CS217971B2 - Method of processing acidic petroleum distillates with contents of the mercaptane - Google Patents

Method of processing acidic petroleum distillates with contents of the mercaptane Download PDF

Info

Publication number: CS217971B2
Authority: CS; Czechoslovakia
Prior art keywords: catalyst composition; quaternary ammonium; processing zone; hydroxide; ammonium compound
Prior art date: 1978-08-28

Application number

CS795760A

Other languages

Czech (cs)

English (en)

Inventor

Robert Frame

Original Assignee

Uop Inc

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.)

1978-08-28

Filing date

1979-08-24

Publication date

1983-02-25

1979-08-24 Application filed by Uop Inc filed Critical Uop Inc

1983-02-25 Publication of CS217971B2 publication Critical patent/CS217971B2/cs

Links

239000003209 petroleum derivative Substances 0.000 title claims abstract description 57
238000000034 method Methods 0.000 title claims abstract description 50
238000012545 processing Methods 0.000 title claims description 45
230000002378 acidificating effect Effects 0.000 title description 11
239000003054 catalyst Substances 0.000 claims abstract description 85
229910052751 metal Inorganic materials 0.000 claims abstract description 40
239000002184 metal Substances 0.000 claims abstract description 40
150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 32
230000003647 oxidation Effects 0.000 claims abstract description 26
238000007254 oxidation reaction Methods 0.000 claims abstract description 26
239000007787 solid Substances 0.000 claims abstract description 24
239000013522 chelant Substances 0.000 claims abstract description 16
230000003197 catalytic effect Effects 0.000 claims abstract description 10
239000007800 oxidant agent Substances 0.000 claims abstract description 9
239000000203 mixture Substances 0.000 claims description 58
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 42
239000002253 acid Substances 0.000 claims description 30
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
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 19
238000001179 sorption measurement Methods 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 11
239000003795 chemical substances by application Substances 0.000 claims description 8
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
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 7
125000002877 alkyl aryl group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
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
VEYPOAHLDFFNPD-UHFFFAOYSA-M benzyl-dodecyl-dimethylazanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 VEYPOAHLDFFNPD-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
125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract description 21
239000003463 adsorbent Substances 0.000 abstract description 8
239000003153 chemical reaction reagent Substances 0.000 abstract description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 5
229910052717 sulfur Inorganic materials 0.000 abstract description 5
239000011593 sulfur Substances 0.000 abstract description 5
239000002131 composite material Substances 0.000 abstract 4
239000000243 solution Substances 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
230000002401 inhibitory effect Effects 0.000 description 11
-1 aromatic thiols Chemical class 0.000 description 9
150000001875 compounds Chemical class 0.000 description 9
230000009849 deactivation Effects 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000006185 dispersion Substances 0.000 description 8
239000002245 particle Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
150000001336 alkenes Chemical class 0.000 description 7
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
239000003518 caustics Substances 0.000 description 6
229910017052 cobalt Inorganic materials 0.000 description 6
239000010941 cobalt Substances 0.000 description 6
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 6
150000002019 disulfides Chemical class 0.000 description 6
230000002779 inactivation Effects 0.000 description 6
239000003350 kerosene Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 5
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000003610 charcoal Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
230000001476 alcoholic effect Effects 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
238000000151 deposition Methods 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
229910052720 vanadium Inorganic materials 0.000 description 3
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
150000003868 ammonium compounds Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
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
230000008021 deposition Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
150000004032 porphyrins Chemical class 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 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
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
OUPXFMKMVZOCCX-UHFFFAOYSA-N 2,2,2-triphenylethylazanium;hydroxide Chemical compound [OH-].C=1C=CC=CC=1C(C=1C=CC=CC=1)(C[NH3+])C1=CC=CC=C1 OUPXFMKMVZOCCX-UHFFFAOYSA-N 0.000 description 1
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
WHPOHUHRAVELNJ-UHFFFAOYSA-N 3,3,3-triphenylpropylazanium;hydroxide Chemical compound [OH-].C=1C=CC=CC=1C(C=1C=CC=CC=1)(CC[NH3+])C1=CC=CC=C1 WHPOHUHRAVELNJ-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
229910052776 Thorium Inorganic materials 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
238000010521 absorption reaction Methods 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
235000012211 aluminium silicate Nutrition 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
229960000892 attapulgite Drugs 0.000 description 1
239000011324 bead Substances 0.000 description 1
YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
SXVFRTBMWHHATP-UHFFFAOYSA-M butyl(triphenyl)azanium;hydroxide Chemical compound [OH-].C=1C=CC=CC=1[N+](C=1C=CC=CC=1)(CCCC)C1=CC=CC=C1 SXVFRTBMWHHATP-UHFFFAOYSA-M 0.000 description 1
HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical class [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
239000003575 carbonaceous material Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000012993 chemical processing Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
150000001805 chlorine compounds Chemical group 0.000 description 1
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 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
ZRCALJGFKUIRIV-UHFFFAOYSA-M dibenzyl(dibutyl)azanium;hydroxide Chemical compound [OH-].C=1C=CC=CC=1C[N+](CCCC)(CCCC)CC1=CC=CC=C1 ZRCALJGFKUIRIV-UHFFFAOYSA-M 0.000 description 1
OLOYUTDDPFIKMB-UHFFFAOYSA-M dibenzyl(diethyl)azanium;hydroxide Chemical compound [OH-].C=1C=CC=CC=1C[N+](CC)(CC)CC1=CC=CC=C1 OLOYUTDDPFIKMB-UHFFFAOYSA-M 0.000 description 1
KDSGPAZGWJOGTA-UHFFFAOYSA-M dibenzyl(dimethyl)azanium;hydroxide Chemical compound [OH-].C=1C=CC=CC=1C[N+](C)(C)CC1=CC=CC=C1 KDSGPAZGWJOGTA-UHFFFAOYSA-M 0.000 description 1
NGWPPNQRYULSAV-UHFFFAOYSA-M dibenzyl(dipropyl)azanium;hydroxide Chemical compound [OH-].C=1C=CC=CC=1C[N+](CCC)(CCC)CC1=CC=CC=C1 NGWPPNQRYULSAV-UHFFFAOYSA-M 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 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
229930195733 hydrocarbon Natural products 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910052809 inorganic oxide Inorganic materials 0.000 description 1
229910052742 iron 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
229910052744 lithium Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 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
229910052759 nickel Inorganic materials 0.000 description 1
238000010606 normalization Methods 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052625 palygorskite Inorganic materials 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
150000002989 phenols Chemical class 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910052697 platinum Inorganic materials 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
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 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
125000001453 quaternary ammonium group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
238000003860 storage Methods 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
229940095064 tartrate Drugs 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
239000011135 tin Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
IUQZIGVJJRTQEV-UHFFFAOYSA-N tritylazanium;hydroxide Chemical compound O.C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 IUQZIGVJJRTQEV-UHFFFAOYSA-N 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000009736 wetting Methods 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

- 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
- C10G53/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes
- C10G53/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only
- C10G53/14—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only including at least one oxidation step
- 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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
- B01J31/183—Ligands comprising condensed ring systems, e.g. acridine, carbazole with more than one complexing nitrogen atom, e.g. phenanthroline
- C—CHEMISTRY; METALLURGY
- 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
- B01J2531/80—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)
Oil, Petroleum & Natural Gas (AREA)
Inorganic Chemistry (AREA)
Materials Engineering (AREA)
General Chemical & Material Sciences (AREA)
Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Catalysts (AREA)

CS795760A 1978-08-28 1979-08-24 Method of processing acidic petroleum distillates with contents of the mercaptane CS217971B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/940,041 US4203827A (en)	1978-08-28	1978-08-28	Process for treating sour petroleum distillates

Publications (1)

Publication Number	Publication Date
CS217971B2 true CS217971B2 (en)	1983-02-25

Family

ID=25474119

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS795760A CS217971B2 (en)	1978-08-28	1979-08-24	Method of processing acidic petroleum distillates with contents of the mercaptane

Country Status (15)

Country	Link
US (1)	US4203827A (fr)
AU (1)	AU529098B2 (fr)
BE (1)	BE878410A (fr)
CA (1)	CA1127990A (fr)
CS (1)	CS217971B2 (fr)
DD (1)	DD145637A5 (fr)
GB (1)	GB2034744B (fr)
IS (1)	IS1083B6 (fr)
LU (1)	LU81635A1 (fr)
MW (1)	MW2479A1 (fr)
MX (1)	MX153074A (fr)
NZ (1)	NZ191397A (fr)
OA (1)	OA06330A (fr)
ZA (1)	ZA794493B (fr)
ZM (1)	ZM7479A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4753722A (en) *	1986-06-17	1988-06-28	Merichem Company	Treatment of mercaptan-containing streams utilizing nitrogen based promoters
US4908122A (en) *	1989-05-08	1990-03-13	Uop	Process for sweetening a sour hydrocarbon fraction
AU618886B2 (en) *	1989-05-08	1992-01-09	Uop	Caustic-free sweetening of sour hydrocarbon streams
US4913802A (en) *	1989-05-08	1990-04-03	Uop	Process for sweetening a sour hydrocarbon fraction
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
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
US5180484A (en) *	1990-08-27	1993-01-19	Uop	Caustic free liquid/liquid process for sweeting a sour hydrocarbon fraction
US5093296A (en) *	1990-08-27	1992-03-03	Uop	Caustic free 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
US10703995B2 (en) *	2017-03-14	2020-07-07	Alternative Petroleum Technologies, Inc.	System and method for liquid hydrocarbon desulfurization
EP3645671A4 (fr)	2017-06-26	2021-03-31	Alternative Petroleum Technologies, Inc.	Système et procédé de désulfuration d'hydrocarbures liquides

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2744854A (en) *	1952-06-30	1956-05-08	Universal Oil Prod Co	Oxidation of mercaptans
US3108081A (en) *	1959-07-17	1963-10-22	Universal Oil Prod Co	Catalyst and manufacture thereof
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

1978
- 1978-08-28 US US05/940,041 patent/US4203827A/en not_active Expired - Lifetime
1979
- 1979-08-22 AU AU50170/79A patent/AU529098B2/en not_active Ceased
- 1979-08-22 IS IS2509A patent/IS1083B6/is unknown
- 1979-08-24 ZA ZA00794493A patent/ZA794493B/xx unknown
- 1979-08-24 CS CS795760A patent/CS217971B2/cs unknown
- 1979-08-24 BE BE0/196865A patent/BE878410A/fr not_active IP Right Cessation
- 1979-08-24 GB GB7929519A patent/GB2034744B/en not_active Expired
- 1979-08-27 NZ NZ191397A patent/NZ191397A/xx unknown
- 1979-08-27 MX MX179077A patent/MX153074A/es unknown
- 1979-08-28 LU LU81635A patent/LU81635A1/fr unknown
- 1979-08-28 DD DD79215239A patent/DD145637A5/de not_active IP Right Cessation
- 1979-08-28 MW MW24/79A patent/MW2479A1/xx unknown
- 1979-08-28 OA OA56889A patent/OA06330A/fr unknown
- 1979-08-28 CA CA334,594A patent/CA1127990A/fr not_active Expired
- 1979-08-28 ZM ZM74/79A patent/ZM7479A1/xx unknown

Also Published As

Publication number	Publication date
IS1083B6 (is)	1982-07-03
LU81635A1 (fr)	1979-12-07
CA1127990A (fr)	1982-07-20
AU529098B2 (en)	1983-05-26
ZM7479A1 (en)	1980-07-21
NZ191397A (en)	1981-03-16
US4203827A (en)	1980-05-20
IS2509A7 (is)	1980-02-29
BE878410A (fr)	1979-12-17
GB2034744A (en)	1980-06-11
OA06330A (fr)	1981-06-30
MX153074A (es)	1986-07-28
AU5017079A (en)	1980-03-06
MW2479A1 (en)	1981-04-08
DD145637A5 (de)	1980-12-24
ZA794493B (en)	1980-08-27
GB2034744B (en)	1983-01-19

Publication	Publication Date	Title
US4157312A (en)	1979-06-05	Catalytic composite particularly useful for the oxidation of mercaptans contained in a sour petroleum distillate
US4159964A (en)	1979-07-03	Metal chelate catalyst and alkanolamine hydroxide on adsorptive support
US4290913A (en)	1981-09-22	Catalytic composite useful for the treatment of mercaptan-containing sour petroleum distillate
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
EP0394571B1 (fr)	1993-09-01	Utilisation d'une composition catalytique pour l'adoucissement de distillats pétroliers acides
US4908122A (en)	1990-03-13	Process for sweetening a sour hydrocarbon fraction
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
CA1241614A (fr)	1988-09-06	Oxydation catalytique des mercaptans dans les produits de distillation du petrole
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
KR930010567B1 (ko)	1993-10-28	사우어 탄화수소 스트림의 무가성 스위트닝법
US4142964A (en)	1979-03-06	Process for treating a sour petroleum distillate
JPH0334369B2 (fr)	1991-05-22
EP0411762B1 (fr)	1993-09-29	Catalyseur et procédé pour l'adoucissement de charges hydrocarbonées acides
US4293442A (en)	1981-10-06	Catalytic composite, method of manufacture, and process for use
US4206043A (en)	1980-06-03	Conversion of mercaptans contained in a sour petroleum distillate
US4290917A (en)	1981-09-22	Method of manufacturing a catalytic composite
US4276194A (en)	1981-06-30	Catalytic composite, method of manufacture, and process for use
US4308169A (en)	1981-12-29	Method of reactivating a catalytic composite of a carrier material and a mercaptan oxidation catalyst