Phosphotungstic acid immobilized on amino-functionalized TS-1 zeolite as a solid acid catalyst for the synthesis of tributyl citrate

doi:10.1016/j.cjche.2024.03.010

Chinese Journal of Chemical Engineering ›› 2024, Vol. 70 ›› Issue (6): 199-210.DOI: 10.1016/j.cjche.2024.03.010

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Phosphotungstic acid immobilized on amino-functionalized TS-1 zeolite as a solid acid catalyst for the synthesis of tributyl citrate

Pei Li¹, Bianfang Shi¹, Junyao Shen¹, Ran Cui¹, Wenze Guo^1,2, Ling Zhao¹, Zhenhao Xi¹

1. State Key Laboratory of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China;
2. Key Laboratory of Smart Manufacturing in Energy Chemical Process, Ministry of Education, East China University of Science and Technology, Shanghai 200237, China

Received:2024-02-26 Revised:2024-03-28 Online:2024-08-05 Published:2024-06-28
Contact: Wenze Guo,E-mail:wzguo@ecust.edu.cn;Zhenhao Xi,E-mail:zhhxi@ecust.edu.cn
Supported by:
This work was financially supported by the National Natural Science Foundation of China (21978089), the Program of Shanghai Academic/Technology Research Leader (21XD1433000), and Key Research and Development Program of Xinjiang Uygur Autonomous Region (2022B01032-1).

Phosphotungstic acid immobilized on amino-functionalized TS-1 zeolite as a solid acid catalyst for the synthesis of tributyl citrate

Pei Li¹, Bianfang Shi¹, Junyao Shen¹, Ran Cui¹, Wenze Guo^1,2, Ling Zhao¹, Zhenhao Xi¹

1. State Key Laboratory of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China;
2. Key Laboratory of Smart Manufacturing in Energy Chemical Process, Ministry of Education, East China University of Science and Technology, Shanghai 200237, China

通讯作者: Wenze Guo,E-mail:wzguo@ecust.edu.cn;Zhenhao Xi,E-mail:zhhxi@ecust.edu.cn
基金资助:
This work was financially supported by the National Natural Science Foundation of China (21978089), the Program of Shanghai Academic/Technology Research Leader (21XD1433000), and Key Research and Development Program of Xinjiang Uygur Autonomous Region (2022B01032-1).

Abstract

Abstract: The amino-functionalization of TS-1 zeolite followed by immobilization of phosphotungstic acid (HPW) was presented to prepare a strong solid acid catalyst for the synthesis of bio-based tributyl citrate from the esterification of citric acid and n-butanol. γ-Aminopropyltriethoxysilane (APTES) was first grafted on the TS-1 zeolite via the condensation reactions with surface hydroxyl groups, and subsequently the HPW was immobilized via the reaction between the amino groups and the protons from HPW-forming strong ionic bonding. The Keggin structure of HPW and MFI topology of TS-1 zeolite were well maintained after the modifications. The amino-functionalization generated abundant uniformly distributed active sites on TS-1 for HPW immobilization, which promoted the dispersity, abundance, as well as the stability of the acid sites. The tetrahedrally coordinated framework titanium and non-framework titania behaved as weak Lewis acid sites, and the protons from the immobilized HPW acted as the moderate or strong Brønsted acid sites. An optimized TBC yield of 96.2% (mol) with a conversion of -COOH of 98.1% (mol) was achieved at 150 ℃ for 6 h over the HPW immobilized on amino-functionalized TS-1. The catalyst exhibited good stability after four consecutive reaction runs, where the activity leveled off at still a relatively high level after somewhat deactivation possibly caused by the leaching of a small portion of weakly anchored APTES or HPW.

Key words: Amino-functionalization, Phosphotungstic acid, TS-1 zeolite, Esterification, Tributyl citrate

摘要： The amino-functionalization of TS-1 zeolite followed by immobilization of phosphotungstic acid (HPW) was presented to prepare a strong solid acid catalyst for the synthesis of bio-based tributyl citrate from the esterification of citric acid and n-butanol. γ-Aminopropyltriethoxysilane (APTES) was first grafted on the TS-1 zeolite via the condensation reactions with surface hydroxyl groups, and subsequently the HPW was immobilized via the reaction between the amino groups and the protons from HPW-forming strong ionic bonding. The Keggin structure of HPW and MFI topology of TS-1 zeolite were well maintained after the modifications. The amino-functionalization generated abundant uniformly distributed active sites on TS-1 for HPW immobilization, which promoted the dispersity, abundance, as well as the stability of the acid sites. The tetrahedrally coordinated framework titanium and non-framework titania behaved as weak Lewis acid sites, and the protons from the immobilized HPW acted as the moderate or strong Brønsted acid sites. An optimized TBC yield of 96.2% (mol) with a conversion of -COOH of 98.1% (mol) was achieved at 150 ℃ for 6 h over the HPW immobilized on amino-functionalized TS-1. The catalyst exhibited good stability after four consecutive reaction runs, where the activity leveled off at still a relatively high level after somewhat deactivation possibly caused by the leaching of a small portion of weakly anchored APTES or HPW.

关键词: Amino-functionalization, Phosphotungstic acid, TS-1 zeolite, Esterification, Tributyl citrate

Pei Li, Bianfang Shi, Junyao Shen, Ran Cui, Wenze Guo, Ling Zhao, Zhenhao Xi. Phosphotungstic acid immobilized on amino-functionalized TS-1 zeolite as a solid acid catalyst for the synthesis of tributyl citrate[J]. Chinese Journal of Chemical Engineering, 2024, 70(6): 199-210.

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Phosphotungstic acid immobilized on amino-functionalized TS-1 zeolite as a solid acid catalyst for the synthesis of tributyl citrate

Phosphotungstic acid immobilized on amino-functionalized TS-1 zeolite as a solid acid catalyst for the synthesis of tributyl citrate

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