2,6-Xylenol


2,6-Xylenol is a chemical compound which is one of the six isomers of xylenol. It is also commonly known as 2,6-dimethylphenol. It is a colorless solid.

Production

2,6-DMP is produced by the methylation of phenol. With production >100,000 tons/y, it is the most important xylenol. The methylation is carried out by contacting gaseous phenol and methanol at elevated temperatures in the presence of a solid acid catalyst:
Challenges associated with the production is the similarity of the boiling points of cresols and this xylenol.

Reactions

Acid-catalyzed condensation of 2,6-xylenol gives tetramethylbisphenol A. An analogue of bisphenol A, this bisphenol is used in the production of some polycarbonates. 2,6-Xylenol reacts with ammonia to give 2,6-dimethylaniline.
The antiseptic chloroxylenol is produced by chlorination of this xylenol.
2,6-Xylenol is susceptible to oxidative coupling leading to polymers and dimers.

Toxicity

Its LD50 ranges from 296-1750 mg/kg.