CS234023B2 - Method of anthracin separation and purification from anthracion oil - Google Patents
Method of anthracin separation and purification from anthracion oil Download PDFInfo
- Publication number
- CS234023B2 CS234023B2 CS807268A CS726880A CS234023B2 CS 234023 B2 CS234023 B2 CS 234023B2 CS 807268 A CS807268 A CS 807268A CS 726880 A CS726880 A CS 726880A CS 234023 B2 CS234023 B2 CS 234023B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- anthracene
- crude
- oil
- weight
- extraction
- Prior art date
Links
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title claims abstract description 252
- 238000000034 method Methods 0.000 title claims description 57
- 238000000926 separation method Methods 0.000 title claims description 14
- 238000000746 purification Methods 0.000 title description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 42
- 238000002425 crystallisation Methods 0.000 claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 239000013078 crystal Substances 0.000 claims abstract description 16
- 239000003085 diluting agent Substances 0.000 claims abstract description 6
- 239000003921 oil Substances 0.000 claims description 53
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 44
- 238000000605 extraction Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 24
- 230000008025 crystallization Effects 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 17
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 10
- 239000006227 byproduct Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 6
- 239000012452 mother liquor Substances 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- 235000019198 oils Nutrition 0.000 claims 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- MSMPBHLDQUXNEE-UHFFFAOYSA-N CN1C(CCC1)=O.C1=CC=CC=2C3=CC=CC=C3NC12 Chemical compound CN1C(CCC1)=O.C1=CC=CC=2C3=CC=CC=C3NC12 MSMPBHLDQUXNEE-UHFFFAOYSA-N 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- 241000700159 Rattus Species 0.000 claims 1
- 235000019486 Sunflower oil Nutrition 0.000 claims 1
- 239000002600 sunflower oil Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 abstract description 4
- 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 abstract description 3
- 150000004056 anthraquinones Chemical class 0.000 abstract description 3
- 239000003245 coal Substances 0.000 abstract description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 abstract 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000002244 precipitate Substances 0.000 description 30
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 20
- 238000004821 distillation Methods 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 150000001454 anthracenes Chemical class 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 238000005119 centrifugation Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 230000008929 regeneration Effects 0.000 description 5
- 238000011069 regeneration method Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 3
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 239000000306 component Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 201000003762 Chilblain lupus Diseases 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- RHZUVFJBSILHOK-UHFFFAOYSA-N anthracen-1-ylmethanolate Chemical compound C1=CC=C2C=C3C(C[O-])=CC=CC3=CC2=C1 RHZUVFJBSILHOK-UHFFFAOYSA-N 0.000 description 2
- OAYONPVQZPIHBU-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21.C1=CC=CC2=CC3=CC=CC=C3C=C21 OAYONPVQZPIHBU-UHFFFAOYSA-N 0.000 description 2
- 239000003830 anthracite Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- -1 ethyl ethyl Chemical group 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 230000010349 pulsation Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- OUXCBPLFCPMLQZ-WOPPDYDQSA-N 4-amino-1-[(2r,3s,4s,5r)-4-hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]-5-iodopyrimidin-2-one Chemical compound C[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N=C(N)C(I)=C1 OUXCBPLFCPMLQZ-WOPPDYDQSA-N 0.000 description 1
- YKKIJKQVGBPUKN-UHFFFAOYSA-N C1=CC=C2C3=CC=CC=C3NC2=C1.C1=CC=CC2=CC3=CC=CC=C3C=C21.C1=CC=C2C3=CC=CC=C3C=CC2=C1 Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1.C1=CC=CC2=CC3=CC=CC=C3C=C21.C1=CC=C2C3=CC=CC=C3C=CC2=C1 YKKIJKQVGBPUKN-UHFFFAOYSA-N 0.000 description 1
- 208000006558 Dental Calculus Diseases 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000255632 Tabanus atratus Species 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- LJZJHELAFLRVSU-UHFFFAOYSA-N anthracene;phenanthrene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21.C1=CC=C2C3=CC=CC=C3C=CC2=C1 LJZJHELAFLRVSU-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 230000001149 cognitive effect Effects 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 239000011285 coke tar Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000005138 cryopreservation Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- PUPFATUGTIQBQA-UZQPLGKSSA-N fluorophen Chemical compound C([C@@]1(C)C2=CC(O)=CC=C2C[C@H]2[C@@H]1C)CN2CCC1=CC=C(F)C=C1 PUPFATUGTIQBQA-UZQPLGKSSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000008774 maternal effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10C—WORKING-UP PITCH, ASPHALT, BITUMEN, TAR; PYROLIGNEOUS ACID
- C10C1/00—Working-up tar
- C10C1/18—Working-up tar by extraction with selective solvents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL21919979A PL125041B1 (en) | 1979-10-25 | 1979-10-25 | Method of separation of raw anthracene from anthracene oil |
| PL21939979A PL125053B1 (en) | 1979-11-02 | 1979-11-02 | Method of purification of anthracene |
| PL22647480A PL131628B1 (en) | 1980-08-29 | 1980-08-29 | Method of separation of anthracene from anthracene oil |
| PL22661580A PL131664B3 (en) | 1980-09-06 | 1980-09-06 | Method of purification of anthracene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS234023B2 true CS234023B2 (en) | 1985-03-14 |
Family
ID=27484417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS807268A CS234023B2 (en) | 1979-10-25 | 1980-10-27 | Method of anthracin separation and purification from anthracion oil |
Country Status (3)
| Country | Link |
|---|---|
| CS (1) | CS234023B2 (de) |
| DE (1) | DE3040431C2 (de) |
| FR (1) | FR2467835B1 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3275737D1 (en) * | 1982-06-29 | 1987-04-23 | Domtar Inc | Process for modifying coal tar materials |
| CN101130479B (zh) * | 2006-08-24 | 2011-02-09 | 宝山钢铁股份有限公司 | 从煤焦油蒽油馏份中提取低菲蒽油的工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE42053C (de) * | CHEMISCHE FABRIKS - ACTIEN-GESELLSCHAFT in Hamburg | Verfahren zur Reinigung des Rohanthracens | ||
| FR960364A (de) * | 1950-04-18 | |||
| FR1064366A (fr) * | 1952-10-13 | 1954-05-13 | Bristol & West Tar Distillers | Procédé de purification des composés aromatiques cristallisables présents dans les distillats des goudrons |
| US3407209A (en) * | 1965-12-27 | 1968-10-22 | Great Lakes Carbon Corp | Method for the recovery of carbazole from coal tar fractions |
| JPS4835069B1 (de) * | 1970-05-11 | 1973-10-25 |
-
1980
- 1980-10-27 FR FR8022968A patent/FR2467835B1/fr not_active Expired
- 1980-10-27 DE DE3040431A patent/DE3040431C2/de not_active Expired
- 1980-10-27 CS CS807268A patent/CS234023B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE3040431C2 (de) | 1983-02-17 |
| DE3040431A1 (de) | 1981-05-07 |
| FR2467835B1 (fr) | 1985-06-21 |
| FR2467835A1 (fr) | 1981-04-30 |
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