Study on the catalytic degradation of sodium lignosulfonate to aromatic aldehydes over nano-CuO: Process optimization and reaction kinetics

doi:10.1016/j.cjche.2021.12.028

中国化学工程学报 ›› 2023, Vol. 53 ›› Issue (1): 300-309.DOI: 10.1016/j.cjche.2021.12.028

• Full Length Article • 上一篇下一篇

Study on the catalytic degradation of sodium lignosulfonate to aromatic aldehydes over nano-CuO: Process optimization and reaction kinetics

Yingjie Song^1,2, Shuqi Zhong^1,2, Yingjiao Li^1,2, Kun Dong^1,2, Yong Luo², Guangwen Chu^1,2, Haikui Zou^1,2, Baochang Sun^1,2

1. State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, China;
2. Research Center of the Ministry of Education for High Gravity Engineering and Technology, Beijing University of Chemical Technology, Beijing 100029, China

收稿日期:2021-06-19 修回日期:2021-12-10 出版日期:2023-01-28 发布日期:2023-04-08
通讯作者: Guangwen Chu,E-mail:chugw@mail.buct.edu.cn;Baochang Sun,E-mail:sunbc@mail.buct.edu.cn
基金资助:
This work was supported by the National Key Research and Development Program of China (2019YFA0210302), and the National Natural Science Foundation of China (21878009).

Study on the catalytic degradation of sodium lignosulfonate to aromatic aldehydes over nano-CuO: Process optimization and reaction kinetics

Yingjie Song^1,2, Shuqi Zhong^1,2, Yingjiao Li^1,2, Kun Dong^1,2, Yong Luo², Guangwen Chu^1,2, Haikui Zou^1,2, Baochang Sun^1,2

1. State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, China;
2. Research Center of the Ministry of Education for High Gravity Engineering and Technology, Beijing University of Chemical Technology, Beijing 100029, China

Received:2021-06-19 Revised:2021-12-10 Online:2023-01-28 Published:2023-04-08
Contact: Guangwen Chu,E-mail:chugw@mail.buct.edu.cn;Baochang Sun,E-mail:sunbc@mail.buct.edu.cn
Supported by:
This work was supported by the National Key Research and Development Program of China (2019YFA0210302), and the National Natural Science Foundation of China (21878009).

摘要/Abstract

摘要： As one of the few renewable aromatic resources, the research of depolymerization of lignin into high-value chemicals has attracted extensive attention in recent years. Catalytic wet aerobic oxidation (CWAO) is an effective technology to convert lignin like sodium lignosulfonate (SL), a lignin derivative, into aromatic aldehydes such as vanillin and syringaldehyde. However, how to improve the yield of aromatic aldehyde and conversion efficiency is still a challenge, and many operating conditions that significantly affect the yield of these aromatic compounds have rarely been investigated systematically. In this work, we adopted the stirred tank reactor (STR) for the CWAO process with nano-CuO as catalyst to achieve the conversion of SL into vanillin and syringaldehyde. The effect of operating conditions including reaction time, oxygen partial pressure, reaction temperature, SL concentration, rotational speed, catalyst amount, and NaOH concentration on the yield of single phenolic compound was systematically investigated. The results revealed that all these operating conditions exhibit a significant effect on the aromatic aldehyde yield. Therefore, they should be regulated in an optimal value to obtain high yield of these aldehydes. More importantly, the reaction kinetics of the lignin oxidation was explored. This work could provide basic data for the optimization and design of industrial operation of lignin oxidation.

关键词: Nano-CuO, Sodium lignosulfonate, Catalytic wet aerobic oxidation (CWAO), Aromatic aldehyde, Reaction kinetics

Abstract: As one of the few renewable aromatic resources, the research of depolymerization of lignin into high-value chemicals has attracted extensive attention in recent years. Catalytic wet aerobic oxidation (CWAO) is an effective technology to convert lignin like sodium lignosulfonate (SL), a lignin derivative, into aromatic aldehydes such as vanillin and syringaldehyde. However, how to improve the yield of aromatic aldehyde and conversion efficiency is still a challenge, and many operating conditions that significantly affect the yield of these aromatic compounds have rarely been investigated systematically. In this work, we adopted the stirred tank reactor (STR) for the CWAO process with nano-CuO as catalyst to achieve the conversion of SL into vanillin and syringaldehyde. The effect of operating conditions including reaction time, oxygen partial pressure, reaction temperature, SL concentration, rotational speed, catalyst amount, and NaOH concentration on the yield of single phenolic compound was systematically investigated. The results revealed that all these operating conditions exhibit a significant effect on the aromatic aldehyde yield. Therefore, they should be regulated in an optimal value to obtain high yield of these aldehydes. More importantly, the reaction kinetics of the lignin oxidation was explored. This work could provide basic data for the optimization and design of industrial operation of lignin oxidation.

Key words: Nano-CuO, Sodium lignosulfonate, Catalytic wet aerobic oxidation (CWAO), Aromatic aldehyde, Reaction kinetics

Yingjie Song, Shuqi Zhong, Yingjiao Li, Kun Dong, Yong Luo, Guangwen Chu, Haikui Zou, Baochang Sun. Study on the catalytic degradation of sodium lignosulfonate to aromatic aldehydes over nano-CuO: Process optimization and reaction kinetics[J]. 中国化学工程学报, 2023, 53(1): 300-309.

参考文献

[1] A. Sakakibara, A structural model of softwood lignin, Wood Sci. Technol. 14 (2) (1980) 89–100.
[2] J.I. Hedges, J.R. Ertel, Characterization of lignin by gas capillary chromatography of cupric oxide oxidation products, Anal. Chem. 54 (2) (1982) 174–178.
[3] T.D. Jiang. Lignin-Second Edition. Chemical Industry Press, Beijing, 2009.
[4] J. Ni, Y.T. Wu, F. Tao, Y. Peng, P. Xu, A coenzyme-free biocatalyst for the value-added utilization of lignin-derived aromatics, J. Am. Chem. Soc. 140 (47) (2018) 16001–16005.
[5] F.Y. Peng, R.P. Qiao, Q.L. Lu, C.L. Sun. Studies on the lignin-based flocculant synthesis and its use in the treatment of paper effluent. Chin. J. Ind. Water Treat., 28 (5) (2008) 24-27.
[6] M.P. Pandey, C.S. Kim, Lignin depolymerization and conversion: A review of thermochemical methods, Chem. Eng. Technol. 34 (1) (2011) 29–41.
[7] P.C.R. Pinto, C.E. Costa, A.E. Rodrigues, Oxidation of lignin from eucalyptus globulus pulping liquors to produce syringaldehyde and vanillin, Ind. Eng. Chem. Res. 52 (12) (2013) 4421–4428.
[8] J. Zakzeski, P.C.A. Bruijnincx, A.L. Jongerius, B.M. Weckhuysen, The catalytic valorization of lignin for the production of renewable chemicals, Chem. Rev. 110 (6) (2010) 3552–3599.
[9] H. Lange, S. Decina, C. Crestini, Oxidative upgrade of lignin - Recent routes reviewed, Eur. Polym. J. 49 (6) (2013) 1151–1173.
[10] Q. Xiang, Y.Y. Lee, Production of oxychemicals from precipitated hardwood lignin, Appl. Biochem. Biotechnol. 91-93 (1–9) (2001) 71–80.
[11] R. DiCosimo, H.C. Szabo, Oxidation of lignin model compounds using single-electron-transfer catalysts, J. Org. Chem. 53 (8) (1988) 1673–1679.
[12] A. Gaspar, D.V. Evtuguin, C.P. Neto, Oxygen bleaching of kraft pulp catalysed by Mn(III)-substituted polyoxometalates, Appl. Catal. A Gen. 239 (1–2) (2003) 157–168.
[13] F.G. Sales, L.C.A. Maranhão, N.M. Lima Filho, C.A.M. Abreu, Kinetic evaluation and modeling of lignin catalytic wet oxidation to selective production of aromatic aldehydes, Ind. Eng. Chem. Res. 45 (20) (2006) 6627–6631.
[14] J.C. Villar, A. Caperos, F. García-Ochoa, Oxidation of hardwood kraft-lignin to phenolic derivatives with oxygen as oxidant, Wood Sci. Technol. 35 (3) (2001) 245–255.
[15] H. Woo, K.H. Park, Recent developments in hybrid iron oxide-noble metal nanocatalysts for organic reactions, Catal. Today 278 (2016) 209–226.
[16] V.R. Mate, A. Jha, U.D. Joshi, K.R. Patil, M. Shirai, C.V. Rode, Effect of preparation parameters on characterization and activity of Co₃O₄ catalyst in liquid phase oxidation of lignin model substrates, Appl. Catal. A Gen. 487 (2014) 130–138.
[17] W.X. Guan, X. Chen, S.H. Jin, C. Li, C.W. Tsang, C.H. Liang, Highly stable Nb₂O₅-Al₂O₃ composites supported Pt catalysts for hydrodeoxygenation of diphenyl ether, Ind. Eng. Chem. Res. 56 (47) (2017) 14034–14042.
[18] L. Dong, L.F. Lin, X. Han, X.Q. Si, X.H. Liu, Y. Guo, F. Lu, S. Rudić, S.F. Parker, S.H. Yang, Y.Q. Wang, Breaking the limit of lignin monomer production via cleavage of interunit carbon-carbon linkages, Chem 5 (6) (2019) 1521–1536.
[19] C. Fargues, Á. Mathias, J. Silva, A. Rodrigues, Kinetics of vanillin oxidation, Chem. Eng. Technol. 19 (2) (1996) 127–136.
[20] C. Fargues, Á. Mathias, A. Rodrigues, Kinetics of vanillin production from kraft lignin oxidation, Ind. Eng. Chem. Res. 35 (1) (1996) 28–36.
[21] S.G. Santos, A.P. Marques, D.L.D. Lima, D.V. Evtuguin, V.I. Esteves, Kinetics of eucalypt lignosulfonate oxidation to aromatic aldehydes by oxygen in alkaline medium, Ind. Eng. Chem. Res. 50 (1) (2011) 291–298.
[22] TAPPI Test Method T222 om-11 (2011) Acid-insoluble lignin in wood and pulp. In: Tappi test methods. Technical Association of the Pulp and Paper Industry, Atlanta, GA, 2011.
[23] P.C. Rodrigues Pinto, E.A. Borges da Silva, A.E. Rodrigues, Insights into oxidative conversion of lignin to high-added-value phenolic aldehydes, Ind. Eng. Chem. Res. 50 (2) (2011) 741–748.
[24] J.R. Lobbes, H.P. Fitznar, G. Kattner, High-performance liquid chromatography of lignin-derived phenols in environmental samples with diode array detection, Anal. Chem. 71 (15) (1999) 3008–3012.
[25] M.S. Zhou, K. Huang, X.Q. Qiu, D.J. Yang. Content determination of phenolic hydroxyl and carboxylic acid content of lignin by aqueous phase potentiometric titration. J. Chem. Ind. Eng., 63 (1) (2012) 258-265.
[26] S. Adachi, M. Tanimoto, M. Tanaka, R. Matsuno, Kinetics of the alkaline nitrobenzene oxidation of lignin in rice straw, Chem. Eng. J. 49 (2) (1992) B17–B21.
[27] C.A.E. Costa, P.C.R. Pinto, A.E. Rodrigues, Radar tool for lignin classification on the perspective of its valorization, Ind. Eng. Chem. Res. 54 (31) (2015) 7580–7590.
[28] V.E. Tarabanko, D.V. Petukhov, G.E. Selyutin, New mechanism for the catalytic oxidation of lignin to vanillin, Kinetics Catal. 45 (4) (2004) 569–577.
[29] V.E. Tarabanko, N.A. Fomova, B.N. Kuznetsov, N.M. Ivanchenko, A.V. Kudryashev, On the mechanism of vanillin formation in the catalytic oxidation of lignin with oxygen, React. Kinetics Catal. Lett. 55 (1) (1995) 161–170.
[30] G.X. Wu, M. Heitz, E. Chornet, Improved alkaline oxidation process for the production of aldehydes (vanillin and syringaldehyde) from steam-explosion hardwood lignin, Ind. Eng. Chem. Res. 33 (3) (1994) 718–723.
[31] R. Dubey, R.S. Sharma, D.P. Dubey, S.B. Bhardwaj. Crop productivity, weed dynamics and economics of various rice-based cropping systems in Madhya Pradesh. Int. J. Agricult. Stat. Sci., 7 (2) (2011) 635-644.
[32] K.Z. Zhu, C.B. Liu, X.K. Ye, Y. Wu, Catalysis of hydrotalcite-like compounds in liquid phase oxidation: (I) phenol hydroxylation, Appl. Catal. A Gen. 168 (2) (1998) 365–372.
[33] G.Z. Jiang, D.J. Nowakowski, A.V. Bridgwater, A systematic study of the kinetics of lignin pyrolysis, Thermochimica Acta 498 (1–2) (2010) 61–66.
[34] Tang, Liang. B, Kinetics of the liquid-phase oxidation of toluene by air, Ind. Eng. Chem. Res. 46 (20) (2007) 6442–6448.

Study on the catalytic degradation of sodium lignosulfonate to aromatic aldehydes over nano-CuO: Process optimization and reaction kinetics

Study on the catalytic degradation of sodium lignosulfonate to aromatic aldehydes over nano-CuO: Process optimization and reaction kinetics

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