DE2706516C3 - Metallphthalocyanin-Kataiysator und dessen Verwendung - Google Patents
Metallphthalocyanin-Kataiysator und dessen VerwendungInfo
- Publication number
- DE2706516C3 DE2706516C3 DE2706516A DE2706516A DE2706516C3 DE 2706516 C3 DE2706516 C3 DE 2706516C3 DE 2706516 A DE2706516 A DE 2706516A DE 2706516 A DE2706516 A DE 2706516A DE 2706516 C3 DE2706516 C3 DE 2706516C3
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- sulfophthalate
- ammonium
- hours
- oxygen
- 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
Links
- 239000003054 catalyst Substances 0.000 title claims description 25
- 229910052751 metal Inorganic materials 0.000 title claims description 10
- 239000002184 metal Substances 0.000 title claims description 10
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 title claims description 7
- 239000000203 mixture Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 claims description 6
- 239000011609 ammonium molybdate Substances 0.000 claims description 6
- 235000018660 ammonium molybdate Nutrition 0.000 claims description 6
- 229940010552 ammonium molybdate Drugs 0.000 claims description 6
- MEYVLGVRTYSQHI-UHFFFAOYSA-L cobalt(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Co+2].[O-]S([O-])(=O)=O MEYVLGVRTYSQHI-UHFFFAOYSA-L 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- WNKQDGLSQUASME-UHFFFAOYSA-N 4-sulfophthalic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1C(O)=O WNKQDGLSQUASME-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 claims description 3
- 229940099596 manganese sulfate Drugs 0.000 claims description 2
- 239000011702 manganese sulphate Substances 0.000 claims description 2
- 235000007079 manganese sulphate Nutrition 0.000 claims description 2
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 claims description 2
- VXNYVYJABGOSBX-UHFFFAOYSA-N rhodium(3+);trinitrate Chemical compound [Rh+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VXNYVYJABGOSBX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- UUUGYDOQQLOJQA-UHFFFAOYSA-L vanadyl sulfate Chemical compound [V+2]=O.[O-]S([O-])(=O)=O UUUGYDOQQLOJQA-UHFFFAOYSA-L 0.000 claims description 2
- 229910000352 vanadyl sulfate Inorganic materials 0.000 claims description 2
- 229940041260 vanadyl sulfate Drugs 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000000034 method Methods 0.000 description 11
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- RMPQIFXEQFYSEM-UHFFFAOYSA-N triazanium;4-sulfonatophthalate Chemical compound [NH4+].[NH4+].[NH4+].[O-]C(=O)C1=CC=C(S([O-])(=O)=O)C=C1C([O-])=O RMPQIFXEQFYSEM-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 4
- 230000010718 Oxidation Activity Effects 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- SNCYXANPVGRYNL-UHFFFAOYSA-L disodium;4-sulfophthalate Chemical compound [Na+].[Na+].OS(=O)(=O)C1=CC=C(C([O-])=O)C(C([O-])=O)=C1 SNCYXANPVGRYNL-UHFFFAOYSA-L 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WZUKKIPWIPZMAS-UHFFFAOYSA-K Ammonium alum Chemical compound [NH4+].O.O.O.O.O.O.O.O.O.O.O.O.[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O WZUKKIPWIPZMAS-UHFFFAOYSA-K 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- -1 aromatic mercaptans Chemical class 0.000 description 2
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- UTRBCDVXZXYLMH-UHFFFAOYSA-L dipotassium;4-sulfophthalate Chemical compound [K+].[K+].OS(=O)(=O)C1=CC=C(C([O-])=O)C(C([O-])=O)=C1 UTRBCDVXZXYLMH-UHFFFAOYSA-L 0.000 description 2
- 150000002019 disulfides Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- FRQQKWGDKVGLFI-UHFFFAOYSA-N 2-methylundecane-2-thiol Chemical compound CCCCCCCCCC(C)(C)S FRQQKWGDKVGLFI-UHFFFAOYSA-N 0.000 description 1
- PMJNEQWWZRSFCE-UHFFFAOYSA-N 3-ethoxy-3-oxo-2-(thiophen-2-ylmethyl)propanoic acid Chemical compound CCOC(=O)C(C(O)=O)CC1=CC=CS1 PMJNEQWWZRSFCE-UHFFFAOYSA-N 0.000 description 1
- SDGNNLQZAPXALR-UHFFFAOYSA-N 3-sulfophthalic acid Chemical compound OC(=O)C1=CC=CC(S(O)(=O)=O)=C1C(O)=O SDGNNLQZAPXALR-UHFFFAOYSA-N 0.000 description 1
- BBALEEADKHTORD-UHFFFAOYSA-J 4-sulfophthalate;titanium(4+) Chemical compound [Ti+4].OS(=O)(=O)C1=CC=C(C([O-])=O)C(C([O-])=O)=C1.OS(=O)(=O)C1=CC=C(C([O-])=O)C(C([O-])=O)=C1 BBALEEADKHTORD-UHFFFAOYSA-J 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 235000002918 Fraxinus excelsior Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- HVCXHPPDIVVWOJ-UHFFFAOYSA-N [K].[Mn] Chemical compound [K].[Mn] HVCXHPPDIVVWOJ-UHFFFAOYSA-N 0.000 description 1
- VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 235000011126 aluminium potassium sulphate Nutrition 0.000 description 1
- VHUJINUACVEASK-UHFFFAOYSA-J aluminum;cesium;disulfate;dodecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.[Al+3].[Cs+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VHUJINUACVEASK-UHFFFAOYSA-J 0.000 description 1
- XEFPYRQNEADKNO-UHFFFAOYSA-J aluminum;rubidium(1+);disulfate;dodecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.[Al+3].[Rb+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O XEFPYRQNEADKNO-UHFFFAOYSA-J 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940090948 ammonium benzoate Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000002956 ash Substances 0.000 description 1
- LCPUDZUWZDSKMX-UHFFFAOYSA-K azane;hydrogen sulfate;iron(3+);sulfate;dodecahydrate Chemical compound [NH4+].O.O.O.O.O.O.O.O.O.O.O.O.[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O LCPUDZUWZDSKMX-UHFFFAOYSA-K 0.000 description 1
- UQTCSFPVHNDUOG-UHFFFAOYSA-N azanium 4-carboxy-2,6-dihydroxyphenolate Chemical compound [NH4+].OC(=O)C1=CC(O)=C([O-])C(O)=C1 UQTCSFPVHNDUOG-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- OIDPCXKPHYRNKH-UHFFFAOYSA-J chrome alum Chemical compound [K]OS(=O)(=O)O[Cr]1OS(=O)(=O)O1 OIDPCXKPHYRNKH-UHFFFAOYSA-J 0.000 description 1
- 229940044175 cobalt sulfate Drugs 0.000 description 1
- 229910000361 cobalt sulfate Inorganic materials 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- ONCXRAKDQDBHNX-UHFFFAOYSA-L dilithium;4-sulfophthalate Chemical compound [Li+].[Li+].OS(=O)(=O)C1=CC=C(C([O-])=O)C(C([O-])=O)=C1 ONCXRAKDQDBHNX-UHFFFAOYSA-L 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- XGZFAPHEWZNVQO-UHFFFAOYSA-L magnesium;4-sulfophthalate Chemical compound [Mg+2].OS(=O)(=O)C1=CC=C(C([O-])=O)C(C([O-])=O)=C1 XGZFAPHEWZNVQO-UHFFFAOYSA-L 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- VEUPBXGDDKXJFT-UHFFFAOYSA-L manganese(2+);4-sulfophthalate Chemical compound [Mn+2].OS(=O)(=O)C1=CC=C(C([O-])=O)C(C([O-])=O)=C1 VEUPBXGDDKXJFT-UHFFFAOYSA-L 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229940050271 potassium alum Drugs 0.000 description 1
- GNHOJBNSNUXZQA-UHFFFAOYSA-J potassium aluminium sulfate dodecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.[Al+3].[K+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GNHOJBNSNUXZQA-UHFFFAOYSA-J 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- HUZPOSDEFPSMBE-UHFFFAOYSA-H scandium(3+) 4-sulfophthalate Chemical compound S(=O)(=O)(O)C=1C=C(C(C(=O)[O-])=CC1)C(=O)[O-].[Sc+3].S(=O)(=O)(O)C=1C=C(C(C(=O)[O-])=CC1)C(=O)[O-].S(=O)(=O)(O)C=1C=C(C(C(=O)[O-])=CC1)C(=O)[O-].[Sc+3] HUZPOSDEFPSMBE-UHFFFAOYSA-H 0.000 description 1
- 235000011127 sodium aluminium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- WYXIGTJNYDDFFH-UHFFFAOYSA-Q triazanium;borate Chemical compound [NH4+].[NH4+].[NH4+].[O-]B([O-])[O-] WYXIGTJNYDDFFH-UHFFFAOYSA-Q 0.000 description 1
- IWFDIIDATFUMQH-UHFFFAOYSA-K trisodium;4-sulfonatophthalate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=CC=C(S([O-])(=O)=O)C=C1C([O-])=O IWFDIIDATFUMQH-UHFFFAOYSA-K 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/065—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide having -COOH or -SO3H radicals or derivatives thereof, directly linked to the skeleton
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
- B01J31/183—Ligands comprising condensed ring systems, e.g. acridine, carbazole with more than one complexing nitrogen atom, e.g. phenanthroline
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/045—Special non-pigmentary uses, e.g. catalyst, photosensitisers of phthalocyanine dyes or pigments
-
- 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
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
- B01J2531/025—Ligands with a porphyrin ring system or analogues thereof, e.g. phthalocyanines, corroles
-
- 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
- B01J2531/50—Complexes comprising metals of Group V (VA or VB) as the central metal
- B01J2531/56—Vanadium
-
- 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
- B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
- B01J2531/72—Manganese
-
- 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
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
-
- 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
- B01J2531/845—Cobalt
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/659,394 US4048097A (en) | 1976-02-19 | 1976-02-19 | Sulfonated metal phthalocyanine catalyst |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2706516A1 DE2706516A1 (de) | 1977-08-25 |
| DE2706516B2 DE2706516B2 (de) | 1978-10-05 |
| DE2706516C3 true DE2706516C3 (de) | 1979-09-27 |
Family
ID=24645225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2706516A Expired DE2706516C3 (de) | 1976-02-19 | 1977-02-16 | Metallphthalocyanin-Kataiysator und dessen Verwendung |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US4048097A (enExample) |
| JP (1) | JPS5922575B2 (enExample) |
| AU (1) | AU504780B2 (enExample) |
| BE (1) | BE851605A (enExample) |
| BR (1) | BR7701049A (enExample) |
| CA (1) | CA1103240A (enExample) |
| DE (1) | DE2706516C3 (enExample) |
| ES (1) | ES456012A1 (enExample) |
| FR (1) | FR2341363A1 (enExample) |
| GB (1) | GB1569356A (enExample) |
| IN (1) | IN155270B (enExample) |
| IT (1) | IT1115501B (enExample) |
| MX (1) | MX143797A (enExample) |
| PT (1) | PT66161B (enExample) |
| SE (1) | SE436697B (enExample) |
| SU (1) | SU673152A3 (enExample) |
| YU (1) | YU39380B (enExample) |
| ZA (1) | ZA77693B (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4088569A (en) * | 1976-02-24 | 1978-05-09 | Uop Inc. | Mercaptan oxidation in a liquid hydrocarbon with a metal phthalocyanine catalyst |
| FR2431481A1 (fr) * | 1978-07-19 | 1980-02-15 | Uop Inc | Procede de carbonylation d'alcools, catalyse par une phtalocyanine metallique et des activateurs |
| JPS58189964A (ja) * | 1982-04-06 | 1983-11-05 | Toshiba Battery Co Ltd | 電池 |
| CH657864A5 (de) * | 1984-02-17 | 1986-09-30 | Ciba Geigy Ag | Wasserloesliche phthalocyaninverbindungen und deren verwendung als photoaktivatoren. |
| DE3687838T2 (de) * | 1985-12-24 | 1993-08-12 | Daiwa Spinning Co Ltd | Deodorant-bettmaterial. |
| US4753722A (en) * | 1986-06-17 | 1988-06-28 | Merichem Company | Treatment of mercaptan-containing streams utilizing nitrogen based promoters |
| US4721813A (en) * | 1986-08-25 | 1988-01-26 | Phillips Petroleum Company | Method for the oxidation of mercaptoalkanols to dithiodiglycols |
| DE3703837A1 (de) * | 1987-02-07 | 1988-08-18 | Basf Ag | Verfahren zum katalytischen abbau von oxidierbaren organischen und anorganischen verbindungen in waessern |
| DE3816952A1 (de) * | 1988-05-18 | 1989-11-23 | Inst Kinetika I Kataliz | Katalysator zur oxydation von mercaptanen zu disulfiden und verfahren zu seiner herstellung |
| US5683574A (en) * | 1994-08-08 | 1997-11-04 | Chevron U.S.A. Inc. | Method for the extraction of low molecular weight mercaptans from petroleum and gas condensates |
| US5698103A (en) * | 1996-10-04 | 1997-12-16 | Uop | Extraction of water-soluble metal chelates used as catalysts in sweetening sour hydrocarbon feedstocks |
| RU2152823C1 (ru) * | 1998-11-24 | 2000-07-20 | Ивановский государственный химико-технологический университет | Способ приготовления катализатора для жидкофазного окисления сернистых соединений |
| RU2233265C1 (ru) * | 2003-01-14 | 2004-07-27 | Ивановский государственный химико-технологический университет | Дикалиевая соль 3-бром-4-карбокси-5-сульфофталевой кислоты как промежуточный продукт для синтеза замещенного фталоцианина кобальта |
| RU2233281C1 (ru) * | 2003-01-14 | 2004-07-27 | Ивановский государственный химико-технологический университет | Тетра (3-бром-4-карбокси-5-сульфо)фталоцианин кобальта |
| DE10323839B3 (de) * | 2003-05-23 | 2004-10-21 | Thioplast Chemicals Gmbh & Co.Kg | Oxidation von Mercaptoethanol |
| US7223332B1 (en) | 2003-10-21 | 2007-05-29 | Uop Llc | Reactor and process for mercaptan oxidation and separation in the same vessel |
| WO2008079356A2 (en) * | 2006-12-22 | 2008-07-03 | Dow Global Technologies Inc. | Tetra-sulfo iron-phthalocyanine and related methods |
| CN103031141B (zh) * | 2011-09-29 | 2015-11-25 | 中国石油化工股份有限公司 | 一种脱除轻质石油产品中硫醇的方法 |
| PL3080079T3 (pl) * | 2013-12-11 | 2018-12-31 | Basf Se | Utlenianie 2-merkaptoetanolu |
| CN118405772A (zh) * | 2024-04-12 | 2024-07-30 | 重庆理工大学 | 一种磺化酞菁材料在铬离子污染中的应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE535707A (enExample) * | 1954-02-17 | |||
| US2950286A (en) * | 1958-06-30 | 1960-08-23 | Du Pont | Basic dye salts of polysulfonated phthalocyanines and process of producing the same |
| US2988500A (en) * | 1959-03-13 | 1961-06-13 | Universal Oil Prod Co | Treatment of hydrocarbon distillates |
| US3230180A (en) * | 1963-02-07 | 1966-01-18 | Universal Oil Prod Co | Metal phthalocyanine catalyst preparation |
| US3565959A (en) * | 1968-05-24 | 1971-02-23 | Nippon Oil Co Ltd | Process for oxidizing mercaptans to disulfides |
| US3954876A (en) * | 1972-01-24 | 1976-05-04 | Yeda Research And Development Co., Ltd. | Production of halo-substituted derivatives of acetophenone |
| US3801591A (en) * | 1972-06-12 | 1974-04-02 | Du Pont | Production of phthalocyanine pigment |
-
1976
- 1976-02-19 US US05/659,394 patent/US4048097A/en not_active Expired - Lifetime
-
1977
- 1977-02-04 CA CA271,115A patent/CA1103240A/en not_active Expired
- 1977-02-07 PT PT66161A patent/PT66161B/pt unknown
- 1977-02-07 ZA ZA00770693A patent/ZA77693B/xx unknown
- 1977-02-08 IN IN179/CAL/77A patent/IN155270B/en unknown
- 1977-02-11 YU YU357/77A patent/YU39380B/xx unknown
- 1977-02-16 FR FR7704346A patent/FR2341363A1/fr active Granted
- 1977-02-16 DE DE2706516A patent/DE2706516C3/de not_active Expired
- 1977-02-17 IT IT20392/77A patent/IT1115501B/it active
- 1977-02-17 SE SE7701773A patent/SE436697B/xx not_active IP Right Cessation
- 1977-02-17 ES ES456012A patent/ES456012A1/es not_active Expired
- 1977-02-18 BE BE175079A patent/BE851605A/xx not_active IP Right Cessation
- 1977-02-18 MX MX168085A patent/MX143797A/es unknown
- 1977-02-18 GB GB6876/77A patent/GB1569356A/en not_active Expired
- 1977-02-18 SU SU772454704A patent/SU673152A3/ru active
- 1977-02-18 AU AU22419/77A patent/AU504780B2/en not_active Expired
- 1977-02-18 BR BR7701049A patent/BR7701049A/pt unknown
- 1977-02-18 JP JP52017033A patent/JPS5922575B2/ja not_active Expired
- 1977-04-18 US US05/788,372 patent/US4078992A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES456012A1 (es) | 1978-06-01 |
| BR7701049A (pt) | 1977-10-18 |
| MX143797A (es) | 1981-07-16 |
| YU35777A (en) | 1983-02-28 |
| DE2706516A1 (de) | 1977-08-25 |
| SE7701773L (sv) | 1977-08-20 |
| DE2706516B2 (de) | 1978-10-05 |
| IN155270B (enExample) | 1985-01-12 |
| US4078992A (en) | 1978-03-14 |
| IT1115501B (it) | 1986-02-03 |
| CA1103240A (en) | 1981-06-16 |
| JPS52101684A (en) | 1977-08-25 |
| GB1569356A (en) | 1980-06-11 |
| JPS5922575B2 (ja) | 1984-05-28 |
| PT66161A (en) | 1977-03-01 |
| SE436697B (sv) | 1985-01-21 |
| PT66161B (en) | 1978-07-10 |
| YU39380B (en) | 1984-12-31 |
| SU673152A3 (ru) | 1979-07-05 |
| US4048097A (en) | 1977-09-13 |
| ZA77693B (en) | 1978-01-25 |
| FR2341363A1 (fr) | 1977-09-16 |
| BE851605A (fr) | 1977-06-16 |
| AU2241977A (en) | 1978-08-24 |
| AU504780B2 (en) | 1979-10-25 |
| FR2341363B1 (enExample) | 1980-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |