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Terminal epoxides react quantitatively with methanol in the presence of boron trifluoride to give both primary and secondary hydroxy methyl ethers. These derivatives are useful in the analysis of terminal epoxide mixtures by gas liquid chromatography. This procedure is compared with the conventional method and with a procedure in which the 1,2-epoxyalkanes are reduced to the corresponding secondary alcohols with LiAlH4. A statistical analysis of experimental data obtained from known mixtures of long chain epoxides is described. Results of this analysis demonstrate the improved accuracy and precision of the method as compared to the other methods investigated. LiAlH4reduction is the preferred method of analysis for the more reactive epoxides as well as for the cyclic epoxides. This procedure is particularly useful in the analysis of epoxides containing a tertiary carbon atom. The application of this technique to other epoxides is expected to improve their analysis, but further work is necessary.

Abstract: Terminal epoxides react quantitatively with methanol in the presence of boron trifluoride to give both primary and secondary hydroxy methyl ethers. These derivatives are useful in the analysis of terminal epoxide mixtures by gas liquid chromatography. This procedure is compared with the conventional method and with a procedure in which the 1,2-epoxyalkanes are reduced to the corresponding secondary alcohols with LiAlH4. A statistical analysis of experimental data obtained from known mixtures of long chain epoxides is described. Results of this analysis demonstrate the improved accuracy and precision of the method as compared to the other methods investigated. LiAlH4 reduction is the preferred method of analysis for the more reactive epoxides as well as for the cyclic epoxides. This procedure is particularly useful in the analysis of epoxides containing a tertiary carbon atom. The application of this technique to other epoxides is expected to improve their analysis, but further work is necessary.