Synthesis Of Aspirin

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

Separation and Purification of the Components of an Analgesic Tablet. Cora Bruno, Lab Section E. Aspirin, Caffeine and Acetaminophen were separated from four analgesic tablets of Excedrin using extraction techniques. 5% wt/vol NaHCO3, 4M HCL, ethyl acetate and deionized water were used to separate the three active components. MgSO4 was used to dry each extraction. Aspirin was isolated using a hot water bath and weighed to determine the percent theoretical recovery and the actual percent recovery of aspirin. After separation, Aspirin (ASA), Caffeine (CAF), and Acetaminophen (ACE) were purified and identified using Thin Layer Chromatography (TLC). Standards and purified ASA, CAF, and ACE were spotted on the silica gel (stationary phase) of the

The purpose of experiment four was to synthetically prepare a sample of salicylic acid from methyl salicylate, also known as wintergreen oil. The salicylic acid formed is to be compared to salicylic acid synthesized from benzene and determine whether or not the two acids differ. This experiment occurs through organic synthesis, meaning in order to create the desired product, the starting material must be chemically modified.

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

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

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

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

0.1 gram of salicylic acid was weighed in a tray and was then added to a test tube containing 2.0 mL of Iron (III) chloride, which was measured using a 10 mL graduated cylinder, to test for phenols.

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 greater the percentage of acetylsalicylic acid (ASA) in the tablet, more powerful and efficient the aspirin would be due to the way aspirin works in human’s body. Aspirin is often used to alleviate the pain, and the sensation of pain is mainly attributed to a chemical substance called prostaglandins, which is responsible to send a strong signal to the brain to remind the damage of the body. Working cells in the damaged area produce prostaglandins using an enzyme called cyclooxygenase 2 (COX-2), and aspirin works by disturbing COX-2 functions. By doing so prostaglandins are no more

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.

Sucrose is known to be insoluble in organic solvents such as dichloromethane (DCM) while Aspirin is soluble in DCM. Primarily, sucrose was removed so that it can be separated easily from the functioning ingredients that were present in Panacetin. Given that sucrose would not be able to dissolve if Panacetin was directly dissolved in the DCM. Aspirin however, is insoluble in water but it is known to contain a carboxylic acid group so it then will be able to react with sodium bicarbonate that is why the aspirin was recovered by reacting the conjugate base with hydrochloric acid. Finally, both Acetanilide and Phenacetin did not consist of an acidic hydrogen so instead they did not react with

The experiment was divided into a series of separation phases, a purification phase, and an analysis. Initially, 3.00g of Panacetin was weighed and dichloromethane (DCM) was added to the drug. Sucrose was filtered from this mixture by gravity filtration because it is not soluble in DCM while aspirin and is unknown are. Sodium bicarbonate was then added in order to extract aspirin from the filtrate. The base converted aspirin into its salt, allowing it to move into the aqueous layer of the mixture. The aqueous layers were obtained and hydrochloric acid was added,

The goal of this lab is to convert the salicylic acid into acetylsalicylic acid(aspirin) using different experimental techniques. These include recrystallization (purification), vacuum filtration (isolation), and melting point determination (characterization). After the melting point and a fair ferric chloride test was performed to test for the purity of the aspirin. The overall result was that the aspirin was light purple and the other vile dark purple. This showed that it was slightly impure.

In an esterification reaction, a carboxylic acid reacts with an alcohol. The synthesis of aspirin is an esterification reaction. Initially, the proton, i.e. the hydrogen ion, from the acid attacks the acetic anhydride and attaches itself on a double bond oxygen. This makes the compound more electrophilic, meaning that it has a higher affinity for electrons. This is what sets off the reaction. The salicylic acid then acts as an alcohol and attaches its OH group onto a carbon on the acetic anhydride. Then, the hydrogen from the OH group (the alcohol group) of the salicylic acid falls off, forming a tetrahedral intermediate, and the hydrogen ion reassociates with the conjugate base of the acid used as the catalyst. Next, the hydrogen that came from the acid initially, transfers its electrons and forms a double between the adjacent oxygen and carbon. However, the hydrogen atom does not fall off after the transfer of electrons but is kept there with a positive charge. With this, another transfer of electrons occurs and an acetyl group is generated from the breaking of the acetic anhydride. Now, the acetyl group breaks off the positive hydrogen attached and acetic acid is generated as a result. With this, the ester, the aspirin, is created (Watson