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Greener and scalable synthesis of N-methyl imines using a sustainable functional polymer
Green Materials ( IF 1.9 ) Pub Date : 2022-10-13 , DOI: 10.1680/jgrma.22.00068
Peyman Mihankhah 1 , Nader Ghaffari Khaligh 1
Affiliation  

N-Methyl imines, as simple Schiff bases, could be prepared using a more sustainable and greener system, including a 33 wt.% solution of methylamine in absolute ethanol, and poly(N-vinylimidazole) (PVIm) at room temperature within 45–60 min. PVIm is a biocompatible, biodegradable and water-soluble synthetic solid functional polymer. It was indicated that PVIm can act as a reagent with multiple tasks in this reaction, including (a) reducing activation energy and stabilizing the transition states through hydrogen bond acceptor sites and low acidity of C(2)–H and (b) dehydrating activity through trapping of the released water molecules as the association phase. Inexperienced chemists can handle it easily because it is solid and less toxic than conventional catalysts – that is, piperidine, pyridine or metal- or halogen-containing salts. Additionally, ethanol and PVIm could be recycled and reused in subsequent runs without any further purification. The regenerated PVIm demonstrated stable activity after several recycle runs. No changes were detected in its chemical structure, as confirmed by Fourier transform infrared and nuclear magnetic resonance spectrum analyses.

中文翻译:

使用可持续功能聚合物更环保、可扩展地合成 N-甲基亚胺

N-甲基亚胺作为简单的希夫碱,可以使用更可持续和更环保的系统来制备,包括 33 wt.% 的甲胺无水乙醇溶液和聚(N-乙烯基咪唑)(PVIm),在室温下45 – 60 分钟 PVIm 是一种生物相容性、可生物降解且水溶性的合成固体功能聚合物。结果表明,PVIm 可以作为该反应中的多种任务的试剂,包括(a)通过氢键受体位点降低活化能并稳定过渡态以及 C(2)–H 的低酸性和(b))通过捕获释放的水分子作为缔合相进行脱水活性。没有经验的化学家可以轻松处理它,因为它是固体,并且比传统催化剂(即哌啶、吡啶或含金属或卤素的盐)毒性更低。此外,乙醇和 PVIm 可以在后续运行中回收并重复使用,无需任何进一步纯化。再生的 PVIm 在多次循环运行后表现出稳定的活性。经傅里叶变换红外和核磁共振谱分析证实,其化学结构未检测到任何变化。
更新日期:2022-10-13
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