Bioderived Acrylates from Alkyl Lactates via Pd-Catalyzed Hydroesterification,ACS Sustainable Chemistry & Engineering

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Bioderived Acrylates from Alkyl Lactates via Pd-Catalyzed Hydroesterification
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2018-07-19 00:00:00 , DOI: 10.1021/acssuschemeng.8b02359
Gereon M. Yee ₁ , Marc A. Hillmyer ₁ , Ian A. Tonks ₁

Affiliation

The conversion of methyl and ethyl lactate to their corresponding alkyl 2-(propionyloxy)propanoate esters was achieved by Pd catalyzed hydroesterificative coupling with carbon monoxide (CO) and ethylene (C₂H₄) at moderate temperatures and CO/C₂H₄ pressures. A screening of reaction conditions showed that the reaction could be carried out at low loadings of catalyst, which was generated in situ from inexpensive and commercially available reagents. High conversions and product yields were obtained in a variety of solvents and even under neat conditions. Product analysis identified transesterification to be the primary competing reaction, which could be mitigated by changing solvents, as well as minimizing the amount of excess acid present in solution. Pyrolysis of methyl and ethyl 2-(propionyloxy)propanoate transformed these esters into their respective acrylates suitable for subsequent polymerization, along with propionic acid as a valuable coproduct.

中文翻译：

通过钯催化的加氢酯化反应从乳酸烷基酯中生物衍生的丙烯酸酯

在中等温度和CO / C ₂ H ₄压力下，通过Pd与一氧化碳（CO）和乙烯（C ₂ H ₄）催化加氢酯化偶联，将乳酸甲酯和乳酸乙酯转化为其相应的2-（丙酰氧基）丙酸烷基酯。。反应条件的筛选表明，该反应可以在原位产生的低催化剂负载下进行从便宜的和可商购的试剂中提取。在各种溶剂中，甚至在纯净条件下，都可以实现高转化率和产物收率。产品分析确定酯交换反应是主要的竞争反应，可以通过更换溶剂和最大程度减少溶液中过量酸的含量来缓解。2-（丙酰氧基）丙酸甲酯和乙酯的热解将这些酯与丙酸（作为有价值的副产物）一起转化为各自的丙烯酸酯，适合随后进行聚合。

更新日期：2018-07-19

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