Naphthalene
- CAS No.
- 91-20-3
- Chemical Name:
- Naphthalene
- Synonyms
- NAPTHALENE;naphtalene;NAPHTHENE;NAPHTHALIN;CRUDE NAPHTHALENE;1-NAPHTHALENE;White tar;Albocarbon;Naphthaline;NAPHTHALENE FLAKES
- CBNumber:
- CB2472212
- Molecular Formula:
- C10H8
- Molecular Weight:
- 128.17
- MOL File:
- 91-20-3.mol
- Modify Date:
- 2024/5/8 16:13:07
| 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. | Store below +30°C. |
| solubility | methanol: soluble50mg/mL, clear, colorless |
| form | Faint beige to brown to salmon red powder |
| color | White to almost white |
| Specific Gravity | 1.145 |
| Odor | at 10.00 % in benzyl benzoate. pungent dry tarry |
| Odor Type | pungent |
| explosive limit | 0.9-5.9%(V) |
| Water Solubility | 30 mg/L (25 ºC) |
| Merck | 14,6370 |
| BRN | 1421310 |
| 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. |
| Dielectric constant | 2.5（85℃） |
| InChIKey | UFWIBTONFRDIAS-UHFFFAOYSA-N |
| LogP | 3.7 at 25℃ |
| CAS DataBase Reference | 91-20-3(CAS DataBase Reference) |
| IARC | 2B (Vol. 82) 2002 |
| NIST Chemistry Reference | Naphthalene(91-20-3) |
| EPA Substance Registry System | Naphthalene (91-20-3) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |     GHS02,GHS07,GHS08,GHS09 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H228-H302-H351-H410 | |||||||||
| Precautionary statements | P202-P210-P240-P273-P301+P312-P308+P313 | |||||||||
| 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 | |||||||||
| OEB | A | |||||||||
| OEL | TWA: 10 ppm (50 mg/m3), STEL: 15 ppm (75 mg/m3) | |||||||||
| RIDADR | UN 1334 4.1/PG 3 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | QJ0525000 | |||||||||
| Autoignition Temperature | 978 °F | |||||||||
| TSCA | Yes | |||||||||
| HazardClass | 4.1 | |||||||||
| PackingGroup | III | |||||||||
| HS Code | 29029010 | |||||||||
| Toxicity | Acute oral LD50 for guinea pigs 1,200 mg/kg, mice 533 mg/kg, rats 1,250 mg/kg (quoted, RTECS, 1985). | |||||||||
| IDLA | 250 ppm | |||||||||
| NFPA 704 |
|
Naphthalene price More Price(38)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | PHR1275 | Naphthalene Pharmaceutical Secondary Standard; Certified Reference Material | 91-20-3 | 1G | ₹7716.53 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | CRM48641 | Naphthalene solution certified reference material, 200?μg/mL in methanol | 91-20-3 | 1PKG | ₹2872.8 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 84679 | Naphthalene analytical standard | 91-20-3 | 250MG | ₹2209.13 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 91489 | Naphthalene certified reference material, TraceCERT? | 91-20-3 | 100MG | ₹9524.93 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 84679 | Naphthalene analytical standard | 91-20-3 | 1G | ₹4099.73 | 2022-06-14 | Buy |
Naphthalene Chemical Properties,Uses,Production
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. 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.
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.
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.
General Description
Heterogeneous ozonolysis of naphthalene adsorbed on XAD-4 resin has been studied using annular denuder technique.
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 carcinogen.
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
G6PD deficiency.
Carcinogenicity
Naphthalene is reasonably anticipated to be a human carcinogenbased on sufficient evidence from studies in experimental animals.
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.
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.
References
Formation Mechanisms of Naphthalene and Indene: From the Interstellar Medium to Combustion Flames. DOI:10.1021/acs.jpca.6b09735
Functional Naphthalene Diimides: Synthesis, Properties, and Applications. DOI:10.1021/ACS.CHEMREV.6B00160
The 100 Most Important Chemical Compounds: A Reference Guide DOI:10.5860/choice.45-3798
A comprehensive guide to the hazardous properties of chemical substances DOI:10.1002/9780470134955
A Dictionary of Chemistry (6th edition) DOI:10.1108/09504120910935291
TOXICOLOGICAL REVIEW of NAPHTHALENE
Naphthalene - Environmental Protection Agency
Naphthalene Preparation Products And Raw materials
Raw materials
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