Epoxidation of Vegetable Oils, Unsaturated Fatty Acids and Fatty Acid Esters: A Review

2020 ◽  
Vol 17 (4) ◽  
pp. 412-422
Author(s):  
Grzegorz Lewandowski ◽  
Marlena Musik ◽  
Kornelia Malarczyk-Matusiak ◽  
Łukasz Sałaciński ◽  
Eugeniusz Milchert
Keyword(s):  
Fatty Acids ◽  
Vegetable Oils ◽  
Unsaturated Fatty Acids ◽  
Fatty Acid Esters ◽  
Performic Acid ◽  
Molar Ratio ◽  
Technological Parameters ◽  
Acidic Catalysts ◽  
Acid Esters

A comprehensive review of recent existing methods of epoxidation of vegetable oils, unsaturated fatty acids and alkyl esters of unsaturated fatty acids has been presented. The importance of epoxidized vegetable oils and their applications in the production of polyols and polyurethanes was discussed. Interests of researchers have been mainly focused on the development of advantageous technological parameters of vegetable oils epoxidation. The epoxidations with peracetic acid or performic acid generated in situ were mainly performed in the presence of strongly acidic catalysts. The influence of process variables such as temperature, stirring speed, the molar ratio of carboxylic acid and hydrogen peroxide to the amount of ethylenic unsaturation, amount of catalyst and reaction time on the course of epoxidation has been investigated.

In situ alkaline transesterification: An effective method for the production of fatty acid esters from vegetable oils

2004 ◽  
Vol 81 (1) ◽  
pp. 83-89 ◽  
Author(s):  
Michael J. Haas ◽  
Karen M. Scott ◽  
William N. Marmer ◽  
Thomas A. Foglia
Keyword(s):  
Fatty Acid ◽  
Vegetable Oils ◽  
Fatty Acid Esters ◽  
Acid Esters

Constituents of some Curvularia species

1968 ◽  
Vol 21 (3) ◽  
pp. 783 ◽  
Author(s):  
RG Coombe ◽  
JJ Jacobs ◽  
TR Watson
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Related Species ◽  
Unsaturated Fatty Acids ◽  
Brefeldin A ◽  
Fatty Acid Esters ◽  
Curvularia Species ◽  
Acid Esters

Thirteen Gurvularia and related species were examined and the following metabolites obtained: brefeldin A, curvularin, curvulin, curvulinic acid derivatives, D-mannitol, 1,4,5,8-tetrahydroxy-2,6-dimethylanthraquinone, saturated and unsaturated fatty acids, and fatty acid esters.

Stimulation of Phosphorylcholine–Glyceride Transferase Activity by Unsaturated Fatty Acids

1973 ◽  
Vol 51 (11) ◽  
pp. 1479-1486 ◽  
Author(s):  
Michael Sribney ◽  
Eileen M. Lyman
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Unsaturated Fatty Acids ◽  
Small Extent ◽  
Fatty Acid Esters ◽  
Transferase Activity ◽  
Significant Extent ◽  
Acyltransferase Activity ◽  
Acid Esters ◽  
Stimulation Of

A number of unsaturated fatty acids markedly stimulate chicken liver microsomal phosphorylcholine–glyceride transferase (CDP-choline:1,2-diglyceride cholinephosphotransferase, EC 2.7.8.2). Oleate (0.8 mM) activates this enzyme severalfold only if a mixed diglyceride such as 1-palmitoyl-2-oleoyl-sn-glycerol is used as a substrate for the reaction. Dipalmitin and diolein incorporation into lecithin is not stimulated to any significant extent by unsaturated fatty acids. Fatty acid esters and numerous detergents either inhibit the enzyme or have no effect. Phosphorylethanolamine–glyceride transferase (CDP-ethanolamine:1,2-diglyceride ethanolaminephosphotransferase, EC 2.7.8.1) activity is only very slightly stimulated while diglyceride O-acyltransferase activity is inhibited to a small extent.

scholarly journals Technological Aspects of Chemoenzymatic Epoxidation of Fatty Acids, Fatty Acid Esters and Vegetable Oils: A Review

Molecules ◽  
2015 ◽  
Vol 20 (12) ◽  
pp. 21481-21493 ◽  
Author(s):  
Eugeniusz Milchert ◽  
Kornelia Malarczyk ◽  
Marlena Kłos
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Vegetable Oils ◽  
Fatty Acid Esters ◽  
Acid Esters

The Use of Argentation Chromatography for the Analysis of Fatty Acid Esters of Polyenes: The Structure of Carotenoid Esters of Aglais urticae (Lepidoptera, Insecta)

1975 ◽  
Vol 30 (5-6) ◽  
pp. 369-378 ◽  
Author(s):  
Hartmut Kayser
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Unsaturated Fatty Acids ◽  
Reversed Phase ◽  
Fatty Acid Esters ◽  
Preparative Scale ◽  
Argentation Chromatography ◽  
Acid Esters

Abstract Argentation Thin-layer systems for argentation chromatography of fatty-acid esters of carotenoids have been developed. As two-dimensional reversed-phase partition system on paraffine impregnated cellulose this method permits a clear discrimination between saturated and unsaturated fatty acids. By adsorption on silver nitrate containing silica gel-G separation of carotenoid esters according to the degree of unsaturation of their fatty acids was established. With the use of known esters for comparison the fatty acids of whole carotenoid esters can be successfully analysed from minute amounts. Using these methods the carotenoid esters of pupae of Aglais urticae have been studied. The pupae contain 5.3% β-carotene, 46% lutein diester, 7.8% lutein 3-monoester, 11.7% lutein 3′-mono-ester, and 29.2% unesterified lutein. The fatty acids of the esters are linoleic acid (18:2) and linolenic acid (18:3) only. The diester fraction was composed of 70% dilinolenate, 25% linolenate-linoleate, and 5% dilinoleate. The combined monoesters consisted of 81% linolenate and 19% linoleate. The two main diesters could be isolated in a preparative scale and their structure verified by mass spectrometry. On the whole, in Aglais pupae 6.2 μg linolenic acid and 1.4 μg linoleic acid are bound to lutein. Since polyunsaturated fatty acids are of dietary origin, and represent essential factors for insect development, it is concluded, that their esterification with carotenoids may be a mode of storage comparable to the formation of glycerides.

scholarly journals Technological aspects of vegetable oils epoxidation in the presence of ion exchange resins: a review

2016 ◽  
Vol 18 (3) ◽  
pp. 128-133 ◽  
Author(s):  
Eugeniusz Milchert ◽  
Kornelia Malarczyk-Matusiak ◽  
Marlena Musik
Keyword(s):  
Ion Exchange ◽  
Vegetable Oils ◽  
Review Paper ◽  
Performic Acid ◽  
Molar Ratio ◽  
Catalyst Loading ◽  
Ion Exchange Resins ◽  
Technological Parameters ◽  
Catalyst Recycling ◽  
Exchange Resins

Abstract A review paper of the technology basics of vegetable oils epoxidation by means of peracetic or performic acid in the presence of acidic ion exchange resins has been presented. The influence of the following parameters: temperature, molar ratio of acetic acid and hydrogen peroxide to ethylenic unsaturation, catalyst loading, stirring intensity and the reaction time on a conversion of ethylenic unsaturation, the relative percentage conversion to oxirane and the iodine number was discussed. Optimal technological parameters, mechanism of epoxidation by carboxylic peracids and the possibilities of catalyst recycling have been also discussed. This review paper shows the application of epoxidized oils.

scholarly journals Fatty acids in wild hemp seeds (Cannabis sativa L. ssp. sativa var. spontanea Vavilov)

2021 ◽  
Vol 30 (1) ◽  
pp. 65-73
Author(s):  
Bojana Špirović-Trifunović ◽  
Dejan Nedeljković ◽  
Darko Stojićević ◽  
Dragana Božić
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Unsaturated Fatty Acids ◽  
Cannabis Sativa ◽  
Folk Medicine ◽  
Raw Material ◽  
Fatty Acid Esters ◽  
Relative Mass ◽  
Industrial Hemp ◽  
Acid Esters

Wild hemp (Cannabis sativa L. ssp. sativa var. spontanea) is a special variety of industrial hemp (Cannabis sativa L. ssp. sativa), which is believed to have originated from the acclimatization of industrial hemp to the ruderal habitat conditions of Eastern Europe. In Serbia it is found along roads, on field edges, stubble fields, garbage dumps etc., but also as a weed in fields. Due to the great popularity of industrial hemp, which can be used for various purposes (as raw material in food and pharmaceutical industry, in the production of gluten-free flour, biodiesel, detergents, in folk medicine), many researchers have analyzed its seeds, including analysing their fatty acids content. However, even though this knowledge can be of chemotaxonomic, ecological, evolutionary and nutritional significance, there is no data on the presence and composition of fatty acids in wild hemp seeds For the analysis of fatty acids in wild hemp seeds, the seed material was collected from two locations. After the extraction with hexane, determination of fatty acid esters was performed by capillary gas chromatography. Chromatographic peaks in the samples were identified by comparing the retention times with the retention times of the fatty acid esters in the analytical standard of a mixture of 37 fatty acid esters. The fatty acid composition is expressed as the relative mass fraction of the total fatty acids. The analysis of fatty acids in wild hemp seeds reveales the presence of 15 different acids, with content of 17.5% (U1) and 14.7% (U2) in relation to the total seed weight. Linoleic (45.3 and 47.5%) and a-linoleic (13.6 and 15.5%) acids were the most dominant. Of the 15 detected fatty acids, only 4 are saturated, with a representation of about 12%. Unsaturated fatty acids are present in a significantly higher proportion (about 88%), which indicates the nutritional value of these seeds.

Epoxidation of Palm Kernel Oil-Based Crude Oleic Acid

2014 ◽  
Vol 906 ◽  
pp. 125-130 ◽  
Author(s):  
Mohd Jumain Jalil ◽  
Noorfazlida Mohamed ◽  
Siti Khatijah Jamaludin ◽  
Ayub M. Som ◽  
Ahmad Rafizan Mohamad Daud
Keyword(s):  
Oleic Acid ◽  
Vegetable Oils ◽  
Palm Kernel ◽  
Performic Acid ◽  
Molar Ratio ◽  
Kernel Oil ◽  
Environmental Friendly ◽  
Renewable Natural Resources ◽  
Relative Conversion

Most vegetable oils have high content of unsaturated bond and can be converted into epoxidized fatty acids. These days, epoxidized vegetable oils are great concern as they are obtained from sustainable, renewable natural resources and are environmental friendly. The epoxidation of palm oleic acid was carried out by using in situ generated performic acid (HCOOOH) to produce epoxidized oleic acid. The degree of temperature, the molar ratio of formic acid or hydrogen peroxide and types of catalyst was considered. Epoxidation results were based on complete conversion oxirane, rate of epoxidation and stability of the oxirane. It was found that a maximum relative conversion oxirane (RCO) of epoxide is 88% at optimal condition.

A Surface Study of Ozone Attack and Antiozonant Protection of Carbon Black Loaded Natural Rubber Compounds

1979 ◽  
Vol 52 (4) ◽  
pp. 823-837 ◽  
Author(s):  
J. C. A. Andries ◽  
C. K. Rhee ◽  
R. W. Smith ◽  
D. B. Ross ◽  
H. E. Diem
Keyword(s):  
Fatty Acids ◽  
Carbon Black ◽  
Unsaturated Fatty Acids ◽  
Protective Layer ◽  
Thick Layer ◽  
Surface Concentration ◽  
Fatty Acid Esters ◽  
Reaction Products ◽  
Rubber Compounds ◽  
Acid Esters

Abstract This work reports a direct surface analysis of ozonization of carbon black loaded NR compounds by ATR and SEM. On ozonization of raw NR or NR containing carbon black, a thick layer builds up consisting of ozonides and carbonyl compounds. It is suggested that this layer is composed principally of the reaction products of ozone with unsaturated fatty acids and unsaturated fatty acid esters found in NR. On ozonization of cured and uncured carbon black loaded NR compounds containing curatives, the NR is attacked causing a decrease of rubber on the surface and a corresponding increase in the surface concentration of carbon black. The thick ozonide/carbonyl layer did not form, probably due to the coordination of the fatty acids and esters with ZnO, which was added with the curatives. On ozonization of carbon black-loaded NR compounds containing N,N′-dioctyl-p-phenylenediamine antiozonant, a continuous film is seen by SEM which has an ATR spectrum essentially identical to ozonized antiozonant. There is no evidence of ozonized NR products, or of complex reaction products between antiozonant and ozonized NR. These results are consistent with a dual scavenger and protective layer mechanism for antiozonant protection.

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