JP5226701B2 - 水からフッ素性化学物質を除去するためのシステム及びプロセス - Google Patents
水からフッ素性化学物質を除去するためのシステム及びプロセス Download PDFInfo
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- JP5226701B2 JP5226701B2 JP2009550143A JP2009550143A JP5226701B2 JP 5226701 B2 JP5226701 B2 JP 5226701B2 JP 2009550143 A JP2009550143 A JP 2009550143A JP 2009550143 A JP2009550143 A JP 2009550143A JP 5226701 B2 JP5226701 B2 JP 5226701B2
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- water
- ion exchange
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- exchange resin
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 90
- 239000000126 substance Substances 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 33
- 230000008569 process Effects 0.000 title claims description 17
- 239000003456 ion exchange resin Substances 0.000 claims description 57
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 57
- 239000011347 resin Substances 0.000 claims description 40
- 229920005989 resin Polymers 0.000 claims description 40
- 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 claims description 36
- 125000000524 functional group Chemical group 0.000 claims description 21
- 150000001412 amines Chemical group 0.000 claims description 18
- 239000011159 matrix material Substances 0.000 claims description 15
- 239000003463 adsorbent Substances 0.000 description 63
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 48
- 238000005342 ion exchange Methods 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000001179 sorption measurement Methods 0.000 description 15
- 150000002430 hydrocarbons Chemical group 0.000 description 14
- YFSUTJLHUFNCNZ-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-M 0.000 description 13
- SNGREZUHAYWORS-UHFFFAOYSA-M 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoate Chemical compound [O-]C(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-M 0.000 description 13
- 239000000523 sample Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- YPJUNDFVDDCYIH-UHFFFAOYSA-M 2,2,3,3,4,4,4-heptafluorobutanoate Chemical compound [O-]C(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-M 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- -1 halocarbon compound Chemical class 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- QZHDEAJFRJCDMF-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QZHDEAJFRJCDMF-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000274 adsorptive effect Effects 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000008399 tap water Substances 0.000 description 3
- 235000020679 tap water Nutrition 0.000 description 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000012039 electrophile Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920000307 polymer substrate Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000010414 supernatant solution Substances 0.000 description 2
- 239000002352 surface water Substances 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- GFZPUWKGPNHWHD-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluoro-n-methylbutane-1-sulfonamide Chemical compound CNS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F GFZPUWKGPNHWHD-UHFFFAOYSA-N 0.000 description 1
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 1
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 1
- GRJRKPMIRMSBNK-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctan-1-ol Chemical compound OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F GRJRKPMIRMSBNK-UHFFFAOYSA-N 0.000 description 1
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 102100027667 Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 2 Human genes 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 101000725947 Homo sapiens Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 2 Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910001748 carbonate mineral Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- JNTNNUXPPZAEFD-UHFFFAOYSA-N n-amino-n-propylformamide Chemical compound CCCN(N)C=O JNTNNUXPPZAEFD-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012508 resin bead Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 238000012421 spiking Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
-
- 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
-
- 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
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/04—Processes using organic exchangers
-
- 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
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/04—Processes using organic exchangers
- B01J41/05—Processes using organic exchangers in the strongly basic form
-
- 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
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/08—Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/12—Macromolecular compounds
-
- 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
- C02F1/58—Treatment of water, waste water, or sewage by removing specified dissolved compounds
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/10—Inorganic compounds
- C02F2101/12—Halogens or halogen-containing compounds
- C02F2101/14—Fluorine or fluorine-containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Hydrology & Water Resources (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Water Treatment By Sorption (AREA)
- Treatment Of Water By Ion Exchange (AREA)
Description
イオン交換樹脂を含有する容器であって、そのイオン交換樹脂は、官能基が結合した不溶性のマトリックスを含み、その官能基が式:
−N(R1R2R3)
(式中、
Nは窒素であり;
R1、R2及びR3は炭化水素基であり、同一又は異なって、直鎖状、分枝状であることができ、及び/又は部分的若しくは完全に置換(例えば、フッ素化)されてもよく、C1以上の炭素鎖長を有してもよく、その炭化水素鎖は、任意に極性基(例えば、O、N、S)を含む)のアミンを含む容器と;
水の流れを容器に向け、それによってイオン交換樹脂と接触させる入口と;
水の流れを容器の外に向ける出口と;を含む。
フッ素性化学物質を含む水をイオン交換樹脂に曝す工程であって、その樹脂は、官能基が結合した不溶性のマトリックスを含み、その官能基は式:
−N(R1R2R3)
(式中、
Nは窒素であり;
R1、R2及びR3は炭化水素基であり、同一又は異なって、直鎖状、分枝状であることができ、及び/又は部分的若しくは完全に置換(例えば、フッ素化)されてもよく、C1以上の炭素鎖長を有してもよく、その炭化水素鎖は、任意に極性基(例えば、O、N、S)を含む)のアミンを含む工程と;
一定期間水を樹脂に接触させ続ける工程と;
水を樹脂から分離する工程と;を含む。
−N(R1R2R3) I
(式中、
Nは窒素であり;
R1、R2及びR3は炭化水素基であり、同一又は異なって、直鎖状、分枝状であることができ及び/又は部分的若しくは完全に置換(例えば、フッ素化)されてもよく、C1以上の炭素鎖長を有していてもよく、その炭化水素鎖は、任意に極性基(例えば、O、N、S)を含む)の1以上の四級アミンが挙げられる。
R1、R2、R3は先に記載された通りである。)
R1、R2、R3は先に記載した通りであり;
Xはハロゲンである。)
手順1:バッチ等温線方法
表1に列挙される各吸着剤について、60mLのプラスチック遠心管にて試験水中の所与の吸着剤溶液を調製した。溶液を水中で4〜5種の異なる吸着剤濃度で調製した。2つの実験用水サンプルである「水道水」サンプル(表2)及び「地表水」サンプル(表3)を調製した。PFBA、PFBS、PFOA及びPFOSにイオン化する酸は、VWR(ペンシルベニア州ウエストチェスター(West Chester))から得てもよい。水(水道水又は地表水)と吸着剤との混合物を調製し、振とう器に入れ、20℃にて34〜95時間平衡化した。次いでサンプルを遠心分離し、上澄み溶液のサンプルを液体クロマトグラフィー/質量分光法(LC/MC)を用いる分析用に保存した。
C初期=吸着実験前の水に存在する所与の化合物の初期濃度(ng/mL)。
Cs=所与の化合物の吸着された濃度(ng/gm)。
K=平衡吸着係数、それをプロットのY切片から決定する。
表1に列挙される吸着剤の溶液を調製し、表2にあるように配合された水を用いて手順1に従って試験した。吸着剤の濃度は、表4に記載される通りであった。カルゴン(Calgon)F600吸着剤(活性炭)を比較例として含めた。
吸着剤ダウ(Dow)NSR−1、ダウPSR−2、ダウPSR−3、及びカルゴン(Calgon)F600活性炭のそれぞれの溶液を調製し、表2のように配合された水を用いて手順1に従って試験した。吸着剤の濃度は、表5に記載される通りであった。カルゴン(Calgon)F600吸着剤(活性炭)を比較例として含めた。
吸着剤ダウ(Dow)NSR−1、ダウPSR−2、ダウPSR−3、及びカルゴン(Calgon)F600のそれぞれの溶液を調製し、表2のような水を用いて手順1に従って試験した。吸着剤の濃度は、表6に記載される通りであった。カルゴン(Calgon)F600吸着剤(活性炭)を比較例として含めた。
吸着剤ダウ(Dow)PSR2、カルゴン(Calgon)F600及びノリット(Norit)830RSのそれぞれの溶液を調製し、表3のように配合された水を用いて手順1に従って試験した。吸着剤の濃度は、表7に記載される通りであった。カルゴン(Calgon)F600及びノリット(Norit)830RS吸着剤(活性炭)を比較例として含んだ。
3つのイオン交換樹脂又は吸着剤を使用した:ダウエックス(Dowex)1、ダウNSR−1、及びダウPSR−2。3つのイオン交換カラムを調製したが、それぞれが一連のサンプリングポートA〜Nを有し、各サンプリングポート間の距離は5cmであった。各カラムの内側に詰められた床の長さは71cmであり、各カラムの直径は3.2cmであった。各カラムの空容量は571mLであった。
実施例6〜20におけるイオン交換樹脂の調製のために使用される材料を表9に示す。
イオン交換樹脂を調製した。磁性攪拌棒を備えた250mLの丸底フラスコに、ダウ(Dow)XVRクロロメチルスチレン樹脂、30.0g(66meq、2.2meq/g)、トリ−n−オクチルアミン、23.34g(66meq)、及び150mLのN,N−ジメチルホルムアミドを充填し、窒素下にて攪拌しながら90℃の加熱浴に48時間置いた。「C」多孔性フリットブフナー漏斗を用いて溶媒を濾過し、続いて約100mLの水、50mLのイソプロパノール、100mLの水、及び250mLのメチル−t−ブチルエーテルで連続的に樹脂を洗浄し、その樹脂を120℃にて約30分間乾燥させることによって、樹脂を反応混合物から単離した。出発物質及び反応条件を表10に要約する。
イオン交換樹脂を実施例6に記載される手順と同様の手順を用いて調製した。出発物質及び反応条件を表10に示す。
(i)官能基中間体の合成及び(ii)四級アミンを形成するためのその後の樹脂との反応を含む2工程手順にてイオン交換樹脂を調製した。
(i)官能基中間体の合成及び(ii)四級アミンを形成するためのその後の樹脂との反応を含む2工程手順にてイオン交換樹脂を調製した。
(i)官能基中間体の合成及び(ii)四級アミンを形成するためのその後の樹脂との反応を含む2つの別個の工程にてイオン交換樹脂を調製した。その手順は、実施例18の調製に記載されるものと同様であった。出発物質及び反応条件を表10に示す。
イオン交換樹脂を実施例6と同様に調製した。出発物質及び反応条件を表10に示す。
実施例21はダウエックス(Dowex)PSR3吸着剤であった。
実施例22は、プロライト社(Purolite Company)(ペンシルベニア州フィラデルフィア)から得られたプロライト(Purolite)A530E吸着剤であった。
実施例23は、シリサイクル(Silicycle)(カナダ、ケベック)から得られたシリサイクル(Silicycle)TBAクロライド吸着剤であった。
手順2:吸着能
実施例6〜23の吸着剤溶液を調製した。吸着剤及び水をプラスチック遠心管に入れ、一連の水中吸着剤濃度を与えた。全ての管は水中にて同じ初期濃度のフッ素性化学物質を含有していた。水及び吸着剤の混合物を含有する管をオービタルシェイカーに入れ、20℃にて少なくとも44〜48時間振とうした。その後、吸着剤サンプルを遠心分離した。上澄み溶液のサンプルを採取し、LC/MSにより分析して、吸着剤と名目上平衡化した水中の個々のフッ素性化学物質の濃度を測定した。3つの遠心管を同じ初期溶液で満たすが、吸着剤は入れなかった。これらのサンプルを使用して初期濃度を測定した。これらのデータから、吸着剤に吸着された所与のフッ素性化学物質の質量を測定し、その値を遠心管に添加された乾燥吸着剤の質量に対して規格化した。これらのデータを使用して、量(吸着された質量/吸着剤質量)対見かけの平衡フッ素性化学物質濃度の等温線プロットを構築した。対象吸着剤投与量を表11に要約する。
CLMS=LMSサンプルの分析にて観測される所与の化学物質の濃度(ng/mL)。
C初期=吸着実験前の水に存在する所与の化合物の初期濃度(ng/mL)。
Cs=所与の化合物の吸着された濃度(ng/gm)。
K=平衡吸着係数、それをプロットのY切片から決定する。
1/n=プロットの傾き。n=1である場合、等温線は直線であると言える。)
Claims (2)
- 水からフッ素性化学物質を除去するためのシステムであって、
イオン交換樹脂を含有する容器であって、前記イオン交換樹脂は、官能基が結合した不溶性のマトリックスを含み、前記官能基は、−N(CH 3 ) 2 (C 6 H 13 )、−N(CH 3 ) 2 (C 12 H 25 )、−N(CH 3 ) 2 (C 16 H 33 )、−N(CH 3 ) 2 (C 18 H 37 )、−N(CH 3 ) 2 CH 2 CH 2 C 6 F 13 、−N(CH 3 ) 2 CH 2 CH 2 N(CH 3 )SO 2 C 4 F 9 、及び前述の2以上の組み合わせからなる群より選択される四級アミンを含む容器を含む、システム。 - 水からフッ素性化学物質を除去するためのプロセスであって、
フッ素性化学物質を含む水をイオン交換樹脂に曝す工程であって、前記樹脂が、官能基が結合した不溶性のマトリックスを含み、前記官能基は、−N(CH 3 ) 2 (C 6 H 13 )、−N(CH 3 ) 2 (C 12 H 25 )、−N(CH 3 ) 2 (C 16 H 33 )、−N(CH 3 ) 2 (C 18 H 37 )、−N(CH 3 ) 2 CH 2 CH 2 C 6 F 13 、−N(CH 3 ) 2 CH 2 CH 2 N(CH 3 )SO 2 C 4 F 9 、及び前述の2以上の組み合わせからなる群より選択される四級アミンを含む工程と;
一定期間前記水を前記樹脂に接触させ続ける工程と;
前記水を前記樹脂から分離する工程と;を含むプロセス。
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2008
- 2008-02-15 EP EP08729935A patent/EP2132143B1/en active Active
- 2008-02-15 US US12/520,697 patent/US20100084343A1/en not_active Abandoned
- 2008-02-15 CN CN2008800043404A patent/CN101605728B/zh not_active Expired - Fee Related
- 2008-02-15 JP JP2009550143A patent/JP5226701B2/ja active Active
- 2008-02-15 KR KR1020097017455A patent/KR101500018B1/ko not_active IP Right Cessation
- 2008-02-15 BR BRPI0807109-8A patent/BRPI0807109A2/pt not_active IP Right Cessation
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JP2010519018A (ja) | 2010-06-03 |
KR20090119861A (ko) | 2009-11-20 |
US20100084343A1 (en) | 2010-04-08 |
CN101605728A (zh) | 2009-12-16 |
WO2008101137A1 (en) | 2008-08-21 |
EP2132143A1 (en) | 2009-12-16 |
KR101500018B1 (ko) | 2015-03-06 |
BRPI0807109A2 (pt) | 2014-05-06 |
EP2132143B1 (en) | 2012-12-26 |
CN101605728B (zh) | 2013-07-24 |
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