Methanediol - Wikipedia

"Methylene glycol" redirects here; not to be confused with Ethylene glycol. Organic compound (CH2(OH)2); simplest geminal diol Methanediol

Names
Preferred IUPAC name Methanediol[1]
Other names Formaldehyde hydrate Formaldehyde monohydrate Methylene glycol
Identifiers
CAS Number	463-57-0 Y
3D model (JSmol)	Interactive image
Abbreviations	MADOL
Beilstein Reference	1730798
ChEBI	CHEBI:48397 Y
ChemSpider	71348 Y
ECHA InfoCard	100.006.673
EC Number	207-339-5
PubChem CID	79015
UNII	6Z20YM9257 Y
CompTox Dashboard (EPA)	DTXSID50196801
InChI InChI=1S/CH4O2/c2-1-3/h2-3H,1H2 YKey: CKFGINPQOCXMAZ-UHFFFAOYSA-N Y
SMILES OCO
Properties
Chemical formula	CH4O2
Molar mass	48.041 g·mol−1
Appearance	Colourless 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]
Refractive index (nD)	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). Y verify (what is YN ?) Infobox references

Chemical compound

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]

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

[edit]

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

[edit]

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

[edit]

• Orthoformic acid (methanetriol)
• Orthocarbonic acid (methanetetrol)

References

[edit]

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. ^ a b 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. ISBN 3527306730.
4. ^ Eric V. Anslyn, Dennis A. Dougherty (2006), Modern physical organic chemistry. University Science Books. ISBN 1-891389-31-9. 1095 pages
5. ^ a b 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.

v t e Alcohols
By consumption	Alcohols found inalcoholic drinks 1-Propanol 2-Methyl-1-butanol Ethanol Isoamyl alcohol Isobutanol Phenethyl alcohol tert-Amyl alcohol tert-Butyl alcohol Tryptophol Medical alcohol Ethchlorvynol Methylpentynol Methanol poisoning Ethanol Toxic alcohols Isopropyl alcohol Methanol
Primaryalcohols (1°)	Methanol 4-Methylcyclohexanemethanol Aminomethanol Cyclohexylmethanol Methoxymethanol Methylazoxymethanol Trifluoromethanol Ethanol 1-Aminoethanol 2,2,2-Trichloroethanol 2,2,2-Trifluoroethanol 2-(2-Ethoxyethoxy)ethanol 2-(2-Methoxyethoxy)ethanol 2-(2-Methoxyethoxy)ethanol 2-Butoxyethanol 2-Chloroethanol 2-Ethoxyethanol 2-Fluoroethanol 2-Mercaptoethanol 2-Methoxyethanol Aminoethylethanolamine Diethylethanolamine Dimethylethanolamine Ethanol Ethanolamine N,N-Diisopropylaminoethanol N-Methylethanolamine Phenoxyethanol Tribromoethanol Butanol 2-Methyl-1-butanol Isobutanol n-Butanol Straight-chainsaturatedC1 — C9 Methanol Ethanol 1-Propanol 1-Butanol 1-Pentanol 1-Hexanol 1-Heptanol 1-Octanol (capryl) 1-Nonanol (pelargonic) Straight-chainsaturatedC10 — C19 1-Decanol (capric) 1-Undecanol (hendecyl) 1-Dodecanol (lauryl) 1-Tridecanol 1-Tetradecanol (myristyl) 1-Pentadecanol 1-Hexadecanol (cetyl / palmityl) 1-Heptadecanol 1-Octadecanol (stearyl) 1-Nonadecanol Straight-chainsaturatedC20 — C29 1-Icosanol (arachidyl) 1-Heneicosanol 1-Docosanol (behenyl) 1-Tricosanol 1-Tetracosanol (lignoceryl) 1-Pentacosanol 1-Hexacosanol (ceryl) 1-Heptacosanol 1-Octacosanol (cluytyl / montanyl) 1-Nonacosanol Straight-chainsaturatedC30 — C39 1-Triacontanol (melissyl / myricyl) 1-Hentriacontanol 1-Dotriacontanol (lacceryl) 1-Tritriacontanol 1-Tetratriacontanol (geddyl) 1-Pentatriacontanol 1-Hexatriacontanol 1-Heptatriacontanol 1-Octatriacontanol 1-Nonatriacontanol Straight-chainsaturatedC40 — C49 1-Tetracontanol 1-Hentetracontanol 1-Dotetracontanol 1-Tritetracontanol 1-Tetratetracontanol 1-Pentatetracontanol 1-Hexatetracontanol 1-Heptatetracontanol 1-Octatetracontanol 1-Nonatetracontanol 2-Ethylhexanol Allyl alcohol Anisyl alcohol Benzyl alcohol Cinnamyl alcohol Crotyl alcohol Furfuryl alcohol Isoamyl alcohol Neopentyl alcohol Nicotinyl alcohol Perillyl alcohol Phenethyl alcohol Prenol Propargyl alcohol Salicyl alcohol Tryptophol Vanillyl alcohol Veratrole alcohol
Secondary alcohols (2°)	1-Phenylethanol 2-Butanol 2-Deoxyerythritol 2-Heptanol 3-Heptanol 2-Hexanol 3-Hexanol 3-Methyl-2-butanol 2-Nonanol 2-Octanol 2-Pentanol 3-Pentanol Cyclohexanol Cyclopentanol Cyclopropanol Diphenylmethanol Isopropanol Pinacolyl alcohol Pirkle's alcohol Propylene glycol methyl ether
Tertiary alcohols (3°)	2-Methyl-2-pentanol 2-Methylheptan-2-ol 2-Methylhexan-2-ol 3-Methyl-3-pentanol 3-Methyloctan-3-ol Diacetone alcohol Ethchlorvynol Methylpentynol Nonafluoro-tert-butyl alcohol tert-Amyl alcohol tert-Butyl alcohol Triphenylethanol Triphenylmethanol
Hydric alcohols	Monohydric alcohols Methanol (C1) Ethanol (C2) Isopropanol (C3) 1-Butanol (C4) 1-Pentanol (C5) Cetyl alcohol (C16) Dihydric alcohols Ethylene glycol Propylene glycol Trihydric alcohols Glycerol Polyhydric alcohols (sugar alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)
Amyl alcohols	2,2-Dimethylpropan-1-ol 2-Methylbutan-1-ol 2-Methylbutan-2-ol 3-Methylbutan-1-ol 3-Methylbutan-2-ol Pentan-1-ol Pentan-2-ol Pentan-3-ol
Aromatic alcohols	Benzyl alcohol 2,4-Dichlorobenzyl alcohol 3-Nitrobenzyl alcohol
Saturatedfatty alcohols	Cetostearyl alcohol Decanol Lauryl alcohol Myristyl alcohol Nonanol Octanol Tridecanol Undecanol
Branched andunsaturatedfatty alcohols	3-Methyl-3-pentanol Erucyl alcohol Linolenyl alcohol Linoleyl alcohol Oleyl alcohol Palmitoleyl alcohol tert-Amyl alcohol tert-Butyl alcohol
Sugar alcohols	C1 — C7 Methylene glycol (C1) Ethylene glycol (C2) Glycerol (C3) Erythritol (C4) Threitol (C4) Arabitol (C5) Ribitol (C5) Xylitol (C5) Mannitol (C6) Sorbitol (C6) Galactitol (C6) Iditol (C6) Volemitol (C7) Deoxy sugar alcohols Fucitol Cyclic sugar alcohols Inositol Glycylglycitols Maltitol Lactitol Isomalt Maltotriitol Maltotetraitol Polyglycitol
Terpene alcohols	Monoterpene alcohols Borneol Citronellol Geraniol Linalool Menthol Nerol Rhodinol Terpineol Sesquiterpene alcohols Bisabolol Farnesol Nerolidol Patchoulol Diterpene alcohols Phytol
Dialcohols	1,4-Butanediol 1,5-Pentanediol 2-Methyl-2-propyl-1,3-propanediol Diethylpropanediol Ethylene glycol
Trialcohols	Glycerol
Sterols	Cholesterol Ergosterol Lanosterol β-Sitosterol Stigmasterol
Fluoroalcohols	1,3-Difluoro-2-propanol 2,2,2-Trifluoroethanol 2-Fluoroethanol Nonafluoro-tert-butyl alcohol Trifluoromethanol
Preparations	Substitution of haloalkane Carbonyl reduction Ether cleavage Hydrolysis of epoxide Hydration of alkene Ziegler process
Reactions	Deprotonation Protonation Alcohol oxidation Glycol cleavage Nucleophilic substitution Fischer–Speier esterification Williamson ether synthesis Elimination reaction Nucleophilic substitution of carbonyl group Friedel-Crafts alkylation Nucleophilic conjugate addition Transesterification
Category