DE2152991A1 - Verfahren zur herstellung von dimethoxyanthrachinonen - Google Patents
Verfahren zur herstellung von dimethoxyanthrachinonenInfo
- Publication number
- DE2152991A1 DE2152991A1 DE19712152991 DE2152991A DE2152991A1 DE 2152991 A1 DE2152991 A1 DE 2152991A1 DE 19712152991 DE19712152991 DE 19712152991 DE 2152991 A DE2152991 A DE 2152991A DE 2152991 A1 DE2152991 A1 DE 2152991A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- dinitroanthraquinone
- potassium hydroxide
- methanol
- dimethoxyanthrachinones
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 9
- 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 claims description 5
- 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 description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QCSZITHNACKGTF-UHFFFAOYSA-N 1,8-dimethoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(OC)=C2C(=O)C2=C1C=CC=C2OC QCSZITHNACKGTF-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- AMKRBKSZCGCEJK-UHFFFAOYSA-N 1,2-dimethoxyanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C(OC)C(OC)=CC=C3C(=O)C2=C1 AMKRBKSZCGCEJK-UHFFFAOYSA-N 0.000 description 3
- -1 Hydroxymethoxy- Chemical class 0.000 description 3
- QBPFLULOKWLNNW-UHFFFAOYSA-N chrysazin Chemical compound O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O QBPFLULOKWLNNW-UHFFFAOYSA-N 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 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 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-UHFFFAOYSA-N 0.000 description 1
- PEUAYWBFWSCPHA-UHFFFAOYSA-N 1,5-dimethoxyanthracene-9,10-dione Chemical compound O=C1C2=C(OC)C=CC=C2C(=O)C2=C1C=CC=C2OC PEUAYWBFWSCPHA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- JPICKYUTICNNNJ-UHFFFAOYSA-N anthrarufin Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C=CC=C2O JPICKYUTICNNNJ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229960001577 dantron Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000010626 work up procedure 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
- C09B1/14—Dyes containing ether groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE790442D BE790442A (fr) | 1971-10-23 | Procede de production de dimethoxyanthraquinones | |
| DE19712152991 DE2152991A1 (de) | 1971-10-23 | 1971-10-23 | Verfahren zur herstellung von dimethoxyanthrachinonen |
| JP10280572A JPS4851017A (https=) | 1971-10-23 | 1972-10-16 | |
| DD16639372A DD99562A5 (https=) | 1971-10-23 | 1972-10-20 | |
| NL7214251A NL7214251A (https=) | 1971-10-23 | 1972-10-20 | |
| FR7237485A FR2156921A1 (en) | 1971-10-23 | 1972-10-23 | 1,5-/1,8-dimethoxyanthraquinones prepn - from corresp dinitro cpds, useful as dye inters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712152991 DE2152991A1 (de) | 1971-10-23 | 1971-10-23 | Verfahren zur herstellung von dimethoxyanthrachinonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2152991A1 true DE2152991A1 (de) | 1973-04-26 |
Family
ID=5823271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712152991 Pending DE2152991A1 (de) | 1971-10-23 | 1971-10-23 | Verfahren zur herstellung von dimethoxyanthrachinonen |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4851017A (https=) |
| BE (1) | BE790442A (https=) |
| DD (1) | DD99562A5 (https=) |
| DE (1) | DE2152991A1 (https=) |
| FR (1) | FR2156921A1 (https=) |
| NL (1) | NL7214251A (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0014367A1 (de) * | 1979-02-01 | 1980-08-20 | Bayer Ag | Verfahren zur Herstellung von Dimethoxyanthrachinonen |
-
0
- BE BE790442D patent/BE790442A/xx unknown
-
1971
- 1971-10-23 DE DE19712152991 patent/DE2152991A1/de active Pending
-
1972
- 1972-10-16 JP JP10280572A patent/JPS4851017A/ja active Pending
- 1972-10-20 NL NL7214251A patent/NL7214251A/xx unknown
- 1972-10-20 DD DD16639372A patent/DD99562A5/xx unknown
- 1972-10-23 FR FR7237485A patent/FR2156921A1/fr not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0014367A1 (de) * | 1979-02-01 | 1980-08-20 | Bayer Ag | Verfahren zur Herstellung von Dimethoxyanthrachinonen |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7214251A (https=) | 1973-04-25 |
| DD99562A5 (https=) | 1973-08-12 |
| FR2156921A1 (en) | 1973-06-01 |
| JPS4851017A (https=) | 1973-07-18 |
| BE790442A (fr) | 1973-04-24 |
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