Preparation and evaluation of a series of α‐hydroxy ethers from 9,10‐epoxystearates
2007
Moser, Bryan R. | Erhan, Sevim Z.
Several novel α‐hydroxy ethers were prepared by treatment of isobutyl 9,10‐epoxystearate with a number of aliphatic alcohols in the presence of acid catalyst in good overall yield from oleic acid. The low‐temperature behavior of each material was analyzed through cloud point (CP) and pour point (PP) determination. The most desirable α‐hydroxy ether prepared in this study was isobutyl 9(10)‐(2‐ethylhexoxy)‐10(9)‐hydroxystearate. Therefore, additional α‐hydroxy‐2‐ethylhexyl ethers were produced from alkyl 9,10‐epoxystearates (alkyl: butyl, hexyl, 2‐methylpentyl, 2‐ethylbutyl, 2‐ethylhexyl) to explore the effect of ester variability on CP and PP of the optimized 2‐ethylhexyl ether moiety. The most bulky ester group, 2‐ethylhexyl, exhibited the most favorable low‐temperature performance, which in the case of 2‐ethylhexyl 9(10)‐(2‐ethylhexoxy)‐10(9)‐hydroxystearate yielded a CP of –26 °C and a PP of –29 °C. An improved synthesis of 2‐ethylhexyl 9(10)‐(2‐ethylhexoxy)‐10(9)‐hydroxystearate was then developed from oleic acid. Lastly, in an effort to optimize yield, sulfuric acid at 10 mol‐% was found to be the most effective acid catalyst in the conversion of epoxides to α‐hydroxy ethers.
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