Catalytic deoxygenation of vanillin over layered double hydroxide supported Pd catalyst

Chanjuan Liao; Xixi Liu; Yongshen Ren; Daoxin Gong; Zehui Zhang

Journal of Industrial and Engineering Chemistry, Vol.68, 380-386, December, 2018

DOI10.1016/j.jiec.2018.08.012 Export Citation

Catalytic deoxygenation of vanillin over layered double hydroxide supported Pd catalyst

Chanjuan Liao, Xixi Liu¹, Yongshen Ren¹, Daoxin Gong, and Zehui Zhang^{1, †}

College of Resources and Environment, Hunan Agricultural University, Changsha, Hunan, 410128, People’s Republic of China
¹Key Laboratory of Catalysis and Materials Sciences of the Ministry of Education, South-Central University for Nationalities, Wuhan, 430074, People’s Republic of China

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A sustainable method was developed for the upgrade of biomass derived vanillin (a typical model compound of lignin) into the potential liquid biofuels over a layered double hydroxide supported Pd catalyst (abbreviated as CoAl-LDH/Pd). The CoAl-LDH/Pd catalyst showed high catalytic activity towards the hydrodeoxygenation of vanillin into 2-methoxy-4-methylphenol (MMP) under mild conditions in aqueous media. High MMP yield up to 86% was produced at 120 °C after 4 h. Kinetic studies revealed that the rate-determining step for the hydrodeoxygenation of vanillin was the hydrogenolysis of vanillyl alcohol. More importantly, the CoAl?LDH/Pd catalyst was highly stable without the loss of activity.

Keywords:Deoxygenation;Vanillin;Pd catalysts;Layered double hydroxides;Mild conditions

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[Referenced By]

[1] Noyori R, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.

[2] Parmeggiani C, Matassini C, Cardona F, Green Chem., 19, 2030 (2017)

[3] Thomas JM, Johnson BFG, Raja R, Sankar G, Midgley PA, Accounts Chem. Res., 36, 20 (2003)

[4] Wang Y, Yao J, Li HR, Su DS, Antonietti M, J. Am. Chem. Soc., 133(8), 2362 (2011)

[5] White RJ, Luque R, Budarin VL, Clark JH, Macquarrie DJ, Chem. Soc. Rev., 38, 481 (2009)

[6] Kondeboina M, Enumula SS, Gurram VRB, Chada RR, Burri DR, Kamaraju SRR, J. Ind. Eng. Chem., 61, 227 (2018)

[7] Mahmood H, Moniruzzaman M, Yusup S, Welton T, Green Chem., 19, 2051 (2017)

[8] Morgan HM, Bu Q, Liang JH, Liu YJ, Mao HP, Shi AP, Lei HW, Ruan R, Bioresour. Technol., 230, 112 (2017)

[9] Xu MZ, Mukarakate C, Iisa K, Budhi S, Menart M, Davidson M, Robichaud DJ, Nimlos MR, Trewyn BG, Richards RM, ACS Sustain. Chem. Eng., 5, 5477 (2017)

[10] Xu X, Li Y, Gong YT, Zhang PF, Li HR, Wang Y, J. Am. Chem. Soc., 134(41), 16987 (2012)

[11] Singuru R, Dhanalaxmi K, Shit SC, Reddy BM, Mondal J, ChemCatChem, 9, 2550 (2017)

[12] Zhu ZB, Tan HY, Wang J, Yu SZ, Zhou KB, Green Chem., 16, 2636 (2014)

[13] Kayalvizhi J, Pandurangan A, Mol. Catal., 436, 67 (2017)

[14] Nie RF, Peng XL, Zhang HF, Yu XL, Lu XH, Zhou D, Xia QH, Catal. Sci. Technol., 7, 627 (2017)

[15] Ibrahim AA, Lin A, Zhang FM, AbouZeid KM, El-Shall MS, ChemCatChem, 9, 469 (2017)

[16] Zhang FM, Zheng S, Xiao Q, Zhong YJ, Zhu WD, Lin A, El-Shall MS, Green Chem., 18, 2900 (2016)

[17] Verma S, Baig RBN, Nadagouda MN, Varma RS, Green Chem., 18, 1327 (2016)

[18] Lv ZF, Sun Q, Meng XJ, Xiao FS, J. Mater. Chem. A, 1, 8630 (2013)

[19] Zhang FM, Jin Y, Fu YH, Zhong YJ, Zhu WD, Ibrahim AA, J. Mater. Chem. A, 3, 17008 (2015)

[20] Nie RF, Yang HH, Zhang HF, Yu XL, Lu XH, Zhou D, Xia QH, Green Chem., 19, 3126 (2017)

[21] Petitjean L, Gagne R, Beach ES, Xiao DQ, Anastas PT, Green Chem., 18, 150 (2016)

[22] Andronescu C, Barwe S, Ventosa E, Masa J, Vasile E, Konkena B, Moller S, Schuhmann W, Angew. Chem.-Int. Edit., 56, 11258 (2017)

[23] Ye T, Huang WM, Zeng LM, Li ML, Shi JL, Appl. Catal. B: Environ., 210, 141 (2017)

[24] Zhang B, Dong Z, Sun D, Wu T, Li Y, J. Ind. Eng. Chem., 49, 208 (2017)

[25] Lu L, Li J, Ng DHL, Yang P, Song P, Zuo M, J. Ind. Eng. Chem., 46, 315 (2017)

[26] Li M, Wei M, Evans DG, Catal. Today, 247, 163 (2017)

[27] Benito P, Herrero M, Barriga C, Labajos FM, Rives V, Inorg. Chem., 47(12), 5453 (2008)

[28] Adachi-Pagano M, Forano C, Besse JP, J. Mater. Chem., 13, 1988 (2003)

[29] Li P, Huang PP, Wei FF, Sun YB, Cao CY, Song WG, J. Mater. Chem. A, 2, 12739 (2014)

[30] Carpani I, Berrettoni M, Giorgetti M, Tonelli D, J. Phys. Chem. B, 110(14), 7265 (2006)

[31] Ma R, Liang JB, Takada K, Sasaki T, J. Am. Chem. Soc., 133 (2010)

[32] Ouyang RH, Jiang DE, ACS Catal., 5, 6624 (2015)

[33] Chen JZ, Liu RL, Guo YY, Chen LM, Gao H, ACS Catal., 5, 722 (2015)

[34] Furimsky E, Massoth FE, Catal. Today, 52(4), 381 (1999)

[35] Bindwal AB, Vaidya PD, Energy Fuels, 28(5), 3357 (2014)