Citation: Rupa Rani Dey, Siddhartha Sankar Dhar. Ammonium persulphate promoted synthesis of polyethylene glycol entrapped potassium tribromide and its application in acylation and bromination of some selective organic compounds[J]. Chinese Chemical Letters, ;2013, 24(10): 866-868. shu

Ammonium persulphate promoted synthesis of polyethylene glycol entrapped potassium tribromide and its application in acylation and bromination of some selective organic compounds

Rupa Rani Dey ,
Siddhartha Sankar Dhar ^,

1.
Department of Chemistry, National Institute of Technology, Silchar, Assam 788010, India

Corresponding author: Siddhartha Sankar Dhar,
Received Date: 24 April 2013
Available Online: 22 May 2013
Fund Project:

In this study, a new method of synthesis of polyethylene glycol supported potassium tribromide (PEG KBr₃) and its application in acylation and bromination reactions are reported. Ammonium persulphate oxidizes KBr to the corresponding tribromide which is entrapped by polyethylene glycol leading to stable PEG KBr₃. The reagent is proved to be highly efficient for the acylation of variety of alcohols and bromination of activated aromatic substrates. Themethod is a mild, one pot reaction and involves no use of toxic reagents.
- Potassium bromide,
- Polyethylene glycol (PEG),
- Ammonium per sulphate,
- Acylation,
- Bromination
1. [1]
  [1] P.T. Anastas, J.C. Warner, Green Chemistry: Theory and practice, Oxford University Press, New York, 1998.
2. [2]
  [2] S. Wenda, S. Illner, A. Mell, et al., Industrial biotechnology—the future of green chemistry, Green Chem. 13 (2011) 3007-3047.
3. [3]
  [3] C. Chiappe, E. Leandri, D. Pieraccini, Highly efficient bromination of aromatic compounds using 3-methylimidazolium tribromides as reagent/solvent, J. Chem. Soc. Chem. Commun. 45 (2004) 2536-2537.
4. [4]
  [4] A.D. Jordan, C. Luo, A.B. Reitz, Efficient conversion of substituted aryl thioureas to 2-aminobenzothiazoles using benzyltrimethyl ammonium tribromides, J. Org. Chem. 68 (2003) 8693-8696.
5. [5]
  [5] K. Ma, S. Li, R.G.Weiss, Stereoselective bromination reactions using tridecylmethylphosphonium tribromide in a "Stacked" reactor, Org. Lett. 10 (2008) 4155-4158.
6. [6]
  [6] A.R. Hajipour, S.A. Pourmousavi, A.E. Ruoho, Benzyltriphenylphosphonium tribromide: a mild, regenerable and efficient reagent for the deprotection of dithioacetals, J. Sulfur Chem. 25 (2004) 401-405.
7. [7]
  [7] V. Kavala, S. Naik, B.K. Patel, A new recyclable ditribromide reagent for efficient bromination under solvent free condition, J. Org. Chem. 70 (2005) 4267-4271.
8. [8]
  [8] M. Dey, S.S. Dhar, M. Kalita, Novel methods of synthesis of quaternary ammonium tribromides and investigation of catalytic role of benzyltrimethyl ammonium tribromide in oxidation alcohols to carbonyl compounds, Synth. Commun. 43 (2013) 1734-1742.
9. [9]
  [9] M. Dey, S.S. Dhar, Synthesis of quaternary tribromides: a novel green approach, Green Chem. Lett. Rev. 5 (2012) 639-642.
10. [10]
  [10] R. Borah, A.J. Thakur, Green synthesis of tetraalkylammonium tribromide using cerium (IV) ammonium nitrate (CAN) as oxidant, Synth. Commun. 37 (2007) 933-939.
11. [11]
  [11] U. Bora, M.K. Chaudhuri, S.S. Dhar, et al., Peroxometal-mediated environmentally favourable route to brominating agents and protocol for the bromination of organics, Pure Appl. Chem. 73 (2001) 93-102.
12. [12]
  [12] M. K. Chaudhuri, U. Bora, S.S. Dhar, et al., Process of preparing quaternary ammonium tribromides, US Patent 7005548 (2006).
13. [13]
  [13] M. Dey, K. Deb, S.S. Dhar, VO(acac)₂ catalysed condensation of o-phenylenediamine with aromatic carboxylic acids/aldehydes under microwave radiation affording benzimidazoles, Chin. Chem. Lett. 22 (2011) 296-299.
14. [14]
  [14] M.A. Zolfigol, G. Chehardoli, S. Salehzadeh, et al., {[K 18-Crown-6]Br₃}_n: a unique tribromide-type and columnar nanotube-like structure for the oxidative coupling of thiols and bromination of some aromatic compounds, Tetrahedron Lett. 48 (2007) 7969-7973.
15. [15]
  [15] M. Hossein, K. Zahra, Synthesis and application of poly (diallyldimethylammonium tribromide) as a novel polymeric brominating agent, Chin. J. Chem. 28 (2010) 2221-2225.
16. [16]
  [16] K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, 5th ed., John Wiley & Sons Inc., New York, 1997p. 169.
17. [17]
  [17] T. Ozeki, H. Yuasa, Y. Kanaya, Application of the solid dispersion method to the controlled release of medicine. IX. Difference in the release of flurbiprofen from solid dispersions with poly(ethylene oxide) and hydroxypropylcellulose and the interaction between medicine and polymers, Int. J. Pharm. 155 (1997) 209-217.
18. [18]
  [18] K. Shameli, M.B. Ahmad, S.D. Jazayeri, Synthesis and characterization of polyethylene glycol mediated silver nanoparticles by the green method, Int. J. Mol. Sci. 13 (2012) 6639-6650.
19. [19]
  [19] E. Kang, J. Robinson, K. Park, et al., Paclitaxel distribution in poly(ethylene glycol)/poly(lactide-co-glycolic acid) blends and its release visualized by coherent anti-Stokes Raman scattering microscopy, J. Control. Release 122 (2007) 261-268.
20. [20]
  [20] V. Meisalo, O. Inkinen, An X-ray diffraction analysis of potassium bromide, Acta Crystallogr. 22 (1967) 58-65.
21. [21]
  [21] H.B. Watson, The reaction of bromine with aliphatic acids. Catalytic effect of acyl halides, J. Chem. Soc. Trans. 127 (1925) 2067-2082.
22. [22]
  [22] J. Buckinghum, S.M. Donaghy, Dictionary of Organic Compounds, 6th ed., Chapman & Hall, London, 1982.
1. [1]
  Haiying Wei , Daqing Yang , Mingtao Run , Guoyan Huo . Examination and Analysis on Rationality of Experimental Design: Based on Reaction of Potassium Permanganate with Potassium Bormide. University Chemistry, 2024, 39(10): 283-288. doi: 10.12461/PKU.DXHX202404068
2. [2]
  Leichen Wang , Anqing Mei , Na Li , Xiaohong Ruan , Xu Sun , Yu Cai , Jinjun Shao , Xiaochen Dong . Aza-BODIPY dye with unexpected bromination and high singlet oxygen quantum yield for photoacoustic imaging-guided synergetic photodynamic/photothermal therapy. Chinese Chemical Letters, 2024, 35(6): 108974-. doi: 10.1016/j.cclet.2023.108974
3. [3]
  Aonan Wang , Jingwen Dai , Yiming Guo , Fanghua Ning , Xiaoyu Liu , Sidra Subhan , Jiaqian Qin , Shigang Lu , Jin Yi . Imidazolium bromide based dual-functional redox mediator for the construction of dendrite-free Li-CO₂ batteries. Chinese Chemical Letters, 2025, 36(7): 110186-. doi: 10.1016/j.cclet.2024.110186
4. [4]
  Zhanheng Yan , Weiqing Su , Weiwei Xu , Qianhui Mao , Lisha Xue , Huanxin Li , Wuhua Liu , Xiu Li , Qiuhui Zhang . Carbon-based quantum dots/nanodots materials for potassium ion storage. Chinese Chemical Letters, 2025, 36(4): 110217-. doi: 10.1016/j.cclet.2024.110217
5. [5]
  Jun-Ming Cao , Kai-Yang Zhang , Jia-Lin Yang , Zhen-Yi Gu , Xing-Long Wu . Differential bonding behaviors of sodium/potassium-ion storage in sawdust waste carbon derivatives. Chinese Chemical Letters, 2024, 35(4): 109304-. doi: 10.1016/j.cclet.2023.109304
6. [6]
  Yingfen Li , Zhiqi Wang , Yunhai Zhao , Dajun Luo , Xueliang Zhang , Jun Zhao , Zhenghua Su , Shuo Chen , Guangxing Liang . Potassium doping for grain boundary passivation and defect suppression enables highly-efficient kesterite solar cells. Chinese Chemical Letters, 2024, 35(11): 109468-. doi: 10.1016/j.cclet.2023.109468
7. [7]
  Yang Li , Xiaoxu Liu , Tianyi Ji , Man Zhang , Xueru Yan , Mengjie Yao , Dawei Sheng , Shaodong Li , Peipei Ren , Zexiang Shen . Potassium ion doped manganese oxide nanoscrolls enhanced the performance of aqueous zinc-ion batteries. Chinese Chemical Letters, 2025, 36(1): 109551-. doi: 10.1016/j.cclet.2024.109551
8. [8]
  Cailing Wu , Shaojie Wu , Qifei Huang , Kai Sun , Xianqiang Huang , Jianji Wang , Bing Yu . Potassium-modified carbon nitride photocatalyzed-aminoacylation of N-sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110250-. doi: 10.1016/j.cclet.2024.110250
9. [9]
  Wenjing Xiong , Yulin Xu , Fangzhou Zhao , Baokai Xia , Hongqiang Wang , Wei Liu , Sheng Chen , Yongzhi Zhang . Graphene architecture interpenetrated with mesoporous carbon nanosheets promotes fast and stable potassium storage. Chinese Chemical Letters, 2025, 36(4): 109738-. doi: 10.1016/j.cclet.2024.109738
10. [10]
  Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
11. [11]
  Quanxing Mao , Zhengliang Wang , Zhinan Hu , Ziqi Yang , Hui Li , Yali Yao , Zijun Yong , Tianyi Ma . Facial detection of formaldehyde by using acidichromic carbon dots and the reaction between formaldehyde and ammonium chloride. Chinese Chemical Letters, 2025, 36(7): 110499-. doi: 10.1016/j.cclet.2024.110499
12. [12]
  Tong Su , Yue Wang , Qizhen Zhu , Mengyao Xu , Ning Qiao , Bin Xu . Multiple conductive network for KTi₂(PO₄)₃ anode based on MXene as a binder for high-performance potassium storage. Chinese Chemical Letters, 2024, 35(8): 109191-. doi: 10.1016/j.cclet.2023.109191
13. [13]
  Zhong-Hui Sun , Yu-Qi Zhang , Zhen-Yi Gu , Dong-Yang Qu , Hong-Yu Guan , Xing-Long Wu . CoPSe nanoparticles confined in nitrogen-doped dual carbon network towards high-performance lithium/potassium ion batteries. Chinese Chemical Letters, 2025, 36(1): 109590-. doi: 10.1016/j.cclet.2024.109590
14. [14]
  Shimei Wu , Yining Li , Lantao Chen , Yufei Zhang , Lingxing Zeng , Haosen Fan . Hexapod cobalt phosphosulfide nanorods encapsulating into multiple hetero-atom doped carbon frameworks for advanced sodium/potassium ion battery anodes. Chinese Chemical Letters, 2025, 36(4): 109796-. doi: 10.1016/j.cclet.2024.109796
15. [15]
  Xiaoxiao Huang , Zhi-Long He , Yangpeng Chen , Lei Li , Zhenyu Yang , Chunyang Zhai , Mingshan Zhu . Novel P-doping-tuned Pd nanoflowers/S,N-GQDs photo-electrocatalyst for high-efficient ethylene glycol oxidation. Chinese Chemical Letters, 2024, 35(6): 109271-. doi: 10.1016/j.cclet.2023.109271
16. [16]
  Junying LI , Xinyan CHEN , Xihui DIAO , Muhammad Yaseen , Chao CHEN , Hao WANG , Chuansong QI , Wei LI . Chiral fluorescent sensor Tb³⁺@Cd-CP based on camphoric acid for the enantioselective recognition of R- and S-propylene glycol. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2497-2504. doi: 10.11862/CJIC.20240084
17. [17]
  Wen Xiao , Fazhan Wang , Yangzhuo Gu , Xi He , Na Fan , Qian Zheng , Shugang Qin , Zhongshan He , Yuquan Wei , Xiangrong Song . PEG400-mediated nanocarriers improve the delivery and therapeutic efficiency of mRNA tumor vaccines. Chinese Chemical Letters, 2024, 35(5): 108755-. doi: 10.1016/j.cclet.2023.108755
18. [18]
  Qiang Cao , Xue-Feng Cheng , Jia Wang , Chang Zhou , Liu-Jun Yang , Guan Wang , Dong-Yun Chen , Jing-Hui He , Jian-Mei Lu . Graphene from microwave-initiated upcycling of waste polyethylene for electrocatalytic reduction of chloramphenicol. Chinese Chemical Letters, 2024, 35(4): 108759-. doi: 10.1016/j.cclet.2023.108759
19. [19]
  Min Chen , Boyu Peng , Xuyun Guo , Ye Zhu , Hanying Li . Polyethylene interfacial dielectric layer for organic semiconductor single crystal based field-effect transistors. Chinese Chemical Letters, 2024, 35(4): 109051-. doi: 10.1016/j.cclet.2023.109051
20. [20]
  Xiaxia Xing , Xiaoyu Chen , Zhenxu Li , Xinhua Zhao , Yingying Tian , Xiaoyan Lang , Dachi Yang . Polyethylene imine functionalized porous carbon framework for selective nitrogen dioxide sensing with smartphone communication. Chinese Chemical Letters, 2024, 35(9): 109230-. doi: 10.1016/j.cclet.2023.109230

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1079)
HTML views(12)

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