Acetylsalicylic acid synthesis mechanism. Synthesis and Purification of Acetylsalicylic Acid 2022-10-08

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Acetylsalicylic acid, more commonly known as aspirin, is a widely used pain reliever and anti-inflammatory agent. It was first synthesized by the German chemist Felix Hoffmann in 1897, and has since become an integral part of many households around the world. The synthesis of aspirin involves the acetylation of salicylic acid, a compound that occurs naturally in plants such as willow bark and meadowsweet.

The synthesis of aspirin begins with the conversion of salicylic acid into its sodium salt, which is more reactive and easier to work with. This is typically done by reacting salicylic acid with sodium hydroxide in an aqueous solution. The resulting sodium salicylate can then be acetylated using acetic anhydride as the acetylating agent.

The acetylation reaction is typically carried out in the presence of a small amount of an acidic catalyst, such as sulfuric acid or hydrochloric acid, to facilitate the transfer of the acetyl group from acetic anhydride to the salicylic acid. This reaction proceeds via a nucleophilic substitution mechanism, in which the acetyl group of the acetic anhydride acts as a nucleophile and attacks the electrophilic carbon atom of the salicylic acid.

The acetylated product, known as acetylsalicylic acid, can then be isolated from the reaction mixture by techniques such as crystallization or filtration. It is typically purified by recrystallization to remove any impurities or contaminants that may be present.

The synthesis of aspirin is a simple and efficient process that has been widely used for over a century. In addition to its use as a pain reliever and anti-inflammatory agent, aspirin has also been shown to have beneficial effects on the cardiovascular system, making it a popular choice for preventing heart attacks and strokes. Overall, the synthesis of acetylsalicylic acid has had a significant impact on the field of medicine and has greatly improved the quality of life for many people around the world.

Acetylsalicylic Acid

acetylsalicylic acid synthesis mechanism

The initial supersaturation was 1. Beran, Lab Manual for Principles of General Chemistry, 9th and 8th Ed. Phenytoin and sodium valproate: Enhanced effect. As a result, the solid product dissolves in basic solution and then recrystallizes in acid solution. All the functional groups identified by the experimental and literature IR spectrum align with the acetylsalicylic molecule. As a result the vapour or gases formed in the reaction could have travelled up into reflux tube and left the system. One popular drug that does both is aspirin.

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Synthesis of Acetyl Salicylic Acid (Aspirin) Essay Example

acetylsalicylic acid synthesis mechanism

Place in a 125-ml Erlenmeyer flask. However compared to the theoretical yield it is evident that there was a great loss of aspirin that should have been formed. Wait and observe a little longer until all of the aspirin has melted. When the aspirin enters the stomach, some of it absorbs within the stomach. Include phase subscripts: aq , liq , and g. Adverse Effect : Gastrointestinal irritation, gastric bleeding and ulceration, bronchospasm, interstitial nephritis, renal papillary necrosis, hepatotoxicity, hypoglycemia, pulmonary edema.

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Hydrolysis of Aspirin

acetylsalicylic acid synthesis mechanism

Loop Diuretics: Salicylates may diminish the diuretic effect of Loop Diuretics. Rinse the crystals collected in the funnel with 5 — 10 ml of 5 oC DI water. The molecular form of aspirin reacts as a carboxylic acid, and will form a water-soluble salt upon its reaction with sodium carbonate. Finally, the leaving group is acetic acid, rather than chloride. It was not digital and did had a disk shaped scale. It is taken orally as it is well absorbed by the gastrointestinal system. Severe hepatic impairment: Avoid use.

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Aspirin (Synthesis and Mechanism)

acetylsalicylic acid synthesis mechanism

Balance:The balance used to calculate the mass of the wet and dry product along with the beaker was considerably outdated. Aspirin is more soluble in basic alkaline solutions, so it readily dissolves in the duodenum which is the first part of the intestine. As a result the action of condensing was not 100% efficient. Reye's Syndrome may develop. Salicylic acid can be used to create two different types of esters.

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Victoriana Magazine

acetylsalicylic acid synthesis mechanism

The reactants: In the experiment that was carried out the reactants were not measured by the apprentices. ACE Inhibitors: Salicylates may diminish the antihypertensive effect of ACE Inhibitors. Correspondingly, an excess of methanol will form methyl salicylate, which is also an analgesic. In the small intestine the aspirin solubility is improved, whereas the lower down you go through the small intestine the higher the pH will be and by having a large surface area the absorption of aspirin would be increased. Make sure that the resulting solution is acidic blue litmus paper and that the aspirin has completely precipitated out. The Catalyzed Process Catalysis also occurs where an un-dissociated acid exists in the transition state of the reaction. Lipoxins halt neutrophil recruitment, adhesion, and infiltration; 150—152 reduce expression of genes upregulated by inflammatory responses; 153—156 stimulate prostacyclin 157 and nitric oxide generation; 158 and reduce angiogenesis.

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Acetylsalicylic

acetylsalicylic acid synthesis mechanism

Provide balanced reactions that show how four or more molecules can bond together in a single chain. Reaction Aspirin can undergo hydrolysis, making it not as effective if it's exposed to water for extended periods of time. It is used in conditions such as fevers, prevention and treatment of thrombosis and embolism, and for prevention of ischemic abnormalities and cerebral blood circulation. Chronic salicylism patients will have more profound clinical effects at lower serum salicylate levels compared to patients with acute overdoses. If not, ensure that the solution is acidic with blue litmus or pH paper. These can be found under the hypothesis subheading. Aspirin is widely used for head and neuralgic pains, rheumatic conditions, painful symptoms of various etiologies, and eliminating painful feelings during menstruation.

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1: Synthesis of Aspirin (Experiment)

acetylsalicylic acid synthesis mechanism

The resulting solution was gently mixed. For example, in water, the solubility of aspirin increases as temperature increases. Were the particles could have been stuck would have meant water could not travel to that area therefore cooling was not able to take place here. These TLC plates were put into a developing chamber, in this case, a jar, containing a one to one ratio of Ethyl Acetate and Hexane. Dispose of product in the appropriately labeled waste jar, and discard the filter paper.

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Synthesis of Acetylsalicylic Acid

acetylsalicylic acid synthesis mechanism

Aspirin acetylsalicylic acid is an aromatic compound containing both a carboxylic acid functional group and an ester functional group. Acetylsalicylic acid will react with sodium bicarbonate to form a water- soluble sodium salt, whereas the polymer remains insoluble. Interaction : Anticoagulants: Increased risk of bleeding. Our academic experts are ready and waiting to assist with any writing project you may have. Therefore the balance did not have a very good precision and would give a percentage error in the reading.

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Synthesis and Purification of Acetylsalicylic Acid

acetylsalicylic acid synthesis mechanism

No dosage adjustments are recommended. Therefore you should get a temperature range of the aspirin Hazard and Risk Analysis: Included with the report is the MSDS data sheet. The phenolic ester bond is susceptible to hydrolysis, especially at alkaline conditions. High dose ingestion may cause salicylism characterised by tinnitus, respiratory acidosis and finally coma. It can therefore undergo two different types of esterification reactions, creating an ester either with the hydroxyl or with the acid. The technical name of the active ingredient in aspirin is acetylsalicylic acid.

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