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 (DMP). It is a colorless solid.

2,6-Xylenol[1]
2,6-Xylenol molecule
Names
Preferred IUPAC name
2,6-Dimethylphenol
Other names
2-Hydroxy-m-xylene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.547
UNII
  • InChI=1S/C8H10O/c1-6-4-3-5-7(2)8(6)9/h3-5,9H,1-2H3 ☒N
    Key: NXXYKOUNUYWIHA-UHFFFAOYSA-N ☒N
  • InChI=1/C8H10O/c1-6-4-3-5-7(2)8(6)9/h3-5,9H,1-2H3
    Key: NXXYKOUNUYWIHA-UHFFFAOYAM
  • CC1=C(C(=CC=C1)C)O
Properties
C8H10O
Molar mass 122.167 g·mol−1
Appearance white solid
Density 1.132 g/cm3
Melting point 43 to 45 °C (109 to 113 °F; 316 to 318 K)
Boiling point 203 °C (397 °F; 476 K)
Hazards
Flash point 86 °C (187 °F; 359 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

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:[2][3]

C6H5OH + 2 CH3OH → (CH3)2C6H3OH + 2 H2O

Challenges associated with the production is the similarity of the boiling points of cresols and this xylenol.

Reactions

2,6-Xylenol is susceptible to oxidative coupling leading to polymers and dimers.[4]

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.[2]

Toxicity

Its LD50 (oral, rats) ranges from 296-1750 mg/kg.[2]

References
  1. 2,6-Xylenol at Sigma-Aldrich
  2. Fiege, Helmut (2000). "Cresols and Xylenols". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_025. ISBN 3527306730.
  3. Zukowski, W.; Berkowicz, G.; Baron, J.; Kandefer, S.; Jamanek, D.; Szarlik, S.; Wielgosz, Z.; Zielecka, M. (2014). "Selective phenol methylation to 2,6-dimethylphenol in a fluidized bed of iron-chromium mixed oxide catalyst with o-cresol circulation" (PDF). Chemistry Central Journal. 8 (1): 51. doi:10.1186/s13065-014-0051-6. PMC 4172955. PMID 25342964.
  4. Selective oxidative para C–C dimerization of 2,6-dimethylphenol Christophe Boldron, Guillem Aromí, Ger Challa, Patrick Gamez and Jan Reedijk Chemical Communications, 2005, (46), 5808 - 5810 Abstract
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