2-Methylnaphthalin

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H302：Gesundheitsschädlich bei Verschlucken.

  H315：Verursacht Hautreizungen.

  H319：Verursacht schwere Augenreizung.

  H335：Kann die Atemwege reizen.

  H411：Giftig für Wasserorganismen, mit langfristiger Wirkung.

• Sicherheit

  P261：Einatmen von Staub vermeiden.

  P264：Nach Gebrauch gründlich waschen.

  P264：Nach Gebrauch gründlich waschen.

  P273：Freisetzung in die Umwelt vermeiden.

  P301+P312：BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.

  P302+P352：BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.

  P305+P351+P338：BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

2-Methylnaphthalene Chemische Eigenschaften,Einsatz,Produktion Methoden

• ERSCHEINUNGSBILD

  KRISTALLE

• CHEMISCHE GEFAHREN

  Zersetzung beim Erhitzen unter Bildung von beißendem Qualm und reizenden Rauchen.

• ARBEITSPLATZGRENZWERTE

  TLV: 0,5 ppm als TWA; Hautresorption; Krebskategorie A4 (nicht klassifizierbar als krebserzeugend für den Menschen); (ACGIH 2008).
  MAK nicht festgelegt.
  

• AUFNAHMEWEGE

  Aufnahme in den Körper durch Inhalation des Aerosols und durch Verschlucken.

• INHALATIONSGEFAHREN

  Nur ungenügende Angaben vorhanden über die Geschwindigkeit, mit der eine gesundheitsschädliche Konzentration in der Luft beim Verdampfen bei 20°C erreicht wird.

• WIRKUNGEN BEI KURZZEITEXPOSITION

  WIRKUNGEN BEI KURZZEITEXPOSITION:
  Die Substanz reizt die Augen.

• WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION

  Risiko der Lungenschädigung bei wiederholter oder längerer Exposition.

• LECKAGE

  Verschüttetes Material in Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste sorgfältig sammeln. An sicheren Ort bringen. NICHT in die Umwelt gelangen lassen.

• R-Sätze Betriebsanweisung:

  R22:Gesundheitsschädlich beim Verschlucken.
  R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
  R51/53:Giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
  R63:Kann das Kind im Mutterleib möglicherweise schädigen.
  R43:Sensibilisierung durch Hautkontakt möglich.
  R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
  R45:Kann Krebs erzeugen.
  R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.

• S-Sätze Betriebsanweisung:

  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.
  S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
  S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
  S24/25:Berührung mit den Augen und der Haut vermeiden.
  S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
  S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
  S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

• Aussehen Eigenschaften

  C11H10. Farblose Kristalle mit aromatischem Geruch.

• Gefahren für Mensch und Umwelt

  Gesundheitsschädlich beim Verschlucken.
  Resorption führt zu Übelkeit, Erbrechen und Narkose. Reizt die Augen, Haut und Schleimhäute.
  LD₅₀ (oral, Ratte): 1650 mg/kg.

• Schutzmaßnahmen und Verhaltensregeln

  Geeignete Schutzhandschuhe als kurzzeitiger Staubschutz.

• Verhalten im Gefahrfall

  Trocken aufnehmen. Der Entsorgung zuführen.
  Kohlendioxid, Wasser, Pulver.
  Brennbar. Mit Luft Bildung explosionsfähiger Gemische möglich.

• Erste Hilfe

  Nach Hautkontakt: Mit reichlich Wasser abwaschen.
  Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 10 Minuten ausspülen. Sofort Augenarzt hinzuziehen.
  Nach Einatmen: Frischluft.
  Nach Verschlucken: Reichlich Wasser trinken lassen. Erbrechen auslösen. Arzt hinzuziehen.
  Nach Kleidungskontakt: Kontaminierte Kleidung entfernen.
  Ersthelfer: siehe gesonderten Anschlag

• Sachgerechte Entsorgung

  Gelöst in z.B. Aceton als halogenfreie, organische Lösemittelabfälle.

• Beschreibung

  2-Methylnaphthalene is a polycyclic aromatic hydrocarbon (PAH), consisting of two-fused aromatic rings with a methyl group attached on one of the rings at the number two carbon.
  2-Methylnaphthalene is a natural component of crude oil and coal, and is found in pyrolysis and combustion products such as cigarette and wood smoke, emissions from combustion engines, asphalt, coal tar residues, and used oils (ATSDR, 1995; HSDB, 2002; Warshawsky, 2001).
  In the United States, 2-methylnaphthalene is used for making detergents, dyes, solvents, as well as vitamin K. 2-methylnapthalene is also used to make some pesticides, or as an additional ingredient in some pesticides. 2- methylnaphthalene is released into the environment when wood or fossil fuels are burned or when there are spills of products containing fossil fuels. 2-methylnaphthalene can evaporate or break down quickly in soils exposed to air or containing certain microorganisms, but it could stay a year or more under other conditions in certain sediments or soils.

• Chemische Eigenschaften

  1-Methylnaphthalene and 2-methylnaphthalene are naphthalenerelated compounds. 1-Methylnaphthalene is a clear liquid and 2- methylnaphthalene is a solid. Insoluble inwater; soluble in alcohol and ether. Combustible. both can be smelled in air and in water at very low concentrations. The taste and odor of 2-methylnaphthalene have not been described. Its presence can be detected at a concentration of 10 ppb in air and 10 ppb in water.

• Verwenden

  The main uses of methylnaphthalene are as a raw material for dyestuff dispersants and heat transfer oils, and as a solvent for agricultural chemical. It has been used as an indicator of smoke exposure in food and packaging materials.

• Verwenden

  2-methylnaphthalene are used to make other chemicals such as dyes, insecticides, Organic synthesis and resins. Pure 2-methylnaphthalene is a component used in the manufacture of vitamin K and the insecticide carbaryl (1-naphthyl-N-methylcarbamate) (HSDB, 2002).
  Methylnaphthalene (CASRN 1321-94-4) refers to a mixture of approximately two-thirds 2-methylnaphthalene and one-third 1-methylnaphthalene (CASRN 90-12-0). Methylnaphthalene is manufactured from coal tar through the extraction of heteroaromatics and phenols. Distillation of methylnaphthalene removes 1-methylnaphthalene, leaving 2-methylnaphthalene. Mixtures containing 2-methylnaphthalene are used in the formulation of alkyl-naphthalenesulfonates (used for detergents and textile wetting agents), chlorinated naphthalenes, and hydronaphthalenes (used as solvents).

• Vorbereitung Methode

  Alkylnaphthalenes are formed as pyrolysis products in cigarette smoke. Some have been identified in commercial carbon paper. They are also the major components of the C10–C13 alkylnaphthalene concentrate fraction, which distills at 400–500
  F. A C11–C12 petroleum mixture of reformates that contained about 23% alkylnaphthalenes caused skin and eye effects. The toxicity of the alkylnaphthalenes to marine species is greater than that of the alkylbenzenes (85). The toxicity and the bioaccumulation increase with molecular weight. Nocardia cultures, isolated from soil, preferentially oxidized alkylnaphthalenes when methylated in the two positions. Methylnaphthalene can occur as the 1- or 2-, the alpha or the beta isomer. 1-Naphthalene, a flammable solid, has also been identified in the wastewater of coking operations, and in textile processing plants. Methylnaphthalene is used as a component in slow-release insecticides and in mole repellents. Workplace exposures to 18–32 mg/m3 for 2-methylnaphthalene have been reported.

• Definition

  ChEBI: A methylnaphthalene carrying a methyl substituent at position 2.

• Synthesis Reference(s)

  The Journal of Organic Chemistry, 54, p. 2142, 1989 DOI: 10.1021/jo00270a024
  Synthesis, p. 1036, 1982 DOI: 10.1055/s-1982-30054
  Tetrahedron Letters, 36, p. 6051, 1995 DOI: 10.1016/0040-4039(95)01240-I

• Allgemeine Beschreibung

  White crystalline solid.

• Air & Water Reaktionen

  Insoluble in water.

• Reaktivität anzeigen

  2-Methylnaphthalene is incompatible with strong oxidizing agents. 2-Methylnaphthalene is also incompatible with peroxides and oxygen.

• Hazard

  Lower respiratory tract irritant and lungdamage. Questionable carcinogen.

• Brandgefahr

  2-Methylnaphthalene is combustible.

• Carcinogenicity

  The carcinogenic potential of 1- and 2-methyl was investigated in B6C3F1 mice. Female and male mice were given methylnaphthalene in their diets for 81 weeks. The results indicated that 1-methyl was a possible weak carcinogen in the lung of male but not female mice whereas 2-methyl did not possess unequivocal carcinogenic potential in these mice.

• Source

  Detected in distilled water-soluble fractions of No. 2 fuel oil (0.42 mg/L), jet fuel A (0.17 mg/L), diesel fuel (0.27 mg/L), military jet fuel JP-4 (0.07 mg/L) (Potter, 1996), new motor oil (0.42 to 0.66 μg/L), and used motor oil (46 to 54 μg/L) (Chen et al., 1994). Present in diesel fuel and corresponding aqueous phase (distilled water) at concentrations of 3.5 to 9.0 g/L and 180 to 340 μg/L, respectively (Lee et al., 1992). Schauer et al. (1999) reported 2-methylnaphthalene in diesel fuel at a concentration of 980 μg/g and in a diesel-powered medium-duty truck exhaust at an emission rate of 511 μg/km.
  Thomas and Delfino (1991) equilibrated contaminant-free groundwater collected from Gainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for 24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method 625. Average 2-methylnaphthalene concentrations reported in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were 256, 354, and 267 μg/L, respectively.
  California Phase II reformulated gasoline contained 2-methylnaphthalene at a concentration of 1.33 g/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were approximately 1.00 and 50.0 mg/km, respectively (Schauer et al., 2002).
  Based on laboratory analysis of 7 coal tar samples, 2-methylnaphthalene concentrations ranged from 680 to 42,000 ppm (EPRI, 1990). Detected in 1-yr aged coal tar film and bulk coal tar at concentrations of 25,000 and 26,000 mg/kg, respectively (Nelson et al., 1996). A high-temperature coal tar contained 2-methylnaphthalene at an average concentration of 1.23 wt % (McNeil, 1983).
  Lee et al. (1992a) equilibrated eight coal tars with distilled water at 25 °C. The maximum concentration of 2-methylnaphthalene observed in the aqueous phase is 1.4 mg/L.
  Detected in wood-preserving creosotes at a concentration of 3.0 wt % (Nestler, 1974).
  Typical concentration of 2-methylnaphthalene in a heavy pyrolysis oil is 7.4 wt % (Chevron Phillips, May 2003).
  An impurity identified in commercially available acenaphthene (Marciniak, 2002).
  Schauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle-phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission rates of 2-methylnaphthalene were 15.0 mg/kg of pine burned, 9.61 mg/kg of oak burned, and 5.69 mg/kg of eucalyptus burned.

• Environmental Fate

  Biological. 2-Naphthoic acid was reported as the biooxidation product of 2-methylnaphthalene by Nocardia sp. in soil using n-hexadecane as the substrate (Keck et al., 1989). Dutta et al. (1998) investigated the degradation of 2-methylnaphthalene using a bacterial strain of Sphingomonas paucimobilis grown on phenanthrene. Degradation products identified using GC-MS were 4- methylsalicylate, 2-methylnaphthoate, and 1-hydroxy-2-methylnaphthoate.
  Estimated half-lives of 2-methylnaphthalene (0.6 μg/L) from an experimental marine mesocosm during the spring (8–16 °C), summer (20–22 °C), and winter (3–7 °C) were 11, 1.0, and 13 d, respectively (Wakeham et al., 1983).
  Photolytic. Fukuda et al. (1988) studied the photodegradation of 2-methylnaphthalene and other alkylated naphthalenes in distilled water and artificial seawater using a high-pressure mercury lamp. Based upon an experimentally rate constant of 0.042/h, the photolytic half-life of 2- methylnaphthalene in water is 16.4 h.
  Phousongphouang and Arey (2002) investigated gas-phase reaction of naphthalene with OH radicals in a 7-L Teflon chamber at 25 °C and 740 mmHg containing 5% humidity. The rate constant for this reaction was 4.86 x 10^-11 cm³/molecule?sec.
  Chemical/Physical. An aqueous solution containing chlorine dioxide in the dark for 3.5 d at room temperature oxidized 2-methylnaphthalene into the following: 1-chloro-2-methylnaphthalene, 3-chloro-2-methylnaphthalene, 1,3-dichloro-2-methylnaphthalene, 3-hydroxymethylnaphthalene, 2-naphthaldehyde, 2-naphthoic acid, and 2-methyl-1,4-naphthoquinone (Taymaz et al., 1979).

• läuterung methode

  Fractionally crystallise repeatedly from its melt, then fractionally distil under reduced pressure. It has been crystallised from *benzene and dried under vacuum in an Abderhalden pistol. It can be purified via its picrate (m 114-115o) or better via the 1,3,5-trinitrobenzene complex as for 1-methylnaphthalene (above). [Beilstein 5 IV 1693.]

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