Viscosity Characteristics of Long-Chain Phosphorus Compounds.

Swern, Daniel; Palm, W. E.; Sasin, Richard; Witnauer, Lee P.

doi:10.1021/je60008a021

Cited by 14 publications

(9 citation statements)

References 2 publications

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“…The analysis of the data showed that the 9-position isomers (a) eluted first for all the compounds in this paper (6)(7)(8)(9)(10)(11). The strongest peak for compounds 6-9 can be explained with a rearrangement that leads to a loss of fragments CH 2 COOR and C 9 H 18 (for 9-position isomers) or C 8 H 16 (for 10-position isomers).…”

Section: Gc-ms Spectramentioning

confidence: 69%

“…This work (6) This work (9) This work (7) Opper et al [13,14] Scheme 4. Compounds with reported NMR spectra [13][14][15], whose atom connections around the P atom are similar to those of 6-9 in this work (see Fig.…”

Section: Ft-irmentioning

confidence: 99%

“…The compounds are reported to have low pour points (À50 to À65°C) [9] and to be good plasticizers for polyvinylchloride [10]. However, these compounds were not fully characterized and lacked assignments by modern techniques (NMR and MS).…”

mentioning

confidence: 99%

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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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Section: Gc-ms Spectramentioning

confidence: 69%

Section: Ft-irmentioning

confidence: 99%

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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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“…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%

“…Swern et al [23] synthetized a series of P,P-dialkyl 9(10)-phosphonostearates and reported its viscosity, viscosity index, and cold flow properties.…”

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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2 Pure Compounds: Data

Wohlfarth¹,

Wohlfahrt²

Pure Organometallic and Organononmetallic Liquids, Binary Liquid Mixtures

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Viscosity Characteristics of Long-Chain Phosphorus Compounds.

Cited by 14 publications

References 2 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

2 Pure Compounds: Data

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