AU2005205064A1 - Use of metal complex compounds comprising pyridine pyrimidine or s-triazine derived ligands as catalysts for oxidations with organic peroxy acids and/or precursors of organic peroxy acids and H2O2 - Google Patents
Use of metal complex compounds comprising pyridine pyrimidine or s-triazine derived ligands as catalysts for oxidations with organic peroxy acids and/or precursors of organic peroxy acids and H2O2 Download PDFInfo
- Publication number
- AU2005205064A1 AU2005205064A1 AU2005205064A AU2005205064A AU2005205064A1 AU 2005205064 A1 AU2005205064 A1 AU 2005205064A1 AU 2005205064 A AU2005205064 A AU 2005205064A AU 2005205064 A AU2005205064 A AU 2005205064A AU 2005205064 A1 AU2005205064 A1 AU 2005205064A1
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- AU
- Australia
- Prior art keywords
- substituted
- alkyl
- unsubstituted
- phenyl
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- -1 metal complex compounds Chemical class 0.000 title claims description 131
- 239000003446 ligand Substances 0.000 title claims description 70
- 239000002243 precursor Substances 0.000 title claims description 54
- 239000003054 catalyst Substances 0.000 title claims description 47
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title claims description 33
- 150000004967 organic peroxy acids Chemical class 0.000 title claims description 21
- 238000007254 oxidation reaction Methods 0.000 title claims description 18
- 230000003647 oxidation Effects 0.000 title claims description 15
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 title 1
- OIMWEHOYHJJPJD-UHFFFAOYSA-N pyridine;pyrimidine Chemical compound C1=CC=NC=C1.C1=CN=CN=C1 OIMWEHOYHJJPJD-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 136
- 239000000203 mixture Substances 0.000 claims description 89
- 229910052739 hydrogen Inorganic materials 0.000 claims description 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 85
- 239000001257 hydrogen Substances 0.000 claims description 84
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 83
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 60
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 60
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 58
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 56
- 239000011572 manganese Substances 0.000 claims description 54
- 239000003599 detergent Substances 0.000 claims description 51
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
- 150000004965 peroxy acids Chemical class 0.000 claims description 43
- 229910052748 manganese Inorganic materials 0.000 claims description 38
- 238000004061 bleaching Methods 0.000 claims description 37
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical group [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 125000002947 alkylene group Chemical group 0.000 claims description 30
- 238000004140 cleaning Methods 0.000 claims description 30
- 239000007787 solid Substances 0.000 claims description 29
- 125000003725 azepanyl group Chemical class 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 239000007844 bleaching agent Substances 0.000 claims description 27
- 238000009472 formulation Methods 0.000 claims description 25
- 239000008187 granular material Substances 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 230000000249 desinfective effect Effects 0.000 claims description 18
- 150000001768 cations Chemical class 0.000 claims description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- BGRWYDHXPHLNKA-UHFFFAOYSA-N Tetraacetylethylenediamine Chemical compound CC(=O)N(C(C)=O)CCN(C(C)=O)C(C)=O BGRWYDHXPHLNKA-UHFFFAOYSA-N 0.000 claims description 16
- 125000003107 substituted aryl group Chemical group 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 10
- 239000003945 anionic surfactant Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000002736 nonionic surfactant Substances 0.000 claims description 10
- 239000004753 textile Substances 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 239000012459 cleaning agent Substances 0.000 claims description 7
- 239000000645 desinfectant Substances 0.000 claims description 7
- 239000000975 dye Substances 0.000 claims description 7
- 229910052742 iron Inorganic materials 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 150000003235 pyrrolidines Chemical class 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 5
- 150000004696 coordination complex Chemical class 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 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
- 239000010949 copper Substances 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 claims description 3
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 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
- 125000005544 phthalimido group Chemical group 0.000 claims description 3
- 229940045872 sodium percarbonate Drugs 0.000 claims description 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 229960001922 sodium perborate Drugs 0.000 claims description 2
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 claims description 2
- 230000000063 preceeding effect Effects 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 description 70
- 238000003786 synthesis reaction Methods 0.000 description 52
- 230000015572 biosynthetic process Effects 0.000 description 51
- 239000000243 solution Substances 0.000 description 43
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 42
- 239000000460 chlorine Substances 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 32
- 238000000034 method Methods 0.000 description 32
- 238000005406 washing Methods 0.000 description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 22
- 150000003254 radicals Chemical class 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 125000003545 alkoxy group Chemical group 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 230000008569 process Effects 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 15
- 239000002270 dispersing agent Substances 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 13
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 12
- 108010065511 Amylases Proteins 0.000 description 12
- 102000013142 Amylases Human genes 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 235000019418 amylase Nutrition 0.000 description 12
- 239000004744 fabric Substances 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 11
- 229910052783 alkali metal Inorganic materials 0.000 description 11
- 229940088598 enzyme Drugs 0.000 description 11
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 108091005804 Peptidases Proteins 0.000 description 10
- 229940025131 amylases Drugs 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- 159000000000 sodium salts Chemical class 0.000 description 10
- ZCXLNGDZBFZUGC-UHFFFAOYSA-N 6-[4-(4-methylpiperazin-1-yl)pyridin-2-yl]-2-pyridin-2-yl-1h-pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CC=NC(C=2N=C(N=C(O)C=2)C=2N=CC=CC=2)=C1 ZCXLNGDZBFZUGC-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- 239000004367 Lipase Substances 0.000 description 9
- 108090001060 Lipase Proteins 0.000 description 9
- 102000004882 Lipase Human genes 0.000 description 9
- 102000035195 Peptidases Human genes 0.000 description 9
- 230000009471 action Effects 0.000 description 9
- 239000012190 activator Substances 0.000 description 9
- 125000000129 anionic group Chemical group 0.000 description 9
- 235000019421 lipase Nutrition 0.000 description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- 125000003282 alkyl amino group Chemical group 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 244000269722 Thea sinensis Species 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 150000002696 manganese Chemical class 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 238000001694 spray drying Methods 0.000 description 7
- ZUUZGQPEQORUEV-UHFFFAOYSA-N tetrahydrate;hydrochloride Chemical compound O.O.O.O.Cl ZUUZGQPEQORUEV-UHFFFAOYSA-N 0.000 description 7
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 229960001701 chloroform Drugs 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000001993 wax Substances 0.000 description 6
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 5
- 102000005575 Cellulases Human genes 0.000 description 5
- 108010084185 Cellulases Proteins 0.000 description 5
- 239000004365 Protease Substances 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 150000002191 fatty alcohols Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 4
- WYJIQGIMJMPVFP-UHFFFAOYSA-N 2,6-bis[4-(4-methylpiperazin-1-yl)pyridin-2-yl]-1h-pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CC=NC(C=2N=C(N=C(O)C=2)C=2N=CC=C(C=2)N2CCN(C)CC2)=C1 WYJIQGIMJMPVFP-UHFFFAOYSA-N 0.000 description 4
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
- KBWPFIVQVUQTPJ-UHFFFAOYSA-N 6-(4-chloropyridin-2-yl)-2-pyridin-2-yl-1h-pyrimidin-4-one Chemical compound N=1C(O)=CC(C=2N=CC=C(Cl)C=2)=NC=1C1=CC=CC=N1 KBWPFIVQVUQTPJ-UHFFFAOYSA-N 0.000 description 4
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
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- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- ZIZZXDMKZGRVOJ-UHFFFAOYSA-N ethyl 3-(4-chloropyridin-2-yl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC(Cl)=CC=N1 ZIZZXDMKZGRVOJ-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
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- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229920002689 polyvinyl acetate Polymers 0.000 description 4
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- 238000000746 purification Methods 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 230000008023 solidification Effects 0.000 description 4
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- XYUWADASSSSEBX-UHFFFAOYSA-N 1-(4-chloropyridin-2-yl)-5-pyridin-2-ylpentane-1,3,5-trione Chemical compound ClC1=CC=NC(C(=O)CC(=O)CC(=O)C=2N=CC=CC=2)=C1 XYUWADASSSSEBX-UHFFFAOYSA-N 0.000 description 3
- ZKPDXFCMHFRNQC-UHFFFAOYSA-N 1-pyridin-2-ylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=N1 ZKPDXFCMHFRNQC-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- D—TEXTILES; PAPER
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- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/847—Nickel
-
- 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
- B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
- B01J2540/10—Non-coordinating groups comprising only oxygen beside carbon or hydrogen
-
- 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
- B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
- B01J2540/40—Non-coordinating groups comprising nitrogen
- B01J2540/42—Quaternary ammonium groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Textile Engineering (AREA)
- Medicinal Chemistry (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
- Catalysts (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04100078.7 | 2004-01-12 | ||
| EP04100078 | 2004-01-12 | ||
| PCT/EP2005/050000 WO2005068074A2 (en) | 2004-01-12 | 2005-01-03 | Use of metal complex compounds comprising pyridine pryimidine or s-triazne derived ligands as catalysts for oxidations with organic peroxy acids and/or precursors of organic peroxy acid and h2o2 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2005205064A1 true AU2005205064A1 (en) | 2005-07-28 |
Family
ID=34778211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005205064A Abandoned AU2005205064A1 (en) | 2004-01-12 | 2005-01-03 | Use of metal complex compounds comprising pyridine pyrimidine or s-triazine derived ligands as catalysts for oxidations with organic peroxy acids and/or precursors of organic peroxy acids and H2O2 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20090189119A1 (enExample) |
| EP (1) | EP1703976A2 (enExample) |
| JP (1) | JP2007523973A (enExample) |
| KR (1) | KR20060126531A (enExample) |
| CN (1) | CN1929920A (enExample) |
| AU (1) | AU2005205064A1 (enExample) |
| BR (1) | BRPI0506799A (enExample) |
| MX (1) | MXPA06007817A (enExample) |
| WO (1) | WO2005068074A2 (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005105303A1 (en) * | 2004-04-29 | 2005-11-10 | Ciba Specialty Chemicals Holding Inc. | Use of metal complexes having bispyridylpyrimidine or bispyridyltriazine ligands as catalysts for reactions with peroxy compounds for bleaching coloured stains on hard surfaces |
| US20090044345A1 (en) * | 2006-02-06 | 2009-02-19 | Gunther Schlingloff | Use of Metal Complex Compounds as Oxidation Catalysts |
| EP1878733A1 (en) * | 2006-07-14 | 2008-01-16 | Novartis AG | Pyrimidine derivatives as ALK-5 inhibitors |
| WO2009000685A1 (en) * | 2007-06-25 | 2008-12-31 | Basf Se | Use of metal complex oxidation catalysts together with zinc compounds in laundry compositions |
| DE102007034725A1 (de) | 2007-07-23 | 2009-01-29 | Henkel Kgaa | TOC-Abbau in Abwässern durch Übergangsmetallkatalysatoren |
| WO2009013163A1 (en) * | 2007-07-23 | 2009-01-29 | Basf Se | Use of metal complex compounds as oxidation catalysts |
| DE102007042615A1 (de) | 2007-09-07 | 2009-03-12 | Bk Giulini Gmbh | Erhöhung der bioziden Wirkung von Wasserstoffperoxid in Abwässern durch Übergangsmetallkatalysatoren |
| US20090325841A1 (en) * | 2008-02-11 | 2009-12-31 | Ecolab Inc. | Use of activator complexes to enhance lower temperature cleaning in alkaline peroxide cleaning systems |
| BRPI0906349B1 (pt) * | 2008-02-11 | 2018-10-30 | Ecolab Inc | métodos de remoção de sujeira usando complexos ativadores para aprimorar a limpeza a temperaturas reduzidas em sistemas de limpeza com peróxido alcalino |
| EP2103735A1 (en) | 2008-03-18 | 2009-09-23 | Unilever PLC | Catalytic bleaching of substrates |
| CN101503242B (zh) * | 2009-03-13 | 2011-04-20 | 哈尔滨工业大学 | 利用中间态锰强化高锰酸钾除污染的水处理药剂 |
| RU2683654C2 (ru) | 2009-05-28 | 2019-04-01 | ДжиПи СЕЛЛЬЮЛОУС ГМБХ | Модифицированная целлюлоза из химического крафт-волокна и способы его изготовления и использования |
| US9511167B2 (en) | 2009-05-28 | 2016-12-06 | Gp Cellulose Gmbh | Modified cellulose from chemical kraft fiber and methods of making and using the same |
| US9512237B2 (en) | 2009-05-28 | 2016-12-06 | Gp Cellulose Gmbh | Method for inhibiting the growth of microbes with a modified cellulose fiber |
| US9512563B2 (en) | 2009-05-28 | 2016-12-06 | Gp Cellulose Gmbh | Surface treated modified cellulose from chemical kraft fiber and methods of making and using same |
| WO2011062959A1 (en) * | 2009-11-17 | 2011-05-26 | Novartis Ag | A hydrogen peroxide solution and kit for disinfecting contact lenses |
| CN102639625B (zh) * | 2009-12-02 | 2014-03-19 | 巴斯夫欧洲公司 | 金属配合物作为氧气吸收剂/清除剂成分在包装应用中的用途 |
| TWI558439B (zh) * | 2010-04-26 | 2016-11-21 | 三菱瓦斯化學股份有限公司 | 含過硫酸鹽及銀錯合物之化學物質分解用處理劑及使用該處理劑之化學物質分解方法 |
| US8877353B2 (en) * | 2010-07-21 | 2014-11-04 | Versitech Limited | Platinum (II) tetradentate ONCN complexes for organic light-emitting diode applications |
| JP6254078B2 (ja) | 2011-05-23 | 2017-12-27 | ゲーペー ツェルローゼ ゲーエムベーハー | 白色度および明度が改善された針葉樹クラフト繊維、ならびにそれを作製する方法および使用する方法 |
| BR112014005435B1 (pt) * | 2011-09-08 | 2019-11-12 | Catexel Ltd | método de preparação de um pó e pó |
| CN103194896A (zh) * | 2011-11-24 | 2013-07-10 | 东华大学 | 三联吡啶金属配合物在纺织品低温练漂助剂中的应用 |
| CN103174006A (zh) * | 2011-11-24 | 2013-06-26 | 东华大学 | 双吡啶嘧啶金属配合物在纺织品低温练漂助剂中的应用 |
| EP3800290B1 (en) | 2012-01-12 | 2023-11-01 | GP Cellulose GmbH | A low viscosity kraft fiber having reduced yellowing properties and methods of making and using the same |
| CN106968127B (zh) | 2012-04-18 | 2019-03-01 | Gp纤维素股份有限公司 | 用于粘胶溶液的针叶木牛皮纸浆 |
| KR102180512B1 (ko) | 2013-02-08 | 2020-11-19 | 게페 첼루로제 게엠베하 | 개선된 알파 셀룰로스 함량을 갖는 연재 크래프트 섬유 및 화학적 셀룰로스 제품의 생산에서의 그의 용도 |
| US10138598B2 (en) | 2013-03-14 | 2018-11-27 | Gp Cellulose Gmbh | Method of making a highly functional, low viscosity kraft fiber using an acidic bleaching sequence and a fiber made by the process |
| CA2901915A1 (en) | 2013-03-15 | 2014-09-18 | Gp Cellulose Gmbh | A low viscosity kraft fiber having an enhanced carboxyl content and methods of making and using the same |
| ES2894685T3 (es) | 2013-08-16 | 2022-02-15 | Catexel Tech Limited | Composición |
| WO2016052196A1 (ja) * | 2014-09-29 | 2016-04-07 | 富士フイルム株式会社 | 光電変換素子、色素増感太陽電池、金属錯体色素、色素溶液、およびターピリジン化合物またはそのエステル化物 |
| WO2016052193A1 (ja) * | 2014-09-29 | 2016-04-07 | 富士フイルム株式会社 | 光電変換素子、色素増感太陽電池、金属錯体色素、色素溶液、およびターピリジン化合物またはそのエステル化物 |
| CN105369581A (zh) * | 2015-11-04 | 2016-03-02 | 泉州市新宏化工贸易有限公司 | 一种棉织物练漂后除氧工艺及棉洁爽 |
| CN106478745B (zh) * | 2016-10-14 | 2019-02-05 | 高介平 | 一种无甲醛水性交联剂及其制备方法和对织物的整理工艺 |
| WO2018093697A1 (en) | 2016-11-16 | 2018-05-24 | Gp Cellulose Gmbh | Modified cellulose from chemical fiber and methods of making and using the same |
| EP3967742A1 (en) | 2020-09-15 | 2022-03-16 | WeylChem Performance Products GmbH | Compositions comprising bleaching catalyst, manufacturing process thereof, and bleaching and cleaning agent comprising same |
| CN114887663B (zh) * | 2022-05-03 | 2023-05-12 | 东华大学 | 一种产生单线态氧的催化系统及其应用 |
| CN115634716A (zh) * | 2022-10-20 | 2023-01-24 | 金宏气体股份有限公司 | 光催化剂、其制备方法、光催化体系及应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3912648A (en) * | 1973-03-21 | 1975-10-14 | American Cyanamid Co | Ring halogen-free substituted triazine compounds as bleach activators |
| US5268477A (en) * | 1985-09-12 | 1993-12-07 | The Upjohn Company | Triazinylpiperazinyl amine intermediates |
| AU6357896A (en) * | 1996-06-19 | 1998-01-07 | Hans-Peter Call | Multicomponent system for use with detergent substances |
| DE19726241A1 (de) * | 1997-06-20 | 1998-12-24 | Call Krimhild | Erweitertes enzymatisches Multikomponentensystem zur Behandlung von Abwässern, zur Herstellung von Holzverbundstoffen, zum Deinken von Altpapier, Colour stripping von Altpapier, zum Einsatz als Oxidationssystem bei der organischen Synthese und zum Einsatz bei der Kohleverflüssigung |
| JPH1150096A (ja) * | 1997-08-01 | 1999-02-23 | Lion Corp | 自動食器洗浄機用粒状洗浄剤組成物 |
| CN1361816B (zh) * | 1999-07-14 | 2010-05-26 | 西巴特殊化学品控股有限公司 | 三脚配位体的金属络合物 |
| CA2401039A1 (en) * | 2000-02-29 | 2001-09-07 | Unilever Plc | Composition and method for bleaching a substrate |
| JP3605012B2 (ja) * | 2000-08-11 | 2004-12-22 | 独立行政法人科学技術振興機構 | オレフィンの酸化的分解によるケトンの製造法 |
| DE60211884T2 (de) * | 2001-04-30 | 2006-11-23 | Ciba Speciality Chemicals Holding Inc. | Verwendung von metallkomplexverbindungen als oxidationskatalysatoren |
| EP1556467B1 (en) * | 2002-10-30 | 2006-07-05 | Ciba SC Holding AG | Use of metal complex compounds as oxidation catalysts |
| MXPA05012513A (es) * | 2003-05-21 | 2006-02-08 | Ciba Sc Holding Ag | Composicion estable en forma de particulas que comprende catalizadores de bloqueo. |
-
2005
- 2005-01-03 EP EP05701417A patent/EP1703976A2/en not_active Withdrawn
- 2005-01-03 JP JP2006548291A patent/JP2007523973A/ja not_active Withdrawn
- 2005-01-03 KR KR1020067013458A patent/KR20060126531A/ko not_active Withdrawn
- 2005-01-03 CN CNA2005800074023A patent/CN1929920A/zh active Pending
- 2005-01-03 AU AU2005205064A patent/AU2005205064A1/en not_active Abandoned
- 2005-01-03 BR BRPI0506799-5A patent/BRPI0506799A/pt not_active IP Right Cessation
- 2005-01-03 US US10/585,543 patent/US20090189119A1/en not_active Abandoned
- 2005-01-03 MX MXPA06007817A patent/MXPA06007817A/es unknown
- 2005-01-03 WO PCT/EP2005/050000 patent/WO2005068074A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA06007817A (es) | 2006-09-01 |
| WO2005068074A3 (en) | 2006-05-18 |
| CN1929920A (zh) | 2007-03-14 |
| BRPI0506799A (pt) | 2007-05-22 |
| EP1703976A2 (en) | 2006-09-27 |
| KR20060126531A (ko) | 2006-12-07 |
| US20090189119A1 (en) | 2009-07-30 |
| JP2007523973A (ja) | 2007-08-23 |
| WO2005068074A2 (en) | 2005-07-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |