Chemistry:Cyclohexyl hydroperoxide
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| Names | |
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| IUPAC name
hydroperoxycyclohexane
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Other names
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| UNII | |
| UN number | 9183 |
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| Properties | |
| C6H12O2 | |
| Molar mass | 116.160 g·mol−1 |
| Appearance | Colorless |
| Density | 1.02 g/cm3 |
| Melting point | −20 °C (−4 °F; 253 K) |
| Boiling point | 200 °C (392 °F; 473 K) |
| Hazards | |
| GHS pictograms |  
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| GHS Signal word | Danger |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Cyclohexyl hydroperoxide (CHHP) is an organic hydroperoxide that is typically used to assist in industrially producing cyclohexanol and cyclohexanone. These compounds are then usually turned into the polymer nylon 6 (polycaprolactam).[1] It has no color and is transparent when pure. It was first synthesized and prepared in 1930 by two German chemists, and has since been used for other modern industrial production.
Properties
In its pure form, the compound appears as a colorless and transparent liquid, with a distinct garlic smell.[2] It is corrosive and irritation hazard.[3] Although organic peroxides are generally unstable, cyclohexyl hydroperoxide only decomposes slowly.[2]
Preparation and synthesis
The first known method of synthesizing the compound was published in 1930 by chemists Stoll and Scherrer,[4] in which the authors detailed a method to produce 1-hydroxy-cyclohexyl-hydroperoxide-1, a related compound. This involved using peroxymonosulfuric acid to convert cyclic ketone into its corresponding lactone.[5] They proceeded to use ozone and hydrogen peroxide and allowed it to oxidize for several days, then examined it again. They had discovered they had now produced the new oxygen-rich cyclanone peroxides they desired.[5]
References
- ↑ Berezin 1966, p. 41
- ↑ 2.0 2.1 Farkas, Adalbert; Passaglia, Elio (August 1, 1950). "The Decomposition of Cyclohexyl Hydroperoxide and the Peroxide-catalyzed Polymerization of Styrene". Journal of the American Chemical Society 72 (8): 3333–3337. doi:10.1021/ja01164a002. ISSN 0002-7863. OCLC 4665340971. Bibcode: 1950JAChS..72.3333F.
- ↑ Template:Cite PubChem
- ↑ , Halbig"Process for the production of crystalline cyclohexyl peroxides" US patent US2750421A, published 1956-06-12
- ↑ 5.0 5.1 Stoll & Scherrer 1930, p. 142
Bibliography
- Berezin, Ilya (1966). The Oxidation of Cyclohexane. Burlington: Elsevier Science. ISBN 9781483185637. OCLC 893741849.
- Stoll, M.; Scherrer, W. (January 30, 1930). "Über die Oxydation von Cyclo-polymethylen-ketonen mit Wasserstoffperoxyd und Ozon" (in de). Helvetica Chimica Acta 13 (2): 142–153. doi:10.1002/hlca.19300130205. ISSN 0018-019X. OCLC 5154572621.
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