JP4934569B2 - 有害化合物の無害化方法 - Google Patents
有害化合物の無害化方法 Download PDFInfo
- Publication number
- JP4934569B2 JP4934569B2 JP2007286374A JP2007286374A JP4934569B2 JP 4934569 B2 JP4934569 B2 JP 4934569B2 JP 2007286374 A JP2007286374 A JP 2007286374A JP 2007286374 A JP2007286374 A JP 2007286374A JP 4934569 B2 JP4934569 B2 JP 4934569B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- arsenic
- acid
- harmful
- reaction
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 title claims description 65
- 238000000034 method Methods 0.000 title claims description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 63
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 45
- 229910052785 arsenic Inorganic materials 0.000 claims description 44
- -1 carboxymethyl radical Chemical class 0.000 claims description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 20
- 229910052787 antimony Inorganic materials 0.000 claims description 19
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 18
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 16
- 229910052711 selenium Inorganic materials 0.000 claims description 16
- 239000011669 selenium Substances 0.000 claims description 16
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 14
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 12
- OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical compound C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 claims description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
- QYPPRTNMGCREIM-UHFFFAOYSA-N methylarsonic acid Chemical compound C[As](O)(O)=O QYPPRTNMGCREIM-UHFFFAOYSA-N 0.000 claims description 12
- 238000007069 methylation reaction Methods 0.000 claims description 12
- SPTHHTGLGVZZRH-UHFFFAOYSA-N Arsenobetaine Chemical compound C[As+](C)(C)CC([O-])=O SPTHHTGLGVZZRH-UHFFFAOYSA-N 0.000 claims description 10
- 238000005804 alkylation reaction Methods 0.000 claims description 10
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 9
- 235000019253 formic acid Nutrition 0.000 claims description 9
- 230000029936 alkylation Effects 0.000 claims description 8
- UNJPQTDTZAKTFK-UHFFFAOYSA-K cerium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Ce+3] UNJPQTDTZAKTFK-UHFFFAOYSA-K 0.000 claims description 7
- 229950004243 cacodylic acid Drugs 0.000 claims description 6
- 150000004700 cobalt complex Chemical class 0.000 claims description 6
- VDEGQTCMQUFPFH-UHFFFAOYSA-N hydroxy-dimethyl-arsine Natural products C[As](C)O VDEGQTCMQUFPFH-UHFFFAOYSA-N 0.000 claims description 6
- 230000011987 methylation Effects 0.000 claims description 6
- 235000019260 propionic acid Nutrition 0.000 claims description 6
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 6
- JWOWJQPAYGEFFK-UHFFFAOYSA-N trimethylarsine oxide Chemical compound C[As](C)(C)=O JWOWJQPAYGEFFK-UHFFFAOYSA-N 0.000 claims description 6
- ORLOBEXOFQEWFQ-UHFFFAOYSA-N arsenocholine Chemical compound C[As+](C)(C)CCO ORLOBEXOFQEWFQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 50
- 239000000243 solution Substances 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- 150000001495 arsenic compounds Chemical class 0.000 description 15
- 238000001784 detoxification Methods 0.000 description 13
- 238000001927 high performance liquid chromatography-inductively coupled plasma mass spectrometry Methods 0.000 description 11
- 229910021642 ultra pure water Inorganic materials 0.000 description 10
- 239000012498 ultrapure water Substances 0.000 description 10
- 239000010936 titanium Substances 0.000 description 8
- UYPYRKYUKCHHIB-UHFFFAOYSA-N trimethylamine N-oxide Chemical compound C[N+](C)(C)[O-] UYPYRKYUKCHHIB-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 6
- RMRCNWBMXRMIRW-BYFNXCQMSA-M cyanocobalamin Chemical compound N#C[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O RMRCNWBMXRMIRW-BYFNXCQMSA-M 0.000 description 6
- LVKZSFMYNWRPJX-UHFFFAOYSA-N phenylarsonic acid Chemical compound O[As](O)(=O)C1=CC=CC=C1 LVKZSFMYNWRPJX-UHFFFAOYSA-N 0.000 description 6
- 239000011941 photocatalyst Substances 0.000 description 6
- 229910010413 TiO 2 Inorganic materials 0.000 description 5
- 231100000252 nontoxic Toxicity 0.000 description 5
- 230000003000 nontoxic effect Effects 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229940093920 gynecological arsenic compound Drugs 0.000 description 4
- 229910001385 heavy metal Inorganic materials 0.000 description 4
- YOZNUFWCRFCGIH-BYFNXCQMSA-L hydroxocobalamin Chemical compound O[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O YOZNUFWCRFCGIH-BYFNXCQMSA-L 0.000 description 4
- 235000007672 methylcobalamin Nutrition 0.000 description 4
- 239000011585 methylcobalamin Substances 0.000 description 4
- HPEAEXLKYCYTSI-UHFFFAOYSA-N (4-hydroxy-3-nitrophenoxy)arsonic acid Chemical compound OC1=CC=C(O[As](O)(O)=O)C=C1[N+]([O-])=O HPEAEXLKYCYTSI-UHFFFAOYSA-N 0.000 description 3
- QPPZMBOQLBGPET-UHFFFAOYSA-N acetic acid;trimethylarsane Chemical compound C[As](C)C.CC(O)=O QPPZMBOQLBGPET-UHFFFAOYSA-N 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 235000000639 cyanocobalamin Nutrition 0.000 description 3
- 239000011666 cyanocobalamin Substances 0.000 description 3
- 229960002104 cyanocobalamin Drugs 0.000 description 3
- SKYRWWOGLYJNCD-UHFFFAOYSA-N diphenylarsinic acid Chemical compound C=1C=CC=CC=1[As](=O)(O)C1=CC=CC=C1 SKYRWWOGLYJNCD-UHFFFAOYSA-N 0.000 description 3
- JEWJRMKHSMTXPP-BYFNXCQMSA-M methylcobalamin Chemical compound C[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O JEWJRMKHSMTXPP-BYFNXCQMSA-M 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- HTDIUWINAKAPER-UHFFFAOYSA-N trimethylarsine Chemical compound C[As](C)C HTDIUWINAKAPER-UHFFFAOYSA-N 0.000 description 3
- HJTAZXHBEBIQQX-UHFFFAOYSA-N 1,5-bis(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1CCl HJTAZXHBEBIQQX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 231100000111 LD50 Toxicity 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- COHDHYZHOPQOFD-UHFFFAOYSA-N arsenic pentoxide Chemical compound O=[As](=O)O[As](=O)=O COHDHYZHOPQOFD-UHFFFAOYSA-N 0.000 description 2
- GOLCXWYRSKYTSP-UHFFFAOYSA-N arsenic trioxide Inorganic materials O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 description 2
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000004867 hydroxocobalamin Nutrition 0.000 description 2
- 239000011704 hydroxocobalamin Substances 0.000 description 2
- 229960001103 hydroxocobalamin Drugs 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- KRDDXSIKPQVLDP-UHFFFAOYSA-N methylarsenic Chemical compound [As]C KRDDXSIKPQVLDP-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- IEKVHGDUBCZHRB-UHFFFAOYSA-N phenylarsenic Chemical compound [As]C1=CC=CC=C1 IEKVHGDUBCZHRB-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- VFLXBUJKRRJAKY-UHFFFAOYSA-N 13768-86-0 Chemical compound O=[Se](=O)=O VFLXBUJKRRJAKY-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- KSFOVUSSGSKXFI-GAQDCDSVSA-N CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O Chemical compound CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O KSFOVUSSGSKXFI-GAQDCDSVSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229930003779 Vitamin B12 Natural products 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001462 antimony Chemical class 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 229940000488 arsenic acid Drugs 0.000 description 1
- OEYOHULQRFXULB-UHFFFAOYSA-N arsenic trichloride Chemical compound Cl[As](Cl)Cl OEYOHULQRFXULB-UHFFFAOYSA-N 0.000 description 1
- GCPXMJHSNVMWNM-UHFFFAOYSA-N arsenous acid Chemical compound O[As](O)O GCPXMJHSNVMWNM-UHFFFAOYSA-N 0.000 description 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- JABQEGNJAQHUMU-UHFFFAOYSA-N carboxymethyl(methyl)arsenic Chemical compound C[As]CC(O)=O JABQEGNJAQHUMU-UHFFFAOYSA-N 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
- HDINKIBQOCEUKW-UHFFFAOYSA-N chloroarsenic Chemical class [As]Cl HDINKIBQOCEUKW-UHFFFAOYSA-N 0.000 description 1
- 150000001867 cobalamins Chemical class 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- PCZWNUHBFITYKI-GAQUOPITSA-N cobalt 2,4-ditert-butyl-6-[[(1R,2R)-2-[(3,5-ditert-butyl-2-hydroxyphenyl)methylideneamino]cyclohexyl]iminomethyl]phenol Chemical compound [Co].CC(C)(C)C1=CC(C(C)(C)C)=CC(C=N[C@H]2[C@@H](CCCC2)N=CC=2C(=C(C=C(C=2)C(C)(C)C)C(C)(C)C)O)=C1O PCZWNUHBFITYKI-GAQUOPITSA-N 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 description 1
- ZFWPDJKMASHRPT-PNHSAAKESA-L cobalt(2+);2,4-ditert-butyl-6-[[(1s,2s)-2-[(3,5-ditert-butyl-2-oxidophenyl)methylideneamino]cyclohexyl]iminomethyl]phenolate Chemical compound [Co+2].CC(C)(C)C1=CC(C(C)(C)C)=CC(C=N[C@@H]2[C@H](CCCC2)N=CC=2C(=C(C=C(C=2)C(C)(C)C)C(C)(C)C)[O-])=C1[O-] ZFWPDJKMASHRPT-PNHSAAKESA-L 0.000 description 1
- QAEKNCDIHIGLFI-UHFFFAOYSA-L cobalt(2+);2-ethylhexanoate Chemical compound [Co+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O QAEKNCDIHIGLFI-UHFFFAOYSA-L 0.000 description 1
- HHZAIOOQYMFSFC-UHFFFAOYSA-L cobalt(2+);3-oxobutanoate Chemical compound [Co+2].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O HHZAIOOQYMFSFC-UHFFFAOYSA-L 0.000 description 1
- YBXHPSXGXLGNBR-UHFFFAOYSA-L cobalt(2+);4-cyclohexylbutanoate Chemical compound [Co+2].[O-]C(=O)CCCC1CCCCC1.[O-]C(=O)CCCC1CCCCC1 YBXHPSXGXLGNBR-UHFFFAOYSA-L 0.000 description 1
- LSZLYWSRWXFMOI-UHFFFAOYSA-N cobalt(2+);5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Co+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 LSZLYWSRWXFMOI-UHFFFAOYSA-N 0.000 description 1
- AGVAZMGAQJOSFJ-WZHZPDAFSA-M cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+2].N#[C-].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(O)(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O AGVAZMGAQJOSFJ-WZHZPDAFSA-M 0.000 description 1
- GAYAMOAYBXKUII-UHFFFAOYSA-L cobalt(2+);dibenzoate Chemical compound [Co+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 GAYAMOAYBXKUII-UHFFFAOYSA-L 0.000 description 1
- WLQXLCXXAPYDIU-UHFFFAOYSA-L cobalt(2+);disulfamate Chemical compound [Co+2].NS([O-])(=O)=O.NS([O-])(=O)=O WLQXLCXXAPYDIU-UHFFFAOYSA-L 0.000 description 1
- AMFIJXSMYBKJQV-UHFFFAOYSA-L cobalt(2+);octadecanoate Chemical compound [Co+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AMFIJXSMYBKJQV-UHFFFAOYSA-L 0.000 description 1
- CWZOMTYLSNXUEL-UHFFFAOYSA-N cobalt(ii) cyanide Chemical compound [Co+2].N#[C-].N#[C-] CWZOMTYLSNXUEL-UHFFFAOYSA-N 0.000 description 1
- JVIPVGLRUSVWPL-UHFFFAOYSA-N cobalt;cyclopentane;triphenylphosphane Chemical compound [Co].[CH]1[CH][CH][CH][CH]1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 JVIPVGLRUSVWPL-UHFFFAOYSA-N 0.000 description 1
- JUPWRUDTZGBNEX-UHFFFAOYSA-N cobalt;pentane-2,4-dione Chemical compound [Co].CC(=O)CC(C)=O.CC(=O)CC(C)=O.CC(=O)CC(C)=O JUPWRUDTZGBNEX-UHFFFAOYSA-N 0.000 description 1
- IHDMLIGEKVQUJA-UHFFFAOYSA-N cobalt;triphenylphosphane Chemical compound [Co].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 IHDMLIGEKVQUJA-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- LDUYJUKQQJQYOS-UHFFFAOYSA-N cyanoarsenic Chemical class [As]C#N LDUYJUKQQJQYOS-UHFFFAOYSA-N 0.000 description 1
- MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- YMTZLGGIBUNCMX-UHFFFAOYSA-N methyl-Co(2+) Chemical compound [Co+2]C YMTZLGGIBUNCMX-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- ZSRZHCIWJJKHAU-UHFFFAOYSA-N pentachloro-$l^{5}-arsane Chemical compound Cl[As](Cl)(Cl)(Cl)Cl ZSRZHCIWJJKHAU-UHFFFAOYSA-N 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229950003776 protoporphyrin Drugs 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003342 selenium Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- XPDICGYEJXYUDW-UHFFFAOYSA-N tetraarsenic tetrasulfide Chemical class S1[As]2S[As]3[As]1S[As]2S3 XPDICGYEJXYUDW-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000019163 vitamin B12 Nutrition 0.000 description 1
- 239000011715 vitamin B12 Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
- A62D3/10—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by subjecting to electric or wave energy or particle or ionizing radiation
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
- A62D3/10—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by subjecting to electric or wave energy or particle or ionizing radiation
- A62D3/17—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by subjecting to electric or wave energy or particle or ionizing radiation to electromagnetic radiation, e.g. emitted by a laser
- A62D3/176—Ultraviolet radiations, i.e. radiation having a wavelength of about 3nm to 400nm
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
- A62D3/30—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
- A62D3/30—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
- A62D3/33—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents by chemical fixing the harmful substance, e.g. by chelation or complexation
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/063—Titanium; Oxides or hydroxides thereof
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of rare earths
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/20—Organic substances
- A62D2101/24—Organic substances containing heavy metals
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/40—Inorganic substances
- A62D2101/43—Inorganic substances containing heavy metals, in the bonded or free state
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/40—Inorganic substances
- A62D2101/47—Inorganic substances containing oxygen, sulfur, selenium or tellurium, i.e. chalcogen
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- General Chemical & Material Sciences (AREA)
- Business, Economics & Management (AREA)
- Emergency Management (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Electromagnetism (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Catalysts (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Fire-Extinguishing Compositions (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
0.5mLの1ppmの三酸化ヒ素標準液(以下、iAs(III)と表す),7.7mLの超純水(18MΩ/cm)及び1.8mLの酢酸(特級、以下、AAと略称する)を混合した(溶液A)。触媒として、酸化チタン、水酸化セリウム、重金属吸着剤(日本板硝子社、アドセラ、以下、ADと略称する)を準備した。酸化チタンについては、TiO2(A)(ACROS社製、アナタース型)とTiO2(RA91)(キシダ化学製、ルチル型90%+アナタース型10%)を準備した。水酸化セリウムについては、水酸化第二セリウム(純正化学社製)を準備した。2mg(1.5mmol)のメチルコバラミンを1mLの超純水に溶かし、更にこれを超純水で100倍に希釈した(溶液B)。1.5mgのシアノコバラミンを1mLの超純水に溶かし、更にこれを超純水で100倍に希釈した(溶液C)。1.5mgのヒドロキソコバラミンを1mLの超純水に溶かし、更にこれを超純水で100倍に希釈した(溶液D)。これらの溶液と触媒を表1に示すように混合して反応溶液を調整し、サンプル管へ導入した。表1は、反応溶液の調整及び使用光源を示す。
次に、ヒ素の代わりに、アンチモンについても調べた。具体的には、実施例1で用いた溶液AのiAs(III)の代わりに、無機アンチモン(iSb(IV))を用いたものを溶液Eとし、表4に示す条件にて反応を行った。なお、番号18は表2の番号2−2と同じ条件であり、番号19は表3の番号17−2と同じ条件である。反応前後のHPLC−ICP−MSクロマトグラムを図1、図2に示す。
次に、ヒ素、アンチモンの代わりに、セレンについても調べた。具体的には、実施例1で用いた溶液AのiAs(III)の代わりに、無機セレン(iSe)を用いたものを溶液Fとし、表5に示す条件にて反応を行った。反応前後のHPLC−ICP−MSクロマトグラムを図3に示す。
次に、各種メチル源について調べた。実施例1で用いた溶液Aについて、メチル源として、酢酸(AA)の代わりに、蟻酸(以下、FAと略称する)、メタノール(以下、MeOHと略称する)、アセトン(以下、Actと略称する)、蟻酸と酢酸をモル比3:1で混合したもの(以下、3FA/AAと略称する)を用いた。表6は、反応原料と反応条件を示す。
無機ヒ素の代わりに、フェニルヒ素化合物である、ジフェニルアルシン酸(DPA)、フェニルアルソン酸(PA)、3−ニトロ−4−ヒドロキシフェニルヒ酸(NHPA)を反応溶液中のヒ素化合物として用いた。これらのヒ素化合物を含む反応溶液について、表8に示す条件にて反応を行った。表8は、フェニルヒ素化合物を出発原料として用いた場合の反応原料、反応条件を示す。
Claims (11)
- メチルラジカル、及び/又はカルボキシメチルラジカルを、ヒ素、アンチモン、セレンからなる群から選択される少なくとも1種の元素を含有する有害化合物と接触させることにより前記有害化合物中のヒ素、アンチモン、又はセレンをアルキル化することによって、前記有害化合物中のヒ素、アンチモン、又はセレンを無害化することを特徴とする有害化合物の無害化方法。
- 前記ラジカルを、光照射により生じさせる請求項1記載の方法。
- 前記ラジカルの供給源が、酢酸、メタノール、エタノール、無水酢酸、プロピオン酸、ブタン酸又は蟻酸からなる群から選択される少なくとも1種である請求項1又は2項に記載の方法。
- 前記酢酸、メタノール、エタノール、無水酢酸、プロピオン酸、ブタン酸又は蟻酸からなる群から選択される少なくとも1種を光照射することにより生じた前記メチルラジカル及び/又はカルボキシメチルラジカルを、前記有害化合物と反応させることにより、前記有害化合物を無害化する請求項1〜3項のいずれか1項に記載の方法。
- さらに、酸化チタン、又は水酸化セリウムを作用させることにより、無害化を行う請求項1〜4項のいずれか1項に記載の方法。
- さらに、コバルト錯体を用いて、無害化を行う請求項1〜5項のいずれか1項に記載の方法。
- 前記アルキル化が、メチル化である請求項1又は6項に記載の方法。
- 前記メチル化によって、有害化合物をモノメチル化合物、ジメチル化合物又はトリメチル化合物とする請求項7記載の方法。
- 前記モノメチル化合物が、モノメチルアルソニルアセテート、モノメチルアルソニルエタノール、モノメチルアルソニルアセテート又はモノメチルアルソン酸である請求項8記載の方法。
- 前記ジメチル化合物が、ジメチルアルソニルエタノール(DMAE)、ジメチルアルソニルアセテート(DMAA)、ジメチルアルシン酸、又はアルセノシュガーである請求項8記載の方法。
- 前記トリメチル化合物が、アルセノコリン、アルセノベタイン、トリメチルアルセノシュガー又はトリメチルアルシンオキシドである請求項8記載の方法。
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007286374A JP4934569B2 (ja) | 2007-11-02 | 2007-11-02 | 有害化合物の無害化方法 |
CN2008801189530A CN101883611A (zh) | 2007-11-02 | 2008-10-29 | 有害化合物的无害化方法 |
EP08843562.3A EP2213338B1 (en) | 2007-11-02 | 2008-10-29 | A method of detoxifying a harmful compound |
PCT/JP2008/003091 WO2009057300A1 (ja) | 2007-11-02 | 2008-10-29 | 有害化合物の無害化方法 |
RU2010122348/04A RU2478410C2 (ru) | 2007-11-02 | 2008-10-29 | Способ детоксикации вредного соединения |
US12/740,480 US8658850B2 (en) | 2007-11-02 | 2008-10-29 | Method of detoxifying a harmful compound |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007286374A JP4934569B2 (ja) | 2007-11-02 | 2007-11-02 | 有害化合物の無害化方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009112403A JP2009112403A (ja) | 2009-05-28 |
JP4934569B2 true JP4934569B2 (ja) | 2012-05-16 |
Family
ID=40590705
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007286374A Expired - Fee Related JP4934569B2 (ja) | 2007-11-02 | 2007-11-02 | 有害化合物の無害化方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US8658850B2 (ja) |
EP (1) | EP2213338B1 (ja) |
JP (1) | JP4934569B2 (ja) |
CN (1) | CN101883611A (ja) |
RU (1) | RU2478410C2 (ja) |
WO (1) | WO2009057300A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI398952B (zh) * | 2009-11-19 | 2013-06-11 | Ind Tech Res Inst | 電晶體 |
JP5908767B2 (ja) | 2012-03-21 | 2016-04-26 | 日本板硝子株式会社 | 有害化合物を含む被処理物の処理方法 |
WO2013187028A1 (ja) | 2012-06-14 | 2013-12-19 | パナソニック株式会社 | ヒ素を含む水溶液を処理する方法 |
WO2013187029A1 (ja) | 2012-06-14 | 2013-12-19 | パナソニック株式会社 | 6価クロムを含む水溶液を処理する方法 |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5174877A (en) * | 1986-07-24 | 1992-12-29 | Photo-Catalytics, Inc. | Apparatus for photocatalytic treatment of liquids |
RU2025145C1 (ru) * | 1992-02-13 | 1994-12-30 | Всесоюзный Научно-Исследовательский Институт Химических Реактивов И Особо Чистых Химических Веществ | Способ детоксикации хлорарсинсодержащих органических отравляющих веществ |
US5688378A (en) * | 1993-10-22 | 1997-11-18 | Crc For Waste Management & Pollution Control | Photoassisted oxidation of species in solution |
US7632803B2 (en) * | 1999-10-01 | 2009-12-15 | Dmi Life Sciences, Inc. | Metal-binding compounds and uses therefor |
EP1224024A2 (en) * | 1999-10-12 | 2002-07-24 | Emory University | Polyoxometalate materials, metal-containing materials, and methods of use thereof |
US6723349B1 (en) * | 1999-10-12 | 2004-04-20 | Emory University | Polyoxometalate materials, metal-containing materials, and methods of use thereof |
RU2182505C1 (ru) * | 2001-04-18 | 2002-05-20 | Федеральная ассоциация "Двойные технологии" | Непрерывный способ детоксикации отравляющих веществ и токсичных химических соединений |
US20050044991A1 (en) * | 2002-08-19 | 2005-03-03 | Xuming Guo | Photochemical transformation of metallic and non-metallic ions in an aqueous environment |
WO2006070885A1 (ja) * | 2004-12-28 | 2006-07-06 | Nippon Sheet Glass Company, Limited | 有害化合物の無害化方法 |
JP4522302B2 (ja) * | 2005-03-31 | 2010-08-11 | 株式会社クボタ | 有機ヒ素の無害化方法 |
JP2007209740A (ja) * | 2005-08-31 | 2007-08-23 | Nippon Sheet Glass Co Ltd | 有害化合物の無害化方法 |
JP2007300802A (ja) * | 2006-01-31 | 2007-11-22 | Nippon Sheet Glass Co Ltd | 抽出組成物及び当該抽出組成物を用いた有害化合物の無害化方法 |
WO2008012935A1 (fr) * | 2006-07-26 | 2008-01-31 | Nippon Sheet Glass Company, Limited | Formule pour alkylation et méthode de détoxication d'un composé toxique à l'aide de ladite formule |
WO2008012953A1 (en) * | 2006-07-26 | 2008-01-31 | Nippon Sheet Glass Company, Limited | Alkylation composition, and method for detoxification of toxic compound using the composition |
EP2048148A4 (en) * | 2006-07-26 | 2011-03-30 | Nippon Sheet Glass Co Ltd | AQUOCOBYRINIC ACID METHYL DERIVATIVE, ALKYLATION FORMULA AND METHODS OF DETOXING A HARMFUL COMPOUND USING THE SAME |
CL2007003415A1 (es) | 2006-11-28 | 2008-05-23 | Nippon Sheet Glass Co Ltd | Metodo para destoxificar un compuesto con metilo que comprende hacer reaccionar un compuesto organico halogenado con un compuesto de metilo que incluye un elemento seleccionado de as, sb y se para convertir el compuesto de metilo en sustancias mas in |
JP2009072507A (ja) * | 2007-09-25 | 2009-04-09 | Nippon Sheet Glass Co Ltd | 有害化合物の無害化方法 |
-
2007
- 2007-11-02 JP JP2007286374A patent/JP4934569B2/ja not_active Expired - Fee Related
-
2008
- 2008-10-29 RU RU2010122348/04A patent/RU2478410C2/ru not_active IP Right Cessation
- 2008-10-29 US US12/740,480 patent/US8658850B2/en not_active Expired - Fee Related
- 2008-10-29 WO PCT/JP2008/003091 patent/WO2009057300A1/ja active Application Filing
- 2008-10-29 CN CN2008801189530A patent/CN101883611A/zh active Pending
- 2008-10-29 EP EP08843562.3A patent/EP2213338B1/en not_active Not-in-force
Also Published As
Publication number | Publication date |
---|---|
CN101883611A (zh) | 2010-11-10 |
JP2009112403A (ja) | 2009-05-28 |
EP2213338B1 (en) | 2015-10-14 |
US8658850B2 (en) | 2014-02-25 |
RU2478410C2 (ru) | 2013-04-10 |
US20100305386A1 (en) | 2010-12-02 |
EP2213338A1 (en) | 2010-08-04 |
RU2010122348A (ru) | 2011-12-10 |
WO2009057300A1 (ja) | 2009-05-07 |
EP2213338A4 (en) | 2013-04-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Mirzaei et al. | Removal of pharmaceuticals from water by homo/heterogonous Fenton-type processes–a review | |
Machulek Jr et al. | Application of different advanced oxidation processes for the degradation of organic pollutants | |
Machulek Jr et al. | Fundamental mechanistic studies of the photo-Fenton reaction for the degradation of organic pollutants | |
Shukla et al. | Photocatalytic oxidation of phenolic compounds using zinc oxide and sulphate radicals under artificial solar light | |
Zhang et al. | Efficient activation of peroxydisulfate by g-C3N4/Bi2MoO6 nanocomposite for enhanced organic pollutants degradation through non-radical dominated oxidation processes | |
CN101417167A (zh) | 一种利用Fe0/TiO2光催化降解水中氯代酚的方法 | |
JP4934569B2 (ja) | 有害化合物の無害化方法 | |
Sýkora et al. | Homogeneous photo-oxidation of phenols: influence of metals | |
JP4956541B2 (ja) | アルキル化用組成物及び当該組成物を利用した有害化合物の無害化方法 | |
Daraei et al. | Study on the biodegradability improvement of 2, 4 dinitrophenol in wastewater using advanced oxidation/reduction process with UV/SO3/ZnO | |
Khader et al. | Recent Advances in Photocatalytic Advanced Oxidation Processes for Organic Compound Degradation: A Review | |
Khan et al. | Advanced oxidation/reduction processes (AO/RPs) for wastewater treatment, current challenges, and future perspectives: a review | |
JP2009072507A (ja) | 有害化合物の無害化方法 | |
Liu et al. | Insights into the organic degradation by sulfite activation with a Fe3O4/g-C3N4 photocatalyst under visible LED: Transformation of SO4•− to 1O2 | |
WO2008012948A1 (fr) | Dérivé méthylique d'acide aquocobyrinique, formule pour alkylation et méthodes de détoxication d'un composé nocif par utilisation de ladite formule | |
WO2008012950A1 (fr) | Formule pour alkylation et méthode de détoxication d'un composé toxique à l'aide de ladite formule | |
Beidaghdar et al. | Phenol removal from aqueous solution using advanced oxidation process enabled by a hybrid system: UV/H 2O 2/O 3/TiO 2 | |
JP4802036B2 (ja) | アルキル化用組成物及び当該組成物を利用した有害化合物の無害化方法 | |
Sufian | Enhancement of photochemical reaction for phenol degradation via TiO2 nanomaterials under H2O2 and FeCl3: mechanism and kinetic modeling | |
Xie et al. | Recent advances in solar-enhanced homogeneous water decontamination and disinfection: A review | |
JPH0194998A (ja) | 光化学的廃水処理方法 | |
Manea et al. | Green Water Treatment for Organic Pollutions: Photocatalytic Degradation Approach | |
JP4866483B2 (ja) | 有害化合物の無害化方法 | |
Huong et al. | Enhanced removal of pesticide micropollutant and bacteria using solar light-assisted Ag-doped TiO2: prospects for environmental and health impacts | |
da Silva | Intensifying Heterogeneous Photocatalysis for Bromates Reduction using the NETmix Photoreactor |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20100622 |
|
A871 | Explanation of circumstances concerning accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A871 Effective date: 20110721 |
|
A975 | Report on accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A971005 Effective date: 20110824 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110920 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20111117 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120124 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120220 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4934569 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150224 Year of fee payment: 3 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |