Naphthalene
CAS NO: 91-20-3
Chemical formula: C10H8
Molar mass: 128.174 g·mol−1
EC Number: 202-049-5
APPLICATIONS
Uses of Naphthalene:
General arts and crafts or office supplies which can not be classified into a more refined category.
Glue sticks, glitter glues, fabric glues, craft glue, spray mounts, stencil sprays, and other adhesives used for primarily craft purposes
Cleaning products for general household cleaning, which do not fit into a more refined category
Products used to clean glass, mirrors, and windows
Materials used for construction (e.g. flooring, tile, sinks, bathtubs, mirrors, wall materials/drywall, wall-to-wall carpets, insulation, playground surfaces); includes semi-permanent fixtures such as faucets and light fixtures
Items used to furnish a home or workplace, e.g. tables, chairs, sofa, outdoor patio furniture, sofa cover, hammock, mattress, area rug
Products for removing grease and other hydrophobic materials from hard surfaces
Paint or stain related products that do not fit into a more refined category
Oil or solvent-based home improvement paints
Home improvement paints, excluding or not specified as oil-, solvent-, or water-based paints
Paints applied to hard surfaces that are intended to be painted over and that improve adhesion, coverage, or prevent the bleeding through of stains
Products for coating and protecting household surfaces other than glass, stone, or grout
Products used to control or kill unwanted plants
Products used to control fungi pests in the garden or home
Insecticides, for interior or exterior use
Pesticides orally administered, worn (e.g. collars), or applied to the skin, fur, etc. of pets; including flea/tick collars, excluding pesticidal shampoos
Power steering fluids, transmission fluids, brake fluids, fuel injector cleaners, gas treatments, or leak stoppers
Petroleum-based or synthetic engine lubricants
Naphthalene is produced from petroleum or coal tars.
Further, Naphthalene is used mainly as an intermediate in the synthesis of organic chemicals (plastics, insecticides, fungicides, etc.).
Naphthalene has been used as a household moth repellent. [ACGIH] Naphthalene is produced from incomplete combustion, e.g., burning fossil fuels, forest fires, and smoking cigarettes.
Naphthalene is present in jet and diesel fuel.
The use of Naphthalene as a moth repellent has decreased since the introduction of p-dichlorobenzene.
Naphthalene is one of the major components of creosote, and the highest concentrations in industrial environments occur in workplaces producing creosote-impregnated timbers.
Moreover, Naphthalene is registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses.
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, Naphthalene is used around garden and building peripheries to repel animals such as snakes and rabbits.
Naphthalene is used mainly as a precursor to derivative chemicals.
The single largest use of Naphthalene is the industrial production of phthalic anhydride, although more phthalic anhydride is made from o-xylene.
Industrially, Naphthalene is used in the production of phthalic anhydride, as a solvent for chemical reactions, as a wetting agent and as a fumigant.
Naphthalene is produced industrially via coal tar and naturally with trace amounts of naphthalene being produced by black walnuts, magnolias and specific types of deer.
Industrial uses of Naphthalene:
Agricultural chemicals (non-pesticidal)
Corrosion inhibitor
Fuels and fuel additives
Intermediates
Laboratory chemicals
Not Known or Reasonably Ascertainable
Paint additives and coating additives not described by other categories
Pigment
Processing aids, not otherwise listed
Processing aids, specific to petroleum production
Solvents (which become part of product formulation or mixture)
Surface active agents
Naphthalene is formerly important in dyestuff manufacture.
Moreover, Naphthalene acts as a precursor to phthalic anhydride.
Naphthalene is used in the manufacturing of phthalic anhydride, naphthalene sulfonic acids and hydrogenated naphthalenes such as 1,2,3,4-tetrahydronaphthalene, which is used as a precursor for various dyestuffs, pigments, rubber processing chemicals and in pharmaceuticals.
The molten form of Naphthalene is used as solvent replacing the high- boiling solvents like dichlorobenzene, nitrobenzene and durene.
Naphthalene is involved as reaction medium for in the Diels-Alder reaction between C60 with anthracene.
Some uses based on different categories:
Fumigant:
Naphthalene has been used as a fumigant.
It 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 insects and animals such as opossums, and in museum storage-drawers and cupboards to protect the contents from attack by insect pests.
Solvent:
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.
Derivative uses:
The single largest use of naphthalene is the production of phthalic anhydride, which is an intermediate used to make plasticizers for polyvinyl chloride, and to make alkyd resin polymers used in paints and varnishes.
Sulfonic acids and sulfonates:
Naphthalenes and sulfonates are useful.
Naphthalenesulfonic acids are used in the synthesis of 1-naphthol and 2-naphthol, precursors for various dyestuffs, pigments, rubber processing chemicals and other chemicals and pharmaceuticals.
They are also used as dispersants in synthetic and natural rubbers, in agricultural pesticides, in dyes, and in lead–acid battery plates. Naphthalene is used as precursor and to form pharmaceutical salts such as CFT.
The aminonaphthalenesulfonic acids are precursors for synthesis of many synthetic dyes.
Naphthalene is used in many industrial applications as nondetergent surfactant (wetting agent) that effectively disperse colloidal systems in aqueous media.
The major commercial applications of Naphthalene are in the agricultural chemical industry, which uses ANS for wettable powder and wettable granular (dry-flowable) formulations, and in the textile and fabric industry, which uses the wetting and defoaming properties of ANS for bleaching and dyeing operations.
Naphthalene is a superplasticizer used for the production of high strength concrete.
They are produced by treating naphthalenesulfonic acid with formaldehyde, followed by neutralization with sodium hydroxide or calcium hydroxide.
Other derivative uses of Naphthalene:
Many azo dyes are produced from naphthalene.
Useful agrichemicals include naphthoxyacetic acids.
Hydrogenation of naphthalene gives tetrahydronaphthalene (tetralin) and decahydronaphthalene (decalin), which are used as low-volatility solvents.
Naphthalene is used as a hydrogen-donor solvent.
Alkylation of naphthalene with propylene gives a mixture of diisopropylnaphthalenes, which are useful as nonvolatile liquids for inks.
Substituted napthalenes serve as pharmaceuticals such as propranolol (a beta blocker) and nabumetone (a nonsteroidal anti-inflammatory drug).
Other uses of Naphthalene:
Several uses stem from naphthalene's high volatility: it is used to create artificial pores in the manufacture of high-porosity grinding wheels; it is used in engineering studies of heat transfer using mass sublimation; and it has been explored as a sublimable propellant for cold gas satellite thrusters.
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 present-day production is mainly from coal tar. Approximately 1.3M tons are produced annually.
Naphthalene is the most abundant single component of coal tar.
The composition of coal tar varies with coal type and processing, but typical coal tar is about 10% naphthalene by weight.
In industrial practice, distillation of coal tar yields an oil containing about 50% naphthalene, along with twelve other aromatic compounds.
This oil, after being washed with aqueous sodium hydroxide to remove acidic components (chiefly various phenols), and with sulfuric acid to remove basic components, undergoes fractional distillation to isolate naphthalene.
The crude naphthalene resulting from this process is about 95% naphthalene by weight.
The chief impurities are the sulfur-containing aromatic compound benzothiophene (< 2%), indane (0.2%), indene (< 2%), and methylnaphthalene (< 2%).
Petroleum-derived naphthalene is usually purer than that derived from coal tar. Where required, crude naphthalene can be further purified by recrystallization from any of a variety of solvents, resulting in 99% naphthalene by weight, referred to as 80 °C (melting point).
Naphthalene and its alkyl homologs are the major constituents of creosote.
Trace amounts of naphthalene are produced by magnolias and some species of deer, as well as the Formosan subterranean termite, possibly produced by the termite as a repellant against ants, poisonous fungi and nematode worms.
Some strains of the endophytic fungus Muscodor albus produce naphthalene among a range of volatile organic compounds, while Muscodor vitigenus produces naphthalene almost exclusively.
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.
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.
Moth balls containing naphthalene are generally safe for use around adults and older children, if used correctly and in the right quantity.
Australian guidelines recommend that the use of naphthalene is restricted around children under three years of age.
This means that children's blankets and clothes should not be stored with mothballs containing naphthalene, and moth balls should not be used in young children's rooms or in areas where young children may be present or have access to.
If children's blankets and clothing have inadvertently been stored with naphthalene moth balls, they should be aired outdoors to remove any odour and washed before they are used.
Naphthalene can be very dangerous if moth balls are eaten, so it is especially important that mothballs are stored well out of the reach of small children and pets.
Additionally, if you or one of your direct family members has been diagnosed with a genetic disorder of the blood, products containing naphthalene should be avoided.
The main uses of naphthalene are discussed below:
Naphthalene is used in making carbaryl drugs.
These drugs are used in making insecticides.
Naphthalene is used in making nadoxolol drug for beta-blocking.
The Sulphonated form of naphthalene is used as a surfactant.
Naphthalene is used in making synthetic dyes.
Amino naphthalene sulfonic acid is used in making different types of dyes.
Molten naphthalene is used for making solvents for an aromatic compound.
DESCRIPTION
Naphthalene is the simplest of the fused or condensed ring hydrocarbon compounds composed of two benzene rings sharing two adjacent carbon atoms.
The chemical formula of Naphthalene is 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.
Further, 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.
Moreover, Naphthalene is highly volatile and has a characteristic odour.
Naphthalene has been used as moth repellent.
Some moth balls and toilet deodorant cakes contain a substance called naphthalene.
Naphthalene is a solid, white material with a distinctive odour, and it is found naturally in fossil fuels like coal and oil.
Naphthalene is an organic compound with formula C10H8.
Furthermore, 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.
The physical properties and chemical properties of naphthalene are discussed below:
Naphthalene exists in crystalline form.
Naphthalene is generally white in color. It is also found in transparent to brownish color.
The molecular weight of naphthalene is 128.18 g/mol.
Naphthalene is insoluble in water at normal room temperature.
Naphthalene has an aromatic odor.
The vapor pressure of naphthalene is 0.087 mmHg.
In its chemical behaviour, naphthalene shows the aromatic character associated with benzene and its simple derivatives.
Reactions of Naphthalene are mainly reactions of substitution of hydrogen atoms by halogen atoms, nitro groups, sulfonic acid groups, and alkyl groups.
Large quantities of naphthalene are converted to naphthylamines and naphthols for use as dyestuff intermediates.
For many years napthalene was the principal raw material for making phthalic anhydride.
Synthesis of Naphthalene:
From Coal Tar:
Naphthalene can be obtained from the coaltar, by making naphthalene crystals.
These crystals can be formed by the middle oil fraction.
The crystals produced in this process are subjected to sulphuric acid for the purification process.
In the end, pure naphthalene crystals are formed.
Haworth Synthesis:
In this process, benzene to naphthalene is produced.
The benzene ring is first subjected to the acylation process.
This reaction starts with the Friedel craft Acylation of a benzene ring with the succinic anhydride, then a series of reduction reactions undergo.
Finally, a naphthalene molecule is produced by dehydrogenation.
Naphthalene is made from crude oil or coal tar.
More to that, 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.
Moreover, Naphthalene is an organic compound.
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.
In the early 1820s, two separate reports described a white solid with a pungent odor derived from the distillation of coal tar.
In 1821, John Kidd cited these two disclosures and then described many of this substance's properties and the means of its production.
He proposed the name naphthaline, as it had been derived from a kind of naphtha (a broad term encompassing any volatile, flammable liquid hydrocarbon mixture, including coal tar).
Naphthalene's chemical formula was determined by Michael Faraday in 1826.
The structure of two fused benzene rings was proposed by Emil Erlenmeyer in 1866, and confirmed by Carl Gräbe three years later.
A 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).
Because of this resonance, the molecule of Naphthalene has bilateral symmetry across the plane of the shared carbon pair, as well as across the plane that bisects bonds C2-C3 and C6-C7, and across the plane of the carbon atoms.
Thus there are two sets of equivalent hydrogen atoms: the alpha positions, numbered 1, 4, 5, and 8, and the beta positions, 2, 3, 6, and 7. Two isomers are then possible for mono-substituted naphthalenes, corresponding to substitution at an alpha or beta position.
Pure crystalline naphthalene is a moderate insulator at room temperature, with resistivity of about 1012 Ω m.
The resistivity drops more than a thousandfold on melting, to about 4 × 108 Ω m.
Both in the liquid and in the solid, the resistivity depends on temperature as ρ = ρ0 exp(E/(k T)), where ρ0 (Ω m) and E (eV) are constant parameters, k is Boltzmann's constant (8.617×10−5 eV/K), and T is absolute temperature (K).
The parameter E is 0.73 in the solid. However, the solid shows semiconducting character below 100 K.[21][22]
In electrophilic aromatic substitution reactions, naphthalene reacts more readily than benzene.
For example, chlorination and bromination of naphthalene proceeds without a catalyst to give 1-chloronaphthalene and 1-bromonaphthalene, respectively.
Likewise, whereas both benzene and naphthalene can be alkylated using Friedel–Crafts reactions, naphthalene can also be easily alkylated by reaction with alkenes or alcohols, using sulfuric or phosphoric acid catalysts.
In terms of regiochemistry, electrophiles attack at the alpha position.
The selectivity for alpha over beta substitution can be rationalized in terms of the resonance structures of the intermediate: for the alpha substitution intermediate, seven resonance structures can be drawn, of which four preserve an aromatic ring.
For beta substitution, the intermediate has only six resonance structures, and only two of these are aromatic.
Sulfonation gives the "alpha" product naphthalene-1-sulfonic acid as the kinetic product but naphthalene-2-sulfonic acid as the thermodynamic product.
Naphthalene appears as a white crystalline volatile solid with a strong coal-tar odor.
Naphthalene is denser than water and insoluble in water.
Naphthalene burns, but may be difficult to ignite.
In the molten form Naphthalene is very hot.
Exposure to skin must be avoided.
Also the vapors given off by Naphthalene may be toxic.
Naphthalene is used as a moth repellent, fumigant, lubricants, and to make other chemicals, and for many other uses
PROPERTIES
Molecular Weight: 128.17
XLogP3: 3.3
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Rotatable Bond Count: 0
Exact Mass: 128.062600255
Monoisotopic Mass: 128.06260025
Topological Polar Surface Area: 0 Ų
Heavy Atom Count: 10
Formal Charge: 0
Complexity: 80.6
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Melting Point: 81 °C
Boiling Point: 218 °C
Solubility in water: Insoluble
Degree of solubility in water: 31 mg/l 25 °C
Solubility (very soluble in): Ether
Solubility (soluble in): Benzene,Alcohol,Chloroform,Toluene
FIRST AID
General information:
Symptoms of poisoning may occur even after several hours; therefore medical observation for at least 48 hours after the accident is recommended.
After inhalation:
Supply fresh air; consult doctor in case of complaints.
After skin contact:
Immediately wash with water and soap and rinse thoroughly.
After eye contact:
Rinse opened eye for several minutes under running water.
After swallowing:
Rinse mouth.
Do not induce vomiting.
Call for a doctor immediately.
HANDLING AND STORAGE
Precautions for safe handling:
Store in cool, dry place in tightly closed receptacles.
Information about fire - and explosion protection:
The product is not flammable.
Conditions for safe storage, including any incompatibilities:
Storage:
Store in a cool location.
Please refer to the manufacturer's certificate for specific storage and transport temperature conditions.
Requirements to be met by storerooms and receptacles:
Store only in the original receptacle.
Keep container in a well-ventilated place.
Keep away from sources of ignition and heat.
Information about storage in one common storage facility:
Store away from foodstuffs.
Further information about storage conditions:
None.
Specific end use(s):
No further relevant information available.
SYNONYMS
naphthalene
91-20-3
Naphthalin
Tar camphor
White tar
Albocarbon
Naphthene
Camphor tar
Naphthaline
Moth flakes
Moth balls
naphtalene
Dezodorator
Naftalen
Mighty 150
napthalene
Naphthalinum
RCRA waste number U165
Mighty RD1
naftaleno
Mothballs
NCI-C52904
naftalina
naphtaline
naphthalen
NSC 37565
NSC-37565
CHEMBL16293
CHEBI:16482
2166IN72UN
Naphthalene, 99%
MFCD00001742
NCGC00090793-02
DSSTox_CID_913
DSSTox_RID_75860
DSSTox_GSID_20913
Naftalen [Polish]
Naphthalene, analytical standard
Caswell No. 587
Naphtalinum
Naphthalene [BSI:ISO]
Naphtalene [ISO:French]
Naphthalene, pure
CAS-91-20-3
Naphthalene, molten
CCRIS 1838
HSDB 184
Naphthalene (molten)
EINECS 202-049-5
UN1334
UN2304
RCRA waste no. U165
EPA Pesticide Chemical Code 055801
Dezodorator, Whitetar,Naphthalene, NSC 37565, Tar camphor, Albocarbon, Naphthene, Moth flakes
NAPHTHALENE (1,2,3,4,5,6,7,8-D8)
Naphthalene, crude or refined
UNII-2166IN72UN
AI3-00278
2-naphthalen
1-Naphthalene
2-Naphthalene
Naphthalene,(S)
Naphthalene, 98%
Naphthalene, di-C5-6-alkyl derivs.
NAPHTHALENE [MI]
NAPHTHALENE [ISO]
NAPHTHALENE [HSDB]
NAPHTHALENE [IARC]
EC 202-049-5
NAPHTHALINUM [HPUS]
NAPHTHALENE [MART.]
NAPHTHALENE [USP-RS]
NAPHTHALENE [WHO-DD]
MLS001055498
WLN: L66J
BIDD:ER0665
DTXSID8020913
HMS3039N15
ZINC967522
AMY22299
NSC37565
Tox21_111023
Tox21_202004
Tox21_300008
BDBM50159249
Naphthalene, for synthesis, 98.5%
STL282720
AKOS000119977
Naphthalene 100 microg/mL in Methanol
UN 1334
UN 2304
Naphthalene 10 microg/mL in Cyclohexane
NCGC00090793-01
NCGC00090793-03
NCGC00090793-04
NCGC00090793-05
NCGC00254058-01
NCGC00259553-01
68412-25-9
BS-22320
Naphthalene 10 microg/mL in Acetonitrile
SMR000677944
Naphthalene 100 microg/mL in Acetonitrile
Naphthalene, SAJ first grade, >=98.0%
Bicyclo[4.4.0]deca-1,3,5,7,9-pentene
FT-0651884
FT-0672611
FT-0672612
N0004
N0885
EN300-21626
C00829
D97670
Naphthalene, suitable for scintillation, >=99%
L001166
Naphthalene, molten [UN2304] [Flammable solid]
Q179724
SR-01000854997
Melting point standard 79-81C, analytical standard
SR-01000854997-2
F0001-2217
Naphthalene, certified reference material, TraceCERT(R)
Z104506008
Naphthalene, crude or refined [UN1334] [Flammable solid]
Naphthalene solution, 100 ng/muL in cyclohexane, analytical standard
Naphthalene, United States Pharmacopeia (USP) Reference Standard
Naphthalene solution, certified reference material, 200 mug/mL in methanol
Naphthalene solution, certified reference material, 5000 mug/mL in methanol
Naphthalene, Pharmaceutical Secondary Standard; Certified Reference Material
25135-16-4
72931-45-4
