|Jmol-3D images||Image 1|
|Appearance||colorless prismatic crystals|
|Melting point||35.5 °C; 95.9 °F; 308.6 K|
|Boiling point||201.8 °C; 395.2 °F; 474.9 K|
|Solubility in water||2.4 g/100 ml at 40 °C
5.3 g/100 ml at 100 °C
|Solubility in ethanol||fully miscible|
|Solubility in diethyl ether||fully miscible|
|Refractive index (nD)||1.5395|
|R-phrases||R34 R24 R25|
|S-phrases||S36 S37 S39 S45|
|Main hazards||May be fatal if swallowed, inhaled, or absorbed through skin.|
|Flash point||86.1 °C; 187.0 °F; 359.2 K|
|Related phenols||o-cresol, m-cresol, phenol|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C or 77 °F, 100 kPa)
p-Cresol is an organic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol, an isomer of o-cresol and m-cresol.
Together with many other compounds, p-cresol is traditionally extracted from coal tar, the volatilized materials obtained in the roasting of coal to produce coke. This residue contains a few percent by weight of phenol and cresols. p-Cresol it is currently prepared industrially mainly by a two step route beginning with the sulfonation of toluene:
- CH3C6H5 + H2SO4 → CH3C6H4SO3H + H2O
Base hydrolysis of the sulfonate salt gives the sodium salt of the cresol:
- CH3C6H4SO3Na + 2 NaOH → CH3C6H4OH + Na2SO3 + H2O
Other methods for the production of p-cresol include chlorination of toluene followed by hydrolysis. In the cymene-cresol process, phenol is alkylated with propylene to give p-cymene, which can be oxidatively dealkylated.
p-Cresol is mainly consumed in the production of antioxidants, e.g., butylated hydroxytoluene (BHT). The monoalkylated derivatives undergo coupling to give extensive family of diphenol antioxidants. These antioxidants are valued because they are relatively low in toxicity and nonstaining.
- Helmut Fiegein "Cresols and Xylenols" in Ullmann's Encyclopedia of Industrial Chemistry" 2007; Wiley-VCH, Weinheim. doi:10.1002/14356007.a08_025
- Physiological Correlates of Musth: Lipid Metabolites and Chemical Composition of Exudates. L.E.L Rasmussen and Thomas E Perrin, Physiology & Behavior, October 1999, Volume 67, Issue 4, Pages 539–549, doi:10.1016/S0031-9384(99)00114-6
- Musth in elephants. Deepa Ananth, Zoo's print journal, 15(5), pages 259-262 (article)
- Williams, Norris H. & Whitten, W. Mark (1983) "Orchid floral fragrances and male euglossine bees: methods and advances in the last sesquidecade" Biol. Bull. 164: 355-395.