HU181983B - Process for catalytic releasing petroleum fractions from tiols - Google Patents
Process for catalytic releasing petroleum fractions from tiols Download PDFInfo
- Publication number
- HU181983B HU181983B HU79UO155A HUUO000155A HU181983B HU 181983 B HU181983 B HU 181983B HU 79UO155 A HU79UO155 A HU 79UO155A HU UO000155 A HUUO000155 A HU UO000155A HU 181983 B HU181983 B HU 181983B
- Authority
- HU
- Hungary
- Prior art keywords
- chloride
- alkyl
- substituted ammonium
- formula
- dimethylbenzyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 230000003197 catalytic effect Effects 0.000 title abstract description 5
- 239000003208 petroleum Substances 0.000 title description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- -1 ammonium halide Chemical class 0.000 claims description 19
- 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 claims description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 7
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- 125000006182 dimethyl benzyl group Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 claims 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 claims description 2
- SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 claims description 2
- 229960000228 cetalkonium chloride Drugs 0.000 claims description 2
- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 claims description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 2
- 239000003209 petroleum derivative Substances 0.000 abstract description 19
- 230000003647 oxidation Effects 0.000 abstract description 6
- 238000007254 oxidation reaction Methods 0.000 abstract description 6
- 239000007787 solid Substances 0.000 abstract description 6
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract description 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000002131 composite material Substances 0.000 abstract 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 230000000274 adsorptive effect Effects 0.000 abstract 1
- 150000001450 anions Chemical group 0.000 abstract 1
- 239000013522 chelant Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 229940095064 tartrate Drugs 0.000 abstract 1
- 150000003573 thiols Chemical class 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 14
- 239000003463 adsorbent Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 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
- 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
- 239000003513 alkali Substances 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 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 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- OZISYDUERWIGSU-UHFFFAOYSA-M benzyl-didodecyl-methylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(CCCCCCCCCCCC)CC1=CC=CC=C1 OZISYDUERWIGSU-UHFFFAOYSA-M 0.000 description 1
- NBPIESHSZVPURH-UHFFFAOYSA-M benzyl-dihexadecyl-methylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(CCCCCCCCCCCCCCCC)CC1=CC=CC=C1 NBPIESHSZVPURH-UHFFFAOYSA-M 0.000 description 1
- MOVYDMDPASTSTN-UHFFFAOYSA-M benzyl-methyl-di(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(CCCCCCCCCCCCCC)CC1=CC=CC=C1 MOVYDMDPASTSTN-UHFFFAOYSA-M 0.000 description 1
- JLSSEXVNHGDLNN-UHFFFAOYSA-M benzyl-methyl-dioctadecylazanium;chloride Chemical class [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(CCCCCCCCCCCCCCCCCC)CC1=CC=CC=C1 JLSSEXVNHGDLNN-UHFFFAOYSA-M 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 230000009849 deactivation Effects 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
- 238000004090 dissolution Methods 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
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- RNYJXPUAFDFIQJ-UHFFFAOYSA-N hydron;octadecan-1-amine;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[NH3+] RNYJXPUAFDFIQJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- NEXZCFUBZJBRCP-UHFFFAOYSA-N naphthalen-1-ylmethylazanium;chloride Chemical compound Cl.C1=CC=C2C(CN)=CC=CC2=C1 NEXZCFUBZJBRCP-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003826 tablet Substances 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
- 235000020234 walnut Nutrition 0.000 description 1
- 239000002023 wood 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
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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
- C10G27/10—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
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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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
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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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/845—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
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- 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 (1)
| Publication Number | Publication Date |
|---|---|
| HU181983B true HU181983B (en) | 1983-11-28 |
Family
ID=25376937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79UO155A HU181983B (en) | 1978-02-24 | 1979-02-22 | Process for catalytic releasing petroleum fractions from tiols |
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
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |