DE84379C - - Google Patents
Info
- Publication number
- DE84379C DE84379C DENDAT84379D DE84379DA DE84379C DE 84379 C DE84379 C DE 84379C DE NDAT84379 D DENDAT84379 D DE NDAT84379D DE 84379D A DE84379D A DE 84379DA DE 84379 C DE84379 C DE 84379C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- mol
- water
- formaldehyde
- diamido
- 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
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- 239000002253 acid Substances 0.000 claims description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- OPUAWDUYWRUIIL-UHFFFAOYSA-N methanedisulfonic acid Chemical compound OS(=O)(=O)CS(O)(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/47—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton having at least one of the sulfo groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 12: Chemische Apparate und Processe.CLASS 12: Chemical apparatus and processes.
FARBWERKE vorm. MEISTER LUCIUS & BRÜNING in HÖCHST a. M. Verfahren zur Darstellung von Ct1 cij-Diamido-aa a.2-dinaphtylmethan-ß2 ß2-disulfosäure. FARBWERKE vorm. MASTER LUCIUS & BRÜNING in HÖCHST a. M. Method for the preparation of Ct 1 cij-Diamido-aa a. 2- dinaphthylmethane-ß 2 ß 2 -disulfonic acid.
Patentirt im Deutschen Reiche vom 30. Oktober 1894 ab.Patented in the German Empire on October 30, 1894.
Während sich Anilin und o-Toluidin mit Formaldehyd glatt und quantitativ zu Diamidodiphenylmethan bezw. Diamidoditolylmethan verbinden (Patentschriften Nr. 53937 und 55565), ist es bekanntlich bisher nicht gelungen, auf demselben Wege ein Diamidodinaphtylmethan zu erhalten. Beide Naphtylamine reagiren mit Formaldehyd in der Art, dafs sich 2 Mol.While aniline and o-toluidine with formaldehyde smoothly and quantitatively turn into diamidodiphenylmethane respectively Connect diamidoditolylmethane (patent specifications No. 53937 and 55565), it is known that it has not yet been possible to obtain a diamidodinaphthyl methane in the same way to obtain. Both naphthylamines react with formaldehyde in such a way that 2 mol.
der Basis mit 1 Mol. des Aldehyds unter Austritt von ι Mol. Wasser und von 1 Mol. Ammoniak verbinden, wobei der Methanrest CH2 stets in die Ortho - Stellung zur Amidogruppe eingreift. Die so entstehenden Körper sind als Hydroacridine der Naphtalinreihe anzusprechen :the base with 1 mol. of the aldehyde with the escape of 1 mol. of water and 1 mol. of ammonia, the methane residue CH 2 always intervening in the ortho position to the amido group. The resulting bodies are to be addressed as hydroacridines of the naphthalene series:
,CHn-, CH n -
Die a1-Naphtylamin-ß1 - monosulfosä'ure der Patentschrift Nr. 56563The a 1 -naphthylamine-β 1 -monosulfonic acid of patent specification No. 56563
NH,NH,
SO3HSO 3 H
bei welcher die Ortho - Stellung zur Amidogruppe durch die 5O3 H- Gruppe besetzt ist, liefert nun bei der Condensation mit Formaldehyd leicht und glatt die Ct1 aj-Diamido-a2 a2-dinaphtylmethan-ßj ßj-disulfosäure von der nebenstehenden Formel:in which the ortho position to the amido group is occupied by the 5O 3 H group, the condensation with formaldehyde easily and smoothly gives the Ct 1 aj-diamido-a 2 a 2- dinaphthylmethane-βj ßj-disulfonic acid of the formula opposite :
NHn NH n
-SO3H-SO 3 H
SO3HSO 3 H
NH2.NH 2 .
Beispiel: 45 kg aj-Naphtylamin-ßj-monosulfosäure werden in Form des Natronsalzes in 1000 1 siedenden Wassers gelöst, hierauf 7,5 kg Formaldehyd von 40 pCt. hinzugefügt und sofort mit etwa 30 kg Salzsäure (22 ° B.) angesäuert. Nach wenigen Minuten beginnt die Abscheidung der Diamidodinaphtylmethandisulfosäure und ist mit dem Erkalten der Flüssigkeit beendet. Die Säure wird abfiltrirt, mit Wasser gewaschen und getrocknet. Eine weitere Reinigung ist für technische Zwecke nicht erforderlich. Zum Zwecke der Darstellung analysenreiner Substanz löst man die Säure in einer verdünnten Lösung von Natriumacetat auf, filtrirt und fällt mit Salzsäure.Example: 45 kg of α-naphthylamine-β-monosulfonic acid are dissolved in 1000 liters of boiling water in the form of the sodium salt, then 7.5 kg Formaldehyde of 40 pCt. added and immediately acidified with about 30 kg of hydrochloric acid (22 ° B.). After a few minutes, the separation of the diamidodinaphthylmethanedisulfonic acid begins and is over when the liquid cools down. The acid is filtered off, washed with water and dried. One further purification is not necessary for technical purposes. For the purpose of illustration If the substance is analytically pure, the acid is dissolved in a dilute solution of sodium acetate up, filtered and precipitated with hydrochloric acid.
Die Diamidodinaphtylmethandisulfosäure krystallisirt in schwach gelblichen Nadeln mit ι Mol. Krystallwasser. Die Elementaranalyse bestätigt die Formel:The diamidodinaphthyl methanedisulfonic acid crystallizes in pale yellowish needles ι Mol. of crystalline water. The elemental analysis confirms the formula:
C21 C 21
N2 S2 O0 + H2 O. N 2 S 2 O 0 + H 2 O.
Ihre Salze sind farblos oder schwach gelblich, in Wasser gut löslich.Their salts are colorless or slightly yellowish and readily soluble in water.
Die Säure färbt sich langsam an der Luft, rasch unter der Einwirkung von Oxydationsmitteln blaugrün unter Bildung von Diamidonaphthydroldisulfosäure. - -The acid changes color slowly in the air, rapidly under the action of oxidizing agents blue-green with formation of diamidonaphthydrol disulfonic acid. - -
Sehr charakteristisch ist das Verhalten der Diamidodinaphtylmethandisulfosäure gegen salpetrige Säure. Versetzt man eine verdünnte wässerige Lösung ihres Alkalisalzes mit Natriumnitrit und säuert mit etwas Salzsäure an, so färbt sich die Lösung prachtvoll grün. Hierbei findet Diazotirung und gleichzeitige Oxydation zu Hydrol statt.The behavior of diamidodinaphtylmethanedisulphonic acid towards nitrous acid is very characteristic Acid. A dilute aqueous solution of its alkali salt is mixed with sodium nitrite and acidified with a little hydrochloric acid, the solution turns a splendid green. Here Diazotization and simultaneous oxidation to hydrol take place.
Die Diamidodinaphtylmethandisulfosäure ist unlöslich in kaltem Wasser, sehr schwer löslich in siedendem Wasser; in concentrirter Schwefelsäure löst sie sich mit grüner Fluorescenz. Diamidodinaphtylmethanedisulfonic acid is insoluble in cold water, very sparingly soluble in boiling water; in concentrated sulfuric acid it dissolves with green fluorescence.
Die neue Verbindung soll Verwendung finden zur Darstellung von Farbstoffen.The new compound is to be used for the representation of dyes.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE84379C true DE84379C (en) |
Family
ID=356608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT84379D Active DE84379C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE84379C (en) |
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0
- DE DENDAT84379D patent/DE84379C/de active Active
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