CA1124223A - Catalytic composite particularly useful for the oxidation of mercaptans contained in a sour petroleum distillate - Google Patents

Catalytic composite particularly useful for the oxidation of mercaptans contained in a sour petroleum distillate

Info

Publication number: CA1124223A
Authority: CA; Canada
Prior art keywords: catalytic composite; chloride; quaternary ammonium; hydroxide; oxidation catalyst
Prior art date: 1978-07-24
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

Application number

CA330,581A

Other languages

English (en)

French (fr)

Inventor

Robert R. Frame

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Honeywell UOP LLC

Original Assignee

UOP LLC

Priority date (The priority date 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 date listed.)

1978-07-24

Filing date

1979-06-26

Publication date

1982-05-25

1978-07-24 Priority claimed from US05/927,318 external-priority patent/US4206079A/en

1978-07-24 Priority claimed from US05/927,317 external-priority patent/US4157312A/en

1979-06-26 Application filed by UOP LLC filed Critical UOP LLC

1982-05-25 Application granted granted Critical

1982-05-25 Publication of CA1124223A publication Critical patent/CA1124223A/en

Status Expired legal-status Critical Current

Links

239000002131 composite material Substances 0.000 title claims abstract description 42
230000003197 catalytic effect Effects 0.000 title claims abstract description 39
230000003647 oxidation Effects 0.000 title claims abstract description 25
238000007254 oxidation reaction Methods 0.000 title claims abstract description 25
239000003209 petroleum derivative Substances 0.000 title abstract description 23
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title abstract description 20
239000003054 catalyst Substances 0.000 claims abstract description 38
229910052751 metal Inorganic materials 0.000 claims abstract description 36
239000002184 metal Substances 0.000 claims abstract description 36
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 23
239000013522 chelant Substances 0.000 claims abstract description 18
150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 17
239000007787 solid Substances 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 8
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
125000003118 aryl group Chemical group 0.000 claims abstract description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract description 5
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims abstract description 5
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims abstract description 5
229910002651 NO3 Inorganic materials 0.000 claims abstract description 5
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims abstract description 5
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims abstract description 5
229910019142 PO4 Inorganic materials 0.000 claims abstract description 5
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 5
230000000274 adsorptive effect Effects 0.000 claims abstract description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 5
239000010452 phosphate Substances 0.000 claims abstract description 5
229940095064 tartrate Drugs 0.000 claims abstract description 5
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
150000001450 anions Chemical group 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
229930195733 hydrocarbon Natural products 0.000 claims abstract description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 39
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 claims description 24
-1 hydrocarbon radical Chemical group 0.000 claims description 15
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical group [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 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 5
125000001453 quaternary ammonium group Chemical group 0.000 claims description 5
229910052720 vanadium Inorganic materials 0.000 claims description 4
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical group [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
239000000908 ammonium hydroxide Substances 0.000 claims description 3
JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 claims description 3
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 3
SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 claims description 3
229960000228 cetalkonium chloride Drugs 0.000 claims description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
CCEPFPXUJPGUDT-UHFFFAOYSA-M benzyl-dimethyl-octadecylazanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CCEPFPXUJPGUDT-UHFFFAOYSA-M 0.000 claims description 2
XLJOZOQVNCBJMT-UHFFFAOYSA-M benzyl-dimethyl-tetradecylazanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 XLJOZOQVNCBJMT-UHFFFAOYSA-M 0.000 claims description 2
LAUPTJWHHKNSCT-UHFFFAOYSA-M benzyl-hexadecyl-dimethylazanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 LAUPTJWHHKNSCT-UHFFFAOYSA-M 0.000 claims description 2
VEYPOAHLDFFNPD-UHFFFAOYSA-M benzyl-dodecyl-dimethylazanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 VEYPOAHLDFFNPD-UHFFFAOYSA-M 0.000 claims 1
235000021317 phosphate Nutrition 0.000 abstract description 4
150000004820 halides Chemical class 0.000 abstract description 2
150000001875 compounds Chemical class 0.000 abstract 1
238000000034 method Methods 0.000 description 25
230000008569 process Effects 0.000 description 20
239000000243 solution Substances 0.000 description 20
239000003463 adsorbent Substances 0.000 description 16
239000000306 component Substances 0.000 description 13
229940057007 petroleum distillate Drugs 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000003153 chemical reaction reagent Substances 0.000 description 11
239000003112 inhibitor Substances 0.000 description 8
239000006185 dispersion Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
150000001336 alkenes Chemical class 0.000 description 6
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 5
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
239000003518 caustics Substances 0.000 description 5
239000003350 kerosene Substances 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
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
229910017052 cobalt Inorganic materials 0.000 description 4
239000010941 cobalt Substances 0.000 description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
239000002245 particle Substances 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
230000001476 alcoholic effect Effects 0.000 description 3
150000003868 ammonium compounds Chemical class 0.000 description 3
229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000012876 carrier material Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
150000002019 disulfides Chemical class 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
150000003242 quaternary ammonium salts Chemical class 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
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000008901 benefit Effects 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
239000003610 charcoal Substances 0.000 description 2
238000010835 comparative analysis Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
229940050176 methyl chloride Drugs 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
238000012545 processing Methods 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
239000002904 solvent Substances 0.000 description 2
238000003860 storage Methods 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
238000012360 testing method Methods 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
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
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241000518994 Conta Species 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
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
230000009471 action Effects 0.000 description 1
239000012670 alkaline solution Substances 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
229910021529 ammonia Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 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
210000000988 bone and bone Anatomy 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
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
230000002844 continuous effect Effects 0.000 description 1
230000000875 corresponding effect Effects 0.000 description 1
WUPRCGRRQUZFAB-DEGKJRJSSA-N corrin Chemical compound N1C2CC\C1=C\C(CC/1)=N\C\1=C/C(CC\1)=N/C/1=C\C1=NC2CC1 WUPRCGRRQUZFAB-DEGKJRJSSA-N 0.000 description 1
150000001896 cresols Chemical class 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
230000001419 dependent effect 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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000010433 feldspar 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
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
150000004679 hydroxides Chemical class 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910052809 inorganic oxide Inorganic materials 0.000 description 1
230000003993 interaction Effects 0.000 description 1
150000002500 ions Chemical class 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
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides 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
238000006386 neutralization reaction Methods 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
239000003415 peat Substances 0.000 description 1
239000008188 pellet 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
239000005077 polysulfide Substances 0.000 description 1
150000008117 polysulfides Polymers 0.000 description 1
150000004032 porphyrins Chemical class 0.000 description 1
238000002360 preparation 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
239000000376 reactant Substances 0.000 description 1
230000009467 reduction Effects 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
239000000126 substance Substances 0.000 description 1
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 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
ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
238000012546 transfer Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-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

- 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
- 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
- B01J31/16—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
- 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
- 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
- B01J2531/80—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)
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)

CA330,581A 1978-07-24 1979-06-26 Catalytic composite particularly useful for the oxidation of mercaptans contained in a sour petroleum distillate Expired CA1124223A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US05/927,318 US4206079A (en)	1978-02-24	1978-07-24	Catalytic composite particularly useful for the oxidation of mercaptans contained in a sour petroleum distillate
US927,317		1978-07-24
US05/927,317 US4157312A (en)	1978-02-24	1978-07-24	Catalytic composite particularly useful for the oxidation of mercaptans contained in a sour petroleum distillate
US927,318		1986-11-04

Publications (1)

Publication Number	Publication Date
CA1124223A true CA1124223A (en)	1982-05-25

Family

ID=27129942

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA330,581A Expired CA1124223A (en)	1978-07-24	1979-06-26	Catalytic composite particularly useful for the oxidation of mercaptans contained in a sour petroleum distillate

Country Status (20)

Country	Link
AT (1)	AT374818B (de)
AU (1)	AU530970B2 (de)
BR (1)	BR7904695A (de)
CA (1)	CA1124223A (de)
DE (1)	DE2927685C2 (de)
DK (1)	DK310279A (de)
EG (1)	EG14061A (de)
ES (1)	ES482760A2 (de)
FR (1)	FR2433974A2 (de)
GB (1)	GB2027359B (de)
HU (1)	HU179813B (de)
IT (1)	IT1122275B (de)
MX (1)	MX154990A (de)
NL (1)	NL7904951A (de)
NO (1)	NO160493C (de)
PH (1)	PH14933A (de)
RO (1)	RO77061A (de)
SE (1)	SE436696B (de)
SU (1)	SU1095873A3 (de)
YU (1)	YU40569B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE102012202622A1 (de) *	2012-02-21	2013-08-22	Wacker Chemie Ag	Katalysator zur Carbonylierung carbonylierbarer Verbindungen in der Gasphase
MD4420C1 (ro) *	2012-06-26	2017-02-28	Оп "Matricon" Ооо	Aplicarea componentelor grele întunecate ale petrolului în calitate de catalizator la purificarea oxidativă de hidrogen sulfurat şi mercaptani uşori a compoziţiilor de hidrocarburi şi procedeu de purificare a compoziţiilor de hidrocarburi

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2988500A (en) *	1959-03-13	1961-06-13	Universal Oil Prod Co	Treatment of hydrocarbon distillates
US3164544A (en) *	1963-02-26	1965-01-05	Sun Oil Co	Oxidative sweetening with base and quaternary ammonium compound
FR1602191A (de) *	1968-12-31	1970-10-19
US4028269A (en) *	1975-08-21	1977-06-07	Uop Inc.	Process for the preparation of a solid bed catalyst system
ZA7740B (en) *	1976-01-14	1977-11-30	Uop Inc	Improved process for sweetening sour hydrocarbon distillates
US4070307A (en) *	1976-08-12	1978-01-24	Uop Inc.	Method of catalyst manufacture
US4087378A (en) *	1977-01-18	1978-05-02	Uop Inc.	Preparation of a supported metal phthalocyanine
US4124494A (en) *	1978-01-11	1978-11-07	Uop Inc.	Treating a petroleum distillate with a supported metal phthalocyanine and an alkanolamine hydroxide
US4124493A (en) *	1978-02-24	1978-11-07	Uop Inc.	Catalytic oxidation of mercaptan in petroleum distillate including alkaline reagent and substituted ammonium halide

1979
- 1979-06-19 AU AU48202/79A patent/AU530970B2/en not_active Ceased
- 1979-06-20 PH PH22672A patent/PH14933A/en unknown
- 1979-06-26 NL NL7904951A patent/NL7904951A/nl not_active Application Discontinuation
- 1979-06-26 CA CA330,581A patent/CA1124223A/en not_active Expired
- 1979-07-03 MX MX178332A patent/MX154990A/es unknown
- 1979-07-09 DE DE2927685A patent/DE2927685C2/de not_active Expired
- 1979-07-18 SE SE7906183A patent/SE436696B/sv not_active IP Right Cessation
- 1979-07-19 AT AT0501079A patent/AT374818B/de not_active IP Right Cessation
- 1979-07-19 FR FR7918690A patent/FR2433974A2/fr active Granted
- 1979-07-23 RO RO7998253A patent/RO77061A/ro unknown
- 1979-07-23 BR BR7904695A patent/BR7904695A/pt not_active IP Right Cessation
- 1979-07-23 DK DK310279A patent/DK310279A/da not_active Application Discontinuation
- 1979-07-23 HU HU79UO160A patent/HU179813B/hu not_active IP Right Cessation
- 1979-07-23 ES ES482760A patent/ES482760A2/es not_active Expired
- 1979-07-23 YU YU1791/79A patent/YU40569B/xx unknown
- 1979-07-23 SU SU792790958A patent/SU1095873A3/ru active
- 1979-07-23 NO NO792430A patent/NO160493C/no unknown
- 1979-07-23 IT IT24574/79A patent/IT1122275B/it active
- 1979-07-23 GB GB7925584A patent/GB2027359B/en not_active Expired
- 1979-07-24 EG EG442/79A patent/EG14061A/xx active

Also Published As

Publication number	Publication date
AU530970B2 (en)	1983-08-04
AT374818B (de)	1984-06-12
MX154990A (es)	1988-01-18
DK310279A (da)	1980-01-25
SE436696B (sv)	1985-01-21
IT7924574A0 (it)	1979-07-23
FR2433974B2 (de)	1984-08-24
ATA501079A (de)	1983-10-15
EG14061A (en)	1983-03-31
GB2027359A (en)	1980-02-20
NO160493C (no)	1989-04-26
PH14933A (en)	1982-01-29
NO792430L (no)	1980-01-25
SE7906183L (sv)	1980-01-25
AU4820279A (en)	1980-01-31
SU1095873A3 (ru)	1984-05-30
DE2927685C2 (de)	1987-03-26
FR2433974A2 (fr)	1980-03-21
ES482760A2 (es)	1980-07-01
IT1122275B (it)	1986-04-23
YU179179A (en)	1983-02-28
NL7904951A (nl)	1980-01-28
BR7904695A (pt)	1980-05-13
GB2027359B (en)	1982-10-06
NO160493B (no)	1989-01-16
HU179813B (en)	1982-12-28
DE2927685A1 (de)	1980-02-07
YU40569B (en)	1986-02-28
RO77061A (ro)	1982-03-24

Legal Events

Date	Code	Title	Description
1999-05-25	MKEX	Expiry

Publication	Publication Date	Title
US4157312A (en)	1979-06-05	Catalytic composite particularly useful for the oxidation of mercaptans contained in a sour petroleum distillate
US4290913A (en)	1981-09-22	Catalytic composite useful for the treatment of mercaptan-containing sour petroleum distillate
US4908122A (en)	1990-03-13	Process for sweetening a sour hydrocarbon fraction
US4159964A (en)	1979-07-03	Metal chelate catalyst and alkanolamine hydroxide on adsorptive support
EP0394571B1 (de)	1993-09-01	Verwendung einer katalytischen Zusammensetzung für das Süssen von sauren Erdöldestillaten
US4206079A (en)	1980-06-03	Catalytic composite particularly useful for the oxidation of mercaptans contained in a sour petroleum distillate
US4337147A (en)	1982-06-29	Catalytic composite and process for use
US4318825A (en)	1982-03-09	Catalytic composite, and method of manufacture
US4127474A (en)	1978-11-28	Treating a petroleum distillate with an alkanolamine hydroxide and a supported oxidation catalyst impregnated with polynuclear aromatic sulfonic acid
US4913802A (en)	1990-04-03	Process for sweetening a sour hydrocarbon fraction
EP0153833B1 (de)	1988-04-27	Verfahren zum Süssen von sauren Merkaptan enthaltenden Kohlenwasserstofffraktionen
US4203827A (en)	1980-05-20	Process for treating sour petroleum distillates
US4213877A (en)	1980-07-22	Method of reactivating a catalytic composite of an adsorptive carrier material and a mercaptan oxidation catalyst
US4260479A (en)	1981-04-07	Catalytic oxidation of mercaptan in sour petroleum distillate
US4364843A (en)	1982-12-21	Catalytic composite, method of manufacture, and process for use
US4897180A (en)	1990-01-30	Catalytic composite and process for mercaptan sweetening
EP0396934B1 (de)	1993-03-10	Nichtalkalisches Süssen von Kohlenwasserstofffraktionen
JPH0334369B2 (de)	1991-05-22
US4293442A (en)	1981-10-06	Catalytic composite, method of manufacture, and process for use
US4290917A (en)	1981-09-22	Method of manufacturing a catalytic composite
CA1124223A (en)	1982-05-25	Catalytic composite particularly useful for the oxidation of mercaptans contained in a sour petroleum distillate
US4276194A (en)	1981-06-30	Catalytic composite, method of manufacture, and process for use
US4250022A (en)	1981-02-10	Catalytic oxidation of mercaptan in petroleum distillate
US4121997A (en)	1978-10-24	Treating a petroleum distillate with a supported metal phthalocyanine and an alkaline reagent containing alkanolamine halide
US4308169A (en)	1981-12-29	Method of reactivating a catalytic composite of a carrier material and a mercaptan oxidation catalyst