E29 esterification preparation of aspirin acetylsalicylic. Once acetylsalicylic acid is absorbed from the intestine, it is converted back to salicylic acid. 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. Well, salicylic acid is similar to the acetylsalicylic acid in aspirin, and is found naturally in some plants, such as the willow tree. Organic chemistry reactions and synthesis medicinal chemistry chromatography. Synthesis of acetylsalicylic acid aspirin using acid. As the reaction proceeds, the solid salicylic acid disappears and the acetylsalicylic acid product remains dissolved in the hot solution.
Synthesis of salicylic acid from oil of wintergreen. Salicylic acid cooh o c o ch3 acetylsalicylic acid aspirin fig. Synthesis of acetylsalicylic acid occurs by protonation of carbonyl co group, and a nucleophilic attack of oh on the acetic anhydride. Williamson, macroscale and microscale organic experiments, 2nd ed. Uvdirected purification of a smallscale organic synthesis. In the first experiment of this practical exercise, acetic anhydride reacts with salicylic acid to produce acetylsalicylic acid and acetic acid. Four peaks appeared between it is imperative that the benzaldehyde be from a newly opened shnthesis because of the ease of oxidation, producing benzoic acid, which will interfere with the reaction. Hplc conditions and spectral data for compounds 3a and 4a, spectral data for other selected compounds 3e, 3f and 4f. A structure and antioxidant activity study of paracetamol and. Acetylsalicylic acid does not have the bad taste and stomach problems of salicylic acid. However, this reaction is slow and has a relatively low yield. 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. Pdf this aim of this experiment focuses on the synthesis of pure aspirin. For this reason, it is industrially synthesized on a massive scale, producing up to 1800 kg 10,000 moles per batch.
It is widely used as an analgesic pain reliever and fever depressant. 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. Biological basis and clinical implications of acetylsalicylic acid. Pdf crystallization and morphological characteristics of. Studies of different types of aspirin by spectrophotometric methods gabriela motan,a aurel puia adepartment of chemistry, al. This application note describes the smallscale purification of a synthesized drug product, acetylsalicylic acid using preparativescale liquid chromatography. Most drugs are chemical compounds, which are described as organic compounds. Moreover, the salicylic acid is a compound derived from hydrolysis of acetylsalicylic acid aspirin. On the contrary, the salicylic acid does not present this effect at the same condition and concentration. Aspirin acetylsalicylic acid is an important antiinflammatory and analgesicpyretic drug. In this lab, we synthesized aspirin using both acid catalysis and base catalysis. Aspirin is a trade name for acetylsalicylic acid, a common analgesic. This file contains additional information such as exif metadata which may have been added by the digital camera, scanner, or software program used to create or digitize it. Process flow sheet for aspirin synthesis free pdf file.
Process flow sheet for aspirin synthesis free pdf file sharing. 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. If acetic anhydride is used instead of acetic acid, the reaction is much faster and. Uvdirected purification of a smallscale organic synthesis author. Organic chemistry ii january 30, 20 synthesis of aspirin acetylsalicylic acid using acid and base catalysis. Pharmacokinetics and pharmacodynamics of acetylsalicylic acid. Introduction a starch called amylum is a natural polymer containing a large number of glucose units linked by glycosidic bonds. Aspirin can be made by reacting salicylic acid with acetic acid in the presence of an acid catalyst. 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. Chemistry 51 experiment 11 synthesis and analysis of aspirin. The mechanism for this synthesis provides examples of three major classes of chemical reactions. To synthesize aspirin from salicylic acid and acetic anhydride.
O acetylsalicylic acid is the prototypical analgesic used in the treatment of mild to moderate pain. Specific inflammatory conditions which aspirin is used to treat include kawasaki disease, pericarditis, and rheumatic fever. It enters the bloodstream where it interferes with the synthesis of prostaglandins and irreversibly binds to an enzyme called cyclooxygenase 2. Transitionmetallewis acid free synthesis supporting info. The phenol group on the salicylic acid forms an ester with the carboxyl group on the acetic acid. Once all solid has disappeared all the salicylic acid has. Jan 30, 20 synthesis of aspirin acetylsalicylic acid using acid and base catalysis chm 2211c. In 1853, gerhardt neutralized salicylic acid by buffering it with sodium sodium salicylate and acetyl chloride, creating acetylsalicylic acid. A small amount of a strong acid is used as a catalyst which speeds up the reaction. Acetylsalicylic acid is a wonder drug par excellence. It can therefore undergo two different types of esterification reactions, creating an ester either with the hydroxyl or with the acid. Sites of inhibition of platelet arachidonic acid aa synthesis by the acetyl and salicylate moieties of acetylsalicylic acid asa.
Synthesis of acetylsalicylic acid in choline chloride based. Salicylic acid the first person to do so was a french chemist named charles frederic gerhardt. Expu2019t 80 synthesis of acetylsalicylic acid aspirin synthesis of acetylsalicylic acid aspirin fromk. Acetylsalicylic acid, characterization, release, retroesteri. The name aspirin was invented by the chemist, felix hofmann, who originally synthesized acetylsalicylic acid for bayer. Replacing these potentially harmful, strong acids with naturally acidic soft drinks or. If the file has been modified from its original state, some details such as the timestamp may not fully reflect those of the original file. Balaguer 1department of physical sciences, college of science, polytechnic university of the philippines, sta. It is used quite often as an introduction to preparative organic chemistry. Metode ini dapat digunakan untuk menguji aktivitas. Aspirin, also known as acetylsalicylic acid asa, is a medication used to reduce pain, fever, or inflammation. 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. Synthesis of acetylsalicylic acid from salicylic acid and acetic anhydride in the presence of aci d, the c arbonyl oxygen o f acetic a nhydride are protonated, wherein increasing the. Before the production of synthetic aspirin, extracts of willow bark were used to treat some of the conditions that aspirin is used for today see history of aspirin.
Synthesis of acetylsalicylic acid aspirin from salicylic acid and acetic anhydride soriano, sosa, sualibios and tan department of chemistry, college of science, university of santo tomas, manila abstract this experiment was done in order to synthesize aspirin from the fischer esterification reaction of salicylic acid and acetic anhydride. Antiinflammatory inhibition of the synthesis of prostaglandins. In this activity you use ethanoic anhydride to convert 2hydroxybenzoic acid into aspirin. Synthesis of acetylsalicylic acid aspirin acetic anhydride and salicylic acid react to produce acetylsalicylic acid and acetic acid. The synthesis of aspirin is a common synthesis experiment. The excess acetic anhydride is then decomposed with water to form acetic acid. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. Salicylic acid, whose name comes from salix, the willow family of plants, was derived from willow bark extracts. The present study was designed to investigate the effects of acetylsalicylic acid and paracetamol given separately and in combination on total body and renal pge2 synthesis in healthy volunteers. Dec 20, 2011 the gh3 acyl adenylase family member pbs3 regulates salicylic aciddependent defense responses in arabidopsis.
About the thermal behavior of acetylsalicylic acid and aspirin. Synthesis of acetylsalicylic acid free essay example. Effects of acetylsalicylic acid and paracetamol alone and in. Acetylsalicylic acid is not very soluble in cold water 0. Dec 11, 2011 synthesis and purification of acetylsalicylic acid asa or aspirin background salicylic acid is a phenol as well as a carboxylic acid. The earliest known uses of the drug can be traced back to the greek physician hippocrates in the fifth century b. Synthesis of acetylsalicylic acid in choline chloride. In folk medicine, willow bark teas were used as headache remedies and other tonics. It has a few side effects for some people, yet it is safe enough to be sold without a prescription. Experiment 10 synthesis of acetylsalicylic acid purpose to synthesize acetylsalicylic acid asa or. Macroscale synthesis of acetylsalicylic acid 1alleyromae o.
Original document by kurt wittauer 3 in german 1899, translated. Thus, salicylic acid is limiting and a maximum of 0. Synthesis and purification of acetylsalicylic acid asa or. E29 preparation of aspirin acetylsalicylic acid and thin. Cuza university iasi, 11 carol i bd, iasi 700506, romania abstract. A curriculum resource for post16 chemistry and science courses. Salicylic acid is an uncoupler and inhibitor of mitochondrial electron transport.
Aspirin given shortly after a heart attack decreases the risk of death. Pdf preparing a pure aspirin acetylsalicylic acid researchgate. Acetylsalicylic acid is an acetic acid ester derivative of salicylic acid. To prepare aspirin, salicylic acid is reacted with an excess of acetic anhydride. Aspirin hc9h7o4 or c9h8o4 cid 2244 structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities. Nevertheless, the paracetamol has showed antioxidant activity in vitro while the acetylsalicylic acid does not present it. Metode acetylsalicylic acid synthesis free pdf file sharing. Acetylsalicylic acid is not very soluble in water 0. Aspirin is the common name for the compound acetylsalicylic acid, widely used as a fever reducer and as a pain killer. Jan 21, 2016 in this video the synthesis of acetylsalicylic acid is shown. Pdf this aim of this experiment focuses on the synthesis of pure aspirin acetylsalicylic acid from ethanoic anhydride and salicylic acid while. Pharmacokinetics and pharmacodynamics of acetylsalicylic acid after intravenous and oral administration to healthy volunteers j nagelschmitz,1 m blunck,1 j kraetzschmar,1 m ludwig,1 g wensing,1 t hohlfeld2 1bayer healthcare ag, clinical pharmacology, wuppertal, germany.
Studies of different types of aspirin by spectrophotometric. 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. A simple technique for determining suitable separation conditions will also be described. 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. Since the stoichiometric molar ratio of salicylic acid to acetic anhydride is 1.
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