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Formaldehyde

Formaldehyde (/fɔːrˈmældɪhd/ for-MAL-di-hide, US also /fər-/ fər-) (systematic name methanal) is an organic compound with the chemical formula CH2O and structure H2C=O. The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as aqueous solutions (formalin), which consists mainly of the hydrate CH2(OH)2. It is the simplest of the aldehydes (R−CHO). As a precursor to many other materials and chemical compounds, in 2006 the global production of formaldehyde was estimated at 12 million tons per year. It is mainly used in the production of industrial resins, e.g., for particle board and coatings.

Formaldehyde also occurs naturally. It is derived from the degradation of serine, dimethylglycine, and lipids. Demethylases act by converting N-methyl groups to formaldehyde.

Formaldehyde is classified as a group 1 carcinogen and can cause respiratory and skin irritation upon exposure.

Formaldehyde is more complicated than many simple carbon compounds in that it adopts several diverse forms. These compounds can often be used interchangeably and can be interconverted.[citation needed]

A small amount of stabilizer, such as methanol, is usually added to suppress oxidation and polymerization. A typical commercial-grade formalin may contain 10–12% methanol in addition to various metallic impurities.

"Formaldehyde" was first used as a generic trademark in 1893 following a previous trade name, "formalin".

Molecular formaldehyde contains a central carbon atom with a double bond to the oxygen atom and a single bond to each hydrogen atom. This structure is summarised by the condensed formula H2C=O. The molecule is planar, Y-shaped and its molecular symmetry belongs to the C2v point group. The precise molecular geometry of gaseous formaldehyde has been determined by gas electron diffraction and microwave spectroscopy. The bond lengths are 1.21 Å for the carbon–oxygen bond and around 1.11 Å for the carbon–hydrogen bond, while the H–C–H bond angle is 117°, close to the 120° angle found in an ideal trigonal planar molecule. Some excited electronic states of formaldehyde are pyramidal rather than planar as in the ground state.

Processes in the upper atmosphere contribute more than 80% of the total formaldehyde in the environment. Formaldehyde is an intermediate in the oxidation (or combustion) of methane, as well as of other carbon compounds, e.g. in forest fires, automobile exhaust, and tobacco smoke. When produced in the atmosphere by the action of sunlight and oxygen on atmospheric methane and other hydrocarbons, it becomes part of smog. Formaldehyde has also been detected in outer space.

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