Catalytic synthesis of methacrolein via the condensation of formaldehyde and propionaldehyde with L-proline,Green Chemistry

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Catalytic synthesis of methacrolein via the condensation of formaldehyde and propionaldehyde with L-proline
Green Chemistry ( IF 9.3 ) Pub Date : 2020-05-19 , DOI: 10.1039/d0gc00726a
Jiayuan Yu _{1,

2,

3,

4,

5} , Anker Degn Jensen _{6,

7,

8,

9} , Lei Wang _{1,

2,

3,

4,

5} , Chunshan Li _{1,

2,

3,

4,

5} , Suojiang Zhang _{1,

2,

3,

4,

5}

Affiliation

Methacrolein (MAL) is an important chemical for the manufacture of methyl methacrylate and a key monomer in many polymerization reactions. In this study, L-proline was investigated as the catalyst for the aldol condensation of formaldehyde and propionaldehyde to produce MAL. The catalytic activity of the reaction system was closely related to the competition between the main reaction synthesizing MAL and the side reaction producing 2-methyl-2-pentenal, which could be modified by adjusting the operating parameters. The influences of several operating conditions, including temperature, reaction time and water content, on the catalytic performance of the system were systematically studied via a series of single-factor experiments, and the optimized reaction conditions were obtained. The mechanistic investigation via ESI-MS indicated that the reaction pathway followed the Mannich route. Experimental and theoretical kinetic analyses of the L-proline-catalyzed aldol condensation reaction were performed, and the reaction orders of the reactants were obtained by regression. The results showed that L-proline was an efficient catalyst for the production of MAL via aldol condensation under mild conditions.

中文翻译：

甲醛和丙醛与L-脯氨酸的缩合催化合成甲基丙烯醛

甲基丙烯醛（MAL）是制造甲基丙烯酸甲酯的重要化学品，并且是许多聚合反应中的关键单体。在该研究中，研究了L-脯氨酸作为甲醛和丙醛的醛醇缩合以产生MAL的催化剂。反应体系的催化活性与合成MAL的主要反应与产生2-甲基-2-戊烯醛的副反应之间的竞争密切相关，可以通过调节操作参数来改变。通过系统研究了温度，反应时间和含水量等几种操作条件对系统催化性能的影响。通过一系列单因素实验，获得了最佳的反应条件。通过ESI-MS的机理研究表明反应路径遵循曼尼希路线。对L-脯氨酸催化的醛醇缩合反应进行了实验和理论动力学分析，并通过回归获得了反应物的反应顺序。结果表明，L-脯氨酸是在温和条件下通过羟醛缩合生产MAL的有效催化剂。

更新日期：2020-07-06

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