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

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

•Six new esters of oleic acid and polyols without β-hydrogen were synthesized.•Changes in the polyol structure generated esters with different flow properties.•The triesters had virtually the same thermo-oxidative stability of TMP trioleate.•Trimethyloltoluene trioleate showed the most interesting c...

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Bibliographic Details
Published in:Industrial crops and products Vol. 62; pp. 453 - 459
Main Authors: Cavalcante, Igor Marques, Rocha, Natália R. de C., Maier, Martin E., de Lima, Ana Paula Dantas, Andrade Neto, Davino M., de Brito, Débora Hellen A., Petzhold, César L., Schanz, Maria Telma G.F., Ricardo, Nágila M.P.S.
Format: Journal Article
Language:English
Published: Elsevier B.V 01-12-2014
Subjects:
Biolubricants
Esters
Ethers
Lubricants
Melting points
Neopentyl alcohols
Oleic acid
Polyols
Pour point
Stability
Thermogravimetric analysis
Viscosity
Biolubricants
Viscosity
Pour point
Thermogravimetric analysis
Neopentyl alcohols
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Summary:•Six new esters of oleic acid and polyols without β-hydrogen were synthesized.•Changes in the polyol structure generated esters with different flow properties.•The triesters had virtually the same thermo-oxidative stability of TMP trioleate.•Trimethyloltoluene trioleate showed the most interesting cold flow properties. A series of noncommercial polyols which do not contain β-hydrogen were used to synthesize new oleic acid based esters as potential thermally stable biolubricants. Commercial trimethylolpropane (TMP) was used to synthesize TMP trioleate as a reference polyol ester. The esters were purified by column chromatography and their structures were confirmed by 1H and 13C NMR and HRMS. The evaluated properties were kinematic viscosity, thermo-oxidative stability (by TGA) and melting point (m.p., by DSC). All the esters showed high viscosity indices (160–200) and similar thermo-oxidative stability (Tonset of triesters around 330°C), but a small change in the structure of the triols could generate esters of different viscosity grades (ISO VG 46 and 68) and different m.p. (ranging from −15 to −35°C). Two of the polyols generated triesters with virtually the same properties of TMP trioleate: pentaerythritil monoethyl ether (PEET) and pentaerythritil monobutyl ether (PEBUT). Two polyols must be highlighted: pentaerythritil monophenyl ether (PEPH) and trimethyloltoluene (TMT). PEPH generated an ISO VG 68 lubricant with a m.p. of −19°C, relatively low for this class, and TMT generated an ISO VG 68 lubricant with no defined melting peak, suggesting it has better cold temperature flow properties than TMP trioleate.
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ISSN:0926-6690
1872-633X
DOI:10.1016/j.indcrop.2014.08.022