streams, in parcular aqueous process streams generated in the preparation of an N-(phosphonomethyl)ayeine product, foe example, by the noble metal-catalyzed oxidation of an N-(phosphonomethyDjminodiacetie aed subsea BACKGROUND OF THE INVENTION N-(phosphonomethyalyeine (known in the ageicultaral ‘chemical industey as glyphosate) is deserbed in Franz, US. Pat. No. 3,799,758. N-(phosphonomethyljglycine and its salls are conveniently applies post-emergeat herbicide in ‘aqueous formulations. Iisa highly effective and commer- important broad-spectrum herbicide usefil in illingor ‘contolling the growth ofa wide varity of plants, inehuding germinating sed, emerging soodlings, maturing and estab- lished woody and herbaceoss vegetation, and aquatic plants Various methods for making N-(phosphonomethylly- «ine products are known in the art. One of the more widely ‘accepted methods of making N-(phosphonomethy?)glyeine ‘compounds includes the liquid phase oxidative cleavage of ‘carboxymethyl substitient from an N-{phosphonomethy!) iminodiacetie aed substrate using an oxyen-contaning gas inthe presenceofabeterogencons oxidation catalyst. As used herein, "Ne(phosphonomethyDiminodiacetic acid sub- strates” include N-(phosphonomethyDjminodiaoetic acid (sometimes referred io as PMIDA) and salts thereof, wherein ‘he saltfarming cation is for example, amamonivim, alkylam= ‘onium, aa alkali metal oe an alkaline earth metal, For ‘example, N-(phosphonomethylialyeine may be prepared by the guid phase oxidative cleavage of N-(phosphonomethy!) iminosiacetc acid with oxygen in accordance with the fol- lowing reaction: (HO,ROKHNC! = Other by-products also may form, such as formic acid ‘whichis formed by the oxidation of the formaldehyde product, and aminomethylphosphonie seid (AMPA), which 's formed by the oxidation of N-(phosphonomethy glycine The preference for heterogeneous catalysis stems, at Teast in par, from the ease With whieh particulate heterogenous ‘alalyt can normally be separated from the reaction product mixture for ruse following the oxidation. The literate is replete with examples of heterogeneous catalysis of Ne(phosphonomethy)jiminodiacetic acid substrates in the prxluction of N(phosphonometyjalycine compounds. See enerally, Franz, etal, Glyphosate:A Unigue Global Herbi- ‘ide (ACS Moneraph 189, 1997) at pp. 233-62 (and reker- ‘ences cited therein); Franz, US. Pat No, 3,950,402; Hersh man, US. Pat, No. 3969,398; Felthouse, U.S. Pat No. 4,582, 2 650; Chou, U.S, Pat. Nos. 4,624,937 and 4,696,772; Ramon etal, USS. Pat, No, 5,179,228; Ebner et al, U.S, Pat, No, 6,417,133 Leihor et al, US. Pat. No. 6,586,621 and Liber, US. Pat. Nos. 6,927,304 andl 6,956,005, The eniediselosure of the patents referred 10 in this paragraph and all other patents and publications refered t thoughout this appliea- ‘ion ae ineorported herein by reference, igh concentrations of formaldehyde in the reaction prod- vet solution resulting ffom oxidative clewage of an [N-{phosphonomethyjiminodiacetic acid substrate ae unde- sirable. The formaldehyde by-product is undesirable because it reacts with NephosphonomethyDglveine to produce unwanted by-products, mainly N-methy!-N-{phosphonom- ethyDglycine (NMG), which reduces the N-(phosphonom ‘ethyljlveine yield. I addition, the formaldehyde by-product itself is undesirable because of its potential toxiity. See Smith, US. Pat. No. 5,606,107. Franz, US. Pat. No. 3.950.402, discloses oxidizing the formialdchyde by-product to carbon dioxide and water simul rncously With the oxidative elewage ofthe (phosphono: tiyl)iminodiacetie acid substrate by using a heterogencous ‘oxidation catalyst comprising a nable metal deposited on @ ‘carbon support. The aable metal on carbon oxidation catalyst ‘nay be referred to as “bifintional” in tht the earhon eomn- nent provides the primary adsorption site forte oxidation bf the N-(phosphonomethy)jiminodiaeetic acid substrate to form the N-iphosphonomethyDglyeine product and form dehyde, while the noble metal component provides the ri ‘mary adsorption site for the oxidation of formaldehyde and formic acid o form earbon dioxide and water, thus giving the following overall reaction: HO POCHANHCH 2€0 + 120 ‘The noble metal component may also tend to reduce the rate of deactivation ofthe catalyst (ce. prolong the use life ‘of the catalyst). In aditon 1o the N-(phosphonomethyl ly. cine product, formaldehyde, formic ack and unreacted N-(phosphonomethy!jiminodiaceticaeid substrate, the Oxi- ation product solution may also contain other by-prodvets, such as Nemthy/-N-(phosphonomethyl glycine (NMG), [N-fonmyI-N-{phosphonomethyDglyeine (NF'G),aminometh ylpbosphonic acid (AMPA), methyl aminomethylphospho- hie aid (MAMPA) iminodiaeeie seid (IDA), glycine, ay oxylie acd, phosphoric acid, phosphorous acid and imino- bismethylene)-bisphosphonic acid (iminobis) and mixtures thereof. Even though the Franz method produces an acceptable yield and parity of N(phosphonometiy]jalycine, high losses ff the costly anble metal by dissoution into the reaction mixture (Le, leaching) typically result, Under the oxidation conditions ofthe reaction, some f the noblemetalisoxidized into @ more soluble form and organic components of the reaction solution, such asthe N-{phosphonamethy!iminod acetic acid substrate and the N-(phosphonomethy] glycine product, may aet as ligands that solubilize the noble metal ‘andr sequester the solubilized noble metal i organic che- fe complexes. ARer the N-{phosphonomethy_)glysine prod vet has been formed and the noble metal catalyst has boon separated rom the reaction mixture, the oxidation prod! solution may be concentrated (e,2, by evaporation) to pre cipitate N-(phosphonomethyligyeine prodvet erystals and then separate the solid product from the various by-products US 7,687,663 B2 3 ‘and impurities retained in the resulting depleted reaction Solution or mother liquor. Although a substantial quantity of the mother Higuor may be reeyclet within the progess, com mercial considerations typically dictate that at least a portion ‘of his residual reaction solution be purged from the system to void the build vp of undesirable impurities and by-peeducts that may compeomise product purity. This purging unavoid- ably resulis inthe los of at east some ofthe solubilized noble metal andthereby undermines the economic Feasibility ofthe process. Furthermore, the presence of solubilized noble metal inthe reaction mixture typically results in incorporation ‘of some noble meta into the N-(phosphonomethy?)alyeine product resulting in additional loss of the noble metal ike Franz, Ramon t al, US. Pat. No. §,179,228, teach using a noble metal deposited on the surface of a carbon supporto caalye the oxidative cleavage ofan N-(phospho- hamethy))iminodiacetie acid substrate, To reduce the prob- lem of noble metal leaching (reported to be as great as 30% noble metal loss per eyele) Ramon eta. teach flushing the reaction mixture With nitrogen under press dation reaction is complete to cause re-depositon of the noble metal onto the surface ofthe carbon support. According to Ramon etal nitrogen fushing reduces the noble metal loss to lesthan 1% ‘More recently atntion has focused on developing hifne- tional nable metal on carbon oxidation catalysts that resist noble metal leaching (i... exhibit improved compositional stability) and provide increased activity and/or selectivity, particularly with respect to oxidation of formaldehyde into ‘carbon dioxide and water (ce. increased formaldehyde activ ity) Bbner etal, US. Pat. No. 6,417,133, disclose so-called “deeply reduced” noble metal on carbon catalysts for use in the oxidative cleavage of an N-{phosphonomethyiminod- scetic acid substrate and oxidation of other oxidizable reagents and methods for their preparation. Such deeply reduced catalysts exhibit remarkable resistance 10 noble ‘metal leaching in aqueous, acidic oxidation reaetion media, ‘Asa resul the catalyst disclosed by Ebner tal. provides for substantially quantitative oxidation of N-(phosplhonomethy!) iminodiacetc acid substrates to N-iphosphonomethyl)aly= ‘ineproduets, while minimizing noble metal lossesand main- taining effective oxidation of the fomnaldehyde and formic ‘seid by-products ofthe reaction fora prolonged periodandor ‘over numerous oxidation cycles. ‘Although the techings of Ebner et al are signi make economically practical the otherwise unavailable ‘advantages provided by noblemetal on carbon catalysts inthe preparation of Nphosphonomethylglyeine products by ‘oxidative clewage of N-phosphonomethy Diminadiaestic, cid substrates, pble metal losses in aqueous wast streams purged from the process and noble metal losses. in N«phosphonomethyDalyeine product streams cannot be ‘completely avoided and represent a significant operational ‘ost. Thats despite the improvement in catalyst stability nd tzenerl resistance to noble metal leaching provided by the ‘deeply’ reduced eatalyst of Ebner ta, overall process coo nomics ae stl diminished to some extent by the leaching of noble metal under the sever acidic oxidation reaction con- ditions which include the presence of the N-(phosphonom= ‘ethy)elycine produet and other onnie components that may ‘cla ligand andl exacerbate noble metal leaching even from, stabilized bifunctional catalyst systems. Accontingly, need ‘exists for effective tectnigues for reeovering the solubilized robe mictal from aqueous process steams prochiced in the preparation of N-(phiosphonomethyDelyeine products by the noble metal-catalyzed oxidation of N-(phosphonomethyl) iminodiacetc acid substrates. The recovered noble metal after the oxi- 2 4 could be reclaimed andl advantageously used in the prepars+ ‘ion of fresh catalyst to significantly improve overall eonom- ies ofthe process, SUMMARY OF THE INVENTION Among the objects ofthe present invention, therfore are the provision of techniques efetve for recovering soubi- liad noble metas rom process sean in particular agus ous process steams generated in the” peeparaion of an NphosphonometyPayeine pct, for example, by the soble mal caaly2ed oxidation of an N-(phosphonomets}) ininodisceic aid substrate; the provision oF improved pr cones fr the preparation of N-(phosphonomethl}ayeine products by the noble itacatalyzed oxidation of an osphonomethy)iminodiacetc aid substrate in which operational costs are reed by effective recovery of noble metal solubilized in the reaction prodet mixtures andthe Provision of such procescs whercin the recovered noble metal may be lized inthe preparation of fresh etal Brill, therefore the present invention is drwctad 0 a proces or recovering noble meal from an agueods press Strom, cling solubilized noble etal, the au ro covssfcam having been generated ina proces for making an N-phosphonomethy!lyeine product by the noble metal catalyze oxidation of an N-(phosphionomet iminodace- tie aid substrate, The rovery process inludes contacting the aqueous process steam with noble ctl adsorption ‘media to remove at lest portion othe slubiliagd noble metal therefom and peodice a treated aqueous process Sram ving & edict concentration of noble met ad a able metal adsorption media comprising a noble met The present invention is further directed to a process for making an N-phosphonomethyDalyeine rode. The peo- Cessincdes exidizang an N-(phosphonometiimindiace- ti aid substrate nan enidaton eator sytem inthe pres ence of a oxidation catalyst including & aoble met to Produce a reaction prodet mixtre comprising the noble Inetal eatalyst and a reaction prduet solution comprising ‘N-iphosphonomethy)alyeine product and solbilized noble inet The N(phosphonomethyDgyeine product is then pre Ciptatodin esta orm rom the reaction product sootion to produce a product slury comprising precipitated N-iphosphonomcty! lysine product ental anda mother Tiqlor containing the soldbiized ble meta The N-ihosphonomethy!elyeine product crystal are separated ftom the prodet slurry to produce an N-phosphooomets?) aleine product wet-cake and an aqueos slis-depleted Sucam coining mothe liguorand the noble metal Pll, ft last a portion ofthe aquooos slds-deplated steam is onacied With a noble metal adsorption media to remove at Icastaporionof the solubilized anble metal fom the giants sofidsdepleted seam and pce a tate aqueous solids depleted steam having a reduced concentration of noble ‘net ands noble metal adsorption een comprising a aoble meta “The present invention is further directed toa process for snaking an N-(phosphonometiyl glycine product. The pro cessinchudes oxidizing an N-(phosphonometyhiminodace- tie aid substrate ina oxidation reactor system inthe pres face of an oxidation catalyst inchading ® noble metal to produce @reacton product mixture comprising the noble fetal catalyst and a reaetion product solution including [N-iphosphonomethylyeine product and solbilizd noble US 7,687,663 B2 5 ‘metal, The reaction proviet solution is concentrated to pre=

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