纳米尺度氧化石墨烯层作为高效碳催化剂用于苄醇与芳香醛的绿色氧化

doi:10.1016/S1872-2067(17)62776-1

摘要/Abstract

摘要：

合成了纳米尺度氧化石墨烯（NGO）层，用作碳催化剂高效催化苄醇与芳香醛的氧化反应.对于醇氧化反应，当80℃时H₂O₂存在下，NGOs（20 wt%）可高效催化醇选择性生成醛，其反应速率和产率取决于醇上取代基的性质.对于4-硝基苄醇，反应24 h后，只有10%可转换为相应羧酸.相反，4-甲氧基苄醇和二苯基甲醇分别反应仅9和3 h则可完全转化为对应的羧酸和酮.NGO碳催化剂上芳香醛氧化速率高于醇氧化速率.对于所有的醛，采用7 wt% NGO作催化剂，在70 ^oC反应2-3 h后，就可完全转化为相应羧酸.我们讨论了NGO催化剂结构对苄醇和芳香醛氧化反应影响的可能机理.

关键词: 碳催化剂, 纳米尺度氧化石墨烯, 绿色化学, 氧化, 无金属催化剂, 胶体分散

Abstract:

Nanoscale graphene oxide (NGO) sheets were synthesized and used as carbocatalysts for effective oxidation of benzylic alcohols and aromatic aldehydes. For oxidation of alcohols in the presence of H₂O₂ at 80℃, the NGOs (20% mass fraction) as carbocatalysts showed selectivity toward aldehyde. The rate and yield of this reaction strongly depended on the nature of substituents on the alcohol. For 4-nitrobenzyl alcohol, <10% of it was converted into the corresponding carboxylic acid after 24 h. By contrast, 4-methoxybenzyl alcohol and diphenylmethanol were completely converted into the corresponding carboxylic acid and ketone after only 9 and 3 h, respectively. The conversion rates for oxidation of aromatic aldehydes by NGO carbocatalysts were higher than those for alcohol oxidation. For all the aldehydes, complete conversion to the corresponding carboxylic acids was achieved using 7% (mass fraction) of NGO at 70℃ within 2-3 h. Possible mechanisms for NGO carbocatalyst structure-dependent oxidation of benzyl alcohols and structure-independent oxidation of aromatic aldehydes are discussed.

Key words: Carbocatalyst, Nanoscale graphene oxide, Green chemistry, Oxidation, Metal-free catalyst, Colloidal dispersion

Alireza Sedrpoushan, Masoud Heidari, Omid Akhavan. 纳米尺度氧化石墨烯层作为高效碳催化剂用于苄醇与芳香醛的绿色氧化[J]. 催化学报, 2017, 38(4): 745-757.

Alireza Sedrpoushan, Masoud Heidari, Omid Akhavan. Nanoscale graphene oxide sheets as highly efficient carbocatalysts in green oxidation of benzylic alcohols and aromatic aldehydes[J]. Chinese Journal of Catalysis, 2017, 38(4): 745-757.

×
扫码分享

导出引用管理器 EndNote|Ris|BibTeX

链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(17)62776-1

https://www.cjcatal.com/CN/Y2017/V38/I4/745

参考文献

[1] H. W. Hu, J. H. Xin, H. Hu, X. W. Wang, Y. Y. Kong, Appl. Catal. A, 2015, 492, 1-9.
[2] S. L. Y. Tang, R. L. Smith, M. Poliakoff, Green Chem., 2005, 7, 761-762.
[3] I. T. Horvath, P. T. Anastas, Chem. Rev., 2007, 107, 2169-2173.
[4] O. Akhavan, M. Choobtashani, E. Ghaderi, J. Phys. Chem. C, 2012, 116, 9653-9659.
[5] O. Akhavan, E. Ghaderi, J. Phys. Chem. C, 2009, 113, 20214-20220.
[6] Z. Y. Wang, Y. Huang, W. K. Ho, J. J. Cao, Z. X. Shen, S. C. Lee, Appl. Catal. B, 2016, 199, 123-133.
[7] Y. Huang, W. Wang, Q. Zhang, J. J. Cao, R. J. Huang, W. K. Ho, S. C. Lee, Sci. Rep., 2016, 6, 23435.
[8] Q. Zhang, Y. Huang, L. F. Xu, J. J. Cao, W. K. Ho, S. C. Lee, ACS Appl. Mater. Interfaces, 2016, 8, 4165-4174.
[9] O. Akhavan, J. Colloid Interface Sci., 2009, 336, 117-124.
[10] O. Akhavan, M. Abdolahad, Y. Abdi, S. Mohajerzadeh, Carbon, 2009, 47, 3280-3287.
[11] J. C. Védrine, Appl. Catal. A, 2014, 474, 40-50.
[12] Q. Q. Zhuo, Y. Y. Ma, J. Gao, P. P. Zhang, Y. J. Xia, Y. M. Tian, X. X. Sun, J. Zhong, X. H. Sun, Inorg. Chem., 2013, 52, 3141-3147.
[13] J. Pyun, Angew. Chem. Int. Ed., 2011, 50, 46-48.
[14] J. Zhang, X. Liu, R. Blume, A. H. Zhang, R. Schlögl, D. S. Su, Science, 2008, 322, 73-77.
[15] Y. Wang, X. C. Wang, M. Antonietti, Angew. Chem. Int. Ed., 2012, 51, 68-89.
[16] C. L. Su, K. P. Loh, Acc. Chem. Res., 2013, 46, 2275-2285.
[17] Z. K. Zhao, G. F. Ge, W. Z. Li, X. W. Guo, G. R. Wang, Chin. J. Catal., 2016, 37, 644-670.
[18] S. Navalon, A. Dhakshinamoorthy, M. Alvaro, H. Garcia, Chem. Rev., 2014, 114, 6179-6212.
[19] M. S. Dresselhaus, ACS Nano, 2010, 4, 4344-4349.
[20] M. Prato, J. Mater. Chem., 1997, 7, 1097-1109.
[21] B. J. Li, Z. Xu, J. Am. Chem. Soc., 2009, 131, 16380-16382.
[22] B. Frank, R. Blume, A. Rinaldi, A. Trunschke, R. Schlögl, Angew. Chem. Int. Ed., 2011, 50, 10226-10230.
[23] D. S. Su, N. Maksimova, J. J. Delgado, N. Keller, G. Mestl, M. J. Ledoux, R. Schlögl, Catal. Today, 2005, 102-103, 110-114.
[24] M. F. R. Pereira, J. J. M. Orfao, J. L. Figueiredo, Appl. Catal. A, 2001, 218, 307-318.
[25] B. F. Machado, P. Serp, Catal. Sci. Technol., 2012, 2, 54-75.
[26] J. Y. Diao, H. Y. Liu, Z. B. Feng, Y. J. Zhang, T. Chen, C. X. Miao, W. M. Yang, D. S. Su, Catal. Sci. Technol., 2015, 5, 4950-4953.
[27] D. R. Dreyer, C. W. Bielawski, Chem. Sci., 2011, 2, 1233-1240.
[28] N. Kausar, P. Mukherjee, A. R. Das, RSC Adv., 2016, 6, 88904-88910.
[29] N. Kausar, I. Roy, D. Chattopadhyay, A. R. Das, RSC Adv,. 2016, 6, 22320-22330.
[30] L. R. Radovic, C. Mora-Vilches, A. J. A. Salgado-Casanova, Chin. J. Catal., 2014, 35, 792-797.
[31] S. Verma, H. P. Mungse, N. Kumar, S. Choudhary, S. L. Jain, B. Sain, O. P. Khatri, Chem. Commun., 2011, 47, 12673-12675.
[32] M. R. Acocella, M. Mauro, G. Guerra, ChemSusChem,2014, 7, 3279-3283.
[33] A. Sengupta, C. L. Su, C. L. Bao, C. T. Nai, K. P. Loh, ChemCatChem, 2014, 6, 2507-2511.
[34] A. Vijay Kumar, K. Rama Rao, Tetrahedron Lett., 2011, 52, 5188-5191.
[35] F. J. Liu, J. Sun, L. F. Zhu, X. J. Meng, C. Z. Qi, F. S. Xiao, J. Mater. Chem., 2012, 22, 5495-5502.
[36] J. Y. Ji, G. H. Zhang, H. Y. Chen, S. L. Wang, G. L. Zhang, F. B. Zhang, X. B. Fan, Chem. Sci., 2011, 2, 484-487.
[37] D. R. Dreyer, K. A. Jarvis, P. J. Ferreira, C. W. Bielawski, Polym. Chem., 2012, 3, 757-766.
[38] L. Tan, B. Wang, H. X. Feng, RSC Adv., 2013, 3, 2561-2565.
[39] D. R. Dreyer, H. P. Jia, C. W. Bielawski, Angew. Chem. Int. Ed., 2010, 49, 6813-6816.
[40] X. K. Kong, Q. W. Chen, Z. Y. Lun, J. Mater. Chem. A, 2014, 2, 610-613.
[41] X. Zhang, X. Ji, R. F. Su, B. L. Weeks, Z. Zhang, S. L. Deng, ChemPlusChem, 2013, 78, 703-711.
[42] J. H. Yang, G. Sun, Y. J. Gao, H. B. Zhao, P. Tang, J. Tan, A H. Lu, D. Ma, Energy Environ. Sci., 2013, 6, 793-798.
[43] D. H. Long, W. Li, L. C. Ling, J. Miyawaki, I. Mochida, S. H. Yoon, Langmuir, 2010, 26, 16096-16102.
[44] C. N. R. Rao, A. K. Sood, K. S. Subrahmanyam, A. Govindaraj, Angew. Chem. Int. Ed., 2009, 48, 7752-7777.
[45] C. D. Weber, C. Bradley, M. C. Lonergan, M. M. Li, F. Xu, H. R. Li, Y. Wang, Catal. Sci. Technol., 2016, 6, 3670-3693.
[46] J. L. Long, X. Q. Xie, J. Xu, Q. Gu, L. M. Chen, X. X. Wang, ACS Catal., 2012, 2, 622-631.
[47] A. K. Singh, K. C. Basavaraju, S. Sharma, S. Jang, C. P. Park, D. P. Kim, Green Chem., 2014, 16, 3024-3030.
[48] H. Watanabe, S. Asano, S. I. Fujita, H. Yoshida, M. Arai, ACS Catal., 2015, 5, 2886-2894.
[49] A. Dhakshinamoorthy, A. Primo, P. Concepcion, M. Alvaro, H. Garcia, Chem. Eur. J., 2013, 19, 7547-7554.
[50] X. H. Li, M. Antonietti, Angew. Chem. Int. Ed., 2013, 52, 4572-4576.
[51] Y. J. Gao, G. Hu, J. Zhong, Z. J. Shi, Y. S. Zhu, D. S. Su, J. G. Wang, X. H. Bao, D. Ma, Angew. Chem. Int. Ed., 2013, 52, 2109-2113.
[52] Z. B. Wang, X. C. Lü, J. Weng, Carbon, 2013, 62, 51-60.
[53] R. S. Ribeiro, A. M. T. Silva, J. L. Figueiredo, J. L. Faria, H. T. Gomes, Carbon, 2013, 62, 97-108.
[54] H. J. Sun, N. Gao, K. Dong, J. S. Ren, X. G. Qu, ACS Nano, 2014, 8, 6202-6210.
[55] X. L. Hou, J. L. Li, S. C. Drew, B. Tang, L. Sun, X. G. Wang, J. Phys. Chem. C, 2013, 117, 6788-6793.
[56] O. Ivanciuc, D. J. Klein, L. Bytautas, Carbon, 2002, 40, 2063-2083.
[57] R. C. Feng, W. Zhou, G. H. Guan, C. C. Li, D. Zhang, Y. N. Xiao, L. C. Zheng, W. X. Zhu, J. Mater. Chem., 2012, 22, 3982-3989.
[58] L. Peng, Y. C. Zheng, J. C. Li, Y. Jin, C. Gao, ACS Catal., 2015, 5, 3387-3392.
[59] G. Gonçalves, M. Vila, I. Bdikin, A. de Andrés, N. Emami, R. A. S. Ferreira, L. D. Carlos, J. Grácio, P. A. A. P. Marques, Sci. Rep., 2014, 4, 6735.
[60] F. Yang, M. L. Zhao, B. Z. Zheng, D. Xiao, L. Wu, Y. Guo, J. Mater. Chem., 2012, 22, 25471-25479.
[61] W. S. Hummers Jr., R. E. Offeman, J. Am. Chem. Soc., 1958, 80, 1339-1339.
[62] E. Hashemi, O. Akhavan, M. Shamsara, S. Valimehr, R. Rahighi, RSC Adv., 2014, 4, 60720-60728.
[63] L. M. Dai, Acc. Chem. Res., 2013, 46, 31-42.
[64] J. M. Monteagudo, A. Duran, I. San Martin, A. Carnicer, Appl. Catal. B, 2011, 106, 242-249.
[65] H. C. Schniepp, J. L. Li, M. J. McAllister, H. Sai, M. Herrera-Alonson, D. H. Adamson, R. K. Prud'homme, R. Car, D. A. Seville, I. A. Aksay, J. Phys. Chem. B, 2006, 110, 8535-8539.
[66] M. J. McAllister, J. L. Li, D. H. Adamson, H. C. Schniepp, A. A. Abdala, J. Liu, M. Herrera-Alonso, D. L. Milius, R. Car, R. K. Prud'homme, I. A. Aksay, Chem. Mater., 2007, 19, 4396-4404.
[67] O. Akhavan, Carbon, 2010, 48, 509-519.
[68] L. L. Li, G. H. Wu, G. H. Yang, J. Peng, J. W. Zhao, J. J. Zhu, Nanoscale, 2013, 5, 4015-4039.
[69] A. C. Ferrari, J. Robertson, Phys. Rev. B, 2000, 61, 14095-14107.
[70] S. Stankovich, D. A. Dikin, R. D. Piner, K. A. Kohlhaas, A. Kleinhammes, Y. Y. Jia, Y. Wu, S. T. Nguyen, R. S. Ruoff, Carbon, 2007, 45, 1558-1565.
[71] A. C. Ferrari, J. C. Meyer, V. Scardaci, C. Casiraghi, M. Lazzeri, F. Mauri, S. Piscanec, D. Jiang, K. S. Novoselov, S. Roth, A. K. Geim, Phys. Rev. Lett., 2006, 97, 187401/1-187401/4.
[72] E. E. Ghadim, N. Rashidi, S. Kimiagar, O. Akhavan, F. Manouchehri, E. Ghaderi, Appl. Surf. Sci., 2014, 301, 183-188.
[73] R. J. Li, X. Q. Liu, X. L. Deng, S. R. Zhang, Q. He, X. J. Chang, Mater. Lett. 2012, 76, 247-249.
[74] Y. Liu, C. Y. Liu, Y. Liu, Appl. Surf. Sci., 2011, 257, 5513-5518.
[75] S. Kim, S. W. Hwang, M. K. Kim, D. Y. Shin, D. H. Shin, C. O. Kim, S. B. Yang, J. H. Park, E. Hwang, S. H. Choi, G. Ko, S. Sim, C. Sone, H. J. Choi, S. Bae, B. H. Houg, ACS Nano, 2012, 6, 8203-8208.
[76] J. Cugley R. Meyer, H. H. Günthard, Chem. Phys., 1976, 18, 281-292.
[77] D. Swern, L. P. Witnauer, C. R. Eddy, W. E. Parker, J. Am. Chem. Soc., 1955, 77, 5537-5541.
[78] M. B. Smith, J. March, March's Advanced Organic Chemistry:Reactions, Mechanisms, and Structure, 5th Ed., John Wiley & Sons, 2001.
[79] S. Pohjanvesi, E. L. Mustonen, A. Pukkinen, R. Lehtinen, 2004.
[80] M. Renz, B. Meunier, Eur. J. Org. Chem., 1999, 1999, 737-750.
[81] R. Bruckner, M. Harmata, P. A. Wender, Org. Mech. React. Stereochem. Synth., 2010, 1-855.
[82] S. Sabater, J. A. Mata, E. Peris, ACS Catal,. 2014, 4, 2038-2047.