Study on the reaction between bisphenol A and dimethyl carbonate over organotin oxide

Organotin oxide was used to catalyze the reaction between BPA (bisphenol A) and DMC (dimethyl carbonate), and Ph2SnO (diphenyltin oxide) displays the excellent catalytic performance in transesterification and O-methylation. However, Bu2SnO (dibutyltin oxide), (PhCH2)2SnO (dibenzyltin oxide) and (C6H11)2SnO (dicyclohexyltin oxide) exhibited weaker catalytic activity but higher selectivity for C-methylation product formation. The π–π function between Ph2SnO and BPA provided more chances for their interaction, and π–d interaction between phenyl ring and Sn resulted in catalyst having higher activity in transesterification and O-methylation. O-methylation product formation over Ph2SnO comes from transesterification product decomposition not from direct methylation of BPA with DMC.

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► Ph2SnO selectively catalyzes O-methylation product formation from BPA and DMC.
► Alkyltin oxide catalyzes C-methylation of BPA with DMC.
► Ph2SnO catalyzes transesterification products decomposition into O-methylation products.
► Transesterification products are more stable over alkyltin oxide.