Naphthalin

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H228：Entzündbarer Feststoff.

  H302：Gesundheitsschädlich bei Verschlucken.

  H351：Kann vermutlich Krebs verursachen.

  H410：Sehr giftig für Wasserorganismen mit langfristiger Wirkung.

• Sicherheit

  P202：Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.

  P210：Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.

  P240：Behälter und zu befüllende Anlage erden.

  P273：Freisetzung in die Umwelt vermeiden.

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

  P308+P313：BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

Naphthalene Chemische Eigenschaften,Einsatz,Produktion Methoden

• ERSCHEINUNGSBILD

  WEISSER FESTSTOFF IN VERSCHIEDENEN FORMEN MIT CHARAKTERISTISCHEM GERUCH.

• PHYSIKALISCHE GEFAHREN

  Staubexplosion der pulverisierten oder granulierten Substanz in Gemischen mit Luft möglich.

• CHEMISCHE GEFAHREN

  Beim Verbrennen Bildung reizender und giftiger Gase. Reagiert mit starken Oxidationsmitteln.

• ARBEITSPLATZGRENZWERTE

  TLV: 10 ppm (als TWA); 15 ppm (als STEL); Hautresorption; Krebskategorie A4 (nicht klassifizierbar als krebserzeugend für den Menschen); (ACGIH 2005).
  MAK: Hautresorption; Krebserzeugend Kategorie 2; Keimzellmutagen Kategorie 3B; (DFG 2005).
  

• AUFNAHMEWEGE

  Aufnahme in den Körper durch Inhalation, über die Haut und durch Verschlucken.

• INHALATIONSGEFAHREN

  Beim Verdampfen bei 20°C tritt langsam eine gesundheitsschädliche Kontamination der Luft ein. (S. Anm.)

• WIRKUNGEN BEI KURZZEITEXPOSITION

  WIRKUNGEN BEI KURZZEITEXPOSITION:
  Möglich sind Auswirkungen auf das Blut mit nachfolgenden Blutzellschädigungen (Hämolyse) (s.Anm.). Die Auswirkungen treten u.U. verzögert ein. Exposition durch Verschlucken kann zum Tod führen. ärztliche Beobachtung notwendig.

• WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION

  Möglich sind Auswirkungen auf das Blut mit nachfolgender chronischer hämolytischer Anämie (Blutarmut). Möglich sind Auswirkungen auf die Augen mit nachfolgender Linsentrübung. Möglicherweise krebserzeugend für den Menschen.

• LECKAGE

  Persönliche Schutzausrüstung: Atemschutzfilter für organische Gase und Dämpfe. NICHT in die Umwelt gelangen lassen. Verschüttetes Material in abgedeckten Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste sorgfältig sammeln. An sicheren Ort bringen.

• R-Sätze Betriebsanweisung:

  R22:Gesundheitsschädlich beim Verschlucken.
  R40:Verdacht auf krebserzeugende Wirkung.
  R50/53:Sehr giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
  R67:Dämpfe können Schläfrigkeit und Benommenheit verursachen.
  R65:Gesundheitsschädlich: kann beim Verschlucken Lungenschäden verursachen.
  R38:Reizt die Haut.
  R11:Leichtentzündlich.
  R39/23/24/25:Giftig: ernste Gefahr irreversiblen Schadens durch Einatmen, Berührung mit der Haut und durch Verschlucken.
  R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
  R52/53:Schädlich für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.

• S-Sätze Betriebsanweisung:

  S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
  S46:Bei Verschlucken sofort ärztlichen Rat einholen und Verpackung oder Etikett vorzeigen.
  S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
  S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
  S62:Bei Verschlucken kein Erbrechen herbeiführen. Sofort ärztlichen Rat einholen und Verpackung oder dieses Etikett vorzeigen.
  S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
  S16:Von Zündquellen fernhalten - Nicht rauchen.
  S7:Behälter dicht geschlossen halten.

• Aussehen Eigenschaften

  C10H8; weißer, charakteristisch riechender Feststoff.

• Gefahren für Mensch und Umwelt

  Naphthalin verdampft bereits merklich bei Raumtemperatur. Die am Schmelzpunkt entweichenden Dämpfe bilden mit Luft ein zündfähiges Gemisch. Mit starken Oxidationsmitteln (z.B. Chromtrioxid) erfolgen heftige Reaktionen, der Kontakt mit Distickstoffpentoxid führt zur Explosion.
  Dämpfe und Stäube reizen Augen und Atemwege. Einatmen der Dämpfe kann zu Kopfschmerzen und Übelkeit führen. Bei häufigem Kontakt sind Hautentzündungen möglich. Einige Personen sind hypersensitiv gegenüber Naphthalin und reagieren auf geringen Hautkontakt mit schwerer Hautentzündung.
  Wassergefährdendr Stoff (WGK 2).

• Schutzmaßnahmen und Verhaltensregeln

  Im Abzug arbeiten.
  Schutzhandschuhe nur als kurzzeitiger Staub- und Spritzschutz.

• Verhalten im Gefahrfall

  Nach Verschütten oder Auslaufen erstarren lassen, mechanisch entfernen. Als Sondermüll entsorgen.
  Wasser, Kohlendioxid, Trockenlöschmittel, Schaum.

• Erste Hilfe

  Nach Hautkontakt: Mit viel Wasser und Seife abwqaschen. Erstarrte Kruste nur vom Arzt entfernen lassen!
  Nach Augenkontakt: Mit viel Wasser mind. 10 Min. bei geöffnetem Lidspalt spülen. Augenarzt konsultieren.
  Nach Einatmen: Frischluft.
  Nach Verschlucken: Viel Wasser trinken. Erbrechen auslösen. Arzt hizuziehen.
  Nach Kleidungskontakt: Kontaminierte Kleidung sofort ausziehen.
  Ersthelfer: siehe gesonderten Anschlag

• Sachgerechte Entsorgung

  Als Sondermüll entsorgen.

• Beschreibung

  Naphthalene occurs as transparent prismatic plates also available as white scales, powder balls, or cakes with a characteristic mothball or strong coal tar and aromatic odour. It is sparingly soluble in water but soluble in methanol/ethanol and very soluble in ether. Naphthalene is a commercially important aromatic hydrocarbon. Naphthalene occurs as a white solid or powder. Naphthalene occurs in coal tar in large quantities and is easily isolated from this source in pure condition. It volatilises and sublimes at room temperature above the melting point. The primary use for naphthalene is in the production of phthalic anhydride, also of carbamate insecticides, surface active agents and resins, as a dye intermediate, as a synthetic tanning agent, as a moth repellent, and in miscellaneous organic chemicals. Naphthalene is used in the production of phthalic anhydride; it is also used in mothballs. Naphthalene is also used in the manufacture of phthalic and anthranilic acids to make indigo, indanthrene, and triphenyl methane dyes, for synthetic resins, lubricant, celluloid, lampblack, smokeless powder, and hydronaphthalenes. Naphthalene is also used in dusting powders, lavatory deodorant discs, wood preservatives, fungicide, and as an insecticide. It has been used as an intestinal antiseptic and vermicide and in the treatment of pediculosis and scabies.

• Chemische Eigenschaften

  Naphthalene is a colorless to brown crystalline solid with a characteristic “moth ball” odor. It evaporates easily and has a strong odor of tar or mothballs. Solubility in water is low (31.7 mg/l at 25 °C), and it is soluble in benzene, alcohol, ether, and acetone (ATSDR, 2005). Shipped as a molten solid.

• History

  In 1819, naphthalene was obtained as white crystals during the pyrolysis of coal tar by John Kidd (1775–1851), a British physician and chemist, and Alexander Garden (1757–1829), an American living in Britain. Kidd described the properties of the white crystals he obtained from coal tar and proposed the named naphthaline for the substance; naphthaline was derived from naphtha, a general term for a volatile, fl ammable, hydrocarbon liquid. Michael Faraday (1791–1867) determined the correct empirical formula for naphthalene in 1825, and Richard August Carl Emil Erlenmeyer (1825–1909) proposed the fused benzene ring structure in 1866.

• Verwenden

  In addition to oxidation and reduction reactions, naphthalene readily undergoes substitutionreactions such as nitration, halogenation, sulfonation, and acylation to produce a varietyof other substances, which are used in the manufacture of dyes, insecticides, organic solvents,and synthetic resins. The principal use of naphthalene is for the production of phthalic anhydride,C8H4O3.
  Naphthalene is catalytically oxidized to phthalic anhydride: 2C10H8 + 9O2 → 2C4H8O3 +4CO2 + 4H2O using metal oxide catalysts. Phthalic anhydride is used to produce plastics,phthalate plasticizers, insecticides, pharmaceuticals, and resins. Sulfonation of naphthalene withsulfuric acid produces naphthalenesulfonic acids, which are used to produce naphthalene sulfonates.Naphthalene sulfonates are used in various formulations as concrete additives, gypsumboard additives, dye intermediates, tanning agents, and polymeric dispersants. Naphthalene isused to produce carbamate insecticides such as carbaryl, which is a wide-spectrum, generalpurposeinsecticide.

• Verwenden

  Naphthalene occurs naturally in fossil fuels such as coal and petroleum. It is commonly produced from the distillation and fractionation of coal tar. Naphthalene is used as an intermediate in the production of phthalate plasticizers, other plastics and resins, and other products such as dyes, wood preservatives, explosives, lubricants, pharmaceuticals, deodorizers, and insect repellants. Moth balls and other moth repellants, and some solid block deodorizers used for toilets and diaper pails, are made of crystalline naphthalene (ATSDR, 2005).

• Vorbereitung Methode

  Naphthalene is produced from coal tar or petroleum. It is made from petroleum by dealkylationof methylnaphthalenes in the presence of hydrogen at high temperature and pressure.Petroleum was a major source of naphthalene until the 1980s, but now most naphthaleneis produced from coal tar. The pyrolysis of bituminous coal produces coke and coke ovengases. Naphthalene is condensed by cooling the coke gas and then separated from the gas.

• Definition

  naphthalene: A white volatilesolid, C₁₀H₈; r.d. 1.025;m.p. 80.55°C; b.p. 218°C. Naphthaleneis an aromatic hydrocarbon withan odour of mothballs and is obtainedfrom crude oil. It is a raw materialfor making certain syntheticresins.

• Definition

  ChEBI: An aromatic hydrocarbon comprising two fused benzene rings. It occurs in the essential oils of numerous plant species e.g. magnolia.

• Synthesis Reference(s)

  Journal of the American Chemical Society, 96, p. 3686, 1974 DOI: 10.1021/ja00818a072
  The Journal of Organic Chemistry, 54, p. 4474, 1989 DOI: 10.1021/jo00279a046
  Tetrahedron Letters, 27, p. 5541, 1986 DOI: 10.1016/S0040-4039(00)85262-4

• Allgemeine Beschreibung

  Heterogeneous ozonolysis of naphthalene adsorbed on XAD-4 resin has been studied using annular denuder technique.

• Air & Water Reaktionen

  Highly flammable. Insoluble in water.

• Reaktivität anzeigen

  Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as Naphthalene, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction. Naphthalene, camphor, glycerol, or turpentine will react violently with chromic anhydride [Haz. Chem. Data 1967. p 68]. Friedel-Crafts acylation of Naphthalene using benzoyl chloride, catalyzed by AlCl3, must be conducted above the melting point of the mixture, or the reaction may be violent [Clar, E. et al., Tetrahedron, 1974, 30, 3296].

• Hazard

  Toxic by inhalation. Upper respiratory tract irritant, cataracts and hemolytic anemia. Possible carcinogen.

• Health Hazard

  Inhalation of naphthalene vapor may causeirritation of the eyes, skin, and respiratorytract, and injury to the cornea. Other symptoms are headache, nausea, confusion, andexcitability. The routes of exposure of thiscompound into the body are inhalation, ingestion, and absorption through the skin; andthe organs that may be affected are the eyes,liver, kidney, blood, skin, and central nervoussystem.
  The most severe toxic effects from naphthalene, however, may come from oral intakeof large doses of this compound. In animals, as well as in humans, ingestion of largeamounts may cause acute hemolytic anemiaand hemoglobinuria attributed to its metabolites, 1- and 2-naphthol and naphthoquinones.Infants are more sensitive than adults becauseof their lower capacity for methemoglobinreduction. Other symptoms from ingestion ofnaphthalene are gastrointestinal pain and kidney damage. The LD50 values reported inthe literature show variation among differentspecies. In mice, an oral LD50 value may beon the order of 600 mg/kg. Symptoms of respiratory depression and ataxia were noted.
  Chronic exposure to naphthalene vapormay affect the eyes, causing opacities of thelens and optical neuritis. The acute effectsfrom inhalation of its vapors at high concentrations are nausea and vomiting.
  Inhalation studies have shown positivetumorigenic response in mice. Studies conducted under National Toxicology Program(NTP) show clear evidence of carcinogenicityin rats resulting from inhalation of naphthalene vapors (NTP 2000). Increased incidencesof respiratory epithelial adenoma and olfactory epithelial neuroblastoma in the nose wereobserved in both the sexes of rats. On thebasis of these findings IARC has reevaluatednaphthalene and reclassified it under Group2B carcinogen, as possibly carcinogenic tohumans (IARC 2002)..

• Brandgefahr

  Flammable/combustible material. May be ignited by friction, heat, sparks or flames. Some may burn rapidly with flare burning effect. Powders, dusts, shavings, borings, turnings or cuttings may explode or burn with explosive violence. Substance may be transported in a molten form at a temperature that may be above its flash point. May re-ignite after fire is extinguished.

• Flammability and Explosibility

  Flammable

• Sicherheitsprofil

  Human poison by ingestion. Experimental poison by ingestion, intravenous, and intraperitoneal routes. Moderately toxic by subcutaneous route. An experimental teratogen. Experimental reproductive effects. An eye and skin irritant. Can cause nausea, headache, daphoresis, hematuria, fever, anemia, liver damage, vomiting, convulsions, and coma. Poisoning may occur by ingestion of large doses, inhalation, or skin absorption. Questionable carcinogen with experimental tumorigenic data. Flammable when exposed to heat or flame; reacts with oxidizing materials. Explosive reaction with dinitrogen pentaoxide. Reacts violently with CrOs, aluminum chloride + benzoyl chloride. Fires in the benzene scrubbers of coke oven gas plants have been attributed to oxidation of naphthalene. Explosive in the form of vapor or dust when exposed to heat or flame. To fight fire, use water, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

• mögliche Exposition

  Naphthalene is used as a chemical intermediate or feedstock for synthesis of phthalic, anthranilic, hydroxyl (naphthols), amino (naphthylamines), and sulfonic compounds; which are used in the manufacture of various dyes and in the preparation of phthalic anhydride, 1-naphthyl-N-methyl carbonate; and β-naphthol. Naphthalene is also used in the manufacture of hydronaphthalenes, synthetic resins; lampblack, smokeless powder; and celluloid. Naphthalene has been used as a moth repellent.
  Approximately 100 million people worldwide have G6PD deficiency which would make them more susceptible to hemolytic anemia on exposure to naphthalene. At present, more than 80 variants of this enzyme deficiency have been identified. The incidence of this deficiency is 0.1% in American and European Caucasians, but can range as high as 20% in American blacks and greater than 50% in certain Jewish groups. Newborn infants have a similar sensitivity to the hemolytic effects of naphthalene, even without G6PD deficiency.

• Carcinogenicity

  Naphthalene is reasonably anticipated to be a human carcinogenbased on sufficient evidence from studies in experimental animals.

• Versand/Shipping

  UN1334 Naphthalene, crude or Naphthalene, refined, Hazard Class: 4.1; Labels: 4.1-Flammable solid. UN2304 (molten) Hazard Class: 4.1; Labels: 4.1-Flammable solid.

• läuterung methode

  Crystallise naphthalene once or more times from the following solvents: EtOH, MeOH, CCl4, *C6H6, glacial acetic acid, acetone or diethyl ether, followed by drying at 60o in an Abderhalden drying apparatus. It has also been purified by vacuum sublimation and by fractional crystallisation from its melt. Other purification procedures include refluxing in EtOH over Raney Ni and chromatography of a CCl4 solution on alumina with *benzene as eluting solvent. Baly and Tuck [J Chem Soc 1902 1908] purified naphthalene for spectroscopy by heating with conc H2SO4 and MnO2, followed by steam distillation (repeating the process), and formation of the picrate which, after recrystallisation (m 150o) is decomposed with base and the naphthalene is steam distilled. It is then crystallised from dilute EtOH. It can be dried over P2O5 under vacuum (take care not to make it sublime). Also purify it by sublimation and subsequent crystallisation from cyclohexane. Alternatively, it has been washed at 85o with 10% NaOH to remove phenols, with 50% NaOH to remove nitriles, with 10% H2SO4 to remove organic bases, and with 0.8g AlCl3 to remove thianaphthalenes and various alkyl derivatives. Then it is treated with 20% H2SO4, 15% Na2CO3 and finally distilled. [Gorman et al. J Am Chem Soc 107 4404 1985.] Zone refining purified naphthalene from anthracene, 2,4-dinitrophenylhydrazine, methyl violet, benzoic acid, methyl red, chrysene, pentacene and indoline. [Beilstein 5 IV 1640.]

• Toxicity evaluation

  Systemic absorption of naphthalene vapor may result in cataracts. The biochemical basis for naphthalene cataract has been investigated. Naphthalene is metabolized in the liver to 1,2-dihydro-1,2-dihydroxynaphthalene. Lenticular catechol reductase biotransforms 1,2-dihydro-1,2-dihydroxynaphthalene to 1,2-dihydroxynaphthalene, which, in turn, is auto-oxidized in air at neutral pH to 1,2-naphthoquinone and hydrogen peroxide. Ascorbic acid reverses the latter reaction and forms dehydroascorbic acid, which diffuses out of the lens very slowly. Dehydroascorbic acid has been shown to accumulate in the lens of rabbits that were fed naphthalene and lens incubated in vitro with 1,2-dihydro- 1,2-dihydroxynaphthalene. The sequence of reactions involves the reduction of ascorbic acid by 1,2-naphthoquinone in the aqueous humor to dehydroascorbic acid, which rapidly penetrates the lens and is reduced by glutathione. Oxidized glutathione and 1,2-naphthoquinone may compete for enzyme glutathione reductase, which normally maintains high reticular levels of reduced glutathione. A reduction in the concentration of these coupled with the removal of oxygen from the aqueous humor due to the autooxidation of 1,2-dihydroxynaphthalene may make the lens sensitive to naphthalene toxicity.

• Inkompatibilitäten

  Dust may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Violent reactions with chromium(III) oxide, dinitrogen pentoxide; chromic anhydride.

• Waste disposal

  Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

• Einzelnachweise

  Formation Mechanisms of Naphthalene and Indene: From the Interstellar Medium to Combustion Flames. DOI:10.1021/acs.jpca.6b09735
  Functional Naphthalene Diimides: Synthesis, Properties, and Applications. DOI:10.1021/ACS.CHEMREV.6B00160
  The 100 Most Important Chemical Compounds: A Reference Guide DOI:10.5860/choice.45-3798
  A comprehensive guide to the hazardous properties of chemical substances DOI:10.1002/9780470134955
  A Dictionary of Chemistry (6th edition) DOI:10.1108/09504120910935291
  TOXICOLOGICAL REVIEW of NAPHTHALENE
  Naphthalene - Environmental Protection Agency

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