Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula C3H4O. It is the simplest stable alcohol containing an alkyne functional group.[3] Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents.
Reactions and applications
Propargyl alcohol polymerizes with heating or treatment with base. It is used as a corrosion inhibitor, a metal complex solution, a solvent stabilizer and an electroplating brightener additive. It is also used as an intermediate in organic synthesis. Secondary and tertiary substituted propargylic alcohols undergo catalyzed rearrangement reactions to form α,β-unsaturated carbonyl compounds via the Meyer–Schuster rearrangement and others. It can be oxidized to propynal[4] or propargylic acid.
As an indication of the electronegativity of an sp carbon, propargyl alcohol is significantly more acidic (pKa = 13.6) compared to its sp2-containing analog allyl alcohol (pKa = 15.5), which is in turn more acidic than the fully saturated (sp3 carbons only) n-propyl alcohol (pKa = 16.1).[5]
Preparation
Propargyl alcohol is produced by the copper-catalysed addition of formaldehyde to acetylene as a by-product of the industrial synthesis of but-2-yne-1,4-diol.[6] It can also be prepared by dehydrochlorination of 3-chloro-2-propen-1-ol by NaOH.[7]
Safety
Propargyl alcohol is a flammable liquid, toxic by inhalation, highly toxic by ingestion, toxic by skin absorption, and corrosive.[citation needed]
See also
References
- ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0527". National Institute for Occupational Safety and Health (NIOSH).
- ^ Record of Prop-2-yn-1-ol in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 11 March 2020.
- ^ Merck Index, 11th Edition, 7819
- ^ J. C. Sauer (1956). "Propionaldehyde". Organic Syntheses. 36: 66; Collected Volumes, vol. 4, p. 813.
- ^ Anslyn, Eric V., 1960- (2006). Modern physical organic chemistry. Dougherty, Dennis A., 1952-. Mill Valley, California: University Science Books. ISBN 1-891389-31-9. OCLC 55600610.
{{cite book}}: CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link) - ^ Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter. "Alcohols, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_279. ISBN 978-3527306732..
- ^ [1] J. Am. Chem. Soc., 1944, 66 (2), pp 285–287
External links
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