Naphthalene

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NAPHTHALENE

~ also known as Naphthene; 91-20-3; Naphthalin; Camphor tar; Tar camphor; etc. is the simplest polycyclic aromatic hydrocarbon. It is a white crystalline solid and has a strong mothball odor. Naphthalene is gotten from either petroleum distillation or coal tar, and is mainly used to manufacture phthalic anhydride. The global naphthalene market was USD 1.53 Billion in 2017 and is estimated to reach USD 1.85 Billion by 2022, at a CAGR of 3.8% between the years 2017 and 2022.
Chemical structure: Naphthalene is an organic compound with chemical formula C10H8. Naphthalene is an aromatic hydrocarbon and its structure consists of a fused pair of benzene rings.
Properties: Naphthalene is a white crystalline volatile solid and has a strong coal-tar odor. The solid is insoluble in water. It burns, but can be difficult to ignite. The molten form is very hot. Naphthalene has a boiling point of 424° F at 760 mm Hg. When heated to decomposition, it emits pungent smoke and irritating fumes.
Production: 
  1. Most naphthalene is obtained from coal tar. It can be produced from primary tar distillation with the naphthalene fraction boiling between 210 and 220ºC. This process produces a yield in excess of 90%. Additional refining necessitates separation of the co-boiling compounds (nitrogen bases, benzo(b)thiophene, phenols, and other aromatic hydrocarbons).
  2. From the 1960s through 1990s, large amounts of naphthalene were produced from heavy petroleum fractions during the refining of petroleum, but today, only a minor component of naphthalene are obtained from petroleum.
  3. Apart from coal tar, small amounts of naphthalene are produced by certain species of deer, magnolias, and the Formosan subterranean termites.
  4. Certain strains of the endophytic fungus, Muscodor albus, produce naphthalene along with a range of volatile organic compounds, whereas Muscodor vitigenus almost exclusively produces naphthalene.
Chemical reactions and Uses: Naphthalene is majorly used in the production of phthalic anhydride. Nevertheless, o-xylene is substituting naphthalene as the preferred raw material for the production phthalic anhydride.
Other uses of naphthalene include moth repellent, carbamate insecticides, synthetic tanning agent, surface active agents and resins, dye intermediate, and in various organic chemicals.
The major commercial uses are in the agricultural chemical industry that uses Alkyl naphthalene sulfonates (ANS) for wettable granular and wettable powder formulations, and the fabric and textile industry, which uses the wetting properties of ANS for bleaching and dyeing processes.
In the Laboratory, molten naphthalene provides an outstanding medium for poorly soluble aromatic compounds. In numerous cases, it works more than other high-boiling solvents, such as nitrobenzene, dichlorobenzene, benzonitrile, and durene.
Skin contact must be avoided as the vapors given off by the material may be toxic.
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