Organotin Compounds as Catalysts for Disproportionation of Methyl Phenyl Carbonate to Diphenyl Carbonate†

doi:10.7503/cjcu20140334

Abstract

Abstract:

The catalytic performances of organotin compounds for the disproportionation of methyl phenyl carbonate(MPC) to diphenyl carbonate(DPC) were investigated. The electronic effect and steric hindrance for the disproportionate reactivity of MPC to DPC catalyzed by organotin compounds were discussed. The results show that the organotin compound is used as Lewis acid to catalyze the disproportionation of MPC, the electronic effect and steric hindrance of the coordinating groups affect the acidity of active tin centers and therefore influence the reactivity. Moreover, the influence of electronic effect is greater than that of the steric hindrance. Butyltinhydroxide-oxide[BuSnO(OH)] catalyst exhibits the best catalytic performance. Under the optimum reaction conditions[n(Cat.)/n(MPC)=0.02, 180 ℃, 2.5 h], the conversion of MPC is up to 89.7% and the selectivity of DPC is 99.3%.

Key words: Methyl phenyl carbonate, Diphenyl carbonate, Disproportionaton reaction, Butyltinhydroxide-oxide, Organotin compound, Catalytic performance

CLC Number:

O643

TrendMD:

WANG Songlin, ZHANG Yuanzhuo, CHEN Yong, TANG Rongzhi, CHEN Tong, WANG Gongying. Organotin Compounds as Catalysts for Disproportionation of Methyl Phenyl Carbonate to Diphenyl Carbonate^†[J]. Chem. J. Chinese Universities, 2014, 35(10): 2177.

Figures/Tables 5

Table 1 Catalytic performance of organotin compounds for the disproportionation of MPC*

Catalyst	Conversion of MPC(%)	Yield(%)		Selectivity of DPC(%)	TON
Catalyst	Conversion of MPC(%)	DPC	Anisole	Selectivity of DPC(%)
	trace
Bu₃SnCl	49.5	49.4	0.1	99.8	25
Bu₃SnOSnBu₃	65.3	65.1	0.2	99.7	33
Bu₂Sn(OCOC₁₁H₂₃)₂	81.3	80.0	1.3	98.4	40
Bu₂SnO	86.7	86.2	0.4	99.4	43
BuSnO(OH)	89.7	89.1	0.6	99.3	45

Fig.1 Effect of the reaction time on the disproportionation of MPC MPC: 150 mmol, temperature: 180 ℃, catalyst: BuSnO(OH), molar ratio of BuSnO(OH) to MPC: 0.015.

Fig.2 Effect of the reaction temperature on thedisproportionation of MPC MPC: 150 mmol, time: 2.5 h, catalyst: BuSnO(OH), molar ratio of BuSnO(OH) to MPC: 0.015.

Fig.3 Effect of the catalyst amount on thedisproportionation of MPC MPC: 150 mmol, temperature: 180 ℃,time: 2.5 h, catalyst: BuSnO(OH).

Scheme 1 Plausible mechanism for disproportionation of MPC to DPC

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