2,6-Xylenol

Last updated
2,6-Xylenol [1]
2,6-Xylenol.svg
2,6-Xylenol-3D-spacefill.png
Names
Preferred IUPAC name
2,6-Dimethylphenol
Other names
2-Hydroxy-m-xylene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.547 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C8H10O/c1-6-4-3-5-7(2)8(6)9/h3-5,9H,1-2H3 X mark.svgN
    Key: NXXYKOUNUYWIHA-UHFFFAOYSA-N X mark.svgN
  • 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
Appearancewhite 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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

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]

The antiseptic chloroxylenol is produced by chlorination of this xylenol. [4]

2,6-Xylenol is susceptible to oxidative coupling leading to polymers and dimers. [5]

Toxicity

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

References

  1. ↑ 2,6-Xylenol at Sigma-Aldrich
  2. 1 2 3 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. ↑ Mostafa, Mohamed A. B.; Bowley, Rosalind M.; Racys, Daugirdas T.; Henry, Martyn C.; Sutherland, Andrew (2017). "Iron(III)-Catalyzed Chlorination of Activated Arenes". The Journal of Organic Chemistry. 82 (14): 7529–7537. doi:10.1021/acs.joc.7b01225. PMID   28661157.
  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 Abstract
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