Isolating Trimyristin To Yield Myristic Acid

In this experiment, I carried out a hydrolysis reaction by isolating trimyristin to yield myristic acid and glycerol as a side product. The trimyristin was prepared by combining ground nutmeg and diethyl ether and heating the mixture under gentle reflux. The mixture was then washed and concentrated in a rotary evaporator, obtaining crude trimyristin, which was then purified via recrystallization with 95% ethanol. This yielded 0.230g of purified trimyristin, in the form of a white powder. The trimyristin was then mixed with sodium hydroxide and 95% ethanol under gentle reflux, yielding sodium myristate. Finally, concentrated hydrochloric acid was added dropwise, yielding myristic acid. I obtained a yield of 408.3% (0.523g) of the myristic acid

There are three main types of ester hydrolysis reactions: base-facilitated hydrolysis (saponification), acid-catalyzed hydrolysis (with the reverse reaction the Fischer Esterification), and enzymatic hydrolysis, triggered by lipases. Base-facilitated hydrolysis generally uses aqueous NaOH as a reagent, providing the base that attacks the carbonyl and begins the hydrolysis. Saponification hydrolyzes esters into carboxylic acids or fatty acids and alcohols. This has been used for thousands of years to produce soap from fatty acids as the salts produced from saponification can dissolve fats, surrounding them with micelles and allowing them to be easily removed with water1. It can also be used to produce glycerol from triglycerides. However, saponification needs a base to work, and strong bases such as NaOH (commonly known as lye) may pose a safety problem, as it is corrosive to the skin. Furthermore, saponification is an irreversible reaction. On the other hand, acid-catalyzed hydrolysis is equilibrium-controlled and therefore reversible1. The reverse reaction is called the Fischer esterification, and is used to create an ester from a carboxylic acid. Acid-catalyzed hydrolysis can be helpful when one desires to be able to reverse the reaction; however, like saponification reactions, the use of an acid causes this reaction to be unfavorable for neutral environments. The third reaction, enzymatic hydrolysis, can be used in neutral environments. It is a non-caustic manner of hydrolyzing, making it ideal for a neutral environment like the human body. With this reaction, lipases hydrolyze triglycerols to free fatty acids, allowing them to move more freely in aqueous environments. The reaction rate of lipase-catalyzed hydrolysis can be enhanced by the inclusion of other substrates such as crown ethers2. Triglycerides are composed of glycerol and three fatty acids and are hydrolyzed by