Chemistry:Cyclooctanol
Cyclooctanol is an organic compound with the formula (CH
2)
7CHOH or C
8H
15OH. It is a colorless oily liquid with a pleasant odor. The molecule consists of 8-membered cyclooctane ring in which one of its hydrogen atoms is replaced by a hydroxyl group.
Synthesis
Cyclooctanol can be obtained by hydrolysis of cyclooctyl formate.[1]
- HCOOC
8H
15 + H
2O → C
8H
15OH + HCOOH
Cyclooctanol can also be synthesized by oxidation of cyclooctane by hydrogen peroxide with polyoxometalates as catalysts in acetonitrile. The reaction byproducts are cyclooctanone and cyclooctyl hydroperoxide.[2][3]
Properties
It has been investigated how cyclooctanol behaves under high pressure. At around 0.4 GPa cyclooctanol becomes a solid, which is in the form of plastic crystals. At around 1.1 GPa, it becomes a normal ordered crystal phase. These phase transitions are reversible.[4]
Under high pressure, new solid phase of cyclooctanol (phase III) is discovered and characterized as a normal crystal phase, and all other solid phases (I, II, IV) are characterized as plastic crystal phases.[5]
Reactions
Cyclooctanol reacts with diethylaminosulfur trifluoride to give fluorocyclooctane and cyclooctene.[6]
References
- ↑ Sommer, Tomáš; Zapletal, Martin; Trejbal, Jiří (2018). "Production of cyclic alcohols". Chemical Papers 72 (10): 2397–2412. doi:10.1007/s11696-018-0508-5. Bibcode: 2018ChPap..72.2397S. https://link.springer.com/article/10.1007/s11696-018-0508-5.
- ↑ Cite error: Invalid
<ref>tag; no text was provided for refs namedchemsrc - ↑ Wimonrat, Trakarnpruk; Apiwat, Wannatem; Jutatip, Kongpeth (January 1, 2012). "Polyoxometalates catalysts in the oxidation of cyclooctane by hydrogen peroxide". Journal of the Serbian Chemical Society 77 (11): 1599–1607. doi:10.2298/jsc111124040t. http://www.doiserbia.nb.rs/img/doi/0352-5139/2012/0352-51391200040T.pdf.
- ↑ Ren, Yufen; Cheng, Xuerui; Yang, Kun; Zhu, Xiang; Li, Haining; Wang, Yongqiang (December 15, 2015). "Raman study of plastic crystal phase of cyclooctanol under high pressure with different compression rate". Journal of Molecular Structure 1102: 6–10. doi:10.1016/j.molstruc.2015.08.006. Bibcode: 2015JMoSt1102....6R. https://www.sciencedirect.com/science/article/pii/S0022286015301940.
- ↑ Andersson, Ove; Ross, Russell G. (1990). "Thermal conductivity, heat capacity and phase diagram of cyclooctanol in liquid, solid and glassy crystal states under high pressure". Molecular Physics 71 (3): 523–539. doi:10.1080/00268979000101951. Bibcode: 1990MolPh..71..523A. https://www.tandfonline.com/doi/abs/10.1080/00268979000101951.
- ↑ Middleton, William J. (1975). "New fluorinating reagents. Dialkylaminosulfur fluorides". The Journal of Organic Chemistry 40 (5): 574–578. doi:10.1021/jo00893a007. Bibcode: 1975JOrgC..40..574M. https://pubs.acs.org/doi/abs/10.1021/jo00893a007.
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