ChemicalBook > Product Catalog > Organic Chemistry > Hydrocarbons and derivatives > Aromatic hydrocarbons > Naphthalene
Basic information description Uses Health Hazard Toxicity Description Chemical Properties Definition Uses Air & Water Reactions Reactivity Profile Hazard Health Hazard Fire Hazard Purification Methods Safety Related Supplier
- Product Name:Naphthalene
- Synonyms: 'LGC' (2402) 'LGC' (2603) 1-NAPHTHALENE TAR CAMPHOR NAPTHALENE NAPTHALIN NAPHTHENE NAPHTHALENE
- Product Categories: Intermediates of Dyes and Pigments Naphthalene Organoborons Highly Purified Reagents Other Categories Zone Refined Products Analytical Chemistry Standard Solution of Volatile Organic Compounds for Water & Soil Analysis Standard Solutions (VOC) Chemistry Naphthalenes Analytical Standards AromaticsVolatiles/ Semivolatiles Volatiles/ Semivolatiles Arenes Building Blocks Organic Building Blocks Alpha Sort Chemical Class FumigantsVolatiles/ Semivolatiles Hydrocarbons Insecticides N NA - NIAnalytical Standards NaphthalenesChemical Class Neats N-OAlphabetic Pesticides PAH
- Mol File:91-20-3.mol
Naphthalene Chemical Properties
- Melting point:80-82 °C(lit.)
- Boiling point:218 °C(lit.)
- Density 0.99
- vapor density 4.4 (vs air)
- vapor pressure 0.03 mm Hg ( 25 °C)
- refractive index 1.5821
- Flash point: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
- explosive limit0.9-5.9%(V)
- Water Solubility 30 mg/L (25 ºC)
- Merck 14,6370
- BRN 1421310
- CAS DataBase Reference91-20-3(CAS DataBase Reference)
- NIST Chemistry ReferenceNaphthalene(91-20-3)
- EPA Substance Registry SystemNaphthalene(91-20-3)
- Hazard Codes Xn,N,F,T
- Risk Statements 22-40-50/53-67-65-38-11-39/23/24/25-23/24/25-52/53-20
- Safety Statements 36/37-46-60-61-62-45-16-7-33-25-9
- RIDADR UN 1334 4.1/PG 3
- WGK Germany 3
- RTECS QJ0525000
- TSCA Yes
- HazardClass 4.1
- PackingGroup III
- HS Code 29029010
- Hazardous Substances Data91-20-3(Hazardous Substances Data)
Naphthalene Usage And Synthesis
- descriptionNaphthalene 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 HazardMost 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.
- ToxicityNaphthalene 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.
- DescriptionNaphthalene 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 Propertieswhite to almost white crystals, crystalline flakes
- DefinitionChEBI: An aromatic hydrocarbon comprising two fused benzene rings. It occurs in the essential oils of numerous plant species e.g. magnolia.
- Usesmanufacture 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.
- Air & Water ReactionsHighly flammable. Insoluble in water.
- Reactivity ProfileVigorous 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 HazardFire 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 HazardFlammable/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.
- Purification MethodsCrystallise 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.]
Naphthalene Preparation Products And Raw materials
- Raw materialsPETROLEUM ETHERBiphenylKAOLINCOAL TARCOAL TARIndeneETHYLENE1,2,3,4-TetrahydronaphthaleneDODECYLBENZENETechnical naphthalenePhenol oil
- Preparation ProductsPhthalic anhydride1-Naphthol2-NaphtholBenzoic acid1-AminonaphthaleneGlyceriteLinolenic acid2-Amino-4,8-naphthalenedisulfonic acidDIBENZANTHRONENAPHTHENIC ACIDPeri acid1-Naphthalene acetic acid1'-Acetonaphthone1-Aminonaphthalene-6-sulfonic acid5-Amino-1-naphthalenesulfonic acidVat Yellow 21,4,5,8-Naphthalenetetracarboxylic acid2-Methylbutane1-IodonaphthaleneBUTYLNAPHTHALENESULFONIC ACID SODIUM SALT1,5-Naphthalenedisulfonic acidVat Yellow 4Vat Brown 5Slushing agent,high efficiencySEC-BUTYLAMINEBARIUM DINONYLNAPHTHALENESULFONATESlushing agent1,5-Dihydroxy naphthalenesynthetic fiber oil QDC-201disodium methylenebisnaphthalenesulphonate1-NitronaphthaleneSodium poly[(naphthaleneformaldehyde)sulfonate]2,6-DIMETHYLNAPHTHALENEDispersing agent DNdispersing agent CNF1-Naphthol-5-sulfonic acid
- Anthracene Phenanthrene 9,10-DIAMINOPHENANTHRENE PHENANTHRENE-9-CARBOXALDEHYDE 9-CHLOROANTHRACENE 9-Bromophenanthrene 9-AMINOPHENANTHRENE RARECHEM AL BD 0654 9-ACETYLPHENANTHRENE 3,6-DIMETHYLPHENANTHRENE 9,10-Dibromoanthracene 9-Bromoanthracene 9-Anthrracenecarbonitrile 2-ACETYLPHENANTHRENE 9-CYANOPHENANTHRENE 2-METHYLPHENANTHRENE ANTHRACENE-D10 Nabumetone
- Company Name:Shanghai Macklin Biochemical Co.,Ltd. Gold
- Products Intro:Product Name:Naphthalene solution
Purity:Standard for GC,>=99.5%(GC) Package:2ml
- Company Name:Hangzhou QiFei Chemical Co., Ltd. Gold
- Tel:0571-28950939 18058801870
- Products Intro:CAS:91-20-3
- Company Name:J & K SCIENTIFIC LTD.
- Tel:400-666-7788 +86-10-82848833
- Products Intro:Product Name:Naphthalene, 99%
- Company Name:Meryer (Shanghai) Chemical Technology Co., Ltd.
- Tel:+86-(0)21-61259100(Shanghai) +86-(0)755-86170099(ShenZhen) +86-(0)10-62670440(Beijing)
- Products Intro:Product Name:Naphthalene
Purity:99% Package:250g;1kg Remarks:AAA125343
- Company Name:3B Pharmachem (Wuhan) International Co.,Ltd.
- Tel:86-21-50328103 * 801、802、803、804 Mobile:18930552037
- Products Intro:Product Name:Naphthalene
Purity:99% HPLC Package:1Mg ; 5Mg;10Mg ;100Mg;250Mg ;500Mg ;1g;2.5g ;5g ;10g