1,3,5-Trioxane

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:

"Trioxin" redirects here. For the fictional chemical, see Return of the Living Dead (film series).
1,3,5-Trioxane
Trioxane molecule
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
  • YK0350000
UNII
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
R-phrases (outdated) R22
S-phrases (outdated) S24/25
NFPA 704 (fire diamond)
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 45 °C (113 °F)[1]
Related compounds
Related compounds
 Formaldehyde

1,2,4-Trioxane Polyoxymethylene

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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
  1. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 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.
  3. 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.
  4. 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.
  5. W. O. Teeters; M. A. Gradsten (1950). "Hexahydro-1,3,5-Tripropionyl-s-Triazine". Organic Syntheses. 30: 51. doi:10.15227/orgsyn.030.0051.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.