Chemistry:1,3,5-Trioxane

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1,3,5-Trioxane
S-Trioxane.svg
Trioxane molecule
Names
Preferred IUPAC name
1,3,5-Trioxane
Other names
s-Trioxane; 1,3,5-Trioxacyclohexane; Trioxymethylene; Metaformaldehyde; Trioxin
Identifiers
3D model (JSmol)
102769
ChEBI
ChEMBL
ChemSpider
EC Number
  • 203-812-5
2230
RTECS number
  • YK0350000
UNII
UN number 1325
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
GHS pictograms GHS02: FlammableGHS07: HarmfulGHS08: Health hazard
GHS Signal word Warning
H228, H335, H361d
P201, P202, P210, P240, P241, P261, P271, P280, P281, P304+340, P308+313, P312, P370+378, P403+233, P405, P501
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 codeNFPA 704 four-colored diamond
2
2
0
Flash point 45[1] °C (113 °F; 318 K)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tracking categories (test):

1,3,5-Trioxane, sometimes also called trioxane or trioxin, is a chemical compound with molecular formula C3H6O3. It is a white, highly water-soluble 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.

Production

Trioxane can be obtained by the acid-catalyzed cyclic trimerization of formaldehyde in concentrated aqueous solution.[2]

Trioxane Synthesis V.1.svg

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. ↑ 1.0 1.1 1.2 1.3 1.4 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ↑ 2.0 2.1 Reuss, Günther; Disteldorf, Walter; Gamer, Armin Otto; Hilt, Albrecht (2000). "Ullmann's Encyclopedia of Industrial Chemistry". 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. 



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