Developing novel monomers used for aromatic polyamide membranes is one of the promising modifications to tailor the membranes more efficient. Acyl chloride-based compound as the organic phase reactive monomer is vital to the fabrication of membranes. This study focuses on designing and synthesizing a novel acyl chloride monomer 5-(1-pyrrolidinyl)-1,3-benzenedicarbonyl dichloride (PIPC) based on the purpose of improving membrane permeability and anti-fouling, and preliminarily verify its feasibility for the synthesis of aromatic polyamide membranes. PIPC monomer with a rigid pyrrolidinyl group (–NCH) was synthesized from three steps of N-alkylation, ester hydrolysis and acylation reaction successively. IR and HNMR spectra were employed to demonstrate the successful synthesis of PIPC. The application of PIPC in the membrane field was also implemented via using PIPC alone as the organic phase reactive monomer, the first/second organic phase reactive monomer, and PIPC and trimesoyl chloride (TMC) together act as the organic phase reactive monomer to react with m-phenylenediamine (MPD) by interfacial polymerization (IP). The MPD-PIPC-TMC membrane prepared by PIPC as the first organic phase reactive monomer exhibited the highest water flux (27.89 ​L ​m ​h), with the increase of 36.8% than the MPD-TMC membrane (20.38 ​L ​m ​h), while maintaining similar salt rejection. The PIPC with a rigid pyrrolidinyl group was demonstrated to be a promising organic phase monomer for further synthesizing high permeability aromatic polyamide membrane, which showed great application prospects in the field of membrane industry.

中文翻译：

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新型单体5-(1-吡咯烷基)-1,3-苯二甲酰二氯的合成及其在膜中的应用

开发用于芳香族聚酰胺膜的新型单体是一种有希望的改进方法，可以更有效地定制膜。酰氯基化合物作为有机相反应单体对于膜的制造至关重要。本研究以提高膜渗透性和抗污染为目的，设计合成了一种新型酰氯单体5-(1-吡咯烷基)-1,3-苯二甲酰二氯(PIPC)，并初步验证了其合成的可行性。芳香族聚酰胺膜。依次经过N-烷基化、酯水解和酰化反应三步合成了带有刚性吡咯烷基(-NCH)的PIPC单体。红外光谱和核磁共振氢谱证明了PIPC的成功合成。 PIPC在膜领域的应用也是通过单独使用PIPC作为有机相反应单体、第一/第二有机相反应单体以及PIPC和均苯三甲酰氯(TMC)共同作为有机相反应单体进行反应来实现的。通过界面聚合 (IP) 制备间苯二胺 (MPD)。以PIPC作为第一有机相反应单体制备的MPD-PIPC-TMC膜表现出最高的水通量（27.89​L ​m ​h），比MPD-TMC膜（20.38​L ​m h）提高了36.8％ ​h），同时保持类似的脱盐率。具有刚性吡咯烷基的PIPC被证明是一种有前途的有机相单体，可用于进一步合成高渗透性芳香族聚酰胺膜，在膜工业领域显示出巨大的应用前景。