Economic Sulfur Conversion to Functional Polythioamides through Catalyst-Free Multicomponent Polymerizations of Sulfur, Acids, and Amines

被引:167
作者
Cao, Wenxia [1 ]
Dai, Fengying [2 ]
Hu, Rongrong [1 ]
Tang, Ben Zhong [1 ,3 ]
机构
[1] South China Univ Technol, Ctr Aggregat Induced Emiss, State Key Lab Luminescent Mat & Devices, Guangzhou 510640, Peoples R China
[2] South China Univ Technol, Analyt & Testing Ctr, Guangzhou 510640, Peoples R China
[3] Hong Kong Univ Sci & Technol, Chinese Natl Engn Res Ctr Tissue Restorat & Recon, Dept Chem, Hong Kong Branch,Kowloon, Clear Water Bay, Hong Kong, Peoples R China
基金
美国国家科学基金会;
关键词
ELEMENTAL SULFUR; DIAMINES; GOLD; DIALDEHYDES; RECOVERY; METALS; WASTE;
D O I
10.1021/jacs.9b11066
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Sulfur utilization is a global concern because of its abundant nature sources and the safety or environmental problems caused by its burning or oxidation during storage, while sulfur-containing polymers are popular materials in virtue of their fascinating properties such as metal coordination ability, high refractive indices, and semiconducting property. The synthesis of sulfur-containing polymers is challenging, especially directly from elemental sulfur. Herein, catalyst-free and scalable multicomponent polymerizations (MCPs) of all commercially available elemental sulfur, dicarboxylic acids, and diamines were reported to facilely construct 12 polythioamides with diverse and well-defined structures, high molecular weights (M-w's up to 86 200 g/mol), and excellent yields (up to 99%) from elemental sulfur. Besides commonly used aliphatic diamines, aromatic diamine monomers are also applicable to these multicomponent polymerizations, affording polythioamides with unique rigid structures and improved functionality as compared to those of the previously reported polythioamides. These polythioamides can be applied in gold recovery, which could extract a trace amount of Au3+ from practical acidic leaching solution of discarded electronic waste selectively, rapidly (1 min), sensitively (10 ppb), and efficiently (>99.99%) with high extraction capacity up to 0.60 g.Au3+/g to directly afford high-purity elemental gold after pyrolysis. The MCPs could make use of both abundantly existing sulfur waste and trace amounts of precious gold residue in electronic wastes, demonstrating their great potential in resource utilization.
引用
收藏
页码:978 / 986
页数:9
相关论文
共 53 条
[1]   Sulfur and Its Role In Modern Materials Science [J].
Boyd, Darryl A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (50) :15486-15502
[2]  
Chung WJ, 2013, NAT CHEM, V5, P518, DOI [10.1038/NCHEM.1624, 10.1038/nchem.1624]
[3]   Metallurgical recovery of metals from electronic waste: A review [J].
Cui, Jirang ;
Zhang, Lifeng .
JOURNAL OF HAZARDOUS MATERIALS, 2008, 158 (2-3) :228-256
[4]   POLYTHIOAMIDE SYNTHESIS THROUGH CHEMICAL MODIFICATION OF POLYAMIDES [J].
DELETRE, M ;
LEVESQUE, G .
MACROMOLECULES, 1990, 23 (22) :4876-4878
[5]   POLYTHIOAMIDE AND POLY(1,3,4-THIADIAZOLE) SYNTHESIS FROM DIMETHYL TETRATHIOTEREPHTHALATE [J].
DELFANNE, I ;
LEVESQUE, G .
MACROMOLECULES, 1989, 22 (06) :2589-2592
[6]   A facile synthetic route to poly(p-phenylene terephthalamide) with dual functional groups [J].
Du, Shuming ;
Wang, Wenbin ;
Yan, Yan ;
Zhang, Jie ;
Tian, Ming ;
Zhang, Liqun ;
Wan, Xinhua .
CHEMICAL COMMUNICATIONS, 2014, 50 (69) :9929-9931
[7]   Carboxylates as sources of carbon nucleophiles and electrophiles: comparison of decarboxylative and decarbonylative pathways [J].
Dzik, Wojciech I. ;
Lange, Paul P. ;
Goossen, Lukas J. .
CHEMICAL SCIENCE, 2012, 3 (09) :2671-2678
[8]   ALIPHATIC POLYTHIOAMIDES .1. SYNTHESIS OF BIS(DITHIOESTERS) [J].
GRESSIER, JC ;
LEVESQUE, G .
EUROPEAN POLYMER JOURNAL, 1980, 16 (11) :1093-1100
[9]   Polymerizations with elemental sulfur: A novel route to high sulfur content polymers for sustainability, energy and defense [J].
Griebel, Jared J. ;
Glass, Richard S. ;
Char, Kookheon ;
Pyun, Jeffrey .
PROGRESS IN POLYMER SCIENCE, 2016, 58 :90-125
[10]   Decarboxylative Thioamidation of Arylacetic and Cinnamic Acids: A New Approach to Thioamides [J].
Guntreddi, Tirumaleswararao ;
Vanjari, Rajeshwer ;
Singh, Krishna Nand .
ORGANIC LETTERS, 2014, 16 (14) :3624-3627