SE450129B - Forfarande for framstellning av hydrerade kolveten utgaende fran oljeberande skiffer - Google Patents
Forfarande for framstellning av hydrerade kolveten utgaende fran oljeberande skifferInfo
- Publication number
- SE450129B SE450129B SE8102388A SE8102388A SE450129B SE 450129 B SE450129 B SE 450129B SE 8102388 A SE8102388 A SE 8102388A SE 8102388 A SE8102388 A SE 8102388A SE 450129 B SE450129 B SE 450129B
- Authority
- SE
- Sweden
- Prior art keywords
- reagent
- constituents
- oil
- reaction
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 81
- 238000002360 preparation method Methods 0.000 title claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 179
- 238000006243 chemical reaction Methods 0.000 claims description 111
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 87
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 69
- 230000008569 process Effects 0.000 claims description 68
- 229930195733 hydrocarbon Natural products 0.000 claims description 58
- 150000002430 hydrocarbons Chemical class 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 55
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 51
- 239000000470 constituent Substances 0.000 claims description 51
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 45
- 229910052717 sulfur Inorganic materials 0.000 claims description 44
- 239000011593 sulfur Substances 0.000 claims description 44
- 239000004215 Carbon black (E152) Substances 0.000 claims description 40
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 36
- 239000011707 mineral Substances 0.000 claims description 36
- 239000003079 shale oil Substances 0.000 claims description 35
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 27
- 229910021529 ammonia Inorganic materials 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 150000004677 hydrates Chemical class 0.000 claims description 21
- 229910052783 alkali metal Inorganic materials 0.000 claims description 20
- 238000011084 recovery Methods 0.000 claims description 20
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 19
- 150000004763 sulfides Chemical class 0.000 claims description 19
- 229910052700 potassium Inorganic materials 0.000 claims description 18
- 239000011591 potassium Substances 0.000 claims description 18
- 239000007858 starting material Substances 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 16
- 239000004927 clay Substances 0.000 claims description 16
- 150000001340 alkali metals Chemical class 0.000 claims description 15
- 229920001021 polysulfide Polymers 0.000 claims description 14
- 239000003513 alkali Substances 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- -1 alkali metal hydrogen sulphides Chemical class 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 229910052720 vanadium Inorganic materials 0.000 claims description 8
- 238000005984 hydrogenation reaction Methods 0.000 claims description 7
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 7
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 6
- 229910052750 molybdenum Inorganic materials 0.000 claims description 6
- ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 claims description 6
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 5
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 5
- 239000011733 molybdenum Substances 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 239000003447 supported reagent Substances 0.000 claims description 5
- 238000002386 leaching Methods 0.000 claims description 4
- 239000005077 polysulfide Substances 0.000 claims description 4
- 150000008117 polysulfides Polymers 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 claims description 2
- 239000002243 precursor Substances 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 69
- 239000003921 oil Substances 0.000 description 63
- 239000000047 product Substances 0.000 description 45
- 239000007789 gas Substances 0.000 description 35
- 235000010755 mineral Nutrition 0.000 description 33
- 239000000243 solution Substances 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000003054 catalyst Substances 0.000 description 26
- 239000007788 liquid Substances 0.000 description 21
- 239000001257 hydrogen Substances 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 14
- 238000002474 experimental method Methods 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 238000009835 boiling Methods 0.000 description 13
- 229910052708 sodium Inorganic materials 0.000 description 13
- 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 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 238000005755 formation reaction Methods 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 229910052742 iron Inorganic materials 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000004058 oil shale Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000011435 rock Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 229910001385 heavy metal Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229910009112 xH2O Inorganic materials 0.000 description 4
- 230000009471 action Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000010426 asphalt Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000036571 hydration Effects 0.000 description 3
- 238000006703 hydration reaction Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229910052701 rubidium Inorganic materials 0.000 description 3
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- DPCOQCKIZXZTDP-UHFFFAOYSA-N O.[S-2].[K+].[K+] Chemical compound O.[S-2].[K+].[K+] DPCOQCKIZXZTDP-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000000374 eutectic mixture Substances 0.000 description 2
- 238000005189 flocculation Methods 0.000 description 2
- 230000016615 flocculation Effects 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 159000000014 iron salts Chemical class 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 229910052596 spinel Inorganic materials 0.000 description 2
- 239000011029 spinel Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical class [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- QEKFFVMCUJFVOL-UHFFFAOYSA-N O.[S] Chemical class O.[S] QEKFFVMCUJFVOL-UHFFFAOYSA-N 0.000 description 1
- 235000015076 Shorea robusta Nutrition 0.000 description 1
- 244000166071 Shorea robusta Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000689006 Syntrophorhabdaceae Species 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- PFRUBEOIWWEFOL-UHFFFAOYSA-N [N].[S] Chemical compound [N].[S] PFRUBEOIWWEFOL-UHFFFAOYSA-N 0.000 description 1
- 239000012042 active reagent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- CSDREXVUYHZDNP-UHFFFAOYSA-N alumanylidynesilicon Chemical compound [Al].[Si] CSDREXVUYHZDNP-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 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
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- QTNDMWXOEPGHBT-UHFFFAOYSA-N dicesium;sulfide Chemical class [S-2].[Cs+].[Cs+] QTNDMWXOEPGHBT-UHFFFAOYSA-N 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 229910052730 francium Inorganic materials 0.000 description 1
- KLMCZVJOEAUDNE-UHFFFAOYSA-N francium atom Chemical compound [Fr] KLMCZVJOEAUDNE-UHFFFAOYSA-N 0.000 description 1
- 230000005021 gait Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012633 leachable Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- SPEGERVLTUWZPA-UHFFFAOYSA-N n'-[[5-[4,4-bis(ethoxymethyl)cyclohexyl]-1h-pyrazol-4-yl]methyl]-n,n'-dimethylethane-1,2-diamine Chemical compound C1CC(COCC)(COCC)CCC1C1=C(CN(C)CCNC)C=NN1 SPEGERVLTUWZPA-UHFFFAOYSA-N 0.000 description 1
- OUZIIFOEMPAZKX-UHFFFAOYSA-N n-[2-(2-chlorophenyl)sulfanylethyl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]sulfonylpropanamide Chemical compound C=1C=C(C(F)(F)F)C=NC=1S(=O)(=O)C(C)(C)C(=O)NCCSC1=CC=CC=C1Cl OUZIIFOEMPAZKX-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 239000001120 potassium sulphate Substances 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- AHKSSQDILPRNLA-UHFFFAOYSA-N rubidium(1+);sulfide Chemical class [S-2].[Rb+].[Rb+] AHKSSQDILPRNLA-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- KHDSWONFYIAAPE-UHFFFAOYSA-N silicon sulfide Chemical compound S=[Si]=S KHDSWONFYIAAPE-UHFFFAOYSA-N 0.000 description 1
- DHNUAKOQUGJUGA-UHFFFAOYSA-N silicon;sulfane Chemical compound [Si].S DHNUAKOQUGJUGA-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- LPSWFOCTMJQJIS-UHFFFAOYSA-N sulfanium;hydroxide Chemical class [OH-].[SH3+] LPSWFOCTMJQJIS-UHFFFAOYSA-N 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 239000003039 volatile agent 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
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
-
- 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
-
- 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
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
- C10G29/06—Metal salts, or metal salts deposited on a carrier
- C10G29/10—Sulfides
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (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 |
|---|---|---|---|
| US14060480A | 1980-04-15 | 1980-04-15 | |
| US06/220,021 US4366044A (en) | 1979-08-06 | 1981-01-05 | Process for conversion of coal to hydrocarbon and other values |
| US24230581A | 1981-03-20 | 1981-03-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8102388L SE8102388L (sv) | 1981-10-16 |
| SE450129B true SE450129B (sv) | 1987-06-09 |
Family
ID=27385522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8102388A SE450129B (sv) | 1980-04-15 | 1981-04-14 | Forfarande for framstellning av hydrerade kolveten utgaende fran oljeberande skiffer |
Country Status (17)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3303619A1 (de) * | 1983-02-03 | 1984-08-09 | Rollan Dr. 89003 Town of Beatty Nev. Swanson | Verfahren zur gewinnung von kohlenwasserstoffen aus schieferoelgestein |
| FI840787A7 (fi) * | 1983-03-03 | 1984-09-04 | Rollan Swanson | Raskasjuoksuisten raakaöljyn tislausjätteiden, kuten asfalteenien, hartsien tms. pilkkominen ja hydraus. |
| CN1048277C (zh) * | 1994-06-17 | 2000-01-12 | 沈阳市琼江节能技术研究所 | 页岩油加石灰炼制提高油品安定性的方法 |
| US7264711B2 (en) * | 2001-08-17 | 2007-09-04 | Zwick Dwight W | Process for converting oil shale into petroleum |
| CN113415787A (zh) * | 2021-06-29 | 2021-09-21 | 中南大学 | 一种脱硫废液中硫的高效分离提纯的装置和方法 |
| CN113582373A (zh) * | 2021-06-29 | 2021-11-02 | 中南大学 | 一种脱硫废液中硫的低碳分离提纯的装置和方法 |
| US12143081B2 (en) | 2021-08-17 | 2024-11-12 | Bang & Olufsen A/S | Method for increasing perceived loudness of an audio data signal |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB515928A (en) * | 1938-07-11 | 1939-12-18 | Int Hydrogeneeringsoctrooien | Improvements in the production of hydrocarbon products by destructive hydrogenation of solid carbonaceous materials |
| US3354081A (en) * | 1965-09-01 | 1967-11-21 | Exxon Research Engineering Co | Process for desulfurization employing k2s |
| US4119528A (en) * | 1977-08-01 | 1978-10-10 | Exxon Research & Engineering Co. | Hydroconversion of residua with potassium sulfide |
| AU537070B2 (en) * | 1979-08-06 | 1984-06-07 | Swanson, Rollan Dr. | Converting coal to gaseous hydrocarbons and volatile distillates |
-
1981
- 1981-04-14 CH CH248981A patent/CH637688A5/de not_active IP Right Cessation
- 1981-04-14 GR GR64684A patent/GR78337B/el unknown
- 1981-04-14 IL IL62651A patent/IL62651A/xx unknown
- 1981-04-14 DK DK168681A patent/DK168681A/da active IP Right Grant
- 1981-04-14 BR BR8102313A patent/BR8102313A/pt unknown
- 1981-04-14 GB GB8111869A patent/GB2076012B/en not_active Expired
- 1981-04-14 IT IT8148280A patent/IT1148010B/it active
- 1981-04-14 DD DD81229226A patent/DD158232A5/de unknown
- 1981-04-14 FI FI811151A patent/FI73721C/fi not_active IP Right Cessation
- 1981-04-14 FR FR8107478A patent/FR2480299B1/fr not_active Expired
- 1981-04-14 AU AU69521/81A patent/AU538590B2/en not_active Ceased
- 1981-04-14 DE DE19813114987 patent/DE3114987A1/de not_active Withdrawn
- 1981-04-14 SU SU813274749A patent/SU1297734A3/ru active
- 1981-04-14 ES ES501333A patent/ES8203949A1/es not_active Expired
- 1981-04-14 SE SE8102388A patent/SE450129B/sv not_active IP Right Cessation
- 1981-04-14 YU YU976/81A patent/YU41457B/xx unknown
- 1981-04-14 TR TR22287A patent/TR22287A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI73721B (fi) | 1987-07-31 |
| IT8148280A0 (it) | 1981-04-14 |
| AU538590B2 (en) | 1984-08-23 |
| IL62651A (en) | 1985-04-30 |
| ES501333A0 (es) | 1982-04-01 |
| FI811151L (fi) | 1981-10-16 |
| IT1148010B (it) | 1986-11-26 |
| GB2076012A (en) | 1981-11-25 |
| YU41457B (en) | 1987-06-30 |
| CH637688A5 (de) | 1983-08-15 |
| GR78337B (enrdf_load_stackoverflow) | 1984-09-26 |
| IL62651A0 (en) | 1981-06-29 |
| BR8102313A (pt) | 1981-12-08 |
| AU6952181A (en) | 1981-10-22 |
| SE8102388L (sv) | 1981-10-16 |
| DD158232A5 (de) | 1983-01-05 |
| FR2480299B1 (fr) | 1986-06-06 |
| YU97681A (en) | 1983-04-30 |
| DK168681A (da) | 1981-10-16 |
| FI73721C (fi) | 1987-11-09 |
| DE3114987A1 (de) | 1982-04-29 |
| SU1297734A3 (ru) | 1987-03-15 |
| ES8203949A1 (es) | 1982-04-01 |
| FR2480299A1 (fr) | 1981-10-16 |
| GB2076012B (en) | 1983-12-21 |
| TR22287A (tr) | 1986-12-25 |
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| Date | Code | Title | Description |
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| NUG | Patent has lapsed |
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