Liu, Dongliang; Thomas, Tiju; Gong, Hong; Li, Fei; Li, Qiang; Song, Lijuan; Azhagan, Tamil; Jiang, Heng; Yang, Minghui published the artcile< A mechanism of alkali metal carbonates catalysing the synthesis of β-hydroxyethyl sulfide with mercaptan and ethylene carbonate>, Recommanded Product: 2-(Phenylthio)ethanol, the main research area is alkyl mercaptan dioxolanone potassium carbonate catalyst ring opening hydroxyethylation; hydroxyethyl alkyl sulfide preparation green chem.
A new and green route to synthesize 2-hydroxyethyl n-alkyl sulfide with n-alkyl mercaptan and ethylene carbonate (EC) in the presence of alkali carbonates as catalysts and revealed the mechanism by experiments and theor. calculations The reaction reported proceeded rapidly with high yields when it was performed at 120° C and the catalytic loading is ∼1 mol%. This protocol was applicable to other mercaptans to synthesize the corresponding β-hydroxyethyl sulfide. D. functional theory-based calculations show the energy profile for the reaction pathway. The rate-determining step is the ring-opening of EC. A neg. charged O atom of alkali carbonates approached the S atom of -SH under the influence of hydrogen bonds. An activated S atom that carried more neg. charge serves as a nucleophilic reagent and assists in the ring-opening of EC by reducing the Mayer bond orders of the C1-O1 bond in EC. Alkali cations also contribute to the C1-O1 bond cleavage. The energy barrier for the ring-opening of EC decreases with the decrease of electronegativity of alkali cations. Subsequent transference of a H atom led to the formation of β-hydroxyethyl sulfide, the dissociation of CO2 and the reduction of K2CO3.
Organic & Biomolecular Chemistry published new progress about Electrostatic potential energy surface. 699-12-7 belongs to class alcohols-buliding-blocks, and the molecular formula is C8H10OS, Recommanded Product: 2-(Phenylthio)ethanol.
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