DE1117569B - Verfahren zur Herstellung von 4-Oxyfluoranthen und seinen Abkoemmlingen - Google Patents
Verfahren zur Herstellung von 4-Oxyfluoranthen und seinen AbkoemmlingenInfo
- Publication number
- DE1117569B DE1117569B DEF31099A DEF0031099A DE1117569B DE 1117569 B DE1117569 B DE 1117569B DE F31099 A DEF31099 A DE F31099A DE F0031099 A DEF0031099 A DE F0031099A DE 1117569 B DE1117569 B DE 1117569B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- oxyfluoranthene
- volume
- weight
- melting point
- 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
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- CBOZPIUPCOHJKS-UHFFFAOYSA-N O=C1C=2CCCC3=C4C=CC=CC4=C(C=C1)C3=2 Chemical compound O=C1C=2CCCC3=C4C=CC=CC4=C(C=C1)C3=2 CBOZPIUPCOHJKS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 8
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 6
- -1 amino compound Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 description 3
- OIGRHMGALPXFHI-UHFFFAOYSA-N (sulfamoylamino)ethane Chemical class CCNS(N)(=O)=O OIGRHMGALPXFHI-UHFFFAOYSA-N 0.000 description 2
- PIHGQKMEAMSUNA-UHFFFAOYSA-N 3-Nitrofluoranthene Chemical compound C12=CC=CC=C2C2=CC=CC3=C2C1=CC=C3[N+](=O)[O-] PIHGQKMEAMSUNA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- VHGJAFIHUSTRGB-UHFFFAOYSA-N fluoranthen-3-amine Chemical compound C12=CC=CC=C2C2=CC=CC3=C2C1=CC=C3N VHGJAFIHUSTRGB-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- DFYPVJHFCVSDEV-UHFFFAOYSA-N methyl 2-chloro-9h-fluorene-9-carboxylate Chemical compound C1=C(Cl)C=C2C(C(=O)OC)C3=CC=CC=C3C2=C1 DFYPVJHFCVSDEV-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/44—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed ring system having more than three rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF31099A DE1117569B (de) | 1960-04-28 | 1960-04-28 | Verfahren zur Herstellung von 4-Oxyfluoranthen und seinen Abkoemmlingen |
| BE603206A BE603206A (fr) | 1960-04-28 | 1961-04-28 | Procédé de préparation de 4-hydroxyfluoranthène et de ses dérivés |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF31099A DE1117569B (de) | 1960-04-28 | 1960-04-28 | Verfahren zur Herstellung von 4-Oxyfluoranthen und seinen Abkoemmlingen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1117569B true DE1117569B (de) | 1961-11-23 |
Family
ID=7094045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF31099A Pending DE1117569B (de) | 1960-04-28 | 1960-04-28 | Verfahren zur Herstellung von 4-Oxyfluoranthen und seinen Abkoemmlingen |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE603206A (fr) |
| DE (1) | DE1117569B (fr) |
-
1960
- 1960-04-28 DE DEF31099A patent/DE1117569B/de active Pending
-
1961
- 1961-04-28 BE BE603206A patent/BE603206A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE603206A (fr) | 1961-10-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1117569B (de) | Verfahren zur Herstellung von 4-Oxyfluoranthen und seinen Abkoemmlingen | |
| DE491225C (de) | Verfahren zur Einfuehrung von Rhodangruppen in organische Verbindungen | |
| DE836800C (de) | Verfahren zur Herstellung von 21-Oxy-pregnen-(5)-ol-(3)-on-(20)-Abkoemmlingen | |
| DE642717C (de) | Verfahren zur Herstellung von 1, 5, 9-Anthracentricarbonsaeure oder deren Anhydrid | |
| DE658780C (de) | Verfahren zur Herstellung von Pyrenabkoemmlingen | |
| DE681867C (de) | Verfahren zur Herstellung monohalogenierter, ungesaettigter, einen Sterinkern enthaltender Ketone | |
| DE390666C (de) | Verfahren zur Darstellung von wasserunloeslichen Azofarbstoffen | |
| DE602857C (de) | Verfahren zur Herstellung von Leukoschwefelsaeureestern von Kuepenfarbstoffen | |
| CH358093A (de) | Verfahren zur Herstellung von Thiophendioxyd-Verbindungen | |
| DE659881C (de) | Verfahren zur Herstellung von Dehydrobinaphthylendiimin und seinen Substitutionsprodukten | |
| DE597325C (de) | Verfahren zur Herstellung von Kondensationsprodukten der Anthracenreihe | |
| CH302372A (de) | Verfahren zur Herstellung einer neuen Acetoacetylaminoverbindung. | |
| DE863968C (de) | Verfahren zur Herstellung neuer, esterartiger Azofarbstoffderivate | |
| DE1083276B (de) | Verfahren zur Herstellung von 1-Oxynaphthalin-3-carbonsaeuren und ihren Abkoemmlingen | |
| DE396509C (de) | Verfahren zur Darstellung von stickstoffhaltigen Anthrachinonderivaten | |
| DE516845C (de) | Verfahren zur Darstellung von Salzen saurer Schwefelsaeureester von Nitroanthrahydrochinonen | |
| DE522173C (de) | Verfahren zur Darstellung von Naphthoylenbenzimidazol-4-dialkylacetyl-5-carbonsaeuren | |
| DE630220C (de) | Verfahren zur Herstellung von Abkoemmlingen der Anthrachinonreihe | |
| DE502044C (de) | Verfahren zur Darstellung von 2-Acylamino-9, 10-anthrahydrochinonen und deren 9, 10-Sauerstoffsubstitutionsprodukten | |
| DE897404C (de) | Verfahren zur Herstellung von substituierten Phthalsaeuren oder deren Derivaten | |
| AT223724B (de) | Verfahren zur Herstellung von neuen Cyaninfarbstoffen | |
| AT95240B (de) | Verfahren zur Herstellung von 1-Arylamido-2-naphtholen. | |
| DE500162C (de) | Verfahren zur Darstellung von 4-Methyl-6-halogen-3-oxy-1-thionaphthenen | |
| DE621455C (de) | Verfahren zur Herstellung von Verbindungen der Bz-2-Azabenzanthronreihe | |
| DE439290C (de) | Vefahren zur Herstellung von Naphthooxythiophenen |