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The reaction between methanol and sulfuric acid (SA) was investigated using Raman and vibrational broad bandwidth sum frequency generation spectroscopies. Evidence for the formation of methyl hydrogen sulfate (MHS) was obtained by the presence of a new peak in the 800 cm -1 region, not present in either the neat methanol or concentrated sulfuric acid spectra. This peak is attributed to the singly bonded OSO symmetric stretch of MHS. The maximum yield of MHS with a large SA excess (7 SA/1 methanol) is shown to be (95 ± 5)% at −(15 ± 2) °C. No evidence was found to suggest formation of dimethyl sulfate.
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Loon et al. (2004) studied this question.
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