2,6-Xylenol
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Names | |
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Preferred IUPAC name 2,6-Dimethylphenol | |
Other names 2-Hydroxy-m-xylene | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.008.547 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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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). |
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.
Production
[edit]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
[edit]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
[edit]Its LD50 (oral, rats) ranges from 296-1750 mg/kg.[2]
References
[edit]- ^ 2,6-Xylenol at Sigma-Aldrich
- ^ a b c Fiege, Helmut (2000). "Cresols and Xylenols". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_025. ISBN 3527306730.
- ^ 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.
- ^ 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