Comparatively Speaking: Fatty Acids vs. Ozone Acids
Figures
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Figure 1. Triglyceride saponification
Figure 1. Triglyceride saponification
Natural acids can be made by saponification of either methyl esters or triglycerides, followed by acidulation.
- Figure 2. Methyl ester saponification
Figure 2. Methyl ester saponification
Natural acids can be made by saponification of either methyl esters or triglycerides, followed by acidulation.
- Figure 3. Acidulation following triglyceride saponification
Figure 3. Acidulation following triglyceride saponification
Natural acids can be made by saponification of either methyl esters or triglycerides, followed by acidulation.
- Figure 4. Acidulation following methyl ester saponification
Figure 4. Acidulation following methyl ester saponification
Natural acids can be made by saponification of either methyl esters or triglycerides, followed by acidulation.
- Figure 5. The reaction of unsaturated acids with ozone
Figure 5. The reaction of unsaturated acids with ozone
Ozone acids are produced by the reaction of unsaturated acids with ozone. Ozonolysis of oleic acid is the major source for pelargonic and azelaic acids. The reaction is interesting since it produced a diacid and a lower molecular weight momofunctional acid.
Tables
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Table 1. Fatty acid nomenclature
Table 1. Fatty acid nomenclature
Designation Name Formula C6 Caproic acid C6H12O2 C8 Caprylic acid C8H16O2 C10 Capric acid C10H20O2 C12 Lauric acid C12H24O2 C12:1 Lauroleic acid C12H22O2 C14 Myristic acid C14H28O2 C14:1 Myristoleic acid C14H26O2 C16 Palmitic acid C16H32O2 C16:1 Palmitoleic acid C16H30O2 C18 Stearic acid C18H36O2 C18:1 Oleic acid C18H34O2 C18:2 Linoleic acid C18H32O2 C18:3 Linolenic acid C18H30O2 C20 Arachidic acid C20H40O2 C20:1 Gadoleic acid C20H38O2 C22 Behenic acid C22H44O2 C22:1 Erucic acid C22H42O2 C22:2 Clupanodinic acid C22H40O2 C24 Lignoceric acid C24H48O2 C26 Cerotic acid C26H52O2 C28 Montanic acid C28H56O2 C30 Myricic acid C30H60O2 C32 Lacceroic acid C32H64O2 C34 Geddic acid C34H68O2
By: Anthony J. O'Lenick, Jr., Siltech LLC
Posted: February 2, 2010
Natural acids can be made by saponification of either triglycerides (Figure 1) or methyl esters (Figure 2), followed by acidulation (Figures 3 and 4). The reaction sequence, whether by methyl esters or triglycerides, has two steps. The first step is saponification with base and the second is acidulation. If a triglyceride is used, glycerin results as the by-product. Similarly, if methyl ester is used, methanol is the by-product. The reaction produces a monosubstituted fatty acid identical to the feedstock going into the reaction. For fatty acid nomenclature, see Table 1.
Ozone acids are produced by the reaction of unsaturated acids with ozone, as seen in Figure 5. Ozonolysis of oleic acid is the major source for pelargonic and azelaic acids. The reaction is interesting since it produces a diacid and a lower molecular weight monofunctional acid.
The process was developed and patented in the 1950s by Emery, now Cognis. The process notably produces both diacid and odd carbon chain acids, which are not readily available from nature.
Any unsaturated acid can be subjected to the process to cleave the double bond and produce a diacid and pelargonic acid. The reaction of erucic acid results in pelargonic acid and brassylic acid 13-carbon diacid.
- Figure 2. Methyl ester saponification