Abstract
By-products (phenyl salicylate, phenyl 4-hydroxybenzoate, and xanthone) from transesterification between phenol and dimethyl carbonate (DMC) were qualitatively analyzed by gas chromatography-mass spectrometry, and a gas chromatographic method with directed injection for simultaneous quantitative analysis of the product (DPC) and by-products of the transesterification has been established. Based on the results of qualitative and quantitative analyses, the mechanism of the by-products generation was preliminarily deduced. The sample for quantitative analysis was directly diluted in acetone, and related compounds were separated on an HP-5 capillary column and detected by a hydrogen flame ionization detector (FID). The product and by-products were well separated, the correlation coefficients (r) within the concentration range of 1.0 μg/mL–100 μg/mL were ≥0.9997, the relative standard deviations were between 0.5% and 4.4%, spiked recoveries were between 91.5% and 105.6%, and detection limits were between 0.11 and 0.18 μg/mL. The established method is simple, rapid, accurate, sensitive, and highly specific. It is suitable for simultaneous qualitative and quantitative analyses of the product and by-products of transesterification between phenol and DMC.
Highlights
Nontoxic and environmentally friendly diphenyl carbonate (DPC) is an important “green” chemical product, which may be used for synthesizing many important organic compounds and polymer materials [1, 2] and can, superseding highly toxic phosgene, react with bisphenol A to produce polycarbonate (PC) with excellent performance [3, 4]
Since PC is extensively used in mechanical manufacture, electronic appliances, military and lighting industries, security, medical devices, etc., the demand for the raw material for PC synthesis, DPC, has been rising sharply and, as a result, synthetic processes of DPC have become a hot research field in recent years [5, 6]
In oxidative carbonylation of phenol, DPC is synthesized from phenol, O2, and CO by a one-step reaction under the catalytic effect of Pd. e used raw materials are cheap and available. e process is simple, and the atom utilization rate is high
Summary
Nontoxic and environmentally friendly diphenyl carbonate (DPC) is an important “green” chemical product, which may be used for synthesizing many important organic compounds and polymer materials [1, 2] and can, superseding highly toxic phosgene, react with bisphenol A to produce polycarbonate (PC) with excellent performance [3, 4]. Chlorine-containing impurities will be present in the product [7, 8] For these reasons, the phosgene method has been gradually replaced by other methods. Phosgene-free approaches for synthesis of DPC mainly include oxidative carbonylation of phenol and transesterification. In oxidative carbonylation of phenol, DPC is synthesized from phenol, O2, and CO by a one-step reaction under the catalytic effect of Pd. e used raw materials are cheap and available. E method involving transesterification between phenol and DMC has the advantages of a simple process, high atom utilization rate, and high selectivity. Based on previous studies of the transesterification [24,25,26,27,28,29], a method has been established for qualitative and quantitative analysis of the product and rearrangement products of transesterification between phenol and DMC
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