CA2030596C - Procede pour la selection et la concentration de certaines molecules en solution - Google Patents

Procede pour la selection et la concentration de certaines molecules en solution Download PDF

Info

Publication number: CA2030596C
Authority: CA; Canada
Prior art keywords: cation; ligand; molecules; matrix; group
Prior art date: 1990-11-23
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.): Expired - Fee Related

Application number

CA002030596A

Other languages

English (en)

Other versions

CA2030596A1 (fr

Inventor

Jerald S. Bradshaw

Bryon J. Tarbet

Ronald L. Bruening

Reed M. Izatt

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Brigham Young University

Original Assignee

Brigham Young University

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.)

1990-11-23

Filing date

1990-11-23

Publication date

2003-08-12

1990-11-23 Application filed by Brigham Young University filed Critical Brigham Young University

1990-11-23 Priority to CA002030596A priority Critical patent/CA2030596C/fr

1992-05-24 Publication of CA2030596A1 publication Critical patent/CA2030596A1/fr

2003-08-12 Application granted granted Critical

2003-08-12 Publication of CA2030596C publication Critical patent/CA2030596C/fr

2010-11-23 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 56
239000011159 matrix material Substances 0.000 claims abstract description 79
239000003446 ligand Substances 0.000 claims abstract description 72
150000001768 cations Chemical class 0.000 claims abstract description 61
239000007787 solid Substances 0.000 claims abstract description 41
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 22
150000001413 amino acids Chemical class 0.000 claims abstract description 21
125000006850 spacer group Chemical group 0.000 claims abstract description 19
239000007789 gas Substances 0.000 claims abstract description 17
150000001450 anions Chemical class 0.000 claims abstract description 16
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052710 silicon Inorganic materials 0.000 claims abstract description 10
229910021529 ammonia Inorganic materials 0.000 claims abstract description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 25
-1 Au3+ Chemical compound 0.000 claims description 23
229940024606 amino acid Drugs 0.000 claims description 19
235000001014 amino acid Nutrition 0.000 claims description 19
239000007788 liquid Substances 0.000 claims description 19
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 17
239000002184 metal Substances 0.000 claims description 15
229910052751 metal Inorganic materials 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 15
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 14
239000000463 material Substances 0.000 claims description 11
229960004441 tyrosine Drugs 0.000 claims description 11
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 7
239000004471 Glycine Substances 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 7
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 6
DBUXSCUEGJMZAE-UHFFFAOYSA-N methylmercury(1+) Chemical compound [Hg+]C DBUXSCUEGJMZAE-UHFFFAOYSA-N 0.000 claims description 5
239000010703 silicon Substances 0.000 claims description 5
BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 5
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 5
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 4
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
229930182817 methionine Natural products 0.000 claims description 3
230000007935 neutral effect Effects 0.000 claims description 3
229910000480 nickel oxide Inorganic materials 0.000 claims description 3
GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 claims description 3
239000000377 silicon dioxide Substances 0.000 claims description 3
150000003568 thioethers Chemical class 0.000 claims description 3
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 2
JMFBXUMHVSZUKY-UHFFFAOYSA-N 3-bromopropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCBr JMFBXUMHVSZUKY-UHFFFAOYSA-N 0.000 claims description 2
SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 claims description 2
UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
239000004475 Arginine Substances 0.000 claims description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 2
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 2
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 2
AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 2
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 2
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 2
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 2
ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 2
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 2
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 2
KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 2
ZXOFHTCCTUEJQJ-UHFFFAOYSA-N [4-(chloromethyl)phenyl]-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(CCl)C=C1 ZXOFHTCCTUEJQJ-UHFFFAOYSA-N 0.000 claims description 2
235000004279 alanine Nutrition 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
235000003704 aspartic acid Nutrition 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000013522 chelant Substances 0.000 claims description 2
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 2
235000018417 cysteine Nutrition 0.000 claims description 2
RKNYOHXRCRXQOS-UHFFFAOYSA-N diethyl 2-(3-triethoxysilylpropyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)CCC[Si](OCC)(OCC)OCC RKNYOHXRCRXQOS-UHFFFAOYSA-N 0.000 claims description 2
FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 2
OUDSFQBUEBFSPS-UHFFFAOYSA-N ethylenediaminetriacetic acid Chemical compound OC(=O)CNCCN(CC(O)=O)CC(O)=O OUDSFQBUEBFSPS-UHFFFAOYSA-N 0.000 claims description 2
235000013922 glutamic acid Nutrition 0.000 claims description 2
239000004220 glutamic acid Substances 0.000 claims description 2
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims description 2
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 2
229960000310 isoleucine Drugs 0.000 claims description 2
AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims description 2
MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 2
150000002923 oximes Chemical class 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 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
150000003222 pyridines Chemical class 0.000 claims description 2
150000003573 thiols Chemical class 0.000 claims description 2
239000004474 valine Substances 0.000 claims description 2
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 1
229910002092 carbon dioxide Inorganic materials 0.000 claims 1
239000001569 carbon dioxide Substances 0.000 claims 1
229910002091 carbon monoxide Inorganic materials 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims 1
229940006461 iodide ion Drugs 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
239000001272 nitrous oxide Substances 0.000 claims 1
125000001824 selenocyanato group Chemical group *[Se]C#N 0.000 claims 1
125000005415 substituted alkoxy group Chemical group 0.000 claims 1
125000000547 substituted alkyl group Chemical group 0.000 claims 1
238000000926 separation method Methods 0.000 abstract description 28
238000011084 recovery Methods 0.000 abstract description 17
150000002500 ions Chemical class 0.000 abstract description 14
229910001868 water Inorganic materials 0.000 abstract description 10
238000002360 preparation method Methods 0.000 abstract description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract description 3
239000011780 sodium chloride Substances 0.000 abstract description 3
231100000331 toxic Toxicity 0.000 abstract description 3
230000002588 toxic effect Effects 0.000 abstract description 3
150000003839 salts Chemical class 0.000 abstract description 2
ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 abstract 1
239000000243 solution Substances 0.000 description 80
239000000741 silica gel Substances 0.000 description 23
229910002027 silica gel Inorganic materials 0.000 description 23
238000004458 analytical method Methods 0.000 description 12
239000011343 solid material Substances 0.000 description 11
239000003153 chemical reaction reagent Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000000536 complexating effect Effects 0.000 description 8
238000001479 atomic absorption spectroscopy Methods 0.000 description 7
239000008139 complexing agent Substances 0.000 description 7
150000001875 compounds Chemical class 0.000 description 7
238000002156 mixing Methods 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
229940012017 ethylenediamine Drugs 0.000 description 6
238000011068 loading method Methods 0.000 description 5
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
238000010668 complexation reaction Methods 0.000 description 4
239000010949 copper Substances 0.000 description 4
229910000069 nitrogen hydride Inorganic materials 0.000 description 4
KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
230000003993 interaction Effects 0.000 description 3
230000033116 oxidation-reduction process Effects 0.000 description 3
150000004756 silanes Chemical class 0.000 description 3
DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000004737 colorimetric analysis Methods 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
238000005342 ion exchange Methods 0.000 description 2
229910001629 magnesium chloride Inorganic materials 0.000 description 2
229910021645 metal ion Inorganic materials 0.000 description 2
150000002739 metals Chemical group 0.000 description 2
239000013110 organic ligand Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
229920002223 polystyrene Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
DLNIYCJLCUQJMS-UHFFFAOYSA-N 1,2,5-oxadithiolane Chemical compound C1CSOS1 DLNIYCJLCUQJMS-UHFFFAOYSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical group C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
241000251468 Actinopterygii Species 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
241000854350 Enicospilus group Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
229910017974 NH40H Inorganic materials 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
239000006087 Silane Coupling Agent Substances 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000001243 acetic acids Chemical class 0.000 description 1
238000007605 air drying Methods 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000002738 chelating agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 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
239000003086 colorant Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Inorganic materials [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 1
ORMNPSYMZOGSSV-UHFFFAOYSA-N mercury(II) nitrate Inorganic materials [Hg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ORMNPSYMZOGSSV-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000011368 organic material Substances 0.000 description 1
GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(II) nitrate Inorganic materials [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
238000003825 pressing Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000004576 sand Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Landscapes

Solid-Sorbent Or Filter-Aiding Compositions (AREA)

CA002030596A 1990-11-23 1990-11-23 Procede pour la selection et la concentration de certaines molecules en solution Expired - Fee Related CA2030596C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA002030596A CA2030596C (fr)	1990-11-23	1990-11-23	Procede pour la selection et la concentration de certaines molecules en solution

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA002030596A CA2030596C (fr)	1990-11-23	1990-11-23	Procede pour la selection et la concentration de certaines molecules en solution

Publications (2)

Publication Number	Publication Date
CA2030596A1 CA2030596A1 (fr)	1992-05-24
CA2030596C true CA2030596C (fr)	2003-08-12

Family

ID=4146501

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002030596A Expired - Fee Related CA2030596C (fr)	1990-11-23	1990-11-23	Procede pour la selection et la concentration de certaines molecules en solution

Country Status (1)

Country	Link
CA (1)	CA2030596C (fr)

1990
- 1990-11-23 CA CA002030596A patent/CA2030596C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2030596A1 (fr)	1992-05-24

Publication	Publication Date	Title
US5250188A (en)	1993-10-05	Process of removing and concentrating desired molecules from solutions
EP0487775A1 (fr)	1992-06-03	Procédé pour enlever et concentrer des molécules désirées de solutions
EP0641252B1 (fr)	1997-12-17	Compositions et procedes de retrait, de separation et de concentration de certains ions de solutions
US5190660A (en)	1993-03-02	Ion complexation by silica-immobilized polyethyleneimines
US5078978A (en)	1992-01-07	Pyridine-containing alkoxysilanes bonded to inorganic supports and processes of using the same for removing and concentrating desired ions from solutions
AU661917B2 (en)	1995-08-10	Removing ions from solutions using sulphur containing hydrocarbon complex and electron withdrawing groups
EP0361060B1 (fr)	1992-01-08	Composés d'hydrocarbures contenant du soufre et de l'azote et procédé les utilisant dans la récupération et la concentration d'ions désirés de solutions les contenant
AU692266B2 (en)	1998-06-04	Immobilised branched polyalkyleneimines
US5084430A (en)	1992-01-28	Sulfur and nitrogen containing hydrocarbons and process of using same in separating desired ions from solutions thereof
JPH06508338A (ja)	1994-09-22	ロジウム、イリジウム及びルテニウム溶液の処理方法
JP6079113B2 (ja)	2017-02-15	パラジウム分離剤、並びにその製造方法及び用途
US5817239A (en)	1998-10-06	Method of removing heavy metal ions from a liquid with chemically active ceramic compositions with an hydroxyquinoline moiety
WO1992017403A1 (fr)	1992-10-15	Acide polycarboxylique de polyalkylene-polyamine fixe a un support et extraction d'ions metalliques au moyen de cet element
CA2030596C (fr)	2003-08-12	Procede pour la selection et la concentration de certaines molecules en solution
AU639960B2 (en)	1993-08-12	Process of removing and concentrating desired molecules from solutions
CN115624957B (zh)	2023-04-07	一种改性功能化硅胶材料及其制备方法和应用
CN114277248B (zh)	2024-05-07	一种从铑铱置换渣中回收铑铱的方法
JPH04260448A (ja)	1992-09-16	溶液から所望の分子を分離および濃縮する方法
EP0480386B1 (fr)	1996-01-03	Ligands contenant du polytetraalkylammonium et une polytrialkylamine liés à un support inorganique et leur utilisation pour enlever ou concentrer certains ions en solutions
CN116004997A (zh)	2023-04-25	一种利用磁性mdm杂化材料循环回收贵金属的方法

Legal Events

Date	Code	Title	Description
1997-10-20	EEER	Examination request
2009-11-23	MKLA	Lapsed