DE2224793C3 - Verfahren zur Herstellung von 1,5- und 1,8-Dihydroxyanthrachinonen - Google Patents
Verfahren zur Herstellung von 1,5- und 1,8-DihydroxyanthrachinonenInfo
- Publication number
- DE2224793C3 DE2224793C3 DE2224793A DE2224793A DE2224793C3 DE 2224793 C3 DE2224793 C3 DE 2224793C3 DE 2224793 A DE2224793 A DE 2224793A DE 2224793 A DE2224793 A DE 2224793A DE 2224793 C3 DE2224793 C3 DE 2224793C3
- Authority
- DE
- Germany
- Prior art keywords
- dihydroxyanthraquinone
- acetic acid
- mother liquor
- acid
- parts
- 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
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000004359 1,8-dihydroxyanthraquinones Chemical class 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 37
- QBPFLULOKWLNNW-UHFFFAOYSA-N chrysazin Chemical compound O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O QBPFLULOKWLNNW-UHFFFAOYSA-N 0.000 claims description 25
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 17
- 229960000583 acetic acid Drugs 0.000 claims description 13
- 229960001577 dantron Drugs 0.000 claims description 11
- 239000012452 mother liquor Substances 0.000 claims description 10
- JPICKYUTICNNNJ-UHFFFAOYSA-N anthrarufin Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C=CC=C2O JPICKYUTICNNNJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000012362 glacial acetic acid Substances 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 150000004351 1,5-dihydroxyanthraquinones Chemical class 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 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 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- AMKRBKSZCGCEJK-UHFFFAOYSA-N 1,2-dimethoxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(OC)C(OC)=CC=C3C(=O)C2=C1 AMKRBKSZCGCEJK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- IJNPIHLZSZCGOC-UHFFFAOYSA-N 9,10-dioxoanthracene-1,8-disulfonic acid Chemical compound O=C1C2=CC=CC(S(O)(=O)=O)=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O IJNPIHLZSZCGOC-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000004341 dihydroxyanthraquinones Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/02—Hydroxy-anthraquinones; Ethers or esters thereof
- C09B1/06—Preparation from starting materials already containing the anthracene nucleus
- C09B1/08—Dyes containing only OH-groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/10—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH768671A CH555875A (de) | 1971-05-26 | 1971-05-26 | Verfahren zur herstellung von 1,5- und 1,8-dihydroxyanthrachinonen. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2224793A1 DE2224793A1 (de) | 1972-12-07 |
| DE2224793B2 DE2224793B2 (de) | 1980-07-31 |
| DE2224793C3 true DE2224793C3 (de) | 1981-06-19 |
Family
ID=4329012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2224793A Expired DE2224793C3 (de) | 1971-05-26 | 1972-05-20 | Verfahren zur Herstellung von 1,5- und 1,8-Dihydroxyanthrachinonen |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3884943A (enExample) |
| JP (1) | JPS5647168B1 (enExample) |
| AU (1) | AU470527B2 (enExample) |
| BE (1) | BE783889A (enExample) |
| BR (1) | BR7203296D0 (enExample) |
| CA (1) | CA982123A (enExample) |
| CH (1) | CH555875A (enExample) |
| DD (1) | DD96231A5 (enExample) |
| DE (1) | DE2224793C3 (enExample) |
| ES (1) | ES403128A1 (enExample) |
| FR (1) | FR2139112B1 (enExample) |
| GB (1) | GB1388635A (enExample) |
| NL (1) | NL7206799A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH597170A5 (enExample) * | 1974-12-20 | 1978-03-31 | Ciba Geigy Ag | |
| DE2909481A1 (de) * | 1979-03-10 | 1980-09-11 | Bayer Ag | Verfahren zur herstellung von 4,5-dinitro-1,8-dihydroxyanthrachinon |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1957936A (en) * | 1932-09-14 | 1934-05-08 | Du Pont | Manufacture of amino-dihydroxy-anthraquinones |
| US2485197A (en) * | 1944-05-24 | 1949-10-18 | Ciba Ltd | Dyestuff mixtures and process of making same |
-
1971
- 1971-05-26 CH CH768671A patent/CH555875A/xx not_active IP Right Cessation
-
1972
- 1972-05-19 NL NL7206799A patent/NL7206799A/xx unknown
- 1972-05-20 DE DE2224793A patent/DE2224793C3/de not_active Expired
- 1972-05-22 US US255253A patent/US3884943A/en not_active Expired - Lifetime
- 1972-05-23 GB GB2420772A patent/GB1388635A/en not_active Expired
- 1972-05-24 JP JP5083172A patent/JPS5647168B1/ja active Pending
- 1972-05-24 BR BR3296/72A patent/BR7203296D0/pt unknown
- 1972-05-24 ES ES403128A patent/ES403128A1/es not_active Expired
- 1972-05-24 BE BE783889A patent/BE783889A/xx unknown
- 1972-05-25 AU AU42773/72A patent/AU470527B2/en not_active Expired
- 1972-05-25 DD DD163192A patent/DD96231A5/xx unknown
- 1972-05-25 CA CA142,957A patent/CA982123A/en not_active Expired
- 1972-05-26 FR FR7218827A patent/FR2139112B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2139112A1 (enExample) | 1973-01-05 |
| CA982123A (en) | 1976-01-20 |
| CH555875A (de) | 1974-11-15 |
| DE2224793A1 (de) | 1972-12-07 |
| AU4277372A (en) | 1973-11-29 |
| ES403128A1 (es) | 1975-11-01 |
| US3884943A (en) | 1975-05-20 |
| BR7203296D0 (pt) | 1973-06-14 |
| AU470527B2 (en) | 1976-03-18 |
| FR2139112B1 (enExample) | 1977-12-23 |
| GB1388635A (en) | 1975-03-26 |
| NL7206799A (enExample) | 1972-11-28 |
| DD96231A5 (enExample) | 1973-03-12 |
| DE2224793B2 (de) | 1980-07-31 |
| JPS5647168B1 (enExample) | 1981-11-07 |
| BE783889A (fr) | 1972-11-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2715626A (en) | Process of preparing dihydrocodeinone | |
| DE2224793C3 (de) | Verfahren zur Herstellung von 1,5- und 1,8-Dihydroxyanthrachinonen | |
| DE941909C (de) | Verfahren zur Herstellung von N, N'-Diaethanol-piperazin | |
| DE1493746C3 (de) | 2- (p-Aminobenzoyloxy)-3-methylnaphtho-l,4-hydrochlnon und Verfahren zu seiner Herstellung | |
| DE2730720B1 (de) | Verfahren zur Herstellung von praktisch reinem 1-Amino-8-nitro-4,5-dihydroxy-anthrachinon | |
| US2277359A (en) | Process of performing organic chemical reactions with alkali metal compounds | |
| US1929847A (en) | Production of condensation products of 1.5-dihalogen anthraquinones | |
| DE2535337C2 (de) | Verfahren zur Herstellung von 1-Amino-naphthalin-7-sulfonsäure | |
| EP0010244A1 (de) | Verfahren zur Herstellung von 4-Nitro-4'-amino-diphenylamin-2-sulfonsäure und 2-Nitro-4'-amino-diphenylamin-4-sulfonsäure | |
| DE512820C (de) | Verfahren zur Herstellung von Oxyanthrachinonderivaten, insbesondere Alizarin und seinen Derivaten | |
| EP0010525B1 (de) | Verfahren zur Herstellung von Benzanthron | |
| EP0069880B1 (de) | Cyclopentanonderivate und Verfahren zu deren Isomerisierung | |
| US2008292A (en) | Uni t e d state s pat e nt off ice | |
| AT229318B (de) | Verfahren zur Herstellung des neuen 3-Methoxy-2-sulfanilamido-pyrazins | |
| DE525654C (de) | Verfahren zur Darstellung einer o-Amino-p-Kresolcarbondaeure | |
| DE542254C (de) | Verfahren zur Konzentrierung waessriger Ameisensaeure | |
| DE872206C (de) | Verfahren zur Herstellung von Methylchlorphenoxyfettsaeuren | |
| DE750398C (de) | Verfahren zur Herstellung von 3- und 4-Oxypyridin-4- und -3-carbonsaeuren | |
| DE1643654A1 (de) | Verfahren zur Herstellung von Bicyclo[2,2,2]-oct-7-en-2,3,5,6-tetracarbonsaeure-dianhydrid | |
| EP0057665B1 (de) | Verfahren zur Herstellung von 1-Acylamino-3,4-phthaloyl-acridonen | |
| DE825548C (de) | Verfahren zur Herstellung von neuen diquartaeren Salzen von Pyrimidylaminocinnolinen | |
| DE2114356C3 (de) | Verfahren zur Herstellung von 2,3-Dihydrofluoranthen aus l,23,10b-Tetrahydrofluoranthen | |
| AT200135B (de) | Verfahren zur Herstellung von threo-ß-(p-Nitrophenyl)-serin | |
| DE1011888B (de) | Verfahren zur Herstellung von Theophyllinderivaten | |
| DE1240087B (de) | Verfahren zur Herstellung von omega-Aminododecansaeure |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |