Synthesis of Azoxybenzenes by Selective Oxidation of Anilines on Titanium Silicate Molecular Sieves
- Corresponding author: Han Wei, hanwei@njnu.edu.cn Xiao Yaping, xiaoyaping@njnu.edu.cn
Citation:
Song Yuwan, Feng Shaojing, Han Wei, Xiao Yaping. Synthesis of Azoxybenzenes by Selective Oxidation of Anilines on Titanium Silicate Molecular Sieves[J]. Chinese Journal of Organic Chemistry,
;2019, 39(4): 1181-1186.
doi:
10.6023/cjoc201808032
Suresh, S.; Joseph, R.; Jayachandran, B.; Pol, A. V.; Vinod, M. P.; Sudalai, A.; Sonawane, H. R.; Ravindranathan, T. Tetrahedron Lett. 1995, 51, 11305.
doi: 10.1016/0040-4020(95)00692-2
Hwu, J. R.; Das, A. R.; Yang, C. W.; Jiannjyh Huang, A.; Hsu, M. H. Org. Lett. 2005, 7, 3211.
doi: 10.1021/ol050924x
Liu, Y.; Liu, B.; Guo, A.; Dong, Z.; Jin, S.; Lu, Y. Molecules 2011, 16, 3563.
doi: 10.3390/molecules16053563
Kluge, R.; Schulz, M.; Liebsch, S. Tetrahedron Lett. 1996, 52, 5773.
doi: 10.1016/0040-4020(96)00202-5
Rezaeifard, A.; Jafarpour, M.; Naseri, M. A.; Shariati, R. Dyes Pigm. 2008, 76, 840.
doi: 10.1016/j.dyepig.2007.02.008
Yang, F.; Wang, Z.; Zhang, X.; Jiang, L.; Li, Y.; Wang, L. ChemCatChem 2015, 7, 3450.
doi: 10.1002/cctc.v7.21
Barak, G.; Sasson, Y. J. Org. Chem. 1989, 54, 3484.
doi: 10.1021/jo00275a043
(a) Sonawane, H. R.; Pol, A. V.; Moghe, P. P.; Biswas, S. S.; Shariati, R. Chem. Commun. 1994, 25, 1215.
(b) Gontier, S.; Tuel, A. J. Catal. 1995, 157, 124.
(c) Chang, C. F.; Liu, S. T. J. Mol. Catal. A: Chem. 2009, 299, 121.
(d) Das, D. R.; Talukdar, A. K. ChemistrySelect 2017, 2, 8983.
Ghosh, S.; Acharyya, S. S.; Sasaki, T.; Bal, R. Green Chem. 2015, 17, 1867.
doi: 10.1039/C4GC02123A
Acharyya, S. S.; Ghosh, S.; Bal, R. ACS Sustainable Chem. Eng. 2014, 2, 584.
doi: 10.1021/sc5000545
Yang, L.; Shi, G.; Ke, X.; Shena, R.; Zhang, L. CrystEngComm 2014, 16, 1620.
doi: 10.1039/c3ce42252f
For aniline forming polyaniline during the oxidation process, see:
(a) Yu, L.; Huang, Y.; Wei, Z.; Ding, Y.; Su, C.; Xu, Q. ChemInform 2016, 47, 8677.
(b) Yu, L.; Han, Z. Mater. Lett. 2016, 184, 312.
(c) Yu, L.; Han, Z.; Ding, Y. Org. Process Res. Dev. 2016, 20, 2124. (d) Wang, Q.; Jing, X.; Han, J.; Yu, L.; Xu, Q. Mater. Lett. 2018, 215, 65.
(e) Liu, Y.; Tang, D.; Cao, K.; Yu, L.; Han, J.; Xu, Q. J. Catal. 2018, 360, 250.
For an example of the molar ratios of silicon to titanium affecting the selectivity of oxidation of aromatic compounds, see: Mukherjee, P.; Bhaumik, A.; Kumar, R. Ind. Eng. Chem. Res. 2007, 46, 8657.
Barbera, D.; Cavani, F.; D'Alessandro, T.; Fornasari, G.; Guidetti, S.; Aloise, A.; Giordano, G.; Piumetti, M.; Bonelli, B.; Zanzottera, C. J. Catal. 2010, 275, 158.
doi: 10.1016/j.jcat.2010.07.030
Zuo, Y.; Wang, X.; Guo, X. Ind. Eng. Chem. Res. 2011, 50, 8485.
doi: 10.1021/ie200281v
Ahmed, M. H. M.; Muraza, O.; Jamil, A. K.; Shafei, E. N.; Yamani, Z. H.; Choi, K. H. Energy Fuels 2017, 31, 5482.
doi: 10.1021/acs.energyfuels.7b00468
Voutyritsa, E.; Theodorou, A.; Kokotou, M. G.; Kokotos, C. G. Green Chem. 2017, 19, 1291.
doi: 10.1039/C6GC03174A
Chen, Y. F.; Chen, J.; Lin, L. J.; Chuang, G. J. J. Org. Chem. 2017, 82, 11626.
doi: 10.1021/acs.joc.7b01887
Long, Z.; Wang, Z.; Zhou, D.; Wan, D.; You, J. Org. Lett. 2017, 19.
Stowell, J. C.; Lau, C. M. J. Org. Chem. 2002, 51, 1614.
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
Xin Li , Wanting Fu , Ruiqing Guan , Yue Yuan , Qinmei Zhong , Gang Yao , Sheng-Tao Yang , Liandong Jing , Song Bai . Nucleophiles promotes the decomposition of electrophilic functional groups of tetracycline in ZVI/H2O2 system: Efficiency and mechanism. Chinese Chemical Letters, 2024, 35(10): 109625-. doi: 10.1016/j.cclet.2024.109625
Yunkang Tong , Haiqiao Huang , Haolan Li , Mingle Li , Wen Sun , Jianjun Du , Jiangli Fan , Lei Wang , Bin Liu , Xiaoqiang Chen , Xiaojun Peng . Cooperative bond scission by HRP/H2O2 for targeted prodrug activation. Chinese Chemical Letters, 2024, 35(12): 109663-. doi: 10.1016/j.cclet.2024.109663
Bicheng Zhu , Jingsan Xu . S-scheme heterojunction photocatalyst for H2 evolution coupled with organic oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100327-100327. doi: 10.1016/j.cjsc.2024.100327
Cailiang Yue , Nan Sun , Yixing Qiu , Linlin Zhu , Zhiling Du , Fuqiang Liu . A direct Z-scheme 0D α-Fe2O3/TiO2 heterojunction for enhanced photo-Fenton activity with low H2O2 consumption. Chinese Chemical Letters, 2024, 35(12): 109698-. doi: 10.1016/j.cclet.2024.109698
Jing Wang , Zhongliao Wang , Jinfeng Zhang , Kai Dai . Single-layer crystalline triazine-based organic framework photocatalysts with different linking groups for H2O2 production. Chinese Journal of Structural Chemistry, 2023, 42(12): 100202-100202. doi: 10.1016/j.cjsc.2023.100202
Zhenyu Hu , Zhenchun Yang , Shiqi Zeng , Kun Wang , Lina Li , Chun Hu , Yubao Zhao . Cationic surface polarization centers on ionic carbon nitride for efficient solar-driven H2O2 production and pollutant abatement. Chinese Chemical Letters, 2024, 35(10): 109526-. doi: 10.1016/j.cclet.2024.109526
Hao Lv , Zhi Li , Peng Yin , Ping Wan , Mingshan Zhu . Recent progress on non-metallic carbon nitride for the photosynthesis of H2O2: Mechanism, modification and in-situ applications. Chinese Chemical Letters, 2025, 36(1): 110457-. doi: 10.1016/j.cclet.2024.110457
Sikai Wu , Xuefei Wang , Huogen Yu . Hydroxyl-enriched hydrous tin dioxide-coated BiVO4 with boosted photocatalytic H2O2 production. Chinese Journal of Structural Chemistry, 2024, 43(12): 100457-100457. doi: 10.1016/j.cjsc.2024.100457
Gang Hu , Chun Wang , Qinqin Wang , Mingyuan Zhu , Lihua Kang . The controlled oxidation states of the H4PMo11VO40 catalyst induced by plasma for the selective oxidation of methacrolein. Chinese Chemical Letters, 2025, 36(2): 110298-. doi: 10.1016/j.cclet.2024.110298
Zhiqiang Wang , Yajie Gao , Tianjun Wang , Wei Chen , Zefeng Ren , Xueming Yang , Chuanyao Zhou . Photocatalyzed oxidation of water on oxygen pretreated rutile TiO2(110). Chinese Chemical Letters, 2025, 36(4): 110602-. doi: 10.1016/j.cclet.2024.110602
Tong Zhou , Xue Liu , Liang Zhao , Mingtao Qiao , Wanying Lei . Efficient Photocatalytic H2O2 Production and Cr(VI) Reduction over a Hierarchical Ti3C2/In4SnS8 Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020
Ping Lu , Baoyin Du , Ke Liu , Ze Luo , Abiduweili Sikandaier , Lipeng Diao , Jin Sun , Luhua Jiang , Yukun Zhu . Heterostructured In2O3/In2S3 hollow fibers enable efficient visible-light driven photocatalytic hydrogen production and 5-hydroxymethylfurfural oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100361-100361. doi: 10.1016/j.cjsc.2024.100361
Xinyu Yin , Haiyang Shi , Yu Wang , Xuefei Wang , Ping Wang , Huogen Yu . Spontaneously Improved Adsorption of H2O and Its Intermediates on Electron-Deficient Mn(3+δ)+ for Efficient Photocatalytic H2O2 Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312007-. doi: 10.3866/PKU.WHXB202312007
Zhenchun Yang , Bixiao Guo , Zhenyu Hu , Kun Wang , Jiahao Cui , Lina Li , Chun Hu , Yubao Zhao . Molecular engineering towards dual surface local polarization sites on poly(heptazine imide) framework for boosting H2O2 photo-production. Chinese Chemical Letters, 2024, 35(8): 109251-. doi: 10.1016/j.cclet.2023.109251
Xiaodan Wang , Yingnan Liu , Zhibin Liu , Zhongjian Li , Tao Zhang , Yi Cheng , Lecheng Lei , Bin Yang , Yang Hou . Highly efficient electrosynthesis of H2O2 in acidic electrolyte on metal-free heteroatoms co-doped carbon nanosheets and simultaneously promoting Fenton process. Chinese Chemical Letters, 2024, 35(7): 108926-. doi: 10.1016/j.cclet.2023.108926
Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C3N4光催化剂及其高效H2O2光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C3N4纳米片用于高效光催化产H2O2. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C3N4/AgI.x.y heterojunction photocatalyst for simultaneous and stoichiometric production of H2 and H2O2 from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
Yang Xia , Kangyan Zhang , Heng Yang , Lijuan Shi , Qun Yi . 构建双通道路径增强iCOF/Bi2O3 S型异质结在纯水体系中光催化合成H2O2性能. Acta Physico-Chimica Sinica, 2024, 40(11): 2407012-. doi: 10.3866/PKU.WHXB202407012