ES2268440T3 - Utilizacion de compuestos de complejos metalicos como catalizadores de oxidacion. - Google Patents
Utilizacion de compuestos de complejos metalicos como catalizadores de oxidacion. Download PDFInfo
- Publication number
- ES2268440T3 ES2268440T3 ES03769428T ES03769428T ES2268440T3 ES 2268440 T3 ES2268440 T3 ES 2268440T3 ES 03769428 T ES03769428 T ES 03769428T ES 03769428 T ES03769428 T ES 03769428T ES 2268440 T3 ES2268440 T3 ES 2268440T3
- Authority
- ES
- Spain
- Prior art keywords
- substituted
- alkyl
- unsubstituted
- alkylene
- hydrogen
- 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 - Lifetime
Links
- -1 METAL COMPLEX COMPOUNDS Chemical class 0.000 title claims abstract description 223
- 239000003054 catalyst Substances 0.000 title claims abstract description 58
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 56
- 230000003647 oxidation Effects 0.000 title claims description 45
- 239000003446 ligand Substances 0.000 claims abstract description 69
- 239000001257 hydrogen Substances 0.000 claims description 251
- 229910052739 hydrogen Inorganic materials 0.000 claims description 251
- 125000000217 alkyl group Chemical group 0.000 claims description 198
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 176
- 229910052757 nitrogen Inorganic materials 0.000 claims description 168
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 164
- 150000001875 compounds Chemical class 0.000 claims description 145
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 104
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 102
- 125000003118 aryl group Chemical group 0.000 claims description 99
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 97
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 92
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 91
- 150000002431 hydrogen Chemical class 0.000 claims description 86
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 76
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 71
- 239000012634 fragment Substances 0.000 claims description 65
- 239000000203 mixture Substances 0.000 claims description 65
- 150000001768 cations Chemical class 0.000 claims description 58
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 56
- 125000004429 atom Chemical group 0.000 claims description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
- 229910001868 water Inorganic materials 0.000 claims description 49
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 48
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 47
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 41
- 239000003599 detergent Substances 0.000 claims description 41
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 125000005842 heteroatom Chemical group 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 29
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 28
- 239000011572 manganese Substances 0.000 claims description 28
- 150000002978 peroxides Chemical class 0.000 claims description 27
- 238000005406 washing Methods 0.000 claims description 25
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 239000008187 granular material Substances 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 229910052742 iron Inorganic materials 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 21
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical group [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 18
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 18
- 238000009472 formulation Methods 0.000 claims description 17
- 229910052748 manganese Inorganic materials 0.000 claims description 16
- 125000004193 piperazinyl group Chemical group 0.000 claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 15
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 15
- 150000004696 coordination complex Chemical class 0.000 claims description 15
- 239000010936 titanium Substances 0.000 claims description 15
- 229910052719 titanium Inorganic materials 0.000 claims description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 14
- 229910017052 cobalt Inorganic materials 0.000 claims description 14
- 239000010941 cobalt Substances 0.000 claims description 14
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 14
- 229910052802 copper Inorganic materials 0.000 claims description 14
- 239000010949 copper Substances 0.000 claims description 14
- 229910052759 nickel Inorganic materials 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 239000007844 bleaching agent Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [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 11
- 239000000654 additive Substances 0.000 claims description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000000645 desinfectant Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 5
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 5
- 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 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 5
- 229940095064 tartrate Drugs 0.000 claims description 5
- 239000003945 anionic surfactant Substances 0.000 claims description 4
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 229910001882 dioxygen Inorganic materials 0.000 claims description 3
- 239000003623 enhancer Substances 0.000 claims description 3
- 239000002736 nonionic surfactant Substances 0.000 claims description 3
- 239000008393 encapsulating agent Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000001537 azepanes Chemical class 0.000 claims 2
- GASFVSRUEBGMDI-UHFFFAOYSA-N n-aminohydroxylamine Chemical compound NNO GASFVSRUEBGMDI-UHFFFAOYSA-N 0.000 claims 1
- AXIPBRXJGSXLHF-UHFFFAOYSA-N piperidine;pyrrolidine Chemical group C1CCNC1.C1CCNCC1 AXIPBRXJGSXLHF-UHFFFAOYSA-N 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 152
- 239000000243 solution Substances 0.000 description 63
- 150000003254 radicals Chemical group 0.000 description 58
- 238000000034 method Methods 0.000 description 30
- 238000004061 bleaching Methods 0.000 description 29
- 229910052751 metal Inorganic materials 0.000 description 28
- 239000002184 metal Substances 0.000 description 28
- 239000002253 acid Chemical class 0.000 description 27
- 239000000460 chlorine Substances 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- 230000008569 process Effects 0.000 description 19
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 18
- 230000009471 action Effects 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
- 239000000975 dye Substances 0.000 description 17
- 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 16
- 239000011734 sodium Substances 0.000 description 16
- 229910052708 sodium Inorganic materials 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229910052783 alkali metal Inorganic materials 0.000 description 15
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 15
- 239000002270 dispersing agent Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 239000002245 particle Substances 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000004753 textile Substances 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 10
- 150000001342 alkaline earth metals Chemical class 0.000 description 10
- 125000003277 amino group Chemical group 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 125000003725 azepanyl group Chemical group 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 239000001913 cellulose Substances 0.000 description 8
- 229920002678 cellulose Polymers 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- 125000000129 anionic group Chemical group 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 150000002085 enols Chemical class 0.000 description 7
- 229940088598 enzyme Drugs 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 239000007864 aqueous solution Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000002696 manganese Chemical class 0.000 description 6
- 229910021645 metal ion Inorganic materials 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 238000001694 spray drying Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000001993 wax Substances 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- 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 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 5
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 5
- 150000005840 aryl radicals Chemical class 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 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 description 5
- 239000005457 ice water Substances 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- OYTRWTUCMZNPBV-UHFFFAOYSA-N 2,6-bis[4-(4-methylpiperazin-1-yl)pyridin-2-yl]-1h-pyrimidin-2-ol Chemical compound C1CN(C)CCN1C1=CC=NC(C=2NC(O)(N=CC=2)C=2N=CC=C(C=2)N2CCN(C)CC2)=C1 OYTRWTUCMZNPBV-UHFFFAOYSA-N 0.000 description 4
- 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 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 102000005575 Cellulases Human genes 0.000 description 4
- 108010084185 Cellulases Proteins 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
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- 150000007942 carboxylates Chemical class 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
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- 238000004090 dissolution Methods 0.000 description 4
- 238000001914 filtration 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
- 150000002505 iron Chemical class 0.000 description 4
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- 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
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- 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
-
- 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
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Detergent Compositions (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02405929 | 2002-10-30 | ||
| EP02405929 | 2002-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2268440T3 true ES2268440T3 (es) | 2007-03-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03769428T Expired - Lifetime ES2268440T3 (es) | 2002-10-30 | 2003-10-21 | Utilizacion de compuestos de complejos metalicos como catalizadores de oxidacion. |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US7138363B2 (enExample) |
| EP (1) | EP1556467B1 (enExample) |
| JP (1) | JP4538797B2 (enExample) |
| KR (1) | KR101004084B1 (enExample) |
| CN (1) | CN1711347B (enExample) |
| AT (1) | ATE332356T1 (enExample) |
| AU (1) | AU2003278117B2 (enExample) |
| BR (1) | BR0315869A (enExample) |
| DE (1) | DE60306672T2 (enExample) |
| ES (1) | ES2268440T3 (enExample) |
| MX (1) | MXPA05004167A (enExample) |
| WO (1) | WO2004039934A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7259122B1 (en) * | 2004-08-30 | 2007-08-21 | John Lombardi | Chemically-resistant shelter coating |
| EP1703976A2 (en) * | 2004-01-12 | 2006-09-27 | Ciba Specialty Chemicals Holding Inc. | 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 |
| CN1929921A (zh) * | 2004-01-12 | 2007-03-14 | 西巴特殊化学制品控股公司 | 包含金属络合物和聚磷酸酯的组合物作为过氧化合物用催化剂的用途 |
| EP1742634B1 (en) * | 2004-04-13 | 2010-10-27 | ICAgen, Inc. | Polycyclic pyrimidines as potassium ion channel modulators |
| KR20070004963A (ko) * | 2004-04-29 | 2007-01-09 | 시바 스폐셜티 케미칼스 홀딩 인코포레이티드 | 경질 표면 상의 착색 얼룩을 표백하기 위한 퍼옥시화합물과의 반응에 대한 촉매로서 비스피리딜피리미딘 또는비스피리딜트리아진 리간드를 갖는 금속 착물의 용도 |
| DE102004024816A1 (de) * | 2004-05-17 | 2005-12-15 | Henkel Kgaa | Bleichverstärkerkombination für den Einsatz in Wasch- und Reinigungsmitteln |
| US20090044345A1 (en) * | 2006-02-06 | 2009-02-19 | Gunther Schlingloff | Use of Metal Complex Compounds as Oxidation Catalysts |
| EP1840198A1 (en) * | 2006-03-30 | 2007-10-03 | Unilever Plc | Bleaching composition |
| EP2173484A1 (en) * | 2007-07-23 | 2010-04-14 | Basf Se | Use of metal complex compounds as oxidation catalysts |
| EP2103735A1 (en) | 2008-03-18 | 2009-09-23 | Unilever PLC | Catalytic bleaching of substrates |
| 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 |
| CN107617418A (zh) * | 2016-07-16 | 2018-01-23 | 天津师范大学 | 基于3‑(5‑甲基‑1,3,4‑噁二唑)吡啶的硫氰酸根‑Co(II)配合物在吸附染料中的应用 |
| CN111479913B (zh) * | 2017-12-15 | 2021-12-21 | 罗地亚经营管理公司 | 含有镧系金属络合物的组合物 |
| JP7145802B2 (ja) * | 2019-03-27 | 2022-10-03 | 大阪ガスケミカル株式会社 | ２－アミノ－１，３，５－トリアジン化合物の製造方法 |
| CN115999640B (zh) * | 2023-02-06 | 2024-05-17 | 广西大学 | 一种蔗渣纤维素基-异质结有机复合光催化剂制备方法及其应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5362421A (en) * | 1993-06-16 | 1994-11-08 | Minnesota Mining And Manufacturing Company | Electrically conductive adhesive compositions |
| US5453450A (en) | 1993-06-16 | 1995-09-26 | Minnesota Mining And Manufacturing Company | Stabilized curable adhesives |
| PH11999002188B1 (en) | 1998-09-01 | 2007-08-06 | Unilever Nv | Method of treating a textile |
| AU4109100A (en) | 1999-04-01 | 2000-10-23 | Unilever Plc | Composition and method for bleaching a substrate |
| ATE300604T1 (de) | 1999-04-01 | 2005-08-15 | Unilever Nv | Zusammensetzung und verfahren zum bleichen eines substrats |
| DE60211884T2 (de) * | 2001-04-30 | 2006-11-23 | Ciba Speciality Chemicals Holding Inc. | Verwendung von metallkomplexverbindungen als oxidationskatalysatoren |
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2003
- 2003-10-21 US US10/531,906 patent/US7138363B2/en not_active Expired - Fee Related
- 2003-10-21 AU AU2003278117A patent/AU2003278117B2/en not_active Ceased
- 2003-10-21 KR KR1020057007419A patent/KR101004084B1/ko not_active Expired - Fee Related
- 2003-10-21 AT AT03769428T patent/ATE332356T1/de not_active IP Right Cessation
- 2003-10-21 ES ES03769428T patent/ES2268440T3/es not_active Expired - Lifetime
- 2003-10-21 US US11/520,398 patent/US7291584B2/en not_active Expired - Fee Related
- 2003-10-21 JP JP2004547539A patent/JP4538797B2/ja not_active Expired - Fee Related
- 2003-10-21 BR BR0315869-1A patent/BR0315869A/pt not_active Application Discontinuation
- 2003-10-21 CN CN2003801026668A patent/CN1711347B/zh not_active Expired - Fee Related
- 2003-10-21 EP EP03769428A patent/EP1556467B1/en not_active Expired - Lifetime
- 2003-10-21 WO PCT/EP2003/011636 patent/WO2004039934A1/en not_active Ceased
- 2003-10-21 MX MXPA05004167A patent/MXPA05004167A/es active IP Right Grant
- 2003-10-21 DE DE60306672T patent/DE60306672T2/de not_active Expired - Lifetime
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2007
- 2007-09-18 US US11/901,660 patent/US7612010B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US7612010B2 (en) | 2009-11-03 |
| US20070032656A1 (en) | 2007-02-08 |
| KR20050065636A (ko) | 2005-06-29 |
| DE60306672T2 (de) | 2007-06-28 |
| CN1711347B (zh) | 2010-05-26 |
| US7291584B2 (en) | 2007-11-06 |
| KR101004084B1 (ko) | 2010-12-27 |
| WO2004039934A1 (en) | 2004-05-13 |
| US20060052265A1 (en) | 2006-03-09 |
| JP2006504517A (ja) | 2006-02-09 |
| AU2003278117B2 (en) | 2009-07-30 |
| US7138363B2 (en) | 2006-11-21 |
| CN1711347A (zh) | 2005-12-21 |
| JP4538797B2 (ja) | 2010-09-08 |
| BR0315869A (pt) | 2005-09-27 |
| ATE332356T1 (de) | 2006-07-15 |
| MXPA05004167A (es) | 2005-06-08 |
| DE60306672D1 (de) | 2006-08-17 |
| EP1556467B1 (en) | 2006-07-05 |
| US20080081908A1 (en) | 2008-04-03 |
| AU2003278117A1 (en) | 2004-05-25 |
| EP1556467A1 (en) | 2005-07-27 |
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