DE2757476C3 - Katalysator zur Oxidation von Mercaptanen und Mercaptiden - Google Patents
Katalysator zur Oxidation von Mercaptanen und MercaptidenInfo
- Publication number
- DE2757476C3 DE2757476C3 DE2757476A DE2757476A DE2757476C3 DE 2757476 C3 DE2757476 C3 DE 2757476C3 DE 2757476 A DE2757476 A DE 2757476A DE 2757476 A DE2757476 A DE 2757476A DE 2757476 C3 DE2757476 C3 DE 2757476C3
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- mercaptans
- mercaptides
- cobalt
- disulfides
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000003054 catalyst Substances 0.000 title claims description 35
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims description 23
- 230000003647 oxidation Effects 0.000 title claims description 8
- 238000007254 oxidation reaction Methods 0.000 title claims description 8
- 239000012670 alkaline solution Substances 0.000 claims description 24
- 239000010941 cobalt Substances 0.000 claims description 14
- 229910017052 cobalt Inorganic materials 0.000 claims description 14
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 14
- 150000002019 disulfides Chemical class 0.000 claims description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 claims description 6
- 239000011609 ammonium molybdate Substances 0.000 claims description 6
- 235000018660 ammonium molybdate Nutrition 0.000 claims description 6
- 229940010552 ammonium molybdate Drugs 0.000 claims description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 6
- 239000004327 boric acid Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 150000003681 vanadium Chemical class 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 235000010755 mineral Nutrition 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims 3
- 238000001816 cooling Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 34
- 230000002378 acidificating effect Effects 0.000 description 21
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- 239000003513 alkali Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 9
- 239000007800 oxidant agent Substances 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- 230000008929 regeneration Effects 0.000 description 8
- 238000011069 regeneration method Methods 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 150000004696 coordination complex Chemical class 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 5
- 229910052720 vanadium Inorganic materials 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 3
- -1 Are "angry" Chemical compound 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 239000003502 gasoline Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 150000008427 organic disulfides Chemical class 0.000 description 3
- 150000004032 porphyrins Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 229910014033 C-OH Inorganic materials 0.000 description 2
- 229910014570 C—OH Inorganic materials 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-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
- CWSCMEBPTGNWML-UHFFFAOYSA-M [Co]Cl Chemical compound [Co]Cl CWSCMEBPTGNWML-UHFFFAOYSA-M 0.000 description 1
- BIHZVDZSJCVVKP-UHFFFAOYSA-L [Rb+].[OH-].[OH-].[Li+] Chemical compound [Rb+].[OH-].[OH-].[Li+] BIHZVDZSJCVVKP-UHFFFAOYSA-L 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical class N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000007630 basic procedure Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- DIYFKPYLIZNQEX-UHFFFAOYSA-N bis(21,23-dihydroporphyrin-2-yl)diazene Chemical compound C12=C(C=C(N1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2)N=NC1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2 DIYFKPYLIZNQEX-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 150000004700 cobalt complex Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 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
- 239000011261 inert gas Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 229910052815 sulfur oxide Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
- C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/005—Compounds of elements of Group 5 of the Periodic Table without metal-carbon linkages
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Treatment Of Water By Oxidation Or Reduction (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/753,400 US4090954A (en) | 1976-12-22 | 1976-12-22 | Method for oxidizing mercaptans and mercaptide compounds from aqueous alkaline solutions and hydrocarbon distillates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2757476A1 DE2757476A1 (de) | 1978-06-29 |
| DE2757476B2 DE2757476B2 (de) | 1979-12-13 |
| DE2757476C3 true DE2757476C3 (de) | 1980-12-11 |
Family
ID=25030474
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2757476A Expired DE2757476C3 (de) | 1976-12-22 | 1977-12-22 | Katalysator zur Oxidation von Mercaptanen und Mercaptiden |
| DE2759652A Expired DE2759652C3 (de) | 1976-12-22 | 1977-12-22 | Katalysator zur Oxidation von Mercaptanen und Mercaptiden |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2759652A Expired DE2759652C3 (de) | 1976-12-22 | 1977-12-22 | Katalysator zur Oxidation von Mercaptanen und Mercaptiden |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US4090954A (enExample) |
| JP (3) | JPS5379787A (enExample) |
| BE (1) | BE862178A (enExample) |
| BR (1) | BR7708570A (enExample) |
| CA (1) | CA1089449A (enExample) |
| DE (2) | DE2757476C3 (enExample) |
| FR (1) | FR2375201A1 (enExample) |
| GB (1) | GB1559149A (enExample) |
| IT (1) | IT1109487B (enExample) |
| MX (1) | MX4754E (enExample) |
| NL (1) | NL172409C (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4090954A (en) * | 1976-12-22 | 1978-05-23 | Ashland Oil, Inc. | Method for oxidizing mercaptans and mercaptide compounds from aqueous alkaline solutions and hydrocarbon distillates |
| US4277623A (en) * | 1979-08-17 | 1981-07-07 | Phillips Petroleum Company | Conversion of alkane and/or cycloalkane thiols to disulfide with catalyst system comprised of cobalt molybdate and an alkali- or alkaline earth metal hydroxide |
| US4271038A (en) * | 1979-12-17 | 1981-06-02 | Standard Oil Company | Catalysts for the hydroformylation of olefinically unsaturated compounds |
| US4288627A (en) * | 1980-02-12 | 1981-09-08 | Phillips Petroleum Company | Oxidation of thiols employing cobalt molybdate/triethylamine catalyst |
| US4417986A (en) * | 1981-03-13 | 1983-11-29 | Mobil Oil Corporation | Process for reducing the chemical oxygen demand of spent alkaline reagents |
| FR2524818A1 (fr) * | 1982-04-09 | 1983-10-14 | Raffinage Cie Francaise | Nouveau catalyseur d'oxydation de mercaptans en disulfures, son procede de preparation et son application a l'adoucissement des distillats petroliers |
| US4666689A (en) * | 1984-04-26 | 1987-05-19 | Merichem Company | Process for regenerating an alkaline stream containing mercaptan compounds |
| CH658771A5 (de) * | 1984-05-28 | 1986-12-15 | Ciba Geigy Ag | Azaphthalocyanine und deren verwendung als photoaktivatoren. |
| US4753722A (en) * | 1986-06-17 | 1988-06-28 | Merichem Company | Treatment of mercaptan-containing streams utilizing nitrogen based promoters |
| DE3816952A1 (de) * | 1988-05-18 | 1989-11-23 | Inst Kinetika I Kataliz | Katalysator zur oxydation von mercaptanen zu disulfiden und verfahren zu seiner herstellung |
| US4875997A (en) * | 1988-11-17 | 1989-10-24 | Montana Refining Company | Process for treating hydrocarbons containing mercaptans |
| US4956325A (en) * | 1989-03-23 | 1990-09-11 | Merichem Company | Method of impregnating a support material |
| GB9120973D0 (en) * | 1991-10-03 | 1991-11-13 | Dytech Corp Ltd | Desulphurisation treatment |
| CA2120046C (en) * | 1994-01-27 | 1999-09-14 | M-I L.L.C. | Separately removing mercaptans and hydrogen sulfide from gas streams |
| EP0834325B1 (en) * | 1996-10-02 | 2003-07-02 | Orient Chemical Industries, Ltd. | Process for preparing metallophthalocyanine |
| US6387348B1 (en) * | 2000-01-12 | 2002-05-14 | The Boc Group, Inc. | Method for treating spent caustic streams |
| US6696381B2 (en) * | 2000-11-17 | 2004-02-24 | Council Of Scientific & Industrial Research | Process for the preparation of a novel catalyst useful for sweetening of sour petroleum distillates |
| US7005058B1 (en) | 2002-05-08 | 2006-02-28 | Uop Llc | Process and apparatus for removing sulfur from hydrocarbons |
| DE10323839B3 (de) * | 2003-05-23 | 2004-10-21 | Thioplast Chemicals Gmbh & Co.Kg | Oxidation von Mercaptoethanol |
| KR101288128B1 (ko) * | 2006-12-11 | 2013-07-18 | 삼성디스플레이 주식회사 | 금속 프탈로시아닌기를 포함하는 덴드리머 중합체, 그의제조 방법 및 이를 채용한 유기 전계 발광 소자 |
| US8703669B2 (en) * | 2008-03-11 | 2014-04-22 | Afton Chemical Corporation | Ultra-low sulfur clutch-only transmission fluids |
| WO2011114352A2 (en) | 2010-03-17 | 2011-09-22 | Indian Oil Corporation Limited | Process for selective removal of mercaptan from aviation turbine fuel (atf) |
| US8597501B2 (en) | 2010-06-30 | 2013-12-03 | Uop Llc | Process for removing one or more sulfur compounds from a stream |
| US9181498B2 (en) * | 2013-05-29 | 2015-11-10 | Uop Llc | Apparatus and process for removal of sulfur-containing compounds from a hydrocarbon stream |
| US9643146B2 (en) | 2013-11-29 | 2017-05-09 | Uop Llc | Unit for processing a liquid/gas phase mixture, mercaptan oxidation system including the same, and method of processing a liquid/gas phase mixture |
| CA2986599C (en) | 2015-07-08 | 2020-03-24 | Uop Llc | Process for oxidizing one or more thiol compounds |
| WO2017011242A1 (en) | 2015-07-15 | 2017-01-19 | Uop Llc | Oxidation catalyst and processes for using same |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2414374A (en) * | 1943-09-20 | 1947-01-14 | Ici Ltd | Metal phthalocyanines having amino- or nitro-phenyl groups attached to their aromatic nuclei by>o, >co, or>so2 |
| US2988500A (en) * | 1959-03-13 | 1961-06-13 | Universal Oil Prod Co | Treatment of hydrocarbon distillates |
| US3252890A (en) * | 1964-08-28 | 1966-05-24 | Universal Oil Prod Co | Oxidation of mercaptans using phthalocyanine and mercury catalyst |
| US3252892A (en) * | 1964-09-22 | 1966-05-24 | Universal Oil Prod Co | Oxidation of mercapto compounds using corrinoid catalyst |
| US3461139A (en) * | 1967-05-16 | 1969-08-12 | Gulf Research Development Co | Dehydration of benzophenone 3,4,3',4'-tetracarboxylic acid to benzophenone 3,4,3',4'-tetracarboxylic dianhydride |
| US3923645A (en) * | 1973-09-07 | 1975-12-02 | Ashland Oil Inc | Method for oxidizing mercaptans occurring in petroleum refining streams |
| US4028269A (en) * | 1975-08-21 | 1977-06-07 | Uop Inc. | Process for the preparation of a solid bed catalyst system |
| US4090954A (en) * | 1976-12-22 | 1978-05-23 | Ashland Oil, Inc. | Method for oxidizing mercaptans and mercaptide compounds from aqueous alkaline solutions and hydrocarbon distillates |
-
1976
- 1976-12-22 US US05/753,400 patent/US4090954A/en not_active Expired - Lifetime
-
1977
- 1977-09-06 US US05/830,513 patent/US4120865A/en not_active Expired - Lifetime
- 1977-11-28 CA CA291,893A patent/CA1089449A/en not_active Expired
- 1977-12-15 MX MX776717U patent/MX4754E/es unknown
- 1977-12-20 NL NLAANVRAGE7714143,A patent/NL172409C/xx not_active IP Right Cessation
- 1977-12-20 IT IT30998/77A patent/IT1109487B/it active
- 1977-12-21 GB GB53241/77A patent/GB1559149A/en not_active Expired
- 1977-12-22 DE DE2757476A patent/DE2757476C3/de not_active Expired
- 1977-12-22 FR FR7738864A patent/FR2375201A1/fr active Granted
- 1977-12-22 DE DE2759652A patent/DE2759652C3/de not_active Expired
- 1977-12-22 JP JP15368577A patent/JPS5379787A/ja active Granted
- 1977-12-22 BE BE183734A patent/BE862178A/xx unknown
- 1977-12-22 BR BR7708570A patent/BR7708570A/pt not_active IP Right Cessation
-
1980
- 1980-10-17 JP JP55144547A patent/JPS591713B2/ja not_active Expired
- 1980-10-17 JP JP14454880A patent/JPS5681134A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2757476A1 (de) | 1978-06-29 |
| IT1109487B (it) | 1985-12-16 |
| FR2375201B1 (enExample) | 1980-04-04 |
| JPS591713B2 (ja) | 1984-01-13 |
| JPS5681134A (en) | 1981-07-02 |
| DE2757476B2 (de) | 1979-12-13 |
| MX4754E (es) | 1982-09-02 |
| US4090954A (en) | 1978-05-23 |
| NL172409B (nl) | 1983-04-05 |
| US4120865A (en) | 1978-10-17 |
| GB1559149A (en) | 1980-01-16 |
| NL7714143A (nl) | 1978-06-26 |
| FR2375201A1 (fr) | 1978-07-21 |
| JPS5681589A (en) | 1981-07-03 |
| JPS5718936B2 (enExample) | 1982-04-20 |
| BR7708570A (pt) | 1978-08-22 |
| NL172409C (nl) | 1983-09-01 |
| DE2759652B2 (de) | 1981-07-30 |
| BE862178A (fr) | 1978-04-14 |
| JPS5625194B2 (enExample) | 1981-06-10 |
| AU3130677A (en) | 1978-08-24 |
| CA1089449A (en) | 1980-11-11 |
| JPS5379787A (en) | 1978-07-14 |
| DE2759652C3 (de) | 1982-05-13 |
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