Difference between revisions of "Naphthalene"

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Naphthalene is an organic compound with the chemical formula C₁₀H₈. It is the simplest polycyclic aromatic hydrocarbon.

Properties

Chemical

Naphthalene can react with halogens, such as chlorine to form 1-chloronaphthalene, without requiring a catalyst, unlike in the case of benzene. Likewise, whereas both benzene and naphthalene can be alkylated using Friedel–Crafts reactions, naphthalene can also be alkylated by reaction with alkenes or alcohols, with sulfuric or phosphoric acid as the catalyst.

Physical

Naphthalene is a white crystalline solid with a characteristic odor that is detectable at low concentrations. It is insoluble in water, but soluble in other organic solvents, especially closer to their boiling point.

Availability

Some mothballs, especially the older types tend to contain naphtalene, the exact concentration depending on the product. Naphthalene can be extracted via sublimation. Always check the label, as most common mothballs contain 1,4-dichlorobenzene.

Naphthalene and 1,4-dichlorobenzene are never found together, as they react.

Mothballs and other products containing naphthalene have been banned within the EU since 2008.

Preparation

Naphthalene can be extracted from coal tar, via sublimation and purification.

Projects

• Phtalic anhydride synthesis
• Dialin synthesis

Handling

Safety

Naphthalene is known to to be toxic to red blood cells and it's considered a possible carcinogenic.

Storage

Naphthalene should be stored in hermetic sealed bottles and kept in a cold place as it will slowly sublime and deposit on the cap interior.

Disposal

Naphthalene can be safely burned.

References

Relevant Sciencemadness threads

• Naphthalene Reactions
• solubility of naphthalene in acetone
• When naphthalene balls aren’t naphthalene balls(?)