DE2905581C2 - Verfahren zur Oxidation von Mercaptanen in einem sauren Erdöldestillat - Google Patents
Verfahren zur Oxidation von Mercaptanen in einem sauren ErdöldestillatInfo
- Publication number
- DE2905581C2 DE2905581C2 DE2905581A DE2905581A DE2905581C2 DE 2905581 C2 DE2905581 C2 DE 2905581C2 DE 2905581 A DE2905581 A DE 2905581A DE 2905581 A DE2905581 A DE 2905581A DE 2905581 C2 DE2905581 C2 DE 2905581C2
- Authority
- DE
- Germany
- Prior art keywords
- chloride
- phthalocyanine
- oxidation
- mercaptans
- petroleum distillate
- 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
- 239000003209 petroleum derivative Substances 0.000 title claims description 21
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims description 13
- 230000003647 oxidation Effects 0.000 title claims description 13
- 238000007254 oxidation reaction Methods 0.000 title claims description 13
- 230000002378 acidificating effect Effects 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 10
- 239000003054 catalyst Substances 0.000 claims description 22
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 14
- -1 ammonium halide Chemical class 0.000 claims description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 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 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 239000003350 kerosene Substances 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 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 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000003502 gasoline Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 2
- OCBHHZMJRVXXQK-UHFFFAOYSA-M benzyl-dimethyl-tetradecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 OCBHHZMJRVXXQK-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 description 2
- 229960000228 cetalkonium chloride Drugs 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 description 2
- YLGQLQSDQXOIBI-UHFFFAOYSA-N (29h,31h-phthalocyaninato(2-)-n29,n30,n31,n32)platinum Chemical compound [Pt+2].[N-]1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)[N-]3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 YLGQLQSDQXOIBI-UHFFFAOYSA-N 0.000 description 1
- KMHSUNDEGHRBNV-UHFFFAOYSA-N 2,4-dichloropyrimidine-5-carbonitrile Chemical compound ClC1=NC=C(C#N)C(Cl)=N1 KMHSUNDEGHRBNV-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- IXWIAFSBWGYQOE-UHFFFAOYSA-M aluminum;magnesium;oxygen(2-);silicon(4+);hydroxide;tetrahydrate Chemical compound O.O.O.O.[OH-].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Mg+2].[Al+3].[Si+4].[Si+4].[Si+4].[Si+4] IXWIAFSBWGYQOE-UHFFFAOYSA-M 0.000 description 1
- HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- WDEQGLDWZMIMJM-UHFFFAOYSA-N benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound OCC1CC(O)CN1C(=O)OCC1=CC=CC=C1 WDEQGLDWZMIMJM-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052621 halloysite Inorganic materials 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003077 lignite Substances 0.000 description 1
- LBAIJNRSTQHDMR-UHFFFAOYSA-N magnesium phthalocyanine Chemical compound [Mg].C12=CC=CC=C2C(N=C2NC(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2N1 LBAIJNRSTQHDMR-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MCTALTNNXRUUBZ-UHFFFAOYSA-N molport-000-691-724 Chemical compound [Pd+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 MCTALTNNXRUUBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008137 solubility enhancer Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
- 229910003452 thorium oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1616—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts
-
- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0239—Quaternary ammonium compounds
-
- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0254—Nitrogen containing compounds on mineral substrates
-
- 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
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
- C10G27/04—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
- C10G27/06—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen in the presence of alkaline solutions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
- C10G27/04—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
- C10G27/10—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen in the presence of metal-containing organic complexes, e.g. chelates, or cationic ion-exchange resins
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
-
- 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
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
-
- 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
- B01J2540/30—Non-coordinating groups comprising sulfur
- B01J2540/34—Sulfonyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/880,723 US4124493A (en) | 1978-02-24 | 1978-02-24 | Catalytic oxidation of mercaptan in petroleum distillate including alkaline reagent and substituted ammonium halide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2905581A1 DE2905581A1 (de) | 1979-09-06 |
| DE2905581C2 true DE2905581C2 (de) | 1982-06-09 |
Family
ID=25376937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2905581A Expired DE2905581C2 (de) | 1978-02-24 | 1979-02-14 | Verfahren zur Oxidation von Mercaptanen in einem sauren Erdöldestillat |
Country Status (33)
| Country | Link |
|---|---|
| US (3) | US4124493A (OSRAM) |
| JP (1) | JPS54126204A (OSRAM) |
| AR (1) | AR228127A1 (OSRAM) |
| AT (1) | AT368543B (OSRAM) |
| AU (1) | AU518753B2 (OSRAM) |
| BE (1) | BE874264A (OSRAM) |
| BG (1) | BG48340A3 (OSRAM) |
| BR (1) | BR7901145A (OSRAM) |
| CA (1) | CA1124197A (OSRAM) |
| DE (1) | DE2905581C2 (OSRAM) |
| DK (1) | DK151972C (OSRAM) |
| EG (1) | EG14010A (OSRAM) |
| ES (1) | ES477956A1 (OSRAM) |
| FI (1) | FI64390C (OSRAM) |
| FR (1) | FR2418270A1 (OSRAM) |
| GB (1) | GB2017141B (OSRAM) |
| GR (1) | GR67627B (OSRAM) |
| HU (1) | HU181983B (OSRAM) |
| IE (1) | IE47834B1 (OSRAM) |
| IS (1) | IS1085B6 (OSRAM) |
| IT (1) | IT1112028B (OSRAM) |
| MX (1) | MX150357A (OSRAM) |
| MY (1) | MY8500334A (OSRAM) |
| NL (1) | NL7901397A (OSRAM) |
| NO (1) | NO157588C (OSRAM) |
| PT (1) | PT69216B (OSRAM) |
| RO (1) | RO78591A (OSRAM) |
| SE (1) | SE431344B (OSRAM) |
| SG (1) | SG32385G (OSRAM) |
| SU (1) | SU878199A3 (OSRAM) |
| TR (1) | TR20424A (OSRAM) |
| YU (1) | YU40740B (OSRAM) |
| ZA (1) | ZA79783B (OSRAM) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4124493A (en) * | 1978-02-24 | 1978-11-07 | Uop Inc. | Catalytic oxidation of mercaptan in petroleum distillate including alkaline reagent and substituted ammonium halide |
| AU530970B2 (en) * | 1978-07-24 | 1983-08-04 | Uop Inc. | Catalytic composite |
| DE2952989A1 (en) * | 1978-07-26 | 1981-01-08 | J Clark | Improvements in the stabilisation of hygroscopic salts |
| US4293442A (en) * | 1979-08-10 | 1981-10-06 | Uop Inc. | Catalytic composite, method of manufacture, and process for use |
| US4250022A (en) * | 1979-08-15 | 1981-02-10 | Uop Inc. | Catalytic oxidation of mercaptan in petroleum distillate |
| US4318825A (en) * | 1979-08-15 | 1982-03-09 | Frame Robert R | Catalytic composite, and method of manufacture |
| US4260479A (en) * | 1979-09-27 | 1981-04-07 | Uop Inc. | Catalytic oxidation of mercaptan in sour petroleum distillate |
| US4290917A (en) * | 1979-10-01 | 1981-09-22 | Uop Inc. | Method of manufacturing a catalytic composite |
| US4324650A (en) * | 1979-10-01 | 1982-04-13 | Uop Inc. | Catalytic composite and process for use |
| US4276194A (en) * | 1979-10-01 | 1981-06-30 | Uop Inc. | Catalytic composite, method of manufacture, and process for use |
| US4290916A (en) * | 1979-10-01 | 1981-09-22 | Uop Inc. | Catalytic composite, method of manufacture, and process for use |
| US4337147A (en) * | 1979-11-07 | 1982-06-29 | Uop Inc. | Catalytic composite and process for use |
| US4354926A (en) * | 1980-01-04 | 1982-10-19 | Uop Inc. | Catalytic composite and process for use |
| US4295993A (en) * | 1980-01-04 | 1981-10-20 | Uop Inc. | Catalytic composite, method of manufacture and process for use |
| US4298463A (en) * | 1980-07-11 | 1981-11-03 | Uop Inc. | Method of treating a sour petroleum distillate |
| US4320029A (en) * | 1980-07-17 | 1982-03-16 | Uop Inc. | Catalytic composite, method of manufacture, and process for use |
| US4360421A (en) * | 1980-07-17 | 1982-11-23 | Uop Inc. | Method for treating mercaptans contained in a sour petroleum distillate |
| US4746494A (en) * | 1985-05-30 | 1988-05-24 | Merichem Company | Treatment of sour hydrocarbon distillate |
| US4675100A (en) * | 1985-05-30 | 1987-06-23 | Merichem Company | Treatment of sour hydrocarbon distillate |
| US4725420A (en) * | 1985-09-25 | 1988-02-16 | Toa Nenryo Kogyo Kabushiki Kaisha | Process for the production of silanes |
| US4753722A (en) * | 1986-06-17 | 1988-06-28 | Merichem Company | Treatment of mercaptan-containing streams utilizing nitrogen based promoters |
| US4775462A (en) * | 1987-06-22 | 1988-10-04 | Uop Inc. | Non-oxidative method of sweetening a sour hydrocarbon fraction |
| US4897180A (en) * | 1988-02-05 | 1990-01-30 | Uop | Catalytic composite and process for mercaptan sweetening |
| US4824818A (en) * | 1988-02-05 | 1989-04-25 | Uop Inc. | Catalytic composite and process for mercaptan sweetening |
| DE3814167A1 (de) * | 1988-04-27 | 1989-11-09 | Bayer Ag | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung |
| US4908122A (en) * | 1989-05-08 | 1990-03-13 | Uop | Process for sweetening a sour hydrocarbon fraction |
| US4913802A (en) * | 1989-05-08 | 1990-04-03 | Uop | Process for sweetening a sour hydrocarbon fraction |
| AU618886B2 (en) * | 1989-05-08 | 1992-01-09 | Uop | Caustic-free sweetening of sour hydrocarbon streams |
| US4923596A (en) * | 1989-05-22 | 1990-05-08 | Uop | Use of quaternary ammonium compounds in a liquid/liquid process for sweetening a sour hydrocarbon fraction |
| US4929340A (en) * | 1989-07-31 | 1990-05-29 | Uop | Catalyst and process for sweetening a sour hydrocarbon fraction using dipolar compounds |
| US5039398A (en) * | 1990-03-19 | 1991-08-13 | Uop | Elimination of caustic prewash in the fixed bed sweetening of high naphthenic acids hydrocarbons |
| US5180484A (en) * | 1990-08-27 | 1993-01-19 | Uop | Caustic free liquid/liquid process for sweeting a sour hydrocarbon fraction |
| US5204306A (en) * | 1990-08-27 | 1993-04-20 | Uop | Caustic free catalyst for use in a liquid/liquid process for sweetening a sour hydrocarbon fraction |
| US5273646A (en) * | 1990-08-27 | 1993-12-28 | Uop | Process for improving the activity of a mercaptan oxidation catalyst |
| US5093296A (en) * | 1990-08-27 | 1992-03-03 | Uop | Caustic free liquid/liquid process for sweetening a sour hydrocarbon fraction |
| GB9023257D0 (en) * | 1990-10-25 | 1990-12-05 | British Petroleum Co Plc | Desulphurisation of oil |
| US5200062A (en) * | 1991-06-17 | 1993-04-06 | Exxon Research And Engineering Company | Process for removing elemental sulfur from fluids |
| US5218147A (en) * | 1992-02-10 | 1993-06-08 | Phillips Petroleum Company | Stable polysulfides and process therefor |
| US5232887A (en) * | 1992-04-02 | 1993-08-03 | Uop | Catalyst for sweetening a sour hydrocarbon fraction |
| US5318936A (en) * | 1992-09-23 | 1994-06-07 | Uop | Catalyst for sweetening a sour hydrocarbon fraction containing metal oxide solid solution and magnesium oxide |
| US5413704A (en) * | 1993-11-15 | 1995-05-09 | Uop | Process for sweetening a sour hydrocarbon fraction using a mixture of a supported metal chelate and a solid base |
| US5413701A (en) * | 1993-11-15 | 1995-05-09 | Uop | Process for sweetening a sour hydrocarbon fraction using a supported metal chelate and a solid base |
| US6306288B1 (en) | 1998-04-17 | 2001-10-23 | Uop Llc | Process for removing sulfur compounds from hydrocarbon streams |
| CA2407066A1 (en) * | 2000-04-18 | 2001-10-25 | Exxonmobil Research And Engineering Company | Selective hydroprocessing and mercaptan removal |
| US6488840B1 (en) * | 2000-04-18 | 2002-12-03 | Exxonmobil Research And Engineering Company | Mercaptan removal from petroleum streams (Law950) |
| US6352640B1 (en) | 2000-04-18 | 2002-03-05 | Exxonmobil Research And Engineering Company | Caustic extraction of mercaptans (LAW966) |
| US7223332B1 (en) | 2003-10-21 | 2007-05-29 | Uop Llc | Reactor and process for mercaptan oxidation and separation in the same vessel |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2560374A (en) * | 1949-02-19 | 1951-07-10 | Standard Oil Dev Co | Treatment of sour petroleum distillates |
| US2671048A (en) * | 1951-03-01 | 1954-03-02 | Universal Oil Prod Co | Treatment of hydrocarbon distillates |
| US2744854A (en) * | 1952-06-30 | 1956-05-08 | Universal Oil Prod Co | Oxidation of mercaptans |
| US3164544A (en) * | 1963-02-26 | 1965-01-05 | Sun Oil Co | Oxidative sweetening with base and quaternary ammonium compound |
| US3978137A (en) * | 1975-03-14 | 1976-08-31 | Universal Oil Products Company | Oxidation of sulfur-containing compounds |
| US4003827A (en) * | 1975-06-12 | 1977-01-18 | Universal Oil Products Company | Mercaptan conversion process for a petroleum distillate charge stock |
| US4028269A (en) * | 1975-08-21 | 1977-06-07 | Uop Inc. | Process for the preparation of a solid bed catalyst system |
| US4033860A (en) * | 1975-09-10 | 1977-07-05 | Uop Inc. | Mercaptan conversion process |
| US4070271A (en) * | 1975-09-22 | 1978-01-24 | Uop Inc. | Catalytic oxidation of mercaptans and removal of naphthenic acids, catalyst toxins, and toxin precursors from petroleum distillates |
| ZA7740B (en) * | 1976-01-14 | 1977-11-30 | Uop Inc | Improved process for sweetening sour hydrocarbon distillates |
| US4124531A (en) * | 1977-01-03 | 1978-11-07 | Uop Inc. | Catalytic composite for the treatment of sour petroleum distillates |
| US4124494A (en) * | 1978-01-11 | 1978-11-07 | Uop Inc. | Treating a petroleum distillate with a supported metal phthalocyanine and an alkanolamine hydroxide |
| US4121997A (en) * | 1978-01-11 | 1978-10-24 | Uop Inc. | Treating a petroleum distillate with a supported metal phthalocyanine and an alkaline reagent containing alkanolamine halide |
| US4124493A (en) * | 1978-02-24 | 1978-11-07 | Uop Inc. | Catalytic oxidation of mercaptan in petroleum distillate including alkaline reagent and substituted ammonium halide |
-
1978
- 1978-02-24 US US05/880,723 patent/US4124493A/en not_active Expired - Lifetime
- 1978-07-24 US US05/927,317 patent/US4157312A/en not_active Expired - Lifetime
- 1978-07-28 US US05/929,054 patent/US4156641A/en not_active Expired - Lifetime
-
1979
- 1979-02-09 FR FR7903339A patent/FR2418270A1/fr active Granted
- 1979-02-12 IE IE264/79A patent/IE47834B1/en unknown
- 1979-02-13 PT PT6921679A patent/PT69216B/pt unknown
- 1979-02-13 GR GR58346A patent/GR67627B/el unknown
- 1979-02-14 IS IS2479A patent/IS1085B6/is unknown
- 1979-02-14 DE DE2905581A patent/DE2905581C2/de not_active Expired
- 1979-02-14 AU AU44230/79A patent/AU518753B2/en not_active Ceased
- 1979-02-19 CA CA321,749A patent/CA1124197A/en not_active Expired
- 1979-02-19 BE BE193539A patent/BE874264A/xx not_active IP Right Cessation
- 1979-02-20 ZA ZA79783A patent/ZA79783B/xx unknown
- 1979-02-20 SE SE7901499A patent/SE431344B/sv unknown
- 1979-02-21 EG EG115/79A patent/EG14010A/xx active
- 1979-02-21 YU YU421/79A patent/YU40740B/xx unknown
- 1979-02-21 MX MX176673A patent/MX150357A/es unknown
- 1979-02-21 BR BR7901145A patent/BR7901145A/pt unknown
- 1979-02-22 ES ES477956A patent/ES477956A1/es not_active Expired
- 1979-02-22 AR AR275589A patent/AR228127A1/es active
- 1979-02-22 NL NL7901397A patent/NL7901397A/xx not_active Application Discontinuation
- 1979-02-22 HU HU79UO155A patent/HU181983B/hu not_active IP Right Cessation
- 1979-02-23 DK DK079379A patent/DK151972C/da not_active IP Right Cessation
- 1979-02-23 NO NO790618A patent/NO157588C/no unknown
- 1979-02-23 GB GB7906586A patent/GB2017141B/en not_active Expired
- 1979-02-23 FI FI790618A patent/FI64390C/fi not_active IP Right Cessation
- 1979-02-23 TR TR20424A patent/TR20424A/xx unknown
- 1979-02-23 AT AT0142779A patent/AT368543B/de not_active IP Right Cessation
- 1979-02-23 SU SU792737952A patent/SU878199A3/ru active
- 1979-02-23 IT IT20508/79A patent/IT1112028B/it active
- 1979-02-23 BG BG042641A patent/BG48340A3/xx unknown
- 1979-02-23 JP JP1985279A patent/JPS54126204A/ja active Granted
- 1979-02-24 RO RO7996721A patent/RO78591A/ro unknown
-
1985
- 1985-04-30 SG SG32385A patent/SG32385G/en unknown
- 1985-12-30 MY MY334/85A patent/MY8500334A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
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| 8162 | Independent application | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |