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首页> 美国政府科技报告 >Study of the Kinetics and Mechanism of the Base-Catalysed Esterification of Tetrachloroterephthaloyl Chloride with High-Performance Liquid Chromatography and Carbon-13 Fourier-Transform Nuclear Magnetic Resonance Spectroscopy
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Study of the Kinetics and Mechanism of the Base-Catalysed Esterification of Tetrachloroterephthaloyl Chloride with High-Performance Liquid Chromatography and Carbon-13 Fourier-Transform Nuclear Magnetic Resonance Spectroscopy

机译：高效液相色谱 - 碳-13傅里叶变换核磁共振谱研究碱催化四氯对苯二甲酰氯酯化反应动力学及机理

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Interest in tetrachloroterephthaloyl chloride (2,3,5,6-tetrachlorobenzene, 1,4-dicarbonyl dichloride; designated in this paper as 'R') originated with incoporating tetrachloroterephthaloyl groups into selective stationary phases for gas chromatography, attaching them to solid supports, and their potential use as derivatives and in polyesters. Using high-performance liquid chromatography (h.p.l.c.) to study the rise and fall of intermediate concentrations with retentions, we have now obtained evidence on the organic base-catalysed reaction of R in methanol (with some tetrahydrofuran (THF) for initial dissolution of R) to support the hypothesized four-step path of Figure 1. With pyridine base the aromatic dichloride (R) reacts to form pyridinium ion (N) which reacts further to form a dipyridinium ion (N). The dipyridinium ion reacts with methanol to form a monomethyl ester salt (O), N-(4-methoxycarbonyl-2,3,5,6- tetrachlorobenzoyl)pyridinium chloride, which reacts to form the product, dimethyl tetrachloroterephthalate (P). The solvent effects on the pyridine-catalysed reaction rate and negative entropy of activation might be explained with ion solvation by the methanol.

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