Evaluation of Long-Chain Phosphorus Compounds as Lubricity Additives

Peale, Louise F.; Messina, Joseph; Ackerman, Bernard; Sasin, Richard; Swern, Daniel

doi:10.1080/05698196008972386

Cited by 13 publications

(10 citation statements)

References 3 publications

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“…There are reports in the literature that phosphonates act as antiwear additives in lubricating oils [2][3][4]. Improvement in the extreme pressure load and oxidative stability of lubricating oils in the presence of phosphonate additives has also been reported [4]. Phosphorus compounds are also added to plastics as flame retardants [5,6].…”

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confidence: 94%

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Synthesis and spectral characterization of methyl 9(10)-dialkylphosphonostearates

Bantchev

Biresaw

Vermillion

et al. 2013

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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mentioning

confidence: 94%

“…These compounds belong to the class of esters of the phosphonic acid, or dialkyl phosphonates. There are reports in the literature that phosphonates act as antiwear additives in lubricating oils [2][3][4]. Improvement in the extreme pressure load and oxidative stability of lubricating oils in the presence of phosphonate additives has also been reported [4].…”

mentioning

confidence: 95%

Synthesis and spectral characterization of methyl 9(10)-dialkylphosphonostearates

Bantchev

Biresaw

Vermillion

et al. 2013

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…Examination of the literature indicates that phosphonated oils have been investigated for their tribological properties by themselves [22][23][24][25][26][27] or in the presence of sulfur and/or halogen containing groups [28][29][30].…”

Section: Introductionmentioning

confidence: 99%

Tribological Properties of Biobased Ester Phosphonates

Biresaw¹,

Bantchev²

2013

J Americ Oil Chem Soc

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Three phosphonate derivatives of methyl oleate (MeO) were chemically synthesized in a radical chain reaction and their physical and tribological properties investigated. The phosphonates differed from each other in the structure of the alkoxy groups attached to the phosphorous, which were as follows: methoxy, ethoxy, and n-butoxy. Phosphonylation eliminated the unsaturation in MeO and also introduced branching. The phosphonate oils had higher density and viscosity than MeO, which was attributed to the contribution of the heavier phosphorus atom in their structures, and to their higher molecular weights, respectively. The phosphonates also displayed improved oxidation stability and cold flow properties, which were attributed to the elimination of the double bond and the introduction of branching in their molecular structures, respectively. Tribological investigations were conducted using 4-Ball anti-wear (AW) and extreme pressure (EP) methods. Neat phosphonates displayed lower AW coefficients of friction and wear scar diameters than MeO. The improved AW results were attributed to the higher viscosity of the phosphonates, since the AW test is conducted in the mixed film regime. The phosphonates had no effect on EP weld point (WP) as neat oils or as 5 % additives in petroleum-based oils. In soy base oil, 5 % phosphonate additives displayed smaller improvement in WP than zinc dialkyl dithiophosphate (ZDDP). It is proposed that this lack of EP characteristics could be due to the high dissociation energy of C-P bonds in the phosphonates, compared to, for example, S-P bonds in ZDDP.

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“…Wear-test data were obtained by means of the Precision Shell Four-Ball Wear Test according to the procedure described by Peale et al (5).…”

Section: Testing Proceduresmentioning

confidence: 99%

Nonvolatilealpha‐branched chain fatty esters. II

Bilyk

Eisner

Ault

1968

J Americ Oil Chem Soc

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A group of nonvolatile alpha-branched esters was prepared by the di-tertiary butyl peroxidepromoted addition of normal esters to terminal olefins containing methyl branches or aryl groups. Methyl stearate was added to 3,7-dimcthyl-1octene, 3,5,5-trimethy]-l-hexene, and 4-phenyl-1butene. The reaction with 2,4,4-trimethyl-1pentene, a terminal alkene with a methyl branch at the internal ethylenic carbon, was not successful. Benzyl 2-(4-phenylbutyl)octadecanoate was prepared by transesterification of the corresponding methyl ester. Benzyl 2,2-dimethylpropanoate, which has no a-hydrogen in the aeyl portion of the molecule, was added to 1-hexadecene to form ~-hexadecylbenzyl 2,2-dimethylpropanoate. Lubricant evaluation data were obtained on the above compounds.

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Evaluation of Long-Chain Phosphorus Compounds as Lubricity Additives

Cited by 13 publications

References 3 publications

Synthesis and spectral characterization of methyl 9(10)-dialkylphosphonostearates

Synthesis and spectral characterization of methyl 9(10)-dialkylphosphonostearates

Tribological Properties of Biobased Ester Phosphonates

Nonvolatilealpha‐branched chain fatty esters. II

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