1-Naphthol Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R21/22:Gesundheitsschädlich bei Berührung mit der Haut und beim Verschlucken.
R37/38:Reizt die Atmungsorgane und die Haut.
R41:Gefahr ernster Augenschäden.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S2:Darf nicht in die Hände von Kindern gelangen.
Aussehen Eigenschaften
C10H8O; 1-Hydroxynaphtalin. Farbloser Feststoff mit charakteristischem Geruch.
Gefahren für Mensch und Umwelt
Gesundheitsschädlich bei Berührung mit der Haut und beim Verschlucken. Reizt die Atmungsorgane und die Haut. Gefahr ernster Augenschäden. Schädigt die Leber.
Nicht mit starken Oxidationsmitteln, starken Laugen, Säurehalogeniden und Anhydriden in Berührung bringen.
LD
50(oral, Ratte): 1780 mg/kg.
Schutzmaßnahmen und Verhaltensregeln
Schutzhandschuhe als kurzzeitiger Staubschutz.
Verhalten im Gefahrfall
Stäube nicht einatmen.
Trocken aufnehmen. Der Entsorgung zuführen. Nachreinigen.
Kohlendioxid, Wasser, Schaum, Pulver.
Brennbar. Im Brandfall können gefährliche Brandgase freigesetzt werden.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 15 Minuten ausspülen. Sofort Augenarzt hinzuziehen.
Nach Einatmen: Frischluft. Arzt hinzuziehen.
Nach Verschlucken: Reichlich Wasser trinken lassen. Erbrechen auslösen. Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung sofort entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Gelöst in z.B. Aceton als halogenfreie, organische Lösemittelabfälle.
Beschreibung
1-Naphthol, or α-naphthol, is a fluorescent organic compound with the formula C10H7OH. It is a white solid. It is an isomer of 2-naphthol differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols. Both isomers are soluble in simple alcohols, ethers, and chloroform. They are precursors to a variety of useful compounds. Naphthols (both 1 and 2 isomers) are used as biomarkers for livestock and humans exposed to polycyclic aromatic hydrocarbons.
α-naphtol, combined with epichlorhydrine and sodium hydroxide to form alpha-naphtyl glycidyl ether, caused sensitization in one of three workers in a chemical plant.
Chemische Eigenschaften
Pale grey to brown solid with an unpleasant phenol odour. Darkens in the presence of light. Evaporates with water vapour. Soluble in ethanol, ether, benzene, chloroform and alkali solutions, insoluble in water. Precipitates violet when exposed to ferric chloride. 1-Naphthol [90-15-3] a-naphthol, 1- naphthalenol, 1-hydroxynaphthalene, C10H8O, Mr 144.16, forms colorless prisms (from toluene) which darken on exposure to air or light. The compound is steam volatile and sublimable. 1-Naphthol is reduced by sodium in liquid ammonia to give 5,6,7,8-tetrahydro-1-naphthol and is oxidized by NaOCl – FeCl3 or I2–KI to give a violet color. It is chlorinated by phosphorus pentachloride at 150℃ to give 1-chloronaphthalene, by sulfuryl chloride to give 4- chloro-1-naphthol, or by Cl2–CH3COOH to give 2,4-dichloro-1-naphthol. Similarly bromine forms 2,4-dibromo-1-naphthol, and this reaction may be used quantitatively for titration. Nitration of 1-naphthol gives complex mixtures. The crude 2,4-dinitro derivative was used in the mid-1800s as an acid yellow dye comparable to picric acid. Sulfonation at 50℃ readily yields 1-naphthol-2,4-disulfonic acid. Nitrous acid gives mainly the 2-nitroso derivative, contaminated with the 4-nitroso isomer.
Verwenden
1-Naphthol is used as a precursor in the manufacturing of various azo dyes and pharmaceuticals such as nadolol. It is used as biomarkers. It is used in analytical chemistry as Molisch's reagent (1-naphthol dissolved in ethanol) for checking the presence of carbohydrates. It plays an essential role with sodium hypobromite to detect the presence of arginine in proteins, which is called as Sakaguchi test.
synthetische
2-Isopropylnaphthalene can be used to synthesize 1-naphthol by oxidation via the hydroperoxide (Hock synthesis).
Historically 1-naphthol was produced via caustic fusion of naphthalene-1-sulfonic acid, but this was superseded by the I.G. Farbenindustrie process involving hydrolysis of 1-naphthylamine with aqueous 22 % sulfuric acid at 200°C under pressure in a lead-lined autoclave. To obtain a purer product, Union Carbide developed a process based on catalytic oxidation of tetralin to 1-tetralol and 1-tetralone followed by dehydrogenation. The two-stage catalytic process is claimed to give an overall yield of 72% 1-naphthol, with an overall efficiency of 97%.
Application
1-Naphthol is a hydroxyl-aromatic compound. It has been used as a prooxidant to analyze its ability to induce hemolysis in a zebrafish G6PD (glucose-6-phosphate dehydrogenase) deficiency model.
Definition
ChEBI: 1-naphthol is a naphthol carrying a hydroxy group at position 1. It has a role as a genotoxin and a human xenobiotic metabolite.
Allgemeine Beschreibung
1-Naphthol, a metabolite of carbaryl and naphthanlene. It is formed by spontaneous reaction from (1R, 2S)-Naphthalene epoxide followed to form 1, 4-Dihydroxynaphthalene.
Hazard
Toxic by ingestion and skin absorption.
Kontakt-Allergie
1-Naphthol can be used in dye manufacture and is
classified as a hair dye. Combined with epichlorhydrin
and NaOH to form alpha-naphthyl glycidyl ether, it caused
sensitization in one of three workers in a chemical plant.
Sicherheitsprofil
Poison by ingestion and
intraperitoneal routes. Moderately toxic by
skin contact. An experimental teratogen.
Experimental reproductive effects. A severe
eye and skin irritant. Mutation data reported.
Ingestion of large amounts can cause
nephritis, vomiting, diarrhea, circulatory
collapse, anemia, convulsions, and death.
Can cause kidney irritation and injury to
cornea and lens of the eye. Combustible
when exposed to heat or flame. When
heated to decomposition it emits acrid
smoke and irritating fumes.
Synthese
To a 10 mL pressure vessel, aryl halide (1.00 mmol), copper (I) oxide (0.05 mol), ligand (0.05 mol), 3 M sodium hydroxide (2 mL), and organic solvent (2 mL) were added. The reaction mixture was irradiated at 160 °C for 10 min with strong stirring. The reaction mixture was allowed to cool to room temperature. The reaction mixture was filtered through a plug of celite in a fritted filter funnel and washed with ethyl acetate. The product was extracted using 30 mL of ethyl acetate for three times. The organic extract is washed three times with 10 mL water and two times with 10 mL of brine. The combined organic phases were dried over anhydrous MgSO4 and the solvent was removed under reduced pressure to afford 1-naphthol.
läuterung methode
Sublime 1-naphthol, then crystallise it from aqueous MeOH (charcoal), aqueous 25% or 50% EtOH, *C6H6, cyclohexane, heptane, CCl4 or H2O. Dry it over P2O5 in vacuo. The 4-nitrobenzoate has m 143o (from EtOH). [Shizuka et al. J Am Chem Soc 107 7816 1985, Beilstein 8 H 596, 6 IV 4208.]
1-Naphthol Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
1-Naphthyloxyessigsure
fluorescent whitening agent OM
6-Methoxy-α-methylnaphthalin-1-acetaldehyd
1-Ethenyl-1,2,3,4-tetrahydro-6-methoxy-1-naphthalenol
17-Ethinyl-3,17-dihydroxy-18-methylestra-2,5(10)-diene3-methylether
2-(1-Naphthalenyloxy)propanoic acid
Ethyl-1-naphthylether
1-Nitroso-2-naphthol
8-Hydroxy-5,7-dinitronaphthalin-2-sulfonsure
Calcium dinatriumbis[2-chlor-5-[(2-hydroxy-1-naphthyl)azo]-4-sulfonatobenzoat]
2-Ethoxynaphthalene-1-carbonyl chloride
1-(6-Hydroxy-2-naphthyl)ethan-1-on
2-BROMO-1-(6-METHOXY-2-NAPHTHALENYL)-1-PROPANONE
13-Ethyl-17-hydroxy-18,19-dinorpregn-5(10)-en-20-yn-3-one
3-Methoxy-18-methylestra-1,3,5(10),8-tetraen-17-ethylene ketal
N,N'-Di-2-naphthyl-p-phenylendiamin
[(Naphthyloxy)methyl]oxiran
N-2-Aminoethyl-1-naphthylamindihydrochlorid
Natrium-2-[(2-hydroxynaphthyl)azo]naphthalinsulfonat
4-Amino-1-naphtholhydrochlorid
Natrium-3-hydroxy-4-[(1-hydroxy-2-naphthyl)azo]-7-nitronaphthalin-1-sulfonat
ETHYL 3-(6-METHOXY-2-NAPHTHYL)-3-METHYL GLYCIDATE
METHYL 3-(6-METHOXY-2-NAPHTHYL)-3-METHYL GLYCIDATE
synthetic tanning agent No.3
1-Hydroxy-2-naphthoesure
5,8-Dihydro-1-naphthol
17-Ethinyl-17-hydroxy-18-methylestra-5(10),9(11)-dien-3-one-3-ethylene ketal
1,6-Dibrom-2-naphthol
Natrium-3-hydroxy-4-[(1-hydroxy-2-naphthyl)azo]naphthalin-1-sulfonat
Dinatrium-5-acetylamino-4-hydroxy-3-(phenylazo)naphthalin-2,7-disulfonat
2-Nitroso-1-naphthol
1,4-Naphthalindion
1,6-DIBROMO-2-METHOXYNAPHTHALENE
3-Methoxy-18-methylestra-2,5(10)dien-17-one 17-ethylene ketal
NAPROANILIDE
1-(6-Methoxy-2-naphthyl)propan-1-on
1-Naphthylchlorformiat
O-2-Naphthylchlorthioformiat
17-Ethynyl-18-methylestra-5(10),9(11)-dien-17-ol-3-one
Napropamid
