GB1564373A - Process for the separation of dinitroanthraquinone mixtures - Google Patents
Process for the separation of dinitroanthraquinone mixtures Download PDFInfo
- Publication number
- GB1564373A GB1564373A GB3451777A GB3451777A GB1564373A GB 1564373 A GB1564373 A GB 1564373A GB 3451777 A GB3451777 A GB 3451777A GB 3451777 A GB3451777 A GB 3451777A GB 1564373 A GB1564373 A GB 1564373A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dinitroanthraquinone
- separation
- nitrobenzene
- mixture
- 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 89
- 238000000926 separation method Methods 0.000 title claims abstract description 79
- 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 49
- 238000000034 method Methods 0.000 title claims abstract description 39
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 126
- 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 85
- 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 73
- 238000009835 boiling Methods 0.000 claims abstract description 3
- 238000005406 washing Methods 0.000 claims description 15
- 239000000470 constituent Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 3
- 239000001000 anthraquinone dye Substances 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 description 39
- 239000000243 solution Substances 0.000 description 35
- 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 25
- 238000002955 isolation Methods 0.000 description 25
- 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 18
- 238000003756 stirring Methods 0.000 description 17
- 239000000047 product Substances 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 15
- 150000004056 anthraquinones Chemical class 0.000 description 15
- 238000002425 crystallisation Methods 0.000 description 13
- 239000012452 mother liquor Substances 0.000 description 13
- 238000006396 nitration reaction Methods 0.000 description 13
- 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 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- 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 9
- 239000002244 precipitate Substances 0.000 description 9
- 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 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 8
- 229910017604 nitric acid Inorganic materials 0.000 description 8
- 238000004064 recycling Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation 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 5
- 239000013078 crystal Substances 0.000 description 5
- 235000011149 sulphuric acid Nutrition 0.000 description 5
- 239000001117 sulphuric acid Substances 0.000 description 5
- 238000002360 preparation method 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
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000007858 starting material 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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 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
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- FWEQPMZEKHHFTB-UHFFFAOYSA-N n-(5-amino-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 FWEQPMZEKHHFTB-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- GCBZQUPYMOMOEZ-UHFFFAOYSA-N 1,3-dinitroanthracene-9,10-dione Chemical compound [N+](=O)([O-])C1=CC(=CC=2C(C3=CC=CC=C3C(C12)=O)=O)[N+](=O)[O-] GCBZQUPYMOMOEZ-UHFFFAOYSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- -1 amino compound Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process 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
- 238000005191 phase separation Methods 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 239000002904 solvent 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 (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 |
|---|---|
| GB1564373A true GB1564373A (en) | 1980-04-10 |
Family
ID=5986033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3451777A Expired GB1564373A (en) | 1976-08-21 | 1977-08-17 | 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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102056475A (zh) * | 2008-06-04 | 2011-05-11 | 阿德里安·约翰尼斯·斯塔夫伦 | 锹 |
Families Citing this family (7)
| 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 |
| 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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102056475A (zh) * | 2008-06-04 | 2011-05-11 | 阿德里安·约翰尼斯·斯塔夫伦 | 锹 |
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 |
| CA1111032A (en) | 1981-10-20 |
| BE857926A (fr) | 1978-02-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |