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Edible Oils, Fats, and Waxes | Mcgraw-Hill Education 4. Edible Oils, Fats, and Waxes Mohammad Farhat Ali 4.1. Introduction Fats, oils, and waxes are naturally occurring esters of long straight-chain carboxylic acids. They belong to the saponifiable group of lipids. Lipids are biologically produced materials that are relatively insoluble in water but soluble in organic solvents (benzene, chloroform, acetone, ether, and the like). The saponifiable lipids contain an ester group and react with hot sodium hydroxide solution undergoing hydrolysis (saponification): Saponification is a chemical process in which an ester is heated with aqueous alkali (sodium hydroxide) to form an alcohol and the sodium salt of the acid corresponding to the ester. The sodium salt formed is called soap. Fats and oils are esters of glycerol, the simplest triol (tri-alcohol), in which each of the three hydroxyl groups has been converted to an ester. The acid portion of the ester linkage (fatty acids) usually contains an even number of carbon atoms in an unbranched chain of 12 to 24 carbon atoms. The triesters of glycerol fats and oils are also known as triglycerides. The difference between fats and oils is merely one of melting point: fats are solid at room temperature (20°C) whereas oils are liquids. Both classes of compounds are triglycerides. As glycerol is common to all fats and oils, whether animal or vegetable, it is the fatty acid part of the fat (oil) that is of interest. The differences among triglycerides (fats and oils) are because of the length of the hydrocarbon chains of the acids and the number of position of double bonds (unsaturation). © McGraw-Hill Education. All rights reserved. Any use is subject to the Terms of Use, Privacy Notice and copyright information. The hydrocarbon chains of the fatty acids may be completely saturated (saturated fat) or may contain one or more double bonds. The geometric configuration of the double bond in fats and oils is normally cis. If the chain includes more than one double bond, the fat is called polyunsaturated. The presence of a double bond puts a kink in the regular zig-zag arrangement characteristic of saturated carbons. Because of this kink in the chains, the molecules cannot form a neat, compact lattice and tend to coil, so unsaturated triglycerides often melt below room temperature and are thus classified as oils. Fats and oils are the most concentrated source of energy. They provide approximately 9 kcal of energy per gram, compared to 4 kcal/g for proteins and carbohydrates. They are carriers of fat-soluble vitamins and essential fatty acids. They also contribute to food flavor and mouth-feel as well as to the sensation of product richness. They are used as frying fats or cooking oils where their role is to provide a controlled heat-exchange medium as well as to contribute to color and flavor. They are also used in many other commercial applications, including soaps, detergents, and emulsifiers, printing inks, protective coatings, and feeds for domesticated animals. Waxes are monoesters of long-chain fatty acids, usually containing 24 to 28 carbon atoms, with long-chain fatty primary alcohols. A fatty alcohol has a primary alcohol group (-CH2OH) attached to a 16-to-36 carbon atoms long chain. Waxes are normally saturated and are solids at room temperature. Plant waxes are usually found on leaves or seeds. Thus, cabbage leaf wax consists of the primary alcohols C12 and C18-C28 esterified with palmitic acid and other acids. The dominant components are stearyl and ceryl alcohol (C26H53OH). In addition to primary alcohols, esters of secondary alcohols, for example, esters of nonacosane-15-ol, are present: Waxes can be classified according to their origins as naturally occurring or synthetic. The naturally occurring waxes can be classified into animal, vegetable, and mineral waxes. Beeswax, spermaceti, wool grease, and lanolin are important animal waxes. The vegetable waxes include carnauba, ouricouri, and candelilla. Petroleum waxes are the most prominent mineral waxes. Paraffin wax is petroleum wax consisting mainly of normal alkanes with molecular weights usually less than 450. Microcrystalline wax is another type of petroleum wax containing substantial amounts of hydrocarbons other than normal alkanes, and the components have higher molecular weights than paraffin wax components. Compositions of significant © McGraw-Hill Education. All rights reserved. Any use is subject to the Terms of Use, Privacy Notice and copyright information. commercial waxes from natural sources are given in Table 4.1 [1]. Table 4.1 Sources and Compositions of Normal Waxes Type Melting point °C Main components Animal waxes Beeswax 64 Myricyl palmitate Chinese 82–84 Isoheptacosyl isoheptacosanoate, ceryl lignocerate Shellac 81–82 Ceryl lignocerate, ceryl cerotate Spermaceti –– Cetyl palmitate Wool (anhydrous lanolin) 36–42 Cholesteryl estolidic esters, alcohol esters of iso- and anteiso acids Mineral waxes Montan 86 Tricontanyl esters of C28–30 acids Petroleum waxes Microcrystalline 71–88 Hydrocarbons (490–800 molecular weights) Paraffin 54–57 Hydrocarbons (350–420 molecular weights) Vegetable waxes Bayberry 43–48 Trimyristin, tristearin Candelilla 70–80 C29–33 hydrocarbons, simple esters and lactones Carnauba 80–85 Esters of C26–30 alcohols and C26–30 ω-hydroxy acids Esparto 69–81 Hydrocarbons, esters of C26–32 acids and alcohols Japan 51–62 Tripalmitin Jojoba (a liquid wax) 11–12 Docosenyl eicosanoate Ouricury 79–85 Myricyl cerotate and hydroxycerotate Sugarcane 79–81 Myricyl palmitate stigmasteryl palmitate 4.2. Fatty Acids The carboxylic acids obtained from the hydrolysis of fat or oil are called fatty acids. They are the building blocks of the triglycerides and the fats and oils are often named as derivatives of these fatty acids. For example, the tristearate of glycerol is named tristearin and the tripalmitate of glycerol is named tripalmitin. Normal saturated fatty acids have a long, unbranched hydrocarbon chain having a general formula CH3(CH2)nCOOH, where n is © McGraw-Hill Education. All rights reserved. Any use is subject to the Terms of Use, Privacy Notice and copyright information. 3 2 n usually even and varies from 2 to 24. The unsaturated fatty acids may have one double bond (monosaturated) or have more than onec is-methylene interrupted double bond (polyunsaturated) as illustrated in Fig. 4.1. Figure 4.1 The structure of some fatty acids. The following three systems of nomenclature are in use for naming fatty acids. a. The common (trivial) names b. The number of carbon atoms in the chain c. The International Union of Pure and Applied Chemistry (IUPAC) system The trivial names that indicate the initial source of fatty acids are used more often than the IUPAC names in the industry. For example, butyric acid is a major component of butter flavor, palmitic acid comes from palm kernel, and oleic acid from olives. The number of carbon atoms in the chain, followed by a colon and additional numbers indicating the number of double bonds, are used as an abbreviation to designate fatty acids. Thus in the 18-carbon series, C18:0, C18:1, C18:2, and C18:3 represent stearic, oleic, linoleic, and linolenic acids, respectively. One or two letter abbreviations are also used, and these four acids sometimes are designated by St, O, L, and Ln, respectively. The IUPAC name of fatty acid is that of the alkane parent with the –e changed to –oic acid. The carboxyl carbon is carbon 1: © McGraw-Hill Education. All rights reserved. Any use is subject to the Terms of Use, Privacy Notice and copyright information. The suffix dioic is used if the acid contains two carboxyl groups. The double bonds in fatty acids differ in (a) number, (b) location, (c) geometrical configuration, and (d) conjugation. Conjugation is a special case of location in which two double bonds are separated only by a single carbon-carbon bond. Unsaturated fatty acids may have one or as many as six double bonds. Those containing multiple double bonds usually have a methylene (CH2) group between the double-bond sequence, so the system is not conjugated. When double bonds are present, the suffix anoic is changed to enoic, dienoic, or trienoic to indicate the number of bonds present. The location of the first carbon in the double bond is indicated by a number preceding the IUPAC systematic name. The geometric configuration of double bonds is indicated by the Latin prefixes cis- (both hydrogens on one side) and trans- (hydrogen across from each other). Unsaturation between the 9 and 10 carbons with cis orientation is most common in polyunsaturated fatty acids. Accordingly, oleic, linoleic, and linolenic acids are called 9-octadecenoic, 9,12-octadecadienoic and 9,12,15-octadecatrienoic acids, respectively. Table 4.2 lists some common examples of fatty acids, their sources, common names, and systematic names [1]. Many additional terms are used to distinguish unsaturated fatty acids by the location of the first double bond relative to the omega 9 9,12 (ω) or -CH3 carbon. Thus oleic acid is both Δ and a C18:1 ω-9 acid. Linoleic acid is a Δ and C18:2 ω-6 acid. Linolenic acid is both Δ9,12,15 and a C18:3 ω-3 acid. © McGraw-Hill Education. All rights reserved. Any use is subject to the Terms of Use, Privacy Notice and copyright information. Table 4.2 Some Important Fatty Acids, Their Names and Common Sources Carbon atoms Common name Systematic name Common sources SOURCE: Riegel's Handbook of Industrial Chemistry, 9th ed., 1992. Saturated fatty acids 3 Propionic Propanoic Bacterial fermentation 4 Butyric Butanoic Milk fats
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