DE99759C - - Google Patents
Info
- Publication number
- DE99759C DE99759C DENDAT99759D DE99759DA DE99759C DE 99759 C DE99759 C DE 99759C DE NDAT99759 D DENDAT99759 D DE NDAT99759D DE 99759D A DE99759D A DE 99759DA DE 99759 C DE99759 C DE 99759C
- Authority
- DE
- Germany
- Prior art keywords
- oxy
- naphthoquinone
- acid
- sulfonic acid
- water
- 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.)
- Active
Links
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-Naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims 1
- 235000013601 eggs Nutrition 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 238000005987 sulfurization reaction Methods 0.000 description 2
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Color Printing (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Sulfosäuren des ß-Oxy-ct-naphtochinons sind seither noch nicht durch Sulfuriren des ß-Oxynaphtochinons dargestellt worden, sondern der einzige Repräsentant dieser Körperklasse, eine β - Oxy - α -naphtochinonmonosulfosäure, < wurde auf dem Umwege über das Dichlornaphtochinon dargestellt (Beilstein, III. Auflage, Bd. Ill, S. 388). Dieses umständliche Herstellungsverfahren stand einer Verwerthung der von Grabe hergestellten Säure im Wege, und so ist auch über die Möglichkeit, diese Säure den Zwecken der Farbstoffdarstellung dienstbar zu machen, nichts bekannt geworden.Are sulfonic acids of ß-oxy-ct-naphthoquinone not since then by sulfurizing the ß-oxynaphthoquinone but the only representative of this body class, a β-oxy-α-naphthoquinone monosulfonic acid, < was represented by a detour via the dichloronaphthoquinone (Beilstein, 3rd edition, Vol. Ill, p. 388). This cumbersome manufacturing process was an exploitation of the acid produced by grave in the way, and so is also about the possibility of this acid to make it available for the purposes of dye representation, nothing has become known.
Es wurde nun gefunden, dafs sich das ß-Oxy-ct-naphtochinon bei Einwirkung sulfurirender Mittel aufserordentlich leicht in' eine Sulfosäure überführen läfst. Da auch das ß-Oxy- a - naphtochinon selbst neuerdings sehr leicht zugänglich geworden ist, so kommt zu dieser leichten und einfachen Darstellungsweise der β - Oxy - α - naphtochinonsulfosäure noch die Möglichkeit, die erhaltene Sulfosäure mit Vortheil zur Herstellung von Farbstoffen anzuwenden, wozu sie sich nach den bisherigen Versuchen in hervorragendem Mafse eignet.It has now been found that the β-oxy-ct-naphthoquinone can be converted into a sulphonic acid with extraordinary ease on the action of sulphurizing agents. Since the β-oxy- a -naphthoquinone itself has recently become very easily accessible, in addition to this easy and simple method of representation of the β-oxy-α-naphthoquinone sulfonic acid, there is also the possibility of using the sulfonic acid obtained with advantage for the production of dyes, including according to the experiments so far, it is outstandingly suitable.
Das Verfahren zur Herstellung dieser Sulfosäure, welcher voraussichtlich die folgende ConstitutionThe process for the preparation of this sulfonic acid, which is expected to be the following Constitution
OHOH
SO» HSO »H
zukommt, wird durch nachstehendes Beispiel erläutert:is explained by the following example:
50 kg ß-Oxy-a-naphtochinon werden bei einer Temperatur von 15 bis 200 in 250 kg rauchende Schwefelsäure (25 pCt. Anhydridgehalt) eingetragen, das Gemisch wird hierauf etwa 2 Stunden bei einer Temperatur von 20 ° sich selbst überlassen. Sobald die Sulfurirung beendet, d. h. eine Probe des Sulfurirungsgemisches in Wasser klar löslich ist, giefst man das Reactionsproduct auf Eis und scheidet durch Zusatz von Kochsalzlösung die gebildete Sulfosäure in Form ihres Natronsalzes aus.50 kg ß-oxy-a-naphthoquinone be at a temperature of 15 to 20 0 to 250 kg fuming sulfuric acid (25 per cent. Anhydride content) was added, the mixture is then left to be about 2 hours at a temperature of 20 ° themselves. As soon as the sulfurization has ended, ie a sample of the sulfurization mixture is clearly soluble in water, the reaction product is poured onto ice and the sulfonic acid formed is separated out in the form of its sodium salt by adding sodium chloride solution.
Dies Salz bildet aus Wasser umkrystallisirt glänzende, schwach gelblich gefärbte Blättchen; es ist in kochendem Wasser leicht, in kaltem ■Wasser dagegen schwer löslich. Auf Zusatz von Natronlauge zur kalten wässerigen Lösung scheidet sich ein Dinatriumsalz in gelben Krystallen aus.From water this salt forms shiny, pale yellowish-colored leaves in crystallized form; it is easily soluble in boiling water, but poorly ■ soluble in cold water. On addition From sodium hydroxide solution to cold aqueous solution, a disodium salt separates in yellow crystals the end.
Die angegebenen Mengen und Concentrationsverhältnisse der Schwefelsäure können in weiten Grenzen variirt werden, und je nachdem wird auch die Temperatur, sowie die Zeitdauer eine entsprechende Variation erfahren müssen.The specified amounts and concentration ratios of the sulfuric acid can be found in can be varied within wide limits, and depending on this, the temperature, as well as the Duration must experience a corresponding variation.
Die vorstehend beschriebene Sulfosäure des β - Oxy - a - naphtochinons soll zur Herstellung von ■ Farbstoffen auf dem Wege der Condensation mit Hydrazinen oder Orthodiamidoverbindungen etc. dienen.The above-described sulfonic acid of β-oxy- a- naphthoquinone is intended to be used for the production of dyes by way of condensation with hydrazines or orthodiamido compounds, etc.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE99759C true DE99759C (en) |
Family
ID=370613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT99759D Active DE99759C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE99759C (en) |
-
0
- DE DENDAT99759D patent/DE99759C/de active Active
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