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{{Redirect-distinguish|Methylene glycol|Ethylene glycol}}
{{Short description|Organic compound (CH2(OH)2); simplest geminal diol}}
{{Chembox
{{Chembox
| Watchedfields = changed
| Watchedfields = changed
Line 12: Line 14:
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageNameR1 = Spacefill model of methanediol
| ImageNameR1 = Spacefill model of methanediol
| IUPACName = Methanediol<ref>{{Cite web|title = Methanediol - Compound Summary|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=79015|work = PubChem Compound|publisher = National Center for Biotechnology Information|accessdate = 20 October 2011|location = USA|date = 26 March 2005|at = Identification and Related Records}}</ref>
| PIN = Methanediol<ref>{{Cite web|title = Methanediol - Compound Summary|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=79015|work = PubChem Compound|publisher = National Center for Biotechnology Information|accessdate = 20 October 2011|location = USA|date = 26 March 2005|at = Identification and Related Records}}</ref>
| OtherNames = {{unbulleted list|Formaldehyde hydrate|Formaldehyde monohydrate|Methylene glycol}}
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| Abbreviations = MADOL
| Abbreviations = MADOL
| CASNo = 463-57-0
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 463-57-0
| CASNo_Ref = {{cascite|correct|??}}
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem = 79015
| UNII = 6Z20YM9257
| PubChem_Ref = {{Pubchemcite|correct|Pubchem}}
| ChemSpiderID = 71348
| PubChem = 79015
| ChemSpiderID = 71348
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 207-339-5
| ChEBI = 48397
| EINECS = 207-339-5
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 48397
| ChEBI_Ref = {{ebicite|correct|EBI}}
| Beilstein = 1730798
| Beilstein = 1730798
| SMILES = OCO
| SMILES = OCO
| StdInChI = 1S/CH4O2/c2-1-3/h2-3H,1H2
| StdInChI = 1S/CH4O2/c2-1-3/h2-3H,1H2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CKFGINPQOCXMAZ-UHFFFAOYSA-N
| StdInChIKey = CKFGINPQOCXMAZ-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C = 1
| C=1 | H=4 | O=2
⚫
| Appearance = Colourless liquid
| H = 4
| Density = {{val|1.199|u=g/cm3}} {{Citation needed|date=October 2021}}
| O = 2
⚫
| BoilingPtC = 194
| ExactMass = 48.021129372 g mol<sup>−1</sup>
| BoilingPt_notes = at 101 kPa {{Citation needed|date=October 2021}}
⚫
| Appearance = Colourless liquid
| VaporPressure = 16.1 Pa {{Citation needed|date=October 2021}}
| Density = 1.199 g cm<sup>−3</sup>
| RefractIndex = 1.401 {{Citation needed|date=October 2021}}
⚫
| BoilingPtC = 194
| pKa = 13.29<ref>{{cite journal|last=Bell|first=R. P.|author2=McTigue, P. T.|title=603. Kinetics of the aldol condensation of acetaldehyde|journal=Journal of the Chemical Society (Resumed)|year=1960|pages=2983|doi=10.1039/JR9600002983}}</ref>
| Boiling_notes = at 101 kPa
| VaporPressure = 16.1 Pa
| RefractIndex = 1.401
}}
}}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| FlashPt = 99.753 °C
| FlashPtC = 99.753
}}
}}
}}
}}


'''Methanediol''', also known as '''formaldehyde monohydrate''' or '''methylene glycol''', is a [[chemical compound]] with [[chemical formula]] CH<sub>4</sub>O<sub>2</sub>, or H<sub>2</sub>C(OH)<sub>2</sub>. It is the simplest [[geminal diol]], and formally the second simplest [[carbohydrate]] (after [[formaldehyde]]).
'''Methanediol''', also known as '''formaldehyde monohydrate''' or '''methylene glycol''', is an [[organic compound]] with [[chemical formula]] {{chem2|CH2(OH)2}}. It is the simplest [[geminal diol]]. In aqueous solutions it coexists with [[oligomer]]s (short polymers). The compound is closely related and convertible to the industrially significant derivatives [[paraformaldehyde]] ({{chem2|(CH2O)_{''n''} }}), [[formaldehyde]] ({{chem2|H2C\dO}}), and [[1,3,5-trioxane]] ({{chem2|(CH2O)3}}).<ref name=Ullmann/>


Methanediol is a product of the [[Hydration reaction|hydration]] of [[formaldehyde]] H<sub>2</sub>C=O, and predominates in water solution: the [[equilibrium constant]] being about 10<sup>3</sup>,<ref name="anslyn">
Methanediol is a product of the [[Hydration reaction|hydration]] of formaldehyde. The [[equilibrium constant]] for hydration is estimated to be 10<sup>3</sup>,<ref name="anslyn">
Eric V. Anslyn, Dennis A. Dougherty (2006), [http://books.google.com/books?id=gY-Sxijk_tMC&pg=PA544 ''Modern physical organic chemistry'']. University Science Books. ISBN 1891389319. 1095 pages
Eric V. Anslyn, Dennis A. Dougherty (2006), [https://books.google.com/books?id=gY-Sxijk_tMC&pg=PA544 ''Modern physical organic chemistry'']. University Science Books. {{ISBN|1-891389-31-9}}. 1095 pages</ref>{{chem2|CH2(OH)2}} predominates in dilute (<0.1%) solution. In more concentrated solutions, it oligomerizes to {{chem2|HO(CH2O)_{''n''}H}}.<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a11_619|title=Formaldehyde|year=2000|last1=Reuss|first1=Günther|last2=Disteldorf|first2=Walter|last3=Gamer|first3=Armin Otto|last4=Hilt|first4=Albrecht|isbn=3527306730}}</ref>
</ref> and a 5% by weight solution of [[formaldehyde]] in water is 80% methanediol.


==Occurrence==
The compound is of some relevance to [[astrochemistry]].<ref>''A theoretical study of the conversion of gas phase methanediol to formaldehyde'' Kent DR, Widicus SL, Blake GA, Goddard WA The Journal of Chemical Physics -- September 8, '''2003''' -- Volume 119, Issue 10, pp. 5117-5120 {{DOI|10.1063/1.1596392}}</ref>
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.<ref name="zhu">{{cite journal |last1=Zhu |first1=Cheng |last2=Kleimeier |first2=N. Fabian |last3=Turner |first3=Andrew M. |last4=Singh |first4=Santosh K. |last5=Fortenberry |first5=Ryan C. |last6=Kaiser |first6=Ralf I. |title=Synthesis of methanediol [CH 2 (OH) 2 ]: The simplest geminal diol |journal=Proceedings of the National Academy of Sciences |date=4 January 2022 |volume=119 |issue=1 |pages=e2111938119 |doi=10.1073/pnas.2111938119 |doi-access=free | pmid=34969838 |pmc=8740743 |bibcode=2022PNAS..11911938Z }}</ref>
Methanediol is listed as one of the main ingredients of "[[Brazilian hair straightening|Brazilian blowout]]", a hair-straightening formula marketed in the US — even though the [[California]]-based manufacturer claims that the product contains no formaldehyde.<ref>http://www.osha.gov/SLTC/formaldehyde/hazard_alert.html</ref>

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.<ref name="zhu"/>

==Safety==
Methanediol, rather than formaldehyde, is listed as one of the main ingredients of "[[Brazilian hair straightening|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.<ref>{{Cite web|url=https://www.osha.gov/SLTC/formaldehyde/hazard_alert.html|title=Hair Smoothing Products That Could Release Formaldehyde|publisher=Occupational Safety and Health Administration|website=www.osha.gov}}</ref><ref>{{cite web|title=Industry News|author=SpecialChem |url=http://www.specialchem4cosmetics.com/markets/hair-care/news.aspx?id=5947&lr=chal2d161210&li=100091733}}</ref> 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.<ref name="Golden">{{cite journal|last1=Golden|first1=R.|last2=Valentini|first2=M.|title=Formaldehyde and methylene glycol equivalence: Critical assessment of chemical and toxicological aspects|journal=[[Regulatory Toxicology and Pharmacology]]|date=July 2014|volume=69|issue=2|pages=178–186|doi=10.1016/j.yrtph.2014.03.007|pmid=24709515|doi-access=free}}</ref>


==See also==
==See also==
* [[Orthoformic acid]] (methanetriol)
* [[Orthoformic acid]] (methanetriol)
* [[Orthocarbonic acid]] (methanetetraol)
* [[Orthocarbonic acid]] (methanetetrol)


==References==
==References==


{{Reflist}}
{{Reflist}}
{{Alcohols}}


[[Category:Hydrates]]
[[Category:Hydrates]]
[[Category:Carbohydrates]]
[[Category:Carbohydrates]]
[[Category:Diols]]
[[Category:Geminal diols]]
[[Category:Sugar alcohols]]

{{Alcohol-stub}}

[[fr:Méthanediol]]
[[ja:メタンジオール]]

Latest revision as of 13:53, 24 October 2024

"Methylene glycol" redirects here. Not to be confused with Ethylene glycol.
Methanediol
Skeletal formula of methanediol with some explicit hydrogens added
Skeletal formula of methanediol with some explicit hydrogens added
Spacefill model of methanediol
Spacefill model of methanediol
Ball and stick model of the methanediol
Names
Preferred IUPAC name
Methanediol[1]
Other names
  • Formaldehyde hydrate
  • Formaldehyde monohydrate
  • Methylene glycol
Identifiers
3D model (JSmol)
Abbreviations MADOL
1730798
ChEBI
ChemSpider
ECHA InfoCard 100.006.673 Edit this at Wikidata
EC Number
  • 207-339-5
UNII
  • InChI=1S/CH4O2/c2-1-3/h2-3H,1H2 checkY
    Key: CKFGINPQOCXMAZ-UHFFFAOYSA-N checkY
  • OCO
Properties
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]
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).
checkY verify (what is checkY☒N ?)

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]

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.
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