AU2005292337A1 - Chelating agents for heavy metal removal - Google Patents
Chelating agents for heavy metal removal Download PDFInfo
- Publication number
- AU2005292337A1 AU2005292337A1 AU2005292337A AU2005292337A AU2005292337A1 AU 2005292337 A1 AU2005292337 A1 AU 2005292337A1 AU 2005292337 A AU2005292337 A AU 2005292337A AU 2005292337 A AU2005292337 A AU 2005292337A AU 2005292337 A1 AU2005292337 A1 AU 2005292337A1
- Authority
- AU
- Australia
- Prior art keywords
- resin
- group
- substituted
- alkylene
- hydrogen
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 229910001385 heavy metal Inorganic materials 0.000 title description 49
- 239000002738 chelating agent Substances 0.000 title description 13
- 229920005989 resin Polymers 0.000 claims description 250
- 239000011347 resin Substances 0.000 claims description 250
- 239000003446 ligand Substances 0.000 claims description 85
- 229910052751 metal Inorganic materials 0.000 claims description 73
- 239000002184 metal Substances 0.000 claims description 73
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- 239000001257 hydrogen Substances 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 43
- 150000001768 cations Chemical class 0.000 claims description 39
- 125000000732 arylene group Chemical group 0.000 claims description 37
- 238000005342 ion exchange Methods 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- -1 Chelex Polymers 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 125000005549 heteroarylene group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 22
- 125000003107 substituted aryl group Chemical group 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims description 18
- 125000006294 amino alkylene group Chemical group 0.000 claims description 16
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000012736 aqueous medium Substances 0.000 claims description 10
- 125000001118 alkylidene group Chemical group 0.000 claims description 7
- 125000005647 linker group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000003365 glass fiber Substances 0.000 claims description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical class C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 claims description 3
- 239000004925 Acrylic resin Substances 0.000 claims description 3
- 229920000178 Acrylic resin Polymers 0.000 claims description 3
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
- 238000010248 power generation Methods 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000006502 nitrobenzyl group Chemical group 0.000 claims 1
- 239000002253 acid Substances 0.000 description 223
- 150000007513 acids Chemical class 0.000 description 83
- 238000006243 chemical reaction Methods 0.000 description 33
- 150000002923 oximes Chemical class 0.000 description 32
- 150000002500 ions Chemical class 0.000 description 31
- 125000006850 spacer group Chemical group 0.000 description 30
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 29
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 29
- 239000000463 material Substances 0.000 description 28
- 239000010949 copper Substances 0.000 description 27
- 229910021645 metal ion Inorganic materials 0.000 description 24
- 239000013522 chelant Substances 0.000 description 22
- 230000009920 chelation Effects 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- 239000003153 chemical reaction reagent Substances 0.000 description 17
- 238000000605 extraction Methods 0.000 description 17
- 125000000524 functional group Chemical group 0.000 description 17
- XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 125000003544 oxime group Chemical group 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 238000010668 complexation reaction Methods 0.000 description 14
- 230000027455 binding Effects 0.000 description 13
- 230000006870 function Effects 0.000 description 13
- 230000007935 neutral effect Effects 0.000 description 13
- 239000002243 precursor Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 12
- 150000007942 carboxylates Chemical group 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 11
- 230000008901 benefit Effects 0.000 description 11
- 238000010168 coupling process Methods 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 239000002699 waste material Substances 0.000 description 11
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 10
- 238000013459 approach Methods 0.000 description 10
- 230000008878 coupling Effects 0.000 description 10
- 238000004132 cross linking Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 150000002739 metals Chemical class 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000000499 gel Substances 0.000 description 8
- 229910052759 nickel Inorganic materials 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 230000008929 regeneration Effects 0.000 description 8
- 238000011069 regeneration method Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical class [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 125000003368 amide group Chemical group 0.000 description 7
- 239000011324 bead Substances 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000000638 solvent extraction Methods 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000001212 derivatisation Methods 0.000 description 6
- 238000007306 functionalization reaction Methods 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 6
- 229920003303 ion-exchange polymer Polymers 0.000 description 6
- 238000007034 nitrosation reaction Methods 0.000 description 6
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical class OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000013467 fragmentation Methods 0.000 description 5
- 238000006062 fragmentation reaction Methods 0.000 description 5
- 229910052747 lanthanoid Inorganic materials 0.000 description 5
- 150000002602 lanthanoids Chemical class 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910001453 nickel ion Inorganic materials 0.000 description 5
- 230000009935 nitrosation Effects 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229920005990 polystyrene resin Polymers 0.000 description 5
- 239000012508 resin bead Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- 229910052768 actinide Inorganic materials 0.000 description 4
- 150000001255 actinides Chemical class 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000002843 carboxylic acid group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000008139 complexing agent Substances 0.000 description 4
- 239000000356 contaminant Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 4
- 235000019392 nitrosyl chloride Nutrition 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000004611 spectroscopical analysis Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- 238000005642 Gabriel synthesis reaction Methods 0.000 description 3
- 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 3
- 239000004157 Nitrosyl chloride Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 229920003180 amino resin Polymers 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000020335 dealkylation Effects 0.000 description 3
- 238000006900 dealkylation reaction Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 3
- 239000003344 environmental pollutant Substances 0.000 description 3
- 238000000705 flame atomic absorption spectrometry Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
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- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 3
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- 239000000047 product Substances 0.000 description 3
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- CAFXGFHPOQBGJP-QHHAFSJGSA-N (2e)-2-cyano-2-hydroxyiminoacetamide Chemical compound NC(=O)C(=N\O)\C#N CAFXGFHPOQBGJP-QHHAFSJGSA-N 0.000 description 2
- CNEFRTDDIMNTHC-GORDUTHDSA-N (2e)-2-cyano-2-hydroxyiminoacetic acid Chemical compound O\N=C(/C#N)C(O)=O CNEFRTDDIMNTHC-GORDUTHDSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- QDSFNOHWQKVVEB-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)morpholine Chemical compound CCOP(=O)(OCC)CN1CCOCC1 QDSFNOHWQKVVEB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
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- 230000005526 G1 to G0 transition Effects 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
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- 235000011180 diphosphates Nutrition 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
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- 125000004185 ester group Chemical group 0.000 description 2
- ZFKJVJIDPQDDFY-UHFFFAOYSA-N fluorescamine Chemical compound C12=CC=CC=C2C(=O)OC1(C1=O)OC=C1C1=CC=CC=C1 ZFKJVJIDPQDDFY-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
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- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000000622 liquid--liquid extraction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 2
- 125000004492 methyl ester group Chemical group 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 150000002815 nickel Chemical class 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 2
- 230000026731 phosphorylation Effects 0.000 description 2
- 238000006366 phosphorylation reaction Methods 0.000 description 2
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 229940093635 tributyl phosphate Drugs 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 230000005428 wave function Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/40—Introducing phosphorus atoms or phosphorus-containing groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J45/00—Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming ion-exchange properties
-
- 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
-
- 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)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/42—Treatment of water, waste water, or sewage by ion-exchange
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S210/00—Liquid purification or separation
- Y10S210/902—Materials removed
- Y10S210/911—Cumulative poison
- Y10S210/912—Heavy metal
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)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Treatment Of Water By Ion Exchange (AREA)
- Water Treatment By Sorption (AREA)
- Processing Of Solid Wastes (AREA)
- Removal Of Specific Substances (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/957,553 US7527733B2 (en) | 2004-09-30 | 2004-09-30 | Chelating agents for heavy metal removal |
| US10/957,553 | 2004-09-30 | ||
| PCT/US2005/034420 WO2006039235A2 (en) | 2004-09-30 | 2005-09-23 | Chelating agents for heavy metal removal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2005292337A1 true AU2005292337A1 (en) | 2006-04-13 |
Family
ID=36097816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005292337A Abandoned AU2005292337A1 (en) | 2004-09-30 | 2005-09-23 | Chelating agents for heavy metal removal |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7527733B2 (enExample) |
| EP (1) | EP1794092A4 (enExample) |
| JP (1) | JP2008514419A (enExample) |
| KR (1) | KR20070085280A (enExample) |
| CN (1) | CN101065330A (enExample) |
| AU (1) | AU2005292337A1 (enExample) |
| BR (1) | BRPI0516862A (enExample) |
| CA (1) | CA2581913A1 (enExample) |
| MX (1) | MX2007003681A (enExample) |
| RU (1) | RU2007116105A (enExample) |
| WO (1) | WO2006039235A2 (enExample) |
| ZA (1) | ZA200702660B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7674384B2 (en) * | 2003-07-18 | 2010-03-09 | Bj Services Company | Method of reclaiming brine solutions using an organic chelant |
| US7678281B2 (en) * | 2003-07-18 | 2010-03-16 | Bj Services Company | Method of reclaiming brine solutions using an organic chelant |
| US8874145B2 (en) * | 2006-08-02 | 2014-10-28 | Telecommunication Systems, Inc. | Personal location code broker |
| EP2158039A2 (en) * | 2007-05-31 | 2010-03-03 | Dow Italia S.R.L. | Process for the recovery of oxidation catalyst using ion exchange resins |
| US7947130B2 (en) * | 2009-10-24 | 2011-05-24 | Wai Mun Lee | Troika acid semiconductor cleaning compositions and methods of use |
| WO2011109521A1 (en) * | 2010-03-02 | 2011-09-09 | University Of Kansas | Polyamine-dihydroxybenzoic acid conjugate hydrogels as iron chelators |
| US8663460B2 (en) | 2010-09-16 | 2014-03-04 | Chevron U.S.A. Inc. | Process, method, and system for removing heavy metals from fluids |
| US8673133B2 (en) | 2010-09-16 | 2014-03-18 | Chevron U.S.A. Inc. | Process, method, and system for removing heavy metals from fluids |
| US8702975B2 (en) * | 2010-09-16 | 2014-04-22 | Chevron U.S.A. Inc. | Process, method, and system for removing heavy metals from fluids |
| US8728304B2 (en) | 2010-09-16 | 2014-05-20 | Chevron U.S.A. Inc. | Process, method, and system for removing heavy metals from fluids |
| US8975340B2 (en) | 2010-12-15 | 2015-03-10 | Electric Power Research Institute, Inc. | Synthesis of sequestration resins for water treatment in light water reactors |
| US9214248B2 (en) | 2010-12-15 | 2015-12-15 | Electric Power Research Institute, Inc. | Capture and removal of radioactive species from an aqueous solution |
| US9589690B2 (en) * | 2010-12-15 | 2017-03-07 | Electric Power Research Institute, Inc. | Light water reactor primary coolant activity cleanup |
| CN103157445A (zh) * | 2013-02-25 | 2013-06-19 | 武汉纺织大学 | 一种聚合物负载的金属盐配位萃取剂及其制备与应用 |
| CN108531563A (zh) * | 2018-02-05 | 2018-09-14 | 深圳市尚维高科有限公司 | 多孔微球的用途及裂解液以及裂解液的使用方法 |
| CN109502873B (zh) * | 2018-11-16 | 2021-11-16 | 西北矿冶研究院 | 一种处理废水中重金属离子的装置及方法 |
| CN110693076A (zh) * | 2019-08-07 | 2020-01-17 | 常德华馥生物技术有限公司 | 降低烟草浸膏中Pb和As含量的方法 |
| CN110372081A (zh) * | 2019-08-16 | 2019-10-25 | 重庆工程职业技术学院 | 工业废水重金属处理池 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1004398A1 (ru) * | 1981-09-18 | 1983-03-15 | Московский ордена Ленина и ордена Трудового Красного Знамени химико-технологический институт им.Д.И.Менделеева | 0,0-Дибутилоксиминоцианметилфосфонат в качестве экстрагента переходных металлов и способ его получени |
| US4952321A (en) * | 1988-10-07 | 1990-08-28 | Brigham Young University | Process of removing and concentrating desired ions from solutions |
| US5182251A (en) * | 1991-10-10 | 1993-01-26 | Brigham Young University | Aminoalkylphosphonic acid containing ligands attached to solid supports for removal of metal ions |
| JP3518112B2 (ja) * | 1995-12-06 | 2004-04-12 | 東京瓦斯株式会社 | 燃料電池の水処理装置 |
| US5948931A (en) * | 1996-07-12 | 1999-09-07 | University Of Southern California | Preparation and use of α-(hydroxyimino) phosphonoacetic acids |
| US5804606A (en) * | 1997-04-21 | 1998-09-08 | Rohm & Haas Company | Chelating resins |
| US6232265B1 (en) * | 1999-06-11 | 2001-05-15 | Ibc Advanced Technologies, Inc. | Particulate solid supports functionalized with polyhydroxypyridinone ligands |
| DE60026723T2 (de) | 1999-09-27 | 2007-03-29 | IBC Advanced Technologies, Inc., American Fork | Polyamid enthaltende und kovalent an einen Träger gebundene Liganden, Polyamid enthaltende Harze und Verfahren zur Entfernung von Metallen aus Lösungen |
| GB0025502D0 (en) * | 2000-10-18 | 2000-11-29 | Johnson Matthey Plc | Metal scavenging |
| JP2004000874A (ja) * | 2002-04-05 | 2004-01-08 | Toyobo Co Ltd | 溶液中の金属イオン濾過装置 |
-
2004
- 2004-09-30 US US10/957,553 patent/US7527733B2/en not_active Expired - Fee Related
-
2005
- 2005-09-23 EP EP05801898A patent/EP1794092A4/en not_active Withdrawn
- 2005-09-23 MX MX2007003681A patent/MX2007003681A/es not_active Application Discontinuation
- 2005-09-23 BR BRPI0516862-7A patent/BRPI0516862A/pt not_active IP Right Cessation
- 2005-09-23 JP JP2007534688A patent/JP2008514419A/ja active Pending
- 2005-09-23 CA CA002581913A patent/CA2581913A1/en not_active Abandoned
- 2005-09-23 AU AU2005292337A patent/AU2005292337A1/en not_active Abandoned
- 2005-09-23 KR KR1020077009155A patent/KR20070085280A/ko not_active Withdrawn
- 2005-09-23 WO PCT/US2005/034420 patent/WO2006039235A2/en not_active Ceased
- 2005-09-23 RU RU2007116105/04A patent/RU2007116105A/ru not_active Application Discontinuation
- 2005-09-23 CN CNA2005800407356A patent/CN101065330A/zh active Pending
-
2007
- 2007-03-29 ZA ZA200702660A patent/ZA200702660B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2007116105A (ru) | 2008-11-10 |
| JP2008514419A (ja) | 2008-05-08 |
| EP1794092A2 (en) | 2007-06-13 |
| US20060065604A1 (en) | 2006-03-30 |
| US7527733B2 (en) | 2009-05-05 |
| CA2581913A1 (en) | 2006-04-13 |
| MX2007003681A (es) | 2007-05-21 |
| EP1794092A4 (en) | 2011-08-10 |
| WO2006039235A3 (en) | 2006-08-31 |
| CN101065330A (zh) | 2007-10-31 |
| WO2006039235A2 (en) | 2006-04-13 |
| BRPI0516862A (pt) | 2008-09-23 |
| KR20070085280A (ko) | 2007-08-27 |
| ZA200702660B (en) | 2008-08-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |