Volume 8 Issue 1
Feb.  2023
Turn off MathJax
Article Contents
Article Navigation >  Green Energy&Environment  > 2023  >  8(1): 331-337
Zhanchao Li, Yizhuo Wang, Qing Li, Liqing Xu, Hong Wang. High tension cyclic hydrocarbons synthesized from biomass-derived platform molecules for aviation fuels in two steps. Green Energy&Environment, 2023, 8(1): 331-337. doi: 10.1016/j.gee.2021.04.012
Citation: Zhanchao Li, Yizhuo Wang, Qing Li, Liqing Xu, Hong Wang. High tension cyclic hydrocarbons synthesized from biomass-derived platform molecules for aviation fuels in two steps. Green Energy&Environment, 2023, 8(1): 331-337. doi: 10.1016/j.gee.2021.04.012
shu

High tension cyclic hydrocarbons synthesized from biomass-derived platform molecules for aviation fuels in two steps

doi: 10.1016/j.gee.2021.04.012

  • a. Frontier Institute of Science and Technology, Xi'an Jiaotong University, Xi'an, 710054, China;

  • b. State Key Laboratory of Multiphase Flow in Power Engineering, Xi'an Jiaotong University, Xi'an, 710054, China

Funds:

H. W. acknowledges financial support from the National Natural Science Foundation of China (grant number: 51876151), the Fundamental Research Funds for the Central Universities, the World-Class Universities(Disciplines), and the Characteristic Development Guidance Funds for the Central Universities (grant number: PY3A010) and the start-up funding from Xi'an Jiaotong University (grant number: QY1J003). This work is also supported by the HPC platform, Xi'an Jiaotong University. We thank the support of H2 Cluster in XJTU. We also thank Prof. Ning Li in DICP, China for his valuable suggestions.

  • Received date 15 January 2021, Accepted date 14 April 2021, RevRecd date 06 April 2021, Publish date 05 May 2021,
    Abstract
  • Synthesizing ring structure aviation fuels from biomass-derived platform molecules is challenging, especially for bridged ring structure aviation fuels which are typically achieved from fossil-derived chemicals. Herein, we report the synthesis of a series of ring structure biofuels in two steps by a combination of a solvent-free Michael-cyclization reaction and a hydrodeoxygenation (HDO) reaction from lignocellulose-derived 5,5-dimethyl-1,3-cyclohexanedione. These biofuels are obtained with high overall yields up to 90%, which exhibit high densities of 0.81 g cm-3-0.88 g cm-3 and high volumetric neat heat of combustion (VNHOC) values of 36.0 MJ L-1-38.6 MJ L-1. More importantly, bridged-ring structure hydrocarbons can also be achieved in two steps by a combination of a Robinson annulation reaction and an HDO reaction to afford the final products at high overall yields up to 90%. The bridged-ring structure products have comparable high densities and high VNHOC values to the best artificial fuel JP-10 (0.94 g cm-3 and 39.6 MJ L-1). The results demonstrate a promising way for the synthesis of high-density aviation fuels with different fuel properties at high yields.

     

    • • A series of high tension cyclic hydrocarbons synthesized from biomass-derived platform molecules. • The products obtained at high yields up to 90% within two steps. • Obtained biofuels exhibited high fuel properties close to those of the best artificial fuel JP-10.
    FullText(HTML)
  • loading
    • References(61)
  • [1]
    E. L. Kunkes, D. A. Simonetti, R. M. West, J. C. Serrano-Ruiz, C. A. Gartner, J. A. Dumesic, Science 322 (2008) 417-421
    [2]
    G. W. Huber, J. N. Chheda, C. J. Barrett, J. A. Dumesic, Science 308 (2005) 1446-1450
    [3]
    P. Sudarsanam, R. Zhong, S. Van Den Bosch, S. M. Coman, V. I. Parvulescu, B. F. Sels, Chem. Soc. Rev. 47 (2018) 8349-8402
    [4]
    M. Zhao, W. Lu, Acta Phys.-Chim. Sin. 35 (2019) 977-988
    [5]
    P. Sudarsanam, E. Peeters, E. V. Makshina, V. I. Parvulescu, B. F. Sels, Chem. Soc. Rev. 48 (2019) 2366-2421
    [6]
    C. H. Zhou, X. Xia, C. X. Lin, D. S. Tong, J. Beltramini, Chem. Soc. Rev. 40 (2011) 5588-5617
    [7]
    C. Zhao, Y. Kou, A. A. Lemonidou, X. Li, J. A. Lercher, Angew. Chem. Int. Ed. 48 (2009) 3987-3990
    [8]
    W. Wang, N. Li, G. Li, S. Li, W. Wang, A. Wang, Y. Cong, X. Wang, T. Zhang, ACS Sustain. Chem. Eng. 5 (2017) 1812-1817
    [9]
    S. Li, F. Chen, N. Li, W. Wang, X. Sheng, A. Wang, Y. Cong, X. Wang, T. Zhang, ChemSusChem 10 (2017) 711-719
    [10]
    H. A. Meylemans, R. L. Quintana, B. R. Goldsmith, B. G. Harvey, ChemSusChem 4 (2011) 465-469
    [11]
    H. S. Chung, C. S. H. Chen, R. A. Kremer, J. R. Boulton, G. W. Burdette, Energ. Fuel 13 (1999) 641-649
    [12]
    J. C. Serrano-Ruiz, R. Luque, A. Sepulveda-Escribano, Chem. Soc. Rev. 40 (2011) 5266-5281
    [13]
    M. J. Climent, A. Corma, S. Iborra, Green Chem. 16 (2014) 516-547
    [14]
    H. Li, A. Riisager, S. Saravanamurugan, A. Pandey, R. S. Sangwan, S. Yang, R. Luque, ACS Catal. 8 (2018) 148-187
    [15]
    Q. Zhu, L. Yin, K. Ji, C. Li, B. Wang, T. Tan, ACS Sustain. Chem. Eng. 8 (2020) 1555-1565
    [16]
    A. Corma, O. De La Torre, M. Renz, Energy Environ. Sci. 5 (2012) 6328-6344
    [17]
    R. Xing, A. V. Subrahmanyam, H. Olcay, W. Qi, G. P. Van Walsum, H. Pendse, G. W. Huber, Green Chem. 12 (2010) 1933-1946
    [18]
    Y. Wang, D. Zhang, Z. Wan, P. Li, C. Zhang, Acta Phys.-Chim. Sin. 35 (2019) 591-597
    [19]
    B. G. Harvey, H. A. Meylemans, J. Chem. Technol. Biotechnol. 86 (2011) 2-9
    [20]
    J. Zou, N. Chang, X. Zhang, L. Wang, ChemCatChem 4 (2012) 1289-1297
    [21]
    J. Xu, N. Li, G. Li, F. Han, A. Wang, Y. Cong, X. Wang, T. Zhang, Green Chem. 20 (2018) 3753-3760
    [22]
    J. Xie, X. Zhang, L. Pan, G. Nie, X. E, Q. Liu, P. Wang, Y. Li, J.J. Zou, Chem. Commun. 53 (2017) 10303-10305
    [23]
    G. Li, B. Hou, A. Wang, X. Xin, T. Zhang, Angew. Chem. Int. Ed. 131 (2019)
    [24]
    S. Takkellapati, T. Li, M. A. Gonzalez, Clean Technol. and Envir. 20 (2018) 1615-1630
    [25]
    P. Durre, Biotechnol. J. 2 (2007) 1525-1534
    [26]
    L. Wu, T. Moteki, A. A. Gokhale, D. W. Flaherty, F. D. Toste, Chem 1 (2016) 32-58
    [27]
    H. Chang, A. H. Motagamwala, G. W. Huber, J. A. Dumesic, Green Chem. 21 (2019) 5532-5540
    [28]
    E. P. Peters, G. J. Schlakman, E. N. Yang, Senior Design Reports; SAE: Ahmedabad, India, Volume 107 (2018)
    [29]
    L. Martinez-Zamora, G. Ros, G. Nieto, Plants 9 (2020) 659
    [30]
    V. R. Dhongde, B. S. De, K. L. Wasewar, J. Chem. Engin. Data 64 (2019) 1072-1084
    [31]
    Majewski, Snieckus, Science of Synthesis (2006) 1011-1040
    [32]
    J. Wang, G. Han, X. Wu, Chin. J. Org. Chem. 23 (2003) 827-831
    [33]
    D. Vorlander, Z. Phys. Chem. 77 (1929) 241-268
    [34]
    Y. Liu, X. Liu, M. Wang, P. He, L. Lin, X. Feng, J. Org. Chem. 77 (2012) 4136-4142
    [35]
    S. Hoz, Acc. Chem. Res. 26 (1993) 69-74
    [36]
    S. Cheng, H. Wang, Y. Xie, Chin. J. Chem. Edu. 36 (2015) 19-21
    [37]
    S. Liu, Q. Zhu, Q. Guan, L. He, W. Li, Bioresour. Technol. 183 (2015) 93-100
    [38]
    Z. Li, R. S. Assary, A. C. Atesin, L. A. Curtiss, T. J. Marks, J. Am. Chem. Soc. 136 (2014) 104-107
    [39]
    T. L. Lohr, Z. Li, R. S. Assary, L. A. Curtiss, T. J. Marks, Energy Environ. Sci. 9 (2016) 550-564
    [40]
    C. Zhao, J. He, A. A. Lemonidou, X. Li, J. A. Lercher, J. Catal. 280 (2011) 8-16
    [41]
    J. W. Ochterski, Thermochemistry in Gaussian 2000
    [42]
    A.D. Sutton, F. D. Waldie, R. Wu, M. Schlaf, L.A. ‘Pete’ Silks, J. C. Gordon, Nat. Chem. 5 (2013) 428-432
    [43]
    B. G. Harvey, R. L. Quintana, Energy Environ. Sci. 3 (2010) 352-357
    [44]
    A. Corma, O. De La Torre, M. Renz, N. Villandier, Angew. Chem. Int. Ed. 50 (2011) 2375-2378
    [45]
    Q. Xia, Q. Cuan, X. Liu, X. Gong, G. Lu, Y. Wang, Angew. Chem. Int. Ed. 53 (2014) 9755-9760
    [46]
    D. Liu, E. Y. X. Chen, ACS Catal. 4 (2014) 1302-1310
    [47]
    L. K. Sharma, K. B. Kim, G. I. Elliott, Green Chem. 13 (2011) 1546-1549
    [48]
    X. Yang, T. Li, K. Tang, X. Zhou, M. Lu, W. L. Ounkham, S. M. Spain, B. J. Frost, H. Lin, Green Chem. 19 (2017) 3566-3573
    [49]
    K. S. Arias, M. J. Climent, A. Corma, S. Iborra, Energy Environ. Sci. 8 (2015) 317-331
    [50]
    N. Ji, X. Wang, C. Weidenthaler, B. Spliethoff, R. Rinaldi, ChemCatChem 7 (2015) 960-966
    [51]
    D. Takei, T. Yatabe, X. Jin, T. Yabe, N. Mizuno, K. Yamaguchi, ACS Catal. 10 (2020) 5057-5063
    [52]
    H. Liu, T. Jiang, B. Han, S. Liang, Y. Zhou, Science 326 (2009) 1250-1252
    [53]
    F. Liu, Q. Liu, A. Wang, T. Zhang, ACS Sustain. Chem. Eng. 4 (2016) 3850-3856
    [54]
    C. Zhao, J. A. Lercher, Angew. Chem. Int. Ed. 51 (2012) 5935-5940
    [55]
    H. O. House, P. C. Gaa, J. H. C. Lee, D. Vanderveer, J. Organ. Chem. 48 (1983) 1670-1678
    [56]
    J. Dauben, H. J. Ringold, R. H. Wade, D. L. Pearson, A. G. Anderson, Organic Synthesis 34 (1954) 19
    [57]
    Q. Deng, G. Nie, L. Pan, J. Zou, X. Zhang, L. Wang, Green Chem. 17 (2015) 4473-4481
    [58]
    X. Sheng, G. Li, W. Wang, Y. Cong, X. Wang, G. W. Huber, N. Li, A. Wang, T. Zhang, AIChE Journal 62 (2016) 2754-2761
    [59]
    P. V. R. Schleyer, J. Am. Chem. Soc. 79 (1957) 3292-3292
    [60]
    P. V. R. Schleyer, M.M. Donaldson, J. Am. Chem. Soc. 82 (1960) 4645-4651
    [61]
    E. Osawa, Y. Tahara, A. Togashi, T. Iizuka, N. Tanaka, T. Kan, D. Farcasiu, G. J. Kent, E. M. Engler, P. V. R. Schleyer, J. Org. Chem. 47 (1982) 1923-1932
    • 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 (207) 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