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Direct synthesis of acrylate monomers in heterogeneous continuous flow processes†
Reaction Chemistry & Engineering ( IF 3.4 ) Pub Date : 2017-12-04 00:00:00 , DOI: 10.1039/c7re00120g Jatuporn Salaklang 1, 2, 3, 4, 5 , Veronique Maes 1, 2, 3, 4, 5 , Matthias Conradi 5, 6, 7, 8 , Rudy Dams 5, 6, 7, 8 , Tanja Junkers 1, 2, 3, 4, 5
Reaction Chemistry & Engineering ( IF 3.4 ) Pub Date : 2017-12-04 00:00:00 , DOI: 10.1039/c7re00120g Jatuporn Salaklang 1, 2, 3, 4, 5 , Veronique Maes 1, 2, 3, 4, 5 , Matthias Conradi 5, 6, 7, 8 , Rudy Dams 5, 6, 7, 8 , Tanja Junkers 1, 2, 3, 4, 5
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An efficient, safe and convenient laboratory scale continuous flow process for synthesis of (meth)acrylate monomers is described. (Meth)acryloyl chloride is reacted with n-octanol and other alcohols in the presence of triethyl amine in a tubular reactor, resulting in excellent conversions of alcohols to their corresponding esters within 0.5 to 5 minutes of reaction times. The formation of an unwanted side-compound, 3-chloropropionyl ester, is significantly minimized to less than 1% and the formed slurry can be processed without difficulty using an ultrasonication-assisted flow strategy. The synthesis is carried out over a period of 4 h without clogging or pressure build-up, with an operation throughput of 78.6 g h−1 of n-octyl acrylate monomer on laboratory scale, with 95% isolated yield. This procedure provides an efficient alternative synthetic route of functional (meth)acrylate esters, minimizes the side product and facilitates the handling of the formed slurry in the process. Synthesis of various (meth)acrylates is demonstrated, including biobased terpenyl acrylates. This development will play an important role for an on-demand production of (meth)acrylate monomers in fast, reliable and energy-efficient process.
中文翻译：
异质连续流过程中丙烯酸酯单体的直接合成†
描述了一种用于合成（甲基）丙烯酸酯单体的有效，安全和方便的实验室规模的连续流方法。（甲基）丙烯酰氯在三乙胺的存在下在管式反应器中与正辛醇和其他醇反应，导致醇在反应时间的0.5至5分钟内极佳地转化为其相应的酯。不需要的副化合物3-氯丙酸酯的形成被显着地减少到小于1％，并且可以使用超声辅助流动策略毫无困难地处理形成的浆液。合成在4小时内进行，没有堵塞或压力积聚，操作通量为n的78.6 gh -1实验室规模的丙烯酸正辛酯单体，分离产率为95％。该程序提供了功能性（甲基）丙烯酸酯的有效替代合成路线，使副产物减至最少，并有利于处理过程中形成的浆料。证明了各种（甲基）丙烯酸酯的合成，包括生物基丙烯酸萜烯基酯。这一发展将对按快速，可靠和节能的方法按需生产（甲基）丙烯酸酯单体起重要作用。
更新日期：2017-12-04
中文翻译：
异质连续流过程中丙烯酸酯单体的直接合成†
描述了一种用于合成（甲基）丙烯酸酯单体的有效，安全和方便的实验室规模的连续流方法。（甲基）丙烯酰氯在三乙胺的存在下在管式反应器中与正辛醇和其他醇反应，导致醇在反应时间的0.5至5分钟内极佳地转化为其相应的酯。不需要的副化合物3-氯丙酸酯的形成被显着地减少到小于1％，并且可以使用超声辅助流动策略毫无困难地处理形成的浆液。合成在4小时内进行，没有堵塞或压力积聚，操作通量为n的78.6 gh -1实验室规模的丙烯酸正辛酯单体，分离产率为95％。该程序提供了功能性（甲基）丙烯酸酯的有效替代合成路线，使副产物减至最少，并有利于处理过程中形成的浆料。证明了各种（甲基）丙烯酸酯的合成，包括生物基丙烯酸萜烯基酯。这一发展将对按快速，可靠和节能的方法按需生产（甲基）丙烯酸酯单体起重要作用。
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