DE162792C - - Google Patents
Info
- Publication number
- DE162792C DE162792C DE1904162792D DE162792DA DE162792C DE 162792 C DE162792 C DE 162792C DE 1904162792 D DE1904162792 D DE 1904162792D DE 162792D A DE162792D A DE 162792DA DE 162792 C DE162792 C DE 162792C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- erythrooxyanthraquinone
- sulfuric acid
- quinizarin
- heated
- 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 - Lifetime
Links
- GUEIZVNYDFNHJU-UHFFFAOYSA-N 1,4-Dihydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004327 boric acid Substances 0.000 claims description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N Nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In der Patentschrift 97674 ist angegeben, daß durch Oxydation von Erythrooxyanthrachinon
mit rauchender Schwefelsäure das ι »5-Dioxyanthrachinon (Anthrarufin) entsteht.
Es wurde nun die überraschende Beobachtung gemacht, daß man zu einem ganz anderen
Ergebnis, nämlich zu dem I · 4-Dioxyanthrachinon (Chinizarin) gelangt, wenn manErythrooxyanthrachinon
in schwefelsaurer Lösung mit salpetriger Säure oxydiert. Da in das
Anthrachinon bei gleicher Behandlung zwei Hydroxylgruppen eintreten (vergl. Patent
81245), so war auch im vorliegenden Falle
in erster Linie ein analoges Ergebnis unter Bildung von 1 · 4 · 5-Trioxyanthrachinon zu
erwarten, während in Wirklichkeit aber in sehr glatter Weise Chinizarin entsteht. Bei
der Ausführung dieses Verfahrens arbeitet man zweckmäßig unter Zusatz von Borsäure,
da dann die Ausbeute an reinem Chinizarin eine bessere ist.
Beispiel. In eine Lösung von 20kgNatriumnitrit in 600 kg Schwefelsäure von 660Be. werden
30 kg Borsäure und dann 30 kg Erythrooxyanthrachinon eingetragen. Man erhitzt nun auf 180 bis 2000, bis die spektroskopische
Prüfung keine weitere Zunahme an gebildetem Chinizarin mehr erkennen läßt. Man läßt
hierauf erkalten, verdünnt die Schmelze mit Wasser, erhitzt zum Kochen und filtriert das
abgeschiedene Chinizarin ab.Patent specification 97674 states that the ι »5-dioxyanthraquinone (anthrarufin) is formed by oxidation of erythrooxyanthraquinone with fuming sulfuric acid. The surprising observation has now been made that a completely different result, namely I · 4-dioxyanthraquinone (quinizarine), is obtained if erythrooxyanthraquinone is oxidized in sulfuric acid solution with nitrous acid. A similar result to form 1 x 4 x 5-Trioxyanthrachinon in the anthraquinone with the same treatment as two hydroxyl groups occur (see FIG. Patent 81245), as was to be expected also in the present case in the first place, while in reality, however, in a very smooth manner Chinizarin arises. When carrying out this process, it is advisable to work with the addition of boric acid, since the yield of pure quinizarin is then better.
Example. In a solution of 20 kg sodium nitrite in 600 kg sulfuric acid of 66 0 Be. 30 kg of boric acid and then 30 kg of erythrooxyanthraquinone are entered. The mixture is then heated to 180 to 200 ° until the spectroscopic examination reveals no further increase in quinizarine formed. It is then allowed to cool, the melt is diluted with water, heated to the boil and the quinizarin which has separated out is filtered off.
Statt Natriumnitrit können in obigem Beispiel auch andere Nitrite oder salpetrige Säure oder deren Verbindungen, wie z. B. Nitrosylschwefelsäure, verwendet werden.In the above example, instead of sodium nitrite, other nitrites or nitrous Acid or its compounds, such as. B. nitrosylsulfuric acid can be used.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT26859D AT26859B (en) | 1904-03-02 | 1905-07-17 | Process for the preparation of quinizarin. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE162792C true DE162792C (en) |
Family
ID=428551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1904162792D Expired - Lifetime DE162792C (en) | 1904-03-02 | 1904-03-02 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE162792C (en) |
-
1904
- 1904-03-02 DE DE1904162792D patent/DE162792C/de not_active Expired - Lifetime
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