BE406156A - - Google Patents
Info
- Publication number
- BE406156A BE406156A BE406156DA BE406156A BE 406156 A BE406156 A BE 406156A BE 406156D A BE406156D A BE 406156DA BE 406156 A BE406156 A BE 406156A
- Authority
- BE
- Belgium
- Prior art keywords
- products
- compounds
- substances
- destructive hydrogenation
- dehydrogenation
- Prior art date
Links
- 239000000047 product Substances 0.000 claims description 214
- 238000005984 hydrogenation reaction Methods 0.000 claims description 203
- 239000000126 substance Substances 0.000 claims description 191
- 230000001066 destructive Effects 0.000 claims description 163
- 150000001875 compounds Chemical class 0.000 claims description 122
- 239000003921 oil Substances 0.000 claims description 117
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 98
- 238000009835 boiling Methods 0.000 claims description 89
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 85
- 239000003054 catalyst Substances 0.000 claims description 83
- 239000001257 hydrogen Substances 0.000 claims description 79
- 229910052739 hydrogen Inorganic materials 0.000 claims description 79
- 238000004821 distillation Methods 0.000 claims description 75
- 238000000034 method Methods 0.000 claims description 74
- 238000006243 chemical reaction Methods 0.000 claims description 69
- 239000000470 constituent Substances 0.000 claims description 57
- 125000003367 polycyclic group Chemical group 0.000 claims description 55
- 239000003245 coal Substances 0.000 claims description 45
- 239000010426 asphalt Substances 0.000 claims description 44
- -1 polycyclic carbon compounds Chemical class 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 36
- 229910052751 metal Inorganic materials 0.000 claims description 34
- 239000002184 metal Substances 0.000 claims description 34
- 238000002425 crystallisation Methods 0.000 claims description 31
- 230000005712 crystallization Effects 0.000 claims description 31
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 28
- 150000002739 metals Chemical class 0.000 claims description 28
- 239000012188 paraffin wax Substances 0.000 claims description 25
- 239000007789 gas Substances 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 21
- 150000002430 hydrocarbons Chemical class 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 239000000295 fuel oil Substances 0.000 claims description 17
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- 150000001722 carbon compounds Chemical class 0.000 claims description 15
- 238000005755 formation reaction Methods 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 15
- 229940108066 Coal Tar Drugs 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 13
- 239000011280 coal tar Substances 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 238000006317 isomerization reaction Methods 0.000 claims description 12
- 230000000737 periodic Effects 0.000 claims description 12
- 239000003463 adsorbent Substances 0.000 claims description 11
- 230000002378 acidificating Effects 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 230000000379 polymerizing Effects 0.000 claims description 8
- 240000004119 Melissa officinalis Species 0.000 claims description 7
- 235000010654 Melissa officinalis Nutrition 0.000 claims description 7
- 239000000865 liniment Substances 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 230000001376 precipitating Effects 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 238000002309 gasification Methods 0.000 claims description 3
- 239000012263 liquid product Substances 0.000 claims description 3
- 230000001264 neutralization Effects 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000004867 fossil resin Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 description 71
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 67
- 239000000203 mixture Substances 0.000 description 48
- BBEAQIROQSPTKN-UHFFFAOYSA-N Pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 36
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 36
- 150000001923 cyclic compounds Chemical class 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 238000011084 recovery Methods 0.000 description 30
- 239000011269 tar Substances 0.000 description 30
- 229910052500 inorganic mineral Inorganic materials 0.000 description 28
- 235000010755 mineral Nutrition 0.000 description 28
- 239000011707 mineral Substances 0.000 description 28
- 238000000926 separation method Methods 0.000 description 25
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 23
- 229910052753 mercury Inorganic materials 0.000 description 23
- 229910052799 carbon Inorganic materials 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- MWPLVEDNUUSJAV-UHFFFAOYSA-N Anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 21
- 235000019809 paraffin wax Nutrition 0.000 description 19
- 235000019271 petrolatum Nutrition 0.000 description 19
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 229920005989 resin Polymers 0.000 description 18
- WDECIBYCCFPHNR-UHFFFAOYSA-N Chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 17
- 239000007795 chemical reaction product Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 238000001556 precipitation Methods 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 14
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 14
- 150000001491 aromatic compounds Chemical class 0.000 description 14
- QGJOPFRUJISHPQ-UHFFFAOYSA-N carbon bisulphide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 14
- 238000007670 refining Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- ZOKXTWBITQBERF-UHFFFAOYSA-N molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 12
- 229910052750 molybdenum Inorganic materials 0.000 description 12
- 239000011733 molybdenum Substances 0.000 description 12
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 238000001311 chemical methods and process Methods 0.000 description 11
- 230000000875 corresponding Effects 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 11
- 239000003077 lignite Substances 0.000 description 11
- 150000004763 sulfides Chemical class 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000001914 filtration Methods 0.000 description 10
- 238000005194 fractionation Methods 0.000 description 10
- 230000036961 partial Effects 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N Fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 9
- 239000003502 gasoline Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 9
- 229910052721 tungsten Inorganic materials 0.000 description 9
- 239000010937 tungsten Substances 0.000 description 9
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- JEIPFZHSYJVQDO-UHFFFAOYSA-N Iron(III) oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 8
- 210000004940 Nucleus Anatomy 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000000571 coke Substances 0.000 description 8
- 238000004508 fractional distillation Methods 0.000 description 8
- 229910000460 iron oxide Inorganic materials 0.000 description 8
- 239000002480 mineral oil Substances 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- 230000002829 reduced Effects 0.000 description 8
- GBROPGWFBFCKAG-UHFFFAOYSA-N Picene Chemical compound C1=CC2=C3C=CC=CC3=CC=C2C2=C1C1=CC=CC=C1C=C2 GBROPGWFBFCKAG-UHFFFAOYSA-N 0.000 description 7
- 238000007792 addition Methods 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000003610 charcoal Substances 0.000 description 7
- 229910052804 chromium Inorganic materials 0.000 description 7
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 7
- 239000011651 chromium Substances 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- 238000001640 fractional crystallisation Methods 0.000 description 7
- 229910052742 iron Inorganic materials 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 238000005292 vacuum distillation Methods 0.000 description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
- 229910052725 zinc Inorganic materials 0.000 description 7
- 239000011701 zinc Substances 0.000 description 7
- 229960000583 Acetic Acid Drugs 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N al2o3 Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 239000010687 lubricating oil Substances 0.000 description 6
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 229910052759 nickel Inorganic materials 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- PTISTKLWEJDJID-UHFFFAOYSA-N sulfanylidenemolybdenum Chemical compound [Mo]=S PTISTKLWEJDJID-UHFFFAOYSA-N 0.000 description 6
- WWNBZGLDODTKEM-UHFFFAOYSA-N sulfanylidenenickel Chemical compound [Ni]=S WWNBZGLDODTKEM-UHFFFAOYSA-N 0.000 description 6
- 238000006277 sulfonation reaction Methods 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 229910052720 vanadium Inorganic materials 0.000 description 6
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium(0) Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- CWRYPZZKDGJXCA-UHFFFAOYSA-N Acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 5
- QGAVSDVURUSLQK-UHFFFAOYSA-N Ammonium heptamolybdate Chemical compound N.N.N.N.N.N.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.[Mo].[Mo].[Mo].[Mo].[Mo].[Mo].[Mo] QGAVSDVURUSLQK-UHFFFAOYSA-N 0.000 description 5
- 239000011609 ammonium molybdate Substances 0.000 description 5
- 235000018660 ammonium molybdate Nutrition 0.000 description 5
- 229940010552 ammonium molybdate Drugs 0.000 description 5
- 230000003197 catalytic Effects 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 235000011118 potassium hydroxide Nutrition 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 235000015096 spirit Nutrition 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000011135 tin Substances 0.000 description 5
- 229910052718 tin Inorganic materials 0.000 description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
- 230000001131 transforming Effects 0.000 description 5
- 239000011592 zinc chloride Substances 0.000 description 5
- 235000005074 zinc chloride Nutrition 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N Boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N Methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000003518 caustics Substances 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 238000005336 cracking Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 230000004927 fusion Effects 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000011133 lead Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- PWHULOQIROXLJO-UHFFFAOYSA-N manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 4
- 229910052748 manganese Inorganic materials 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
- 150000002736 metal compounds Chemical class 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical class [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 4
- 230000001603 reducing Effects 0.000 description 4
- 238000005057 refrigeration Methods 0.000 description 4
- 239000012261 resinous substance Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-Methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 3
- GKEUODMJRFDLJY-UHFFFAOYSA-N 1-methyl-9H-fluorene Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2C GKEUODMJRFDLJY-UHFFFAOYSA-N 0.000 description 3
- RSWGJHLUYNHPMX-ONCXSQPRSA-N Abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 3
- RSWGJHLUYNHPMX-HNBVOPMISA-N Abietic acid Natural products C([C@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-HNBVOPMISA-N 0.000 description 3
- TXCDCPKCNAJMEE-UHFFFAOYSA-N Dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 3
- NMCUIPGRVMDVDB-UHFFFAOYSA-L Iron(II) chloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 3
- OXNIZHLAWKMVMX-UHFFFAOYSA-N Picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 3
- NXLOLUFNDSBYTP-UHFFFAOYSA-N Retene Chemical compound C1=CC=C2C3=CC=C(C(C)C)C=C3C=CC2=C1C NXLOLUFNDSBYTP-UHFFFAOYSA-N 0.000 description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J Titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000003575 carbonaceous material Substances 0.000 description 3
- 238000004939 coking Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 150000002605 large molecules Chemical class 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- 239000003415 peat Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229940114148 picric acid Drugs 0.000 description 3
- 239000011295 pitch Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- XCUPBHGRVHYPQC-UHFFFAOYSA-N sulfanylidenetungsten Chemical compound [W]=S XCUPBHGRVHYPQC-UHFFFAOYSA-N 0.000 description 3
- 229950002929 trinitrophenol Drugs 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- AEFBNJXWRHSZGO-UHFFFAOYSA-N 1,2,3,3a,4,5-hexahydropyrene Chemical compound C1=C2CCCC(CC3)C2=C2C3=CC=CC2=C1 AEFBNJXWRHSZGO-UHFFFAOYSA-N 0.000 description 2
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Landscapes
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE406156A true BE406156A (ko) |
Family
ID=71211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE406156D BE406156A (ko) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE406156A (ko) |
-
0
- BE BE406156D patent/BE406156A/fr unknown
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