dihydroxymethane

Dihydroxymethane, also known as methanediol, is the simplest geminal diol with the formula CH2(OH)2. It is the hydrated form of formaldehyde (CH2O) and the form in which formaldehyde predominantly exists in aqueous solution. The equilibrium CH2O + H2O ⇌ CH2(OH)2 describes the interconversion; in water, the hydrate is in equilibrium with free formaldehyde and is generally present in appreciable amounts, though the exact distribution depends on concentration, temperature, and pH. In the absence of water, dihydroxymethane is not isolable under normal conditions and quickly reverts to formaldehyde and water.

The molecule has a tetrahedral carbon bearing two hydroxyl groups, making it a geminal diol. The structure is stabilized by hydrogen bonding in solution, but the diol is relatively reactive and readily dehydrates to formaldehyde when water is removed or the system is driven toward dehydration.

Formation and occurrence: In practice, dihydroxymethane is encountered mainly in aqueous formaldehyde solutions, such as formalin, where it exists in equilibrium with CH2O. It is a transient intermediate rather than a stand-alone chemical used for manufacturing.

Reactivity and applications: As the hydrated form of formaldehyde, methanediol participates in reactions characteristic of aldehydes. It can be involved in polymerization processes that lead to polyoxymethylene derivatives. It is not produced or sold as a bulk chemical; its relevance is largely to discussions of formaldehyde hydration and solution chemistry.

Safety: Formaldehyde and its hydrate are irritants and potential carcinogens. Dihydroxymethane can release formaldehyde in solution, so handling requires appropriate ventilation and protective equipment.