Phenol

 

Phenol

Chemical formula	C6H5OH
OTP appearance	white crystalline solid
Index of refraction	1.5425
Molar Mass(g/mol)	94.11
Density(g/cc)	1.07
Melting Point(°C)	40.5
Boiling Point(°C)	181.7
Solubility in water(g/L)	83
NFPA 704	2 3 0 COR

Uses

Justification Questioned

Other

• Cleaning
• Antiseptic
• Naturally occurring, easily obtainable aromatic compound for organic syntheses, e.g. 2,6-xylenol.

Natural occurrence

• Phenol occurs naturally in tars and crude oil

Hazards

• Toxic
• Flammable
• Corrosive

Production

Extraction

cf wood distillation

Coal Tar

1. distill coal tar and retain what distills between 170° and 230°C
2. redistill and retain what distills between 180°C and 183°C

Synthesis

• From salicylic acid via thermal decomposition

  C₇H₆O₃(s)

  {

  →

  145-165°C}

  C₆H₅OH(l) + CO₂(g)

• From benzene via sulfuric acid and sodium hydroxide

  C₆H₆ + H₂SO₄ → C₆H₅SO₃H + H₂O

  C₆H₅SO₃H + 2 NaOH → C₆H₅OH + Na₂SO₃ + H₂O

• From benzene via Fenton's reagent:

  c6 h6  + H₂O₂ + FeSO₄ → C₇H₅OH

• From benzene and nitrous oxide

  C₆H₆ + N₂O → C₆H₅OH + NO

• From oxidation of toluene (DOW Chemical process)

  C₆H₅CH₃ + 2 O₂ → C₆H₅OH + CO₂ + H₂O