Acetylsalicylic acid does not have the bad taste and stomach problems of salicylic acid. The solid aspirin will again be collected using vacuum filtration and tested for purity. Synthesis of aspirin lab report 2989 words bartleby. H 2 so 4 use a dropper, h 2 so 4 is highly corrosive and swirl the flask gently until the salicylic acid dissolves heat the flask gently on the steam bath for at least 10 minutes. The use of aspirin had its origin in the 18th century, when it was found that an extract from the. Ac158180000, ac158180025, ac158185000, ac385760000 synonyms. A structure and antioxidant activity study of paracetamol. This experiment was carried out to see how the hydroxyl group on the benzene ring in salicylic acid reacts with acetic anhydride to form an ester, and to make aspirin. E29 preparation of aspirin acetylsalicylic acid and thin. Pdf preparing a pure aspirin acetylsalicylic acid researchgate.
A small amount of a strong acid is used as a catalyst which speeds up the reaction. The usefulness of functional groups will be illustrated as well as the use of nmr, ir, and melting point in characterizing a product. Salicylic acid the first person to do so was a french chemist named charles frederic gerhardt. Acetylsalicylic acid aspirin synthesis johnson, chad philip. It was developed by charles frederic gerhardt in the mid 19th century, but it didnt gain popularity until the early 20th. Experiment 22 synthesis of aspirin and oil of wintergreen goals. In this exercise, the goal was to produce acetylsalicylic acid through the organic synthesis from the reaction of salicylic acid to acetic anhydride, the starting materials. A structure and antioxidant activity study of paracetamol and. Preparation, purification and analysis of aspirin acetylsalicylic acid synthesis. For this reason, it is industrially synthesized on a massive scale, producing up to 1800 kg 10,000 moles per batch. Aspirin acetylsalicylic acid is the most common medicinal drug in use today. Aspirin is an effective analgesic pain reliever, antipyretic fever reducer and antiinflammatory agent and is one of the most widely used nonprescription drugs. Microscale synthesis of acetylsalicylic acid aspirin acetyl salicylic acid mw180.
It is a nonsteroidal antiinflammatory drug nsaid with a wide range of physiological effects. After synthesis and analysis, it will be determined if the crude and recrystallized samples were composed solely of either salicylic acid, acetylsalicylic acid, or a combination of both 3. You will analyse several samples to determine the amount of salicylic acid impurity in your synthesized aspirin. In the reaction the hydroxyl group on the benzene ring in salicylic acid reacted with acetic anhydride to form an ester functional group. Aspirin is superior to salicylic acid for oral dosage in that the latter is very bitter, and causes stomach.
H 2 so 4 use a dropper, h 2 so 4 is highly corrosive and swirl the flask gently until the salicylic acid dissolves. An experiment is described that is suitable for the early portion of the laboratory in a general chemistry course and integrates organic examples. The use of aspirin had its origin in the 18 th century, when it was found that an. On the contrary, the salicylic acid does not present this effect at the same condition and concentration. After the synthesis was complete, you analyzed both the crude and recrystallized product using ir analysis. 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. Request pdf synthesis of acetylsalicylic acid in choline chloride based eutectic solvents acetylsalicylic acid or aspirin is a medicine that has antipyretic and anticoagulant properties and. In folk medicine, willow bark teas were used as headache remedies and other tonics. Williamson, macroscale and microscale organic experiments, 2nd ed. Clamp the stoppered erlenmeyer flask to a ring stand to hold it in the 7080. Synthesis of acetylsalicylic acid in choline chloride. Synthesis of acetylsalicylic acid in choline chloride based. Synthesis of acetylsalicylic acid occurs by protonation of carbonyl co group, and a nucleophilic attack of oh on the acetic anhydride. The mechanism for this synthesis provides examples of three major classes of chemical reactions.
Acetylsalicylic acid an overview sciencedirect topics. Certificate of analysis coa specification sheet pdf. Aspirin synthesis tap water was heated on a steam bath in a 250 ml beaker. Synthesis of aspirin synthesis purification characterization. Salicylic acid, whose name comes from salix, the willow family of plants, was derived from willow bark extracts. To understand the chemistry, the student must be able to recognize the common molecular framework shared by oil of wintergreen, salicylic acid, and aspirin and to identify the oh and co2 sites where. In 1853, gerhardt neutralized salicylic acid by buffering it with sodium sodium salicylate and acetyl chloride, creating acetylsalicylic acid. To determine which of four catalysts yields the fastest reaction rate in the acetylation of salicylic acid 1 to form acetylsalicylic acid 2. Aspirin is the common name for the compound acetylsalicylic acid, widely used as a fever reducer and as a pain killer. At very low doses, aspirin is used to treat and prevent heart attacks and blood clots. Salicylic acid was esterfied using acetic acid and sulfuric acid acting as a catalyst to produce acetylsalicylic acid and acetic acid. Synthesis of acetylsalicylic acid free essay example.
Thus, salicylic acid is limiting and a maximum of 0. The method described before is that followed by most manufacturers to make this chemical. Heat the reaction mixture until the solids have fully. Once acetylsalicylic acid is absorbed from the intestine, it is converted back to salicylic acid. Acetylsalicylic acid is not very soluble in cold water 0. The temperature of an alcohol thermometer was equilibrated in a beaker of room temperature tap water.
It was developed by charles frederic gerhardt in the mid 19th century, but it. This experiment will demonstrate the preparation of aspirin. Note in equation 293 that the byproduct of the reaction is now acetic acid rather than water. Txa2 has vasoconstriction activity with increased platelet aggregation, and inhibition results in opposite effects, favorable in preventing arterial. It is effective in relieving symptoms of pain analgesic due to headaches, injury, or arthritis, treating fever antipyretic and inflammation, and preventing blood clots 1. Synthesis of aspirin lab report and analysis odinity. Your synthesis converted most, but not all, of the salicylic acid into acetylsalicylic acid. The two step synthesis encompasses aqueous base hydrolysis of wintergreen oil methyl salicylate, ms to salicylic acid sa followed by acetylation to acetylsalicylic acid aspirin, asa.
Synthesis of salicylic acid from oil of wintergreen. Company replaced the phenol group with an ester group. When salicylic acid reacts with acetic anhydride in the presence of an acid catalyst, acetylsalicylic acid, or aspirin, is produced according to the following equation. Acetylsalicylic acid asa, also known as aspirin, acts by irreversibly inhibiting the platelet cyclooxygenase cox enzyme, resulting in inhibition of platelet thromboxane a2 txa2 synthesis. Aspirin given shortly after a heart attack decreases the risk of death. Synthesis of acetylsalicylic acid aspirin acetic anhydride and salicylic acid react to produce acetylsalicylic acid and acetic acid. Synthesis of aspirin acetylsalicylic acid objectives aspirin, the wonder drug, is an important chemical worldwide. Reaction for the ferric chloride test using salicylic acid 3. For this reason, it is industrially synthesized on a massive scale, producing up.
Pdf this aim of this experiment focuses on the synthesis of pure aspirin acetylsalicylic acid from ethanoic anhydride and salicylic acid while. Reaction for the ferric chloride test using acetylsalicylic acid 4. Synthesis of acetylsalicylic acid dan jones, josh schmidt abstract acetylsalicylic acid, commonly known as aspirin, is considered to be the most successful pharmaceutical product in the world. Acetylsalicylic acid aspirin, c9h8o4 aspirin acetylsalicylic acid is a versatile drug that is consumed in huge quantities worldwide. Aspirin, also known as acetylsalicylic acid asa, is a medication used to reduce pain, fever, or inflammation. Mixture is heated for 10 to 15 min to complete reactions. We will prepare aspirin by reacting salicylic acid 1 with an excess of acetic anhydride 2 to produce aspirin 3 and acetic acid 4. The solid aspirin product will be separated from the reaction mixture by. It is made commercially employing the same synthesis used here. Expt 80 synthesis of acetylsalicylic acid aspirin fromk. Introduction aspirin, chemically known as acetylsalicylic acid, is the most commonly used antiinflammatory drug. Acetylsalicylic acid, marketed under the trade name aspirin by the bayer company, is one of. Experiment 8 synthesis of aspirin aspirin is an effective analgesic pain reliever, antipyretic fever reducer and antiinflammatory agent and is one of the most widely used nonprescription drugs. Apr 12, 2020 acetylsalicylic acid asa is better known to most people by its common name, aspirin.
Sulphuric acid is added to the mixture and is swirled. As the reaction proceeds, the solid salicylic acid disappears and the acetylsalicylic acid product remains dissolved in the hot solution. We will prepare aspirin by reacting salicylic acid 1 with an excess of acetic. Aspirin is also used longterm to help prevent further heart attacks, ischaemic strokes. Moreover, the salicylic acid is a compound derived from hydrolysis of acetylsalicylic acid aspirin. Aspirin acetylsalicylic acid is a painrelieving compound. This method of forming acetylsalicylic acid is an esterification reaction. It enters the bloodstream where it interferes with the synthesis of prostaglandins and irreversibly binds to an enzyme called cyclooxygenase 2. Titrate potentiometrically the acetylsalicylic acid with a strong base and. The excess acetic anhydride is then decomposed with water to form acetic acid. Synthesis of aspirin aspirin is the single most manufactured drug in the world. Aspirins chemical name is acetylsalicylic acid, and it is synthesized from the reaction of acetic anhydride with salicylic acid in the presence of phosphoric acid as a catalyst. Nevertheless, the paracetamol has showed antioxidant activity in vitro while the acetylsalicylic acid does not present it. Add the anhydride drop wise to the flask containing acid using a pasteur pipette.
Aspirin hc9h7o4 or c9h8o4 cid 2244 structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities. Instead of using acetic acid, acetic anhydride was used as solvent since the anhydride reacting with water to form acetic acid tends to drive the reaction to the right. Synthesis of aspirin experiment chemistry libretexts. In this twoweek experiment the important area of organic chemistry will be illustrated by the preparation and characterization of two compounds. In the fume hood, add five drops of concentrated acid to the flask containing the salicylic acid and acetic anhydride and swirl to mix everything thoroughly. Once all solid has disappeared all the salicylic acid has. It is the twostep synthesis of aspirin starting from oil of wintergreen. To prepare aspirin, salicylic acid is reacted with an excess of acetic anhydride.
The temperature of an alcohol thermometer was equilibrated in a beaker of room temperature tap. In this experiment aspirin, also known as acetylsalicylic acid, was synthesized from salicylic acid and acetic anhydride. Fisher scientific one reagent lane fair lawn, nj 07410. In todays experiment you synthesized the substance acetosalicylic acid aspirin from acetic anhydride and salicylic acid. Table of results for the ferric chloride test including title, all 4 samples, and initial and final observations 5. Reaction for esterification of salicylic acid to form acetylsalicylic acid 2. Salicylic acid cooh o c o ch3 acetylsalicylic acid aspirin fig. Aspirin is an analgesic pain reliever, an antipyretic fever reducer, and antiinflammatory medicine. This experiment teaches the concept of ester formation using a very reactive acid derivative acetic anhydride with an appropriate alcohol.
A combination of sodium salicylate and acetyl chloride, this medication is the first nonsteroidal antiinflammatory drug to be developed, and its been in use for over a century. Jan 25, 2018 your synthesis converted most, but not all, of the salicylic acid into acetylsalicylic acid. You will mix iron iii nitrate with salicylic acid in your aspirin sample to complex the salicylic acid, which is a bluishpurple colour. This aspirin should be more pure than the original. Acetylsalicylic acid asa is better known to most people by its common name, aspirin. Ir spectra of the starting material salicylic acid and the product acetosalicylic acid aspirin are attached. Specific inflammatory conditions which aspirin is used to treat include kawasaki disease, pericarditis, and rheumatic fever. Dissolve the solid acid by gently swirling the mixture, then add 10 drops of concentrated 85% phosphoric acid h 3 po 4. Experiment 22 synthesis of aspirin and oil of wintergreen. In 1853, gerhardt neutralized salicylic acid by buffering it with sodium sodium salicylate and.
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