Cymene

For the ancient Greek city, see Cymene (Thessaly).

Cymene describes organic compounds with the formula CH3C6H4CH(CH3)2. Three isomers exist: 1,2- 1,3-, and 1,4-. All are colorless liquids, immiscible in water, with similar boiling points. They are classified are aromatic hydrocarbons. The bearing two substituents: an isopropyl (CH(CH3)2) group and a methyl group.[1]

Cymenes
Name o-Cymene m-Cymene p-Cymene
Structural formula
CAS number 527-84-4 535-77-3 99-87-6
melting point  -71.54  -63.75  -67.94
boiling point (°C) 178.15 175.05 177.10

Production and reactions

m- and p-Cymene are prepared by alkylation of toluene with propylene:

CH3C6H5 + 2 CH3CH=CH2 → CH3C6H4CH(CH3)2

These alkylations are catalyzed by various Lewis acids, such as aluminium trichloride.

m- and p-Cymene are mainly of interest as precursors to the respective cresols, which exploits the Hock rearrangements.[1]

References

  1. ^ a b Schmidt, Roland; Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2014). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–74. doi:10.1002/14356007.a13_227.pub3. ISBN 9783527306732.


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