M-Cresol

<i>m</i>-Cresol

m-Cresol

Chemical compound

Not to be confused with Metacresol purple.

meta-Cresol, also 3-methylphenol, is an organic compound with the formula CH3C6H4(OH). It is a colourless, viscous liquid that is used as an intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of p-cresol and o-cresol.[3]

Quick Facts Names, Identifiers ...

Production

Together with many other compounds, m-cresol is traditionally extracted from coal tar, the volatile materials obtained in the production of coke from (bituminous) coal. This residue contains a few percent by weight of phenol and isomeric cresols. In the cymene–cresol process, toluene is alkylated with propylene to give isomers of cymene, which can be oxidatively dealkylated analogous to the cumene process. Another method, involves carbonylation of a mixture of methallyl chloride and acetylene in the presence of nickel carbonyl.[3]

Applications

m-Cresol is a precursor to numerous compounds. Important applications include:

C7H8O + C3H6 ⇌ C10H14O

Natural occurrences

m-Cresol is a component found in temporal glands secretions during musth in male African elephants (Loxodonta africana).[7]

m-Cresol is a constituent of tobacco smoke.[8]

m-Cresol is a component found in secretions from the ant Colobopsis saundersi during Autothysis.[9] [10]

See also

References

  1. [1]
    NIOSH Pocket Guide to Chemical Hazards. "#0155". National Institute for Occupational Safety and Health (NIOSH).
  2. [2]
    "Cresol (o, m, p isomers)". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. [3]
    Helmut Fiege (2007). "Cresols and Xylenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_025. ISBN 978-3527306732.
  4. [4]
    Alan G. MacDiarmid and Arthur J. Epstein. 1995. "Secondary Doping in Polyaniline" Synthetic Metals 69 (85-92).
  5. [5]
    Stroh, R.; Sydel, R.; Hahn, W. (1963). Foerst, Wilhelm (ed.). Newer Methods of Preparative Organic Chemistry, Volume 2 (1st ed.). New York: Academic Press. p. 344. ISBN 9780323150422.
  6. [6]
    Asim Kumar Mukhopadhyay (2004). Industrial Chemical Cresols and Downstream Derivatives. New York: CRC Press. pp. 99–100. ISBN 9780203997413.
  7. [7]
    Some chemical constituents of the secretion from the temporal gland of the African elephant (Loxodonta africana). Jack Adams, Alexander Garcia and Christopher S. Foote, Journal of Chemical Ecology, 1978, Volume 4, Number 1, 17-25, doi:10.1007/BF00988256
  8. [8]
    Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (2011). "Hazardous Compounds in Tobacco Smoke". International Journal of Environmental Research and Public Health. 8 (12): 613–628. doi:10.3390/ijerph8020613. ISSN 1660-4601. PMC 3084482. PMID 21556207.
  9. [9]
    Jones, T. H.; Clark, D. A.; Edwards, A. A.; Davidson, D. W.; Spande, T. F.; Snelling, Roy R. (2004). "The chemistry of exploding ants, Camponotus spp. (cylindricus complex)". Journal of Chemical Ecology. 30 (8): 1479–1492. doi:10.1023/B:JOEC.0000042063.01424.28. PMID 15537154. S2CID 23756265.
  10. [10]
    Betz, Oliver (2010). "Adhesive Exocrine Glands in Insects: Morphology, Ultrastructure, and Adhesive Secretion". In von Byern, Janek; Grunwald, Ingo (eds.). Biological Adhesive Systems. pp. 111–152. doi:10.1007/978-3-7091-0286-2_8. ISBN 978-3-7091-0141-4.
Share this article:

This article uses material from the Wikipedia article M-Cresol, and is written by contributors. Text is available under a CC BY-SA 4.0 International License; additional terms may apply. Images, videos and audio are available under their respective licenses.