Abstract:
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
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Hofmann worked for Bayer, which then named acetylsalicylic acid compound aspirin. Aspirin became commercially available in 1899 and today it is estimated that over a trillion aspirin tablets have been consumed by those in need of its curative effects.
In this experiment aspirin was synthesized from salicylic acid and acetic anhydride.
Salicylic acid was esterfied using acetic acid and sulfuric acid acting as a catalyst to produce acetylsalicylic acid and acetic acid. 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. 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. Sulfuric acid serves as the acid catalyst since its conjugate base is a strong deprotonating group that is necessary in order for this reaction to be reversible. The need for the strong conjugate base is the reason why other strong acids such as HCl is not used since its conjugate base Cl- is very weak compared to HSO3-. After the reaction was complete some unreacted acetic anhydride and salicylic acid was still be present in
At room temperature (25°C), esterification reactions are relatively slow, therefore requiring the rate of the chemical reaction to be increased for the products to be formed efficiently. This is implemented, by using a catalyst, such as concentrated sulphuric acid (H2SO4 (aq)), as well as by heating the mixture: using a heating mantle. As a result, the energy of the reactants can be greater than the activation energy, increasing the rate of reaction. Hence, as the reactants are relatively volatile, so reflux apparatus such as a pear-shaped flask and a Liebig condenser were used, to minimise the amount of reactants lost, as well as allow the reaction to take place at the highest temperature possible. In addition, boiling chips were added prior to reflux, to prevent bumping and a decrease a loss of volatile reactants, during the reflux
An ester was synthesized during an organic reaction and identified by IR spectroscopy and boiling point. Acetic acid was added to 4-methyl-2-pentanol, which was catalyzed by sulfuric acid. This produced the desired ester and water. After the ester was isolated a percent yield of 55.1% was calculated from the 0.872 g of ester recovered. This quantitative error was most likely due to product getting stuck in the apparatus. The boiling point of the ester was 143° C, only one degree off from the theoretical boiling point of the ester 1,3-dimethylbutyl, 144 ° C. The values of the
Acetaminophen was added to the British Pharmacopoeia in 1963. It became very popular once it was released. The reason why it became very popular was because it had very few side effects, unlike aspirin which irritated the stomach. The United States use generic versions of the drug. The drug acetaminophen is called paracetamol in countries located outside of the United
The purpose of refluxing the reaction was to break the bond in the p-acetaminophen and acetic anhydride at the same time the condenser prevent some molecule to escape though evaporation by capturing it and return it into the reaction vessel. The heat was necessary to break bond in P-acetaminophen and in acetic anhydride by increasing the rate of reaction and bringing molecules closer to the activation energy. Product isolation was performed by cooling the solution, and filtered it to isolate the crystals of the products by using Hirsch funnel. This crude product was then purified through recrystallization technique and by using Craig tube. The final process was to identify the product by using dig melt machine to find out the melting point
Reflux Introduction The purpose of this lab was to perform our first organic synthesis of an acetylation reaction through the technique of refluxing. Reflux is a technique that involves heating a mixture to the boiling point temperature of a solvent, causing the solvent to condense back into the reaction round bottom flask by using a condenser. Refluxing is a very efficient way of maintaining a solution at a constant temperature. In order to avoid losing any of the solvent, a water-jacketed column was used.
The purpose of this lab was to synthesize the ester isopentyl acetate via an acid catalyzed esterification (Fischer Esterification) of acetic acid with isopentyl alcohol. Emil Fischer and Arthur Speier were the pioneers of this reaction referred to as Fischer Esterification. The reaction is characterized by the combining of an alcohol and an acid (with an acid catalyst) to yield and ester plus water. In order to accomplish the reaction, the reactants were
Based on the advantages of ester, the current research will allow it to expand into everyday life as in lubrication by providing cleaner operation due to its unique properties. (Schaefer). The theory of this experiment is based on esterification which is a type of organic reaction. In an esterification reaction, acids and alcohols are heated in the presence of Sulfuric acid as the catalyst. This type of reaction is slow and can be reversible by through a hydrolysis which is the addition of water.
Discussion: In this experiment we added salicylic acid to 2.0 ml acetic anhydride for the molecules to react to produce aspirin. The 85% concentrated phosphoric acid was added to act as an acid catalyst to lower the required activation energy for the reaction. We then allowed the reaction to stand for about 10 minutes to allow the phosphoric acid to spread through the solution. We than heated the solution to add energy to the system to obtain the activation energy needed for the reaction. After heating the solution, letting the solution chill allowed the aspirin to crystalize into a solid. Vacuum filtration was use to isolate only aspirin on to the filter paper to be weighed to record the mass of aspirin produced.
In this experiment, I collected the willow bark then boil it using the heating flask. I used the rotary evaporator to separate water from the crude product. I further used centrifugation and crystallization of the compound. At last, I compared my aspirin sample with an analgesic aspirin using the NMR at Boston College.
In 1899, a German chemist named Felix Hoffmann, who worked for a Germany company called Bayer, rediscovered Gerhardt’s formula. Felix Hoffmann made some of the formula and gave it to his father who was suffering from the pain of arthritis. When he saw that there were good results he convinced Bayer to market the new drug to their company. Aspirin was first sold as a powder. According to Bayer's biography of Hoffman, it was 'mostly by chance' that the chemist Felix Hoffmann succeeded in mixing salicylic acid with acetic acid to create what is now widely recognized as something that mostly everyone knows and uses when in pain. It is a well-known medicine. Hoffmann didn’t like the alternative treatment, a juice from the willow tree bark that had been used for centuries as a painkiller and treatment for fever, but it had a lot of negative side effects, including nausea, gastro-intestine irritation,
Acetylsalicylic acid (ASA) or aspirin is a drug that is commonly used as an analgesic, to relieve pain without a loss of consciousness, to reduce fever and it is also used as an anti-inflammatory drug. It is salicylate drug and its salicylate was originally extracted from the willow bark plant which was discovered by Hippocrates, a very long time ago (1). After many research and trials it has come under consideration that Aspirin can be used as a preventive and as an anti-inflammatory drug for cardiovascular diseases, ischemic stroke, atherosclerosis, and also for prevention from cancers (3).
In this current time, a good number of people have only seen Salicin as a pill, so this paper stands to show how salicin developed from a leaf to a pill. There were numerous people from different countries and centuries involved in the development of Salicin. The person who formatted salicin in its present form is Felix Hoffman. Felix Hoffman kept Salicin in the pill form it had already been in, except he somewhat improved it. Felix Hoffman’s Salicin was enhanced due to the fact that the positive effects outweighed the negative ones. Before Hoffman, there was Charles Frederic Gerhardt. Gerhardt made Aspirin by deactivating salicylic acid and mixing sodium salicylate and acetyl chloride. Gerhardt, was not the first person to formulate Salicin into an acid, but he was the last. There was a version of Salicin that was an acid before Gerhardt’s. The needle acid form was developed by Raffaele Piria. In this form Piria would divide the salicin and eventually turn it into an acid. Earlier, a scientist named Henri Leroux, found a way to obtain Salicin from the willow tree bark. Preceding him though, is Johann Buchhner. Buchhner, first made salicin into an acid, in addition to naming it. Finally,
Not until 1828 was Johann Buchner, professor at Munich University, able to isolate the substance from the tannis in willow trees, to which he gave the name of salicin. A purer form of salicin was developed later in 1829, and then its mass pharmaceutical production began. It was not until scientists started to understand the effects of this new product, that they realized its side effects were greater than its benefits. By understanding the connection between evolution and biotechnology, scientists were able to modified the new drug in a way that was safer for consumers to take, and start its mass production again, which is what we know as Aspirin
It is thought that accident Greece used willow leaves to reduce fever and pain (How Aspirin Is Made - Background, History, Raw Materials, The Manufacturing Process of Aspirin.) However aspirin was not mixed together or created until 1897 by Felix Hoffmann. It was invented to help people by reducing fever and pain, and used to reduce heart attacks (Aspirin History - Invention of Aspirin). Aspirin however was not made to withstand certain conditions. Aspirin will melt at 136ºC or 276.8ºF, and will boil at 140ºC or 284ºF. Aspirin will decompose in hot water, and will break down in moist air. It is best to keep aspirin in room temperature or dry air (ACETYLSALICYLIC ACID (ASPIRIN)).
During 1915 World War I the British required aspirin nonetheless it was prepared by the Germans (Co &Bayer). Thus the British government presented a £21,000 return to anybody who could improve a practicable developed method. This was attained by George Nicholas, a pharmacist in Melbourne, who consequently provided his pill the name Aspro. 1995s More than 10~12 million kilograms of aspirin are prepared in the US every year. Today aspirin is not just only used as a drug then has also been planned as actual in decreasing the occurrence of heart sickness.