Citation: LI Tian-Tian, WANG Chao-Yang, XING Li-Dan, LI Wei-Shan, PENG Bin, XU Meng-Qing, GU Feng-Long, HU She-Jun. Reaction Mechanism of 1,4-Dimethoxy Benzene as an Overcharge Protection Additive[J]. Acta Physico-Chimica Sinica, ;2012, 28(04): 818-822. doi: 10.3866/PKU.WHXB201201132 shu

Reaction Mechanism of 1,4-Dimethoxy Benzene as an Overcharge Protection Additive

LI Tian-Tian ¹ ,
WANG Chao-Yang ¹ ,
XING Li-Dan ¹ ,
LI Wei-Shan ^1,2,3, ,
PENG Bin ¹ ,
XU Meng-Qing ^1,2,3 ,
GU Feng-Long ^1,2,3 ,
HU She-Jun ^1,2,3

1.
1. School of Chemistry and Environment, South China Normal University, Guangzhou 510006, P. R. China;
2. Key Laboratory of Electrochemical Technology on Energy Storage and Power Generation of Guangdong Higher Education Institutes, South China Normal University, Guangzhou 510006, P. R. China;
3. Engineering Research Center of Materials and Technology for Electrochemical Energy Storage (Ministry of Education), South China Normal University, Guangzhou 510006, P. R. China

Received Date: 31 October 2011
Available Online: 13 January 2012
Fund Project: 国家自然科学基金-广东省人民政府自然科学联合基金(U1134002) (U1134002)广东省自然科学基金(10351063101000001)资助项目 (10351063101000001)

The reaction mechanism of 1,4-dimethoxybenzene (p-DMOB) as an overcharge protection additive for lithium ion batteries was determined by theoretical calculation of density functional theory (DFT) at the level of B3LYP/6-311+G(d,p) and MP2/6-311+G(d,p). It was found that p-DMOB is oxidized prior to the solvents, ethyl methyl carbonate, dimethyl carbonate, and ethylene carbonate, when the lithium ion battery is overcharged. The calculated oxidative potentials of p-DMOB by B3LYP and MP2 methods are well in agreement at 4.12 and 4.05 V (vs Li/Li^+·), respectively. The initial oxidation of p-DMOB involves a one-electron transfer resulting in a radical cation p-DMOB^+·. The corresponding energy variations were 701.24 and 728.27 kJ·mol^-1 from B3LYP and MP2 calculations, respectively. The p-DMOB^+· species then loses one proton forming a radical p-DMOB·through the breaking of a C―H bond on the benzene ring, with the corresponding energy variations of 1349.78 and 1810.99 kJ·mol^-1 for B3LYP and MP2, respectively. The p-DMOB·species is unstable and copolymerizes forming an insulated polymer with the corresponding energy variations of -553.37 and -1331.20 kJ·mol^-1 for B3LYP and MP2, respectively.
- Lithium ion battery,
- Overcharge protection additive,
- 1,4-Dimethoxy benzene,
- Reaction mechanism,
- Density functional theory
1. [1]
  (1) Ménard, L.; Fontès, G.; Astier, S. Energy Convers. Manage. 2010, 327.
2. [2]
  (2) Yu, Y.; Gu, L.; Zhu, C.; Aken, P. A.; Maier, J. J. Am. Chem. Soc. 2009, 131, 15984.
3. [3]
  (3) Yao, Z. D.;Wei,W.;Wang, J. L.; Yang, J.; Nuli, Y. N. Acta Phys. -Chim. Sin. 2011, 27, 1005. [姚真东, 魏巍, 王久林, 杨军, 努丽燕娜. 物理化学学报, 2011, 27, 1005.]
4. [4]
  (4) Fergus, J.W. J. Power Sources 2010, 195, 939.
5. [5]
  (5) Xu. J.; Yao,W. H.; Yao, Y.W.;Wang, Z. C.; Yang, Y. Acta Phys. -Chim. Sin. 2009, 25, 201. [许杰, 姚万浩, 姚宜稳, 王周成, 杨勇. 物理化学学报, 2009, 25, 201]
6. [6]
  (6) Xu, M. Q.; Zuo, X. X.; Li,W. S.; Zhou, H. J.; Liu, J. S.; Yuan, Z. Z. Acta Phys. -Chim. Sin. 2006, 22, 335. [许梦清, 左晓希, 李伟善, 周豪杰, 刘建生, 袁中直. 物理化学学报, 2006, 22, 335.]
7. [7]
  (7) Feng, J. K.; Ai, X. P.; Cao, Y. L.; Yang, H. X. Electrochem. Commun. 2007, 9, 25.
8. [8]
  (8) Chung, Y. S.; Yoo, S. H.; Kim, C. K. Ind. Eng. Chem. Res. 2009, 48, 4346.
9. [9]
  (9) Matsuta, S.; Kato, Y.; Ota, T.; Kurokawa, H.; Yoshimura, S.; Fujitani, S. J. Electrochem. Soc. 2001, 148, A7.
10. [10]
  (10) Moshkovich, M.; Cojocaru, M.; ttlieb, H. E.; Aurbach, D. J. Electroanal. Chem. 2001, 497, 84.
11. [11]
  (11) Xing, L. D.;Wang, C. Y.; Li,W. S.; Xu, M. Q.; Meng, X. L.; Zhao, S. F. J. Phys. Chem. B 2009, 113, 5181.
12. [12]
  (12) Xing, L. D.; Li,W. S.;Wang, C. Y.; Gu, F. L.; Xu, M. Q.; Tan, C. L.; Yi, J. J. Phys. Chem. B 2009, 113, 16596.
13. [13]
  (13) Balakrishnan, P. G.; Ramesh, R.; Kumar, T. P. J. Power Sources 2006, 155, 401.
14. [14]
  (14) Leising, R. A.; Palazzo, M. J.; Takeuchi, E. S.; Takeuchi, K. J. J. Power Sources 2001, 97, 681.
15. [15]
  (15) Li, S. L.; Ai, X. P.; Feng, J. K.; Cao, Y. L.; Yang, H. X. J. Power Sources 2008, 184, 553.
16. [16]
  (16) Xu, M. Q.; Xing, L. D.; Li,W. S.; Zuo, X. X.; Shu, D.; Li, G. L. J. Power Sources 2008, 184, 427.
17. [17]
  (17) Chen, J.; Buhrmester, C.; Dahn, J. R. Electrochem. Solid-State Lett. 2005, 8, A59.
18. [18]
  (18) Chen, Z. H.; Amine, K. Electrochim. Acta 2007, 53, 453.
19. [19]
  (19) Tag ugui, M.; Carré, B.;Willmann, P.; Lemordant, D. J. Power Sources 2007, 174, 1069.
20. [20]
  (20) Wang, R. L.; Dahn, J. R. J. Electrochem. Soc. 2006, 153, A1922.
21. [21]
  (21) Zheng, H. H.;Wang, X. J.; Li, B.; Qin, J. H. Chin. J. Power Sources 2006, 30, 511. [郑洪河, 王显军, 李苞, 秦建华. 电源技术, 2006, 30, 511]
22. [22]
  (22) Li, T. T.; Xing, L. D.; Li,W. S.; Peng, B.; Xu, M. Q.; Gu, F. L.; Hu, S. J. J. Phys. Chem. A 2011, 115, 4988.
23. [23]
  (23) Demartinez, M. C.; Marquez, O. P.; Marquez, J.; Hahn, F.; Beden, B.; Crouigneau, P.; Rakotondrainibe, A.; Lamy, C. Syth. Met. 1997, 88, 187.
24. [24]
  (24) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 03, revision B.05; Gaussian Inc.: Pittsburgh, PA, 2003.
25. [25]
  (25) Abbotto, A.; Streitwieser, A.; Schleyer, P. R. J. Am. Chem. Soc. 1997, 119, 11255.
26. [26]
  (26) Wang, Y.; Balbuena, P. B. J. Phys. Chem. A 2001, 105, 9972.
27. [27]
  (27) Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999.
28. [28]
  (28) Trasatti, S. Pure Appl. Chem. 1986, 58, 955.
1. [1]
  Aoyu Huang , Jun Xu , Yu Huang , Gui Chu , Mao Wang , Lili Wang , Yongqi Sun , Zhen Jiang , Xiaobo Zhu . Tailoring Electrode-Electrolyte Interfaces via a Simple Slurry Additive for Stable High-Voltage Lithium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100037-. doi: 10.3866/PKU.WHXB202408007
2. [2]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
3. [3]
  Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . 液相法制备硫化物固体电解质及其在全固态锂电池中的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2309019-. doi: 10.3866/PKU.WHXB202309019
4. [4]
  Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
5. [5]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
6. [6]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
7. [7]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
8. [8]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
9. [9]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
10. [10]
  Jiabo Huang , Quanxin Li , Zhongyan Cao , Li Dang , Shaofei Ni . Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations. University Chemistry, 2025, 40(3): 153-159. doi: 10.12461/PKU.DXHX202405172
11. [11]
  Yifeng Xu , Jiquan Liu , Bin Cui , Yan Li , Gang Xie , Ying Yang . “Xiao Li’s School Adventures: The Working Principles and Safety Risks of Lithium-ion Batteries”. University Chemistry, 2024, 39(9): 259-265. doi: 10.12461/PKU.DXHX202404009
12. [12]
  Siyu Zhang , Kunhong Gu , Bing'an Lu , Junwei Han , Jiang Zhou . Hydrometallurgical Processes on Recycling of Spent Lithium-lon Battery Cathode: Advances and Applications in Sustainable Technologies. Acta Physico-Chimica Sinica, 2024, 40(10): 2309028-. doi: 10.3866/PKU.WHXB202309028
13. [13]
  Qi Li , Pingan Li , Zetong Liu , Jiahui Zhang , Hao Zhang , Weilai Yu , Xianluo Hu . Fabricating Micro/Nanostructured Separators and Electrode Materials by Coaxial Electrospinning for Lithium-Ion Batteries: From Fundamentals to Applications. Acta Physico-Chimica Sinica, 2024, 40(10): 2311030-. doi: 10.3866/PKU.WHXB202311030
14. [14]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
15. [15]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
16. [16]
  Qian Huang , Zhaowei Li , Jianing Zhao , Ao Yu . Quantum Chemical Calculations Reveal the Details Below the Experimental Phenomenon. University Chemistry, 2024, 39(3): 395-400. doi: 10.3866/PKU.DXHX202309018
17. [17]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
18. [18]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
19. [19]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
20. [20]
  Meifeng Zhu , Jin Cheng , Kai Huang , Cheng Lian , Shouhong Xu , Honglai Liu . Classical Density Functional Theory for Understanding Electrochemical Interface. University Chemistry, 2025, 40(3): 148-152. doi: 10.12461/PKU.DXHX202405166

Get Citation

PDF

XML

Metrics

PDF Downloads(1160)
Abstract views(4412)
HTML views(117)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142