1,3,5-Trioxane
| |||
| Names | |||
|---|---|---|---|
| IUPAC name
1,3,5-Trioxane
| |||
| Other names
s-Trioxane; 1,3,5-Trioxacyclohexane; Trioxymethylene; Metaformaldehyde; Trioxin
| |||
| Identifiers | |||
3D model (JSmol)
|
|||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.003.466 | ||
| RTECS number |
| ||
| UNII | |||
CompTox Dashboard (EPA)
|
|||
| |||
| |||
| Properties | |||
| C3H6O3 | |||
| Molar mass | 90.078 g·mol−1 | ||
| Appearance | White crystalline solid | ||
| Density | 1.17 g/cm3 (65 °C)[1] | ||
| Melting point | 62 °C (144 °F; 335 K)[1] | ||
| Boiling point | 115 °C (239 °F; 388 K)[1] | ||
| 221 g/L[1] | |||
| Hazards | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 45 °C (113 °F)[1] | ||
| Related compounds | |||
Related compounds
|
Formaldehyde | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |||
1,3,5-Trioxane, sometimes also called trioxane or trioxin, is a chemical compound with molecular formula C3H6O3. It is a white solid with a chloroform-like odor. It is a stable cyclic trimer of formaldehyde, and one of the three trioxane isomers; its molecular backbone consists of a six-membered ring with three carbon atoms alternating with three oxygen atoms. Thus, cyclotrimerization of formaldehyde affords 1,3,5-trioxane:
Production
Of pedagical value but not necessarily mechanistically significant, trioxane can be viewed as the product of the trimerization of formaldehyde or the condensation of three equivalents of dihydroxymethane.
In practice, trioxane is produced by acid-catalyzed reaction of concentrated aqueous solution of formaldehyde.[2]
Uses
Trioxane is often used interchangeably with formaldehyde and with paraformaldehyde.[3][4] It is a precursor for the production of polyoxymethylene plastics, of which about one million tons per year are produced.[2] Other applications exploit its tendency to release formaldehyde. As such it is used as a binder in textiles, wood products, etc. Trioxane is combined with hexamine and compressed into solid bars to make hexamine fuel tablets, used by the military and outdoorsmen as a cooking fuel.
In the laboratory, trioxane is used as an anhydrous source of formaldehyde.[5]
See also
References
- ^ a b c d e Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ a b Reuss, Günther; Disteldorf, Walter; Gamer, Armin Otto; Hilt, Albrecht (2000). "Formaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_619. ISBN 3527306730.
- ^ K. Chen; C. S. Brook; A. B. Smith, III (1998). "6,7-Dihydrocyclopenta-1,3-Dioxin-5(4H)-One". Organic Syntheses. 75: 189. doi:10.15227/orgsyn.075.0189.
- ^ D. S. Connor; G. W. Klein; G. N. Taylor; R. K. Boeckman, Jr; J. B. Medwid (1972). "Benzyl Chloromethyl Ether". Organic Syntheses. 52: 16. doi:10.15227/orgsyn.052.0016.
- ^ W. O. Teeters; M. A. Gradsten (1950). "Hexahydro-1,3,5-Tripropionyl-s-Triazine". Organic Syntheses. 30: 51. doi:10.15227/orgsyn.030.0051.