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- Author:
- Shoyeb Khan; Probir Das; Mohammed Abdul Quadir; Mahmoud Thaher; Senthil Nagappan Annamalai; Chandan Mahata; Alaa H. Hawari; Hareb Al Jabri
- Source:
- Science of the total environment 2022 v.847 pp. 157648
- ISSN:
- 0048-9697
- Subject:
- estolides, etc ; Jatropha; biolubricants; biomass; biorefining; environment; epoxidation reactions; feedstocks; microalgae; oils; oxidative stability; pour point; viscosity; Show all 13 Subjects
- Abstract:
- ... Several edible and non-edible oil sources are currently being developed as renewable basestocks for biolubricant production. However, these feedstocks possess undesirable physicochemical properties limiting their lubricant applications. Chemical modification and additive-based routes could be used to modify their properties -suitable for different biolubricant applications. The first part of this ...
- DOI:
- 10.1016/j.scitotenv.2022.157648
- https://doi.org/10.1016/j.scitotenv.2022.157648
- Author:
- Bantchev Grigor B.; Cermak Steven C.
- Source:
- Fuel 2022 v.309 no. pp. -
- ISSN:
- 0016-2361
- Subject:
- estolides, etc ; molecular weight; prediction; temperature; uncertainty; viscosity; Show all 6 Subjects
- Abstract:
- ... Estolides are a relatively new class of biobased materials, and their properties are not thoroughly investigated. Since they have been recently commercialized as lubricants, a deeper investigation of their viscosity was warranted. Five 3-parameter viscosity models with theoretical derivations were found in the literature. Additionally, several empirical 2- and 3-parameter models, including one emp ...
- Handle:
- 10113/7553987
- DOI:
- 10.1016/j.fuel.2021.122190
- CHORUS:
- 10.1016/j.fuel.2021.122190
- https://doi.org/10.1016/j.fuel.2021.122190
- Author:
- Girma Biresaw; Yunzhi Chen; Li Chen; Helen Ngo; Karen Wagner; Karl E. Vermillion; Steven C. Cermak
- Source:
- Industrial crops and products 2022 v.182 pp. 114857
- ISSN:
- 0926-6690
- Subject:
- estolides, etc ; biolubricants; carbon; cold; oxidative stability; pour point; temperature; vegetables; viscosity; Show all 9 Subjects
- Abstract:
- ... One of the drawbacks of using vegetable oils directly as a lubricant is poor low temperature performance, mainly pour and cloud points. Oleic estolides were developed to improve these properties as well as increase the oxidative stability of the oil. However, additional low temperature properties are desirable to increase the field of use of these materials. A new series of iso-oleic estolide free ...
- DOI:
- 10.1016/j.indcrop.2022.114857
- https://doi.org/10.1016/j.indcrop.2022.114857
- Author:
- Kristyna Brejchova; Veronika Paluchova; Marie Brezinova; Tomas Cajka; Laurence Balas; Thierry Durand; Marcela Krizova; Zbynek Stranak; Ondrej Kuda
- Source:
- Food chemistry 2022 v.388 pp. 132983
- ISSN:
- 0308-8146
- Subject:
- estolides, etc ; breast milk; carboxylic ester hydrolases; case-control studies; cesarean section; colostrum; food chemistry; inflammation; intestines; lactation; lipidomics; milk; palmitic acid; premature birth; triacylglycerols; Show all 15 Subjects
- Abstract:
- ... Breast milk is a complex mixture containing underexplored bioactive lipids. We performed an observational case-control study to compare the impact of delivery mode: caesarean section (CS) and vaginal birth (VB); and term (preterm and term delivery) on the levels of lipokines in human milk at different stages of lactation. Metabolomic analysis of the milk identified triacylglycerol estolides as a m ...
- DOI:
- 10.1016/j.foodchem.2022.132983
- https://doi.org/10.1016/j.foodchem.2022.132983
- Author:
- Grigor B. Bantchev; Steven C. Cermak; Amber L. Durham; Neil P. J. Price
- Source:
- The journal of the American Oil Chemists' Society 2019 v.96 no.4 pp. 365-380
- ISSN:
- 0003-021X
- Subject:
- estolides, etc ; equations; gel chromatography; molecular weight; oleic acid; tetrahydrofuran; Show all 6 Subjects
- Abstract:
- ... Using the universal calibration and the Mark‐Houwink equation (MHE) (ηj=KMjα), three batches of oleic estolide acids and their corresponding 2‐ethylhexyl esters were characterized using gel permeation chromatography (GPC). The MHE parameters in tetrahydrofuran (THF) at 40 °C were determined (for acids: α = 0.442 ± 0.003 and log₁₀K=2.505 ± 0.007, for esters: α =0.531 ± 0.006 and log₁₀K =2.794 ± 0.0 ...
- Handle:
- 10113/6896870
- DOI:
- 10.1002/aocs.12165
- https://doi.org/10.1002/aocs.12165
- Author:
- Yunzhi Chen; Girma Biresaw; Steven C. Cermak; Terry A. Isbell; Helen L. Ngo; Li Chen; Amber L. Durham
- Source:
- The journal of the American Oil Chemists' Society 2020 v.97 no.3 pp. 231-241
- ISSN:
- 0003-021X
- Subject:
- estolides, etc ; Physaria; biodegradability; biolubricants; carboxylic ester hydrolases; catalysts; coconuts; cold; cosmetics; fatty acids; petroleum; pour point; temperature; vegetables; viscosity; Show all 15 Subjects
- Abstract:
- ... Estolides are bio‐based oils synthesized from fatty acids or from the reaction of fatty acids with vegetable oils. Estolides have many advantages as lubricant base oils, including excellent biodegradability and cold flow properties. Promising applications for estolides include bio‐lubricant base oils and in cosmetics. In this review, the synthesis of estolides from fatty acids using four different ...
- DOI:
- 10.1002/aocs.12323
- https://doi.org/10.1002/aocs.12323
7. Synthesis of Estolide Ester and Amide from Acetylated Polyhydroxy Estolide for Lubricant Base Oil
- Author:
- Seng Soi Hoong; Mohd Zan Arniza; Nek Mat Din Nik Siti Mariam; Abu Hassan Noor Armylisas; Siti Afida Ishak; Tuan Noor Maznee Tuan Ismail; Shoot Kian Yeong
- Source:
- European journal of lipid science and technology 2020 v.122 no.10 pp. e2000098
- ISSN:
- 1438-7697
- Subject:
- estolides, etc ; acetic acid; alcohols; biodegradability; biolubricants; dodecanoic acid; hydrogen peroxide; markets; oils; oleic acid; oxidative stability; petroleum; pour point; technology; viscosity; Show all 15 Subjects
- Abstract:
- ... Plant oil‐based lubricants are used as alternative for mainstream petroleum‐based lubricants mainly because they are known to be environmentally friendly. However, their market acceptance is limited by their high pour point and poor oxidation stability. This study presents an approach to make biodegradable lubricant from oleic acid that shows low pour point and satisfactory oxidation stability. A ...
- DOI:
- 10.1002/ejlt.202000098
- https://doi.org/10.1002/ejlt.202000098
- Author:
- Lucas J. Stolp; Michael Grass; Dharma R. Kodali
- Source:
- The journal of the American Oil Chemists' Society 2021 v.98 no.3 pp. 297-304
- ISSN:
- 0003-021X
- Subject:
- estolides, etc ; acetic anhydride; acetylation; butanol; castor oil; epoxides; fatty acid esters; fatty acids; gelation; humidity; leather; methanol; phthalates; plasticizers; temperature; viscosity; Show all 16 Subjects
- Abstract:
- ... Epoxy fatty acid alkyl ester estolides were synthesized from castor oil to be used as biobased plasticizers for poly(vinyl chloride) (PVC) as a safer replacement for phthalate plasticizers. Initially, castor oil was transesterified with methanol or n‐butanol to quantitatively yield castor fatty acid alkyl esters. Acetylation of hydroxyl function with acetic anhydride led to the formation of estoli ...
- DOI:
- 10.1002/aocs.12462
- https://doi.org/10.1002/aocs.12462
- Author:
- Lucas Natã de Melo; Letícia Amaral Santana; Paulo Felisberto da Rocha; Simoni Margareti Plentz Meneghetti; Mario Roberto Meneghetti; Janaína Heberle Bortoluzzi
- Source:
- Energy & fuels 2020 v.34 no.5 pp. 5948-5957
- ISSN:
- 1520-5029
- Subject:
- estolides, etc ; alcoholysis; castor oil; catalysts; coconut oil; energy; esterification; fatty acid composition; moieties; nuclear magnetic resonance spectroscopy; potassium; sodium hydroxide; soybean oil; transesterification; triacylglycerols; viscosity; Show all 16 Subjects
- Abstract:
- ... In this work, studies of the transesterification using sodium hydroxide as a catalyst of mixtures of soybean oil/coconut oil (SO/CNO) and soybean oil/castor oil (SO/CO) before and after interesterification (in the presence of potassium methoxide as a catalyst) are presented. To the best of our knowledge, studies comparing raw materials from different sources to the same fatty acid composition have ...
- DOI:
- 10.1021/acs.energyfuels.0c00291
- https://doi.org/10.1021/acs.energyfuels.0c00291
- Author:
- Lucas J. Stolp; Patrick J. Gronlund; Dharma R. Kodali
- Source:
- The journal of the American Oil Chemists' Society 2019 v.96 no.6 pp. 727-738
- ISSN:
- 0003-021X
- Subject:
- estolides, etc ; acetates; fatty acid esters; fatty acids; glass transition temperature; glycerol; methanol; molecular weight; plasticizers; soybean oil; Show all 10 Subjects
- Abstract:
- ... Fatty acid ester estolides were synthesized from soybean oil and evaluated for plasticizer functionality in poly(vinyl chloride) (PVC). The plasticization ability of the fatty acid ester estolides depends upon the molecular features such as polarity, molecular weight, and branching. The structure of the fatty acid derivatives was modified at the ester head group with various alcohols and the estol ...
- DOI:
- 10.1002/aocs.12214
- https://doi.org/10.1002/aocs.12214
- Author:
- Isbell Terry A.; Benjamin A. Lowery; Karl Vermillion; Steven C. Cermak
- Source:
- journal of the American Oil Chemists' Society 2020 v.97 no.4 pp. 409-423
- ISSN:
- 0003-021X
- Subject:
- estolides, etc ; catalysts; dodecanoic acid; epoxides; hydrolysis; nuclear magnetic resonance spectroscopy; oils; olefin; oleic acid; perchloric acid; polyethylene glycol; tin; Show all 12 Subjects
- Abstract:
- ... Estolides from oleic acid, 12‐hydroxystearic acid, and methyl ricinoleate were synthesized and converted to polyethylene glycol (PEG) diesters. Oleic estolide was synthesized from oleic acid as a homo‐oligomeric material using perchloric acid in 68.8% yield and an estolide number (EN) value of 1.29. Estolides from 12‐hydroxystearic acid were homo‐oligomers made by heating under vacuum at 150 °C fo ...
- Handle:
- 10113/6937368
- DOI:
- 10.1002/aocs.12336
- https://doi.org/10.1002/aocs.12336
- Author:
- Luigi di Bitonto; Stefano Todisco; Vito Gallo; Carlo Pastore
- Source:
- Bioresource technology reports 2020 v.9 pp. 100382
- ISSN:
- 2589-014X
- Subject:
- estolides, etc ; biodiesel; biolubricants; calcium; enantiomers; feasibility studies; free fatty acids; lipids; methanol; sewage; sludge; soaps; total solids; wastewater treatment; Show all 14 Subjects
- Abstract:
- ... Lipids of sewage scum and primary sludge taken from several wastewater treatment plants were quantified and characterised. In sewage scum, lipids represented 36–50% of total solids and were primarily composed of free fatty acids (45–60%) and calcium soaps (27–35%). In primary sludge, total lipids were 20–24% of total solids, and 71–82% of these were calcium soaps. Estolides and 10-hydroxystearic a ...
- DOI:
- 10.1016/j.biteb.2020.100382
- https://doi.org/10.1016/j.biteb.2020.100382
- Author:
- Terry A. Isbell; Benjamin A. Lowery; Steven C. Cermak
- Source:
- The journal of the American Oil Chemists' Society 2020 v.97 no.4 pp. 425-435
- ISSN:
- 0003-021X
- Subject:
- estolides, etc ; epoxides; hydrogen bonding; moieties; molecular weight; oils; oleic acid; petroleum; polyethylene glycol; ricinoleic acid; solubility; stearic acid; vegetables; viscometry; viscosity; Show all 15 Subjects
- Abstract:
- ... Polyethylene glycol (PEG) diesters from estolides of oleic acid, ricinoleic acid, and 12‐hydroxy stearic acid were used up to 5 wt% additive in petroleum‐derived base oils: 100 N, 220 N, 600 N, PAO 2cSt, PAO 4cst, and PAO 8cSt. The viscosity indices of the petroleum base oils were the lowest (VI = 104–108); the polyalpholefin (PAO) synthetic petroleum‐derived base oils were better (VI = 124–136) a ...
- Handle:
- 10113/7019768
- DOI:
- 10.1002/aocs.12334
- https://doi.org/10.1002/aocs.12334
- Author:
- Sylwia Dworakowska; Cédric Le Coz; Guillaume Chollet; Etienne Grau; Henri Cramail
- Source:
- European journal of lipid science and technology 2019 v.121 no.11 pp. e1900264
- ISSN:
- 1438-7697
- Subject:
- estolides, etc ; biomass; catalysts; crosslinking; differential scanning calorimetry; esterification; fatty acids; glass transition temperature; molecular weight; polyesters; sulfur; tensile strength; thermal stability; thermogravimetry; titanium; vegetables; Show all 16 Subjects
- Abstract:
- ... This study aims at obtaining cross‐linked polymeric materials of biomass origin. For this purpose, one‐pot polyesterification of methyl ricinoleate and methyl 12‐hydroxystearate using titanium isopropoxide as a catalyst is performed leading to polyesters known as estolides. The obtained estolides are successfully cross‐linked using dicumyl peroxide or a sulfur vulcanization system. The so‐formed b ...
- DOI:
- 10.1002/ejlt.201900264
- https://doi.org/10.1002/ejlt.201900264
- Author:
- Agnes Fröscher; Kai Langenbach; Erik von Harbou; Werner R. Thiel; Hans Hasse
- Source:
- Industrial & engineering chemistry process design and development 2019 v.58 no.14 pp. 5622-5630
- ISSN:
- 1520-5045
- Subject:
- estolides, etc ; biopolymers; catalysts; chemical equilibrium; chemical reactions; elaidic acid; formic acid; nuclear magnetic resonance spectroscopy; oleic acid; process design; renewable resources; spectral analysis; temperature; thermodynamics; Show all 14 Subjects
- Abstract:
- ... Oleic acid (OA) and formic acid (FA) react to formoxystearic acid (FSA), in the presence of acidic catalysts. This reaction is of interest as OA can be obtained from renewable resources and FSA is a potential precursor for biopolymers. We have recently studied the liquid–liquid equilibrium (LLE) in the uncatalyzed nonreacting system OA + FA + FSA. This work is extended here to the reactive system, ...
- DOI:
- 10.1021/acs.iecr.8b05715
- https://doi.org/10.1021/acs.iecr.8b05715
- Author:
- Lucas J. Stolp; Eugene Joseph; Dharma R. Kodali
- Source:
- The journal of the American Oil Chemists' Society 2019 v.96 no.11 pp. 1291-1302
- ISSN:
- 0003-021X
- Subject:
- estolides, etc ; acetates; acetic acid; acetylation; crosslinking; fatty acid methyl esters; glass transition temperature; glycerol; industry; methanol; molecular weight; oleic acid; phthalates; polyunsaturated fatty acids; soybean oil; tetrahydrofuran; Show all 16 Subjects
- Abstract:
- ... Plasticizers are nonvolatile organic liquids that impart flexibility to polymers. Due to environmental, health, and safety reasons, the industry is looking for bioplasticizers to replace petroleum‐derived phthalates. To fulfill this need, soy fatty acid ester estolides were synthesized, characterized, and evaluated as phthalate replacements. Soybean oil was transesterified with methanol or glycero ...
- DOI:
- 10.1002/aocs.12279
- https://doi.org/10.1002/aocs.12279
17. Derivatization of castor oil based estolide esters: Preparation of epoxides and cyclic carbonates
- Author:
- Kenneth M. Doll; Steven C. Cermak; James A. Kenar; Erin L. Walter; Terry A. Isbell
- Source:
- Industrial crops and products 2017 v.104 pp. 269-277
- ISSN:
- 0926-6690
- Subject:
- estolides, etc ; carbon dioxide; carbonates; castor oil; derivatization; epoxides; hydrogen peroxide; industrial applications; oleic acid; oxidation; temperature; tetrabutylammonium compounds; viscosity; Show all 13 Subjects
- Abstract:
- ... Estolides that are based on castor oil and oleic acid are versatile starting points for the production of industrial fluids with new properties. A variety of unsaturated estolides were derivatized by epoxidation with hydrogen peroxide. The epoxidized estolides were further modified using supercritical carbon dioxide and tetrabutylammonium bromide to chemically incorporate carbon dioxide into the m ...
- Handle:
- 10113/5684918
- DOI:
- 10.1016/j.indcrop.2017.04.061
- https://doi.org/10.1016/j.indcrop.2017.04.061
18. Synthesis and physical properties of novel estolides from dicarboxylic acids and methyl ricinoleate
- Author:
- Arukali Sammaiah; Korlipara V. Padmaja; Rachapudi B.N. Prasad
- Source:
- European journal of lipid science and technology 2016 v.118 no.3 pp. 486-494
- ISSN:
- 1438-7697
- Subject:
- estolides, etc ; biolubricants; castor oil; dicarboxylic acids; esterification; feedstocks; ricinoleic acid; solvents; temperature; thermal stability; vegetable oil; viscosity; Show all 12 Subjects
- Abstract:
- ... Castor oil is an attractive feedstock for the preparation of a variety of industrially important products due to the presence of ricinoleic acid with hydroxyl functionality up to 85–90%. Methyl ricinoleate was esterified with different dicarboxylic acids to prepare a series of a new class of estolides under solvent and catalyst‐free conditions. The products were evaluated for their physico‐chemica ...
- DOI:
- 10.1002/ejlt.201500109
- https://doi.org/10.1002/ejlt.201500109
- Author:
- Juan Carlos de Haro; Maria del Prado Garrido; Ángel Pérez; Manuel Carmona; Juan Francisco Rodríguez
- Source:
- Journal of cleaner production 2018 v.184 pp. 579-585
- ISSN:
- 0959-6526
- Subject:
- estolides, etc ; biodiesel; biolubricants; biosurfactants; choline; distillation; esterification; free fatty acids; industrial applications; ionic liquids; methanol; neutralization; oleic acid; perchloric acid; raw materials; value-added products; Show all 16 Subjects
- Abstract:
- ... A new three step process has been developed and optimized in order to demonstrate that is possible to get complete conversion of free fatty acids (FFA) into estolide esters (biolubricant), biodiesel and choline carboxylates (biosurfactants). This new approach consists in the utilization of HClO₄, a cheap and industrially available strong acid, to generate the estolides followed by an esterificatio ...
- DOI:
- 10.1016/j.jclepro.2018.02.190
- https://doi.org/10.1016/j.jclepro.2018.02.190
- Author:
- Jiann-Tsyh Lin; Grace Q. Chen
- Source:
- Biocatalysis and agricultural biotechnology 2017 v.10 pp. 167-173
- ISSN:
- 1878-8181
- Subject:
- estolides, etc ; Physaria fendleri; biodegradability; biotechnology; electrospray ionization mass spectrometry; fatty acids; glycerol; high performance liquid chromatography; industry; lithium; lubricants; pour point; seed oils; triacylglycerols; viscosity; Show all 15 Subjects
- Abstract:
- ... Tetraacylglycerols (triacylglycerol estolides) contain an acylacyl chain (one fatty acid attached to the hydroxyl group of another fatty acid attached to the glycerol backbone) and have different physical properties from those of triacylglycerols. Tetraacylglycerols can be used in industry such as the viscosity improver and pour point depressant of lubricants. The structures, contents and the rati ...
- DOI:
- 10.1016/j.bcab.2017.03.005
- https://doi.org/10.1016/j.bcab.2017.03.005
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