DE65997C - Process for the preparation of a new / J-naphthylamine and / J-naphthol disulfonic acid. (C.) - Google Patents
Process for the preparation of a new / J-naphthylamine and / J-naphthol disulfonic acid. (C.)Info
- Publication number
- DE65997C DE65997C DENDAT65997D DE65997DA DE65997C DE 65997 C DE65997 C DE 65997C DE NDAT65997 D DENDAT65997 D DE NDAT65997D DE 65997D A DE65997D A DE 65997DA DE 65997 C DE65997 C DE 65997C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- disulfonic acid
- naphthylamine
- preparation
- new
- 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 22
- 238000000034 method Methods 0.000 title claims description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical class C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 150000008049 diazo compounds Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 1
- ZTDDXQAALYPKKE-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid nitric acid Chemical class C=1(C(=CC=C2C=CC=CC12)S(=O)(=O)O)S(=O)(=O)O.[N+](=O)(O)[O-] ZTDDXQAALYPKKE-UHFFFAOYSA-N 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IRJNTBGPRRZPSS-UHFFFAOYSA-N 3-nitronaphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=C([N+]([O-])=O)C=C21 IRJNTBGPRRZPSS-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000004782 1-naphthols Chemical class 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- ZJYJZEAJZXVAMF-UHFFFAOYSA-N 2-nitronaphthalene Chemical compound C1=CC=CC2=CC([N+](=O)[O-])=CC=C21 ZJYJZEAJZXVAMF-UHFFFAOYSA-N 0.000 description 1
- DOBIZWYVJFIYOV-UHFFFAOYSA-N 7-hydroxynaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(O)=CC=C21 DOBIZWYVJFIYOV-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical class [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 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 compound 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 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000101 thioether group Chemical group 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.
Während bis jetzt bei der Nitrirung der Naphtalinsulfosäuren fast durchweg beobachtet wurde (vergl. G. Schultz, Ben, Bd. XXIII, S. jj), dafs die Nitrogruppe in die α-Stellung tritt und daher auf diesem Wege nur zu a-Naphtylaminbezw. a-Naphtolderivaten zu gelangen war, wird nach dem vorliegenden Verfahren durch Nitriren eine ß-Nitronaphtalindisulfosäure erhalten.While almost all observed so far in the nitration of Naphtalinsulfosäuren (comp. G. Schultz, Ben, Vol. XXIII, p yy), that the nitro group in the α-position occurs and, therefore, in this way only a-Naphtylaminbezw. α-naphthol derivatives were obtained, a ß-nitronaphthalene disulfonic acid is obtained by nitriding in the present process.
Als Ausgangsmäterial dient die reine Naphtalindisulfosäure (1 -5). 28 kg der feingepulverten Säure werden in 90 kg Schwefelsäure vertheilt, und zu der gut gekühlten Mischung (bei ca. o°) 10 kg Sälpetersäure von 400B., gemischt mit 10 kg Schwefelsäure, hinzugegeben. Nach kurzem Stehen wird die Mischung auf Eis gegossen und nun 40 kg Soda eingetragen. Es scheidet sich das Natronsalz einer Nitronaphtalindisulfosäure ab. Dieses wird abfiltrirt und mit Salzwasser ausgewaschen. Es krystallisirt in hellgelben, fast farblosen, büschelförmig gruppirten Nadeln. Im Filtrat bleibt das leicht lösliche Natronsalz der Nitronaphtalindisulfosäure (1 -4-8). Mit dem gleichen Effect kann Potasche zur Trennung benutzt werden.The starting material is pure naphthalene disulphonic acid (1 -5). 28 kg of the finely powdered acid are distributed in 90 kg of sulfuric acid, and 10 kg of nitric acid of 40 ° C., mixed with 10 kg of sulfuric acid, are added to the well-cooled mixture (at about 0 °). After standing for a short time, the mixture is poured onto ice and 40 kg of soda are then added. The sodium salt of a nitronaphthalene disulfonic acid separates out. This is filtered off and washed out with salt water. It crystallizes in pale yellow, almost colorless, cluster-shaped needles. The easily soluble sodium salt of nitronaphthalene disulfonic acid (1 -4-8) remains in the filtrate. Potasche can be used for separation with the same effect.
Das ausgeschiedene Natron- oder Kalisalz wird mit Wasser aufgekocht und mit Hülfe von Eisen und Essigsäure oder einem anderen Reduction smittel reducirt. Das Natronsalz der neuen Naphtylämindisulfosäure löst sich in Wasser mit tiefblauer Fluorescenz. Durch verdünnte Mineralsäuren wird das saure Natronsalz abgeschieden. - Dasselbe löst sich leicht in Wird eine solche LösungThe precipitated sodium or potassium salt is boiled with water and with the help of Iron and acetic acid, or some other reducing agent, are reduced. The sodium salt of new naphthylamine disulfonic acid dissolves in water with a deep blue fluorescence. By diluted Mineral acids, the acidic sodium salt is deposited. - The same thing easily dissolves in Will such a solution
heifsem Wasser,
stark angesäuert, so krystallisirt beim Erkalten die freie Säure in concentrisch gruppirten
Prismen. Versetzt man die angesäuerte Lösung mit Nitrit, so scheidet sich die Diazoverbindung
in schwach gelblichen Nädelchen aus, die, einmal ausgefallen, in Wasser schwer löslich
sind. Wird diese Diazoverbindung mit Alkohol gekocht, so erhält man wieder die (1 · 5)-Naphtalindisulfosäure. Wird das Kalksalz
der Säure der trockenen Destillation unterworfen, so geht reichlich ß-Naphtylamin über.
Diese Thatsachen und das Verhalten der unten beschriebenen ß-Naphtoldisulfosäure führen zu
dem Schlufs, dafs die neue Säure — die mit dem Buchstaben C bezeichnet wird — folgende
Constitution besitzt:hot water,
strongly acidified, the free acid crystallizes in concentrically grouped prisms on cooling. If nitrite is added to the acidified solution, the diazo compound separates out in pale yellowish needles which, once precipitated, are sparingly soluble in water. If this diazo compound is boiled with alcohol, the (1 · 5) -naphthalene disulfonic acid is again obtained. If the lime salt of the acid is subjected to dry distillation, then abundant β-naphthylamine passes over. These facts and the behavior of the β-naphtholedisulphonic acid described below lead to the conclusion that the new acid - which is designated by the letter C - has the following constitution:
NH9 NH 9
Von ß-Naphtylamindisulfosäuren sind bisher drei bekannt, die ß-Naphtylamindisulfosäure R, F und G. Von den beiden ersteren unterscheidet sich die Säure C dadurch, dafs sie sich nicht mit Diazokörpern zu Farbstoffen vereinigen lä'fst, von der G-Säure durch die Schwerlöslichkeit ihrer Diazoverbindungen und die Töne der aus denselben abgeleiteten Azofarben. From ß-naphtylamine disulfonic acids are so far three known, the ß-naphtylamine disulfonic acid R, F and G. The acid C differs from the first two in that it is cannot combine with diazo bodies to form dyes, from the G-acid through the The poor solubility of their diazo compounds and the tones of the azo colors derived from them.
Wird die Diazoverbindung der ß-Naphtylamindisulfosäure C mit Wasser gekocht, so geht sie glatt in die ß-Naphtoldisulfosäure C (2 · 4 · 8) über. Das Natronsalz dieser neuen Säure ist leicht löslich. Das Kalksalz krys'tallisirt in derben Prismen. Die Lösungen zeigen eine rein blaue Fluorescenz. Durch Elimination der Sulfidgruppen wird β - Naphtol erhalten. Die ß-Naphtoldisulfosäure C liefert in concentrirter Lösung mit Diazoverbindungen Farbstoffe von ganz aufserordentlicher Reinheit und Echtheit. Sie steht in ihren Reactionen der ß-Naphtoly-disulfosäure nahe, mit der sie der Constitution nach verwandt ist. Die aus dem Barytsalz mit Schwefelsäure darstellbare freie Säure ist sehr leicht löslich in Wasser.Is the diazo compound of ß-naphtylamine disulfonic acid C boiled with water, it goes smoothly into the ß-naphthol disulfonic acid C (2 x 4 x 8) over. The sodium salt of this new acid is easily soluble. The lime salt krys'tallisiert in rough prisms. The solutions show a pure blue fluorescence. By eliminating the Sulfide groups, β-naphthol is obtained. The β-naphthol disulphonic acid C gives in concentrated form Solution with diazo compounds Dyes of extraordinary purity and authenticity. It stands in its reactions of the ß-naphtholydisulphonic acid close, to which it is constitutionally related. The free one that can be prepared from the barite salt with sulfuric acid Acid is very easily soluble in water.
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE65997C true DE65997C (en) |
Family
ID=339739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT65997D Expired - Lifetime DE65997C (en) | Process for the preparation of a new / J-naphthylamine and / J-naphthol disulfonic acid. (C.) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE65997C (en) |
-
0
- DE DENDAT65997D patent/DE65997C/en not_active Expired - Lifetime
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