1,3,5-Trioxane

<h2 id="production">Production</h2>
<p>Trioxane can be obtained by the acid-<a href="/facts/Catalyst/LPBS7TQC">catalyzed</a> cyclic trimerization of formaldehyde in concentrated aqueous solution.<a class="footnote-ref" id="fnref:1" href="#fn:1"><sup>1</sup></a> 
</p>

<h2 id="uses">Uses</h2>
<p>Trioxane can be used interchangeably with formaldehyde and with paraformaldehyde,<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a><a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> 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 <a href="/facts/Polyoxymethylene_plastic/TFrYKSx7">polyoxymethylene plastics</a>, of which about one million tons per year are produced.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a>  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 <a href="/facts/Hexamethylenetetramine/jnFrmG81">hexamine</a> and compressed into solid bars to make <a href="/facts/Hexamine_fuel_tablet/G4mBj8xR">hexamine fuel tablets</a>, used by the <a href="/facts/Military/kgNmLUnN">military</a> and <a href="/facts/Camping/JmwUIl3A">outdoorsmen</a> as a cooking fuel.
</p><p>In the laboratory, trioxane is used as an anhydrous source of formaldehyde.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a>
</p>
<h2 id="see-also">See also</h2>
<ul><li><a href="/facts/Formaldehyde/Ck8RLfqk">Formaldehyde</a></li>
<li><a href="/facts/Paraformaldehyde/9lcmgIWD">Paraformaldehyde</a></li>
<li><a href="/facts/Dioxane/ILtQeBxC">Dioxane</a></li>
<li><a href="/facts/1%2c3%2c5-Trioxanetrione/fW7c7yNs">1,3,5-Trioxanetrione</a></li></ul>

<h2 id="references">References</h2>

<ol>
<li id="fn:1"><p>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. <a href="3527306730" target="_blank">3527306730</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li>
<li id="fn:2"><p>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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li>
<li id="fn:3"><p>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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li>
<li id="fn:4"><p>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. <a href="3527306730" target="_blank">3527306730</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li>
<li id="fn:5"><p>W. O. Teeters; M. A. Gradsten (1950). "Hexahydro-1,3,5-Tripropionyl-s-Triazine". Organic Syntheses. 30: 51. doi:10.15227/orgsyn.030.0051. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li>
</ol>

1,3,5-Trioxane open-in-new

1,3,5-Trioxane