Methoxymethanol Explained

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]

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]

Notes and References

1. Maiwald . Michael . Fischer . Holger H. . Ott . Michael . Peschla . Roger . Kuhnert . Christian . Kreiter . Cornelius G. . Maurer . Gerd . Hasse . Hans . 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 . January 2003 . 42 . 2 . 259–266 . 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. . ALMA Detection of Interstellar Methoxymethanol (CH3OCH2OH) . The Astrophysical Journal . 2017 . 851 . 2 . L46 . 10.3847/2041-8213/aaa0c3 . en. 2017ApJ...851L..46M . 1712.03256 . 119211919 . free .
3. Hays . Brian M. . Widicus Weaver . Susanna L. . Theoretical Examination of O(¹D) Insertion Reactions to Form Methanediol, Methoxymethanol, and Aminomethanol . The Journal of Physical Chemistry A . 6 May 2013 . 117 . 32 . 7142–7148 . 10.1021/jp400753r. 23646865 . 2013JPCA..117.7142H .
4. Celik . Fuat E. . Lawrence . Henry . Bell . Alexis T. . Synthesis of precursors to ethylene glycol from formaldehyde and methyl formate catalyzed by heteropoly acids . Journal of Molecular Catalysis A: Chemical . June 2008 . 288 . 1–2 . 87–96 . 10.1016/j.molcata.2008.03.029.
5. Book: Dixneuf . Pierre H. . Soulé . Jean-François . Organometallics for Green Catalysis . 2019 . Springer . 978-3-030-10955-4 . 69–70 . en.
6. Motiyenko . R. A. . Millimeter-wave spectroscopy of methoxymethanol . 71st International Symposium on Molecular Spectroscopy . en . 21 June 2016 . 1 . 10.15278/isms.2016.TH04 . 2016isms.confETH04M . 2142/91121 . 978-1-5330-5390-9 . free.