Soap - Preparation of Soap By Walter Scharf and Charles...

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Chapter 19 / Exercise 19-64
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Preparation of SoapBy Walter Scharf and Charles MalerichNatural Sciences/ChemistryBaruch CollegeNew York, NY 10010Introduction Soap, from a chemical standpoint, is a salt (or a mixture of salts) of fatty acids. As with all salts, soap contains a positive ion, usually Na+or K+, and a negative ion, usually the anions of long-chained carboxylic acids obtained by the hydrolysis of animal or vegetable fats. These fatty acids, of which there are about 20 naturally occurring members, are carboxylic acids containing 14, 16, or 18 carbon atoms in an unbranched chain. The even numbered chains result from the fact that fats are synthesized in cells by the polymerization of a 2-carbon acetate unit.In addition to the normal (straight chain) saturated acids, there occur several with hydroxyl groups, and/or one or more double bonds in the carbon chain. the presence of unsaturation (double bonds) in molecules of fatty acids, fats, or soup tend to lower the melting point of these compounds and to cause them to be in the liquid state at room temperature. Thus, vegetable fats are relatively unsaturated and liquid under the ordinary conditions, while animal fats, being relatively more saturated, are solid, or semi-solid, at the same temperature. For this reason, vegetable fats are commonly refereed to as vegetable oils.(We say relatively saturated, orunsaturated because both vegetables oils and animal fats contain saturated andunsaturated chains). The reason why double bonds lower the melting point of a fatty acid chain, is that the sections of the chain attached to the double bond are attached cis-wise to each other (probably because the double bond cisconfiguration produces a bent chain which does not easily adhere to a neighboring chain by a Van der Waals attraction hence a lower temperature (lower mobility) is required for these molecules to adhere in order to form a solidcrystal lattice. It is interesting to note, that straight chained carboxylic acids having an odd number of carbon atoms melt lower than even chained acids of comparable molecular weights.
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Chapter 19 / Exercise 19-64
General, Organic, & Biological Chemistry
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The most commonly encountered fatty acids in natural fats are given below:Saturated AcidsLauric Acid (Dodecanoic Acid)CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-COOHMyristic Acid (tetraderanoic Acids)CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-COOHPalmitic acid (hexadecanoic acid)CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-COOHStearic acid (octadecanoic acid)CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-COOHUnsaturated acids:Oleic acid (octadec-9-enoic acid)CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH=CH- CH2-CH2-CH2-CH2-CH2-CH2-CH2-COOHLinoleic acid (octadec-9, 12-dienoic acid)CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH=CH- CH2-CH2-CH2-CH2-CH2-CH2-CH2-COOHAll fats are esters (though, not all esters are necessarily, fat!) of the trihydroxy alcohol, glycerin, and fatty acids. Since each molecule of fat contains three ester groups, fats are often

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