2,6-Xylenol

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 (oral, rats) ranges from 296-1750 mg/kg.

References

References

1. [http://www.sigmaaldrich.com/catalog/ProductDetail.do?N4=W324906|ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC 2,6-Xylenol] at [[Sigma-Aldrich]]
2. (2000). "Ullmann's Encyclopedia of Industrial Chemistry".
3. (2014). "Selective phenol methylation to 2,6-dimethylphenol in a fluidized bed of iron-chromium mixed oxide catalyst with o-cresol circulation". Chemistry Central Journal.
4. (2017). "Iron(III)-Catalyzed Chlorination of Activated Arenes". The Journal of Organic Chemistry.
5. ''Selective oxidative para C–C dimerization of 2,6-dimethylphenol'' Christophe Boldron, Guillem Aromí, [[Ger Challa]], Patrick Gamez, Jan Reedijk [[Chemical Communications]], '''2005''', (46), 5808 - 5810 [http://www.rsc.org/publishing/journals/CC/article.asp?doi=b510378a Abstract]