CH212802A - Process for the preparation of a nitrogen-containing 5.6.7.8-tetrahydroanthraquinone derivative. - Google Patents
Process for the preparation of a nitrogen-containing 5.6.7.8-tetrahydroanthraquinone derivative.Info
- Publication number
- CH212802A CH212802A CH212802DA CH212802A CH 212802 A CH212802 A CH 212802A CH 212802D A CH212802D A CH 212802DA CH 212802 A CH212802 A CH 212802A
- Authority
- CH
- Switzerland
- Prior art keywords
- tetrahydroanthraquinone
- nitrogen
- derivative
- preparation
- leuco
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 229910000906 Bronze Inorganic materials 0.000 claims description 3
- 239000010974 bronze Substances 0.000 claims description 3
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical group COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001590 oxidative effect Effects 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
- C09B1/30—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups sulfonated
-
- 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
-
- 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
-
- 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines sticlzstofhaltigen 5.6.7.8-Tetrahydro- anthrachinonderivates. Gegenstand dieses Zusatzpatentes ist ein Verfahren zur Herstellung eines stickstoff haltigen 5.6.7.8-Tetrahydroanthrachinon- derivates, welches darin besteht, dass man Leuko-5.6.7.8-tetrahydrochinizarin mit Äthylamin umsetzt und die Leukoverbin- dung oxydiert.
Die so erhaltene neue Verbindung bil det derbe, bronzeglänzende Kristalle vom Schmelzpunkt 145 bis 146 C. Die Lösungs farbe in konzentrierter Schwefelsäure ist blaustichig rot, in organischen Lösungsmit teln rein blau. Die Verbindung färbt Ace- tatseide in blauen Tönen.
<I>Beispiel:</I> Man erhitzt ein Gemisch von 26 Ge wichtsteilen Leuko-5 . 6 . 7.8-tetrahydrochin- izarin, 160 Gewichtsteilen Äthylalkohol und 80 Gewichtsteilen einer 50 % ixen wässrigen Äthylaminlösung 4 bis 5 Stunden zum Sie den. Dann leitet man 2 Stunden Luft durch die Lösung. Das 1 . 4-Di-(äthylamino)- 5.6.7.8-tetrahydroanthrachinon scheidet sich in deren bronzeglänzenden Kristallen schon in der Hitze aus.
Es hat einen Schmelzpunkt von 145 bis 146 C; die Lö sungsfarbe in konzentrierter Schwefelsäure ist blaustichig rot, in organischen Lösungs mitteln rein blau. Auf Acetatseide erhält man eine blaue Färbung.
Process for the production of a nitrogen-containing 5.6.7.8-tetrahydro-anthraquinone derivative. The subject of this additional patent is a process for the production of a nitrogen-containing 5.6.7.8-tetrahydroanthraquinone derivative, which consists in reacting leuco-5.6.7.8-tetrahydroquinizarine with ethylamine and oxidizing the leuco compound.
The new compound obtained in this way forms tough, shiny bronze crystals with a melting point of 145 to 146 C. The solution color in concentrated sulfuric acid is bluish red, in organic solvents it is pure blue. The connection dyes acetate silk in blue tones.
<I> Example: </I> A mixture of 26 parts by weight of Leuko-5 is heated. 6th 7.8-tetrahydroquinizarin, 160 parts by weight of ethyl alcohol and 80 parts by weight of a 50% ixen aqueous ethylamine solution for 4 to 5 hours. Then air is passed through the solution for 2 hours. The 1st 4-Di- (äthylamino) - 5.6.7.8-tetrahydroanthraquinone separates in their shiny bronze crystals in the heat.
It has a melting point of 145 to 146 C; the solution color in concentrated sulfuric acid is bluish red, in organic solvents it is pure blue. A blue coloration is obtained on acetate silk.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE212802X | 1937-12-24 | ||
| DE150138X | 1938-01-15 | ||
| CH210607T | 1938-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH212802A true CH212802A (en) | 1940-12-15 |
Family
ID=27177899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH212802D CH212802A (en) | 1937-12-24 | 1938-12-17 | Process for the preparation of a nitrogen-containing 5.6.7.8-tetrahydroanthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH212802A (en) |
-
1938
- 1938-12-17 CH CH212802D patent/CH212802A/en unknown
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