Methanediol

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Methanediol
Skeletal formula of methanediol with some explicit hydrogens added Methanediol-2D.png
Skeletal formula of methanediol with some explicit hydrogens added
Spacefill model of methanediol Methanediol-3D-vdW.png
Spacefill model of methanediol
Methanediol-3D-balls.png
Names
Preferred IUPAC name
Methanediol [1]
Other names
  • Formaldehyde hydrate
  • Formaldehyde monohydrate
  • Methylene glycol
Identifiers
3D model (JSmol)
AbbreviationsMADOL
1730798
ChEBI
ChemSpider
ECHA InfoCard 100.006.673 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-339-5
PubChem CID
UNII
  • InChI=1S/CH4O2/c2-1-3/h2-3H,1H2 Yes check.svgY
    Key: CKFGINPQOCXMAZ-UHFFFAOYSA-N Yes check.svgY
  • OCO
Properties
CH4O2
Molar mass 48.041 g·mol−1
AppearanceColourless liquid
Density 1.199 g/cm3[ citation needed ]
Boiling point 194 °C (381 °F; 467 K) at 101 kPa [ citation needed ]
Vapor pressure 16.1 Pa [ citation needed ]
Acidity (pKa)13.29 [2]
1.401 [ citation needed ]
Hazards
Flash point 99.753 °C (211.555 °F; 372.903 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Methanediol, also known as formaldehyde monohydrate or methylene glycol, is an organic compound with chemical formula CH2(OH)2. 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 ((CH2O)n), formaldehyde (H2C=O), and 1,3,5-trioxane ((CH2O)3). [3]

Contents

Methanediol is a product of the hydration of formaldehyde. The equilibrium constant for hydration is estimated to be 103, [4] CH2(OH)2 predominates in dilute (<0.1%) solution. In more concentrated solutions, it oligomerizes to HO(CH2O)nH. [3]

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. [5]

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. [5]

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. [6] [7] 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. [8]

See also

Related Research Articles

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In organic chemistry, a ketone is a functional group with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology.

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Formaldehyde ( for-MAL-di-hide, fər-) (systematic name methanal) is an organic compound with the formula CH2O and structure H−CHO. The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section Forms below). 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). It is produced commercially as a precursor to many other materials and chemical compounds. In 2006, the global production rate 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. Small amounts also occur naturally.

<span class="mw-page-title-main">Acetophenone</span> Chemical compound

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<span class="mw-page-title-main">Ethylene oxide</span> Cyclic compound (C2H4O)

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<span class="mw-page-title-main">Dicarbonyl</span> Molecule containing two adjacent C=O groups

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Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin–carbon bonds. The first organotin compound was diethyltin diiodide, discovered by Edward Frankland in 1849. The area grew rapidly in the 1900s, especially after the discovery of the Grignard reagents, which are useful for producing Sn–C bonds. The area remains rich with many applications in industry and continuing activity in the research laboratory.

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<span class="mw-page-title-main">Hexafluoroacetone</span> Chemical compound

Hexafluoroacetone (HFA) is a chemical compound with the formula (CF3)2CO. It is structurally similar to acetone; however, its reactivity is markedly different. It a colourless, hygroscopic, nonflammable, highly reactive gas characterized by a musty odour. The most common form of this substance is hexafluoroacetone sesquihydrate (1.5 H2O), which is a hemihydrate of hexafluoropropane-2,2-diol (F
3
C)
2
C(OH)
2
, a geminal diol.

<span class="mw-page-title-main">Rongalite</span> Chemical compound

Rongalite is a chemical compound with the molecular formula Na+HOCH2SO2. This salt has many additional names, including Rongalit, sodium hydroxymethylsulfinate, sodium formaldehyde sulfoxylate, and Bruggolite. It is listed in the European Cosmetics Directive as sodium oxymethylene sulfoxylate (INCI). It is water-soluble and generally sold as the dihydrate. The compound and its derivatives are widely used in the dye industry. The structure of this salt has been confirmed by X-ray crystallography.

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References

  1. "Methanediol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 20 October 2011.
  2. Bell, R. P.; McTigue, P. T. (1960). "603. Kinetics of the aldol condensation of acetaldehyde". Journal of the Chemical Society (Resumed): 2983. doi:10.1039/JR9600002983.
  3. 1 2 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.
  4. Eric V. Anslyn, Dennis A. Dougherty (2006), Modern physical organic chemistry. University Science Books. ISBN   1-891389-31-9. 1095 pages
  5. 1 2 Zhu, Cheng; Kleimeier, N. Fabian; Turner, Andrew M.; Singh, Santosh K.; Fortenberry, Ryan C.; Kaiser, Ralf I. (4 January 2022). "Synthesis of methanediol [CH 2 (OH) 2 ]: The simplest geminal diol". Proceedings of the National Academy of Sciences. 119 (1): e2111938119. Bibcode:2022PNAS..11911938Z. doi:10.1073/pnas.2111938119. PMC   8740743 . PMID   34969838.
  6. "Hair Smoothing Products That Could Release Formaldehyde". www.osha.gov. Occupational Safety and Health Administration.
  7. SpecialChem. "Industry News".
  8. Golden, R.; Valentini, M. (July 2014). "Formaldehyde and methylene glycol equivalence: Critical assessment of chemical and toxicological aspects". Regulatory Toxicology and Pharmacology . 69 (2): 178–186. doi: 10.1016/j.yrtph.2014.03.007 . PMID   24709515.