Soybean oil as a renewable feedstock for nitrogen-containing derivatives

Biswas, Atanu; Sharma, Brajendra K.; Willett, J. L.; Erhan, Sevim Z.; Cheng, H. N.

doi:10.1039/b809215j

Cited by 54 publications

(30 citation statements)

References 33 publications

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“…A number of approaches are under active development in order to remedy these and other serious shortcomings of vegetable oils for lubrication applications. One of the methods that is widely pursued to improve the performance of biobased oils in lubrication is by chemical modification [1][2][3][4][13][14][15][16][17][18][19][20]. Vegetable oils and their derivatives are subjected to various types of chemical modification to improve a variety of properties or to impart to them new properties and produce value-added oils.…”

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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Section: Introductionmentioning

confidence: 99%

Tribological Properties of Biobased Ester Phosphonates

Biresaw¹,

Bantchev²

2013

J Americ Oil Chem Soc

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“…Fatty amines: Fatty amines, obtained from fatty acids or fatty acid alkyl esters by reaction with ammonia at a high temperature followed by dehydration and hydrogenation, are used in the lubricant industry as a friction modifier in engine oils [101,102]. The preparation of fatty amines occurs in two steps ( Figure 5).…”

Section: Hydrolysismentioning

confidence: 99%

Chemically Modifying Vegetable Oils to Prepare Green Lubricants

2017

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Chemically modifying vegetable oils to produce an alternative to petroleum-based materials is one of the most important emerging industrial research areas today because of the adverse effects of petroleum products on the environment and the shortage of petroleum resources. Biolubricants, bioplasticizers, non-isocyanate polyurethanes, biofuel, coating materials, biocomposites, and other value-added chemicals can easily be produced by chemically modifying vegetable oils. This short review discusses using vegetable oils or their derivatives to prepare lubricants that are environmentally safe. Chemically modified vegetable oils are generally used as base fluids to formulate environmentally friendly lubricants. Reports of their application as sustainable additives have attracted special attention recently because of their enhanced multifunctional performances (single additives perform several functions, i.e., viscosity index improver, pour point depressant, antiwear products) and biodegradability compared with commercial additives. Here, we have reviewed the use of chemically modified vegetable oils as base fluids and additives to prepare a cost-effective and environmentally friendly lubricant composition.

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“…Applications include lubricants (12), paints, coatings, and adhesives (13,14), plastics (15,16), and biomedical materials (13). Several recent review articles are available (12)(13)(14)(15)(16)(17)(18).…”

Section: Introductionmentioning

confidence: 98%

Modifications of Plant Oils for Value-Added Uses

Cheng

Biswas

2015

ACS Symposium Series

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Plant oils are valuable agricultural commodities and useful raw materials for the preparation of value-added products. In this article, a review is made of the various structural modifications made on plant oils in the authors' laboratories. The reactions include Diels-Alder, ene reaction, transesterification, acid or enzymatic hydrolysis, heat-bodying reaction, hydrogenation, epoxidation, formation of acetonide, aminohydrin, and azidohydrin, click reaction, and polymerization. A wide range of products have been made from plant oils and their epoxidized derivatives.Many of these reaction pathways produce new triglyceride structures not previously reported. The properties of selected products have been tested, particularly in lubricant applications to enhance viscosity, thermal stability, or mechanical wear.

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Soybean oil as a renewable feedstock for nitrogen-containing derivatives

Cited by 54 publications

References 33 publications

Tribological Properties of Biobased Ester Phosphonates

Tribological Properties of Biobased Ester Phosphonates

Chemically Modifying Vegetable Oils to Prepare Green Lubricants

Modifications of Plant Oils for Value-Added Uses

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