CH632735A5 - Process for the preparation of 1-nitroanthraquinone - Google Patents
Process for the preparation of 1-nitroanthraquinone Download PDFInfo
- Publication number
- CH632735A5 CH632735A5 CH1460177A CH1460177A CH632735A5 CH 632735 A5 CH632735 A5 CH 632735A5 CH 1460177 A CH1460177 A CH 1460177A CH 1460177 A CH1460177 A CH 1460177A CH 632735 A5 CH632735 A5 CH 632735A5
- Authority
- CH
- Switzerland
- Prior art keywords
- nitroanthraquinone
- mixture
- dna
- nitrobenzene
- anthraquinone
- Prior art date
Links
- 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 title claims description 182
- 238000000034 method Methods 0.000 title claims description 85
- 238000002360 preparation method Methods 0.000 title claims description 5
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 140
- 239000000203 mixture Substances 0.000 claims description 123
- 239000000706 filtrate Substances 0.000 claims description 59
- 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 claims description 54
- 150000004056 anthraquinones Chemical class 0.000 claims description 47
- 239000012452 mother liquor Substances 0.000 claims description 46
- 238000002425 crystallisation Methods 0.000 claims description 44
- 230000008025 crystallization Effects 0.000 claims description 44
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 38
- 238000005406 washing Methods 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 23
- 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 claims description 16
- 238000001914 filtration Methods 0.000 claims description 16
- -1 anthraquinone compounds Chemical class 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 10
- 238000006396 nitration reaction Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000007872 degassing Methods 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 230000000802 nitrating effect Effects 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 2
- 239000010802 sludge Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 description 32
- 239000013078 crystal Substances 0.000 description 22
- 238000000746 purification Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 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 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 8
- 229910017604 nitric acid Inorganic materials 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 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 5
- 239000012535 impurity Substances 0.000 description 5
- 238000004064 recycling Methods 0.000 description 5
- 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 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 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 3
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005352 clarification Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000005121 nitriding Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052925 anhydrite Inorganic materials 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- LQNUZADURLCDLV-IDEBNGHGSA-N nitrobenzene Chemical group [O-][N+](=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 LQNUZADURLCDLV-IDEBNGHGSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 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 |
|---|---|---|---|
| DE19762654649 DE2654649C2 (de) | 1976-12-02 | 1976-12-02 | Verfahren zur Herstellung von 1-Nitroanthrachinon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH632735A5 true CH632735A5 (en) | 1982-10-29 |
Family
ID=5994517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1460177A CH632735A5 (en) | 1976-12-02 | 1977-11-29 | Process for the preparation of 1-nitroanthraquinone |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH632735A5 (enExample) |
| DE (1) | DE2654649C2 (enExample) |
| FR (1) | FR2372789A1 (enExample) |
| GB (1) | GB1560129A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3329453A1 (de) * | 1983-08-16 | 1985-03-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur gewinnung von reinem 1-nitroanthrachinon |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE167699C (enExample) * | ||||
| FR2130801A5 (enExample) * | 1971-02-19 | 1972-11-10 | Pinaud Francois | |
| BE789702A (fr) * | 1971-10-07 | 1973-02-01 | Sumitomo Chemical Co | Procede de preparation de dinitroanthraquinones |
| DE2233076A1 (de) * | 1972-07-06 | 1974-01-24 | Basf Ag | Verfahren zur herstellung von reinem 1-nitroanthrachinon |
| DE2237904C3 (de) * | 1972-08-02 | 1981-02-12 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von reinem 1-Nitroanthrachinon |
| DE2461648A1 (de) * | 1974-12-27 | 1976-07-08 | Bayer Ag | Verfahren zur herstellung von reinem 1-nitro-anthrachinon |
-
1976
- 1976-12-02 DE DE19762654649 patent/DE2654649C2/de not_active Expired
-
1977
- 1977-11-29 GB GB4962077A patent/GB1560129A/en not_active Expired
- 1977-11-29 CH CH1460177A patent/CH632735A5/de not_active IP Right Cessation
- 1977-12-02 FR FR7736401A patent/FR2372789A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2372789B1 (enExample) | 1981-04-30 |
| FR2372789A1 (fr) | 1978-06-30 |
| GB1560129A (en) | 1980-01-30 |
| DE2654649C2 (de) | 1985-01-31 |
| DE2654649A1 (de) | 1978-06-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |