Cymene

Cymene describes organic compounds with the formula CH
3C
6H
4CH(CH
3)
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(CH
3)
2) group and a methyl group.^[1]

Cymenes
Name	o-Cymene	m-Cymene	p-Cymene
Structural formula		110px
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:

CH
3C
6H
5 + 2 CH
3CH=CH
2 → CH
3C
6H
4CH(CH
3)
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

↑ ^1.0 ^1.1 Schmidt, Roland; Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd et al. (2014). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–74. doi:10.1002/14356007.a13_227.pub3. ISBN 9783527306732.

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[HC-1] 1.0 ^1.1 Schmidt, Roland; Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd et al. (2014). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–74. doi:10.1002/14356007.a13_227.pub3. ISBN 9783527306732.

[1]

Cymene

Topic: Chemistry

Production and reactions

References