Diels-Alder Conversion of Acrylic Acid and 2,5-Dimethylfuran to para-Xylene Over Heterogeneous Bi-BTC Metal-Organic Framework Catalysts Under Mild Conditions

Jyun-Yi Yeh^{1

2}, Season S Chen³, Shih-Cheng Li³, Celine H Chen⁴, Tetsuya Shishido⁵, Daniel C W Tsang⁶, Yusuke Yamauchi^{7

8}, Yi-Pei Li³, Kevin C-W Wu^{1

2

3

9}

Affiliations

¹ International Graduate Program of Molecular Science and Technology (NTU-MST), National Taiwan University, No. 1, Sec. 4, Roosevelt Road, Taipei, 10617, Taiwan.
² Taiwan International Graduate Program (TIGP), Academia Sinica, No. 128, Sec. 2 Academia Road, Taipei, 11529, Taiwan.
³ Department of Chemical Engineering, National (Taiwan) University, No. 1, Sec. 4, Roosevelt Road, Taipei, 10617, Taiwan.
⁴ School of Engineering, Brown University, Providence, RI, 02912, USA.
⁵ Department of Applied Chemistry for Environment, Tokyo Metropolitan University, 1-1 Minami-osawa, Hachioji, Tokyo, 192-0397, Japan.
⁶ Department of Civil and Environmental Engineering, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, China.
⁷ JST-ERATO Yamauchi Materials Space-Tectonics Project, Kagami Memorial Research Institute for Materials Science and Technology, Waseda University, 2-8-26 Nishiwaseda, Shinjuku-ku, Tokyo, 169-0051, Japan.
⁸ Australian Institute for Bioengineering and Nanotechnology (AIBN), School of Chemical Engieering, The University of Queensland, Brisbane, QLD, 4072, Australia.
⁹ Center of Atomic Initiative for New Materials, National Taiwan University, No. 1, Sec. 4, Roosevelt Road, Taipei, 10617, Taiwan.

PMID: 33078542
DOI: 10.1002/anie.202013061

Diels-Alder Conversion of Acrylic Acid and 2,5-Dimethylfuran to para-Xylene Over Heterogeneous Bi-BTC Metal-Organic Framework Catalysts Under Mild Conditions

Jyun-Yi Yeh et al. Angew Chem Int Ed Engl. 2021.

. 2021 Jan 11;60(2):624-629.

doi: 10.1002/anie.202013061. Epub 2020 Dec 1.

Authors

Jyun-Yi Yeh^{1

2}, Season S Chen³, Shih-Cheng Li³, Celine H Chen⁴, Tetsuya Shishido⁵, Daniel C W Tsang⁶, Yusuke Yamauchi^{7

8}, Yi-Pei Li³, Kevin C-W Wu^{1

2

3

9}

Affiliations

¹ International Graduate Program of Molecular Science and Technology (NTU-MST), National Taiwan University, No. 1, Sec. 4, Roosevelt Road, Taipei, 10617, Taiwan.
² Taiwan International Graduate Program (TIGP), Academia Sinica, No. 128, Sec. 2 Academia Road, Taipei, 11529, Taiwan.
³ Department of Chemical Engineering, National (Taiwan) University, No. 1, Sec. 4, Roosevelt Road, Taipei, 10617, Taiwan.
⁴ School of Engineering, Brown University, Providence, RI, 02912, USA.
⁵ Department of Applied Chemistry for Environment, Tokyo Metropolitan University, 1-1 Minami-osawa, Hachioji, Tokyo, 192-0397, Japan.
⁶ Department of Civil and Environmental Engineering, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, China.
⁷ JST-ERATO Yamauchi Materials Space-Tectonics Project, Kagami Memorial Research Institute for Materials Science and Technology, Waseda University, 2-8-26 Nishiwaseda, Shinjuku-ku, Tokyo, 169-0051, Japan.
⁸ Australian Institute for Bioengineering and Nanotechnology (AIBN), School of Chemical Engieering, The University of Queensland, Brisbane, QLD, 4072, Australia.
⁹ Center of Atomic Initiative for New Materials, National Taiwan University, No. 1, Sec. 4, Roosevelt Road, Taipei, 10617, Taiwan.

PMID: 33078542
DOI: 10.1002/anie.202013061

Abstract

The heterogeneous metal-organic framework Bi-BTC successfully catalyzed the synthesis of para-xylene from bio-based 2,5-dimethylfuran and acrylic acid in a promising yield (92 %), under relatively mild conditions (160 °C, 10 bar), and with a low reaction-energy barrier (47.3 kJ mol^-1 ). The proposed reaction strategy also demonstrates a remarkable versatility for furan derivatives such as furan and 2-methylfuran.

Keywords: 2,5-dimethylfuran; Bi-BTC; acrylic acid; metal-organic frameworks; para-xylene.

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References

1. D. S. Sholl, R. P. Lively, Nature 2016, 532, 435-437.
1. B. Xiao, M. Zheng, J. Pang, Y. Jiang, H. Wang, R. Sun, A. Wang, X. Wang, T. Zhang, Ind. Eng. Chem. Res. 2015, 54, 5862-5869.
1. R. A. Sheldon, Green Chem. 2014, 16, 950-963.
1. M.-H. Qu, Y.-Z. Wang, C. Wang, X.-G. Ge, D.-Y. Wang, Q. Zhou, Eur. Polym. J. 2005, 41, 2569-2574.
1. Z. Lin, M. Ierapetritou, V. Nikolakis, AIChE J. 2013, 59, 2079-2087.

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Diels-Alder Conversion of Acrylic Acid and 2,5-Dimethylfuran to para-Xylene Over Heterogeneous Bi-BTC Metal-Organic Framework Catalysts Under Mild Conditions

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Diels-Alder Conversion of Acrylic Acid and 2,5-Dimethylfuran to para-Xylene Over Heterogeneous Bi-BTC Metal-Organic Framework Catalysts Under Mild Conditions

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Affiliations

Abstract

References

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