Methoxymethanol

Methoxymethanol is a chemical compound which is both an ether and an alcohol, a hemiformal.[1] The structural formula can be written as CH3OCH2OH. It has been discovered in space.[2]

Methoxymethanol
Names
Preferred IUPAC name
Methoxymethanol
Other names
Formaldehyde methyl hemiacetal
Identifiers
3D model (JSmol)
1900186
ChEBI
ChemSpider
ECHA InfoCard 100.022.476
EC Number
  • 224-722-2
UNII
Properties
C2H6O2
Molar mass 62.068 g·mol−1
Density 0.948
Hazards
GHS pictograms
GHS Signal word Warning
H226, H302, H371
P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P301+312, P303+361+353, P309+311, P330, P370+378, P403+235, P405, P501
Flash point 39.9 °C (103.8 °F; 313.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Formation

Methoxymethanol forms spontaneously when a water solution of formaldehyde and methanol are mixed.[3][1] or when formaldehyde is bubbled through methanol.[4]

In space methoxymethanol can form when methanol radicals (CH2OH or CH3O) react. These are radiolysis products derived when ultraviolet light or cosmic rays hit frozen methanol.[3]

Methanol can react with carbon dioxide and hydrogen at 80°C and some pressure with a ruthenium or cobalt catalyst, to yield some methoxymethanol.[5]

Properties

Different conformations of the molecule are Gauche-gauce (Gg), Gauche-gauce' (Gg'), and Trans-gauche (Tg).[6]

References
  1. Maiwald, Michael; Fischer, Holger H.; Ott, Michael; Peschla, Roger; Kuhnert, Christian; Kreiter, Cornelius G.; Maurer, Gerd; Hasse, Hans (January 2003). "Quantitative NMR Spectroscopy of Complex Liquid Mixtures: Methods and Results for Chemical Equilibria in Formaldehyde−Water−Methanol at Temperatures up to 383 K". Industrial & Engineering Chemistry Research. 42 (2): 259–266. doi:10.1021/ie0203072.
  2. McGuire, Brett A.; Shingledecker, Christopher N.; Willis, Eric R.; Burkhardt, Andrew M.; El-Abd, Samer; Motiyenko, Roman A.; Brogan, Crystal L.; Hunter, Todd R.; Margulès, Laurent; Guillemin, Jean-Claude; Garrod, Robin T.; Herbst, Eric; Remijan, Anthony J. (2017). "ALMA Detection of Interstellar Methoxymethanol (CH3OCH2OH)". The Astrophysical Journal. 851 (2): L46. arXiv:1712.03256. Bibcode:2017ApJ...851L..46M. doi:10.3847/2041-8213/aaa0c3. S2CID 119211919.
  3. Hays, Brian M.; Widicus Weaver, Susanna L. (6 May 2013). "Theoretical Examination of O(1D) Insertion Reactions to Form Methanediol, Methoxymethanol, and Aminomethanol". The Journal of Physical Chemistry A. 117 (32): 7142–7148. Bibcode:2013JPCA..117.7142H. doi:10.1021/jp400753r. PMID 23646865.
  4. Celik, Fuat E.; Lawrence, Henry; Bell, Alexis T. (June 2008). "Synthesis of precursors to ethylene glycol from formaldehyde and methyl formate catalyzed by heteropoly acids". Journal of Molecular Catalysis A: Chemical. 288 (1–2): 87–96. doi:10.1016/j.molcata.2008.03.029.
  5. Dixneuf, Pierre H.; Soulé, Jean-François (2019). Organometallics for Green Catalysis. Springer. pp. 69–70. ISBN 9783030109554.
  6. Motiyenko, R. A. (21 June 2016). "Millimeter-wave spectroscopy of methoxymethanol". hdl:2142/91121. Cite journal requires |journal= (help)
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