Naphthalin 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 m?glich.
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 K?rper durch Inhalation, über die Haut und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20°C tritt langsam eine gesundheitssch?dliche Kontamination der Luft ein. (S. Anm.)
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: M?glich sind Auswirkungen auf das Blut mit nachfolgenden Blutzellsch?digungen (H?molyse) (s.Anm.). Die Auswirkungen treten u.U. verz?gert ein. Exposition durch Verschlucken kann zum Tod führen. ?rztliche Beobachtung notwendig.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
M?glich sind Auswirkungen auf das Blut mit nachfolgender chronischer h?molytischer An?mie (Blutarmut). M?glich sind Auswirkungen auf die Augen mit nachfolgender Linsentrübung. M?glicherweise krebserzeugend für den Menschen.
LECKAGE
Pers?nliche Schutzausrüstung: Atemschutzfilter für organische Gase und D?mpfe. NICHT in die Umwelt gelangen lassen. Verschüttetes Material in abgedeckten Beh?ltern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste sorgf?ltig sammeln. An sicheren Ort bringen.
R-S?tze Betriebsanweisung:
R22:Gesundheitssch?dlich beim Verschlucken.
R40:Verdacht auf krebserzeugende Wirkung.
R50/53:Sehr giftig für Wasserorganismen, kann in Gew?ssern l?ngerfristig sch?dliche Wirkungen haben.
R67:D?mpfe k?nnen Schl?frigkeit und Benommenheit verursachen.
R65:Gesundheitssch?dlich: kann beim Verschlucken Lungensch?den 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:Sch?dlich für Wasserorganismen, kann in Gew?ssern l?ngerfristig sch?dliche Wirkungen haben.
S-S?tze Betriebsanweisung:
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S46:Bei Verschlucken sofort ?rztlichen Rat einholen und Verpackung oder Etikett vorzeigen.
S60:Dieses Produkt und sein Beh?lter sind als gef?hrlicher Abfall zu entsorgen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S62:Bei Verschlucken kein Erbrechen herbeiführen. Sofort ?rztlichen Rat einholen und Verpackung oder dieses Etikett vorzeigen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).
S16:Von Zündquellen fernhalten - Nicht rauchen.
S7:Beh?lter 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).
Schutzma?nahmen 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.
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, C
10H
8; 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.
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.
Reaktivit?t 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.
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.
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.
m?gliche 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.
l?uterung 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.]
Inkompatibilit?ten
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.6b09735Functional Naphthalene Diimides: Synthesis, Properties, and Applications. DOI:
10.1021/ACS.CHEMREV.6B00160The 100 Most Important Chemical Compounds: A Reference Guide DOI:
10.5860/choice.45-3798A comprehensive guide to the hazardous properties of chemical substances DOI:
10.1002/9780470134955A Dictionary of Chemistry (6th edition) DOI:
10.1108/09504120910935291TOXICOLOGICAL REVIEW of NAPHTHALENE Naphthalene - Environmental Protection Agency
Naphthalin Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
Naphthalin-1,4,5,8-tetracarbonsure
1-Naphthol
8-Aminonaphthalin-1-sulfonsure
Dibenzo[b,def]chrysen-7,14-dion
Dinatriummethylenbisnaphthalinsulfonat
DIBENZANTHRONE
Linolensure
Natriumbutylnaphthalinsulfonat
1-Nitronaphthalin
Naphthalin-1,5-diol
2-(1-Oxonaphtho[2,1-b]thien-2(1H)-yliden)naphtho[2,1-b]thiophen-1(2H)-on
Tannine
Bariumbis(dinonylnaphthalinsulfonat)
2,8-Diphenylanthra[2,1-d:6,5-d']bisthiazol-6,12-dion
SEC-BUTYLAMINE
1-Naphthylessigsure
3-Aminonaphthalin-1,5-disulfonsure
2,6-DIMETHYLNAPHTHALENE
2-Methylbutan
dispersing agent CNF
5-Aminonaphthalin-2-sulfonsure
Naphthensuren
Dispersing agent DN
Phthalsureanhydrid
5-Aminonaphthalin-1-sulfonsure
Slushing agent,high efficiency
Sodium poly[(naphthaleneformaldehyde)sulfonate]
1-Iodnaphthalin
Naphthalin-1,5-disulfonsure
Benzoesure
1-Naphthylamin
Slushing agent
synthetic fiber oil QDC-201
2-Naphthol
1-Naphthol-5-sulfonic acid
Methyl-1-naphthylketon
