对苯二甲双酰基衍生物稠化剂的合成与润滑性能研究

石油炼制与化工 ›› 2025, Vol. 56 ›› Issue (8): 122-128.

对苯二甲双酰基衍生物稠化剂的合成与润滑性能研究

彭良溢^1,2

1. 中国石化润滑油有限公司合成油脂分公司
2. 清华大学化学工程系

收稿日期:2025-01-17 修回日期:2025-04-07 出版日期:2025-08-12 发布日期:2025-07-28
通讯作者: 彭良溢 E-mail:pengly8182.lube@sinopec.com
基金资助:
中国石化集团B2C类项目;中国石化集团B1类项目

SYNTHESIS AND LUBRICATING PROPERTIES OF TEREPHTHALAMIDE DERIVATIVE THICKENER

Received:2025-01-17 Revised:2025-04-07 Online:2025-08-12 Published:2025-07-28

摘要/Abstract

摘要： 以对苯二甲酸二甲酯和均苯四甲酸二酐为母核，十八烷基胺为端链，设计合成了两种具有氢键和π?π堆积作用的稠化剂十八烷基对苯二甲双酰胺（C₁₈DA）和十八烷基对苯二甲双酰钠（C₁₈DA-COONa），并通过核磁共振波谱和红外光谱确认了其结构；进而，分别以C₁₈DA和C₁₈DA-COONa为稠化剂制备了润滑脂，并考察了其微观形貌、润滑性能和极压性能；最后，基于量子化学和分子动力学理论模拟研究了两种稠化剂的润滑机理。结果表明：与C₁₈DA相比，C₁₈DA-COONa具有更高的熔点、黏度和更好的增稠性能，且更易通过自组装在基础油中形成稳定的三维网络结构；以C₁₈DA-COONa为稠化剂制备的润滑脂在极压性能方面优于以C₁₈DA为稠化剂的润滑脂；模拟显示，与C₁₈DA相比，C₁₈DA-COONa在基础油中更易产生氢键作用，形成螺旋结构的纳米纤维，因而其稠化性能更好，润滑性能更优异。

关键词: 苯酰基衍生物, 稠化剂, 自组装, 润滑, 计算模拟

Abstract: Using dimethyl terephthalate and pyromellitic dianhydride as core structures and octadecylamine as terminal chains, two thickeners including octadecyl terephthalamide (C₁₈DA) and sodium octadecyl terephthalamate (C₁₈DA-COONa)featuring hydrogen bonding and π-π stacking interactions were designed and synthesized. Their molecular structures were confirmed by nuclear magnetic resonance (NMR) spectroscopy and Fourier transform infrared (FT-IR) spectroscopy. Subsequently, lubricating greases were prepared using C₁₈DA and C₁₈DA-COONa as thickeners, and their microstructures, lubricating performance, and extreme pressure properties were systematically investigated. Finally, the lubrication mechanisms of these thickeners were elucidated through quantum chemical calculations and molecular dynamics simulations.Compared to C₁₈DA, C₁₈DA-COONa exhibits a higher melting point, enhanced viscosity, and superior thickening efficiency, with a greater tendency to self-assemble into stable three-dimensional network structures within the base oil.Grease formulated with C₁₈DA-COONa demonstrates significantly improved extreme pressure performance.Molecular simulations reveal that C₁₈DA-COONa generates stronger hydrogen-bonding interactions in the base oil system, facilitating the formation of helical nanofibers. This structural arrangement enhances thickening efficacy and imparts superior tribological properties to the lubricant.

Key words: benzoyl derivatives, thickener, self-assembly, lubrication, computational simulation

彭良溢. 对苯二甲双酰基衍生物稠化剂的合成与润滑性能研究[J]. 石油炼制与化工, 2025, 56(8): 122-128.

参考文献

[1]李程志, 何懿峰.酰胺类润滑脂研究进展[J].石油炼制与化工, 2021, 52(08):122-128
[2]郑会, 周巍峰, 崔佩娟, 等.长寿命低挥发性润滑脂的性能研究[J].石油炼制与化工, 2024, 55(07):111-118
[3]黎小辉, 胡远海, 杨露露, 等.聚脲基润滑脂发展研究Ⅰ——组成、结构与性能[J].润滑与密封, 2023, 48(08):196-205
[4]蔡梦莹, 刘韦江, 左明明, 等.稠化剂组成对聚脲润滑脂性能的影响[J].润滑与密封, 2020, 45(12):119-124
[5]Zhang W, Zhang Z, Zhao S, et al.Pyromellitic-based low molecular weight gelators and computational studies of intermolecular interactions: a potential additive for lubricant[J].Langmuir, 2021, 37(9):2954-2962
[6]徐状, 任佳, 赵改青, 等.胺分子结构对聚脲润滑脂流变学性能的影响[J].摩擦学学报, 2020, 40(03):378-384
[7]Pramanik M, Mendon S K, Rawlins J W.Vegetable oil based fatty amide as hydrophobes in associative thickener[J].Journal of Applied Polymer Science, 2013, 130(3):1530-1538
[8]Chen W, Wang W, Feng Y, et al.Hydrogen-bonding enhanced current-carrying tribological properties based on ricinoleic acid amides[J].Tribology International, 2024, 199:109958-
[9]Faujdar E, Singh R K.Amide polymers based on N‐phenyl‐p‐phenylenediamine with α‐olefins‐co‐maleic anhydride as multifunctional additives for lubricant application[J].Polymers for Advanced Technologies, 2022, 33(9):2820-2834
[10]Yang C, Song Z, Zhao J, et al.Self-assembly properties of ultra-long-chain gemini surfactants bearing multiple amide groups with high performance in fracturing fluid application[J].Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2017, 523:62-70
[11]谢德生.合成脂肪胺对苯二酸酰胺钠盐稠化剂及其润滑脂的研究[J].石油学报, 1981, 2:93-101
[12]Neese F.The ORCA program system[J].Wiley Interdisciplinary Reviews: Computational Molecular Science, 2012, 2(1):73-78
[13]Lu T, Chen F.Multiwfn: A multifunctional wavefunction analyzer[J].Journal of computational chemistry, 2012, 33(5):580-592
[14]Humphrey W, Dalke A, Schulten K.VMD: visual molecular dynamics[J].Journal of molecular graphics, 1996, 14(1):33-38
[15]Lu T, Chen Q.Interaction region indicator: a simple real space function clearly revealing both chemical bonds and weak interactions[J].Chemistry‐Methods, 2021, 1(5):231-239
[16]Zhang J, Lu T.Efficient evaluation of electrostatic potential with computerized optimized code[J].Physical Chemistry Chemical Physics, 2021, 23(36):20323-20328
[17]Martínez L, Andrade R, Birgin E G, et al.PACKMOL: A package for building initial configurations for molecular dynamics simulations[J].Journal of computational chemistry, 2009, 30(13):2157-2164
[18]Abraham M J, Murtola T, Schulz R, et al.GROMACS: High performance molecular simulations through multi-level parallelism from laptops to supercomputers[J].SoftwareX, 2015, 1:19-25