DE2253276C2 - Verfahren zur Herstellung von reinem 1-Nitroanthrachinon - Google Patents
Verfahren zur Herstellung von reinem 1-NitroanthrachinonInfo
- Publication number
- DE2253276C2 DE2253276C2 DE2253276A DE2253276A DE2253276C2 DE 2253276 C2 DE2253276 C2 DE 2253276C2 DE 2253276 A DE2253276 A DE 2253276A DE 2253276 A DE2253276 A DE 2253276A DE 2253276 C2 DE2253276 C2 DE 2253276C2
- Authority
- DE
- Germany
- Prior art keywords
- nitroanthraquinone
- parts
- pure
- ketone
- instead
- 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
- 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 27
- 238000000034 method Methods 0.000 title claims description 14
- 239000000203 mixture Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000003999 initiator Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 18
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- HIGGFWFRAWSMBR-UHFFFAOYSA-N 2-Methyl-3-hexanone Chemical compound CCCC(=O)C(C)C HIGGFWFRAWSMBR-UHFFFAOYSA-N 0.000 description 6
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- -1 d-butyl ketone Chemical compound 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 3
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- HYTRYEXINDDXJK-UHFFFAOYSA-N Ethyl isopropyl ketone Chemical compound CCC(=O)C(C)C HYTRYEXINDDXJK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KSZVHVUMUSIKTC-UHFFFAOYSA-N acetic acid;propan-2-one Chemical compound CC(C)=O.CC(O)=O KSZVHVUMUSIKTC-UHFFFAOYSA-N 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 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 description 1
- 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 1
- 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 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- 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 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- YWXLSHOWXZUMSR-UHFFFAOYSA-N octan-4-one Chemical compound CCCCC(=O)CCC YWXLSHOWXZUMSR-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2253276A DE2253276C2 (de) | 1972-10-31 | 1972-10-31 | Verfahren zur Herstellung von reinem 1-Nitroanthrachinon |
| FR7327384A FR2213267A1 (en) | 1972-08-02 | 1973-07-26 | Pure 1-nitro anthraquinone from mixts with dinitro anthraquinones - by selectively solubilising them in organic solvents with catalyst and base |
| PL16442073A PL89446B1 (enExample) | 1972-08-02 | 1973-07-31 | |
| SU1955920A SU544365A3 (ru) | 1972-08-02 | 1973-07-31 | Способ выделени 1-нитроантрахинона |
| DD17266173A DD108738A5 (enExample) | 1972-08-02 | 1973-08-01 | |
| IT5177573A IT990108B (it) | 1972-08-02 | 1973-08-01 | Procedimento per la produzione di i nitroantrachinone pur |
| AU61740/73A AU6174073A (en) | 1972-10-31 | 1973-10-24 | Pure 1-nitroanthraquinone |
| CH1509173A CH613685A5 (enExample) | 1972-10-31 | 1973-10-26 | |
| US410367A US3904659A (en) | 1972-10-31 | 1973-10-29 | Production of pure 1-nitroanthraquinone |
| GB5032973A GB1442670A (en) | 1972-10-31 | 1973-10-30 | Production of pure 1-nitroanthraquinone |
| JP48121841A JPS4976853A (enExample) | 1972-10-31 | 1973-10-31 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2253276A DE2253276C2 (de) | 1972-10-31 | 1972-10-31 | Verfahren zur Herstellung von reinem 1-Nitroanthrachinon |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2253276A1 DE2253276A1 (de) | 1974-05-09 |
| DE2253276C2 true DE2253276C2 (de) | 1981-11-26 |
Family
ID=5860467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2253276A Expired DE2253276C2 (de) | 1972-08-02 | 1972-10-31 | Verfahren zur Herstellung von reinem 1-Nitroanthrachinon |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3904659A (enExample) |
| JP (1) | JPS4976853A (enExample) |
| AU (1) | AU6174073A (enExample) |
| CH (1) | CH613685A5 (enExample) |
| DE (1) | DE2253276C2 (enExample) |
| GB (1) | GB1442670A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2552560A1 (de) * | 1974-12-05 | 1976-06-10 | Sandoz Ag | Verfahren zum reinigen von l-nitroanthrachinon |
| CN101391963B (zh) * | 2008-10-15 | 2012-04-25 | 山东大学 | 一种对1-硝基蒽醌废渣综合利用的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2039822B2 (de) * | 1970-08-11 | 1974-12-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 1-Nitroanthrachinon |
-
1972
- 1972-10-31 DE DE2253276A patent/DE2253276C2/de not_active Expired
-
1973
- 1973-10-24 AU AU61740/73A patent/AU6174073A/en not_active Expired
- 1973-10-26 CH CH1509173A patent/CH613685A5/xx not_active IP Right Cessation
- 1973-10-29 US US410367A patent/US3904659A/en not_active Expired - Lifetime
- 1973-10-30 GB GB5032973A patent/GB1442670A/en not_active Expired
- 1973-10-31 JP JP48121841A patent/JPS4976853A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US3904659A (en) | 1975-09-09 |
| CH613685A5 (enExample) | 1979-10-15 |
| JPS4976853A (enExample) | 1974-07-24 |
| DE2253276A1 (de) | 1974-05-09 |
| AU6174073A (en) | 1975-04-24 |
| GB1442670A (en) | 1976-07-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3633033A1 (de) | Verfahren und katalysatorsystem zur trimerisierung von acetylen und acetylenverbindungen | |
| DE1670043B2 (de) | Verfahren zur Herstellung von 3-(Aminophenyl)-pyridazon-(6)-derivaten | |
| DE2149159A1 (de) | Verfahren zur Herstellung von Trimethylhydrochinon | |
| DE2253276C2 (de) | Verfahren zur Herstellung von reinem 1-Nitroanthrachinon | |
| DE1237567B (de) | Verfahren zur Herstellung von delta 5-6-Methylsteroiden | |
| EP0010656B1 (de) | Verfahren zur Herstellung von 4-Acyloxy-2-methyl-crotonaldehyden | |
| DE1793693C3 (enExample) | ||
| DE3203487A1 (de) | Verfahren zur herstellung von tocopherylacetat oder tocopherylpropionat | |
| DE2453365A1 (de) | Verfahren zur herstellung von n-trimethylsilylacetamid | |
| DE4336154A1 (de) | Verfahren zur Herstellung von L-5-(2-Acetoxy-propionyl-amino)-2,4,6-trijod-isophthalsäure-bis-1,3-dihydroxy-polyamid) | |
| DE739438C (de) | Verfahren zur Herstellung von Anlagerungsprodukten | |
| DE836352C (de) | Verfahren zur Herstellung von Oxazolidin-2, 4-dion-abkoemmlingen | |
| DE814740C (de) | Verfahren zur Gewinnung von cis-cis-Muconsaeure und ihren Homologen | |
| DE724757C (de) | Verfahren zur Herstellung von Diazoketonen | |
| DE875804C (de) | Verfahren zur Herstellung von Umwandlungsprodukten des Pentaerythrit-dichlorhydrin-monoschwefligsaeureesters | |
| DE962333C (de) | Verfahren zur Herstellung von Cyclohexanonoxim | |
| DE912211C (de) | Verfahren zur Herstellung von ª‡-Acylacetessigestern | |
| DE931651C (de) | Verfahren zur Herstellung von d, 1-4-Thiazolidon-2-capronsaeure oder deren Estern | |
| DE2105010C (enExample) | ||
| DE915938C (de) | Verfahren zur Herstellung von Oxoacylaminen der Cyclopentanopolyhydrophenanthrenreihe | |
| DE1076681B (de) | Verfahren zur Herstellung von Vitamin A-aldehyd | |
| AT242690B (de) | Verfahren zur Herstellung von Derivaten des 2,3-Dimethoxy-5-methyl-benzohydrochinons-(1,4) und den zugehörigen Chinonen | |
| DE1793661C (de) | Verfahren zur Herstellung von 2,5-Dimethyl-4,5-dihydrofuranol-(3)-on-(4). Ausscheidung aus: 1768649 | |
| AT251767B (de) | Verfahren zur Herstellung von neuen Estern der Ascorbinsäure mit höheren ungesättigten Fettsäuren | |
| DE2833967A1 (de) | Verfahren zur herstellung von apovincamin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8330 | Complete renunciation |