Volume 9 Issue 8
Aug.  2024
Turn off MathJax
Article Contents
Article Navigation >  Green Energy&Environment  > 2024  >  9(8): 1267-1278
Lin Yuan, Yancheng Hu, Guangyi Li, Fengan Han, Aiqin Wang, Yu Cong, Tao Zhang, Feng Wang, Ning Li. Biomass-based production of trimellitic and trimesic acids. Green Energy&Environment, 2024, 9(8): 1267-1278. doi: 10.1016/j.gee.2023.02.004
Citation: Lin Yuan, Yancheng Hu, Guangyi Li, Fengan Han, Aiqin Wang, Yu Cong, Tao Zhang, Feng Wang, Ning Li. Biomass-based production of trimellitic and trimesic acids. Green Energy&Environment, 2024, 9(8): 1267-1278. doi: 10.1016/j.gee.2023.02.004
shu

Biomass-based production of trimellitic and trimesic acids

doi: 10.1016/j.gee.2023.02.004

  • a. CAS Key Laboratory of Science and Technology on Applied Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China;

  • b. University of Chinese Academy of Sciences, 19 A Yuquan Road, Shijingshan District, Beijing, 100049, China;

  • c. School of Chemical Engineering and Technology, China University of Mining and Technology, Xuzhou, 221116, Jiangsu, China;

  • d. State Key Laboratory of Catalysis, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, China

Funds:

22078318), DICP (Grant: DICP I201944), the Joint Fund of the Yulin University and the Dalian National Laboratory for Clean Energy (grant: YLU-DNL Fund 2021020).

2022YFB4201802), National Natural Science Foundation of China (no. 21721004

This work was supported by the National Key R&

D Program of China (no. 2022YFA1504902

22178335

21801239

  • Received date 07 November 2022, Accepted date 06 February 2023, RevRecd date 14 January 2023, Publish date 09 February 2023,
    Abstract
  • The production of industrial chemicals with renewable biomass feedstock holds potential to aid the world in pursuing a carbon-neutral society. Trimellitic and trimesic acids are important commodity chemicals in industry that are prepared by the oxidation of petroleum-derived trimethylbenzene. To reduce the dependence on the limited oil source, we develop a potential sustainable alternative towards trimellitic and trimesic acids using biomass-based 2-methyl-2,4-pentandiol (MPD), acrylate and crotonaldehyde as starting materials. The process for trimellitic acid includes dehydration/D-A reaction of MPD and acrylate, flow aromatization over Pd/C catalyst, hydrolysis and catalytic aerobic oxidation (60% overall yield). The challenging regioselectivity issue of D-A reaction is tackled by a matched combination of temperature and deep eutectic solvent ChCl/HCO2H. Crotonaldehyde can also participate in the reaction, followed by Pd/C-catalyzed decarbonylation/dehydrogenation and oxidation to provide trimesic acid in 54% overall yield. Life cycle assessment implies that compared to conventional fossil process, our biomass-based routes present a potential in reducing carbon emissions.

     

    • FullText(HTML)
  • loading
    • References(51)
  • [1]
    C.W. Team, R.K. Pachauri, L.A. Meyer, Climate Change 2014: Synthesis Report, Intergovernmental Panel on Climate Change (IPCC); https://www.ipcc.ch/site/assets/uploads/2018/02/SYR_AR5_FINAL_full.pdf (2014).
    [2]
    Paris Agreement: United Nations Climate Change; https://unfccc.int/sites/default/files/english_paris_agreement.pdf (2015).
    [3]
    T. Werpy, G. Petersen, Top Value Added Chemicals from Biomass: Volume I-Results of Screening for Potential Candidates from Sugars and Synthesis Gas, National Renewable Energy Laboratory; https://www.nrel.gov/docs/fy04osti/35523.pdf (2004).
    [4]
    J.E. Holladay, J.F. White, J.J. Bozell, D. Johnson, Top Value-Added Chemicals from Biomass: Volume II-Results of Screening for Potential Candidates from Biorefinery Lignin, Pacific Northwest National Laboratory; https://www.pnnl.gov/main/publications/external/technical_reports/PNNL-16983.pdf (2007).
    [5]
    M.J. Biddy, C. Scarlata, C. Kinchin, Chemicals from Biomass: A Market Assessment of Bioproducts with Near-Term Potential; https://www.nrel.gov/docs/fy16osti/65509.pdf (2016).
    [6]
    L.T. Mika, E. Csefalvay, A. Nemeth, Chem. Rev. 118 (2018) 505-613.
    [7]
    W. Deng, Y. Feng, J. Fu, H. Guo, Y. Guo, B. Han, et al., Green Energy Environ. 8 (2023) 10-114.
    [8]
    C.C. Chang, S.K. Green, C.L. Williams, P.J. Dauenhauer, W. Fan, Green Chem. 16 (2014) 585-588.
    [9]
    S.K. Green, R.E. Patet, N. Nikbin, C.L. Williams, C.C. Chang, J.Y. Yu, et al., Appl. Catal. B Environ. 180 (2016) 487-496.
    [10]
    I.F. Teixeira, B.T.W. Lo, P. Kostetskyy, M. Stamatakis, L. Ye, C.C. Tang, et al., Angew. Chem. Int. Ed. 55 (2016) 13061-13066.
    [11]
    Y.C. Hu, N. Li, G.Y. Li, A.Q. Wang, Y. Cong, X.D. Wang, et al., ChemSusChem 10 (2017) 2880-2885.
    [12]
    T. Dai, C.Z. Li, L. Li, Z.B.K. Zhao, B. Zhang, Y. Cong, et al., Angew. Chem. Int. Ed. 57 (2018) 1808-1812.
    [13]
    L. Tao, T.H. Yan, W.Q. Li, Y. Zhao, Q. Zhang, Y.M. Liu, et al., Chem 4 (2018) 2212-2227.
    [14]
    J.A. Mendoza Mesa, F. Brandi, I. Shekova, M. Antonietti, M. Al-Naji, Green Chem. 22 (2020) 7398-7405.
    [15]
    Q.L. Meng, J. Yan, R.Z. Wu, H.Z. Liu, Y. Sun, N.N. Wu, et al., Nat. Commun. 12 (2021) 4534.
    [16]
    J.J. Pacheco, M.E. Davis, P. Natl. Acad. Sci. USA 111 (2014) 8363-8367.
    [17]
    E. Mahmoud, J.Y. Yu, R.J. Gorte, R.F. Lobo, ACS Catal. 5 (2015) 6946-6955.
    [18]
    S. Thiyagarajan, H.C. Genuino, J.C. Van Der Waal, E. De Jong, B.M. Weckhuysen, J. Van Haveren, et al., Angew. Chem. Int. Ed. 55 (2016) 1368-1371.
    [19]
    R. Lu, F. Lu, J.Z. Chen, W.Q. Yu, Q.Q. Huang, J.J. Zhang, et al., Angew. Chem. Int. Ed. 55 (2016) 249-253.
    [20]
    Q.S. Kong, X.L. Li, H.B. Shen, H.J. Xu, Y. Fu, Green Energy Environ. 7 (2022) 957-964.
    [21]
    J.G.H. Hermens, A. Jensma, B.L. Feringa, Angew. Chem. Int. Ed. 61 (2022) e202112618.
    [22]
    L. Yuan, Y.C. Hu, Z.T. Zhao, G.Y. Li, A.Q. Wang, Y. Cong, et al., Angew. Chem. Int. Ed. 61 (2022) e202113471.
    [23]
    Z. Zhao, G. Gao, Y. Xi, J. Wang, P. Sun, Q. Liu, et al., Chem 8 (2022) 1034-1049.
    [24]
    S. Song, J.G. Zhang, G. Gozaydin, N. Yan, Angew. Chem. Int. Ed. 58 (2019) 4934-4937.
    [25]
    S.L. Zhou, J.H. Lai, X.X. Liu, G. Huang, G.L. You, Q. Xu, et al., Green Energy Environ. 7 (2022) 257-265.
    [26]
    I. Scodeller, S. Mansouri, D. Morvan, E. Muller, K. De Oliveira Vigier, R. Wischert, et al., Angew. Chem. Int. Ed. 57 (2018) 10510-10514.
    [27]
    E.M. Karp, T.R. Eaton, V.S.I. Nogue, V. Vorotnikov, M.J. Biddy, E.C.D. Tan, et al., Science 358 (2017) 1307-1310.
    [28]
    S. Song, V. Fung Kin Yuen, L. Di, Q. Sun, K. Zhou, N. Yan, Angew. Chem. Int. Ed. 59 (2020) 19846-19850.
    [29]
    X. Wu, M.V. Galkin, K. Barta, Chem Catal. 1 (2021) 1466-1479.
    [30]
    B. Zhang, T.L. Guo, Y.X. Liu, F.E. Kuhn, C. Wang, Z.B.K. Zhao, et al., Angew. Chem. Int. Ed. 60 (2021) 20666-20671.
    [31]
    X. Chen, S. Song, H.Y. Li, G. Gozaydin, N. Yan, Acc. Chem. Res. 54 (2021) 1711-1722.
    [32]
    The Future of Petrochemicals: Towards a More Sustainable Chemical Industry, International Energy Agency; https://www.connaissancedesenergies.org/sites/default/files/pdf-actualites/the_future_of_petrochemicals.pdf (2018).
    [33]
    M. Rahman, C.S. Brazel, Prog. Polym. Sci. 29 (2004) 1223-1248.
    [34]
    O.M. Yaghi, C.E. Davis, G. Li, H. Li, J. Am. Chem. Soc. 119 (1997) 2861-2868.
    [35]
    G.A. Kinberger, W. Cai, M. Goodman, J. Am. Chem. Soc. 124 (2002) 15162-15163.
    [36]
    V. Freger, G.Z. Ramon, Prog. Polym. Sci. 122 (2021) 101451.
    [37]
    W. Partenheimer, Catal. Today 23 (1995) 69-158.
    [38]
    X. Luo, R. Lu, H. Jiang, X. Si, J. Xu, F. Lu, Ind. Eng. Chem. Res. 60 (2021) 4510-4515.
    [39]
    G.P. Dechaine, F.T.T. Ng, Ind. Eng. Chem. Res. 47 (2008) 9304-9313.
    [40]
    F. Chen, N. Li, S.S. Li, G.Y. Li, A.Q. Wang, Y. Cong, et al., Green Chem. 18 (2016) 5751-5755.
    [41]
    E.V. Makshina, J. Canadell, J. Van Krieken, E. Peeters, M. Dusselier, B.F. Sels, ChemCatChem 11 (2019) 180-201.
    [42]
    S.S. Bhagwat, Y. Li, Y.R. Cortes-Pena, E.C. Brace, T.A. Martin, H. Zhao, et al., ACS Sustain. Chem. Eng. 9 (2021) 16659-16669.
    [43]
    Z.D. Young, S. Hanspal, R.J. Davis, ACS Catal. 6 (2016) 3193-3202.
    [44]
    E.L. Smith, A.P. Abbott, K.S. Ryder, Chem. Rev. 114 (2014) 11060-11082.
    [45]
    S. Nejrotti, A. Antenucci, C. Pontremoli, L. Gontrani, N. Barbero, M. Carbone, et al., ACS Omega 7 (2022) 47449-47461.
    [46]
    N. Yasukawa, H. Yokoyama, M. Masuda, Y. Monguchi, H. Sajiki, Y. Sawama, Green Chem. 20 (2018) 1213-1217.
    [47]
    J. Mitra, X.Y. Zhou, T. Rauchfuss, Green Chem. 17 (2015) 307-313.
    [48]
    L. Yuan, Y. Hu, X. Guo, G. Li, A. Wang, Y. Cong, et al., Chem Catal. 2 (2022) 2302-2311.
    [49]
    M. Frohling, M. Hiete, Sustainability and Life Cycle Assessment in Industrial Biotechnology 2020, Springer.
    [50]
    ISO 14040 (2006) Environmental Management - Life Cycle Assessment - Principles and Framework. (Geneva).
    [51]
    ISO 14044 (2006) Environmental Management - Life Cycle Assessment - Requirements and Guidelines. (Geneva).
    • Relative Articles
    • Supplements(0)
    • Cited By
  • 加载中

Catalog

    通讯作者: 陈斌, bchen63@163.com
    • 1. 

      沈阳化工大学材料科学与工程学院 沈阳 110142

    1. 本站搜索
    2. 百度学术搜索
    3. 万方数据库搜索
    4. CNKI搜索
    Get Citation
    PDF
    XML

    Article Metrics

    Article views (170) PDF downloads(19) Cited by()
    Proportional views

    Publish With GEE

    Contact

    • Email：gee@ipe.ac.cn
    • Tel：010-82627075
    • Address：North 2nd street, Zhongguancun, Haidian District, Beijing, China

    Links

    京ICP备10002620号-1京公网安备 11010802039050号

    Supported by: Beijing Renhe Information Technology Co. Ltd    

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return