Unveiling the Mechanism of Glycerol Oxidation to Lactic Acid on Pt/Sn-MFI Zeolite: an In situ Solid-state NMR Study

doi:10.1007/s40242-024-4168-4

Chemical Research in Chinese Universities ›› 2024, Vol. 40 ›› Issue (6): 935-942.doi: 10.1007/s40242-024-4168-4

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Unveiling the Mechanism of Glycerol Oxidation to Lactic Acid on Pt/Sn-MFI Zeolite: an In situ Solid-state NMR Study

SHEN Xueyuan^1,2, QI Guodong^1,2, LIANG Jiawei^1,2, WANG Ruichen^1,2, XU Jun^1,2, DENG Feng^1,2

1. National Centre for Magnetic Resonance in Wuhan, State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics, Innovation Academy for Precision Measurement Science and Technology, Chinese Academy of Sciences, Wuhan 430071, P. R. China;
2. University of Chinese Academy of Sciences, Beijing 100049, P. R. China

Received:2024-07-19 Online:2024-12-01 Published:2024-10-26
Contact: QI Guodong,qgdong@wipm.ac.cn;XU Jun,xujun@wipm.ac.cn E-mail:qgdong@wipm.ac.cn;xujun@wipm.ac.cn
Supported by:
This work was supported by the National Key R&D Program of China (No. 2022YFA1504500), the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB0540000), the National Natural Science Foundation of China (Nos. 22272185, 22225205, 22320102002, 22127801, 22161132028), the Natural Science Foundation of Hubei Province, China (No. 2021CFA021), the Hubei International Scientific and Technological Cooperation Program, China (No. 2022EHB021), the International Science & Technology Cooperation Base for Sustainable Catalysis and Magnetic Resonance, China (No. SH2303), and the Young Top-notch Talent Cultivation Program of Hubei Province, China.

Abstract

Abstract: Heterogeneous glycerol (GLY) oxidation offers a promising route for the production of lactic acid (LA), a key monomer in biodegradable bioplastics. However, the specific reaction pathways remain poorly understood. This study presents a mechanistic investigation of GLY oxidation to LA using Pt/Sn-MFI catalysts. Characterizations via DR-UV-Vis spectroscopy, ¹¹⁹Sn NMR, and TEM reveal the formation of zeolite framework Sn and well-dispersed Pt nanoparticles in Pt/Sn-MFI. The Lewis acidity of framework Sn in MFI zeolite is confirmed through ³¹P NMR probe techniques. GLY conversion and LA selectivity correlate strongly with framework Sn concentration and the presence of Pt nanoparticles. In situ ¹³C solid-state NMR experiments, complemented by two-dimensional ¹³C correlation NMR, allow real-time monitoring of GLY conversion and identification of various mobile and rigid (surface-adsorbed) species. Results indicate that GLY preferentially transforms to LA via a dihydroxyacetone (DHA) intermediate, facilitated by the Pt-Sn synergistic effect. However, accumulation of surface-adsorbed LA on Sn sites promotes consecutive oxidation of GLY to glyceric acid, tartaric acid, and ultimately CO₂.

Key words: Biomass conversion, In situ NMR, Glycerol oxidation, Zeolite, Reaction mechanism

SHEN Xueyuan, QI Guodong, LIANG Jiawei, WANG Ruichen, XU Jun, DENG Feng. Unveiling the Mechanism of Glycerol Oxidation to Lactic Acid on Pt/Sn-MFI Zeolite: an In situ Solid-state NMR Study[J]. Chemical Research in Chinese Universities, 2024, 40(6): 935-942.

References

[1] Ruggerio C. A., Sci. Total Environ., 2021, 786, 147481.
[2] Lee R., Renewable Resources and Sustainable Development, Springer, Cham, 2019.
[3] Xiang W., Wang W., Du L., Zhao B., Liu X., Zhang X., Yao L., Ge M., Chem. Res. Chinese Universities, 2023, 39, 326.
[4] Jin Y., Hu S., Zhang Z., Zhu B., Bai D., Resour. Chem. Mater., 2022, 1, 129.
[5] Mika L. T., Cséfalvay E., Németh Á., Chem. Rev., 2018, 118, 505.
[6] Corma A., Iborra S., Velty A., Chem. Rev., 2007, 107, 2411.
[7] Besson M., Gallezot P., Pinel C., Chem. Rev., 2014, 114, 1827.
[8] Xu C., Paone E., Rodríguez-Padrón D., Luque R., Mauriello F., Chem. Soc. Rev., 2020, 49, 4273.
[9] Xiao Y., Xiao G., Varma A., Ind. Eng. Chem. Res., 2013, 52, 14291.
[10] Zulqarnain, Yusoff M. H., M. Ayoub M., Ramzan N., Nazir M. H., Zahid I., Abbas N., Elboughdiri N., Mirza C. R., Butt T. A., ACS Omega, 2021, 6, 19099.
[11] Hoekman S. K., Broch A., Robbins C., Ceniceros E., Natarajan M., Renew. Sustain. Energy Rev., 2012, 16, 143.
[12] Ftouni J., Villandier N., Auneau F., Besson M., Djakovitch L., Pinel C., Catal. Today, 2015, 257, 267.
[13] Tran T. T. V., Obpirompoo M., Kongparakul S., Karnjanakom S., Reubroycharoen P., Guan G., Chanlek N., Samart C., Carbon Resour. Convers., 2020, 3, 182.
[14] Diamantopoulou P., Papanikolaou S., Process Biochem., 2023, 124, 113.
[15] Katryniok B., Kimura H., Skrzyńska E., Girardon J.-S., Fongarland P., Capron M., Ducoulombier R., Mimura N., Paul S., Dumeignil F., Green Chem., 2011, 13, 1960.
[16] Metsoviti M., Zeng A.-P., Koutinas A. A., Papanikolaou S., J. Biotechnol., 2013, 163, 408.
[17] Lumongga Putri Tambunan M., Abdullah I., Krisyuningsih Krisnandi Y., Carbon Resour., 2024, 7, 100188.
[18] Filippousi R., Tsouko E., Mordini K., Ladakis D., Koutinas A. A., Aggelis G., Papanikolaou S., Carbon Resour. Convers., 2022, 5, 92.
[19] Khouri N. G., Bahú J. O., Blanco-Llamero C., Severino P., Concha V. O. C., Souto E. B., J. Mol. Struct., 2024, 1309, 138243.
[20] Feng S., Zhao W., He J., Zhang Y., Chem. Res. Chinese Universities, 2023, 39, 750.
[21] Wang Z., Zhang Y., Wang Y., Li J., Jia X., Wu Z., Carbon Resour. Convers., https://doi.org/10.1016/j.crcon.2024.100250
[22] Kishida H., Jin F., Zhou Z., Moriya T., Enomoto H., Chem. Lett., 2005, 34, 1560.
[23] Shen Y., Zhang S., Li H., Ren Y., Liu H., Chem. Eur. J., 2010, 16, 7368.
[24] Lakshmanan P., Upare P. P., Le N. T., Hwang Y. K., Hwang D. W., Lee U. H., Kim H. R., Chang J. S., Appl. Catal. A: Gen., 2013, 468, 260.
[25] Roy D., Subramaniam B., Chaudhari R. V., ACS Catal., 2011, 1, 548.
[26] Sharninghausen L. S., Campos J., Manas M. G., Crabtree R. H., Nat. Commun., 2014, 5, 5084.
[27] Tsuji A., Rao K. T. V., Nishimura S., Takagaki A., Ebitani K., ChemSusChem, 2011, 4, 542.
[28] Xu J., Zhang H., Zhao Y., Yu B., Chen S., Li Y., Hao L., Liu Z., Green Chem., 2013, 15, 1520.
[29] Tao M., Yi X., Delidovich I., Palkovits R., Shi J., Wang X., ChemSusChem, 2015, 8, 4195.
[30] Wang X., Liang F., Huang C., Li Y., Chen B., Catal. Sci. Technol., 2016, 6, 6551.
[31] Peeters E., Calderon-Ardila S., Hermans I., Dusselier M., Sels B. F., ACS Catal., 2022, 12, 9559.
[32] Cho H. J., Chang C. C., Fan W., Green Chem., 2014, 16, 3428.
[33] Lu T., Fu X., Zhou L., Su Y., Yang X., Han L., Wang J., Song C., ACS Catal., 2017, 7, 7274.
[34] Duan Y., Luo Q., Nie R., Wang J., Zhang Y., Lu T., Xu C., Catalysts, 2022, 12, 104.
[35] Hunger M., Weitkamp J., Angew. Chem. Int. Ed., 2001, 40, 2954.
[36] Qi G. D., Wang Q., Xu J., Deng F., Chem. Soc. Rev., 2021, 50, 8382.
[37] Zasukhin D. S., Kostyukov I. A., Kasyanov I. A., Kolyagin Y. G., Ivanova I. I., Pet. Chem., 2021, 61, 875
[38] Xu J., Wang Q., Li S., Deng F., Solid-state NMR in Zeolite Catalysis, Springer, Singapore, 2019.
[39] Wang W., Xu J., Deng F., Natl. Sci. Rev., 2022, 9, nwac155.
[40] Yuan E., Dai W., Wu G., Guan N., Hunger M., Li L., Microporous Mesoporous Mat., 2018, 270, 265.
[41] Gao W., Qi G., Wang Q., Wang W., Li S., Hung I., Gan Z., Xu J., Deng F., Angew. Chem. Int. Ed., 2021, 60, 10709.
[42] Ye X., Qi G., Xu J., Deng F., Chem. J. Chinese Universities, 2020, 41, 960.
[43] Xia C., Liu Y., Lin M., Peng X., Zhu B., Shu X., Catal. Today, 2018, 316, 193.
[44] Li Z., Qi G., Xu J., Deng F., Chem. J. Chinese Universities, 2022, 43, 20220138.
[45] Qi G., Wang Q., Xu J., Wu Q., Wang C., Zhao X., Meng X., Xiao F., Deng F., Comm. Chem., 2018, 1, 22.
[46] Chu Y., Yu Z., Zheng A., Fang H., Zhang H., Huang S.-J., Liu S. -B., Deng F., J. Phys. Chem. C, 2011, 115, 7660.
[47] Sushkevich V. L., Kots P. A., Kolyagin Y. G., Yakimov A. V., Marikutsa A. V., Ivanova I. I., J. Phys. Chem. C, 2019, 123, 5540.
[48] Sushkevich V. L., Ivanova I. I., Yakimov A. V., J. Phys. Chem. C, 2017, 121, 11437.
[49] Yang G., Zhou L., Han X., J. Mol. Catal. A: Chem., 2012, 363/364, 371.
[50] Wu X., Wang X., Zhang L., Wang X., Song S., Zhang H., Angew. Chem. Int. Ed., 2024, 63, e202317594
[51] Zavrazhnov S. A., Esipovich A. L., Danov S. M., Zlobin S. Y., Belousov A. S., Kinet. Catal., 2018, 59, 459.
[52] Kim K. D., Wang Z., Jiang Y., Hunger M., Huang J., Green Chem., 2019, 21, 3383.
[53] Jaegers N. R., Hu W., Weber T. J., Hu J. Z., Sci. Rep., 2021, 11, 7800.
[54] Mahapatra M., Tysoe W. T., Surf. Sci., 2014, 629, 132.

Unveiling the Mechanism of Glycerol Oxidation to Lactic Acid on Pt/Sn-MFI Zeolite: an In situ Solid-state NMR Study

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