Ruthenium-catalyzed dimerization of vanillin for the formation of a biobased epoxy thermoset resin†

Flavia Ferrara, Iuliana Ribca, Namratha Prabhu, Josselin Mante, Maureen Gumbo, Andreas Ekebergh, Mats Johansson and Nina Kann
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引用次数: 0

Abstract

Vanillin is one of few lignin platform chemicals that are currently available on industrial scale. Seeking to find biobased alternatives to the reprotoxic compound bisphenol A (BPA), we have successfully dimerized three different monomeric vanillin derivatives in a ruthenium-catalyzed Tischenko reaction. The resulting esters were characterized by NMR, FTIR, HRMS, and single crystal X-ray diffraction. The thermal behaviour of one of these derivatives, the epoxy divanillin ester EDVE, was studied further by DSC and TGA. EDVE was subsequently applied towards the preparation of an epoxy thermoset resin via curing with Jeffamine D-400. The thermoset formulation was thermally cured, monitoring the curing with DSC and FTIR. The final thermoset was then characterized with respect to physical and mechanical properties with DSC, TGA, and DMA. This catalytic approach provides a new strategy to access vanillin-based epoxides that could potentially replace bisphenol A.

钌催化香兰素二聚形成生物基环氧热固性树脂†
香兰素是目前工业规模上可用的少数木质素平台化学品之一。为了寻找生殖毒性化合物双酚A (BPA)的生物基替代品,我们在钌催化的Tischenko反应中成功地将三种不同的单体香兰素衍生物二聚体化。通过NMR、FTIR、HRMS和单晶x射线衍射对所得酯类进行了表征。通过DSC和TGA进一步研究了其中一种衍生物环氧双苯胺酯EDVE的热行为。EDVE随后应用于与Jeffamine D-400固化制备环氧热固性树脂。对热固性配方进行热固化,用DSC和FTIR监测固化过程。最后的热固性,然后表征与物理和机械性能与DSC, TGA和DMA。这种催化方法为获得可能取代双酚a的香草素基环氧化物提供了一种新的策略。
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