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The solid/liquid phase transfer effect of 18-crown-6 for the potassium salts catalyzed β-hydroxyethylation of mercaptan with ethylene carbonate

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Abstract

Under atmospheric pressure and solvent-free conditions, β-hydroxyethyl alkyl sulfides (RSCH2CH2OH) were synthesized using crown ether as phase transfer agent, inorganic acid potassium salts (KA) as catalyst, ethylene carbonate (EC) and mercaptan (RSH) as raw materials. The solid/liquid phase transfer effect of 18-crown-6 on the β-hydroxyethylation of RSH catalyzed by KA and the effect of EC/RSH molar ratio on the selectivity of RSCH2CH2OH were systematically investigated. The results showed that 18-crown-6 itself had no catalytic activity. Compared with KA alone, the synergistic catalysis of KA with 18-crown-6 could significantly accelerate the reaction rate and the conversion of RSH was greatly increased. In the case of 0.3 mol% K2CO3 in combination with 0.6 mol% 18-crown-6 catalyzed β-hydroxyethylation of n-octyl mercaptan, the conversion of n-C8H17SH reached 100%, whereas the selectivity of n-C8H17SCH2CH2OH gradually decreased from 97.6 to 90.3% with increasing the molar ratio of EC/n-C8H17SH from 1.02 to 1.50, and the by-products were vinyl n-octyl sulfide and ethylene glycol. Under solvent-free conditions, the phase interface restriction between the KA catalyst and the liquid-phase reactants can be effectively broken after the addition of 18-crown-6, thereby enhancing the β-hydroxyethylation of RSH reaction efficiently.

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Authors and Affiliations

  1. School of Petrochemical Engineering, Liaoning Petrochemical University, Fushun, People’s Republic of China

    Zihan Zhang, Zhaoyang Xu, Rui Wang, Fei Li, Hong Gong & Heng Jiang

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  1. Zihan Zhang
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  2. Zhaoyang Xu
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  3. Rui Wang
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  4. Fei Li
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  5. Hong Gong
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  6. Heng Jiang
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Correspondence to Heng Jiang.

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Zhang, Z., Xu, Z., Wang, R. et al. The solid/liquid phase transfer effect of 18-crown-6 for the potassium salts catalyzed β-hydroxyethylation of mercaptan with ethylene carbonate. Monatsh Chem 154, 407–416 (2023). https://doi.org/10.1007/s00706-023-03056-5

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