Comparatively Speaking: Fatty Acids vs. Ozone Acids

Feb 2, 2010 | Contact Author | By: Anthony J. O'Lenick, Jr., Siltech LLC
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Title: Comparatively Speaking: Fatty Acids vs. Ozone Acids
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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.

 

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Table 1. Fatty acid nomenclature

 Designation  Name  Formula
 C6 Caproic acid  C6H12O2
C8 Caprylic acid  C8H16O
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

Figure 1. Triglyceride saponification

Triglyceride Saponification

Natural acids can be made by saponification of either methyl esters or triglycerides, followed by acidulation.

Figure 2. Methyl ester saponification

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

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

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

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.

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