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Role of Anhydride in the Ketonization of Carboxylic Acid: Kinetic Study on Dimerization of Hexanoic Acid
Industrial & Engineering Chemistry Research ( IF 3.8 ) Pub Date : 2017-01-17 , DOI: 10.1021/acs.iecr.6b04605 Yesol Woo 1 , Yunsu Lee 2, 3 , Jae-Wook Choi 2 , Dong Jin Suh 2 , Chang-Ha Lee 3 , Jeong-Myeong Ha 2 , Myung-June Park 1, 4
Industrial & Engineering Chemistry Research ( IF 3.8 ) Pub Date : 2017-01-17 , DOI: 10.1021/acs.iecr.6b04605 Yesol Woo 1 , Yunsu Lee 2, 3 , Jae-Wook Choi 2 , Dong Jin Suh 2 , Chang-Ha Lee 3 , Jeong-Myeong Ha 2 , Myung-June Park 1, 4
Affiliation
Ketonization of hexanoic acid (CH3(CH2)4COOH) to produce 6-undecanone ((CH3(CH2)4)2CO) was performed and the reaction pathway was investigated through a kinetic study. Unlike studies suggesting β-keto acid as an undetectable intermediate of ketonization, hexanoic anhydride ((CH3(CH2)4)COOCO(CH2)4CH3) was observed to form as a result of the condensation of two hexanoic acid molecules by the loss of a water molecule. In order to investigate the role of hexanoic anhydride on the ketonization reaction, this kinetic study compared the performances of the reaction rate equations under different models for the reaction mechanism. Results indicate that ketonization occurs by the condensation of two hexanoic acid molecules producing hexanoic anhydride, followed by decarboxylation to produce 6-undecanone. By contrast, the formation of a β-keto acid is not observed in any experimental attempt.
中文翻译:
酸酐在羧酸酮化中的作用:己酸二聚的动力学研究
对己酸 (CH3(CH2)4COOH) 进行酮化生成 6-十一酮 ((CH3(CH2)4)2CO),并通过动力学研究研究反应途径。与研究表明 β-酮酸是无法检测到的酮化中间体不同,观察到己酸酐 ((CH3(CH2)4)COOCO(CH2)4CH3) 是由于两个己酸分子因失去一个水分子。为了研究己酸酐对酮化反应的作用,本动力学研究比较了反应机理在不同模型下的反应速率方程的表现。结果表明,酮化是通过两个己酸分子缩合产生己酸酐,然后脱羧产生 6-十一酮而发生的。相比之下,
更新日期:2017-01-17
中文翻译:
酸酐在羧酸酮化中的作用:己酸二聚的动力学研究
对己酸 (CH3(CH2)4COOH) 进行酮化生成 6-十一酮 ((CH3(CH2)4)2CO),并通过动力学研究研究反应途径。与研究表明 β-酮酸是无法检测到的酮化中间体不同,观察到己酸酐 ((CH3(CH2)4)COOCO(CH2)4CH3) 是由于两个己酸分子因失去一个水分子。为了研究己酸酐对酮化反应的作用,本动力学研究比较了反应机理在不同模型下的反应速率方程的表现。结果表明,酮化是通过两个己酸分子缩合产生己酸酐,然后脱羧产生 6-十一酮而发生的。相比之下,