Efficient hydrothermal deoxygenation of methyl palmitate to diesel-like hydrocarbons on carbon encapsulated Ni–Sn intermetallic compounds with methanol as hydrogen donor

doi:10.1007/s11705-022-2217-4

Front. Chem. Sci. Eng.

2023, Vol. 17

Issue (2) : 139-155 https://doi.org/10.1007/s11705-022-2217-4

RESEARCH ARTICLE

Efficient hydrothermal deoxygenation of methyl palmitate to diesel-like hydrocarbons on carbon encapsulated Ni–Sn intermetallic compounds with methanol as hydrogen donor

Haonan Shi, Xiaoyu Gu, Yinteng Shi, Dandan Wang, Sihao Shu, Zhongze Wang, Jixiang Chen(

)

Tianjin Key Laboratory of Applied Catalysis Science and Technology, Department of Catalysis Science and Engineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350, China

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Abstract

Porous carbon-encapsulated Ni and Ni–Sn intermetallic compound catalysts were prepared by the one-pot extended Stöber method followed by carbonization and tested for in-situ hydrothermal deoxygenation of methyl palmitate with methanol as the hydrogen donor. During the catalyst preparation, Sn doping reduces the size of carbon spheres, and the formation of Ni–Sn intermetallic compounds restrain the graphitization, contributing to larger pore volume and pore diameter. Consequently, a more facile mass transfer occurs in carbon-encapsulated Ni–Sn intermetallic compound catalysts than in carbon-encapsulated Ni catalysts. During the in-situ hydrothermal deoxygenation, the synergism between Ni and Sn favors palmitic acid hydrogenation to a highly reactive hexadecanal that easily either decarbonylate to n-pentadecane or is hydrogenated to hexadecanol. At high reaction temperature, hexadecanol undergoes dehydrogenation–decarbonylation, generating n-pentadecane. Also, the C–C bond hydrolysis and methanation are suppressed on Ni–Sn intermetallic compounds, favorable for increasing the carbon yield and reducing the H₂ consumption. The n-pentadecane and n-hexadecane yields reached 88.1% and 92.8% on carbon-encapsulated Ni₃Sn₂ intermetallic compound at 330 °C. After washing and H₂ reduction, the carbon-encapsulated Ni₃Sn₂ intermetallic compound remains stable during three recycling cycles. This is ascribed to the carbon confinement that effectively suppresses the sintering and loss of metal particles under harsh hydrothermal conditions.

Keywords extended Stöber method carbon encapsulated Ni–Sn intermetallic compounds confinement in-situ hydrothermal deoxygenation hydrogenation decarbonylation

Corresponding Author(s): Jixiang Chen

About author:

Changjian Wang and Zhiying Yang contributed equally to this work.

Online First Date: 12 December 2022 Issue Date: 27 February 2023

Cite this article:

Haonan Shi,Xiaoyu Gu,Yinteng Shi, et al. Efficient hydrothermal deoxygenation of methyl palmitate to diesel-like hydrocarbons on carbon encapsulated Ni–Sn intermetallic compounds with methanol as hydrogen donor[J]. Front. Chem. Sci. Eng., 2023, 17(2): 139-155.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-022-2217-4
https://academic.hep.com.cn/fcse/EN/Y2023/V17/I2/139

Scheme1 Preparation of carbon-encapsulated Ni–Sn IMC catalysts via one-pot extended St?ber method.

Fig.1 SEM images of fresh (a) Ni@C, (b) Ni–Sn(3/1)@C, (c) Ni–Sn(3/1.8)@C and (d) Ni–Sn(3/4)@C.

Fig.2 XRD patterns of Ni@C and Ni–Sn(3/1)@C before and after in-situ HTDO at 330 °C for 6 h. (a) Ni@C; (b) Ni–Sn(3/1)@C.

Fig.3 XRD patterns of Ni–Sn(x/y)@C(x/y = 1.7–3/4) before and after in-situ HTDO at 330 °C for 6 h. (a) Fresh catalysts; (b) used catalysts.

Fig.4 Raman spectra of RF derived carbon (C), Ni@C and Ni–Sn(x/y)@C.

Fig.5 TEM and HRTEM images of (a) fresh Ni@C, (b) fresh Ni–Sn(3/1.8)@C and (c) used Ni–Sn(3/1.8)@C and (d) TEM-EDS images of fresh Ni–Sn(3/1.8)@C.

Tab.1 Textural properties of Ni@C and Ni–Sn(x/y)@C

Fig.6 N₂ adsorption–desorption isotherms of Ni@C and Ni–Sn(x/y)@C.

Fig.7 XPS spectra of (a) Ni 2p and (b) Sn 3d in Ni@C, Ni–Sn(3/1)@C, Ni–Sn(3/1.8)@C and Ni–Sn(1/1)@C.

Scheme2 In-situ HTDO pathways of methyl palmitate with methanol as hydrogen donor.

Fig.8 In-situ HTDO performance of Ni@C and Ni–Sn(x/y)@C. (a) Conversions of methanol and methyl palmitate, yields of products and carbon balance; (b) moles of gas phase products (reaction condition: 330 °C, 4 g methyl palmitate, 3 g methanol, 8 g water, 0.4 g catalyst, 6 h).

Fig.9 In-situ HTDO performance of Ni–Sn(3/1.8)@C with varied reaction time. (a) Conversions of methanol and methyl palmitate, yields of products and carbon balance; (b) moles of gas phase products (reaction conditions: 330 °C, 4 g methyl palmitate, 3 g methanol, 8 g water, 0.4 g catalyst, 0–6 h).

Tab.2 Conversion of palmitic acid and hexadecanol under different conditions on Ni–Sn(3/1.8)@C

Fig.10 Performance of fresh and used Ni–Sn(3/1.8)@C after (a, b) washing with isopropanol and (c, d) washing with isopropanol and reduction with H₂ at 400 °C, followed by passivation with 0.5 vol % O₂/N₂ flow at room temperature (Reaction condition: 330 °C, 4 g methyl palmitate, 3 g methanol, 8 g water, 0.4 g catalyst, 6 h).

Scheme3 Proposed structure-reactivity relationship on Ni@C and Ni₃Sn₂ IMC@C catalysts.

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