CA1106368A - Process for the mononitration of anthraquinone - Google Patents
Process for the mononitration of anthraquinoneInfo
- Publication number
- CA1106368A CA1106368A CA288,662A CA288662A CA1106368A CA 1106368 A CA1106368 A CA 1106368A CA 288662 A CA288662 A CA 288662A CA 1106368 A CA1106368 A CA 1106368A
- Authority
- CA
- Canada
- Prior art keywords
- anthraquinone
- sulphuric acid
- nitric acid
- acid
- mixture
- 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
- 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 title claims abstract description 113
- 150000004056 anthraquinones Chemical class 0.000 title claims abstract description 110
- 238000000034 method Methods 0.000 title claims abstract description 110
- 230000008569 process Effects 0.000 title claims abstract description 75
- 239000000203 mixture Substances 0.000 claims abstract description 97
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 91
- 235000011149 sulphuric acid Nutrition 0.000 claims abstract description 90
- 239000001117 sulphuric acid Substances 0.000 claims abstract description 87
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 80
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 59
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000463 material Substances 0.000 claims abstract description 10
- -1 anthraquinone compounds Chemical class 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims description 58
- 238000006396 nitration reaction Methods 0.000 claims description 55
- 239000007788 liquid Substances 0.000 claims description 34
- 239000012074 organic phase Substances 0.000 claims description 33
- 239000012071 phase Substances 0.000 claims description 24
- 238000010924 continuous production Methods 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000003541 multi-stage reaction Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 45
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 10
- 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 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 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 7
- 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 6
- 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
- 150000007513 acids Chemical class 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 description 5
- 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
- 238000007792 addition Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 230000000802 nitrating effect Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000470 constituent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 230000036647 reaction Effects 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 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 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 238000009434 installation Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000012899 de-mixing Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 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 1
- UXHQLGLGLZKHTC-CUNXSJBXSA-N 4-[(3s,3ar)-3-cyclopentyl-7-(4-hydroxypiperidine-1-carbonyl)-3,3a,4,5-tetrahydropyrazolo[3,4-f]quinolin-2-yl]-2-chlorobenzonitrile Chemical compound C1CC(O)CCN1C(=O)C1=CC=C(C=2[C@@H]([C@H](C3CCCC3)N(N=2)C=2C=C(Cl)C(C#N)=CC=2)CC2)C2=N1 UXHQLGLGLZKHTC-CUNXSJBXSA-N 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- 241000237074 Centris Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000009850 completed effect Effects 0.000 description 1
- 239000000110 cooling liquid Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013462 industrial intermediate Substances 0.000 description 1
- 238000010406 interfacial reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 230000001360 synchronised effect Effects 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2646649.9 | 1976-10-15 | ||
| DE19762646649 DE2646649C3 (de) | 1976-10-15 | 1976-10-15 | Verfahren zur Mononitrierung von Anthrachinon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1106368A true CA1106368A (en) | 1981-08-04 |
Family
ID=5990573
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA288,662A Expired CA1106368A (en) | 1976-10-15 | 1977-10-13 | Process for the mononitration of anthraquinone |
Country Status (10)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104030927B (zh) * | 2014-06-18 | 2016-06-22 | 江苏亚邦染料股份有限公司 | 一种以金属改性分子筛为催化剂制备1-硝基蒽醌的方法 |
| CN114149326A (zh) * | 2021-12-14 | 2022-03-08 | 江苏亚邦染料股份有限公司 | 一种超重力硝化反应器制备1-硝基蒽醌的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE789702A (fr) * | 1971-10-07 | 1973-02-01 | Sumitomo Chemical Co | Procede de preparation de dinitroanthraquinones |
| FR2240207A1 (en) * | 1973-08-10 | 1975-03-07 | Ciba Geigy Ag | Pure 1-nitroanthraquinone (derivs) prodn - by nitrating anthraquinone (derivs) in hydrofluoric acid, for use in dye mfr |
-
1976
- 1976-10-15 DE DE19762646649 patent/DE2646649C3/de not_active Expired
-
1977
- 1977-09-15 IN IN238/DEL/77A patent/IN146815B/en unknown
- 1977-10-10 GB GB4208177A patent/GB1553333A/en not_active Expired
- 1977-10-11 CH CH1241477A patent/CH633770A5/de not_active IP Right Cessation
- 1977-10-13 CA CA288,662A patent/CA1106368A/en not_active Expired
- 1977-10-13 JP JP12194177A patent/JPS5350151A/ja active Granted
- 1977-10-13 AT AT731877A patent/AT350543B/de not_active IP Right Cessation
- 1977-10-14 FR FR7731061A patent/FR2367733A1/fr active Granted
- 1977-10-14 BR BR7706874A patent/BR7706874A/pt unknown
- 1977-10-14 BE BE2056339A patent/BE859719A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS622580B2 (enrdf_load_stackoverflow) | 1987-01-20 |
| JPS5350151A (en) | 1978-05-08 |
| FR2367733B1 (enrdf_load_stackoverflow) | 1981-05-08 |
| DE2646649B2 (de) | 1981-01-08 |
| DE2646649C3 (de) | 1982-01-28 |
| GB1553333A (en) | 1979-09-26 |
| BR7706874A (pt) | 1978-07-18 |
| CH633770A5 (en) | 1982-12-31 |
| DE2646649A1 (de) | 1978-04-20 |
| AT350543B (de) | 1979-06-11 |
| ATA731877A (de) | 1978-11-15 |
| BE859719A (fr) | 1978-04-14 |
| FR2367733A1 (fr) | 1978-05-12 |
| IN146815B (enrdf_load_stackoverflow) | 1979-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |