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Production and uses

Cyclohexene is produced by the partial hydrogenation of benzene, a process developed by the Asahi Chemical company.² The main product of the process is cyclohexane because cyclohexene is more easily hydrogenated than benzene.

In the laboratory, it can be prepared by dehydration of cyclohexanol.³

Reactions and uses

Benzene is converted to cyclohexylbenzene by acid-catalyzed alkylation with cyclohexene.⁴ Cyclohexylbenzene is a precursor to both phenol and cyclohexanone.⁵

Hydration of cyclohexene gives cyclohexanol, which can be dehydrogenated to give cyclohexanone, a precursor to caprolactam.⁶

The oxidative cleavage of cyclohexene gives adipic acid. Hydrogen peroxide is used as the oxidant in the presence of a tungsten catalyst.⁷

1,5-Hexadiene is produced by ethenolysis of cyclohexene. Bromination gives 1,2-dibromocyclohexane.⁸

Structure

Cyclohexene is most stable in a half-chair conformation,⁹ unlike the preference for a chair form of cyclohexane. One basis for the cyclohexane conformational preference for a chair is that it allows each bond of the ring to adopt a staggered conformation. For cyclohexene, however, the alkene is planar, equivalent to an eclipsed conformation at that bond.

See also

• Diels-Alder reaction
• Cyclohexa-1,3-diene
• Cyclohexa-1,4-diene

External links

• International Chemical Safety Card 1054
• NIOSH Pocket Guide to Chemical Hazards. "#0167". National Institute for Occupational Safety and Health (NIOSH).
• Material Safety Data Sheet for cyclohexene
• Safety MSDS data
• Reaction of Cyclohexene with Bromine and Potassium Permanganate
• Cyclohexene synthesis
• Data sheet at inchem.org

References

1. Xie, Feng; Chen, Lihang; Cedeño Morales, Eder Moisés; Ullah, Saif; Fu, Yiwen; Thonhauser, Timo; Tan, Kui; Bao, Zongbi; Li, Jing (2024). "Complete separation of benzene-cyclohexene-cyclohexane mixtures via temperature-dependent molecular sieving by a flexible chain-like coordination polymer". Nature Communications. 15 (1): 2240. Bibcode:2024NatCo..15.2240X. doi:10.1038/s41467-024-46556-6. PMC 10933443. PMID 38472202. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10933443 ↩

2. US 9771313, Narisawa, Naoki & Tanaka, Katsutoshi, "Cyclohexanol, method for producing cyclohexanol, and method for producing adipic acid", published 26 Sep 2017 https://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=US9771313 ↩

3. G. H. Coleman, H. F. Johnstone (1925). "Cyclohexene". Organic Syntheses. 5: 33. doi:10.15227/orgsyn.005.0033. /wiki/Doi_(identifier) ↩

4. B. B. Corson, V. N. Ipatieff (1939). "Cyclohexylbenzene". Organic Syntheses. 19: 36. doi:10.15227/orgsyn.019.0036. /wiki/Doi_(identifier) ↩

5. Plotkin, Jeffrey S. (2016-03-21). "What's New in Phenol Production?". American Chemical Society. Archived from the original on 2019-10-27. Retrieved 2018-01-02. https://web.archive.org/web/20191027122212/https://www.acs.org/content/acs/en/pressroom/cutting-edge-chemistry/what-s-new-in-phenol-production-.html ↩

6. Musser, Michael T. (2005). "Cyclohexanol and Cyclohexanone". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_217. ISBN 978-3-527-30673-2. 978-3-527-30673-2 ↩

7. Reed, Scott M.; Hutchison, James E. (2000). "Green Chemistry in the Organic Teaching Laboratory: An Environmentally Benign Synthesis of Adipic Acid". J. Chem. Educ. 77 (12): 1627–1629. Bibcode:2000JChEd..77.1627R. doi:10.1021/ed077p1627. /wiki/Bibcode_(identifier) ↩

8. H. R. Snyder, L. A. Brooks (1932). "1,2-Dibromocyclohexane". Organic Syntheses. 12: 26. doi:10.15227/orgsyn.012.0026. /wiki/Doi_(identifier) ↩

9. Jensen, Frederick R.; Bushweller, C. Hackett (1969). "Conformational preferences and interconversion barriers in cyclohexene and derivatives". J. Am. Chem. Soc. 91 (21): 5774–5782. doi:10.1021/ja01049a013. /wiki/Doi_(identifier) ↩