Catalytic fast pyrolysis of walnut shell for alkylphenols production with nitrogen-doped activated carbon catalyst

doi:10.1007/s11783-020-1317-y

Front. Environ. Sci. Eng.

2021, Vol. 15

Issue (2) : 25 https://doi.org/10.1007/s11783-020-1317-y

RESEARCH ARTICLE

Catalytic fast pyrolysis of walnut shell for alkylphenols production with nitrogen-doped activated carbon catalyst

Shanwei Ma¹, Hang Li¹, Guan Zhang¹, Tahir Iqbal², Kai Li¹, Qiang Lu¹(

)

¹. State Key Laboratory of Alternate Electric Power System with Renewable Energy Sources, North China Electric Power University, Beijing 102206, China
². Faculty of Agricultural Engineering & Technology, PMAS-Arid Agriculture University, Rawalpindi 46000, Pakistan

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Abstract

• N-doped activated carbon was prepared for catalytic pyrolysis of walnut shell.

• Alkylphenols were selectively produced from catalytic pyrolysis process.

• The alkylphenols yield increased by 8.5 times under the optimal conditions.

• Formation mechanism of alkylphenols was proposed.

Alkylphenols are a group of valuable phenolic compounds that can be derived from lignocellulosic biomass. In this study, three activated carbons (ACs) were prepared for catalytic fast pyrolysis (CFP) of walnut shell to produce alkylphenols, including nitrogen-doped walnut shell-derived activated carbon (N/WSAC), nitrogen-doped rice husk-derived activated carbon (N/RHAC) and walnut shell-derived activated carbon (WSAC). Pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) experiments were carried out to reveal the influences of AC type, pyrolytic temperature, and AC-to-walnut shell (AC-to-WS) ratio on the product distributions. Results showed that with nitrogen doping, the N/WSAC possessed stronger capability than WSAC toward the alkylphenols production, and moreover, the N/WSAC also exhibited better effects than N/RHAC to prepare alkylphenols. Under the catalysis of N/WSAC, yields of alkylphenols were significantly increased, especially phenol, cresol and 4-ethylphenol. As the increase of pyrolytic temperature, the alkylphenols yield first increased and then decreased, while high selectivity could be obtained at low pyrolytic temperatures. Such a trend was also observed as the AC-to-WS ratio continuously increased. The alkylphenols production achieved a maximal yield of 44.19 mg/g with the corresponding selectivity of 34.7% at the pyrolytic temperature of 400°C and AC-to-WS ratio of 3, compared with those of only 4.67 mg/g and 6.1% without catalyst. In addition, the possible formation mechanism of alkylphenols was also proposed with the catalysis of N/WSAC.

Keywords Pyrolysis Walnut shell Alkylphenols Nitrogen-doped activated carbon

Corresponding Author(s): Qiang Lu

Issue Date: 28 September 2020

Cite this article:

Shanwei Ma,Hang Li,Guan Zhang, et al. Catalytic fast pyrolysis of walnut shell for alkylphenols production with nitrogen-doped activated carbon catalyst[J]. Front. Environ. Sci. Eng., 2021, 15(2): 25.

URL:

https://academic.hep.com.cn/fese/EN/10.1007/s11783-020-1317-y
https://academic.hep.com.cn/fese/EN/Y2021/V15/I2/25

Fig.1 N₂ sorption curves of the three ACs.

Tab.1 Pore structure parameters of the three ACs

Fig.2 SEM micrographs of ACs. (a) WSAC, (b) N/WSAC, (c) N/RHAC.

Fig.3 XPS of spectra. (a) survey spectra; (b–d) N1s spectra of WSAC, N/WSAC, and N/RHAC, respectively.

Fig.4 CO₂-TPD of the catalysts.

Fig.5 Typical ion chromatograms from walnut shell pyrolysis with and without catalysts.

Fig.6 Distributions of different product groups from walnut shell pyrolysis with and without catalysts: (a) peak area of different product groups; (b) relative peak area of different product groups.

Fig.7 Compositions of main phenolic compounds from non-catalytic and CFP of walnut shell: (a) peak area of different phenolic groups; (b) relative peak area of different phenolic groups.

Fig.8 Distributions of the eight product groups at different catalytic pyrolysis temperatures: (a) peak area of different product groups; (b) relative peak area of different product groups.

Fig.9 Compositions of four phenolic groups at different catalytic pyrolysis temperatures: (a) peak area of different phenolic groups; (b) relative peak area of different phenolic groups.

Fig.10 Distributions of different product groups with different AC-to-WS ratios: (a) peak area of different product groups; (b) relative peak area of different product groups.

Tab.2 Actual yields of the main phenolics with different AC-to-WS ratios

Fig.11 The possible formation mechanism of alkylphenols with the N/WSAC catalyst.

1	K Açıkalın, F Karaca (2017). Fixed-bed pyrolysis of walnut shell: Parameter effects on yields and characterization of products. Journal of Analytical and Applied Pyrolysis, 125: 234–242 https://doi.org/10.1016/j.jaap.2017.03.018
2	N S Babu, R Sree, P S S Prasad, N Lingaiah (2008). Room-temperature transesterification of edible and nonedible oils using a heterogeneous strong basic Mg/La catalyst. Energy & Fuels, 22(3): 1965–1971 https://doi.org/10.1021/ef700687w
3	X Bai, K H Kim, R C Brown, E Dalluge, C Hutchinson, Y J Lee, D Dalluge (2014). Formation of phenolic oligomers during fast pyrolysis of lignin. Fuel, 128: 170–179 https://doi.org/10.1016/j.fuel.2014.03.013
4	P F Britt, A C Buchanan III, K B Thomas, S K Lee (1995). Pyrolysis mechanisms of lignin: Surface-immobilized model compound investigation of acid-catalyzed and free-radical reaction pathways. Journal of Analytical and Applied Pyrolysis, 33: 1–19 https://doi.org/10.1016/0165-2370(94)00846-S
5	Z Cao, J Engelhardt, M Dierks, M T Clough, G H Wang, E Heracleous, A Lappas, R Rinaldi, F Schüth (2017). Catalysis meets nonthermal separation for the production of (Alkyl)phenols and hydrocarbons from pyrolysis oil. Angewandte Chemie International Edition, 56(9): 2334–2339 https://doi.org/10.1002/anie.201610405
6	W Chen, Y Fang, K Li, Z Chen, M Xia, M Gong, Y Chen, H Yang, X Tu, H Chen (2020). Bamboo wastes catalytic pyrolysis with N-doped biochar catalyst for phenols products. Applied Energy, 260: 114242 https://doi.org/10.1016/j.apenergy.2019.114242
7	Y Deng, S Peng, H Liu, S Li , Y Chen(2019). Mechanism of dichloromethane disproportionation over mesoporous TiO2 under low temperature. Frontiers of Environmental Science & Engineering, 13(2): 21
8	Y Elkasabi, C A Mullen, A A Boateng (2015). Aqueous extractive upgrading of bio-oils created by tail-gas reactive pyrolysis to produce pure hydrocarbons and phenols. ACS Sustainable Chemistry & Engineering, 3(11): 2809–2816 https://doi.org/10.1021/acssuschemeng.5b00730
9	J Geng, W L Wang, Y X Yu, J M Chang, L P Cai, S Q Shi (2017). Adding nickel formate in alkali lignin to increase contents of alkylphenols and aromatics during fast pyrolysis. Bioresource Technology, 227: 1–6 https://doi.org/10.1016/j.biortech.2016.11.036
10	X Guo, Q Wang, T Xu, K Wei, M Yin, P Liang, X Huang, X Zhang (2020). One-step ball milling-prepared nano Fe2O3 and nitrogen-doped graphene with high oxygen reduction activity and its application in microbial fuel cells. Frontiers of Environmental Science & Engineering, 14(2): 30 https://doi.org/10.1007/s11783-019-1209-1
11	S Gupta, G K Gupta, M K Mondal (2019). Slow pyrolysis of chemically treated walnut shell for valuable products: Effect of process parameters and in-depth product analysis. Energy, 181: 665–676 https://doi.org/10.1016/j.energy.2019.05.214
12	X, Wang G, Chen S, Yu H, Quan X Hao(2019). Enhanced activation of peroxymonosulfate by CNT-TiO2 under UV-light assistance for efficient degradation of organic pollutants. Frontiers of Environmental Science & Engineering, 13(5): 77
13	X Jiang, Q Lu, B Hu, J Liu, C Dong, Y Yang (2017). A comprehensive study on pyrolysis mechanism of substituted b-O-4 type lignin dimers. International Journal of Molecular Sciences, 18(11)
14	J S Kim (2015). Production, separation and applications of phenolic-rich bio-oil–A review. Bioresource Technology, 178: 90–98 https://doi.org/10.1016/j.biortech.2014.08.121
15	K Li, W Chen, H Yang, Y Chen, S Xia, M Xia, X Tu, H Chen (2019). Mechanism of biomass activation and ammonia modification for nitrogen-doped porous carbon materials. Bioresource Technology, 280: 260–268 https://doi.org/10.1016/j.biortech.2019.02.039
16	K Li, Z X Wang, G Zhang, M S Cui, Q Lu, Y P Yang (2020). Selective production of monocyclic aromatic hydrocarbons from ex situ catalytic fast pyrolysis of pine over the HZSM-5 catalyst with calcium formate as a hydrogen source. Sustainable Energy & Fuels, 4(2): 538–548 https://doi.org/10.1039/C9SE00605B
17	X Li, L Su, Y Wang, Y Yu, C Wang, X Li, Z Wang (2012). Catalytic fast pyrolysis of Kraft lignin with HZSM-5 zeolite for producing aromatic hydrocarbons. Frontiers of Environmental Science & Engineering, 6(3): 295–303 https://doi.org/10.1007/s11783-012-0410-2
18	Q Lu, X N Ye, Z X Zhang, Z X Wang, M S Cui, Y P Yang (2018a). Catalytic fast pyrolysis of sugarcane bagasse using activated carbon catalyst in a hydrogen atmosphere to selectively produce 4-ethyl phenol. Journal of Analytical and Applied Pyrolysis, 136: 125–131 https://doi.org/10.1016/j.jaap.2018.10.014
19	Q Lu, Z B Zhang, X N Ye, W T Li, B Hu, C Q Dong, Y P Yang (2017). Selective production of 4-ethyl guaiacol from catalytic fast pyrolysis of softwood biomass using Pd/SBA-15 catalyst. Journal of Analytical and Applied Pyrolysis, 123: 237–243 https://doi.org/10.1016/j.jaap.2016.11.021
20	Q Lu, M X Zhou, W T Li, X Wang, M S Cui, Y P Yang (2018b). Catalytic fast pyrolysis of biomass with noble metal-like catalysts to produce high-grade bio-oil: Analytical Py-GC/MS study. Catalysis Today, 302: 169–179 https://doi.org/10.1016/j.cattod.2017.08.029
21	C A Mullen, P C Tarves, A A Boateng (2017). Role of potassium exchange in catalytic pyrolysis of biomass over ZSM-5: formation of alkyl phenols and furans. ACS Sustainable Chemistry & Engineering, 5(3): 2154–2162 https://doi.org/10.1021/acssuschemeng.6b02262
22	H Shafaghat, P S Rezaei, W Daud (2015). Effective parameters on selective catalytic hydrodeoxygenation of phenolic compounds of pyrolysis bio-oil to high-value hydrocarbons. RSC Advances, 5(126): 103999–104042 https://doi.org/10.1039/C5RA22137D
23	K S W Sing (1985). Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity (Recommendations 1984). Pure and Applied Chemistry, 57(4): 603– 619
24	S Totong, P Daorattanachai, A T Quitain, T Kida, N Laosiripojana (2019). Catalytic depolymerization of alkaline lignin into phenolic-based compounds over metal-free carbon-based catalysts. Industrial & Engineering Chemistry Research, 58(29): 13041–13052 https://doi.org/10.1021/acs.iecr.9b01973
25	B B Uzun, N Sarioğlu (2009). Rapid and catalytic pyrolysis of corn stalks. Fuel Processing Technology, 90(5): 705–716 https://doi.org/10.1016/j.fuproc.2009.01.012
26	T P Vispute, H Zhang, A Sanna, R Xiao, G W Huber (2010). Renewable chemical commodity feedstocks from integrated catalytic processing of pyrolysis oils. Science, 330(6008): 1222–1227 https://doi.org/10.1126/science.1194218
27	C Wang, Z Luo, R Diao, X Zhu (2019). Study on the effect of condensing temperature of walnut shells pyrolysis vapors on the composition and properties of bio-oil. Bioresource Technology, 285: 121370 https://doi.org/10.1016/j.biortech.2019.121370
28	K Wang, J Zhang, B H Shanks, R C Brown (2015). Catalytic conversion of carbohydrate-derived oxygenates over HZSM-5 in a tandem micro-reactor system. Green Chemistry, 17(1): 557–564 https://doi.org/10.1039/C4GC01784F
29	S Wang, G Dai, H Yang, Z Luo (2017). Lignocellulosic biomass pyrolysis mechanism: A state-of-the-art review. Progress in Energy and Combustion Science, 62: 33–86 https://doi.org/10.1016/j.pecs.2017.05.004
30	S Wang, Z Li, X Bai, W Yi, P Fu (2018). Catalytic pyrolysis of lignin with red mud derived hierarchical porous catalyst for alkyl-phenols and hydrocarbons production. Journal of Analytical and Applied Pyrolysis, 136: 8–17 https://doi.org/10.1016/j.jaap.2018.10.024
31	X Wu, F Zhu, J Qi, L Zhao, F Yan, C Li (2017). Challenge of biodiesel production from sewage sludge catalyzed by KOH, KOH/activated carbon, and KOH/CaO. Frontiers of Environmental Science & Engineering, 11(2): 3 https://doi.org/10.1007/s11783-017-0913-y
32	M A Yahya, Z Al-Qodah, C W Z Ngah (2015). Agricultural bio-waste materials as potential sustainable precursors used for activated carbon production: A review. Renewable & Sustainable Energy Reviews, 46: 218–235 https://doi.org/10.1016/j.rser.2015.02.051
33	S M Yakout, G Sharaf El-Deen (2016). Characterization of activated carbon prepared by phosphoric acid activation of olive stones. Arabian Journal of Chemistry, 9: S1155–S1162 https://doi.org/10.1016/j.arabjc.2011.12.002
34	Z Yang, H Lei, Y Zhang, K Qian, E Villota, M Qian, G Yadavalli, H Sun (2018). Production of renewable alkyl-phenols from catalytic pyrolysis of Douglas fir sawdust over biomass-derived activated carbons. Applied Energy, 220: 426–436 https://doi.org/10.1016/j.apenergy.2018.03.107
35	H Zhang, S Chen, H Zhang, X Fan, C Gao, H Yu, X Quan (2019a). Carbon nanotubes-incorporated MIL-88B-Fe as highly efficient Fenton-like catalyst for degradation of organic pollutants. Frontiers of Environmental Science & Engineering, 2019, 13 (2): 18
36	Y Zhang, H Lei, Z Yang, D Duan, E Villotaa, R Ruan (2018). From glucose-based carbohydrates to phenol-rich bio-oils integrated with syngas production via catalytic pyrolysis over an activated carbon catalyst. Green Chemistry, 20(14): 3346–3358 https://doi.org/10.1039/C8GC00593A
37	Y Zhang, X Zhu, L Zhang, X Zhu (2019b). Preparation and characterization of microemulsion fuels from diesel and model compound of walnut shell pyrolysis oil. Fuel, 243: 478–484 https://doi.org/10.1016/j.fuel.2019.01.158
38	Z B Zhang, Q Lu, X N Ye, W T Li, B Hu, C Q Dong (2015). Production of phenolic-rich bio-oil from catalytic fast pyrolysis of biomass using magnetic solid base catalyst. Energy Conversion and Management, 106: 1309–1317 https://doi.org/10.1016/j.enconman.2015.10.063
39	K Zou, Y Deng, J Chen, Y Qian, Y Yang, Y Li, G Chen (2018). Hierarchically porous nitrogen-doped carbon derived from the activation of agriculture waste by potassium hydroxide and urea for high-performance supercapacitors. Journal of Power Sources, 378: 579–588 https://doi.org/10.1016/j.jpowsour.2017.12.081

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