JPH02199192A - コールタール誘導アントラセンの分離及び精製方法 - Google Patents
コールタール誘導アントラセンの分離及び精製方法Info
- Publication number
- JPH02199192A JPH02199192A JP1312253A JP31225389A JPH02199192A JP H02199192 A JPH02199192 A JP H02199192A JP 1312253 A JP1312253 A JP 1312253A JP 31225389 A JP31225389 A JP 31225389A JP H02199192 A JPH02199192 A JP H02199192A
- Authority
- JP
- Japan
- Prior art keywords
- anthracene
- crystallizer
- oil
- solvent
- crystals
- 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.)
- Pending
Links
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title claims abstract description 214
- 238000000926 separation method Methods 0.000 title claims description 13
- 238000000746 purification Methods 0.000 title claims description 8
- 239000011280 coal tar Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 claims abstract description 50
- 239000002904 solvent Substances 0.000 claims abstract description 29
- 239000013078 crystal Substances 0.000 claims abstract description 26
- 238000002425 crystallisation Methods 0.000 claims abstract description 23
- 230000008025 crystallization Effects 0.000 claims abstract description 20
- 239000000725 suspension Substances 0.000 claims abstract description 11
- 230000005484 gravity Effects 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 9
- 238000005119 centrifugation Methods 0.000 claims abstract description 7
- 238000001816 cooling Methods 0.000 claims abstract description 5
- 239000003921 oil Substances 0.000 claims description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 16
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 15
- 230000007935 neutral effect Effects 0.000 claims description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- 238000005292 vacuum distillation Methods 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 3
- 125000005577 anthracene group Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 239000000571 coke Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 238000000197 pyrolysis Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 239000007790 solid phase Substances 0.000 claims description 2
- 239000000341 volatile oil Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- -1 aliphatic sulfoxide Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 239000012267 brine Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims 1
- 238000000956 solid--liquid extraction Methods 0.000 claims 1
- 239000000706 filtrate Substances 0.000 description 16
- 239000012452 mother liquor Substances 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 8
- 239000007791 liquid phase Substances 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000005626 carbonium group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 239000003305 oil spill Substances 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/27—Polycyclic condensed hydrocarbons containing three rings
- C07C15/28—Anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/14—Purification; Separation; Use of additives by crystallisation; Purification or separation of the crystals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL1988276093A PL158769B1 (en) | 1988-11-30 | 1988-11-30 | Method isolating and purifying antracene of chemistry-of-coke origin |
| PL276093 | 1988-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02199192A true JPH02199192A (ja) | 1990-08-07 |
Family
ID=20045247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1312253A Pending JPH02199192A (ja) | 1988-11-30 | 1989-11-30 | コールタール誘導アントラセンの分離及び精製方法 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPH02199192A (zh) |
| KR (1) | KR0157405B1 (zh) |
| CN (1) | CN1025183C (zh) |
| PL (1) | PL158769B1 (zh) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006022195A1 (en) * | 2004-08-23 | 2006-03-02 | Semiconductor Energy Laboratory Co., Ltd. | Method for purifying material comprising organic semiconductor, method for purifying material comprising pentacene, semiconductor device, and method for fabricating the semiconductor device |
| JP2006093668A (ja) * | 2004-08-23 | 2006-04-06 | Semiconductor Energy Lab Co Ltd | 有機半導体の精製方法及び半導体装置 |
| JP2010514755A (ja) * | 2006-12-29 | 2010-05-06 | ヒョスン・コーポレーション | 高純度の２，６−ジメチルナフタレンの連続結晶化分離精製方法およびその装置 |
| JP2013175600A (ja) * | 2012-02-24 | 2013-09-05 | Chuo Univ | 有機ｅｌ素子およびその製造方法 |
| CN105505453A (zh) * | 2016-01-15 | 2016-04-20 | 深圳前海新域能源科技有限公司 | 一种煤焦油无水脱盐脱金属的方法 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19613497C1 (de) * | 1996-04-04 | 1997-11-13 | Vft Ag | Destillationsverfahren zur Verbesserung der Reinproduktengewinnung aus Rohanthracen |
| CN100575957C (zh) * | 2005-12-19 | 2009-12-30 | 中国矿业大学 | 油煤渣的溶解及其组分分析方法 |
| CN104447181A (zh) * | 2014-11-17 | 2015-03-25 | 宁夏中远天宇科技有限公司 | 一种新型的精蒽的生产工艺的萃取工序 |
| CN105693459B (zh) * | 2016-03-08 | 2018-09-21 | 曲靖众一精细化工股份有限公司 | 一种转鼓提纯精蒽的工艺 |
| CN113024346B (zh) * | 2021-03-19 | 2023-01-10 | 浙江大学衢州研究院 | 一种蒽及其戊基化反应产物的混合物的分离方法 |
-
1988
- 1988-11-30 PL PL1988276093A patent/PL158769B1/pl unknown
-
1989
- 1989-11-30 JP JP1312253A patent/JPH02199192A/ja active Pending
- 1989-11-30 CN CN89108882A patent/CN1025183C/zh not_active Expired - Fee Related
- 1989-11-30 KR KR1019890017586A patent/KR0157405B1/ko not_active IP Right Cessation
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006022195A1 (en) * | 2004-08-23 | 2006-03-02 | Semiconductor Energy Laboratory Co., Ltd. | Method for purifying material comprising organic semiconductor, method for purifying material comprising pentacene, semiconductor device, and method for fabricating the semiconductor device |
| JP2006093668A (ja) * | 2004-08-23 | 2006-04-06 | Semiconductor Energy Lab Co Ltd | 有機半導体の精製方法及び半導体装置 |
| JP2010514755A (ja) * | 2006-12-29 | 2010-05-06 | ヒョスン・コーポレーション | 高純度の２，６−ジメチルナフタレンの連続結晶化分離精製方法およびその装置 |
| JP2013175600A (ja) * | 2012-02-24 | 2013-09-05 | Chuo Univ | 有機ｅｌ素子およびその製造方法 |
| CN105505453A (zh) * | 2016-01-15 | 2016-04-20 | 深圳前海新域能源科技有限公司 | 一种煤焦油无水脱盐脱金属的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR900007765A (ko) | 1990-06-01 |
| PL158769B1 (en) | 1992-10-30 |
| PL276093A1 (en) | 1990-06-11 |
| CN1043309A (zh) | 1990-06-27 |
| CN1025183C (zh) | 1994-06-29 |
| KR0157405B1 (ko) | 1998-12-01 |
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