JPH0216295B2 - - Google Patents
Info
- Publication number
- JPH0216295B2 JPH0216295B2 JP5681082A JP5681082A JPH0216295B2 JP H0216295 B2 JPH0216295 B2 JP H0216295B2 JP 5681082 A JP5681082 A JP 5681082A JP 5681082 A JP5681082 A JP 5681082A JP H0216295 B2 JPH0216295 B2 JP H0216295B2
- Authority
- JP
- Japan
- Prior art keywords
- support material
- nitrogen
- fraction
- aromatic hydrocarbon
- eluent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000463 material Substances 0.000 claims description 37
- 238000000926 separation method Methods 0.000 claims description 21
- 239000003480 eluent Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 8
- 239000003245 coal Substances 0.000 claims description 7
- 230000008929 regeneration Effects 0.000 claims description 7
- 238000011069 regeneration method Methods 0.000 claims description 7
- 239000000741 silica gel Substances 0.000 claims description 7
- 229910002027 silica gel Inorganic materials 0.000 claims description 7
- 239000011280 coal tar Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- -1 nitrogen-containing aromatic hydrocarbon Chemical class 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 20
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 238000010828 elution Methods 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000005292 vacuum distillation Methods 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 239000006184 cosolvent Substances 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910017464 nitrogen compound Inorganic materials 0.000 description 3
- 150000002830 nitrogen compounds Chemical class 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011269 tar Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000006004 Quartz sand Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000012435 analytical chromatography Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 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
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000012994 industrial processing Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
- C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
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)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813114346 DE3114346C2 (de) | 1981-04-09 | 1981-04-09 | Verfahren zur Gewinnung von stickstoffhaltigen aromatischen Kohlenwasserstoffen aus aromatischen Kohlenwasserstoffgemischen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57179157A JPS57179157A (en) | 1982-11-04 |
| JPH0216295B2 true JPH0216295B2 (enrdf_load_stackoverflow) | 1990-04-16 |
Family
ID=6129767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5681082A Granted JPS57179157A (en) | 1981-04-09 | 1982-04-07 | Method of obtaining nitrogen-containing aromatic hydrocarbons from aromatic hydrocarbon mixture |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS57179157A (enrdf_load_stackoverflow) |
| DE (1) | DE3114346C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2503704A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2096637B (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2046846T3 (es) * | 1990-07-19 | 1994-02-01 | Cindu Chemicals B.V. | Proceso para separar constituyentes polares y no polares de los destilados de alquitran de carbon. |
| WO2013181062A1 (en) * | 2012-05-31 | 2013-12-05 | Uop Llc | Methods and apparatus for treating a hydrocarbon stream |
| CN106701150B (zh) * | 2015-11-16 | 2018-12-28 | 神华集团有限责任公司 | 含酚油的脱氮处理方法和脱氮含酚油 |
| CN106000289B (zh) * | 2016-06-30 | 2019-08-27 | 中国海洋石油集团有限公司 | 一种芳烃溶剂油精制剂及制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2606143A (en) * | 1950-08-31 | 1952-08-05 | James R Smith | Refining of shale oil |
| US2943049A (en) * | 1957-01-25 | 1960-06-28 | Union Oil Co | Denitrogenation of hydrocarbon mixtures |
| DE1113998B (de) * | 1958-01-03 | 1961-09-21 | Bataafsche Petroleum | Verfahren zur Entfernung von geloesten organischen Stickstoffverbindungen aus fluessigen Kohlenwasserstoffen |
-
1981
- 1981-04-09 DE DE19813114346 patent/DE3114346C2/de not_active Expired
-
1982
- 1982-04-07 JP JP5681082A patent/JPS57179157A/ja active Granted
- 1982-04-08 FR FR8206206A patent/FR2503704A1/fr active Granted
- 1982-04-13 GB GB8210610A patent/GB2096637B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2096637A (en) | 1982-10-20 |
| DE3114346C2 (de) | 1986-07-17 |
| FR2503704A1 (fr) | 1982-10-15 |
| JPS57179157A (en) | 1982-11-04 |
| DE3114346A1 (de) | 1982-10-28 |
| FR2503704B3 (enrdf_load_stackoverflow) | 1984-02-10 |
| GB2096637B (en) | 1984-06-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Barker et al. | The separation of volatile liquid mixtures by continuous gas-liquid chromatography | |
| US4791235A (en) | Process for separating 2,6-dimethylnaphthalene | |
| JPH0216295B2 (enrdf_load_stackoverflow) | ||
| US5698174A (en) | Process for separating fullerenes | |
| DE69100647T2 (de) | Verfahren zur Abtrennung von polaren und nichtpolaren Bestandteilen aus Kohleteeröldestillaten. | |
| JP4646886B2 (ja) | ２，６−ジメチルナフタレンの分離および精製方法 | |
| US3725257A (en) | Process of separating aromatic hydrocarbons from hydrocarbon mixtures | |
| JPH06294789A (ja) | ガスクロマトグラフィー法 | |
| US5266292A (en) | Method of extracting dinitrogen pentoxide from its mixture with nitric acid | |
| US2682445A (en) | Process for the production of purified anhydrous zirconium tetrahalide | |
| US4441896A (en) | Process for recovering organic substances from spent air vapors | |
| US4977243A (en) | Separation of sterols from low-acid feeds with magnesium silicate and methyl-tert-butyl ether desorbent | |
| US3338031A (en) | Countercurrent gas chromatography and gas solid adsorption | |
| GB2096636A (en) | Separation of nitrogen- containing hydrocarbons from coal oil fractions | |
| US3029242A (en) | Separation of heterocyclic nitrogen | |
| JPH07191006A (ja) | 超臨界流体クロマト分離装置 | |
| GB2412074A (en) | Fluoride-containing stationary phase for liquid chromatography | |
| Markovec et al. | Identification of major perchloroaromatic compounds in waste products from the production of carbon tetrachloride and tetrachloroethylene | |
| US2912426A (en) | Separation process utilizing urea partition chromatography | |
| SU988857A1 (ru) | Способ получени жидкого парафина | |
| SU693249A1 (ru) | Способ приготовлени колонки дл газо-жидкостной хроматографии | |
| Conder et al. | Design of a production gas chromatograph for separating heat-sensitive materials | |
| SU1054776A1 (ru) | Способ дезактивации твердого носител дл газовой хроматографии | |
| JP3779087B2 (ja) | キシレノール異性体の分離精製方法 | |
| JPS62153233A (ja) | ２−メチルナフタレンの精製方法 |