CA2781414A1 - Hydrogenation de matieres carbonees solides a l'aide de catalyseurs mixtes - Google Patents
Hydrogenation de matieres carbonees solides a l'aide de catalyseurs mixtes Download PDFInfo
- Publication number
- CA2781414A1 CA2781414A1 CA2781414A CA2781414A CA2781414A1 CA 2781414 A1 CA2781414 A1 CA 2781414A1 CA 2781414 A CA2781414 A CA 2781414A CA 2781414 A CA2781414 A CA 2781414A CA 2781414 A1 CA2781414 A1 CA 2781414A1
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- carbonaceous material
- titanium
- metal
- coal
- 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.)
- Abandoned
Links
- 239000003575 carbonaceous material Substances 0.000 title claims abstract description 173
- 239000007787 solid Substances 0.000 title claims abstract description 71
- 239000003054 catalyst Substances 0.000 title claims description 173
- 238000005984 hydrogenation reaction Methods 0.000 title description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 93
- 239000002184 metal Substances 0.000 claims abstract description 93
- 238000000034 method Methods 0.000 claims abstract description 85
- 239000010936 titanium Substances 0.000 claims abstract description 78
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 73
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 70
- 238000006243 chemical reaction Methods 0.000 claims abstract description 68
- 239000012263 liquid product Substances 0.000 claims abstract description 27
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 114
- 239000000203 mixture Substances 0.000 claims description 111
- 239000003245 coal Substances 0.000 claims description 95
- 239000007788 liquid Substances 0.000 claims description 65
- 229910052742 iron Inorganic materials 0.000 claims description 58
- 239000002245 particle Substances 0.000 claims description 58
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 41
- 229910052717 sulfur Inorganic materials 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
- 239000011593 sulfur Substances 0.000 claims description 34
- 239000007789 gas Substances 0.000 claims description 27
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 25
- 239000004094 surface-active agent Substances 0.000 claims description 17
- 239000011701 zinc Substances 0.000 claims description 17
- 229910052725 zinc Inorganic materials 0.000 claims description 15
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052759 nickel Inorganic materials 0.000 claims description 13
- 229910052750 molybdenum Inorganic materials 0.000 claims description 10
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 9
- 239000011733 molybdenum Substances 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 8
- 229910052721 tungsten Inorganic materials 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 6
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 6
- 239000010937 tungsten Substances 0.000 claims description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
- 239000011651 chromium Substances 0.000 claims description 5
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- 239000010941 cobalt Substances 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000011135 tin Substances 0.000 claims description 5
- 229910052718 tin Inorganic materials 0.000 claims description 5
- 229910052720 vanadium Inorganic materials 0.000 claims description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052804 chromium Inorganic materials 0.000 claims description 4
- 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 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- 239000012018 catalyst precursor Substances 0.000 description 104
- 239000000463 material Substances 0.000 description 45
- -1 e.g. Substances 0.000 description 35
- 239000002904 solvent Substances 0.000 description 26
- 230000003197 catalytic effect Effects 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 21
- 238000010438 heat treatment Methods 0.000 description 20
- 239000011230 binding agent Substances 0.000 description 19
- 239000002002 slurry Substances 0.000 description 19
- 239000003921 oil Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 150000003464 sulfur compounds Chemical class 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 13
- 239000000654 additive Substances 0.000 description 13
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 13
- 239000002956 ash Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000000926 separation method Methods 0.000 description 12
- 150000002739 metals Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 8
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- QDZRBIRIPNZRSG-UHFFFAOYSA-N titanium nitrate Chemical compound [O-][N+](=O)O[Ti](O[N+]([O-])=O)(O[N+]([O-])=O)O[N+]([O-])=O QDZRBIRIPNZRSG-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 239000012990 dithiocarbamate Substances 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 7
- 238000011068 loading method Methods 0.000 description 7
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 6
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 6
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 6
- 239000005077 polysulfide Substances 0.000 description 6
- 229920001021 polysulfide Polymers 0.000 description 6
- 150000008117 polysulfides Polymers 0.000 description 6
- 239000010734 process oil Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 5
- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 5
- 229910052747 lanthanoid Inorganic materials 0.000 description 5
- 150000002602 lanthanoids Chemical class 0.000 description 5
- DCKVFVYPWDKYDN-UHFFFAOYSA-L oxygen(2-);titanium(4+);sulfate Chemical compound [O-2].[Ti+4].[O-]S([O-])(=O)=O DCKVFVYPWDKYDN-UHFFFAOYSA-L 0.000 description 5
- 230000000737 periodic effect Effects 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 5
- 229910000348 titanium sulfate Inorganic materials 0.000 description 5
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- INNSZZHSFSFSGS-UHFFFAOYSA-N acetic acid;titanium Chemical compound [Ti].CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O INNSZZHSFSFSGS-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 4
- 238000004231 fluid catalytic cracking Methods 0.000 description 4
- 239000000852 hydrogen donor Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 4
- 239000006259 organic additive Substances 0.000 description 4
- 150000002902 organometallic compounds Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229910052684 Cerium Inorganic materials 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 229910003092 TiS2 Inorganic materials 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 3
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- 150000003608 titanium Chemical class 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000003775 Density Functional Theory Methods 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 229910000608 Fe(NO3)3.9H2O Inorganic materials 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- XYXNTHIYBIDHGM-UHFFFAOYSA-N ammonium thiosulfate Chemical compound [NH4+].[NH4+].[O-]S([O-])(=O)=S XYXNTHIYBIDHGM-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 150000001860 citric acid derivatives Chemical class 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000003034 coal gas Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- ZKKLPDLKUGTPME-UHFFFAOYSA-N diazanium;bis(sulfanylidene)molybdenum;sulfanide Chemical compound [NH4+].[NH4+].[SH-].[SH-].S=[Mo]=S ZKKLPDLKUGTPME-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 229960001484 edetic acid Drugs 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000002149 energy-dispersive X-ray emission spectroscopy Methods 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 159000000014 iron salts Chemical class 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 2
- 229910052961 molybdenite Inorganic materials 0.000 description 2
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 2
- LFQXBAMBISRCSO-UHFFFAOYSA-J n,n-diethylcarbamodithioate;titanium(4+) Chemical compound [Ti+4].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S.CCN(CC)C([S-])=S.CCN(CC)C([S-])=S LFQXBAMBISRCSO-UHFFFAOYSA-J 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
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- GLFDLEXFOHUASB-UHFFFAOYSA-N trimethyl(tetradecyl)azanium Chemical compound CCCCCCCCCCCCCC[N+](C)(C)C GLFDLEXFOHUASB-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002888 zwitterionic surfactant 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
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/08—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal with moving catalysts
- C10G1/086—Characterised by the catalyst used
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/625,411 | 2009-11-24 | ||
| US12/625,411 US20110120917A1 (en) | 2009-11-24 | 2009-11-24 | Hydrogenation of solid carbonaceous materials using mixed catalysts |
| PCT/US2010/057740 WO2011066253A2 (fr) | 2009-11-24 | 2010-11-23 | Hydrogénation de matières carbonées solides à l'aide de catalyseurs mixtes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2781414A1 true CA2781414A1 (fr) | 2011-06-03 |
Family
ID=44061317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2781414A Abandoned CA2781414A1 (fr) | 2009-11-24 | 2010-11-23 | Hydrogenation de matieres carbonees solides a l'aide de catalyseurs mixtes |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20110120917A1 (fr) |
| CN (1) | CN102666791B (fr) |
| CA (1) | CA2781414A1 (fr) |
| WO (2) | WO2011066259A2 (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113528146B (zh) * | 2021-08-19 | 2022-01-28 | 河南大学 | 一种表面改性掺杂二氧化硅的硫化亚铁土壤重金属钝化剂的制备和应用 |
Family Cites Families (76)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3223698A (en) * | 1961-01-09 | 1965-12-14 | Inst Noguchi | Method for liquefying lignin |
| US3645665A (en) * | 1969-05-26 | 1972-02-29 | Dan River Inc | Dyeing cellulosic textiles with vat and sulfur dyes using sodium dithionite and an aldehyde-bisulfite addition product stabilizer |
| GB1481689A (en) * | 1973-11-08 | 1977-08-03 | Coal Ind | Hydrogenation of coal |
| SE394191B (sv) * | 1975-10-07 | 1977-06-13 | Anderson Ind Ab Paul | Sett vid lagring av for overforing av stora krafter avsedda anordningar samt anordning for settets genomforande |
| AU506174B2 (en) * | 1976-05-28 | 1979-12-13 | Kobe Steel Limited | Coal liquefaction |
| US4077867A (en) * | 1976-07-02 | 1978-03-07 | Exxon Research & Engineering Co. | Hydroconversion of coal in a hydrogen donor solvent with an oil-soluble catalyst |
| US4080282A (en) * | 1976-07-12 | 1978-03-21 | Gulf Research & Development Company | Catalytic reactor and process for hydrogenating solid-containing carbonaceous materials in said reactor |
| US4081361A (en) * | 1976-07-26 | 1978-03-28 | Gulf Research & Development Company | Process for the conversion of carbonaceous materials |
| US4190518A (en) * | 1977-12-29 | 1980-02-26 | Gulf Research And Development Company | Solvent refined coal process |
| US4323447A (en) * | 1980-02-05 | 1982-04-06 | Gulf Research & Development Company | Coal Liquefaction process employing octahydrophenanthrene-enriched solvent |
| US4369106A (en) * | 1980-04-10 | 1983-01-18 | Exxon Research And Engineering Co. | Coal liquefaction process |
| US4450066A (en) * | 1980-09-02 | 1984-05-22 | Exxon Research And Engineering Co. | Hydrothermal pretreatment to prevent scale during liquefaction of certain solid carbonaceous materials |
| JPS5761082A (en) * | 1980-09-30 | 1982-04-13 | Kobe Steel Ltd | Liquefaction of coal |
| US4485008A (en) * | 1980-12-05 | 1984-11-27 | Exxon Research And Engineering Co. | Liquefaction process |
| US4417972A (en) * | 1981-11-04 | 1983-11-29 | Exxon Research And Engineering Co. | Recovery of coal liquefaction catalysts |
| US4401549A (en) * | 1981-11-17 | 1983-08-30 | Uop Inc. | Liquefaction of calcium-containing coals |
| US4401550A (en) * | 1982-01-11 | 1983-08-30 | Uop Inc. | Liquefaction of calcium-containing coals |
| US4485006A (en) * | 1982-03-04 | 1984-11-27 | Exxon Research And Engineering Co. | Start-up method for a hydrorefining process |
| US4434043A (en) * | 1982-06-01 | 1984-02-28 | Exxon Research And Engineering Co. | Recovery of catalyst from coal liquefaction residues |
| US4578176A (en) * | 1982-06-09 | 1986-03-25 | Institute Of Gas Technology | Fuel production by free fall countercurrent flow |
| JPS59109588A (ja) * | 1982-12-15 | 1984-06-25 | Kobe Steel Ltd | 褐炭の液化方法 |
| IT1163480B (it) * | 1983-06-08 | 1987-04-08 | Anic Spa | Procedimento a piu' stadi per la liquefazione diretta del carbone |
| US5094991A (en) * | 1983-08-29 | 1992-03-10 | Chevron Research Company | Slurry catalyst for hydroprocessing heavy and refractory oils |
| US5484755A (en) * | 1983-08-29 | 1996-01-16 | Lopez; Jaime | Process for preparing a dispersed Group VIB metal sulfide catalyst |
| US4493761A (en) * | 1983-12-05 | 1985-01-15 | Standard Oil Company (Indiana) | Catalytic hydroliquefaction using a Cr-Mo-Group VIII catalyst |
| US4917791A (en) * | 1984-06-01 | 1990-04-17 | Kang Chia Chen Chu | Process and catalysts for hydroconversion of coal or petroleum asphaltene to distillate liquids |
| US4617105A (en) * | 1985-09-26 | 1986-10-14 | Air Products And Chemicals, Inc. | Coal liquefaction process using pretreatment with a binary solvent mixture |
| US5236881A (en) * | 1986-08-22 | 1993-08-17 | Coal Industry (Patents) Limited | Coal extract hydrocracking catalyst |
| USH669H (en) * | 1986-12-08 | 1989-09-05 | The United States Of America As Represented By The United States Department Of Energy | Samarium-145 and its use as a radiation source |
| US4824558A (en) * | 1987-09-04 | 1989-04-25 | Exxon Research And Engineering Company | Coal liquefaction process with metal/iodine cocatalyst |
| US4831003A (en) * | 1987-09-14 | 1989-05-16 | Exxon Research And Engineering Company | Catalyst composition and process of making |
| US5051389A (en) * | 1987-09-16 | 1991-09-24 | Exxon Research And Engineering Company | Catalyst composition prepared by vapor depositing onto a carbon support |
| US4948523A (en) * | 1987-09-30 | 1990-08-14 | Amoco Corporation | Chlorine-free silver protective lubricant composition (I) |
| US4816141A (en) * | 1987-10-16 | 1989-03-28 | Hri, Inc. | Catalytic two-stage liquefaction of coal utilizing cascading of used ebullated-bed catalyst |
| CA1317585C (fr) * | 1988-02-02 | 1993-05-11 | Chandra Prakash Khulbe | Procede d'hydrocraquage de produits petroliers lourds, en presence de bouillie de fer-charbon |
| US5070064A (en) * | 1989-08-07 | 1991-12-03 | Exxon Research And Engineering Company | Catalyst pretreatment method |
| US5151173A (en) * | 1989-12-21 | 1992-09-29 | Exxon Research And Engineering Company | Conversion of coal with promoted carbon monoxide pretreatment |
| US5183561A (en) * | 1990-01-25 | 1993-02-02 | Mobil Oil Corp. | Demetallation of hydrocarbon feedstocks with a synthetic mesoporous crystalline material |
| US5015366A (en) * | 1990-04-10 | 1991-05-14 | The United States Of America As Represented By The United States Department Of Energy | Process and apparatus for coal hydrogenation |
| US5039392A (en) * | 1990-06-04 | 1991-08-13 | Exxon Research And Engineering Company | Hydroconversion process using a sulfided molybdenum catalyst concentrate |
| US5200063A (en) * | 1990-06-21 | 1993-04-06 | Exxon Research And Engineering Company | Coal hydroconversion process comprising solvent enhanced pretreatment with carbon monoxide |
| JP2529031B2 (ja) * | 1991-01-30 | 1996-08-28 | 株式会社芝浦製作所 | スパッタリング装置 |
| US5246570A (en) * | 1992-04-09 | 1993-09-21 | Amoco Corporation | Coal liquefaction process using soluble molybdenum-containing organophosphorodithioate catalyst |
| US5783065A (en) * | 1992-09-03 | 1998-07-21 | University Of Utah Research Foundation | Method for coal liquefaction |
| US5338441A (en) * | 1992-10-13 | 1994-08-16 | Exxon Research And Engineering Company | Liquefaction process |
| US5454934A (en) * | 1992-12-23 | 1995-10-03 | Exxon Research & Engineering Co. | Coal liquefaction using atomically dispersed metals |
| US5344553A (en) * | 1993-02-22 | 1994-09-06 | Mobil Oil Corporation | Upgrading of a hydrocarbon feedstock utilizing a graded, mesoporous catalyst system |
| US5389230A (en) * | 1993-06-11 | 1995-02-14 | Exxon Research & Engineering Co. | Catalytic hydroconversion process |
| US5332489A (en) * | 1993-06-11 | 1994-07-26 | Exxon Research & Engineering Co. | Hydroconversion process for a carbonaceous material |
| US5489375A (en) * | 1994-06-08 | 1996-02-06 | Amoco Corporation | Resid hydroprocessing method |
| US5573556A (en) * | 1994-11-03 | 1996-11-12 | Exxon Research And Engineering Company | Conversion of solid carbonaceous material using polyoxoanions |
| US5620591A (en) * | 1994-12-22 | 1997-04-15 | Exxon Research & Engineering Company | Hydroconversion process with plug-flow molybdenum catalyst concentrate preparation |
| US6054043A (en) * | 1995-03-28 | 2000-04-25 | Simpson; Theodore B. | Process for the hydrogenation of hydro-carbonaceous materials (Carb-Mat) for the production of vaporizable products |
| US6139723A (en) * | 1996-02-23 | 2000-10-31 | Hydrocarbon Technologies, Inc. | Iron-based ionic liquid catalysts for hydroprocessing carbonaceous feeds |
| US6190542B1 (en) * | 1996-02-23 | 2001-02-20 | Hydrocarbon Technologies, Inc. | Catalytic multi-stage process for hydroconversion and refining hydrocarbon feeds |
| JP3715729B2 (ja) * | 1996-10-21 | 2005-11-16 | 株式会社神戸製鋼所 | 石炭の液化方法 |
| US5728656A (en) * | 1997-03-20 | 1998-03-17 | Chevron Chemical Company | Lower-ash lubricating oil having ultra-neutral zinc dialkyldithiophosphates |
| US5744026A (en) * | 1997-04-10 | 1998-04-28 | Eastman Chemical Company | Catalyst system and process for benzyl ether fragmentation and coal liquefaction |
| US6153155A (en) * | 1997-12-31 | 2000-11-28 | Exxon Research And Engineering Company | Recovery of the transition metal component of catalyst used in heavy feed hydroconversion |
| JP3679643B2 (ja) * | 1999-02-26 | 2005-08-03 | 三洋電機株式会社 | ディスク記録装置 |
| US7095708B1 (en) * | 1999-06-23 | 2006-08-22 | Cingular Wireless Ii, Llc | Methods and apparatus for use in communicating voice and high speed data in a wireless communication system |
| JP2001026785A (ja) * | 1999-07-15 | 2001-01-30 | Agency Of Ind Science & Technol | 石炭液化方法 |
| US6153156A (en) * | 1999-08-02 | 2000-11-28 | Gnb Technologies, Inc. | Method for purifying leady oxides |
| US6551965B2 (en) * | 2000-02-14 | 2003-04-22 | Chevron Oronite Company Llc | Marine diesel engine lubricating oil composition having improved high temperature performance |
| GB0011115D0 (en) * | 2000-05-09 | 2000-06-28 | Infineum Int Ltd | Lubricating oil compositions |
| US6569818B2 (en) * | 2000-06-02 | 2003-05-27 | Chevron Oronite Company, Llc | Lubricating oil composition |
| JP4018328B2 (ja) * | 2000-09-28 | 2007-12-05 | 新日本石油株式会社 | 潤滑油組成物 |
| ITMI20030992A1 (it) * | 2003-05-20 | 2004-11-21 | Solvay Solexis Spa | Additivi perfluoropolieterei. |
| US7163911B2 (en) * | 2003-05-22 | 2007-01-16 | Chevron Oronite Company Llc | Carboxylated detergent-dispersant additive for lubricating oils |
| US20050043191A1 (en) * | 2003-08-22 | 2005-02-24 | Farng L. Oscar | High performance non-zinc, zero phosphorus engine oils for internal combustion engines |
| ITMI20032207A1 (it) * | 2003-11-14 | 2005-05-15 | Enitecnologie Spa | Procedimento integrato per la conversione di cariche contenenti carbone in prodotti liquidi. |
| US8030258B2 (en) * | 2005-07-29 | 2011-10-04 | Chevron Oronite Company Llc | Overbased alkaline earth metal alkylhydroxybenzoates having low crude sediment |
| JP3920304B1 (ja) * | 2005-11-22 | 2007-05-30 | 株式会社神戸製鋼所 | 低品位炭を原料とする固形燃料の製造方法および製造装置 |
| CN101280207B (zh) * | 2007-04-04 | 2011-04-20 | 中国石油化工股份有限公司 | 一种低质煤直接液化和综合利用方法 |
| US9074154B2 (en) * | 2008-02-13 | 2015-07-07 | Hydrocoal Technologies, Llc | Process for improved liquefaction of fuel solids |
| US8123934B2 (en) * | 2008-06-18 | 2012-02-28 | Chevron U.S.A., Inc. | System and method for pretreatment of solid carbonaceous material |
-
2009
- 2009-11-24 US US12/625,411 patent/US20110120917A1/en not_active Abandoned
-
2010
- 2010-11-23 WO PCT/US2010/057751 patent/WO2011066259A2/fr not_active Ceased
- 2010-11-23 CN CN201080053081.1A patent/CN102666791B/zh not_active Expired - Fee Related
- 2010-11-23 CA CA2781414A patent/CA2781414A1/fr not_active Abandoned
- 2010-11-23 WO PCT/US2010/057740 patent/WO2011066253A2/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US20110120917A1 (en) | 2011-05-26 |
| WO2011066253A3 (fr) | 2011-10-20 |
| WO2011066259A2 (fr) | 2011-06-03 |
| CN102666791B (zh) | 2015-04-01 |
| WO2011066259A3 (fr) | 2011-07-28 |
| WO2011066253A2 (fr) | 2011-06-03 |
| CN102666791A (zh) | 2012-09-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20161123 |