Synthesis and characterization of new esters of oleic acid and glycerol analogues as potential lubricants

Cavalcante, Igor Marques; Rocha, Natália Rodrigues de Castro; Maier, Martin E.; Lima, Ana Paula Dantas de; Neto, Davino M. Andrade; Brito, Débora Hellen Almeida de; Petzhold, César Liberato; Schanz, Maria Telma Gomes Freire; Ricardo, Nágila M.P.S.

doi:10.1016/j.indcrop.2014.08.022

Cited by 34 publications

(27 citation statements)

References 33 publications

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“…The commercial lubricant is composed mainly by linear chains whose function is stress dissipation. Also there were ester and carboxylic groups inside, as observed in the structural characterization, and they promoted anchoring onto the surface 16,19,20,[60][61][62] . Those structures are in agreement with the wettability results, since the longer the linear chains the bigger the area where they can place and interact on the metallic surface and anticipate good lubrication performance 20 .…”

Section: Lubricant Fluidmentioning

confidence: 73%

“…Also, this chain is completely linear, without branches. Hence, this 2HEAPe longer anion chain was capable of stress dissipation, which reduced the coefficient of friction, as well as heteroatoms, capable of interacting with the metals 16,19,20,[60][61][62] , which aided to maintain the tribofilm in place along the experiment. 2HEAF, the PIL with the simplest structure and one carbon in the anion chain, could not reduce adhesion and yielded coefficient of friction similar as in the absence of lubricant in the ball-on-plate test, reflected in the impossibility to deform the aluminum 1100 as expected for the BUT test and in the stress concentration that provoked the rupture.…”

Section: Lubricant Fluidmentioning

confidence: 98%

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Protic Ionic Liquids Used as Metal-Forming Green Lubricants for Aluminum: Effect of Anion Chain Length

et al. 2017

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Among the applications for protic ionic liquids (PILs), lubrication is one of the newest and the most promising. In this work, ammonium-based protic ionic liquids were tested as lubricant fluids for aluminum-steel contacts. PILs were synthesized with 2-hydroxyethylamine (2HEA) and a carboxylic acid (formic and pentanoic), aiming to understand the effect of two different anion chain lengths on the lubricant behavior. The synthesized PILs were characterized by RMN, FTIR and TGA. Wear tests, conducted using a ball-on-plate configuration, showed that the increase of the anion carbon chain length in the PIL structure reduced significantly the coefficient of friction value. Besides, after the wear tests, the PILs structural integrity was not affected. In the same way, bending under tension (BUT) tests evidenced that the performance for stamping conditions of the PIL with the longest anion carbon chain was similar to that of the commercial lubricant. Since, both formed a uniform tribofilm, developed the same lubrication regime and the drawing forces values were close and constant. Hence, the ionic liquid obtained with 2HEA and pentanoic acid (2HEAPe) is as suitable as the commercial lubricant for metal forming processes.

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Section: Lubricant Fluidmentioning

confidence: 73%

Section: Lubricant Fluidmentioning

confidence: 98%

Protic Ionic Liquids Used as Metal-Forming Green Lubricants for Aluminum: Effect of Anion Chain Length

et al. 2017

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“…But they need some chemical treatment to overcome the oxidation instability (due to bis-allylic protons) as well the low temperature property issues. Cavalcante et al [31] mentioned that the oleic acid (C 18:1 ) content in the biodiesel, which is a monounsaturated fatty acid and abundantly found in both edible and non-edible sources, can be effectively used to produce biolubricants. Due to unsaturation quality, it is good in cold flow property but vulnerable to the oxidation stability.…”

Section: Vegetable Oil Based Lubricantsmentioning

confidence: 99%

Lubricity Improvement of the Ultra-low Sulfur Diesel Fuel with the Biodiesel

2015

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Ultra-low sulfur diesel fuel is essential requirement as per the emission regulation. With the adoption of hydrodesulfurization (HDS) process, the diesel fuel loses its inherent lubricity, however certain amount of lubricity of diesel fuel is needed to save several engine components from wear and failure. Though the loss of lubricity of the diesel fuel is observed with the removal of sulfur, it is mainly due to the loss of nitrogen and oxygen based polar trace compounds which are also removed in the HDS process. Unrefined biodiesels having little amount of monoglycerides (<0.8%) and free fatty acids also show better lubricity and fuel properties to be used as fuel lubricant. Biodiesel are also considered as the suitable blending compound with the diesel. This study found that the biodiesel blends up to 20% with the diesel fuel can effectively reduce both the wear of the tribo-contact surfaces as well as the friction coefficient. The use of biodegradable fuel lubricant has set away the threat of environment pollution by the diesel additives which are derived chemically. The oxidation stability and the low temperature properties of both the biodiesel and the vegetable oils can be improved with some chemical modification. It can be concluded that the use of biodiesel with the diesel fuel can be an appropriate option for effective engine lubrication system where only the fuel has to provide the required lubricity.

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“…They are used as: type II jet engine oils; hydraulic fluids and other lubricants for which biodegradable structures are required; as refrigeration lubricants due to their miscibility with hydrofluorcarbon (HFC) refrigerants; in air compressor oils and as components of hydrocarbon blends. They are also used in small amounts to help the solubilization of additives in formulations of base oils of polyalphaolefins (Cavalcante et al, ; Pirro et al, ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Novel Polyol Esters of Undecylenic Acid As Ecofriendly Lubricants

Cavalcante

Rocha

Brito

et al. 2018

J Americ Oil Chem Soc

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Three novel esters of undecylenic acid (UA) were synthesized using the following polyols: linear diglycerol (DG), pentaerythritol monomethylether (PEME), and trimethyloltoluene (TMT). They were characterized through density, viscosity, thermo-oxidative stability, melting point (m.p.), miscibility with mineral oils, and toxicity to evaluate their potential as ecofriendly lubricants. Trimethylolpropane (TMP) triundecylenate was also synthesized and characterized as a reference ester. Esters' densities were in the range 0.93-0.97 g cm −3 . The PEME ester showed a kinematic viscosity of 25.2 cSt at 40 C, only slightly higher than that of TMP ester (24.7 cSt), both of them near the ISO VG 22 class, while DG and TMT esters were near the ISO VG 32 class, with viscosities of 28.3 and 37.1 cSt, respectively. PEME and TMT esters were similar in thermo-oxidative stability and more stable than their corresponding oleate esters. The m.p. of TMT ester was remarkedly low (−54 C), showing its potential for very cold temperature applications. TMT ester was found to be nontoxic against Artemia salina (LC 50 > 1000 μg mL −1 ), an initial indication of nontoxicity of UA esters in aquatic media. The synthesized esters showed potential to be applied as ecofriendly lubricants.

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Synthesis and characterization of new esters of oleic acid and glycerol analogues as potential lubricants

Cited by 34 publications

References 33 publications

Protic Ionic Liquids Used as Metal-Forming Green Lubricants for Aluminum: Effect of Anion Chain Length

Protic Ionic Liquids Used as Metal-Forming Green Lubricants for Aluminum: Effect of Anion Chain Length

Lubricity Improvement of the Ultra-low Sulfur Diesel Fuel with the Biodiesel

Synthesis and Characterization of Novel Polyol Esters of Undecylenic Acid As Ecofriendly Lubricants

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