Methanediol
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Methanediol, also known as formaldehyde monohydrate or methylene glycol, is an organic compound with chemical formula Template:Chem2. It is the simplest geminal diol. In aqueous solutions it coexists with oligomers (short polymers). The compound is closely related and convertible to the industrially significant derivatives paraformaldehyde (Template:Chem2), formaldehyde (Template:Chem2), and 1,3,5-trioxane (Template:Chem2).[1]
Methanediol is a product of the hydration of formaldehyde. The equilibrium constant for hydration is estimated to be 103,[2]Template:Chem2 predominates in dilute (<0.1%) solution. In more concentrated solutions, it oligomerizes to Template:Chem2.[1]
Occurrence
The dianion, methanediolate, is believed to be an intermediate in the crossed Cannizzaro reaction.
Gaseous methanediols can be generated by electron irradiation and sublimation of a mixture of methanol and oxygen ices.[3]
Methanediol is believed to occur as an intermediate in the decomposition of carbonyl compounds in the atmosphere, and as a product of ozonolysis on these compounds.[3]
Safety
Methanediol, rather than formaldehyde, is listed as one of the main ingredients of "Brazilian blowout", a hair-straightening formula marketed in the United States. The equilibrium with formaldehyde has caused concern since formaldehyde in hair straighteners is a health hazard.[4][5] Research funded by the Professional Keratin Smoothing Council (PKSC), an industry association that represents selected manufacturers of professional-use only keratin smoothing products, has disputed the risk.[6]
See also
- Orthoformic acid (methanetriol)
- Orthocarbonic acid (methanetetrol)
References
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- ↑ a b Template:Ullmann
- ↑ Eric V. Anslyn, Dennis A. Dougherty (2006), Modern physical organic chemistry. University Science Books. Template:ISBN. 1095 pages
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