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Synthesis of Estolide Ester and Amide from Acetylated Polyhydroxy Estolide for Lubricant Base Oil
European Journal of Lipid Science and Technology ( IF 1.8 ) Pub Date : 2020-08-12 , DOI: 10.1002/ejlt.202000098 Seng Soi Hoong 1 , Mohd Zan Arniza 1 , Nek Mat Din Nik Siti Mariam 1 , Abu Hassan Noor Armylisas 1 , Siti Afida Ishak 1 , Tuan Noor Maznee Tuan Ismail 1 , Shoot Kian Yeong 1
European Journal of Lipid Science and Technology ( IF 1.8 ) Pub Date : 2020-08-12 , DOI: 10.1002/ejlt.202000098 Seng Soi Hoong 1 , Mohd Zan Arniza 1 , Nek Mat Din Nik Siti Mariam 1 , Abu Hassan Noor Armylisas 1 , Siti Afida Ishak 1 , Tuan Noor Maznee Tuan Ismail 1 , Shoot Kian Yeong 1
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Plant oil‐based lubricants are used as alternative for mainstream petroleum‐based lubricants mainly because they are known to be environmentally friendly. However, their market acceptance is limited by their high pour point and poor oxidation stability. This study presents an approach to make biodegradable lubricant from oleic acid that shows low pour point and satisfactory oxidation stability. A mixture of estolides with acetyl and hydroxy functionalities is prepared from reaction between oleic acid, acetic acid, and hydrogen peroxide. Subsequently, the hydroxy groups of estolide are end‐capped with lauric acid to improve oxidation stability. Further reaction with alcohol and amine yielded estolide ester and amide, respectively. Physicochemical properties evaluation of prepared estolide ester and amide reveal that they have properties comparable to commercial samples in terms of pour point, oxidation stability, viscosity index, and antiwear. Furthermore, both estolide ester and amide are found to be readily biodegradable, which support their use as environmental friendly lubricant. Therefore, the inferior properties of plant oil‐based lubricants can be resolved by chemical modifications that yield specific estolide ester and amide with excellent properties suitable for lubricants.
中文翻译：
由乙酰化的聚羟基乙酸酯制备润滑油基础油的乙酸酯和酰胺。
植物油基润滑剂被用作主流石油基润滑剂的替代品，主要是因为已知它们对环境友好。然而，它们的高倾点和差的氧化稳定性限制了它们的市场接受度。这项研究提出了一种从油酸制备可生物降解的润滑剂的方法，该方法具有低倾点和令人满意的氧化稳定性。由油酸，乙酸和过氧化氢之间的反应制备具有乙酰基和羟基官能团的雌二醇的混合物。随后，用月桂酸将苯乙内酯的羟基封端，以提高氧化稳定性。与醇和胺进一步反应，分别得到乙内酯和酰胺。所制备的依托内酯酯和酰胺的理化性质评估表明，它们在倾点，氧化稳定性，粘度指数和抗磨性方面的性能可与商业样品媲美。此外，发现estolide酯和酰胺都易于生物降解，这支持它们用作环境友好的润滑剂。因此，可以通过化学修饰来解决植物油基润滑油的劣质性能，这些化学修饰会产生特定的依斯图内酯和酰胺，且具有适用于润滑油的优异性能。
更新日期：2020-10-05
中文翻译：
由乙酰化的聚羟基乙酸酯制备润滑油基础油的乙酸酯和酰胺。
植物油基润滑剂被用作主流石油基润滑剂的替代品，主要是因为已知它们对环境友好。然而，它们的高倾点和差的氧化稳定性限制了它们的市场接受度。这项研究提出了一种从油酸制备可生物降解的润滑剂的方法，该方法具有低倾点和令人满意的氧化稳定性。由油酸，乙酸和过氧化氢之间的反应制备具有乙酰基和羟基官能团的雌二醇的混合物。随后，用月桂酸将苯乙内酯的羟基封端，以提高氧化稳定性。与醇和胺进一步反应，分别得到乙内酯和酰胺。所制备的依托内酯酯和酰胺的理化性质评估表明，它们在倾点，氧化稳定性，粘度指数和抗磨性方面的性能可与商业样品媲美。此外，发现estolide酯和酰胺都易于生物降解，这支持它们用作环境友好的润滑剂。因此，可以通过化学修饰来解决植物油基润滑油的劣质性能，这些化学修饰会产生特定的依斯图内酯和酰胺，且具有适用于润滑油的优异性能。
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