CA1111032A - Process for the separation of dinitroanthraquinone mixtures - Google Patents
Process for the separation of dinitroanthraquinone mixturesInfo
- Publication number
- CA1111032A CA1111032A CA285,064A CA285064A CA1111032A CA 1111032 A CA1111032 A CA 1111032A CA 285064 A CA285064 A CA 285064A CA 1111032 A CA1111032 A CA 1111032A
- Authority
- CA
- Canada
- Prior art keywords
- dinitroanthraquinone
- separation
- mixture
- nitrobenzene
- weight
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 97
- 238000000926 separation method Methods 0.000 title claims abstract description 77
- 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 claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 33
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 115
- 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 claims abstract description 69
- 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 claims abstract description 63
- 239000000470 constituent Substances 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims abstract description 9
- 238000009835 boiling Methods 0.000 claims abstract description 3
- 238000005406 washing Methods 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 description 40
- 239000000243 solution Substances 0.000 description 31
- 238000002955 isolation Methods 0.000 description 25
- 238000003756 stirring Methods 0.000 description 19
- 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 18
- 239000000047 product Substances 0.000 description 18
- 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 15
- 150000004056 anthraquinones Chemical class 0.000 description 15
- 239000012452 mother liquor Substances 0.000 description 14
- 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 13
- 238000002425 crystallisation Methods 0.000 description 13
- 238000006396 nitration reaction Methods 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 12
- 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 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 10
- 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 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 9
- 229910017604 nitric acid Inorganic materials 0.000 description 9
- 238000004821 distillation Methods 0.000 description 8
- 238000004064 recycling Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 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
- 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
- 239000012065 filter cake Substances 0.000 description 5
- 235000011149 sulphuric acid Nutrition 0.000 description 5
- 239000001117 sulphuric acid Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- -1 1,1-dinitroanthraquinone Chemical compound 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- 241000969130 Atthis Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000802 nitrating 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
- 238000005191 phase separation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2637733.3 | 1976-08-21 | ||
| DE19762637733 DE2637733C3 (de) | 1976-08-21 | 1976-08-21 | Verfahren zur Trennung von Dinitroanthrachinon-Gemischen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1111032A true CA1111032A (en) | 1981-10-20 |
Family
ID=5986033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA285,064A Expired CA1111032A (en) | 1976-08-21 | 1977-08-19 | Process for the separation of dinitroanthraquinone mixtures |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5325549A (enExample) |
| AT (1) | AT350542B (enExample) |
| BE (1) | BE857926A (enExample) |
| CA (1) | CA1111032A (enExample) |
| CH (1) | CH634038A5 (enExample) |
| DE (1) | DE2637733C3 (enExample) |
| FR (1) | FR2362111A1 (enExample) |
| GB (1) | GB1564373A (enExample) |
| IT (1) | IT1079921B (enExample) |
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 (enExample) * | ||||
| BE789702A (fr) * | 1971-10-07 | 1973-02-01 | Sumitomo Chemical Co | Procede de preparation de dinitroanthraquinones |
| JPS4976851A (enExample) * | 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 (enExample) | 1981-09-04 |
| FR2362111A1 (fr) | 1978-03-17 |
| CH634038A5 (en) | 1983-01-14 |
| IT1079921B (it) | 1985-05-13 |
| JPS5325549A (en) | 1978-03-09 |
| JPS5546382B2 (enExample) | 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 |
| BE857926A (fr) | 1978-02-20 |
| GB1564373A (en) | 1980-04-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |