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Title: The continuous acid-catalyzed dehydration of alcohols in supercritical fluids: A new approach to the cleaner synthesis of acetals, ketals, and ethers with high selectivity

Journal Article · · Journal of the American Chemical Society
DOI:https://doi.org/10.1021/ja991562p· OSTI ID:20013693

This report describes a new a continuous method for forming ethers, acetals and ketals using solid acid catalysts, DELOXAN ASP or AMBERLYST 15, and supercritical fluid solvents. In the case of ether formation, the authors observe a high selectivity for linear alkyl ethers with little rearrangement to give branches ethers. Such rearrangement is common in conventional synthesis. The approach is effective for a range of n-alcohols up to n-octanol and also for the secondary alcohol 2-propanol. In the reaction of phenol with an alkylating agent, the continuous reaction can be tuned to give preferential O- or C-alkylation with up to 49% O-alkylation with supercritical propene. The authors also investigate the synthesis of a range of cyclic ethers and show an improved method for the synthesis of THF from 1,4-butandiol under very mild conditions.

Research Organization:
Univ. of Nottingham (GB)
OSTI ID:
20013693
Journal Information:
Journal of the American Chemical Society, Vol. 121, Issue 46; Other Information: PBD: 24 Nov 1999; ISSN 0002-7863
Country of Publication:
United States
Language:
English