DE14954C - Process for the production of dyes from nitro derivatives of naphthalene - Google Patents
Process for the production of dyes from nitro derivatives of naphthaleneInfo
- Publication number
- DE14954C DE14954C DENDAT14954D DE14954DA DE14954C DE 14954 C DE14954 C DE 14954C DE NDAT14954 D DENDAT14954 D DE NDAT14954D DE 14954D A DE14954D A DE 14954DA DE 14954 C DE14954 C DE 14954C
- Authority
- DE
- Germany
- Prior art keywords
- dyes
- production
- naphthalene
- nitro derivatives
- derivatives
- 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
- 238000000034 method Methods 0.000 title description 5
- 239000000975 dye Substances 0.000 title description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title description 3
- 150000002828 nitro derivatives Chemical class 0.000 title 1
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-Chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 claims 1
- 150000002366 halogen compounds Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- 229960000583 Acetic Acid Drugs 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- ZODDGFAZWTZOSI-UHFFFAOYSA-N nitric acid;sulfuric acid Chemical compound O[N+]([O-])=O.OS(O)(=O)=O ZODDGFAZWTZOSI-UHFFFAOYSA-N 0.000 description 1
- XRMLOZSMCSUBTL-UHFFFAOYSA-N phenylazanide Chemical compound [NH-]C1=CC=CC=C1 XRMLOZSMCSUBTL-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001043 yellow dye Substances 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
- C09B51/00—Nitro or nitroso dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 22: Farbstoffe, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
Patentirt im Deutschen Reiche vom 17. December 1880 ab.Patented in the German Empire on December 17, 1880.
Das Verfahren bezweckt die Herstellung gelber Farbstoffe, die sich durch Schönheit und Aechtheit, wie auch durch leichte Application, namentlich für Seide und Wolle, auszeichnen.The purpose of the process is to produce yellow dyes that stand out for their beauty and Authenticity, as well as by light application, especially for silk and wool, are distinguished.
In den Halogenderivaten der aromatischen Kohlenwasserstoffe sind die Halogenatome bekanntlich sehr fest gebunden; sie werden aber beweglich bei der Einführung von Nitrogruppen. So beruht unser Verfahren darauf, aus Monobrom- (oder Monochlor-) Naphtalin durch energische Nitrirung die Tetranitroverbindung zu erzeugen; in letzterem Product ^C10 JT3 (JVO2J 4J3r) läfst sich das Halogenatom mit Leichtigkeit durch verschiedene Molecülreste (Hydroxyl, Amid, Phenylamid u. s. w.) ersetzen, und entstehen dabei wohlkrystallisirende Derivate, von denen wir bis jetzt die nach folgender Methode zu erhaltenden Körper als werthvolle Farbstoffe erkannt haben.In the halogen derivatives of aromatic hydrocarbons, the halogen atoms are known to be very tightly bound; however, they become flexible with the introduction of nitro groups. Our process is based on producing the tetranitro compound from monobromo- (or monochloro-) naphthalene by vigorous nitration; In the latter product ^ C 10 JT 3 (JVO 2 J 4J3r) the halogen atom can easily be replaced by various molecular residues (hydroxyl, amide, phenylamide, etc.), and in the process well-crystallizing derivatives are formed, of which we have so far obtained those that can be obtained by the following method Recognized bodies as valuable colorants.
Es werden z. B. 3 Theile Monobromnaphtalin in 12 Theile rauchender Salpetersäure vorsichtig eingetragen; nach längerer Einwirkung verdünnt man das Reactionsproduct mit vielem Wasser und wäscht die ausgeschiedenen Nitroproducte genügend mit Wasser aus. Es ist vortheilhaft, die so erhaltenen Körper mit Ligroin, Benzol, Alkohol oder ähnlichen Flüssigkeiten zu waschen, um Nebenproducte zu entfernen. Das so erzeugte Dinitroderivat des Bromnaphtalins wird in die achtfache Menge einer Mischung von gleichen Theilen englischer Schwefelsäure und rauchender Salpetersäure eingetragen und einige Zeit erwärmt. Dann wird die ganze Masse in Wasser gegossen, der Niederschlag ausgewaschen und von Wasser möglichst befreit. Man erhält ein Gemenge isomerer Tetranitromonobromnaphtaline, von denen das für unseren Zweck geeignete sich durch seine gröfsere Löslichkeit in verschiedenen Medien, z. B. Eisessig, Benzol, Essigäther, Aceton u. s. w., auszeichnet und leicht isolirt werden kann.There are z. B. 3 parts monobromonaphthalene in 12 parts fuming nitric acid carefully registered; after prolonged action, the reaction product is diluted with a great deal of water and washes the excreted nitro products sufficiently with water. It is beneficial washing the bodies obtained in this way with ligroin, benzene, alcohol or similar liquids, to remove by-products. The dinitro derivative of bromonaphthalene produced in this way is into eight times the amount of a mixture of equal parts of English sulfuric acid and fuming nitric acid entered and warmed for some time. Then the whole mass will be in Poured water, washed out the precipitate and freed from water as far as possible. You get a mixture of isomeric tetranitromonobromonaphthalenes, one of which is for our purpose suitable due to its greater solubility in various media, e.g. B. glacial acetic acid, benzene, Vinegar ether, acetone, etc., can be distinguished and easily isolated.
Die beschriebene Nitrirung, sowie auch die Reinigung der erhaltenen Producte kann in verschiedener Weise abgeändert werden.The nitration described, as well as the purification of the products obtained, can be carried out in various ways Way to be modified.
Das so erhaltene Tetranitromonobromnaphtalin wird mit warmer Sodalösung digerirt, wobei das Natriumsalz des Tetranitronaphtols entsteht, welches, durch Krystallisation gereinigt, den von uns Heliochrysin genannten Farbstoff repräsentirt. Für letztere Reaction geben wir die Gleichung:The tetranitromonobromonaphthalene thus obtained is digested with warm soda solution, with the sodium salt of tetranitronaphtol is formed which, purified by crystallization, is obtained from represents a dye called heliochrysin. For the latter reaction we give the Equation:
C10 JT3 (JVO2J ArBr ■+■ Na2 CO3 = C10 JT3 (JVO2J 4 . ONa + Na Br -+- CO2. C 10 JT 3 (JVO 2 J ArBr ■ + ■ Na 2 CO 3 = C 10 JT 3 (JVO 2 J 4. ONa + Na Br - + - CO 2 .
Die Sodalösung kann durch bekannte Agentien ersetzt und das Verfahren dementsprechend abgeändert werden; es können so auch andere Metallsalze des Tetranitronaphtols direct erhalten und als Farbstoffe verwendet oder in das Natriumsalz übergeführt werden.The soda solution can be replaced by known agents and the process can be carried out accordingly be modified; other metal salts of tetranitronaphthol can also be obtained directly in this way and used as dyes or converted to the sodium salt.
Die aus dem beschriebenen Tetranitromonobromnaphtalin durch Einwirkung von Ammoniak, Anilin und anderen substituirten Ammoniaken entstehenden Substanzen zerfallen mehr oder weniger leicht, analog den Säureamiden, und liefern dabei auch Tetranitronaphtol bezw. dessen Salze.The from the described tetranitromonobromonaphthalene by the action of ammonia, Substances produced by aniline and other substituted ammonia more or less disintegrate less easily, analogous to the acid amides, and also deliver tetranitronaphtol respectively. whose Salts.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE14954C true DE14954C (en) |
Family
ID=292010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT14954D Active DE14954C (en) | Process for the production of dyes from nitro derivatives of naphthalene |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE14954C (en) |
-
0
- DE DENDAT14954D patent/DE14954C/en active Active
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