Calbrix Elliot, de Caro Pascale, Thiebaud-Roux Sophie, Cecutti Christine, Vedrenne Emeline
Laboratoire de Chimie Agro-Industrielle (LCA), Université de Toulouse, INRAE, 4 allée Emile Monso, 31030 Toulouse, France.
Molecules. 2025 Jan 7;30(2):216. doi: 10.3390/molecules30020216.
In organic synthesis, the solvent is the chemical compound that represents the largest proportion of the process. However, conventional solvents are often toxic and dangerous for the environment, and an interesting alternative is to replace them by water. In this context, catalyst surfactants allow both organic reagents in water to be solubilized and organic reactions to be catalyzed. This article describes the synthesis of new biobased organocatalytic surfactants soluble in water, composed of a hydrocarbon chain grafted onto an imidazolidinone moiety. The imidazolidinone moiety acts as catalyst, but also as the polar head of the surfactant, while the fatty chain constitutes the hydrophobic tail. The five steps of the synthesis were optimized, respecting the principles of green chemistry, and two organocatalytic surfactants were obtained with a good selectivity. Surface properties in an aqueous medium were then evaluated with the use of tensiometric analysis. Their molecular organization in vesicles was characterized by Dynamic Light Scattering. The presence of vesicles allows reactions to be carried out in an organized aqueous medium. Model catalytic reactions performed in aqueous medium validated the feasibility of replacing conventional hazardous organic solvents. The newly synthesized biobased surfactants showed satisfactory catalytic activity and allowed the expected products to be obtained with good enantioselectivity.
在有机合成中，溶剂是该过程中占比最大的化合物。然而，传统溶剂通常有毒且对环境有害，一个有趣的替代方法是用水来取代它们。在这种背景下，催化剂表面活性剂既能使水中的有机试剂溶解，又能催化有机反应。本文描述了一种新型的可溶于水的生物基有机催化表面活性剂的合成，该表面活性剂由接枝在咪唑啉酮部分上的烃链组成。咪唑啉酮部分既作为催化剂，又作为表面活性剂的极性头，而脂肪链构成疏水尾。合成的五个步骤按照绿色化学原则进行了优化，得到了两种具有良好选择性的有机催化表面活性剂。然后使用张力分析评估了其在水介质中的表面性质。通过动态光散射对它们在囊泡中的分子组织进行了表征。囊泡的存在使得反应能够在有序的水介质中进行。在水介质中进行的模型催化反应验证了取代传统有害有机溶剂的可行性。新合成的生物基表面活性剂表现出令人满意的催化活性，并能以良好的对映选择性得到预期产物。
