Saponification Myristic Acid
Saponification and Acidification: From Nutmeg to Trimyrisitin to Sodium Myristate to Myrisitic Acid
Mandy Boyle
Chem 213, Section 002
Due Date: December 3, 2009
I. Introduction
People encounter esters everyday in both natural and synthesized forms. Esters are present in a variety of common compounds, from fragrances to animal fat (McMurry, 2008). Although these esters can undergo many different important reactions, this lab is particularly interested in the hydrolysis of esters into carboxylic acids and alcohols. Companies such as Dove, Palmolive, Dial, and many others owe their success to this specific reaction because the carboxylic acid produced in this reaction is soap. As such, this process is also commonly known as saponification …show more content…
The trimyristin IR shows a stretch at 1732.4 cm-1, which is concurrent with the expectations due to the ester present in trimyristin’s structure. This indicates that trimyristin was successfully extracted from nutmeg. The myristic acid IR shows stretches at 2914.2 cm-1 and 1693.6 cm-1. Since sodium myristate has the same structure as myrisitic acid aside from the proton of the carboxylic acid, the O-H bond stretch is the most significant factor in determining if the myristic acid was indeed synthesized. Thus, the 2914.2 cm-1 bond stretch indicates a successful synthesis of myristic …show more content…
Soap is somewhat miscible in both fat and water, so adding soap to corn oil would be expected to produce emulsions. Emulsions within a homogenous solution were in fact produced, suggesting that sodium myristate was successfully synthesized. Adding soap to aqueous FeCl3 or aqueous CaCl2 would cause the ions to exchange and create iron or calsium myristate, the insoluble brown and white precipitates formed during the second and third qualitative tests (Noller, 1953). These preciptates therefore suggest that sodium myristate was successfully synthesized. The myristic acid NMR analysis (attached to the end of the report) also indicates a successful synthesis. Aside from the acetone and DCM impurities, the myristic acid NMR shows hydrocarbon peaks at 2.213ppm and .879ppm. These peaks coupled with the fact that sodium myristate would not dissolve in the organic dichloromethane solvent indicates that the reaction resulted in the synthesis of myristic acid. Unfortunately, the high volume of the impurities throws off the integration values of the peaks, so the integration values given cannot be used to indicate the identity of the
Mandy Boyle
Chem 213, Section 002
Due Date: December 3, 2009
I. Introduction
People encounter esters everyday in both natural and synthesized forms. Esters are present in a variety of common compounds, from fragrances to animal fat (McMurry, 2008). Although these esters can undergo many different important reactions, this lab is particularly interested in the hydrolysis of esters into carboxylic acids and alcohols. Companies such as Dove, Palmolive, Dial, and many others owe their success to this specific reaction because the carboxylic acid produced in this reaction is soap. As such, this process is also commonly known as saponification …show more content…
The trimyristin IR shows a stretch at 1732.4 cm-1, which is concurrent with the expectations due to the ester present in trimyristin’s structure. This indicates that trimyristin was successfully extracted from nutmeg. The myristic acid IR shows stretches at 2914.2 cm-1 and 1693.6 cm-1. Since sodium myristate has the same structure as myrisitic acid aside from the proton of the carboxylic acid, the O-H bond stretch is the most significant factor in determining if the myristic acid was indeed synthesized. Thus, the 2914.2 cm-1 bond stretch indicates a successful synthesis of myristic …show more content…
Soap is somewhat miscible in both fat and water, so adding soap to corn oil would be expected to produce emulsions. Emulsions within a homogenous solution were in fact produced, suggesting that sodium myristate was successfully synthesized. Adding soap to aqueous FeCl3 or aqueous CaCl2 would cause the ions to exchange and create iron or calsium myristate, the insoluble brown and white precipitates formed during the second and third qualitative tests (Noller, 1953). These preciptates therefore suggest that sodium myristate was successfully synthesized. The myristic acid NMR analysis (attached to the end of the report) also indicates a successful synthesis. Aside from the acetone and DCM impurities, the myristic acid NMR shows hydrocarbon peaks at 2.213ppm and .879ppm. These peaks coupled with the fact that sodium myristate would not dissolve in the organic dichloromethane solvent indicates that the reaction resulted in the synthesis of myristic acid. Unfortunately, the high volume of the impurities throws off the integration values of the peaks, so the integration values given cannot be used to indicate the identity of the