TWI311924B - Use of metal complex compound as oxidation catalysts - Google Patents
Use of metal complex compound as oxidation catalysts Download PDFInfo
- Publication number
- TWI311924B TWI311924B TW092118692A TW92118692A TWI311924B TW I311924 B TWI311924 B TW I311924B TW 092118692 A TW092118692 A TW 092118692A TW 92118692 A TW92118692 A TW 92118692A TW I311924 B TWI311924 B TW I311924B
- Authority
- TW
- Taiwan
- Prior art keywords
- substituted
- group
- unsubstituted
- alkyl
- hydrogen
- Prior art date
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- -1 metal complex compound Chemical class 0.000 title claims description 62
- 238000007254 oxidation reaction Methods 0.000 title claims description 13
- 230000003647 oxidation Effects 0.000 title claims description 12
- 239000003054 catalyst Substances 0.000 title description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 160
- 239000001257 hydrogen Substances 0.000 claims description 90
- 229910052739 hydrogen Inorganic materials 0.000 claims description 90
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 69
- 229910052757 nitrogen Inorganic materials 0.000 claims description 68
- 239000000203 mixture Substances 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 229910001868 water Inorganic materials 0.000 claims description 39
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- 150000004696 coordination complex Chemical class 0.000 claims description 37
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 36
- 239000003446 ligand Substances 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 125000002947 alkylene group Chemical group 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 26
- 238000004061 bleaching Methods 0.000 claims description 25
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 24
- 239000006210 lotion Substances 0.000 claims description 21
- 150000001768 cations Chemical class 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 19
- 239000000975 dye Substances 0.000 claims description 19
- 239000011572 manganese Substances 0.000 claims description 19
- 150000002978 peroxides Chemical class 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 18
- 239000002184 metal Substances 0.000 claims description 18
- 238000005406 washing Methods 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
- 239000004744 fabric Substances 0.000 claims description 14
- 239000007844 bleaching agent Substances 0.000 claims description 13
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229910052748 manganese Inorganic materials 0.000 claims description 12
- 238000004140 cleaning Methods 0.000 claims description 11
- 229910052742 iron Inorganic materials 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 10
- 150000002500 ions Chemical class 0.000 claims description 10
- 229910052707 ruthenium Inorganic materials 0.000 claims description 10
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 210000003802 sputum Anatomy 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 206010036790 Productive cough Diseases 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 238000013508 migration Methods 0.000 claims description 8
- 230000005012 migration Effects 0.000 claims description 8
- 208000024794 sputum Diseases 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000012459 cleaning agent Substances 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 230000000249 desinfective effect Effects 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 5
- 239000003945 anionic surfactant Substances 0.000 claims description 5
- 229910052797 bismuth Inorganic materials 0.000 claims description 5
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 239000000645 desinfectant Substances 0.000 claims description 5
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 5
- 239000002736 nonionic surfactant Substances 0.000 claims description 5
- 150000002923 oximes Chemical class 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 150000004698 iron complex Chemical class 0.000 claims description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical group [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000004299 exfoliation Methods 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims description 2
- 229910052746 lanthanum Inorganic materials 0.000 claims description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims 2
- UOGVDNHBAACXBO-UHFFFAOYSA-N C(#N)[Ru][N+](=O)[O-] Chemical group C(#N)[Ru][N+](=O)[O-] UOGVDNHBAACXBO-UHFFFAOYSA-N 0.000 claims 1
- 229910052684 Cerium Inorganic materials 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 102000016736 Cyclin Human genes 0.000 claims 1
- 108050006400 Cyclin Proteins 0.000 claims 1
- 241001529936 Murinae Species 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- 101100497572 Pisum sativum CVCA gene Proteins 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- CFQGDIWRTHFZMQ-UHFFFAOYSA-N argon helium Chemical compound [He].[Ar] CFQGDIWRTHFZMQ-UHFFFAOYSA-N 0.000 claims 1
- 230000037429 base substitution Effects 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- QUQFTIVBFKLPCL-UHFFFAOYSA-L copper;2-amino-3-[(2-amino-2-carboxylatoethyl)disulfanyl]propanoate Chemical compound [Cu+2].[O-]C(=O)C(N)CSSCC(N)C([O-])=O QUQFTIVBFKLPCL-UHFFFAOYSA-L 0.000 claims 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical group COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 238000004659 sterilization and disinfection Methods 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 230000000007 visual effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 40
- 239000002585 base Substances 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 26
- 239000003599 detergent Substances 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 150000003839 salts Chemical class 0.000 description 19
- 239000008187 granular material Substances 0.000 description 16
- 239000002245 particle Substances 0.000 description 16
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- 239000002270 dispersing agent Substances 0.000 description 14
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
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- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 11
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- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- OFSDTGZOZPQDCK-UHFFFAOYSA-N polane Chemical compound [PoH2] OFSDTGZOZPQDCK-UHFFFAOYSA-N 0.000 description 1
- 229910000035 polane Inorganic materials 0.000 description 1
- 229920002006 poly(N-vinylimidazole) polymer Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229940070721 polyacrylate Drugs 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical group CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000001055 reflectance spectroscopy Methods 0.000 description 1
- FTIMWVSQXCWTAW-UHFFFAOYSA-N ruthenium Chemical compound [Ru].[Ru] FTIMWVSQXCWTAW-UHFFFAOYSA-N 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 229940071089 sarcosinate Drugs 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 239000013042 solid detergent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- BGKZULDOBMANRY-UHFFFAOYSA-N sulfanyl prop-2-enoate Chemical compound SOC(=O)C=C BGKZULDOBMANRY-UHFFFAOYSA-N 0.000 description 1
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- IOJRZKFVJHTXJS-UHFFFAOYSA-N triazetidine Chemical compound C1NNN1 IOJRZKFVJHTXJS-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- ZULTYUIALNTCSA-UHFFFAOYSA-N zinc hydride Chemical compound [ZnH2] ZULTYUIALNTCSA-UHFFFAOYSA-N 0.000 description 1
- 229910000051 zinc hydride Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3902—Organic or inorganic per-compounds combined with specific additives
- C11D3/3905—Bleach activators or bleach catalysts
- C11D3/3932—Inorganic compounds or complexes
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/168—Organometallic compounds or orgometallic complexes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/395—Bleaching agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Inorganic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Detergent Compositions (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02405591 | 2002-07-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200404605A TW200404605A (en) | 2004-04-01 |
| TWI311924B true TWI311924B (en) | 2009-07-11 |
Family
ID=30011302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092118692A TWI311924B (en) | 2002-07-11 | 2003-07-09 | Use of metal complex compound as oxidation catalysts |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7494964B2 (enExample) |
| EP (1) | EP1521820B1 (enExample) |
| JP (1) | JP4643259B2 (enExample) |
| KR (1) | KR101018716B1 (enExample) |
| CN (1) | CN1306017C (enExample) |
| AR (1) | AR040480A1 (enExample) |
| AT (1) | ATE321117T1 (enExample) |
| AU (1) | AU2003253026B2 (enExample) |
| BR (1) | BR0312694B1 (enExample) |
| DE (1) | DE60304200T2 (enExample) |
| ES (1) | ES2259771T3 (enExample) |
| MX (1) | MXPA05000483A (enExample) |
| TW (1) | TWI311924B (enExample) |
| WO (1) | WO2004007657A1 (enExample) |
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| JP4414653B2 (ja) * | 2001-04-30 | 2010-02-10 | チバ ホールディング インコーポレーテッド | 酸化触媒としての金属錯体化合物及びその使用 |
| KR20050059312A (ko) * | 2002-10-29 | 2005-06-17 | 시바 스폐셜티 케미칼스 홀딩 인코포레이티드 | 분자 산소 또는 공기를 사용한 산화반응에 대한 촉매로서금속 착물 화합물의 용도 |
| GB2394720A (en) * | 2002-10-30 | 2004-05-05 | Reckitt Benckiser Nv | Metal complex compounds in dishwasher formulations |
| GB2409207B (en) * | 2003-12-20 | 2006-08-09 | Reckitt Benckiser Nv | Use of metal complex compounds as oxidation catalysts |
| EP1703977A1 (en) * | 2004-01-12 | 2006-09-27 | Ciba SC Holding AG | Use of a composition comprising metal complex compounds and polyphosphonates as catalysts for oxidations |
| JP2007534479A (ja) * | 2004-04-29 | 2007-11-29 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 硬質表面上の着色した汚れを漂白するためのパーオキシ化合物を用いた反応の触媒としての、ビスピリジルピリミジン又はビスピリジルトリアジン配位子を有する金属錯体の使用 |
| EP1747259A1 (de) * | 2004-05-17 | 2007-01-31 | Henkel Kommanditgesellschaft auf Aktien | Waschmittel mit gegebenenfalls in situ erzeugtem bleichverstärkendem übergangsmetallkomplex |
| DE102004024816A1 (de) * | 2004-05-17 | 2005-12-15 | Henkel Kgaa | Bleichverstärkerkombination für den Einsatz in Wasch- und Reinigungsmitteln |
| EP1879548A2 (en) * | 2005-05-13 | 2008-01-23 | Ciba Specialty Chemicals Holding Inc. | Process for coloring keratin fibers comprising metal complexes |
| WO2009109533A1 (en) * | 2008-03-07 | 2009-09-11 | Basf Se | Bleach catalysts and their use as teeth whitening agents |
| EP2103735A1 (en) | 2008-03-18 | 2009-09-23 | Unilever PLC | Catalytic bleaching of substrates |
| WO2009124855A1 (en) * | 2008-04-09 | 2009-10-15 | Basf Se | Use of metal hydrazide complex compounds as oxidation catalysts |
| WO2010020583A1 (en) * | 2008-08-20 | 2010-02-25 | Basf Se | Improved bleach process |
| DE102008045207A1 (de) * | 2008-08-30 | 2010-03-04 | Clariant International Limited | Bleichkatalysatormischungen bestehend aus Mangansalzen und Oxalsäure oder deren Salze |
| US8415443B2 (en) * | 2009-07-10 | 2013-04-09 | Momentive Performance Materials Inc. | Hydrosilylation catalysts |
| WO2011032666A1 (de) * | 2009-09-18 | 2011-03-24 | Clariant International Ltd | Verfahren zur herstellung von verbrückten mangan-komplexen des triazacyclononans |
| TWI551551B (zh) * | 2010-04-30 | 2016-10-01 | 三菱瓦斯化學股份有限公司 | 過氧化物活性化劑以及土壤及／或地下水之淨化方法 |
| US9657435B2 (en) | 2010-06-28 | 2017-05-23 | Basf Se | Metal free bleaching composition |
| EP2651907B1 (en) | 2010-12-13 | 2014-10-01 | Basf Se | Bleach catalysts |
| US20140298591A1 (en) | 2011-10-25 | 2014-10-09 | Basf Se | Use of comb or block copolymers as soil antiredeposition agents and soil release agents in laundry processes |
| EP2771446A1 (en) | 2011-10-25 | 2014-09-03 | Basf Se | Use of acrylate copolymers as soil antiredeposition agents and soil release agents in laundry processes |
| WO2014154508A1 (en) | 2013-03-27 | 2014-10-02 | Basf Se | Block copolymers as soil release agents in laundry processes |
| US10155783B2 (en) | 2013-05-28 | 2018-12-18 | Merck Patent Gmbh | Manganese complexes and use thereof for preparing thin films |
| PL3074438T3 (pl) | 2013-11-27 | 2018-02-28 | Basf Se | Bezładne kopolimery jako środki uwalniające brud w procesach prania |
| WO2017076771A1 (en) | 2015-11-03 | 2017-05-11 | Basf Se | Bleach catalysts |
| EP3176157A1 (en) | 2015-12-01 | 2017-06-07 | Basf Se | Bleach catalysts |
| WO2017182295A1 (en) | 2016-04-18 | 2017-10-26 | Basf Se | Liquid cleaning compositions |
| WO2017186480A1 (en) | 2016-04-26 | 2017-11-02 | Basf Se | Metal free bleaching composition |
| EP3372663A1 (en) | 2017-03-10 | 2018-09-12 | Basf Se | Bleach catalysts |
| CN111875624B (zh) * | 2020-06-06 | 2022-06-14 | 桂林理工大学 | 一种基于bteb的四核锌配合物的制备、结构和荧光应用 |
| JP2026506171A (ja) | 2023-02-21 | 2026-02-20 | ビーエーエスエフ ソシエタス・ヨーロピア | 変性アルコキシル化ポリアルキレンイミン又は変性アルコキシル化ポリアミン |
| WO2024175409A1 (en) | 2023-02-21 | 2024-08-29 | Basf Se | Modified hyperbranched alkoxylated polyalkylene imines |
| WO2024175407A1 (en) | 2023-02-21 | 2024-08-29 | Basf Se | Modified alkoxylated polyalkylene imines or modified alkoxylated polyamines |
| US20260218087A1 (en) | 2023-03-13 | 2026-07-30 | Basf Se | Alkoxylated nitrogen containing polymers and their use |
| WO2024231110A1 (en) | 2023-05-05 | 2024-11-14 | Basf Se | Biodegradable polyol propoxylates, their preparation, uses, and compositions comprising them |
| MX2025014975A (es) | 2023-06-13 | 2026-02-03 | Basf Se | Composiciones de limpieza estabilizadas que comprenden edds y enzimas y su uso |
| CN122374365A (zh) | 2023-12-15 | 2026-07-10 | 巴斯夫欧洲公司 | 可生物降解的丙氧基化乙二胺、其制备、用途以及包含它们的组合物 |
| WO2025131888A1 (en) | 2023-12-19 | 2025-06-26 | Basf Se | Modified alkoxylated polyalkylene imines or modified alkoxylated polyamines |
| WO2025180874A1 (en) | 2024-02-27 | 2025-09-04 | Basf Se | Substituted 1,3-dioxolane sulfates and their use |
| WO2025195856A1 (en) | 2024-03-19 | 2025-09-25 | Basf Se | Compositions of guerbet alkyl sulfates and their use |
| WO2025202032A1 (en) | 2024-03-26 | 2025-10-02 | Basf Se | Biodegradable alkoxylated polyols, their preparation, uses, and compositions comprising them |
Family Cites Families (6)
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| JPH082878B2 (ja) | 1988-02-12 | 1996-01-17 | 富士写真フイルム株式会社 | ４’−アルコキシ−２，２’：６’，２〃−デルピリジン誘導体及びその金属錯体 |
| FR2677766B1 (fr) | 1991-06-14 | 1994-11-10 | Asulab Sa | Capteur de mesure de la quantite d'un composant en solution. |
| JP3852044B2 (ja) * | 1999-05-10 | 2006-11-29 | 独立行政法人科学技術振興機構 | 三脚型（トリポーダル）ピリジルアミン配位子を用いたアルキルパーオキソ単核鉄（ｉｉｉ）錯体のエポキシ化触媒 |
| GB9930248D0 (en) * | 1999-12-22 | 2000-02-09 | Johnson Matthey Plc | Surface cleaner |
| EP1217056A1 (en) * | 2000-12-21 | 2002-06-26 | Johnson Matthey Public Limited Company | Photocatalytic material |
| JP4414653B2 (ja) | 2001-04-30 | 2010-02-10 | チバ ホールディング インコーポレーテッド | 酸化触媒としての金属錯体化合物及びその使用 |
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- 2003-07-03 AT AT03763699T patent/ATE321117T1/de not_active IP Right Cessation
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- 2003-07-03 BR BRPI0312694-3B1A patent/BR0312694B1/pt not_active IP Right Cessation
- 2003-07-03 JP JP2004520474A patent/JP4643259B2/ja not_active Expired - Fee Related
- 2003-07-03 KR KR1020057000337A patent/KR101018716B1/ko not_active Expired - Fee Related
- 2003-07-03 CN CNB038164892A patent/CN1306017C/zh not_active Expired - Fee Related
- 2003-07-03 US US10/520,841 patent/US7494964B2/en not_active Expired - Fee Related
- 2003-07-09 TW TW092118692A patent/TWI311924B/zh not_active IP Right Cessation
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Also Published As
| Publication number | Publication date |
|---|---|
| TW200404605A (en) | 2004-04-01 |
| WO2004007657A1 (en) | 2004-01-22 |
| AU2003253026A1 (en) | 2004-02-02 |
| BR0312694B1 (pt) | 2013-11-05 |
| US20060100123A1 (en) | 2006-05-11 |
| EP1521820A1 (en) | 2005-04-13 |
| JP2005532158A (ja) | 2005-10-27 |
| BR0312694A (pt) | 2005-04-26 |
| EP1521820B1 (en) | 2006-03-22 |
| MXPA05000483A (es) | 2005-03-23 |
| CN1306017C (zh) | 2007-03-21 |
| DE60304200D1 (de) | 2006-05-11 |
| KR101018716B1 (ko) | 2011-03-04 |
| ES2259771T3 (es) | 2006-10-16 |
| DE60304200T2 (de) | 2006-08-17 |
| JP4643259B2 (ja) | 2011-03-02 |
| CN1668730A (zh) | 2005-09-14 |
| KR20050017091A (ko) | 2005-02-21 |
| AU2003253026B2 (en) | 2009-05-14 |
| ATE321117T1 (de) | 2006-04-15 |
| AR040480A1 (es) | 2005-04-06 |
| US7494964B2 (en) | 2009-02-24 |
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