Lastest Price from Naphthalene manufacturers
- US $1.00 / kg
- Min. Order: 1kg
- Purity: 99%
- Supply Ability: 1000kg
- US $10.00 / KG
- Min. Order: 1KG
- Purity: 99%
- Supply Ability: 500tons/month
|Naphthalene Chemical Properties|
|Melting point ||80-82 °C(lit.)|
|Boiling point ||218 °C(lit.)|
|vapor density ||4.4 (vs air)|
|vapor pressure ||0.03 mm Hg ( 25 °C)|
|refractive index ||1.5821|
|Fp ||174 °F|
|storage temp. ||APPROX 4°C
|solubility ||methanol: soluble50mg/mL, clear, colorless|
|form ||Faint beige to brown to salmon red powder|
|color ||White to almost white|
|Water Solubility ||30 mg/L (25 ºC)|
|Henry's Law Constant||5.64 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999)|
|Exposure limits||TLV-TWA 10 ppm （～50 mg/m3) (ACGIH,
MSHA, and OSHA); STEL 15 ppm
(～75 mg/m3) (ACGIH); IDLH 500 ppm.|
|CAS DataBase Reference||91-20-3(CAS DataBase Reference)|
|NIST Chemistry Reference||Naphthalene(91-20-3)|
|EPA Substance Registry System||Naphthalene(91-20-3)|
|Naphthalene Usage And Synthesis|
|description||Naphthalene is a white solid chemical that vaporizes easily. It has a strong smell. You can sometimes smell naphthalene in the air or in water. Called white tar and tar camphor, naphthalene is used in mothballs and moth flakes. Petroleum and coal contain naphthalene.|
Naphthalene, the simplest of the fused or condensed ring hydrocarbon compounds composed of two benzene rings sharing two adjacent carbon atoms. Naphthalene is the most abundant single constituent of coal tar, a volatile product from the destructive distillation of coal, and is also formed in modern processes for the high-temperature cracking (breaking up of large molecules) of petroleum.
1-Methylnaphthalene and 2-methylnaphthalene are naphthalene-related compounds. 1-Methylnaphthalene is a clear liquid and 2-methylnaphthalene is a solid; both can be smelled in air and in water at very low concentrations. 1-Methylnaphthalene and 2-methylnaphthalene are used to make other chemicals such as dyes and resins. 2-Methylnaphthalene is also used to make vitamin K.
- In industry, naphthalene is used to manufacture a plastic called polyvinyl chloride (PVC). In public restrooms, naphthalene can be found in toilet deodorant blocks. At home, naphthalene can be found in moth repellents.
- Naphthalene balls are extensively used as household preservative of woolen clothes and as a deodorant tablet for the toilets, urinals, bathrooms etc. These are manufactured from naphthalene flakes by a tabletmaking machine having its ball shape die.
- Naphthalene is an important hydrocarbon raw material and is primarily used to manufacture phthalic anhydride and polyvinyl chloride (PVC) plastics, but is also used in moth repellents and toilet deodorant blocks.
- Naphthalene was used in liquid-phase exfoliation of graphite in organic solvents for the production of graphene sheets. It was used in preparation of carbon-coated Si 70 Sn 30 nanoparticles.
- It was used as fluorescent probe to study the aggregation behavior of sodium cholate.
- It was used to investigate influence of added short chain linear and branched alcohols on the binding of 1:1 complex of naphthalene and β-cyclodextrin.
|Health Hazard||Most of the data available on the toxic effects of naphthalene have been derived from animal studies conducted either in vivo or with in vitro preparations.|
Rats and mice breathing naphthalene vapors daily for a lifetime had irritated noses and nose tumors and irritated lungs. Some female mice had lung tumors. Some animals got cloudy eyes after ingesting it.
It is not clear if naphthalene causes reproductive problems in animals. Although there is no direct data showing that naphthalene can cause cancer in people, naphthalene exposure can lead to cancer in animals.
Exposure to large amounts of naphthalene may damage or destroy red blood cells, a condition called hemolytic anemia. Symptoms of hemolytic anemia are feeling very tired or restless, lack of appetite, and pale skin. Exposure to large amounts of naphthalene may also cause upset stomach, diarrhea, blood in the urine,and yellow-colored skin. Very young children and unborn children are at higher risk if they are exposed to naphthalene, especially if they ingest the chemical. Some infants have become ill when they were close to clothing or blankets stored in naphthalene mothballs.
|Toxicity||Naphthalene is a white solid substance with a strong smell. Poisoning from naphthalene destroys or changes red blood cells so they cannot carry oxygen. This can cause organ damage.|
In humans, naphthalene is broken down to alpha-naphthol, which is linked to the development of hemolytic anemia. Kidney and liver damage may also occur. Alpha-naphthol and other metabolites are excreted in urine.
In animals, naphthalene breaks down into other compounds including alpha-naphthol, which may affect the lungs and eyes. Naphthalene was found in the milk of exposed cows, but the residues disappeared quickly after the cows were no longer exposed. Nearly all the naphthalene was broken down into other compounds and excreted in their urine.
|Description||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.|
|Chemical Properties||Naphthalene is a colorless to brown crystalline
solid with a characteristic “moth ball” odor. Shipped
as a molten solid.|
|Chemical Properties||white to almost white crystals, crystalline flakes|
|Physical properties||Naphthalene is a crystalline, white, flammable, polycyclic aromatic hydrocarbon consisting of two fused benzene rings. It has a pungent odor and sublimes readily above its melting point; it has been traditionally used in moth balls and is responsible for the moth balls characteristic odor. Naphthalene is a natural component of fossil fuels and is the single most abundant component of coal tar, accounting for approximately 11% of dry coal tar.|
|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.|
|Uses||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.
|Uses||Naphthalene is used as a moth repellent; inscintillation counters; and as a raw materialin the manufacture of naphthol, phthalic anhy-dride, and halogenated naphthalenes. It is alsoused in dyes, explosives and lubricants, andin breaking emulsion.|
|Uses||manufacture of phthalic and anthranilic acids which are used in making indigo, indanthrene, and triphenylmethane dyes. manufacture of hydroxyl (naphthols), amino (naphthylamines), sulfonic acid and similar Compounds used in the dye industries. manufacture of synthetic resins, celluloid, lampblack, smokeless powder. manufacture of hydronaphthalenes (Tetralin, Decalin) which are used as solvents, in lubricants, and in motor fuels. Moth repellent and insecticide.|
|Definition||ChEBI: An aromatic hydrocarbon comprising two fused benzene rings. It occurs in the essential oils of numerous plant species e.g. magnolia.|
|Definition||A white crystalline solid with a
distinctive smell of mothballs. Naphthalene
is found in both the middle- and
heavy-oil fractions of crude oil and is obtained
by fractional crystallization. It is
used in the manufacture of benzene-1,2-dicarboxylic
anhydride (phthalic anhydride and thence in the production of plastics
The structure of naphthalene is ‘benzene-
like’, having two six-membered rings
fused together. The reactions are characteristic
of AROMATIC COMPOUNDS.
|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.|
|Production Methods||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.|
|Air & Water Reactions||Highly flammable. Insoluble in water.|
|Reactivity Profile||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
|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)..
|Health Hazard||Fire may produce irritating and/or toxic gases. Contact may cause burns to skin and eyes. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution.|
|Fire Hazard||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.|
|Safety Profile||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.|
|Potential Exposure||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
|Carcinogenicity||Naphthalene is reasonably anticipated to be a human carcinogenbased on sufficient evidence from studies in experimental animals.|
|Source||Schauer et al. (1999) reported naphthalene in diesel fuel at a concentration of 600 μg/g
and in a diesel-powered medium-duty truck exhaust at an emission rate of 617 μg/km. Detected in
distilled water-soluble fractions of 87 octane gasoline (0.24 mg/L), 94 octane gasoline (0.21
mg/L), Gasohol (0.29 mg/L), No. 2 fuel oil (0.60 mg/L), jet fuel A (0.34 mg/L), diesel fuel (0.25
mg/L), military jet fuel JP-4 (0.18 mg/L) (Potter, 1996), and used motor oil (116 to 117 μg/L)
(Chen et al., 1994). Lee et al. (1992) investigated the partitioning of aromatic hydrocarbons into
water. They reported concentration ranges from 350 to 1,500 mg/L and 80 to 300 μg/L in diesel
fuel and the corresponding aqueous phase (distilled water), respectively. Diesel fuel obtained from
a service station in Schlieren, Switzerland contained 708 mg/L naphthalene (Schluep et al., 2001).
California Phase II reformulated gasoline contained naphthalene at a concentration of 1.04 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).|
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 naphthalene concentrations reported in water-soluble fractions unleaded gasoline,
kerosene, and diesel fuel were 989, 644, and 167 ug/L.
Based on laboratory analysis of 7 coal tar samples, naphthalene concentrations ranged from 940
to 71,000 ppm (EPRI, 1990). Detected in 1-yr aged coal tar film and bulk coal tar at concentraions
of 26,000 and 29,000 mg/kg, respectively (Nelson et al., 1996). A high-temperature coal tar
contained naphthalene at an average concentration of 8.80 wt % (McNeil, 1983). Nine
commercially available creosote samples contained naphhalene at concentrations ranging from
3,800 to 52,000 mg/kg (Kohler et al., 2000). Lee et al. (1992a) equilibrated eight coal tars with
distilled water at 25 °C. The maximum concentration of naphthalene observed in the aqueous
phase was 14 mg/L.
Naphthalene was detected in soot generated from underventilated combustion of natural gas
doped with toluene (3 mole %) (Tolocka and Miller, 1995).
Typical concentration in a heavy pyrolysis oil is 17.8 wt % (Chevron Phillips, May 2003).
Detected in asphalt fumes at an average concentration of 1.15 ng/m3 (Wang et al., 2001).
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 rate of
naphthalene was 227 mg/kg of pine burned. Emission rates of naphthalene were not measured
during the combustion of oak and eucalyptus.
|Environmental fate||Biological. In activated sludge, 9.0% of the applied amount mineralized to carbon dioxide after
5 d (Freitag et al., 1985). Under certain conditions, Pseudomonas sp. oxidized naphthalene to cis-
1,2-dihydro-1,2-dihydroxynaphthalene (Dagley, 1972). This metabolite may be oxidized by
Pseudomonas putida to carbon dioxide and water (Jerina et al., 1971). Under aerobic conditions,
Cunninghamella elegans degraded naphthalene to 1-naphthol, 2-naphthol, trans-1,2-dihydroxy 1,2-dihydronaphthalene, 4-hydroxy-1-tetralone, and 1,4-naphthoquinone. Under aerobic conditions,
Agnenellum, Oscillatoria, and Anabaena degraded naphthalene to 1-naphthol, cis-1,2-
dihydroxy-1,2-dihydronaphthalene, and 4-hydroxy-1-tetralone (Kobayashi and Rittman, 1982;
Riser-Roberts, 1992). Candida lipolytica, Candida elegans, and species of Cunninghamella,
Syncephalastrum and Mucor oxidized naphthalene to 1-naphthol, 2-naphthol, trans-1,2-
dihydroxy-1,2-dihydronaphthalene, 4-hydroxy-1-tetralone, 1,2-naphthoquinone, and 1,4-naphthouinone
(Cerniglia et al., 1978, 1980; Dodge and Gibson, 1980).|
Soil. The half-lives of naphthalene in pristine and oil-contaminated sediments are >88 d and 4.9
h, respectively (Herbes and Schwall, 1978). Reported half-lives for naphthalene in a Kidman
sandy loam and McLaurin sandy loam are 2.1 and 2.2 d, respectively (Park et al., 1990).
Surface Water. The volatilization half-life of naphthalene from surface water (1 m deep, water
velocity 0.5 m/sec, wind velocity 22.5 m/sec) using experimentally determined Henry’s law
constants is estimated to be 16 h (Southworth, 1979). The reported half-lives of naphthalene in an
oil-contaminated estuarine stream, clean estuarine stream, coastal waters, and in the Gulf stream
are 7, 24, 63, and 1,700 d, respectively (Lee, 1977). Mackay and Wolkoff (1973) estimated an
evaporation half-life of 2.9 h from a surface water body that is 25 °C and 1 m deep. In a laboratory
experiment, the average volatilization half-life of naphthalene in a stirred water vessel (outer
dimensions 22 x 10 x 21 cm) at 23 °C and an air flow rate of 0.20 m/sec is 380 min. The half-life
was independent of wind velocity or humidity but very dependent upon temperature (Kl?pffer et
Groundwater. The estimated half-life of naphthalene in groundwater in the Netherlands was 6
months (Zoeteman et al., 1981). Nielsen et al. (1996) studied the degradation of naphthalene in a
shallow, glaciofluvial, unconfined sandy aquifer in Jutland, Denmark. As part of the in situ
microcosm study, a cylinder that was open at the bottom and screened at the top was installed
through a cased borehole approximately 5 m below grade. Five liters of water was aerated with
atmospheric air to ensure aerobic conditions were maintained. Groundwater was analyzed weekly
for approximately 3 months to determine naphthalene concentrations with time. The experimentally
determined first-order biodegradation rate constant and corresponding half-life following a 6-d lag phase were 0.8/d and 20.8 h, respectively.
Photolytic. Irradiation of naphthalene and nitrogen dioxide using a high pressure mercury lamp
(λ >290 nm) yielded the following principal products: 1- and 2-hydroxynaphthalene, 1-hydroxy-2-
nitronaphthalene, 1-nitronaphthalene, 2,3-dinitronaphthalene, phthalic anhydride, 1,3-, 1,5- and
1,8-dinitronaphthalene (Barlas and Parlar, 1987). In a similar experiment, naphthalene crystals
was heated to 50 °C and exposed to pure air containing NO and OH radicals. Photodecomposition
followed first-order kinetics indicating the concentration of OH radicals remained constant
throughout the reaction. Degradation products identified by GC/MS were 1-naphthol, 2-naphthol,
1-nitronaphthalene, 2-nitronaphthalene, 1,4-naphthoquinone, 1,4-naphthoquinone-2,3-epoxide, 3-
nitrophthalic anhydride, phthalic anhydride, 4-methyl-2H-1-benzopyran-2-one, 1(3H)-isobenzofuranone,
1,2-benzenecarboxaldehyde, cis-2-formyl-cinnamaldehyde, trans-2-formylcinnamaldehyde,
and phthalide. The following compounds were tentatively identified: 2,7-naphthalenediol,
2-nitro-1-naphthol, 4-nitro-1-naphthol, and 2,4-dinitro-1-naphthol. Photoproducts identified
by HPLC included: benzoic acid, cinnamic acid, 2,4-dinitro-1-naphthol, 2-formylcinnamic acid,
cis-2-formylcinnamaldehyde, trans-2-formylcinnamaldehyde, 1-nitronaphthalene, 2-nitronaphthalene,
1-naphthol, 2-naphthol, 1,4-naphthoquinone, 1,4-naphthoquinone-2,3-epoxide, 3-nitrophthalic
anhydride, oxalic acid, phthalic acid, phthalaldehyde, and phthalide (Lane et al., 1997).
Chemical/Physical. An aqueous solution containing chlorine dioxide in the dark for 3.5 d
oxidized naphthalene to chloronaphthalene, 1,4-dichloronaphthalene, and methyl esters of phthalic
acid (Taymaz et al., 1979). In the presence of bromide ions and a chlorinating agent (sodium
hypochlorite), major products identified at various reaction times and pHs include 1-
bromonaphthalene, dibromonaphthalene, and 2-bromo-1,4-naphthoquinone. Minor products
identified include chloronaphthalene, dibromonaphthalene, bromochloronaphthalene, bromonaphthol,
dibromonaphthol, 2-bromonaphthoquinone, dichloronaphthalene, and chlorodibromonaphthalene
(Lin et al., 1984).
|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
|Purification Methods||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.]|
|Incompatibilities||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.|
|Regulations||Department of Transportation (DOT)|
Naphthalene is considered a hazardous material, and special requirements have been set for marking, labeling, and transporting this material.
Environmental Protection Agency (EPA)
Clean Air Act
Mobile Source Air Toxics: Listed as a substance for which regulations are to be developed. National Emissions Standards for Hazardous Air Pollutants: Listed as a hazardous air pollutant.
Clean Water Act
Effluent Guidelines: Listed as a toxic pollutant. Designated a hazardous substance.
Comprehensive Environmental Response, Compensation, and Liability Act
Reportable quantity (RQ) = 100 lb.
Emergency Planning and Community Right-To-Know Act
Toxics Release Inventory: Listed substance subject to reporting requirements.
Resource Conservation and Recovery Act
Listed Hazardous Waste: Waste codes for which the listing is based wholly or partly on the presence of naphthalene = U165, F024, F025, F034, K001, K035, K087, K145. Listed as a hazardous constituent of waste.
Occupational Safety and Health Administration (OSHA)
While this section accurately identifies OSHA’s legally enforceable PELs for this substance in 2010, specific PELs may not reflect the more current studies and may not adequately protect workers. Permissible exposure limit (PEL) = 10 ppm (50 mg/m3).
|Naphthalene Preparation Products And Raw materials|
|Raw materials||PETROLEUM ETHER-->Biphenyl-->KAOLIN-->COAL TAR-->COAL TAR-->Indene-->ETHYLENE-->1,2,3,4-Tetrahydronaphthalene-->DODECYLBENZENE-->Technical naphthalene-->Phenol oil|
|Preparation Products||Phthalic anhydride-->1-Naphthol-->2-Naphthol-->Benzoic acid-->1-Aminonaphthalene-->Glycerite-->Linolenic acid-->2-Amino-4,8-naphthalenedisulfonic acid-->DIBENZANTHRONE-->NAPHTHENIC ACID-->Peri acid-->1-Naphthalene acetic acid-->1'-Acetonaphthone-->1-Aminonaphthalene-6-sulfonic acid-->5-Amino-1-naphthalenesulfonic acid-->Vat Yellow 2-->1,4,5,8-Naphthalenetetracarboxylic acid-->2-Methylbutane-->1-Iodonaphthalene-->BUTYLNAPHTHALENESULFONIC ACID SODIUM SALT-->1,5-Naphthalenedisulfonic acid-->Vat Yellow 4-->Vat Brown 5-->Slushing agent,high efficiency-->SEC-BUTYLAMINE-->BARIUM DINONYLNAPHTHALENESULFONATE-->Slushing agent-->1,5-Dihydroxy naphthalene-->synthetic fiber oil QDC-201-->disodium methylenebisnaphthalenesulphonate-->1-Nitronaphthalene-->Sodium poly[(naphthaleneformaldehyde)sulfonate]-->2,6-DIMETHYLNAPHTHALENE-->Dispersing agent DN-->dispersing agent CNF-->1-Naphthol-5-sulfonic acid|