Synthesis of anolyte based on alkyl sulfonate anthraquinone and its application in flow batteries

doi:10.19799/j.cnki.2095-4239.2021.0025

Abstract

Abstract:

In this study, three types of alkyl sulfonate anthraquinones, (1-hydroxy-2-oxopropane sulfonic acid anthraquinone (1,2-AQPSH₂), 2,6-dioxopropane sulfonic acid anthraquinone (2,6-AQDPSH₂), and 1-hydroxy-2-oxopropane sulfonic acid anthraquinone (1,4-AQPSH₂), were synthesized using propane sultone from 1,2-dihydroxyanthraquinone, 2,6-dihydroxyanthraquinone and 1,4-dihydroxyanthracene, respectively. Solubility and the oxidation-reduction properties of these three anthraquinones in 1 mol/L NaCl aqueous solution under neutral conditions were studied in detail. 1,4-AQPSH₂ was selected and used as an anodolyte, 2,2,6,6-tetramethylpiperidinol (4-OH-TEMPO) was used as a catholyte, and Nafion 212 was used as an ion-exchange membrane to assemble a neutral water-based organic redox flow battery cell. Open circuit voltage of the flow battery was about 1.0 V; at a current density of 60 mA·cm^-2, the Coulombic efficiency, energy efficiency, and voltage efficiency of the cell were 97%, 68%, and 69%, respectively. At a current density of 60 mA·cm^-2, there was no substantial reduction in the discharge capacity of the battery after 75 charging and discharging cycles. These results demonstrate that 1,4-AQPSH₂ shows promise as an anolyte for neutral water-based organic redox flow batteries.

Key words: flow batteries, anthraquinone, propane sultone, solubility, anolyte

CLC Number:

TM 911.3

Teng LYU, Zixiang YE, Jing LI, Fuqiang CHU, Bencai LIN. Synthesis of anolyte based on alkyl sulfonate anthraquinone and its application in flow batteries[J]. Energy Storage Science and Technology, 2021, 10(4): 1317-1324.

Figures/Tables 6

Fig. 1

Fig. 2

Fig. 3

Fig. 4

Fig. 5

Fig. 6

References 26

1	LIU J, ZHANG J G, YANG Z G, et al. Materials science and materials chemistry for large scale electrochemical energy storage: From transportation to electrical grid[J]. Advanced Functional Materials, 2013, 23(8): 929-946.
2	LI L Y, KIM S, WANG W, et al. A stable vanadium redox-flow battery with high energy density for large-scale energy storage[J]. Advanced Energy Materials, 2011, 1(3): 394-400.
3	付甜甜. 美国伯克利实验室携手通用公司(GE)共同探索电动汽车储能新方案[J]. 电源技术, 2014, 38(2): 197-198.
4	刘素琴, 黄可龙, 刘又年, 等. 储能钒液流电池研发热点及前景[J]. 电池, 2005, 35(5): 356-359.
	LIU S Q, HUANG K L, LIU Y N, et al. The development and research progress in a energy storage unit—the vanadium redox flow battery[J]. Battery Bimonthly, 2005, 35(5): 356-359.
5	张华民, 王晓丽. 全钒液流电池技术最新研究进展[J]. 储能科学与技术, 2013, 2(3): 281-288.
	ZHANG H M, WANG X L. Recent progress on vanadium flow battery technologies[J]. Energy Storage Science and Technology, 2013, 2(3): 281-288.
6	XU Y, WEN Y H, CHENG J, et al. A study of tiron in aqueous solutions for redox flow battery application[J]. Electrochimica Acta, 2010, 55(3): 715-720.
7	LEUNG P, LI X H, PONCE DE LEÓN C, et al. Progress in redox flow batteries, remaining challenges and their applications in energy storage[J]. RSC Advances, 2012, 2(27): 10125-10156.
8	BEH E S, DE PORCELLINIS D, GRACIA R L, et al. A neutral pH aqueous organic-organometallic redox flow battery with extremely high capacity retention[J]. ACS Energy Letters, 2017, 2(3): 639-644.
9	WEDEGE K, BAE D, DRAŽEVIĆ E, et al. Unbiased, complete solar charging of a neutral flow battery by a single Si photocathode[J]. RSC Advances, 2018, 8(12): 6331-6340.
10	SEVOV C S, HICKEY D P, COOK M E, et al. Physical organic approach to persistent, cyclable, low-potential electrolytes for flow battery applications[J]. Journal of the American Chemical Society, 2017, 139(8): 2924-2927.
11	CHEN H N, CONG G T, LU Y C. Recent progress in organic redox flow batteries: Active materials, electrolytes and membranes[J]. Journal of Energy Chemistry, 2018, 27(5): 1304-1325.
12	ZHANG J, JIANG G P, XU P, et al. An all-aqueous redox flow battery with unprecedented energy density[J]. Energy & Environmental Science, 2018, 11(8): 2010-2015.
13	LIN K X, GÓMEZ-BOMBARELLI R, BEH E S, et al. A redox-flow battery with an alloxazine-based organic electrolyte[J]. Nature Energy, 2016, 1: 16102.
14	ODOM S. Preventing crossover in redox flow batteries through active material oligomerization[J]. ACS Central Science, 2018, 4(2): 140-141.
15	BRUSHETT F R, AZIZ M J, RODBY K E. On lifetime and cost of redox-active organics for aqueous flow batteries[J]. ACS Energy Letters, 2020, 5(3): 879-884.
16	DE LA CRUZ C, MOLINA A, PATIL N, et al. New insights into phenazine-based organic redox flow batteries by using high-throughput DFT modelling[J]. Sustainable Energy & Fuels, 2020, 4(11): 5513-5521.
17	HU B, LUO J, HU M W, et al. A pH-neutral, metal-free aqueous organic redox flow battery employing an ammonium anthraquinone anolyte[J]. Angewandte Chemie, 2019, 131(46): 16782-16789.
18	ZHOU W B, LIU W J, QIN M, et al. Fundamental properties of TEMPO-based catholytes for aqueous redox flow batteries: Effects of substituent groups and electrolytes on electrochemical properties, solubilities and battery performance[J]. RSC Advances, 2020, 10(37): 21839-21844.
19	HU Y D, YAN L M, YUE B H. Sulfonation mechanism of polysulfone in concentrated sulfuric acid for proton exchange membrane fuel cell applications[J]. ACS Omega, 2020, 5(22): 13219-13223.
20	WANG C X, YANG Z, WANG Y R, et al. High-performance alkaline organic redox flow batteries based on 2-hydroxy-3-carboxy-1, 4-naphthoquinone[J]. ACS Energy Letters, 2018, 3(10): 2404-2409.
21	ZHOU L J, ZHU J Y, LIN M J, et al. Tetra-alkylsulfonate functionalized poly(aryl ether) membranes with nanosized hydrophilic channels for efficient proton conduction[J]. Journal of Energy Chemistry, 2020, 40: 57-64.
22	ZHANG C, NIU Z, PENG S, et al. Phenothiazine-based organic catholyte for high-capacity and long-life aqueous redox flow batteries[J]. Advanced Materials (Deerfield Beach, Fla), 2019, 31(24): doi: 10. 1002/adma. 201901052.
23	AZIZ M A, HOSSAIN S I, SHANMUGAM S. Hierarchical oxygen rich-carbon nanorods: Efficient and durable electrode for all-vanadium redox flow batteries[J]. Journal of Power Sources, 2020, 445: doi: 10.1016/j.jpowsour. 2019. 227329.
24	KIM D K, YOON S J, KIM S. Transport phenomena associated with capacity loss of all-vanadium redox flow battery[J]. International Journal of Heat and Mass Transfer, 2020, 148: doi: 10. 1016/j.ijheatmasstransfer. 2019. 119040.
25	YANG B, MURALI A, NIRMALCHANDAR A, et al. A durable, inexpensive and scalable redox flow battery based on iron sulfate and anthraquinone disulfonic acid[J]. Journal of the Electrochemical Society, 2020, 167(6): doi: 10. 1149/1945-7111/ab84f8.
26	KWABI D G, LIN K X, JI Y L, et al. Alkaline quinone flow battery with long lifetime at pH 12[J]. Joule, 2018, 2(9): 1894-1906.

[1]	Zhenyu WANG, Zixiao GUO, Xinzhuang FAN, Tianshou ZHAO. Comparative study between serpentine and interdigitated flow fields for vanadium redox flow batteries [J]. Energy Storage Science and Technology, 2022, 11(4): 1121-1130.
[2]	Kang PENG, Junmin LIU, Gonggen TANG, Zhengjin YANG, Tongwen XU. Status and prospects of organic eletroactive species for aqueous organic redox flow batteries [J]. Energy Storage Science and Technology, 2022, 11(4): 1246-1263.
[3]	Ang LI, Xiaomeng LI, Lin YANG, Han WANG, Junfan XIANG, Yuhan LIU. Compression force calculation of redox flow battery [J]. Energy Storage Science and Technology, 2022, 11(2): 609-614.
[4]	Qiang LI, Junnan WANG, Hong SUN. Graphite felt electrode modified with MWCNTs-COOH-NS for vanadium flow battery [J]. Energy Storage Science and Technology, 2021, 10(6): 2097-2105.
[5]	YANG Lin, WANG Han, LI Xiaomeng, ZHAO Zhao, ZUO Yuanjie, LIU Yujia, LIU Yun. Introduction and engineering case analysis of 250 kW/1.5 MW·h iron-chromium redox flow batteries energy storage demonstrationpower station [J]. Energy Storage Science and Technology, 2020, 9(3): 751-756.
[6]	ZHANG Tao, WANG Wenqiang, WANG Gengchao. Matching the positive and negative electrode based on hierarchical porous carbon supporting π-conjugated polymers composites for asymmetric organic supercapacitor [J]. Energy Storage Science and Technology, 2016, 5(4): 469-477.
[7]	CAO Liuyue, SKYLLAS-KAZACOS Maria, WANG Dawei. Electrode modification and electrocatalysis for redox flow battery (RFB) applications [J]. Energy Storage Science and Technology, 2015, 4(5): 433-457.