In this experiment, acetylsalicylic acid or aspirin was synthesized by the esterification reaction between salicylic acid and acetic anhydride. This esterification reaction consisted of acetic anhydride with a carboxylic acid functional group and salicylic acid with an alcohol functional group making acetylsalicylic acid, which contains an ester functional group. Sulfuric acid was used as a catalyst to make the products of acetic anhydride and acetic acid.
The experimental technique of crystallization was used to purify acetylsalicylic acid from other substances, because when the esterification reaction was complete some unreacted salicylic acid and acetic anhydride was present along with acetylsalicylic acid, acetic acid, and the catalyst: sulfuric acid. Crystallization occurs because at the end of the reaction the reaction mixture
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The expected acetylsalicylic acid product produced was 1.313g, therefore the crude percent yield calculated was 70.35% yield. This percent yield indicates that a high percentage of product was made, however the yield was not 100%, therefore loss of product was evident in the reaction process. Moreover, in the ferric chloride test, the salicylic acid and water, as well as the acetylsalicylic acid and water formed a dark purple color. However, acetylsalicylic was not supposed to react with ferric chloride and turn purple, because pure acetylsalicylic acid is not a phenol and therefore should not react. The melting point was determined to be 165 C and this is a higher melting point than the literature value of 135 C. The product of acetylsalicylic acid was obtained because a high yield was obtained, however the product was not pure and contained unreacted salicylic acid, because the ferric chloride test resulted in a purple color and the melting point determined was greater than the literature
The purpose of this experiment was to perform an esterification reaction with an unknown carboxylic acid, resin, and 1-butanol. In this experiment, 114 mg of 1-butanol, 329 mg and 50.3 mg resin were added to a conical vial. The vial was reflux for an hour on a hot plate and later cool to room temperature. The product of this reaction is C_14 H_20 O_2, which was extracted by pipet into a centrifuge tube. 6 mL of ether was used to rinse all the product into the centrifuge tube.
o prepare Acetaminophen a water bath was set up in a 400-mL beaker and then placed onto a hotplate where it reached a boil. During the time it took for the water bath to boil, a 125-mL Erlenmeyer flask was obtained. P-aminophenol (1.5g) was weighed and then placed inside the Erlenmeyer flask. Deionized water (25 mL) was added to the flask followed by 35 drops of concentrated phosphoric acid. An additional 15 drops were added to the solution, since the initial 20 drops of concentrated phosphoric acid was not dissolving the p-aminophenol. Phosphoric acid was added to the reaction mixture because it acted as a catalyst for the reaction. The flask was then swirled gently until all of the p-aminophenol had dissolved. Once the water bath came to
In this experiment, the Fischer Esterification of an unknown acid and an unknown alcohol was used to prepare an unknown ester. Sulfuric acid was used as a catalyst in the reaction which then was put under reflux. After cooling, the pH of the solution was raised to approximately 8 using sodium carbonate. Diethyl ether was added, then the aqueous layer was removed and the organic layer was washed with sodium chloride. The aqueous layer was removed again and sodium sulfate was added. The unknown product was then identified using gas chromatography (GC) to obtain the retention time.
Industrial production of Aspirin is dependent on the company producing the drug; however the general method of production is known as slugging or dry-granulation. In this method, corn starch is mixed with pure water and is then heated and
The isolation of aspirin, acetaminophen, and caffeine from Excedrin utilized the differing acidities and polarities of the three compounds. Extraction involved separating the three components by reacting them with HCL and NaOH, while thin layer chromatography involved separating the isolated compounds on a TLC plate. The binder was the first component extracted; followed by aspirin, acetaminophen, and caffeine was extracted last since it is a neutral and polar compound. The entire process can be seen in figure 1. The most utilized methods of extraction were gravity filtration and vacuum filtration which are displayed in figures 3 and 4 respectively. These methods were utilized to separate compounds based upon their differing
The product was placed in a Craig tube and several drops of hot (100°C) solvent (50% water, 50% methanol, by volume) was added and heated until all of the crystals dissolved. The Craig tube was plugged and set in an Erlenmeyer flask to cool. Crystallization was induced once the mixture was at room temperature by scratching the inner wall of the tube. It was then placed into an ice bath for ten minutes until crystallization was complete. The tube was then
An ester was synthesized during an organic reaction and identified by IR spectroscopy and boiling point. Acetic acid was added to 4-methyl-2-pentanol, which was catalyzed by sulfuric acid. This produced the desired ester and water. After the ester was isolated a percent yield of 55.1% was calculated from the 0.872 g of ester recovered. This quantitative error was most likely due to product getting stuck in the apparatus. The boiling point of the ester was 143° C, only one degree off from the theoretical boiling point of the ester 1,3-dimethylbutyl, 144 ° C. The values of the
Aspirin also known as acetylsalicylic acid is a salicylate drug, often used as an analgesic to relieve minor aches and pains, as an antipyretic to reduce fever, and as an
The purpose of this lab was to synthesize the ester isopentyl acetate via an acid catalyzed esterification (Fischer Esterification) of acetic acid with isopentyl alcohol. Emil Fischer and Arthur Speier were the pioneers of this reaction referred to as Fischer Esterification. The reaction is characterized by the combining of an alcohol and an acid (with an acid catalyst) to yield and ester plus water. In order to accomplish the reaction, the reactants were
I hypothesize that salicylic acid will react with acetic anhydride to produce acetylsalicylic acid (aspirin) and acetic acid (vinegar).
Salicylic acid was esterfied using acetic acid and sulfuric acid acting as a catalyst to produce acetylsalicylic acid and acetic acid. The phenol group that will attack the carbonyl carbon of the acetic anhydride is the –OH group that is directly attached to the benzene since it is more basic than the –OH group attached to the carbonyl group. This method of forming acetylsalicylic acid is an esterification reaction. Since this esterification reaction is not spontaneous, sulfuric acid was used as a catalyst to initiate the reaction. Sulfuric acid serves as the acid catalyst since its conjugate base is a strong deprotonating group that is necessary in order for this reaction to be reversible. The need for the strong conjugate base is the reason why other strong acids such as HCl is not used since its conjugate base Cl- is very weak compared to HSO3-. After the reaction was complete some unreacted acetic anhydride and salicylic acid was still be present in
The purpose of this experiment is to prepare isopentyl acetate by direct esterification of acetic acid with isopentyl alcohol. After refluxing there is an isolation procedure where excess acetic acid and remaining isopentyl alcohol are easily removed by extraction with sodium bicarbonate and water. The ester is then purified by simple distillation and the IR is then obtained.
This report presents the synthesis of Aspirin (acetylsalicylic acid), as the product of the reaction of salicylic acid with ethanoic anhydride under acidic conditions. Aspirin was purified through recrystallisation by vacuum filtration, followed by desiccation of the Aspirin crystal over silica gel. The percentage yield was calculated as 44.89% and a sample of Aspirin was analysed using infra-red spectroscopy and compared to the spectrum of pure Aspirin, this served as an introduction to the identification of functional groups in organic compounds. The melting point was calculated using an IA9000M apparatus and recorded to be 35.2°C, which was slightly below the melting point of pure Aspirin; known to be between 138-140°C. Both IR spectroscopy and melting point measurement were used verify the purity of synthetic Aspirin made, which proved to be fairly pure under these laboratory conditions.
Purpose The purpose of this experiment was to prepare acetylsalicylic acid, which is aspirin, investigate two of its chemical properties, and measure the purity of the synthesized aspirin. The aspirin was created in an esterification reaction between salicylic acid and acetic anhydride. Using the aspirin that was made from salicylic acid and acetic anhydride, it was tested to see if the salicylic acid in the aspirin acts as a phenolic alcohol or as a carboxylic acid by adding FeCl3 solution.
3.0g of salicylic acid was weighed then 3.0mL of acetic anhydride and 6 drops of 85% H3PO4 were added to it. The mixture was warmed over a water bath for 5 minutes while stirring. After warming, 20 drops of distilled water was slowly added. 15mL of water was added then the solution was heated until it became clear. It was allowed to cool and was placed in an ice bath until the solution becomes cloudy. Using pre-weighed filter paper, the mixture was filtered and was allowed to dry in the filter paper.