Citation: Yifeng TAN, Ping CAO, Kai MA, Jingtong LI, Yuheng WANG. Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO₃/SiO₂[J]. Chinese Journal of Inorganic Chemistry, ;2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147 shu

Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO₃/SiO₂

Yifeng TAN ¹ ,
Ping CAO ^1,, ,
Kai MA ² ,
Jingtong LI ¹ ,
Yuheng WANG ¹

1.
College of Chemistry and Chemical Engineering, Chongqing University of Technology, Chongqing 400054, China
2.
Southwest Branch of Sinopec Lubricant Co., Ltd., Chongqing 400039, China

Corresponding author: Ping CAO, c.p-9@163.com
Received Date: 17 May 2024
Revised Date: 1 October 2024

Figures(6)

A series of h-MoO₃/SiO₂ catalysts for the synthesis of pentaerythritol tetra(2-ethylthylhexoate)(POE) from pentaerythritol (PER) and 2-ethylhexanoic acid (i-EHA) were prepared by solid-phase milling and characterized and tested by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy (XPS), N₂ adsorption-desorption, scanning electron microscope (SEM) and transmission electron microscope (TEM). The results showed that (200) crystalline facet-selectively oriented h-MoO₃/SiO₂ with h-MoO₃ loading of 15% is an excellent catalyst for the synthesis of POE. Under the suitable reaction process conditions (n_i-EHA/n_PER=4.3, m_{h-MoO₃/SiO₂}/m_PER=0.003, T=220 ℃, t=4 h), the esterification rate was up to 90.83% and the selectivity of POE was up to 100%.
- h-MoO₃/SiO₂,
- preferred orientation of crystal plane,
- pentaerythritol,
- 2-ethylhexanoic acid,
- pentaerythritol tetra(2-ethylthylhexoate)
1. [1]
  Sun Y J, Wang X B, Wang D B, Jin L W, Liu Z G. Absorption of isobutane in three linear chained pentaerythritol esters between 293[J]. 15 and 348.15 K. Int. J. Refrig., 2017,76:118-125. doi: 10.1016/j.ijrefrig.2017.01.021
2. [2]
  ZHU J, GAO X Z, ZHENG W J, HE H Y, WANG H, LIU Z G. Research and application of synthetic ester air compressor oil[J]. Compressor Technology, 2022,3:35-39.
3. [3]
  WANG K M, BAI S J, WANG Y, ZHANG X L, LI Y. Development of refrigerator oil for R410A refrigeration[J]. Refrigeration and Air‑ Conditioning, 2020,20(10):34-36.
4. [4]
  Xu Z, Lou W J, Zhao G Q, Zhang M, Hao J Y, Wang X B. Pentaerythritol rosin ester as an environmentally friendly multifunctional additive in vegetable oil-based lubricant[J]. J. Tribol. Int., 2019,135:213-218. doi: 10.1016/j.triboint.2019.02.038
5. [5]
  FEI Y W, PENG X C, WU N, YANG H W, YAO T, JIANG H Z. Study on evaluation method of thermal oxidation stability of ester aviation lubricating oils[J]. Lubrication Engineering, 2018,43(2):26-30.
6. [6]
  Wang Y, Dong X T, Ma L, Fan M J. Facilitating investigations of sustainable ester oils: Lubricating performance, phytotoxicity indicators, and their structure-activity relationship[J]. ACS Sustain. Chem. Eng., 2024,12(7):2790-2801. doi: 10.1021/acssuschemeng.3c07512
7. [7]
  Arumugam S, Chengareddy P, Sriram G. Synthesis, characterisation and tribological investigation of vegetable oil-based pentaerythryl ester as biodegradable compressor oil[J]. Ind. Crop. Prod., 2018,123:617-628. doi: 10.1016/j.indcrop.2018.07.039
8. [8]
  Sun L, Zhu L, Xue W L, Zeng Z X. Kinetics of p-toluene-sulfonic acid catalyzed direct esterification of pentaerythritol with acrylic acid for pentaerythritol diacrylate production[J]. Chem. Eng. Commun., 2020,207(3):331-338. doi: 10.1080/00986445.2019.1592750
9. [9]
  CAO P, TANG Q Y, MA K, LI Y. Pentaerythritol tetraheptanoate synthesis with molybdenum trioxide[J]. Acta Petrolei Sinica (Petroleum Processing Section), 2021,37(2):298-303. doi: 10.3969/j.issn.1001-8719.2021.02.007
10. [10]
  WANG S Y, DU Y C, NIU S, ZHANG S J, LI X W, CUI Y Q, YANG Q L, TANG J L. Recent development on MoO₃ catalytic material[J]. China Molybdenum Industry, 2023,47(5):1-8.
11. [11]
  ZHANG Y P, WANG J H, HUANG J M, HU Z. Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater[J]. Chinese J. Inorg. Chem., 2024,40(9):1731-1742.
12. [12]
  LI Y H, FENG L J, WANG J G, XU K W, LI C H. Oxidative desulfurization of diesel oil by mesoporous catalyst MoO₃/Al₂O₃[J]. Acta Petrolei Sinica (Petroleum Processing Section), 2011,27(6):878-883.
13. [13]
  ZHOU W W, HAN S Y, CHEN Z P, DUAN Y F, KANG J, FAN F, TIAN C, ZHANG X M. Hierarchical TS-1 zeolite loaded with NiMo catalysts: Preparation and performance in hydrodesulfurization[J]. Chinese J. Inorg. Chem., 2023,39(5):891-905.
14. [14]
  González J, Wang J A, Chen L, Manríquez M, Salmones J, Limas R, Arellano U. Quantitative determination of oxygen defects, surface Lewis acidity, and catalytic properties of mesoporous MoO₃/SBA-15 catalysts[J]. J. Solid State Chem., 2018,263:100-114.
15. [15]
  Zhang F B, Yu X P, Ma F, Yang X G, Hu J, Deng Z Y, Wang G Y. Transesterification of dimethyl oxalate with phenol over a MoO₃/SiO₂ catalyst prepared by thermal spreading[J]. Chin. J. Catal., 2014,35(7):1043-1053.
16. [16]
  Bai K Y, Hao J S, Yang Y X, Qian A N. The effect of hydrothermal temperature on the properties of SBA-15 materials[J]. Heliyon, 2020,6(8)e04436.
17. [17]
  ZHANG H D, WU Y L, YE S Y, HUA Y W, LI P F, XIE F J, MENG Y, YAN Z. Preparation of mesoporous SBA-15 zeolite supported composite metal oxide catalysts and its catalytic performance in selective oxidation of benzaldehyde[J]. Industrial Catalysis, 2022,30(7):31-39.
18. [18]
  Luo J, Liu W, Xiong J, Yang L, Li H P, Yin S, Zhu W S, Li H M. SBA-15 supported molybdenum oxide towards efficient catalytic oxidative desulfurization: Effect of calcination temperature of catalysts[J]. Chin. Adv. Mater. Soc., 2018,6(1):44-54.
19. [19]
  Bibak F, Moradi G. Oxidative desulfurization of model oil and oil cuts with MoO₃/SBA-15: Experimental design and optimization by Box-Behnken method[J]. React. Kinet. Mech. Catal., 2020,131(2):935-951.
20. [20]
  Sen S K, Dutta S, Khan M R, Manir M S, Dutta S, Al Mortuza A, Razia S, Hakim M A. Characterization and antibacterial activity study of hydrothermally synthesized h-MoO₃ nanorods and α-MoO₃ nanoplates[J]. Bionanoscience, 2019,9(4):873-882.
21. [21]
  He Y M, Zhang L H, Wang X X, Wu Y, Lin H J, Zhao L H, Weng W Z, Wan H L, Fan M H. Enhanced photodegradation activity of methyl orange over Z-scheme type MoO₃-g-C₃N₄ composite under visible light irradiation[J]. RSC Adv., 2014,4(26):13610-13619.
22. [22]
  Lin C, Tao K, Yu H B, Hua D Y, Zhou S H. Enhanced catalytic performance of molybdenum-doped mesoporous SBA-15 for metathesis of 1-butene and ethene to propene[J]. Catal. Sci. Technol., 2014,4(11):4010-4019.
23. [23]
  YU X P, ZHANG F B. Transesterification of dimethyl oxalate with phenol over MoO₃/SiO₂ catalysts prepared by sol-gel method[J]. J. Mol. Catal., 2018,32(4):334-341.
24. [24]
  Rana M, Islam M N, Agarwal A, Taki G, Park S J, Dong S, Jo Y T, Park J H. Production of phenol-rich monomers from kraft lignin hydrothermolysates in basic-subcritical water over MoO₃/SBA-15 catalyst[J]. Energy Fuels, 2018,32(11):11564-11575.
25. [25]
  Sun P P, Teng F, Yang Z C, Yang X M, Zhai S Y, Liang S Y, Gu W H, Hao W Y, Shi S Q. Effect of the phase structure on the catalytic activity of MoO₃ and potential application for indoor clearance[J]. J. Mater. Chem. C, 2020,8(7):2475-2482.
26. [26]
  MA L J, HOU M N, MA H B, CAO Z, XUE Z, LU Y R. MoO₃-C₃N₄ photocatalysts with high performance for degradation of methyl orange under visible light[J]. Chinese J. Inorg. Chem., 2018,34(10):1899-1909.
27. [27]
  Kumar V, Wang X, Lee P S. Formation of hexagonal-molybdenum trioxide (h-MoO₃) nanostructures and their pseudocapacitive behavior[J]. Nanoscale, 2015,7(27):11777-11786.
28. [28]
  Etman A S, Abdelhamid H N, Yuan Y Y, Wang L G, Zou X D, Sun J L. Facile water-based strategy for synthesizing MoO_3-x nanosheets: Efficient visible light photocatalysts for dye degradation[J]. ACS Omega, 2018,3(2):2193-2201.
29. [29]
  Wang J Z, Dong S Y, Yu C F, Han X, Guo J Y, Sun J H. An efficient MoO₃ catalyst for in-practical degradation of dye wastewater under room conditions[J]. Catal. Commun., 2017,92:100-104.
30. [30]
  Silva J M D, Sousa R C, Costa J C S, Magalhães J L, Luz G E, de Moura C V R, de Moura E M. Base-free benzyl alcohol aerobic oxidation catalyzed by AuPdNPs supported on SBA-15 and TiO₂/SBA-15 mesoporous materials[J]. Catal. Lett., 2022,152(2):585-599.
31. [31]
  Sun X Z, Du F L. Synthesis, characterization and catalytic properties of monometal/SiO₂ and bimetal/SiO₂ hollow spheres with mesoporous structure[J]. Nano, 2017,12(12)1750148.
32. [32]
  Hassanin M A, Negm S H, Youssef M A, Sakr A K, Mira H I, Mohammmaden T F, Otaibi J S A, Hanfi M H, Sayyed M I, Cheira M F. Sustainable remedy waste to generate SiO₂ functionalized on graphene oxide for removal of U􀃱 ions[J]. Sustainability, 2022,14(5)2699.
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Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO3/SiO2

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Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO₃/SiO₂