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Supplementary Materials

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  • Fig. S1. The structures of ILs used in this study.
  • Fig. S2. Product distributions for the oxidative transformation of propanol to propyl propionate in EMIM OAc.
  • Fig. S3. NMR spectra of benzaldehyde and EMIM OAc.
  • Fig. S4. NMR spectra of the mixture of benzaldehyde and EMIM OAc.
  • Fig. S5. 1H NMR spectra of the reaction media of the oxidative esterification reaction of benzyl alcohol (that is, the reaction in Table 1, entry 1) after 3- (yellow) and 12-hour reaction (green), together with that of the mixture of benzaldehyde and EMIM OAc (red).
  • Fig. S6. Recycling of EMIM OAc for oxidative esterification of benzyl alcohol and ethanol.
  • Fig. S7. Possible acid-base equilibrium in EMIM OAc.
  • Fig. S8. Effects of free carbene (products of the reaction between azolium salts A or B and DBU) on the oxidative reactions of benzyl alcohol and benzyl aldehyde.
  • Fig. S9. Isotope labeling experiments with 18O-enriched benzyl alcohol.
  • Fig. S10. Mass spectra of substrates and products for the experiments with 18O-enriched benzyl alcohol.
  • Fig. S11. 1H NMR spectrum of mixture of benzyl alcohol and EMIM OAc (molar ratio of benzyl alcohol to EMIM OAc = 1:1).
  • Fig. S12. 1H NMR spectrum of mixture of benzyl alcohol and EMIM OAc (molar ratio of benzyl alcohol to EMIM OAc = 1:5).
  • Fig. S13. 1H NMR spectra of mixture of benzyl alcohol and EMIM TFA (molar ratio of benzyl alcohol to EMIM TFA = 1:1).
  • Fig. S14. 1H NMR spectra of mixture of benzyl alcohol and EMIM TFA (molar ratio of benzyl alcohol to EMIM TFA = 1:5).
  • Fig. S15. FTIR spectra of benzyl alcohol, EMIM OAc, and their mixtures with various molar ratios.
  • Fig. S16. DOSY NMR spectra.
  • Fig. S17. 1H NMR spectrum of EMIM OAc before (above) and after (below) drying in vacuum.
  • Fig. S18. Variation of moisture content and pH of the reaction media during the oxidative esterification reaction.
  • Fig. S19. Effects of water content for the oxidative esterification of benzyl alcohol.
  • Table S1. Self-esterification of benzyl alcohol to benzyl benzoate in various ILs with or without additives.
  • Table S2. Chemical shifts and FWHM of the hydroxyl group resonance band in 1H NMR spectra of the mixtures of benzyl alcohol and EMIM OAc with various molar ratios.
  • Table S3. Chemical shifts and FWHM of the hydroxyl group resonance band in 1H NMR spectra of mixture of benzyl alcohol and BMIM TFA with various molar ratios.
  • Table S4. Chemical shifts and FWHM of the hydroxyl group resonance band in 1H NMR spectra of mixture of benzyl alcohol and EMIM BF4 with various molar ratios.
  • Table S5. Summary of assignments and shifts of frequencies (cm−1) of absorption bands in the FTIR spectra in fig. S15. (ν, stretch; s, symmetric; as, antisymmetric).
  • Table S6. Summary of diffusion coefficients.

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