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Alkoxyalkyl‐substituted glycerol acetals: New hydrophobic intermediates for surfactant synthesis
Author(s) -
Piasecki Andrzej
Publication year - 1992
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02635802
Subject(s) - acrolein , chemistry , crotonaldehyde , glycerol , hydroxymethyl , hydrolysis , organic chemistry , acetal , aqueous solution , ketone , pulmonary surfactant , alcohol , catalysis , biochemistry
In acid‐catalyzed, one‐step reactions of monofunctional alcohol (I) and glycerol mixture with a simple α,β‐unsaturated carbonyl compound (acrolein, crotonaldehyde or methylvinyl ketone), four component glycerol acetals [mixtures of cis ‐+ trans ‐2‐(2‐alkoxyalkyl)‐substituted derivatives of 4‐hydroxymethyl‐1,3‐dioxolanes and 5‐hydroxy‐1,3‐dioxanes] or two component glycerol ketals [mixtures of cis ‐+ trans ‐2‐(2‐alkoxyethyl)‐2‐methyl‐4‐hydroxymethyl‐1,3‐dioxolanes] were obtained, respectively. These compounds may be used as a new group of hydrophobic intermediates for synthesis of chemodegradable surfactants, which rapidly hydrolyze to nonsurfactant compounds in acidic aqueous solutions. Methods of synthesis, yields, compositions and chemical structures of components of reaction products, and products of their chemical degradation have been discussed.