What are the natural and synthetic sources of aspirin?
- Apples
- Avocados
- Blueberries
- Broccoli
- Cauliflower
- Cherries
- Chili peppers
- Cucumbers
- Currants (including dried currants)
- Dates
What is the balanced equation for the synthesis of aspirin?
What is the balanced equation for the synthesis of aspirin? The reaction, using molecular formulas is C7H6O3 + C4H6O3 –> C9H8O4 + C2H4O2. The relevant molecular weights are 180 grams per mole for aspirin, and 138 grams per mole for salicylic acid. An excess of acetic anhydride is used in this preparation.
Why is sulfuric acid used in the synthesis of aspirin?
You are most likely preparing Aspirin from salicylic acid and acetic anhydride. This esterification reaction is catalysed with small amounts of a strong acid. (sulfuric acid in this case) If you add more than catalytic amounts, the sulfuric acid itself would hydrolyse the aspirin back to salicylic acid and acetic acid.
Why is acetic anhydride used in aspirin synthesis?
Acetic anhydride is the preferred acid derivative to synthesize aspirin commercially because the acetic acid produced in this reaction can be used again, by converting it back into acetic anhydride. In a 125-mL erlenmeyer flask, add 2 g salicylic acid (put the flask on the balance, and zero it).
What type of reaction is the synthesis of aspirin?
esterification reactionThe synthesis of aspirin is known in organic chemistry as an esterification reaction. This is a substitution reaction in which an alcohol (the –OH group in salicylic acid) reacts with acetic anhydride to form an ester, aspirin.
Is the synthesis of aspirin an esterification reaction?
The synthesis of aspirin is a simple esterification reaction. When salicylic acid is reacted with acetic anhydride (an acid derivative), the hydroxyl group of this salicylic acid is converted into an acetyl group.
What is the chemical equation for the synthesis of aspirin?
*The chemical equation corresponding to the synthesis reaction is: C7H6O3 + (CH3CO)2O → C9H804 + CH3COOH.
What is the hypothesis of the aspirin synthesis?
Hypothesis: I hypothesize that salicylic acid will react with acetic anhydride to produce acetylsalicylic acid (aspirin) and acetic acid (vinegar). Variables: Independent and controlled variables: The amount of sulfuric acid used for catalysis and the amount of salicylic acid and acetic anhydride.
What is an esterification reaction?
Some esters can be prepared by esterification, a reaction in which a carboxylic acid and an alcohol, heated in the presence of a mineral acid catalyst, form an ester and water: The reaction is reversible. As a specific example of an esterification reaction, butyl acetate can be made from acetic acid and 1-butanol.
Why is sulphuric acid used in aspirin synthesis?
Making aspirin This reaction would be very slow without a catalyst. In this case just a few drops of sulphuric acid added to the mixture means that there are some free positive hydrogen ions in the solution which can bind to the ethanoic anhydride. This makes it more active and speeds up the reaction.
How do you synthesize aspirin with salicylic acid?
SYNTHESIS OF ASPIRIN (acetylsalicylic acid) Place 2.0 g (0.015 mole) of salicylic acid in a 125-mL Erlenmeyer flask. Add 5 mL (0.05 mole) of acetic anhydride, followed by 5 drops of conc. H2SO4 (use a dropper, H2SO4 is highly corrosive) and swirl the flask gently until the salicylic acid dissolves.
How is aspirin made in chemistry lab?
To prepare aspirin, salicylic acid is reacted with an excess of acetic anhydride. A small amount of a strong acid is used as a catalyst which speeds up the reaction. In this experiment, sulfuric acid will be used as the catalyst. The excess acetic anhydride will be quenched (reacted) with the addition of water.
How is aspirin prepared from benzene?
Explanation: HOOC-CH-OH + ( CHCOCl + NaOH) →HOOC-CH-O-CO-CH + HCl. In this way, aspirin can be obtained from benzene.
What is the purpose of synthesis of aspirin lab?
The purpose of this lab was to synthesize Aspirin and measure the synthesized Aspirin's purity. By calculating the theoretical yield based on the original amount of Salicylic acid, one could determine the actual yield percentage of the reaction.
Why is water added to synthesis of aspirin?
After the reaction takes place, water is added to destroy the excess acetic anhydride and cause the product to crystallize. The aspirin is then collected, purified by recrystallization, and its melting temperature measured.
What is the function of aspirin?
Aspirin is in a group of medications called salicylates. It works by stopping the production of certain natural substances that cause fever, pain, swelling, and blood clots. Aspirin is also available in combination with other medications such as antacids, pain relievers, and cough and cold medications.
What is esterification aspirin?
The preparation consists of an esterification reaction catalyzed by acid (H2SO4 or H3PO4), where salicylic acid treated with acetic anhydride gives acetylsalicylic acid (aspirin). In this reaction, a hydroxyl group is converted to an ester, with acetic acid as a byproduct.
Why is aspirin ester?
Note that the salicylic acid has an organic acid functional group, and an alcohol group, on an aromatic hydrocarbon ring. The acetylsalicylic acid retains the organic acid functionality, but the alcohol has been modified, to form an ester group.
What is the purpose of Fischer esterification?
Fischer Esterification is an organic reaction which is employed to convert carboxylic acids in the presence of excess alcohol and a strong acid catalyst to give an ester as the final product.
What is the process of acetylation?
Acetylation is the process of transferring an acetyl group to the ε-amine group of the amino acid lysine on histone tails by HATs and acetyl coenzyme A as an acetyl group donor. Conversely, HDACs remove this acetyl group via hydrolysis reaction [10].
How is aspirin synthesized?
The main objective of the synthesis of aspirin lab was so produce aspirin (acetylsalicylic acid) through the reaction of salicylic acid and acetic anhydride. The methods used included recrystallization and scratching to produce a precipitate, which was then filtered to remove any excess moisture. The results displayed a percent yield of 34.3%, from a theoretical yield of about 1.97g of aspirin and an actual yield of approximately 0.68g of aspirin. Upon completion of the lab, analysis, and calculations, it is evident that the synthesis of aspirin is possible using these methods but that the yield will be relatively low.
What is the white precipitate?
When the salicylic acid and acetic anhydride were mixed, a white, powdery solution formed. When the sulfuric acid was added, a clear solution formed that produced heat. After heating, then cooling and scratching the solution, a white precipitate formed. The moisture in the precipitate was filtered overnight and what was left over was the desired product, aspirin.
What is the limiting reactant of aspirin?
The limiting reactant of the equation was salicylic acid. After the limiting reactant was determined, the theoretical yield of aspirin was calculated at approximately 1.97g. The actual yield was only around 0.67g, producing a percent yield of 34.3%. These results show that the methods used were only partially successful at achieving the goal of the experiment (synthesising aspirin). The findings showed that acetylsalicylic acid can be produced through a reaction between salicylic acid and acetic anhydride, but that a much lower yield will be produced. A higher yield could surely be achieved if several sources of error were to be eliminated.
How to remove aspirin from a flask?
Prepared a piece of filter paper in a filter funnel and filtered off the precipitate from the Erlenmeyer flask solution. After the liquid drained through the filter paper, washed the filtrate with two 10 mL portions of cold distilled water. When all the water had drained through, the filter paper was removed, and the solid (impure aspirin) was scraped into a dry 100 mL beaker using a clean scoopula.
What is the purpose of the aspirin lab?
The purpose of this lab is to synthesise acetylsalicylic acid (aspirin) by creating a reaction between acetic anhydride and salicylic acid. This was be accomplished through the use of recrystallization. Acetic anhydride and salicylic acid are mixed together, and then acidified by the addition of a few drops of concentrated sulfuric acid, ...
Why was the aspirin left overnight?
The accuracy of this lab could be improved with more precise equipment, allowing the experimenter to be more confident in the accuracy of the measurements obtained. While the aspirin was left overnight to allow time for the moisture to be filtered out, the air could have been a contaminant.
Why is sulfuric acid used in aspirin?
In the synthesis of aspirin, sulfuric acid is also used as a catalyst to speed up the reaction (Wikipedia, Sulfuric acid, 2013). Limiting reactants are important in chemical reactions because a reaction cannot proceed without all of the reactants. That is to say, a reaction can only occur until one reactant is used up (Kirk, 2013).
How to weigh salicylic acid?
Weigh out about 2.1 grams of salicylic acid on a piece of weighing paper. To do this, first tare a piece of weighing paper (This means to put a piece of paper on the balance and press the zero or tare button. Fig.1) Add some salicylic acid a little at a time onto the weighing paper until you have about 2.1 gram of it on the paper. It is OK to weigh a little extra mass (do not return excess salicylic acid to its container as this might contaminate the entire amount if your spatula is not perfectly clean). Record the mass of the solid. Place this solid into a 125-mL Erlenmeyer flask (other sizes may be acceptable).
How much sulfuric acid to add to a fume hood?
From this point on, keep your flask under the hood, because it now contains acetic anhydride (the vapors of acetic anhydride are very irritating). Add about 5 drops of concentrated sulfuric acid.
What is acetic anhydride?
Acetic anhydride is a lachrymator (its vapor irritates the eyes causing tears to flow). Keep it in the fume hood.
How to make a catalyst for sulfuric acid?
Add about 5 drops of concentrated sulfuric acid. This will be the catalyst for the reaction. Place the flask in the boiling water bath and clamp it in place. (Fig.2) Heat the reaction for at least 15 minutes. Put at least 60 mL of laboratory water into a 150mL beaker (or similar size).
What is the third test tube?
The third test tube is your Negative Control . Do not add any crystals to this test tube! The negative control shows you what to look for when a test is negative: in today’s analysis, the negative control shows you a color when no contaminating salicylic acid is present.
What to put in first test tube of aspirin?
Label the first test tube “Aspirin ” and add to this test tube a few of your aspirin crystals that you made today. Stir well.
How much water to add to acetic anhydride?
In 1 or 2 mL portions, add about 10mL cold water to the reaction, swirl the reaction between each 1-2mL portions. This water will react and destroy any remaining acetic anhydride. (Fig3.)
How did Shriver get crystals?
Shriver tried to induce crystals to form by adding some aspirin crystals from another lab group to the flask. He placed the flask on top of the ice in the 250 mL beaker. After a few minutes, more crystals formed than in the previous attempt, but there were still not enough crystals to collect in a funnel. Dr.
How does aspirin help with pain?
Sir John Vane discovered how aspirin works in the body while researching at the Royal College of Surgeons of England in 1971.8 According to the Journal of Chemical Education staff, aspirin relieves pain in the peripheral parts of the body by inhibiting the synthesis of prostaglandins. Healthy tissues have a certain normal concentration level of these hormones. When a tissue becomes damaged, it synthesizes more prostaglandins. A higher concentration of prostaglandins in the damaged tissue results in a sensation of pain. Aspirin inactivates enzymes that are essential in prostaglandin synthesis; therefore, it decreases pain by reducing the sensitivity of the damaged tissue to pain stimuli. The role of aspirin in reducing inflammation is not known with certainty. Prostaglandins synthesized by bacterial toxins in the hypothalamus increase body temperature. Aspirin is an antipyretic because it reduces the amount of prostaglandins that result from bacterial toxins in the hypothalamus.9
What was salicylic acid used for?
It was not until after the death of Hermann Kolbe that salicylic acid was used in the manufacturing process of aspirin.4.
What did Hoffmann find to be tolerable?
Hoffmann hypothesized that salicylic acid would be tolerable if it were more soluble in stomach acid. To achieve this more soluble form, Hoffmann replaced the hydrogen from the hydroxy group on the benzene ring of salicylic acid with an acetyl group. This resulted in acetylsalicylic acid.
What is willow bark used for?
This letter was inspired by the Doctrine of Signatures, a document stating that the environment of plants offers clues to the types of illnesses the plants might remedy. For example, willow trees grow in moist soil, and moist soil is associated with fever.2 In 1876, the Scottish physician Thomas MacLagan conducted an investigation of willow powder and its effectiveness in treating inflammation and fever. The results of his study indicate that willow powder will completely reduce both fever and joint inflammation. The substance in willow bark that is responsible for relieving pain and fever is salicin. The French pharmacist Henri Leroux crystallized a pure form of this yellow substance in 1829. Salicin was oxidized to form salicylic acid in early 1835 by the German chemist Lowig.3 Hermann Kolbe developed a more economical and efficient method to synthesize salicylic acid in 1873 from phenol and sodium hydroxide. After partnership with Friedrich von Heyden, Kolbe established a factory to produce large quantities of salicylic acid using this method. Kolbe also discovered that salicylic acid could be used as both a food preservative and an antiseptic. However, Joseph Lister had already popularized a more potent as well as less expensive antiseptic known as carbolic acid. Although salicylic acid was not the most widely used antiseptic of the time, it did become an important intermediate in the production of other pharmaceuticals, dye, and perfumes. It was not until after the death of Hermann Kolbe that salicylic acid was used in the manufacturing process of aspirin.4
When was salicin oxidized?
Salicin was oxidized to form salicylic acid in early 1835 by the German chemist Lowig.3 Hermann Kolbe developed a more economical and efficient method to synthesize salicylic acid in 1873 from phenol and sodium hydroxide.
What did Hoffmann's father have?
Hoffmann’s father suffered from rheumatoid arthritis, a condition often treated with salicylic acid. After several doses of salicylic acid, his father’s stomach became too irritated to continue the use of the medicine. Hoffmann hypothesized that salicylic acid would be tolerable if it were more soluble in stomach acid.
How long does it take for aspirin to excrete?
It takes about 48 hours to excrete an aspirin completely. The half-life of aspirin in the blood stream is 13-19 minutes and the half-life of its metabolite salicylate is around 3.5-4.5 hours. Aspirin’s inhibition of COX-1 results in reduced platelet aggregation for the 7-10-day average lifespan of platelets 1.
How do prostaglandins work?
Prostaglandins are found throughout the body and are made to help manage injury or infection. Prostaglandins upregulate the sensitivity of pain receptors. As a control mechanism, they act locally at the site of synthesis which limits the extent of their activity. They are also broken down rapidly by the body.
How is aspirin made?
Aspirin is prepared by chemical synthesis from salicylic acid, through acetylation with acetic anhydride. The molecular weight of aspirin is 180.16g/mol. It is odourless, colourless to white crystals or crystalline powder. Aspirin is an oral non-steroidal anti-inflammatory drug (NSAID) that is rapidly absorbed from the stomach and ...
Does aspirin increase platelet aggregation?
From a cardiovascular perspective aspirin also has an important role: Thromboxane A2 (TXA2) is a lipid that stimulates new platelet formation and increases platelet aggregation . Aspirin inhibits the production of thromboxane A2 (TXA2) by stopping the conversion of arachidonic acid to TXA2.
Which enzymes produce prostaglandins?
The enzymes that produce prostaglandins are cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2), they have diverse roles and are widely dispersed throughout body tissue. Cox-1 has a protective role for the stomach lining and COX-2 is involved in pain and inflammation. Aspirin binds to and acetylates serine (an amino acid used by ...
Does aspirin help with myocardial infarction?
In this way aspirin can help lower the risk of future myocardial infarction ( MI) or stroke 1,3. Aspirin, therefore, has an analgesic (reduces pain), anti-inflammatory (reduces redness and swelling), anti-platelet (reduces blood clots) and antipyretic (temperature reduction) effects 1,2,3. In cancer, aspirin is believed to impact a number ...
Does aspirin help with thrombus formation?
This aspirin effect is mediated via COX-1 inhibition within platelets and helps stop the platelets from sticking to each other or to plaques within the artery therefore reducing the risk of blood clot (thrombus) formation within the blood stream. In this way aspirin can help lower the risk of future myocardial infarction (MI) or stroke 1,3.
What is the chemical equation for aspirin?
The chemical equation for the synthesis of aspirin is C7H6O3 + C4H6O3 –> C9H8O4 +C2H4O2 , which is a reaction of salicylic acid with acetic anhydride in the presence of phosphoric acid. The byproduct is acetic acid.
What is a syringe used for?
It is used to treat pain, reduce fever, and to decrease the aggregation of platelets, such as to decrease blood clotting. ADVERTISEMENT.
Does cold water purify aspirin?
Adding cold water stops the reaction, and the products are filtered, yielding aspirin. Once aspirin is synthesized, it needs to be purified, and an estimation of its purity should be performed. Aspirin, or acetylsalicylic acid, is one of the oldest and most common medications worldwide.
What is the limiting reactant in a salicylic acid reaction?
In this experiment, the salicylic acid is the limiting reactant and the acetic anhydride is in excess. After the reaction heating period is over, the excess unreacted acetic anhydride will be destroyed by the addition of water to the mixture: water reacts with acetic anhydride to form 2 molecules of acetic acid, according to the reaction shown below.
What does purple aspirin mean?
to an aspirin sample and you see a purple color, it means that there is still some salicylic acid present and the sample is impure. The aspirin collected will then be purified by recrystallization. In this purification method, the crude aspirin will be dissolved in a small amount of warm ethanol. Water will then be added and the solution will be cooled slowly and then chilled. The acetylsalicylic acid will recrystallize, and the solid impurities (unreacted salicylic acid) should remain dissolved in the solution. The solid aspirin will again be collected using vacuum filtration and tested for purity. This aspirin should be more pure than the original aspirin. The final product will be dried and weighed and the theoretical and percent yields will be calculated.
What happens when you add water to an esterification reaction?
When the esterification reaction is complete, water will be added to the mixture. This will cause the precipitation of the acetylsalicylic acid and will react with any remaining acetic anhydride. The solid aspirin will be collected using vacuum filtration. Any other reaction ingredients that are soluble (this includes acetic acid, phosphoric acid, and water) will pass through the filter paper. The collected aspirin will be tested for its purity using FeCl
What is the best medicine for a fever?
Aspirin is an effective analgesic (pain reliever), antipyretic (fever reducer) and anti-inflammatory agent and is one of the most widely used non-prescription drugs. The use of aspirin had its origin in the 18th century, when it was found that an extract from the bark of willow trees was useful in reducing pain and fever. The active ingredient in willow bark was later found to be salicylic acid. The structure of salicylic acid is shown below. Although salicylic acid was effective at reducing pain and fever, it also had some unpleasant side effects. It is irritating to the lining of the mouth, esophagus, and stomach, and can cause hemorrhaging of the stomach lining. In 1899, the Bayer Company in Germany patented a drug they called aspirin , which was a modification of salicylic acid.
How to test for FeCl?
test, the samples do not have to be dry. To do the test, get 4 test tubes. Place 1 mL of ethanol and 2 drops of FeCl
Is aspirin a phenol?
Salicylic acid contains a phenol group , and phenols are known to be irritating. The Bayer Company replaced the phenol group with an ester group. This esterified compound (acetylsalicylic acid, also known as aspirin) was shown to be much less irritating than salicylic acid. Unfortunately, it is still irritating to the stomach and can cause hemorrhaging of the stomach walls. An aspirin tablet contains a small amount of aspirin (usually 300-400 mg) in a starch “binder” and sometimes contains other ingredients like caffeine and buffers. When aspirin is ingested, it is broken down to salicylic acid by the basic conditions in the small intestine. It is then absorbed into the bloodstream. Aspirin can be made by reacting salicylic acid with acetic acid in the presence of an acid catalyst. The phenol group on the salicylic acid forms an ester with the carboxyl group on the acetic acid. However, this reaction is slow and has a relatively low yield. If acetic anhydride is used instead of acetic acid, the reaction is much faster and has a higher yield (since acetic anhydride is much more reactive than acetic acid). The reaction is shown on the following page.
Introduction
Experimental Procedure
Discussion and Conclusion
Future Directions
Works Cited
- The main objective of the synthesis of aspirin lab was so produce aspirin (acetylsalicylic acid) through the reaction of salicylic acid and acetic anhydride. The methods used included recrystallization and scratching to produce a precipitate, which was then filtered to remove any excess moisture. The results displayed a percent yield of 34.3%, from...