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NAPHTHALENE


CAS NO:91-20-3
EC NO:214-552-7

Naphthalene is an organic compound with formula C10H8. 
Naphthalene is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass.As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. 
Naphthalene is best known as the main ingredient of traditional mothballs.

Physical properties:
Naphthalene molecule can be viewed as the fusion of a pair of benzene rings. (In organic chemistry, rings are fused if they share two or more atoms.) As such, naphthalene is classified as a benzenoid polycyclic aromatic hydrocarbon (PAH).

The eight carbon atoms that are not shared by the two rings carry one hydrogen atom each. For purpose of the standard IUPAC nomenclature of derived compounds, those eight atoms are numbered 1 through 8 in sequence around the perimeter of the molecule, starting with a carbon atom adjacent to a shared one. The shared carbon atoms are labeled 4a (between 4 and 5) and 8a (between 8 and 1).

Production:
Most naphthalene is derived from coal tar. From the 1960s until the 1990s, significant amounts of naphthalene were also produced from heavy petroleum fractions during petroleum refining, but today petroleum-derived naphthalene represents only a minor component of naphthalene production.

Uses
Naphthalene is used mainly as a precursor to other chemicals. The single largest use of naphthalene is the industrial production of phthalic anhydride, although more phthalic anhydride is made from o-xylene. Many azo dyes are produced from naphthalene, and so is the insecticide 1-naphthyl-N-methylcarbamate (carbaryl). Other useful agrichemicals include naphthoxyacetic acids.


Nadoxolol is a beta blocker.
Hydrogenation of naphthalene gives tetralin, which is used as a hydrogen-donor solvent.

Alkylation of naphthalene with propylene gives a mixture of diisopropylnaphthalenes, which are useful as nonvolatile liquids used in inks.

Naphthalenesulfonic acids and sulfonates:
Many naphthalenesulfonic acids and sulfonates are useful. Alkyl naphthalene sulfonate are surfactants, The aminonaphthalenesulfonic acids, naphthalenes substituted with ethers and sulfonic acids, are intermediates in the preparation of many synthetic dyes. The hydrogenated naphthalenes tetrahydronaphthalene (tetralin) and decahydronaphthalene (decalin) are used as low-volatility solvents. Naphthalene sulfonic acids are also used in the synthesis of 1-naphthol and 2-naphthol, precursors for various dyestuffs, pigments, rubber processing chemicals and other chemicals and pharmaceuticals.

Naphthalene sulfonic acids are used in the manufacture of naphthalene sulfonate polymer plasticizers (dispersants), which are used to produce concrete and plasterboard (wallboard or drywall). They are also used as dispersants in synthetic and natural rubbers, and as tanning agents (syntans) in leather industries, agricultural formulations (dispersants for pesticides), dyes and as a dispersant in lead–acid battery plates.

Naphthalene sulfonate polymers are produced by treating naphthalenesulfonic acid with formaldehyde, followed by neutralization with sodium hydroxide or calcium hydroxide. These products are commercially sold as superplasticizers for the production of high strength concrete.

Laboratory uses:
Molten naphthalene provides an excellent solubilizing medium for poorly soluble aromatic compounds. In many cases it is more efficient than other high-boiling solvents, such as dichlorobenzene, benzonitrile, nitrobenzene and durene. The reaction of C60 with anthracene is conveniently conducted in refluxing naphthalene to give the 1:1 Diels–Alder adduct.The aromatization of hydroporphyrins has been achieved using a solution of DDQ in naphthalene.

Wetting agent and surfactant:
Alkyl naphthalene sulfonates (ANS) are used in many industrial applications as nondetergent wetting agents that effectively disperse colloidal systems in aqueous media. The major commercial applications are in the agricultural chemical industry, which uses ANS for wettable powder and wettable granular (dry-flowable) formulations, and the textile and fabric industry, which utilizes the wetting and defoaming properties of ANS for bleaching and dyeing operations.

As a fumigant:
Naphthalene has been used as a household fumigant. 
Naphthalene was once the primary ingredient in mothballs, although its use has largely been replaced in favor of alternatives such as 1,4-dichlorobenzene. In a sealed container containing naphthalene pellets, naphthalene vapors build up to levels toxic to both the adult and larval forms of many moths that attack textiles. Other fumigant uses of naphthalene include use in soil as a fumigant pesticide, in attic spaces to repel animals and insects, and in museum storage-drawers and cupboards to protect the contents from attack by insect pests.

Naphthalene is a repellent to opossums.

Other uses:
Naphthalene is used in pyrotechnic special effects such as the generation of black smoke and simulated explosions.
Naphthalene is used to create artificial pores in the manufacture of high-porosity grinding wheels. In the past, naphthalene was administered orally to kill parasitic worms in livestock. 
Naphthalene and its alkyl homologs are the major constituents of creosote. 
Naphthalene is used in engineering to study heat transfer using mass sublimation.

Naphthalene has been proposed as an alternative propellant for cold gas satellite thrusters.

Properties:
Chemical formula:    C10H8
Molar mass:    128.174 g·mol−1
Appearance:    White solid crystals/ flakes
Odor:    Strong odor of coal tar

Naphthalene is a white, volatile, solid polycyclic hydrocarbon with a strong mothball odor.
Naphthalene is obtained from either coal tar or petroleum distillation and is primarily used to manufacture phthalic anhydride, but is also used in moth repellents. Exposure to naphthalene is associated with hemolytic anemia, damage to the liver and neurological system, cataracts and retinal hemorrhage. 
Naphthalene is reasonably anticipated to be a human carcinogen and may be associated with an increased risk of developing laryngeal and colorectal cancer. (NCI05)

Naphthalene appears as a white crystalline volatile solid with a strong coal-tar odor. The solid is denser than water and insoluble in water. Burns, but may be difficult to ignite. In the molten form it is very hot. Exposure to skin must be avoided. Also the vapors given off by the material may be toxic. Used as a moth repellent, fumigant, lubricants, and to make other chemicals, and for many other uses

Naphthalene is an aromatic hydrocarbon comprising two fused benzene rings. 
Naphthalene occurs in the essential oils of numerous plant species e.g. magnolia. 
Naphthalene has a role as a volatile oil component, a plant metabolite, an environmental contaminant, a carcinogenic agent and an apoptosis inhibitor. 
Naphthalene is an ortho-fused bicyclic arene and a member of naphthalenes.

The primary use for naphthalene is in the production of phthalic anhydride. However, o-xylene is replacing naphthalene as the preferred raw material for phthalic anhydride production.

Naphthalene is used indoors as a moth repellant, and placed in closed drawers, closets, and other storage areas. 
Naphthalene is also used in attics as a squirrel and bat repellant. Outdoors, it is used around garden and building peripheries to repel animals such as snakes and rabbits.

Industry Uses:    
-Abrasives
-Adhesives and sealant chemicals
-Agricultural chemicals (non-pesticidal)
-Feedstock processed on-site
-Fuels and fuel additives
-Intermediates
-Lubricants and lubricant additives
-Paint additives and coating additives not described by other categories
-Processing aids, not otherwise listed
-Solvents (which become part of product formulation or mixture)
-Surface active agents

Consumer Uses:
-Abrasives
-Adhesives and sealants
-Fuels and related products

Industry Processing Sectors:
-Agriculture, forestry, fishing and hunting
-All other basic organic chemical manufacturing
-All other chemical product and preparation manufacturing
-Asphalt paving, roofing, and coating materials manufacturing
-Construction
-Miscellaneous manufacturing
-Oil and gas drilling, extraction, and support activities
-Paint and coating manufacturing
-Petrochemical manufacturing
-Petroleum lubricating oil and grease manufacturing
-Petroleum refineries
-Soap, cleaning compound, and toilet preparation manufacturing
-Synthetic rubber manufacturing
-Textiles, apparel, and leather manufacturing
-Transportation equipment manufacturing
-Wholesale and retail trade

Naphthalene is made from crude oil or coal tar. 
Naphthalene is also produced when things burn, so naphthalene is found in cigarette smoke, car exhaust, and smoke from forest fires. 
Naphthalene is used as an insecticide and pest repellent. 
Naphthalene was first registered as a pesticide in the United States in 1948.

Naphthalene is used in the production of phthalic anhydride; it is also used in mothballs.

Naphthalene, the simplest of the fused or condensed ring hydrocarbon compounds composed of two benzene rings sharing two adjacent carbon atoms; chemical formula, C10H8. 
Naphthalene is an important hydrocarbon raw material that gives rise to a host of substitution products used in the manufacture of dyestuffs and synthetic resins. 
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. 
Naphthalene is commercially produced by crystallization from the intermediate fraction of condensed coal tar and from the heavier fraction of cracked petroleum. Naphthalene crystallizes in lustrous white plates, melting at 80.1° C (176.2° F) and boiling at 218° C (424° F). 
Naphthalene is almost insoluble in water. Naphthalene is highly volatile and has a characteristic odour; it has been used as moth repellent.

Naphthalene is derived from the Persian word, “neft,” which means flammable liquid. 
Naphthalene isomers are comprised of two fused benzene rings. 

About Naphthalene
Helpful information
Naphthalene is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 000 to < 1 000 000 tonnes per annum.

Naphthalene is used in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Consumer Uses
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which Naphthalene is most likely to be released to the environment.

Article service life
Release to the environment of Naphthalene can occur from industrial use: manufacturing of the substance, as an intermediate step in further manufacturing of another substance (use of intermediates) and in processing aids at industrial sites.
Other release to the environment of Naphthalene is likely to occur from: outdoor use in long-life materials with high release rate (e.g. tyres, treated wooden products, treated textile and fabric, brake pads in trucks or cars, sanding of buildings (bridges, facades) or vehicles (ships)).
Naphthalene can be found in products with material based on: leather (e.g. gloves, shoes, purses, furniture).

Widespread uses by professional workers
Naphthalene is used in the following products: explosives, pH regulators and water treatment products and laboratory chemicals.
Naphthalene is used in the following areas: health services and scientific research and development.
Other release to the environment of Naphthalene is likely to occur from: outdoor use in close systems with minimal release (e.g. hydraulic liquids in automotive suspension, lubricants in motor oil and break fluids) and indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).

Formulation or re-packing
Naphthalene is used in the following products: explosives, non-metal-surface treatment products and leather treatment products.
Naphthalene has an industrial use resulting in manufacture of another substance (use of intermediates).
Release to the environment of Naphthalene can occur from industrial use: formulation of mixtures.

Uses at industrial sites
Naphthalene is used in the following products: laboratory chemicals.
Naphthalene has an industrial use resulting in manufacture of another substance (use of intermediates).
Naphthalene is used for the manufacture of: chemicals and mineral products (e.g. plasters, cement).
Release to the environment of Naphthalene can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites and manufacturing of the substance.

Manufacture
Release to the environment of Naphthalene can occur from industrial use: manufacturing of the substance and as an intermediate step in further manufacturing of another substance (use of intermediates).

Naphthalene is the most abundant component of coal tar, which is the liquid byproduct of the distillation of coal into coke for use as a smokeless fuel.

The most common current use for naphthalene is as a raw material in the production of phthalic anhydride, which is often used in the production of dyes, plasticizers, insecticides and some pharmaceutical products.

In the past, naphthalene was used as a fumigant for repelling moths, for which it is popularly known as mothballs. Another classical use of naphthalene was as a fumigant for soil. Such uses are now discontinued.

Naphthalene is a white, crystalline solid that is flammable and smells strongly of mothballs.

Naphthalene is an aromatic hydrocarbon, found to be nonpolar in nature. 
Naphthalene is generally produced from petroleum or coal-tar. 
Naphthalene, an organic compound, is widely used as an intermediate in chemical and plastic industry. 
Naphthalenes other applications include, its role in the manufacturing of fungicides/insecticides and as a model compound for investigating the metabolism of polycyclic aromatic hydrocarbons (PAHs) by bacteria. 

Naphthalene is an organic compound with formula C ₁₀H ₈. 
Naphthalene is the simplest poly-cyclic aromatic hydrocarbon and appears as a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass.

Uses
Naphthalene is used in the production of phthalic anhydride; 
Naphthalene is also used in mothballs.
Other uses of naphthalene include 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.

Formula: C10H8
Molecular mass: 128.18
Boiling point: 218°C
Sublimes at room temperature
Melting point: 80°C
Density: 1.16 g/cm³
Solubility in water at 20°C: very poor
Vapour pressure, Pa at 25°C: 11
Relative vapour density (air = 1): 4.42
Flash point: 80°C c.c.
Auto-ignition temperature: 540°C
Explosive limits, vol% in air: 0.9-5.9
Octanol/water partition coefficient as log Pow: 3.35  

Naphthalene, a polycyclic aromatic hydrocarbon, may exist as white crystalline plates, balls, or powder, and has a distinctive mothball odour.
Naphthalene occurs naturally in fossil fuels and is a combustion product of organic material. 
Naphthalene has several industrial uses, primarily as a chemical intermediate.

Naphthalene may also be referred to as naphthalin or white tar.There are numerous other synonyms and product names; see Hazardous Substances Data Bank (HSDB) for more information.

Naphthalene is the major ingredient found in traditional mothballs, and its stinks partly of tar. 

Naphthalene is a white solid chemical that vaporizes easily. 
Naphthalene has a strong smell. 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.

Chemical Properties    
Naphthalene is a crystalline, white, flammable, polycyclic aromatic hydrocarbon consisting of two fused benzene rings. 
Naphthalene 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.

Uses    
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. 
Naphthalene was used in preparation of carbon-coated Si 70 Sn 30 nanoparticles.
Naphthalene was used as fluorescent probe to study the aggregation behavior of sodium cholate.
Naphthalene 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.

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. 
Naphthalene 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. 
Naphthalene 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. 
Naphthalene 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. 
Naphthalene 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.

Uses    
Naphthalene occurs naturally in fossil fuels such as coal and petroleum. 
Naphthalene 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).

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.

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.

Naphthalene is an abundant polycyclic aromatic hydrocarbon that is persistent, bioaccumulative, toxic and found in tobacco smoke and urban air.

IUPAC names
Bicyclo[4.4.0]deca-1,3,5,7,9-pentene
bicyclo[4.4.0]deca-1,3,5,7,9-penten
Naphtalene
naphtalene
NAPHTHALENE
Naphthalene
naphthalene
Naphthalene
naphthalene
Naphthalene Zone Refined (number of passes:23)
NAPHTHALENE, PURE
Naphthalin
Napthalene
napthalene
white tar, camphor tar, naphthalin, naphthaline, antimite, albocarbon, hexalene, mothballs, moth flakes

SYNONYMS:
Naphthalene [ACD/Index Name] [ACD/IUPAC Name] [Wiki]
1421310 [Beilstein]
202-049-5 [EINECS]
91-20-3 [RN]
Albocarbon
MFCD00001742 [MDL number]
Naftaleen [Dutch]
Naftalen [Polish]
Naftalene [Italian]
naftaleno [Spanish]
Naftalin [Turkish]
Naftalina [Spanish]
Naftalina [Portuguese]
Naphtalène [French] [ACD/IUPAC Name]
naphtaline [French]
Naphthalen [German]
Naphthalin [German] [ACD/IUPAC Name]
Naphthaline
tar camphor
White tar
Ναφθαλίνιο [Modern Greek (1453-)]
Нафталин [Russian]
ナフタレン [Japanese]
Moth balls
Mothballs
(1,2,3,4-2H4)Naphthalene
1,2,3,4,5,6,7-Heptadeuterionaphthalene
1177098-90-6 [RN]
19796-93-1 [RN]
202-049-5MFCD00001742
39600-31-2 [RN]
http://www.hmdb.ca/metabolites/HMDB0029751
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16482
L66J [WLN]
Melting Pointmissing
Moth Flakes
Naphthalene 10 µg/mL in Acetonitrile
Naphthalene 10 µg/mL in Cyclohexane
Naphthalene 10 µg/mL in Acetonitrile
Naphthalene 10 µg/mL in Cyclohexane
Naphthalene 100 µg/mL in Acetonitrile
Naphthalene 100 µg/mL in Methanol
Naphthalene 100 µg/mL in Acetonitrile
Naphthalene 100 µg/mL in Methanol

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