相转移催化合成对苯二甲酰氯的研究
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摘要
本文研究了以对苯二甲酸为原料,氯化亚砜为酰氯化试剂,采用相转移催化剂和固载催化剂合成对苯二甲酰氯的工艺。
首先,通过考察催化剂、溶剂、原料配比、反应时间、反应温度等因素对反应的影响确定了最佳的反应条件,并对反应机理进行了探讨。在该优化条件下,以苄基三乙基氯化铵为催化剂、物料摩尔配比为4:1、85℃、4h、无溶剂等条件下可实现收率96%以上,纯度98.8%以上。
其次,制备了四种新型的聚合物固载催化剂PS-CH_2(OCH_2CH_2)_4NR_3Cl,对所制备催化剂进行了红外光谱结构表征和季铵盐含量测定,并用于对苯二甲酸酰氯化,得出了适宜的合成工艺条件,即:对苯二甲酸16.6g、SOCl_230mL、甲苯32mL、催化剂3g、反应温度85℃、反应时间6h,可以实现收率89.6%,纯度99.6%,催化剂回收率93.6%。循环6次结果基本不变。
产物结构经过熔点、红外光谱、核磁共振等方法得以确证。并建立了对苯二甲酰氯柱前衍生反相高效液相色谱定量分析方法,采用SunFire C18柱,流动相为甲醇和水,方法的相对标准偏差RSD为0.1490%,平均回收率为99.53%。
In the paper,phase transfer catalyst and polymer-supported catalyst were used for the synthesis of terephthaloyl dichloride from terephthalic acid and thionyl chloride.
Firstly,effects of catalysts,solvents,solvent,reaction temperature,reaction time on yield and purity of the product were studied and the best response condition to the response determined.The reaction mechanism was proposed.The suited conditions were determined as:the mole ratio of thionyl chloride to terephthalic acid was 4:1, the reaction temperature was 85℃and reaction time was 4h under solvent-free condition.The yield and purity of terephthaloyl dichloride was not less than 96%and the purity was not less than 98.8%.
Secondly,four kinds of new polymer-supported catalysts were synthesized under the improved conditions,and were analyzed and attributed by IR and content determination.The catalytic system was used for the acyl chloride reaction of terephthalic acid,and the reaction mechanisms were discussed.The reaction conditions optimized are as follows:terephthalic acid 16.6g,SOCl_2 30mL,toluene 32mL,dosage of catalyst 3g,time 6h and temperature 85℃.Under the optimized condition,yield was 89.6%and the purity of terephthaloyl dichloride was 99.6%, with the catalyst recovery 93.6%.The catalytic activity remained stable after the six recycles.
The structure of the target product was identified by melting point determination, IR and 'H-NMR.A reversed phase high performance liquid chromatographic method with pre-column derivation was described for analyzing medical intermediate terephthaloyl dichloride.The SunFire C18 column was used with the mobile phase of methanol and water.The relative standard deviation and average recovery was 0.1490%and 99.53%.
首先,通过考察催化剂、溶剂、原料配比、反应时间、反应温度等因素对反应的影响确定了最佳的反应条件,并对反应机理进行了探讨。在该优化条件下,以苄基三乙基氯化铵为催化剂、物料摩尔配比为4:1、85℃、4h、无溶剂等条件下可实现收率96%以上,纯度98.8%以上。
其次,制备了四种新型的聚合物固载催化剂PS-CH_2(OCH_2CH_2)_4NR_3Cl,对所制备催化剂进行了红外光谱结构表征和季铵盐含量测定,并用于对苯二甲酸酰氯化,得出了适宜的合成工艺条件,即:对苯二甲酸16.6g、SOCl_230mL、甲苯32mL、催化剂3g、反应温度85℃、反应时间6h,可以实现收率89.6%,纯度99.6%,催化剂回收率93.6%。循环6次结果基本不变。
产物结构经过熔点、红外光谱、核磁共振等方法得以确证。并建立了对苯二甲酰氯柱前衍生反相高效液相色谱定量分析方法,采用SunFire C18柱,流动相为甲醇和水,方法的相对标准偏差RSD为0.1490%,平均回收率为99.53%。
In the paper,phase transfer catalyst and polymer-supported catalyst were used for the synthesis of terephthaloyl dichloride from terephthalic acid and thionyl chloride.
Firstly,effects of catalysts,solvents,solvent,reaction temperature,reaction time on yield and purity of the product were studied and the best response condition to the response determined.The reaction mechanism was proposed.The suited conditions were determined as:the mole ratio of thionyl chloride to terephthalic acid was 4:1, the reaction temperature was 85℃and reaction time was 4h under solvent-free condition.The yield and purity of terephthaloyl dichloride was not less than 96%and the purity was not less than 98.8%.
Secondly,four kinds of new polymer-supported catalysts were synthesized under the improved conditions,and were analyzed and attributed by IR and content determination.The catalytic system was used for the acyl chloride reaction of terephthalic acid,and the reaction mechanisms were discussed.The reaction conditions optimized are as follows:terephthalic acid 16.6g,SOCl_2 30mL,toluene 32mL,dosage of catalyst 3g,time 6h and temperature 85℃.Under the optimized condition,yield was 89.6%and the purity of terephthaloyl dichloride was 99.6%, with the catalyst recovery 93.6%.The catalytic activity remained stable after the six recycles.
The structure of the target product was identified by melting point determination, IR and 'H-NMR.A reversed phase high performance liquid chromatographic method with pre-column derivation was described for analyzing medical intermediate terephthaloyl dichloride.The SunFire C18 column was used with the mobile phase of methanol and water.The relative standard deviation and average recovery was 0.1490%and 99.53%.
引文
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