Single Atom Catalysts in Liquid Phase Selective Hydrogenations

Abstract

Single atom catalysts(SACs) offer exceptional atom efficiency, activity, and selectivity for many catalytic systems. In recent years, SACs have demonstrated great potential in liquid phase selective hydrogenation. In this review, we discuss the critical challenge of selective hydrogenation reactions. Meanwhile, we highlight recent achievements in the design and construction of SACs, as well as their application in liquid reactions. Finally, the current issues and future opportunities for development in the field of SACs are given.

Keywords

Single atom catalyst / Selectivity hydrogenation reaction / Liquid phase reaction / Heterogeneous catalyst

References

[1] Qiao B T, Wang A, Yang X F, Allard L F, Jiang Z, Cui Y, Liu J, Li J, Zhang T. Nat. Chem., 2011, 3: 634.

[2] Guo Y, Huang Y, Zeng B, Han B, Akri M, Shi M, Zhao Y, Li Q, Su Y, Li L, Jiang Q, Cui Y T, Li L, Li R, Qiao B, Zhang T. Nat. Commun., 2022, 13: 2648.

[3] Li X, Rong H, Zhang J, Wang D, Li Y. Nano Res., 2020, 13: 1842.

[4] Zhang L L, Zhou M X, Wang A Q, Zhang T. Chem. Rev., 2020, 120: 683.

[5] Liu L, Meira D M, Arenal R, Concepcion P, Puga A V, Corma A. ACS Catal., 2019, 9: 10626.

[6] Zhang H, Watanabe T, Okumura M, Haruta M, Toshima N. Nat. Mater., 2011, 11: 49.

[7] Yang X F, Wang A Q, Qiao B T, Li J, Liu J Y, Zhang T. Acc. Chem. Res., 2013, 46: 1740.

[8] Zhang W, Fu Q, Luo Q, Sheng L, Yang J. JACS Au, 2021, 1: 2130.

[9] Wu X, Zhang H, Zuo S, Dong J, Li Y, Zhang J, Han Y. Nano-Micro Lett., 2021, 13: 136.

[10] Zhang H, Liu G, Shi L, Ye J. Adv. Energy Mater., 2018, 8: 1701343.

[11] Wang L, Guan E, Zhang J, Yang J, Zhu Y, Han Y, Yang M, Cen C, Fu G, Gates B C, Xiao F S. Nat. Commun., 2018, 9: 1362.

[12] Zhao M T, Yuan K, Wang Y, Li G, Guo J, Gu L, Hu W, Zhao H, Tang Z. Nature, 201, 539: 76.

[13] Wei H, Liu X, Wang A, Zhang L, Qiao B, Yang X, Huang Y, Miao S, Liu J, Zhang T. Nat. Commun., 2014, 5: 5634.

[14] Peng Y, Geng Z, Zhao S, Wang L, Li H, Wang X, Zheng X, Zhu J, Li Z, Si R, Zeng J. Nano Lett, 2018, 18: 3785.

[15] Adam R, Cabrero-Antonino J R, Spannenberg A, Junge K, Jackstell R, Beller M. Angew. Chem. Int. Ed., 2017, 56: 3216.

[16] Ye T N, Lu Y, Li J, Nakao T, Yang H, Tada T, Kitano M, Hosono H. J. Am. Chem. Soc., 2017, 139: 17089.

[17] Li Z, Zhang M, Dong X, Ji S, Zhang L, Leng L, Li H, Horton J H, Xu Q, Zhu J. Appl. Catal. B, 2022, 313: 121462.

[18] Serna P, Corma A. ACS Catal., 2015, 5: 7114.

[19] Macino M, Barnes A J, Althahban S M, Qu R, Gibson E K, Morgan D J, Freakley S J, Dimitratos N, Kiely C J, Gao X, Beale A M, Bethell D, He Q, Sankar M, Hutchings G J. Nat. Catal., 2019, 2: 873.

[20] Rassolov A V, Mashkovsky I S, Baeva G N, Bragina G O, Smirnova N S, Markov P V, Bukhtiyarov A V, Warna J, Stakheev A Y, Murzin D Y. Nanomaterials-Basel, 2021, 11: 3286.

[21] Zhao L, Qin X, Zhang X, Cai X, Huang F, Jia Z, Diao J, Xiao D, Jiang Z, Lu R, Wang N, Liu H, Ma D. Adv. Mater., 2022, 34: e2110455.

[22] Lan X C, Wang T F. ACS Catal., 2020, 10: 2764.

[23] Wang X, Liang X, Geng P, Li Q. ACS Catal., 2020, 10: 2395.

[24] Nagpure A S, Gurrala L, Gogoi P, Chilukuri S V. RSC Adv., 201, 6: 44333.

[25] Wu B, Huang H, Yang J, Zheng N, Fu G. Angew. Chem. Int. Ed., 2012, 51: 3440.

[26] Kahsar K R, Schwartz D K, Medlin J W. J. Am. Chem. Soc., 2014, 136: 520.

[27] Pan H, Li J, Lu J, Wang G, Xie W, Wu P, Li X. J. Catal., 2017, 354: 24.

[28] Wang X, He Y, Liu Y, Park J, Liang X. J. Catal., 2018, 366: 61.

[29] Ma Y, Xu G, Wang H, Wang Y, Zhang Y, Fu Y. ACS Catal., 2018, 8: 1268.

[30] Islam M J, Granollers Mesa M, Osatiashtiani A, Manayil J C, Isaacs M A, Taylor M J, Tsatsos S, Kyriakou G. Appl. Catal. B, 2021, 299: 120652.

[31] Fan Y, Zhuang C, Li S, Wang Y, Zou X, Liu X, Huang W, Zhu G. J. Mater. Chem. A, 2021, 9: 1110.

[32] Long X, Li Z, Gao G, Sun P, Wang J, Zhang B, Zhong J, Jiang Z, Li F. Nat. Commun., 2020, 11: 4074.

[33] Sridharan V, Suryavanshi P A, Menendez J C. Chem. Rev., 2011, 111: 7157.

[34] Wang X, Chen W, Zhang L, Yao T, Liu W, Lin Y, Ju H, Dong J, Zheng L, Yan W, Zheng X, Li Z, Wang X, Yang J, He D, Wang Y, Deng Z, Wu Y, Li Y. J. Am. Chem. Soc., 2017, 139: 9419.

[35] Vivancos Á, Beller M, Albrecht M. ACS Catal., 2017, 8: 17.

[36] Guo M, Li C, Yang Q. Catal. Sci. Technol., 2017, 7: 2221.

[37] Li S, Yang Y, Wang Y, Liu H, Tai J, Zhang J, Han B. Catal. Sci. Technol., 2018, 8: 4314.

[38] Li P, Jin Z, Qian Y, Fang Z, Xiao D, Yu G. Mater. Today, 2020, 35: 78.

[39] Lai W H, Miao Z, Wang Y X, Wang J Z, Chou S L. Adv. Energy Mater., 2019, 9: 1900722.

[40] O’Connor N J, Jonayat A S M, Janik M J, Senftle T P. Nat. Catal., 2018, 1: 531.

[41] Li Z, Leng L, Lu X, Zhang M, Xu Q, Horton J H, Zhu J. Nano Res., 2021, 15: 3114.

[42] Li Z, Dong X, Zhang M, Leng L, Chen W, Horton J H, Wang J, Li Z, Wu W. ACS Appl. Mater. Interfaces, 2020, 12: 57569.

[43] Ye T N, Xiao Z, Li J, Gong Y, Abe H, Niwa Y, Sasase M, Kitano M, Hosono H. Nat. Commun., 2020, 11: 1020.

[44] Lou Y, Zheng Y, Li X, Ta N, Xu J, Nie Y, Cho K, Liu J. J. Am. Chem. Soc., 2019, 141: 19289.

[45] Su H, Chen L, Chen Y, Si R, Wu Y, Wu X, Geng Z, Zhang W, Zeng J. Angew. Chem. Int. Ed., 2020, 59: 20411.

[46] Bi Q, Yuan X, Lu Y, Wang D, Huang J, Si R, Sui M, Huang F. Research (Wash D C), 2020, 2020: 9140841.

[47] Yang F, Ding S, Song H, Yan N. Sci. China Mater., 2020, 63: 982.

[48] Han B, Guo Y, Huang Y, Xi W, Xu J, Luo J, Qi H, Ren Y, Liu X, Qiao B, Zhang T. Angew. Chem. Int. Ed., 2020, 59: 11824.

[49] Wang J, Liu C-Y, Senftle T P, Zhu J, Zhang G, Guo X, Song C. ACS Catal., 2019, 10: 3264.

[50] Ye X, Yang C, Pan X, Ma J, Zhang Y, Ren Y, Liu X, Li L, Huang Y. J. Am. Chem. Soc., 2020, 142: 19001.

[51] Frei M S, Mondelli C, Garcia-Muelas R, Kley K S, Puertolas B, Lopez N, Safonova O V, Stewart J A, Curulla Ferre D, Perez-Ramirez J. Nat. Commun., 2019, 10: 3377.

[52] Sun K, Rui N, Shen C, Liu C-J. J. Phys. Chem. C, 2021, 125: 10926.

[53] Ma Y F, Chi B L, Liu W, Cao L N, Lin Y, Zhang X H, Ye X X, Wei S Q, Lu J L. ACS Catal., 2019, 9: 8404.

[54] Ma Y, Zhang X, Cao L, Lu J. Catal. Sci. Technol., 2021, 11: 2844.

[55] Xiong Y, Dong J, Huang Z Q, Xin P, Chen W, Wang Y, Li Z, Jin Z, Xing W, Zhuang Z, Ye J, Wei X, Cao R, Gu L, Sun S, Zhuang L, Chen X, Yang H, Chen C, Peng Q, Chang C R, Wang D, Li Y. Nat. Nanotechnol., 2020, 15: 390.

[56] Cao L, Luo Q, Liu W, Lin Y, Liu X, Cao Y, Zhang W, Wu Y, Yang J, Yao T, Wei S. Nat. Catal., 2018, 2: 134.

[57] Vile G, Albani D, Nachtegaal M, Chen Z, Dontsova D, Antonietti M, Lopez N, Perez-Ramirez J. Angew. Chem. Int. Ed., 2015, 54: 11265.

[58] Wang L, Zhu C, Xu M, Zhao C, Gu J, Cao L, Zhang X, Sun Z, Wei S, Zhou W, Li W X, Lu J. J. Am. Chem. Soc., 2021, 143: 18854.

[59] Westerhaus F A, Jagadeesh R V, Wienhofer G, Pohl M M, Radnik J, Surkus A E, Rabeah J, Junge K, Junge H, Nielsen M, Bruckner A, Beller M. Nat. Chem., 2013, 5: 537.

[60] He T, Zhang C, Zhang L, Du A. Nano Res., 2019, 12: 1817.

[61] Sheng T, Qi Y-J, Lin X, Hu P, Sun S-G, Lin W-F. Chem. Eng. J., 201, 293: 337.

[62] Li M, Chen S, Jiang Q, Chen Q, Wang X, Yan Y, Liu J, Lv C, Ding W, Guo X. ACS Catal., 2021, 11: 3026.

[63] Zhang L, Shang N, Gao S, Wang J, Meng T, Du C, Shen T, Huang J, Wu Q, Wang H, Qiao Y, Wang C, Gao Y, Wang Z. ACS Catal., 2020, 10: 8672.

[64] Darby M T, Réocreux R, Sykes E C H, Michaelides A, Stamatakis M. ACS Catal., 2018, 8: 5038.

[65] Zhang L, Ren Y, Liu W, Wang A, Zhang T. Natl. Sci. Rev., 2018, 5: 653.

[66] Liu J, Uhlman M B, Montemore M M, Trimpalis A, Giannakakis G, Shan J, Cao S, Hannagan R T, Sykes E C H, Flytzani-Stephanopoulos M. ACS Catal., 2019, 9: 8757.

[67] Kyriakou G, Boucher M B, Jewell A D, Lewis E A, Lawton T J, Baber A E, Tierney H L, Flytzani-Stephanopoulos M, Sykes E C H. Science, 2012, 335: 1209.

[68] Aich P, Wei H, Basan B, Kropf A J, Schweitzer N M, Marshall C L, Miller J T, Meyer R. J. Phys. Chem. C, 2015, 119: 18140.

[69] Liu W, Feng H, Yang Y, Niu Y, Wang L, Yin P, Hong S, Zhang B, Zhang X, Wei M. Nat. Commun., 2022, 13: 3188.

[70] Liu J, Shan J, Lucci F R, Cao S, Sykes E C H, Flytzani-Stephanopoulos M. Catal. Sci. Technol., 2017, 7: 4276.

[71] Li H, Wang L, Dai Y, Pu Z, Lao Z, Chen Y, Wang M, Zheng X, Zhu J, Zhang W, Si R, Ma C, Zeng J. Nat. Nanotechnol., 2018, 13: 411.

[72] Xiao M, Zhang H, Chen Y, Zhu J, Gao L, Jin Z, Ge J, Jiang Z, Chen S, Liu C, Xing W. Nano Energy, 2018, 46: 396.

[73] Tian S, Fu Q, Chen W, Feng Q, Chen Z, Zhang J, Cheong W C, Yu R, Gu L, Dong J, Luo J, Chen C, Peng Q, Draxl C, Wang D, Li Y. Nat. Commun., 2018, 9: 2353.

[74] Hou C-C, Wang H-F, Li C, Xu Q. Energy Environ. Sci., 2020, 13: 1658.

[75] Zhang J, Huang Q-A, Wang J, Wang J, Zhang J, Zhao Y. Chin. J. Catal., 2020, 41: 783.

[76] Shen Q, Jin H, Li P, Yu X, Zheng L, Song W, Cao C. Nano Res., 2022, 15: 5024.

[77] Babucci M, Sarac Oztuna F E, Debefve LM, Boubnov A, Bare S R, Gates B C, Unal U, Uzun A. ACS Catal., 2019, 9: 9905.

[78] Kuo C-T, Lu Y, Arab P, Weeraratne K S, El-Kaderi H, Karim A M. Cell Rep. Phys. Sci., 2021, 2: 100495.