DE71314C - Process for the preparation of ß-naphthohydroquinone thiosulfonic acid - Google Patents
Process for the preparation of ß-naphthohydroquinone thiosulfonic acidInfo
- Publication number
- DE71314C DE71314C DENDAT71314D DE71314DA DE71314C DE 71314 C DE71314 C DE 71314C DE NDAT71314 D DENDAT71314 D DE NDAT71314D DE 71314D A DE71314D A DE 71314DA DE 71314 C DE71314 C DE 71314C
- Authority
- DE
- Germany
- Prior art keywords
- naphthohydroquinone
- preparation
- acid
- thiosulfonic acid
- naphthoquinone
- 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
- 239000002253 acid Substances 0.000 title claims description 8
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 title claims description 6
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-Naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 5
- DHCDFWKWKRSZHF-UHFFFAOYSA-N Thiosulfuric acid Chemical class OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- -1 Potassium chlorine Chemical compound 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L Sodium thiosulphate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 230000003670 easy-to-clean Effects 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 230000001603 reducing Effects 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/04—Thiosulfonates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 22: Farbstoffe, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
Patentirt im Deutschen Reiche vom l. November 1892 ab.Patented in the German Empire from l. November 1892.
In der Patentschrift Nr. 70867 ist gezeigt, dafs schweflige Säure in Form ihrer sauren Salze auf ß-Naphtochinon unter Bildung einer β - Naphtohydrochinonsulfosäure einwirkt.In patent specification No. 70867 it is shown that sulphurous acid in the form of its acidic acid Salts acts on ß-naphthoquinone to form a β-naphthohydroquinone sulfonic acid.
Auch die Thioschwefelsa'ure tritt mit Leichtigkeit mit ß-Naphtochinon in Reaction, unter Bildung eines wohlcharakterisirten schwefelhaltigen Derivates des β - Naphtohydrochinons, wenn man. schwach angesäuerte Lösungen von thioschwefelsauren Salzen auf moleculare Mengen . von ß-Naphtochinon einwirken läfst.Thiosulfuric acid also reacts easily with β-naphthoquinone Formation of a well-characterized sulfur-containing derivative of β-naphthohydroquinone, if. weakly acidic solutions of thiosulfuric acid salts to molecular quantities . lets act of ß-naphthoquinone.
Zur Darstellung des neuen Körpers verfährt man z. B. fplgendermafsen:To represent the new body one proceeds z. B. fplgendermafsen:
1,6 kg in 10 1 Wasser fein vertheilten ß-Naphtochinons (1 Molecül) werden mit einer Lösung von 2,5 kg Natriumthiosulfat (1 Molecül) in 10 1 Wasser versetzt und unter gutem Umrühren 3 kg 2oproc. Essigsäure (1 Molecül) zugegeben. Das ß-Naphtochinon geht schnell in Lösung. Man filtrirt von geringen Mengen ungelöster Substanzen ab und gewinnt so eine klare, etwas bräunlich gefärbte Flüssigkeit, welche das neue Naphtohydrochinonderivat enthält. 1.6 kg ß-naphthoquinone finely divided in 10 l of water (1 Molecül) are mixed with a solution of 2.5 kg of sodium thiosulphate (1 Molecül) added in 10 1 water and 3 kg 2oproc with thorough stirring. Acetic acid (1 Molecül) was added. The ß-naphthoquinone dissolves quickly. Small amounts are filtered undissolved substances and thus gains a clear, somewhat brownish liquid, which contains the new naphthohydroquinone derivative.
Sättigt man die Lösung mit Kochsalz, so krystallisirt nach einigem Stehen das Natriumsalz der Substanz in feinen, ein wenig grau gefärbten Nadeln aus.If the solution is saturated with common salt, the sodium salt crystallizes after standing for a while the substance in fine, slightly gray colored needles.
Vortheilhafter ist es, die Säure in Form ihres schwerer löslichen und sehr schön krystallisirenden Kaliumsalzes zu isoliren, was man dadurch erreicht, dafs man die Reactionsflüssigkeit statt mit Kochsalz mit Chlorkalium versetzt. It is more advantageous to use the acid in the form of its poorly soluble and very nicely crystallizing one To isolate the potassium salt, which is achieved by adding the reaction liquid Potassium chlorine is added instead of table salt.
Das Natriumsalz der neuen Säure ist bereits in kaltem Wasser leicht löslich. Das Kaliumsalz ist in heifsem Wasser leicht, in kaltem ziemlich schwer löslich und krystallisirt beim Erkalten der heifsen concentrirten Lösung in schönen langen Nadeln oder Prismen ohne Krystallwasser aus. Durch Umkrystallisiren aus heifsem Wasser, dem man zweckmäfsig etwas schweflige Säure zusetzt, läfst es sich leicht reinigen.The sodium salt of the new acid is easily soluble in cold water. The potassium salt is easily soluble in hot water, rather sparingly soluble in cold water, and crystallizes in the case of Cooling of the hot, concentrated solution in beautiful long needles or prisms without Crystal water. By recrystallizing from hot water to which something can be expediently added If sulphurous acid is added, it is easy to clean.
Die Bestimmung des Kaliumgehaltes ergab folgendes Resultat:The determination of the potassium content gave the following result:
Berechnet für C10 H1 S2 O5 K ^^ Calculated for C 10 H 1 S 2 O 5 K ^^
./£= 12,58 pCt. 12,04 I2,07pCt../£= 12.58 pct. 12.04 I2.07 pCt.
Auf Grund ihres chemischen Verhaltens ist die Verbindung als ß-naphtohydrochiiionthiosulfosaures KaliumDue to its chemical behavior, the compound is known as ß-naphtohydrochiiionthiosulfosaures potassium
C10H5-OH (ß,) \S-S03K C 10 H 5 -OH (β,) \ S-S0 3 K
anzusprechen.to address.
Charakteristisch für dieselbe ist die intensiv rothviolette Farbe, welche ihre wässerige Lösung auf Zusatz von Alkalien annimmt. Der Körper unterscheidet sich dadurch scharf von den sonst bekannten Derivaten des ß-Naphtohydrochinons, die zumeist in wässeriger Lösung durch Alkali gelb bis braun gefärbt werden. Beim Erwärmen mit verdünnten Mineralsäuren spaltet sich schweflige Säure ab. Zinkstaub wirkt bei Gegenwart von Säuren reducirendCharacteristic of it is the intense red-violet color, which its watery solution on the addition of alkalis. The body differs sharply from them otherwise known derivatives of ß-naphthohydroquinone, mostly in aqueous solution be colored yellow to brown by alkali. When heated with dilute mineral acids sulphurous acid splits off. Zinc dust has a reducing effect in the presence of acids
unter Entwickelung von Schwefelwasserstoff ein. Salpetrige Säure färbt die wässerige Lösung intensiv gelb.with the evolution of hydrogen sulfide. Nitrous acid stains the watery one Solution intense yellow.
An Stelle von thioschwefelsauren Salzen können in obigem Beispiel selbstverständlich auch Lösungen von Schwefel in schwefligsauren Salzen verwendet werden. Instead of thiosulfuric acid salts, it goes without saying that in the above example Solutions of sulfur in sulfuric acid salts can also be used.
Die ß-naphtohydrochinonthiosulfosauren Salze zeichnen sich durch grofse Reactionsfähigkeit aus und sollen zu Farbstoffzwecken Verwendung finden.The β-naphthohydroquinone thiosulfonic acid salts are distinguished by their great reactivity and should be used for dye purposes.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE71314C true DE71314C (en) |
Family
ID=344628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT71314D Expired - Lifetime DE71314C (en) | Process for the preparation of ß-naphthohydroquinone thiosulfonic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE71314C (en) |
-
0
- DE DENDAT71314D patent/DE71314C/en not_active Expired - Lifetime
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