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Non-Isocyanate and Catalyst-Free Synthesis of a Recyclable Polythiourethane with Cyclic Structure
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2020-03-31 , DOI: 10.1021/acssuschemeng.0c00435
Shuang Wu 1 , Ming Luo 1 , Donald J. Darensbourg 2 , Dandan Zeng 1 , Yuhua Yao 1 , Xiaobing Zuo 1 , Xin Hu 1 , Dawei Tan 1
Affiliation  

Polythiourethane is a promising heteroatom-containing polymeric material possessing outstanding properties such as high refractive index, biocompatibility, and good coordinating ability to heavy metal ions. However, examples of versatile polythiourethanes are relatively scarce as a result of the limited methods for their synthesis. Herein, we report an efficient non-isocyanate and catalyst-free strategy to synthesize polythiourethane from the highly alternating and regioselective copolymerization of carbonyl sulfide (COS) and 2-methyl aziridine. The copolymerization proceeded efficiently at room temperature and afforded copolymer in 95% selectivity and molecular weight of 15.2 kg/mol in 2 h. Furthermore, the reaction was efficient even at 1 atm of COS at room temperature. Remarkably, the copolymer possessed a cyclic topology, and it could be completely recycled into cyclic thiourethane by simply heating the bulk materials at 200 °C for 1.5 h. The copolymer was applied as a heavy metal absorption and recovery agent; lead ions in aqueous solution were adsorbed by the copolymer, and both were eventually separated and recovered in the form of lead compounds and cyclic thiourethanes, respectively. Hence, this study provides a sustainable and atom-economical method for synthesizing polythiourethane and a green method to recover hazardous metals with minimal waste and VOC emission.

中文翻译:

非异氰酸酯和无催化剂合成具有环状结构的可回收聚硫氨基甲酸酯

聚硫氨酯是一种有前途的含杂原子的聚合物材料,它具有出色的性能,例如高折射率,生物相容性以及与重金属离子的良好配位能力。然而,由于有限的合成方法,多功能聚硫氨基甲酸酯的例子相对较少。在这里,我们报告了一种有效的非异氰酸酯和无催化剂的策略,可以从羰基硫(COS)和2-甲基氮丙啶的高度交替和区域选择性共聚反应中合成聚硫氨基甲酸酯。共聚在室温下有效地进行,并在2小时内以95%的选择性和15.2kg / mol的分子量提供共聚物。此外,即使在室温下在1atm的COS下,该反应也是有效的。值得注意的是,该共聚物具有环状拓扑,只需将散装物料在200°C下加热1.5小时,就可以将其完全回收成环状硫代氨基甲酸酯。将该共聚物用作重金属吸收和回收剂;水溶液中的铅离子被共聚物吸附,最终两者分别以铅化合物和环状硫代氨基甲酸酯的形式分离和回收。因此,本研究提供了一种可持续的,原子经济的合成聚硫代氨基甲酸酯的方法,以及一种以最少的废物和VOC排放来回收有害金属的绿色方法。最终分别以铅化合物和环状硫代氨基甲酸酯的形式分离和回收。因此,本研究提供了一种可持续的,原子经济的合成聚硫代氨基甲酸酯的方法,以及一种以最少的废物和VOC排放来回收有害金属的绿色方法。最终分别以铅化合物和环状硫代氨基甲酸酯的形式分离和回收。因此,本研究提供了一种可持续的,原子经济的合成聚硫代氨基甲酸酯的方法,以及一种以最少的废物和VOC排放来回收有害金属的绿色方法。
更新日期:2020-03-31
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