CH634038A5 - Process for separating dinitroanthraquinone mixtures - Google Patents
Process for separating dinitroanthraquinone mixtures Download PDFInfo
- Publication number
- CH634038A5 CH634038A5 CH1002877A CH1002877A CH634038A5 CH 634038 A5 CH634038 A5 CH 634038A5 CH 1002877 A CH1002877 A CH 1002877A CH 1002877 A CH1002877 A CH 1002877A CH 634038 A5 CH634038 A5 CH 634038A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dinitroanthraquinone
- nitrobenzene
- separation
- mixture
- nitroanthraquinone
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title description 86
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 title description 48
- 238000000034 method Methods 0.000 title description 32
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 112
- MBIJFIUDKPXMAV-UHFFFAOYSA-N 1,8-dinitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC([N+]([O-])=O)=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] MBIJFIUDKPXMAV-UHFFFAOYSA-N 0.000 description 72
- 238000000926 separation method Methods 0.000 description 60
- XVMVHWDCRFNPQR-UHFFFAOYSA-N 1,5-dinitroanthracene-9,10-dione Chemical compound O=C1C=2C([N+](=O)[O-])=CC=CC=2C(=O)C2=C1C=CC=C2[N+]([O-])=O XVMVHWDCRFNPQR-UHFFFAOYSA-N 0.000 description 56
- 239000000706 filtrate Substances 0.000 description 44
- 239000000243 solution Substances 0.000 description 34
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 description 32
- 238000002955 isolation Methods 0.000 description 24
- 239000000047 product Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 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 16
- 150000004056 anthraquinones Chemical class 0.000 description 16
- FAVDZWIRBSMLOV-UHFFFAOYSA-N 1,7-dinitroanthracene-9,10-dione Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 FAVDZWIRBSMLOV-UHFFFAOYSA-N 0.000 description 14
- 238000002425 crystallisation Methods 0.000 description 14
- 230000008025 crystallization Effects 0.000 description 14
- 238000005406 washing Methods 0.000 description 13
- 239000012452 mother liquor Substances 0.000 description 12
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 229910017604 nitric acid Inorganic materials 0.000 description 9
- 238000004064 recycling Methods 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 7
- 239000012065 filter cake Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- QCVMOSGPTRRUQZ-UHFFFAOYSA-N 2-nitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 QCVMOSGPTRRUQZ-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- UQKJUEALIQRECQ-UHFFFAOYSA-N 1,6-dinitroanthracene-9,10-dione Chemical compound O=C1C2=CC([N+](=O)[O-])=CC=C2C(=O)C2=C1C=CC=C2[N+]([O-])=O UQKJUEALIQRECQ-UHFFFAOYSA-N 0.000 description 5
- OPXXCGAYBFDPHY-UHFFFAOYSA-N 2,6-dinitroanthracene-9,10-dione Chemical compound [O-][N+](=O)C1=CC=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 OPXXCGAYBFDPHY-UHFFFAOYSA-N 0.000 description 5
- XFLONXIGNOXKCG-UHFFFAOYSA-N 2,7-dinitroanthracene-9,10-dione Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 XFLONXIGNOXKCG-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000006396 nitration reaction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- 230000000802 nitrating effect Effects 0.000 description 4
- 238000005121 nitriding Methods 0.000 description 4
- VWBVCOPVKXNMMZ-UHFFFAOYSA-N 1,5-diaminoanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC=C2C(=O)C2=C1C=CC=C2N VWBVCOPVKXNMMZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- QWXDVWSEUJXVIK-UHFFFAOYSA-N 1,8-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(N)=C2C(=O)C2=C1C=CC=C2N QWXDVWSEUJXVIK-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- -1 for example Chemical compound 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- MHIIKMFLEZGYPH-UHFFFAOYSA-N n-(8-benzamido-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=1C(=O)C2=3)=CC=CC=1C(=O)C2=CC=CC=3NC(=O)C1=CC=CC=C1 MHIIKMFLEZGYPH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762637733 DE2637733C3 (de) | 1976-08-21 | 1976-08-21 | Verfahren zur Trennung von Dinitroanthrachinon-Gemischen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH634038A5 true CH634038A5 (en) | 1983-01-14 |
Family
ID=5986033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1002877A CH634038A5 (en) | 1976-08-21 | 1977-08-16 | Process for separating dinitroanthraquinone mixtures |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5325549A (OSRAM) |
| AT (1) | AT350542B (OSRAM) |
| BE (1) | BE857926A (OSRAM) |
| CA (1) | CA1111032A (OSRAM) |
| CH (1) | CH634038A5 (OSRAM) |
| DE (1) | DE2637733C3 (OSRAM) |
| FR (1) | FR2362111A1 (OSRAM) |
| GB (1) | GB1564373A (OSRAM) |
| IT (1) | IT1079921B (OSRAM) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2432014A1 (fr) * | 1978-07-27 | 1980-02-22 | Ugine Kuhlmann | Procede d'obtention d'a,a'-dinitro-anthraquinones de haute purete |
| FR2458536A2 (fr) * | 1978-07-27 | 1981-01-02 | Ugine Kuhlmann | Procede d'obtention d'a,a'-dinitro-anthraquinones de haute purete |
| DE2854427A1 (de) * | 1978-12-16 | 1980-06-26 | Bayer Ag | Verfahren und vorrichtung zur gewinnung von trockenem 1,5- und/oder 1,8- dinitroanthrachinon aus suspensionen, die festes 1,5- und/oder 1,8-dinitroanthrachinon und fluessiges nitrobenzol enthalten |
| US4291932A (en) | 1980-03-25 | 1981-09-29 | The United States Of America As Represented By The Secretary Of The Navy | Electrical connector receptacle assembly |
| DE3329453A1 (de) * | 1983-08-16 | 1985-03-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur gewinnung von reinem 1-nitroanthrachinon |
| JPH0811251B2 (ja) * | 1984-08-18 | 1996-02-07 | 愛知製鋼株式会社 | 冷間ロール成形における過負荷防止装置 |
| NL1035539C1 (nl) * | 2008-06-04 | 2008-06-20 | Adriaan Johannes Stoffelen | Een schop met een op een haaienvin lijkend snijdeel dat in een hoek van 90 graden op de schop staat en waarvan de voorkant ongeveer 45 graden bedraagt welke het mogelijk maakt de taraxacum uit de grond te verwijderen zonder het gazon te beschadigen. |
| US20170350621A1 (en) * | 2016-06-06 | 2017-12-07 | Frontline Aerospace, Inc | Secondary solar concentrator |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE167699C (OSRAM) * | ||||
| BE789702A (fr) * | 1971-10-07 | 1973-02-01 | Sumitomo Chemical Co | Procede de preparation de dinitroanthraquinones |
| JPS4976851A (OSRAM) * | 1972-12-05 | 1974-07-24 | ||
| JPS511709A (en) * | 1974-06-25 | 1976-01-08 | Mitsubishi Heavy Ind Ltd | Renzokusokoshijono itotooshihoho |
| DE2524747C3 (de) * | 1975-06-04 | 1980-12-18 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Isolierung von 1,5-/1,8-Dinitroanthrachinon mit einem hohen Gehalt an a , a '-Duutroverbindungen |
-
1976
- 1976-08-21 DE DE19762637733 patent/DE2637733C3/de not_active Expired
-
1977
- 1977-08-16 CH CH1002877A patent/CH634038A5/de not_active IP Right Cessation
- 1977-08-17 GB GB3451777A patent/GB1564373A/en not_active Expired
- 1977-08-19 CA CA285,064A patent/CA1111032A/en not_active Expired
- 1977-08-19 IT IT5072077A patent/IT1079921B/it active
- 1977-08-19 JP JP9879977A patent/JPS5325549A/ja active Granted
- 1977-08-19 AT AT603577A patent/AT350542B/de not_active IP Right Cessation
- 1977-08-19 FR FR7725463A patent/FR2362111A1/fr active Granted
- 1977-08-19 BE BE2056176A patent/BE857926A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2362111B1 (OSRAM) | 1981-09-04 |
| FR2362111A1 (fr) | 1978-03-17 |
| IT1079921B (it) | 1985-05-13 |
| JPS5325549A (en) | 1978-03-09 |
| JPS5546382B2 (OSRAM) | 1980-11-22 |
| DE2637733B2 (de) | 1981-07-30 |
| ATA603577A (de) | 1978-11-15 |
| DE2637733C3 (de) | 1982-05-06 |
| AT350542B (de) | 1979-06-11 |
| DE2637733A1 (de) | 1978-02-23 |
| CA1111032A (en) | 1981-10-20 |
| BE857926A (fr) | 1978-02-20 |
| GB1564373A (en) | 1980-04-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2400164C3 (de) | Verfahren zur Abtrennung von 1,5-Dinitroanthrachinon und 1,8-Dinitroanthrachinon aus Dinitro-anthrachinongemischen | |
| CH634038A5 (en) | Process for separating dinitroanthraquinone mixtures | |
| DE2524747C3 (de) | Verfahren zur Isolierung von 1,5-/1,8-Dinitroanthrachinon mit einem hohen Gehalt an a , a '-Duutroverbindungen | |
| EP0001087B1 (de) | Verfahren zur Herstellung von 1-Amino-4-bromanthrachinon-2-sulfonsäure | |
| US3963762A (en) | Process for producing 1,5-dinitroanthraquinone and 1,8-dinitroanthraquinone | |
| DE2637732C3 (de) | Verfahren zur Herstellung von Dinitroanthrachinon-Gemischen mit hohem 1,5- und 1,8-Dinitroanthrachinon-Gehalt | |
| DE2459164C3 (de) | Verfahren zur Herstellung von Dinitroanthrachinongemischen, die einen hohen Gehalt an 1,5- und 1,8-Dinitroverbindungen aufweisen | |
| DE2306611C3 (de) | Verfahren zur Herstellung von 1,5und 1,8-Dinitroanthrachinon | |
| DE2654648A1 (de) | Verfahren zur isolierung von 1,6- und 1,7-dinitroanthrachinon | |
| DE2334713A1 (de) | Verfahren zur isolierung von 1,5dinitroanthrachinon | |
| DE2346317C3 (de) | Verfahren zur Herstellung von Dinitroanthrachinonen | |
| DE2256644C2 (de) | Verfahren zur Herstellung von reinem 1-Nitro-anthrachinon | |
| DE2517435C3 (de) | Verfahren zur Gewinnung von 1,8-Dinitroanthrachinon aus Dinitroanthrachinon-Gemischen | |
| DE462053C (de) | Verfahren zur Herstellung von Monobenzoyldiaminoanthrachinonen | |
| DE2517436C3 (de) | Verfahren zur Gewinnung von 1,5-Dinitroanthrachinon aus Dinitroanthrachinon-Gemischen | |
| DE2654649A1 (de) | Verfahren zur herstellung von 1-nitroanthrachinon | |
| DE2164306A1 (de) | Verfahren zur herstellung von 1-nitroanthrachinon und 1-amino-anthrachinon | |
| DE2351590C3 (de) | Verfahren zur Gewinnung von 1,5-Dinitroanthrachinon und 1,8-Dinitroanthrachinon | |
| DE2545699A1 (de) | Verfahren zur trennung von 1,5- und 1,8-dinitroanthrachinon | |
| DE2438210A1 (de) | Verfahren zur nitrierung von anthrachinon und dessen derivaten | |
| EP0069910A1 (de) | Verfahren zur Herstellung von 1-Hydroxy-4-amino-5(8)-nitro-anthrachinon | |
| DD145098A5 (de) | Verfahren zur gewinnung von alpha,alpha'-dinitroanthrachinonen mit hoher reinheit | |
| DE2351590B2 (de) | Verfahren zur gewinnung von 1,5- dinitroanthrachinon und 1,8-dinitroanthrachinon | |
| DE1091554B (de) | Verfahren zur Herstellung von Anthrachinon durch Oxydation von Anthracen | |
| DE1099521B (de) | Verfahren zur Abtrennung von Iso- und Terephthalsaeure aus einem isomere Phthalsaeuren enthaltenden Gemisch |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |