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1,3,5-Trioxane
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changed 477204812 1,3,5-Trioxane S-Trioxane.svg skin-invert 1,3,5-Trioxane-3D-balls.png Trioxane molecule bg-transparent 140 1,3,5-Trioxane s-Trioxane; 1,3,5-Trioxacyclohexane; Trioxymethylene; Metaformaldehyde correct CAS 110-88-3 102769 correct chemspider correct EBI 38043 1495792 7790 203-812-5 2230 8081 YK0350000 1325 correct FDA 46BNU65YNY O1COCOC1 correct chemspider 1S/C3H6O3/c1-4-2-6-3-5-1/h1-3H2 correct chemspider BGJSXRVXTHVRSN-UHFFFAOYSA-N 3 6 3 White crystalline solid 1.17 g/cm3 (65 °C)29710 221 g/L 62 115 45 2 2 0 02 07 08 Warning 228 335 361d 201 202 210 240 241 261 271 280 281 304+340 308+313 312 370+378 403+233 405 501 Formaldehyde 1,2,4-Trioxane 1,3,5-Trithiane Polyoxymethylene
1,3,5-Trioxane, sometimes also called trioxane, is a chemical compound with molecular formula C3H6O3 1. 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.
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Uses
Trioxane can be used interchangeably with formaldehyde and with paraformaldehyde,10.15227/orgsyn.075.0189 free 6,7-Dihydrocyclopenta-1,3-Dioxin-5(4H)-One Organic Syntheses 1998 75 189 K. Chen C. S. Brook A. B. Smith, III10.15227/orgsyn.052.0016 free Benzyl Chloromethyl Ether Organic Syntheses 1972 52 16 D. S. Connor G. W. Klein G. N. Taylor R. K. Boeckman, Jr J. B. Medwid 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.10.1002/14356007.a11_619 Formaldehyde 2000 Reuss Günther Disteldorf Walter Gamer Armin Otto Hilt Albrecht 3527306730 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.10.15227/orgsyn.030.0051 free Hexahydro-1,3,5-Tripropionyl-s-Triazine Organic Syntheses 1950 30 51 W. O. Teeters M. A. Gradsten
See also
Formaldehyde
Paraformaldehyde
Dioxane
1,3,5-Trioxanetrione
References
Category:Acetals
Category:Trioxanes
Category:Trimers (chemistry)