The Synthesis Of Aspirin ( Acetylsalicylic Acid )

Ever wonder about the chemical makeup of tablets that people take for pain relief? Before a tablet can be successfully made, the limiting and excess reactants must be considered. The limiting reactant will affect the amount of the product that can be made. Another reason why the starting reactants must be determined carefully is to make reduce the amount of the reactant in excess so that reactants are not wasted. This experiment uses an Alka-Seltzer tablet. Alka-Seltzer dissolves in water and is an antacid and a pain reliever1. The Alka-Seltzer tablet has many uses such as relief of headaches, ingestion, heart burns, or even upset stomachs2. The active ingredients in an Alka-Seltzer tablet is aspirin, also known as acetyl-salicylic acid (C8H12O4), citric acid (C6H8O7), and sodium bicarbonate (NaHCO3)2. The aspirin in the Alka-Seltzer tablet helps with pain relief. Because of the acid-base chemistry (Brønsted-Lowry), citric acid and sodium bicarbonate produce O2, which makes the tablet fizz when it is dropped in liquid. The Brønsted-Lowry theory shows how the Brønsted-Lowry acid donates a hydrogen ion while the Brønsted-Lowry base accepts the hydrogen ions3. The remaining NaHCO3 that is in excess post reaction with the citric acid is what is used to neutralize stomach acid which helps relief heart burn2. The problem in

Aspirin, Caffeine and Salicylamide were extracted from an over-the-counter pain reliever (BC Powder). These components were separated by manipulating their solubilities by adjusting the acidity and basicity of the solution. By doing this, the three components were forced into conjugate acid (or base) forms, causing selective solubility in either an aqueous or organic solvent. These layers were then separated by use of a separation funnel. Once separated, the components extracted were characterized by measuring the melting point and performing a TLC analysis. Also, the recovered aspirin from the first part of the experiment was recrystallized and compared to that of the

During this experiment, guaifenesin was isolated and synthesized through a reflex process, which both heated the mixture and preserved the solid. Two Guai-Aid cough tablets, each containing 400 mg of guafenesin each, were used. The synthesis of guaifenesin resulted in a 23.7% yield based on the theoretical value of .6207 of guaifenesin given the limiting reactant, 2-methoxyphenol. The isolation of guafenesin resulted in a 5.38% yield due to the fact the isolation was completed from two 400mg tablets of guaifenesin. HNMR and a melting point test were both used to successfully confirm that guaifenesin was the product of the synthesis and isolation methods through the location of the peaks on the spectra and the comparison of melting points to the literature value.

Aspirin is one of the most consumed painkillers created up to this date due to its reliability and low expense. It is often used to relieve minor aches and pains, reduce fever and as an anti-inflammatory medication. Due to its wide range of uses, the demand for this pharmaceutical is very high. As a result, manufacturers who produce this drug must be efficient in order to reduce the time taken to produce this drug and produce the in very high quantities.

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

Acetic Anhydride and p-Aminophenol were heated in a vial attached to an air condenser to synthesize crude acetaminophen, resulting in 0.097 grams (47.48% yield). The crude acetaminophen was then recrystallized in a solvent of water and methanol over heat resulting in 0.082 grams (39.61% yield) of pure acetaminophen. Melting points of both crude and pure acetaminophen were taken, and found to be 165.9 - 170.9°C and 168.2 - 171.5°C, respectively. The literature melting point of acetaminophen is 169.5 – 171.0°C, indicating that our final product was pure.

The production of aspirin begins salicylic acid which has been derived from the active site of salicin found in willow bark. This is done through multi-step process where substrates of salicin are converted into more basic products such as salicylic acid. Salicylic acid cannot be consumed by itself due to the fact that it is bitter and irritates the stomach causing side effects such as nausea and internal bleeding within the stomach. This is due to the fact that salicylic acid exists in protonated form in the stomach; therefore, the pH of the salicylic acid is low, thus affecting the lining of the stomach. Therefore, to stabilise salicylic acid, it is synthesized into acetylsalicylic acid also known as aspirin. Acetylsalicylic acid is not pronated in the stomach and thus, the pH of acetylsalicylic acid is not as low compared to salicylic acid, thus it does not affect the lining of the stomach as much compared to salicylic acid.

Acetaminophen is created when the amine group of p-aminophenol is acetylated by acetic anhydride. This creates an amide functional group and 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

willow tree bark used as early as 400 B.C. to relieve pain. It is also known as salicylic acid.

The purpose of the lab was to synthesize aspirin and oil of wintergreen, and to determine its purity using recrystallization process, determining its melting point and using back-titration. To synthesize aspirin, salicylic acid and anhydride was used to drive the reaction to completion. In the synthesis of oil of wintergreen we reacted salicylic acid and methanol to produce methyl salicylate. This reaction is an example of a condensation reaction where the carboxylic acid and alcohol group combine to form an ester. In producing aspirin, we wanted to obtain the purest form, so we removed impurities such as unreacted salicylic acid and acetic acid. Acetic acid was removed by rinsing the sample in water because acetic acid is soluble in water. Salicylic, however, was removed by using the recrystallization process because it is insoluble in water. To recrystallize, we dissolved a sample of crude aspirin in warm ethanol and let it cool. Because aspirin is less soluble in ethanol than salicylic acid, it will crystallize out of the solution. To obtain the purified aspirin sample, we then filtered the solution to separate it from the impurities. To determine qualitatively the purity of the recrystallized aspirin, we determined its melting point using a melting point apparatus. Using the idea of freezing point depression, the presence of impurities will lower the melting point of the substance. Thus, by comparing the melting point to the actual

The purpose of this lab was to synthesize aspirin, determine the theoretical yield, compare the percent yield to the theoretical yield and test the purity of aspirin by adding Iron (III) chloride to the product.

The goal of this experiment was to synthesize aspirin. In this experiment aspirin, also known as acetylsalicylic acid, was synthesized from salicylic acid and acetic anhydride. In the reaction the hydroxyl group on the benzene ring in salicylic acid reacted with acetic anhydride to form an ester functional 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. After the reaction was complete some unreacted acetic anhydride and salicylic acid was still be present in the solution as well as some sulfuric acid, aspirin, and acetic acid. Crystallization, which uses the principle of

“Use of herbs as medicines dates back to the beginning of civilized man. The earliest known written records of herbal medicines were inscribed on a six thousand year old clay tablet written by the Sumerians, who lived on the banks of the Tigris and Euphrates rivers in what is now known as Iraq”(History).

This experiment involved three steps: synthesis of aspirin, isolation and purification, and the estimation of purity of the final product. The synthesis involved the reaction of salicylic acid and acetic anhydride in the presence of a catalyst, phosphoric acid, H3PO4. When the aspirin was prepared, it was isolated and filtered. The percentage yield of the synthesis was calculated to be 78.42%. The experimental melting point range of aspirin was determined to be 122 -132°C. Due to its wide range, and lower value than that of the theoretical melting point of 136°C, it was