Ppt synthesis of aspirin powerpoint presentation free to. Revisiting aspirin, paracetamol and ibuprofen juniper publishers. Ask any medical student and he or she will tell you that aspirin reduces fever. Aspirin synthesis mechanism organic chemistry youtube. Synthesis of aspirin lab report 2989 words bartleby. Many different laboratory techniques are used in the synthesis of aspirin. Tap the closed end of the capillary onto the bench top, so that the aspirin crystals work their way to the bottom.
The percent yield of the crude product will be determined for this reaction. Aspirin is a pain relieving compound that most students will be familiar with, thus its synthesis gives students an insight into how chemistry is used in reallife applications. Esterification of salicylic acid and acetic anhydride to aspirin with h2so4 the percent yield is then calculated based on the products weight in grams over the solved. Based on this, the mechanism of asa decomposition by a pilp reaction is presented. The process is a form of esterification reaction and thus is reversible. Aspirin is a drug which is widely used today to deal with the symptoms of many minor illnesses ranging from general relief from aches and pain. Jan 08, 2012 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.
In this experiment, the catalyst of phosphoric acid is used to catalyze the formation of aspirin, which can be seen in the mechanism of the reaction in figure 2. Heat the mixture at about 90 c in a hot water bath for about 5 minutes. He proved that aspirin and other nonsteroid antiinflammatory drugs nsaids inhibit the activity of the enzyme now called cyclooxygenase cox which leads to the formation of prostaglandins pgs that cause inflammation. Get a piece of filter paper that fits in the funnel, and place it flat in the funnel. While the ester green is formed from the esterification of an alcohol and a carboxylic acid. Furthermore, the acetylsalicylic acid will be in a free st. A useful synthesis of acetylsalicylic acid was developed in 1893, patented in 1899, marketed under the trade name of aspirin by the bayer company in germany. Much of this is believed to be due to decreased production of prostaglandins and txa2. The mechanism for the synthesis of aspirin using salicylic acid, acetic anhydride, acetylsalicylic acid, and acetic acid. Mix salicylic acid solid with acetic anhydride liquid and a catalytic amount of h2so4 heat for 10 min at 900c cool down to room temperature and add water crystallization solvent induce crystallization filter the crystals. The melting point of pure aspirin is 5c, and the melting point of salicylic acid is 158c. This reduces leukocyte adhesion, which is an important step in immune response to infection. Synthesis the method of synthesis today involves the reaction of salicylic acid and acetic anhydride in the presence of an acid catalyst such as sulphuric acid or phosphoric acid to give the products asa and acetic acid. The synthesis of aspirin is an organic chemistry experiment in many specifications for students of ages 1618 years.
The synthesis of aspirin may be achieved in one simple step, oacetylation of salicylic acid figure 1, which is incorporated into many undergraduate synthetic. Subcortical thalamus, hypothalamus and peripheral chemical mechanical sensitivity of receptors for pain. Aspirin synthesis and mechanism free download as pdf file. Aspirin can also directly scavenge hydroxyl radicals to form the 2,3 and 2,5dihydroxybenzoate derivatives, which themselves serve as markers of oxidative stress25 and quench oxyradical flux,26 and can acetylate the eamino groups of lysine residues in proteins,27 which prevents their oxidation. Uncoated aspirin tablets, consisting of about 90% acetylsalicylic acid. It is necessary to consider resonance forms of intermediate structures. The name aspirin was invented by the chemist, felix hofmann, who originally synthesized acetylsalicylic acid for bayer. Aspirin synthesis 7 mass spectrometry theoretical yield 1 mole of aspirin 1 mole salicylic acid x x 1 mole aspirin 180. Catalysts do not change the composition of the final product, however, and this is also visible in figure 2. In 1971, vane discovered the mechanism by which aspirin exerts its antiinflammatory, analgesic and antipyretic actions. A greener approach to aspirin synthesis using microwave. Aspirin given shortly after a heart attack decreases the risk of death.
Introduction organic compounds are a certain type of compounds that contain carbon. Ppt synthesis of aspirin powerpoint presentation free. Aspirin s ability to suppress the production of prostaglandins and thromboxanes is due to its irreversible inactivation of the. Chemistry 51 experiment 11 synthesis and analysis of aspirin. Deacetylated by estrase to producing active salicylate. Synthesis of aspirin synthesis purification characterization.
The name aspirin was invented by the chemist, felix hofmann, who originally synthesized acetylsalicylic acid for. Aspirin has been widely used as analgesic and antiinflammatory drug. In this case, an acetyl group was added to salicylic acid, a naturally occurring compound with significant pharmaceutical value. Antiinflammatory inhibition of the synthesis of prostaglandins. Contents some background the chemistry of aspirin physical properties synthesis mechanism ir and nmr spectroscopy biological activity brand names conclusion some background 1897 in germany, bayers felix hoffmann develops and patents a process for synthesising acetyl salicylic acid or aspirin. It is expected that the students will consider a reaction mechanism. The aspirin story from willow to wonder drug desborough. Experiment to synthesize, purify and determine percentage yield of.
The lab experiment was divided into parts and the synthesis of the aspirin occurred during the first week. The starting material, for this synthesis, is 2hydroxybenzoic acid salicylic acid. Calculate the theoretical yield for the esterification reaction synthesis of aspirin from salicylic acid. There is currently insufficient evidence to show that aspirin helps to fight infection. The production of this ester can be reversed by a hydrolysis reaction. Aspirin use and reduced risk of fatal colon cancer. Aspirin synthesis and mechanism aspirin acetic acid.
Chm230 aspirin synthesis lab introduction aspirin is. Aspirin s 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. Propose a reasonable reaction mechanism that supports your answer. Recently, it was elucidated that aspirin have anticoaggregatory effect in low dose. Conventional management of thrombosisbased disorders includes the use of heparin, oral anticoagulants, and the preferred antiplatelet agent aspirin. Biological activity analgesic painkiller antipyretic fever reducer antiinflammatory inhibition of the synthesis of prostaglandins side effects. Synthesis workingup hplc reaction control purity control experimental arrangement. The use of aspirin had its origin in the 18th century, when it was found that an extract from the. A phenol group is distinguished as the oh that is coming off a ring system. The reaction that is used for the synthesis of aspirin shown below figure 4. Synthesis and biological activity of aspirin derivatives. In aspirin there is a carboxylic acid and ester functional group each attached to a separate carbon. Synthesis of aspirin derivatives was prepared by esterification in the presence. Additionally, aspirin induces the formation of noradicals in the body, which have been shown in mice to have an independent mechanism of reducing inflammation.
Draw the arrowpushing mechanism for the synthesis of aspirin from salicylic acid. He proved that aspirin and other nonsteroid antiinflammatory drugs nsaids inhibit the activity of the enzyme now called. This study was carried out to investigate the synthesis of aspirin derivatives from aspirin and aromatic compound of antioxidant and its biological activities. Antiplatelet therapy has been documented to reduce risks of cardiovascular disease after acute myocardial infarction, coronary artery bypass graft, and in chronic atrial fibrillation patients, amongst other risk factors. Obtain a capillary tube from your instructor, and gently press the open end into the pile of aspirin crystals on the paper so that a few crystals of aspirin enter the capillary tube.
The purpose of this lab was to demonstrate the ability to easily alter the molecular structure of a compound to greatly increase its utility. You may abbreviate the aromatic ring ar in the intermediates. Each of the four levels take approximately 30 minutes to complete and are designed to be used as prelab activities in class or as homework. For the fecl 3 test, the samples do not have to be dry. History of discovery aspirin has a great history of development which. This process, as performed in this experiment, reacts a hydroxyl group on the salicylic acid with acetic anhydride. Aspirin is one of the most successful nonprescription drugs ever made. The mechanism for this synthesis provides examples of three major classes of chemical reactions. Consult msds for safety information on all the chemicals you plan to use. Chm230 aspirin synthesis lab kotz, treichel, townsend, chemistry and chemical reactivity. Connect the other end of the rubber tubing to an aspirator in the lab. Acetylsalicylic acid binds to and acetylates serine residues in cyclooxygenases, resulting in decreased synthesis of prostaglandin, platelet aggregation, and inflammation.
Aspirin is an orally administered nonsteroidal antiinflammatory agent. Aspirin is a nonsteroidal antiinflammatory nsaid drug which can be used to treat pain, fever, inflammation and heart diseases. New insights into the mechanisms of action of aspirin and its use in the prevention and treatment of arterial and venous thromboembolism ymer h mekaj,1,2 fetije t daci,2 agon y mekaj3 1institute of pathophysiology, faculty of medicine, university of prishtina, 2department of hemostasis and thrombosis, national blood transfusion center of kosovo, 3clinic of neurosurgery, faculty of medicine. A filter crucible and mortar and pestle were obtained from the instructor. Acetylsalicylic acid asa is a pharmacologically active compound. Aspirin c 9h 8o 4 is an ester formed of two substances, acetylsalicylic salicylic acid and ethanoic anhydride, by a condensation reaction. Attach a condenser to your flask to create a reflux apparatus. Background the production of aspirin is easily accomplished by the esterification of salicylic acid. This started to become clearer later in the 19th century as scientific techniques improved.
Interestingly, aspirin was once a trademark belonging to bayer. Synthesis of aspirin in the first part of the experiment, aspirin was synthesized. Clamp a sidearm flask to the ring stand, and connect a piece of rubber tubing to the sidearm. The carboxylic acid red comes from a carbonyl and hydroxyl group joining. Introduction aspirin is a drug which is widely used today to deal with the symptoms of many minor illnesses ranging from general relief from aches and pain. Inhibition of prostaglandin synthesis as a mechanism of action for aspirin like drugs. Daniels organic chemistry 2121 11 february 2014 synthesis of aspirin salicylic acid derivatives, or salicin, are found in the bark of the willow tree in the 5th century b. Inhibition of prostaglandin synthesis as a mechanism of action for aspir. Esterification of salicylic acid and acetic anhydride to aspirin with h2so4 the percent yield is then calculated based on the products weight in grams over the solved yield based on the limiting reagent to determine purity.
However, the concentrations of aspirin required to obtain a beneficial effect in asthma are higher than those required to inhibit cox2527. This agent exhibits analgesic, antipyretic, and anticoagulant properties. 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. This beaker, 2 graduated cy linders, a distilled water wash bottle, medicine. This dense tubular membrane system plays an important role in platelet activation, and is the principal site for eicosanoid synthesis in platelets. This drug was named aspirin and became the most widely used medicine of all time. The process involves a multistep mechanism that is. Nov 02, 2015 lower doses of aspirin have also shown to reduce the risk of death from a heart attack, or the risk of stroke in some circumstance. Aspirin causes several different effects in the body, mainly the reduction of inflammation. International journal of research in pharmacy and science. The name organic is derived from the oncebelieved assumption that they could only be isolated from.
Reaction mechanism in the synthesis of aspirin free download as powerpoint presentation. Aspirin is also used longterm to help prevent further heart attacks, ischaemic strokes. Reaction mechanism in the synthesis of aspirin chemical. It was thin, short white crystals and had a melting point range or 154155 degrees celsius. Full text new insights into the mechanisms of action of. Put a buchner funnel with a rubber stopper in the flask. Comment on the purity of your aspirin based on its melting point. The aspirin story from willow to wonder drug desborough 2017. Place 1 ml of ethanol and 2 drops of fecl 3 solution in each tube. To be able to show the reaction mechanism in the synthesis of aspirin.
Jan 20, 2017 while aspirin was an extraordinarily successful product, little was known about its mechanism of action. Inflammation and the mechanism of action of antiinflammatory drugs. Pg,s synthesis at thermoregulatory centre hypothalamus and peripheral target tissues. The demonstration that aspirin inhibited prostacyclin synthesis paved the way for the future development of nonsteroidal anti. Figure 1 synthesis reaction for aspirin 1 after the crystals are formed, the percent yield will be calculated before the analysis is done. Aspirin, also known as acetylsalicylic acid asa, is a medication used to reduce pain, fever, or inflammation. Mar 15, 2017 the most recognized mechanism of action of aspirin is to inhibit the synthesis of prostaglandins but this by itself does not explain the repertoire of antiinflammatory effects of aspirin. The method described before is that followed by most manufacturers to make this chemical.
Mechanism of action aspirin exerts its effect primarily by interfering with the biosynthesis of cyclic prostanoids, ie, thromboxane a2 txa2, prostacyclin, and other prostaglandins. Aspirin causes several different effects in the body, mainly the reduction of inflammation, analgesia relief of pain, the prevention of clotting, and the reduction of fever. Calculate the mmol of salicylic acid and acetic anhydride used in the reaction. New insights into the mechanisms of action of aspirin and its use in the prevention and treatment of arterial and venous thromboembolism ymer h mekaj,1,2 fetije t daci,2 agon y mekaj3 1institute of pathophysiology, faculty of medicine, university of prishtina, 2department of hemostasis and thrombosis, national blood transfusion center of kosovo, 3clinic of neurosurgery, faculty of. The mechanism of this reaction can be understood by examining the lewis structures of each reagent.
The process involves a multistep mechanism that is easily catalyzed by excess protons. Synthesis of aspirin aspirin is the single most manufactured drug in the world. Aspirin synthesis mechanism using acetyl chloride organic. There is some evidence that aspirin is effective at preventing colorectal cancer, though the mechanisms of this effect are unclear pain. Catalysts free fulltext assessment of degradation behavior for. After germany lost world war i, bayer was forced to give it up as part of the treaty of versailles in 1919. Specific inflammatory conditions which aspirin is used to treat include kawasaki disease, pericarditis, and rheumatic fever.
Introduction aspirin c 9h 8o 4 is an ester formed of two substances, acetylsalicylic salicylic acid and ethanoic anhydride, by a condensation reaction. Synthesis of aspirin acetylsalicylic acid objectives aspirin, the wonder drug, is an important chemical worldwide. In a round bottom flask, mix 8 mg of salicylic acid with 1 drop of 85% phosphoric acid and 0. Background aspirin acetylsalicylic acid belongs to a class of drugs known as nonsteroidal antiinflammatory drugs nsaids, which work by blocking the synthesis of prostaglandins in the body. Dec 08, 2014 synthesis and characteristics of aspirin acetylsalcylic acid summary. Synthesis of aspirin synthesis purification characterization aspirin. It is expected that the students will consider a reaction mechanism that proposes a charge. The synthesis of aspirin using acetyl chloride is an old method to synthesize aspirin and is often not favored because of the side product of hydrochloric ac. Aspirin organic chemistry salicylic acid acetic anhydride mechanism synthesis physical chemical properties. A free powerpoint ppt presentation displayed as a flash slide show on id. These resonance forms will help you understand why a partial positive charge appears on the carbon atom in acetic anhydride and how this results in a new bond forming at that.
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