1,3,5-Trioxane

Last updated
1,3,5-Trioxane
S-Trioxane.svg
1,3,5-Trioxane-3D-balls.png
Names
Preferred IUPAC name
1,3,5-Trioxane
Other names
s-Trioxane; 1,3,5-Trioxacyclohexane; Trioxymethylene; Metaformaldehyde
Identifiers
3D model (JSmol)
102769
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.466 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-812-5
2230
PubChem CID
RTECS number
  • YK0350000
UNII
UN number 1325
  • InChI=1S/C3H6O3/c1-4-2-6-3-5-1/h1-3H2 Yes check.svgY
    Key: BGJSXRVXTHVRSN-UHFFFAOYSA-N Yes check.svgY
  • O1COCOC1
Properties
C3H6O3
Molar mass 90.078 g·mol−1
AppearanceWhite 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 labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Warning
H228, H335, H361d
P201, P202, P210, P240, P241, P261, P271, P280, P281, P304+P340, P308+P313, P312, P370+P378, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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 fuelInstability 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 [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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1,3,5-Trioxane, sometimes also called trioxane, 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.

Contents

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 can be used interchangeably with formaldehyde and with paraformaldehyde, [3] [4] however the cyclic structure is more stable and it can require high temperatures in order to react. 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 2 3 4 5 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 1 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. ISBN   3527306730.
  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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