KR102048250B1 - 알킬 방향족 탄화수소의 분리방법 및 분리장치 - Google Patents
알킬 방향족 탄화수소의 분리방법 및 분리장치 Download PDFInfo
- Publication number
- KR102048250B1 KR102048250B1 KR1020147036424A KR20147036424A KR102048250B1 KR 102048250 B1 KR102048250 B1 KR 102048250B1 KR 1020147036424 A KR1020147036424 A KR 1020147036424A KR 20147036424 A KR20147036424 A KR 20147036424A KR 102048250 B1 KR102048250 B1 KR 102048250B1
- Authority
- KR
- South Korea
- Prior art keywords
- complex
- alkyl aromatic
- aromatic hydrocarbon
- acid
- diluent
- 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.)
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- -1 alkyl aromatic hydrocarbon Chemical class 0.000 title claims abstract description 169
- 238000000034 method Methods 0.000 title claims abstract description 89
- 239000003930 superacid Substances 0.000 claims abstract description 159
- 239000003085 diluting agent Substances 0.000 claims abstract description 114
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 107
- 239000000203 mixture Substances 0.000 claims abstract description 103
- 238000003795 desorption Methods 0.000 claims abstract description 75
- 230000002378 acidificating effect Effects 0.000 claims abstract description 43
- 239000000284 extract Substances 0.000 claims abstract description 14
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 282
- 238000000605 extraction Methods 0.000 claims description 127
- 239000000243 solution Substances 0.000 claims description 86
- 239000002253 acid Substances 0.000 claims description 68
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 66
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 62
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 58
- 239000002841 Lewis acid Substances 0.000 claims description 41
- 238000000926 separation method Methods 0.000 claims description 37
- 150000007517 lewis acids Chemical class 0.000 claims description 35
- 239000007788 liquid Substances 0.000 claims description 35
- 229910015900 BF3 Inorganic materials 0.000 claims description 32
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 29
- 238000004821 distillation Methods 0.000 claims description 25
- 239000007848 Bronsted acid Substances 0.000 claims description 20
- 238000009835 boiling Methods 0.000 claims description 19
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 11
- 238000007599 discharging Methods 0.000 claims description 9
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 8
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 claims description 8
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 claims description 8
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 claims description 8
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- YRGLXIVYESZPLQ-UHFFFAOYSA-I tantalum pentafluoride Chemical compound F[Ta](F)(F)(F)F YRGLXIVYESZPLQ-UHFFFAOYSA-I 0.000 claims description 5
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 4
- AOLPZAHRYHXPLR-UHFFFAOYSA-I pentafluoroniobium Chemical compound F[Nb](F)(F)(F)F AOLPZAHRYHXPLR-UHFFFAOYSA-I 0.000 claims description 4
- LPSXSORODABQKT-UHFFFAOYSA-N tetrahydrodicyclopentadiene Chemical compound C1C2CCC1C1C2CCC1 LPSXSORODABQKT-UHFFFAOYSA-N 0.000 claims description 4
- XROWMBWRMNHXMF-UHFFFAOYSA-J titanium tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Ti+4] XROWMBWRMNHXMF-UHFFFAOYSA-J 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 3
- NXHILIPIEUBEPD-UHFFFAOYSA-H tungsten hexafluoride Chemical compound F[W](F)(F)(F)(F)F NXHILIPIEUBEPD-UHFFFAOYSA-H 0.000 claims description 3
- GUNJVIDCYZYFGV-UHFFFAOYSA-K antimony trifluoride Chemical compound F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 claims description 2
- VVRKSAMWBNJDTH-UHFFFAOYSA-N difluorophosphane Chemical compound FPF VVRKSAMWBNJDTH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 claims description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 64
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
- 239000002585 base Substances 0.000 description 40
- 239000008096 xylene Substances 0.000 description 35
- AFZZYIJIWUTJFO-UHFFFAOYSA-N 1,3-diethylbenzene Chemical compound CCC1=CC=CC(CC)=C1 AFZZYIJIWUTJFO-UHFFFAOYSA-N 0.000 description 32
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 32
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 32
- ZLCSFXXPPANWQY-UHFFFAOYSA-N 3-ethyltoluene Chemical compound CCC1=CC=CC(C)=C1 ZLCSFXXPPANWQY-UHFFFAOYSA-N 0.000 description 30
- 239000012071 phase Substances 0.000 description 25
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical class CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000003921 oil Substances 0.000 description 22
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 20
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical class CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 15
- 238000000354 decomposition reaction Methods 0.000 description 15
- 229940078552 o-xylene Drugs 0.000 description 15
- 239000002994 raw material Substances 0.000 description 15
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 7
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
- 238000007323 disproportionation reaction Methods 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical compound CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- FZDZWLDRELLWNN-UHFFFAOYSA-N 1,2,3,3a,4,5,5a,6,7,8,8a,8b-dodecahydroacenaphthylene Chemical compound C1CCC2CCC3C2C1CCC3 FZDZWLDRELLWNN-UHFFFAOYSA-N 0.000 description 4
- WJYMPXJVHNDZHD-UHFFFAOYSA-N 1,3,5-triethylbenzene Chemical compound CCC1=CC(CC)=CC(CC)=C1 WJYMPXJVHNDZHD-UHFFFAOYSA-N 0.000 description 4
- ZLGPNBBJPOBSLY-UHFFFAOYSA-N 2-fluoro-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(F)C(C)=C1 ZLGPNBBJPOBSLY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000003463 adsorbent Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CWNOIUTVJRWADX-UHFFFAOYSA-N 1,3-dimethyladamantane Chemical compound C1C(C2)CC3CC1(C)CC2(C)C3 CWNOIUTVJRWADX-UHFFFAOYSA-N 0.000 description 3
- CWLKTJOTWITYSI-UHFFFAOYSA-N 1-fluoronaphthalene Chemical compound C1=CC=C2C(F)=CC=CC2=C1 CWLKTJOTWITYSI-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- KVZJLSYJROEPSQ-OCAPTIKFSA-N cis-1,2-dimethylcyclohexane Chemical compound C[C@H]1CCCC[C@H]1C KVZJLSYJROEPSQ-OCAPTIKFSA-N 0.000 description 3
- KVZJLSYJROEPSQ-UHFFFAOYSA-N cis-DMCH Natural products CC1CCCCC1C KVZJLSYJROEPSQ-UHFFFAOYSA-N 0.000 description 3
- NNBZCPXTIHJBJL-AOOOYVTPSA-N cis-decalin Chemical compound C1CCC[C@H]2CCCC[C@H]21 NNBZCPXTIHJBJL-AOOOYVTPSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical group CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- NPDIDUXTRAITDE-UHFFFAOYSA-N 1-methyl-3-phenylbenzene Chemical group CC1=CC=CC(C=2C=CC=CC=2)=C1 NPDIDUXTRAITDE-UHFFFAOYSA-N 0.000 description 2
- WGOOHIBXEKJTGZ-UHFFFAOYSA-N 2-fluoro-1,3,4,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(F)C(C)=C1C WGOOHIBXEKJTGZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229910019800 NbF 5 Inorganic materials 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910018287 SbF 5 Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000009918 complex formation Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- QUEBYVKXYIKVSO-UHFFFAOYSA-N m-propyltoluene Chemical compound CCCC1=CC=CC(C)=C1 QUEBYVKXYIKVSO-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- FJBPUXAJPOJYJG-UHFFFAOYSA-N 1,3-bis(2,2-dimethylpropyl)-5-methylbenzene Chemical compound CC1=CC(CC(C)(C)C)=CC(CC(C)(C)C)=C1 FJBPUXAJPOJYJG-UHFFFAOYSA-N 0.000 description 1
- NQGNNDCCPKSMSE-UHFFFAOYSA-N 1-(2,2-dimethylpropyl)-2,4-dimethylbenzene Chemical compound CC1=CC=C(CC(C)(C)C)C(C)=C1 NQGNNDCCPKSMSE-UHFFFAOYSA-N 0.000 description 1
- ILCKOOIACFJEEW-UHFFFAOYSA-N 1-(2,2-dimethylpropyl)-3,5-dimethylbenzene Chemical compound CC1=CC(C)=CC(CC(C)(C)C)=C1 ILCKOOIACFJEEW-UHFFFAOYSA-N 0.000 description 1
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- JEWRVXUTAZWZAD-UHFFFAOYSA-N 1-fluoro-2,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(C)C(F)=C1 JEWRVXUTAZWZAD-UHFFFAOYSA-N 0.000 description 1
- SDHYGAUOCHFYSR-UHFFFAOYSA-N 1-methyl-3-(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC=CC(C)=C1 SDHYGAUOCHFYSR-UHFFFAOYSA-N 0.000 description 1
- OYMMYOTXMKNHEH-UHFFFAOYSA-N 2-fluoro-1,3,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(F)=C1C OYMMYOTXMKNHEH-UHFFFAOYSA-N 0.000 description 1
- UXSXDXAQKQEYIJ-UHFFFAOYSA-N 5-fluoro-1,2,3-trimethylbenzene Chemical compound CC1=CC(F)=CC(C)=C1C UXSXDXAQKQEYIJ-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XPVGVLZDWNNALU-UHFFFAOYSA-N F.[P] Chemical compound F.[P] XPVGVLZDWNNALU-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 241000862969 Stella Species 0.000 description 1
- 229910004529 TaF 5 Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000001462 antimony Chemical class 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- 230000002542 deteriorative effect Effects 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
- 238000011049 filling Methods 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N isopropyl-benzene Natural products CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000004376 petroleum reforming Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 150000005199 trimethylbenzenes Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0426—Counter-current multistage extraction towers in a vertical or sloping position
- B01D11/043—Counter-current multistage extraction towers in a vertical or sloping position with stationary contacting elements, sieve plates or loose contacting elements
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/152—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by forming adducts or complexes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JPJP-P-2012-147540 | 2012-06-29 | ||
| JP2012147540 | 2012-06-29 | ||
| PCT/JP2013/067383 WO2014003000A1 (ja) | 2012-06-29 | 2013-06-25 | アルキル芳香族炭化水素の分離方法および分離装置 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20150021956A KR20150021956A (ko) | 2015-03-03 |
| KR102048250B1 true KR102048250B1 (ko) | 2019-11-25 |
Family
ID=49783146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147036424A Active KR102048250B1 (ko) | 2012-06-29 | 2013-06-25 | 알킬 방향족 탄화수소의 분리방법 및 분리장치 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US9896397B2 (enExample) |
| EP (1) | EP2868644B1 (enExample) |
| JP (1) | JP6146411B2 (enExample) |
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| IN2015DN00188A (enExample) | 2012-06-29 | 2015-06-12 | Mitsubishi Gas Chemical Co | |
| WO2016097370A2 (en) | 2014-12-18 | 2016-06-23 | Bergen Teknologioverføring As | Anti-axl antagonistic antibodies |
| CN111410182A (zh) * | 2020-03-31 | 2020-07-14 | 福建省龙德新能源股份有限公司 | 一种回用六氟磷酸锂合成尾气中五氟化磷的方法 |
| US12441672B2 (en) * | 2020-08-26 | 2025-10-14 | China Petroleum & Chemical Corporation | Composite adsorbent for separation of ethylbenzene by adsorption distillation and application thereof |
| CN113248343A (zh) * | 2021-05-13 | 2021-08-13 | 天津济泰科技有限公司 | 隔板塔分离重整碳十芳烃的工艺及方法 |
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| US2662925A (en) | 1951-06-29 | 1953-12-15 | Standard Oil Co | Isomerization of xylenes |
| US3512931A (en) * | 1966-08-12 | 1970-05-19 | Mitsubishi Gas Chemical Co | Process for recovering hydrogen fluoride and boron fluoride |
| JPS4719256Y1 (enExample) | 1966-11-19 | 1972-07-01 | ||
| JPS4737408Y1 (enExample) | 1967-08-03 | 1972-11-13 | ||
| US3562347A (en) * | 1967-12-15 | 1971-02-09 | Japan Gas Chemical Co | Process for extract-isomerization of xylene isomers |
| GB1272960A (en) * | 1968-09-03 | 1972-05-03 | Exxon Research Engineering Co | Complexing ligands with bimetallic salts and derivatives thereof |
| US3592865A (en) | 1968-09-03 | 1971-07-13 | Exxon Research Engineering Co | Separation and recovery of complexible ligands by liquid exchange |
| US3644553A (en) * | 1968-12-17 | 1972-02-22 | Japan Gas Chemical Co | Process for the decomposition of a solution of hydrogen fluoride-boron trifluoride-xylenes complex |
| US3766286A (en) * | 1971-06-25 | 1973-10-16 | Exxon Research Engineering Co | Process for the isomerization of hydrocarbons |
| US5177302A (en) | 1990-11-27 | 1993-01-05 | Director-General, Agency Of Industrial Science And Technology | Process for separating isomers of disubstituted benzenes and agents to be used therefor |
| JPH0774170B2 (ja) * | 1991-01-18 | 1995-08-09 | 工業技術院長 | ベンゼン二置換異性体の分離法及びその分離用薬剤 |
| JPH06305989A (ja) * | 1993-02-23 | 1994-11-01 | Sekiyu Sangyo Kasseika Center | 錯体形成による分離回収方法 |
| JP2650862B2 (ja) | 1994-11-22 | 1997-09-10 | ユーオーピー | 芳香族炭化水素からメタキシレンの吸着分離法 |
| DE102004004683A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Herstellung von Dinitrilen |
| WO2006009553A1 (en) * | 2004-06-23 | 2006-01-26 | Exxonmobil Chemical Patents Inc. | Methods for separating mixture components |
| CN103857651B (zh) * | 2011-08-29 | 2016-05-04 | 沙特基础工业公司 | 用于制备二取代的琥珀酸酯的方法 |
| IN2015DN00188A (enExample) * | 2012-06-29 | 2015-06-12 | Mitsubishi Gas Chemical Co |
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| TW201412704A (zh) | 2014-04-01 |
| US9896397B2 (en) | 2018-02-20 |
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| WO2014003000A9 (ja) | 2014-03-27 |
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| CN104411666B (zh) | 2016-04-13 |
| KR20150021956A (ko) | 2015-03-03 |
| US20150141730A1 (en) | 2015-05-21 |
| SG11201408633WA (en) | 2015-02-27 |
| EP2868644B1 (en) | 2018-08-01 |
| CN104411666A (zh) | 2015-03-11 |
| EP2868644A4 (en) | 2016-02-10 |
| JPWO2014003000A1 (ja) | 2016-06-02 |
| IN2015DN00188A (enExample) | 2015-06-12 |
| JP6146411B2 (ja) | 2017-06-14 |
| US20180016209A1 (en) | 2018-01-18 |
| TWI591053B (zh) | 2017-07-11 |
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