Trioxane

Trioxane refers to any of three isomeric organic compounds composed of a six-membered ring with three carbon atoms and three oxygen atoms, having the molecular formula C₃H₆O₃.

The three isomers are:

References

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:

The mechanism can be explained in an acidic catalyzed reaction:

Uses

In chemistry, 1,3,5-trioxane is used as a stable, easily handled source of anhydrous formaldehyde. In acidic solutions, it decomposes to generate three molecules of formaldehyde. It may also be used in polymerization to form acetal resins, such as polyoxymethylene plastic. It is a feedstock for certain types of plastic, is an ingredient in some solid fuel tablet formulas, and is used in chemical laboratories as a stable source of formaldehyde.

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.

1,2,4-Trioxane

1,2,4-Trioxane is one of the isomers of trioxane. It has the molecular formula C₃H₆O₃ and consists of a six membered ring with three carbon atoms and three oxygen atoms. The two adjacent oxygen atoms form a peroxide functional group and the other forms an ether functional group. It is like a cyclic acetal but with one of the oxygen atoms in the acetal group being replaced by a peroxide group.

1,2,4-Trioxane itself has not been isolated or characterized, but rather only studied computationally. However, it constitutes an important structural element of some more complex organic compounds. The natural compound artemisinin, isolated from the sweet wormwood plant (Artemisia annua), and some semi-synthetic derivatives are important antimalarial drugs containing the 1,2,4-trioxane ring. Completely synthetic analogs containing the 1,2,4-trioxane ring are important potential improvements over the naturally derived artemisinins. The peroxide group in the 1,2,4-trioxane core of artemisinin is cleaved in the presence of the malaria parasite leading to reactive oxygen radicals that are damaging to the parasite.