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Chemical lab experiment
Chemical lab experiment
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Organic Chemistry Laboratory – CH 200 (2014-2015) Experiment 9
Synthesis of Aspirin through Esterification and Crystallization
Justin Gaña, Jamilette Guiam, Angelica Jimenez, and Joanna Jusay*
Department of Biological Sciences, College of Science
University of Santo Tomas, España Street, Manila 1051
Date Submitted: November 7, 2014
Abstract The synthesis of aspirin was remodeled and revised for a small scale experiment. An esterification reaction from the combination of salicylic acid and acetic anhydride with the presence of an acid catalyst produced acetylsalicylic acid (aspirin) and acetate. Purification of the crude aspirin was done through a technique called crystallization, wherein both the single solvent and mixed solvent
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4.00 mL of acetic anhydride was then added to the salicylic acid inside the Erlenmeyer flask. 5 drops of concentrated sulfuric acid (H2SO4) was added to the cloudy solution. Concentrated sulfuric acid acted as a catalytic agent which sped up the reaction. Prior to weighing and preparing the solution, a water bath was placed on top of a hot plate and allowed to heat up until only 80 °C. An increase in temperature would cause the solution to polymerize into a different substance. Once the desired temperature of the water bath was achieved, the Erlenmeyer flask containing the solution was floated in it and swirled until the salicylic acid dissolved and the solution became clear. Ten minutes was the maximum allotted amount of time for the reaction. After the dissolution of the salicylic acid and acetic anhydride, 20 mL of distilled ice water was added to the solution and was subjected to an ice bath. The water would destroy any unreacted acetic anhydride and will cause the insoluble aspirin to precipitate (Bettleheim, 2001). The flask was swirled to initiate and speed up the crystallization of acetylsalicylic acid and to allow the oily layer to disperse. Once the oily layer disappeared, Buchner funnel was prepared. The funnel was placed on top of an Erlenmeyer flask subjected to vacuum suction. The purpose of the vacuum suction was to dry the crystals as much …show more content…
The hydroxyl group on the benzene ring reacts with the acetic anhydride to form an ester functional group. This reaction is called an esterification reaction (Pavia, Lampman, Kriz, & Engel, 1999). A similar reaction was executed using isoamyl alcohol and acetic anhydride. The addition of sulfuric acid catalyzes the reaction. When the reaction is complete, there will be some unreacted salicylic acid and acetic anhydride that will be left with the crude aspirin. A technique used to purify the aspirin is called crystallization. It is so called because it involves dissolving a solid that has originally crystallized from a reaction or mixture, and then causing it to again crystallize from another solution. The typical setup for this is that the crude solid is dissolved in a hot suitable recrystallization solvent. The solution allowed to cool down and crystallization to happen (Lehman,
Every 5 minutes, a small amount of mixture was dissolved in acetone (0.5 mL) and was spotted onto a thin layer chromatography (TLC) plate, which contained an eluent mixture of ethyl acetate (2 mL) and hexanes (8 mL). The bezaldehyde disappearance was monitored under an ultraviolet (UV) light. Water (10 mL) was added after the reaction was complete, and vacuum filtrated with a Buchner funnel. Cold ethanol (5 mL) was added drop-by-drop to the dried solid and stirred at room temperature for about 10 minutes. Then, the solution was removed from the stirrer and place in an ice bath until recrystallization. The recrystallized product was dried under vacuum filtration and the 0.057 g (0.22 mmol, 43%) product was analyzed via FTIR and 1H NMR
The experimental Fischer esterification of 8.92g of acetic acid with 5.0g of isopentyl alcohol using concentrated sulfuric acid as a catalyst yielded 4.83g (65.3% yield) of isopentyl acetate. The product being isopentyl acetate was confirmed when the boiling point during distillation had similar characteristics to that of the literature boiling points2. Physical characteristics like color and smell also concluded a match of our product with what was intended. 1H-NMR spectroscopy analysis supported this claim due to the fact that the integration values and chemical shifts were comparable to isopentyl acetate. Lastly, infrared spectroscopy (IR) showed similar key characteristics of our product’s wavelengths to that of pure isopentyl acetate5.
The most classic and standard procedure for producing esters is the Fisher-esterification reaction. Discovered in 1895 by German chemists Emil Fischer and Arthur Speier 4, this reaction involves refluxing a carboxylic acid and an alcohol in the presence of an acid catalyst. In order to drive the equilibrium towards the products, the water from the dehydration process must be removed and there must be an excess amount of alcohol. A vast range of carboxylic acids may be used for this reaction however the type of alcohols are limited. Primary and secondary alcohols are most frequently used in esterification reactions, tertiary alcohols are steric ally hindered usually resulting in poor yields5 and tend to undergo elimination reactions instead. In this rea...
Firstly, an amount of 40.90 g of NaCl was weighed using electronic balance (Adventurer™, Ohaus) and later was placed in a 500 ml beaker. Then, 6.05 g of Tris base, followed by 10.00 g of CTAB and 3.70 g of EDTA were added into the beaker. After that, 400 ml of sterilized distilled water, sdH2O was poured into the beaker to dissolve the substances. Then, the solution was stirred using the magnetic stirrer until the solution become crystal clear for about 3 hours on a hotplate stirrer (Lab Tech® LMS-1003). After the solution become clear, it was cool down to room temperature. Later, the solution was poured into 500 ml sterilized bottle. The bottle then was fully wrapped with aluminium foil to avoid from light. Next, 1 mL of 2-mercaptoethanol-β-mercapto was added into fully covered bottle. Lastly, the volume of the solution in the bottle was added with sdH2O until it reaches 500 ml. The bottle was labelled accordingly and was stored on chemical working bench.
Then, I added 8 drops of concentrated phosphoric acid to the mixture. swirling it a few times. Then, I carefully took the flask to the station as I avoided trying to breath the vapors of the acetic anhydride. I put the e-flask into the beaker of water sitting on the hot plate in order to heat it for seven minutes. Once the seven minutes was up, my partner carried the e-flask to the fume hood, and added 3 mL of de-ionized water to the flask. She swirled it for a couple of minutes there. She brought it back tot he station where I gradually added 60 Ml of de-ionozed water to the mixture while my partner stirred the mixture constantly. I was able to see some of the aspirin beginning to form. In order to complete the crystallization process we cooled the flask in an ice-water bath from 4:00 until 4:20. As we waited I began to set up our filtration system. I used a ring stand, right angel clamp, three finger clamp, Buchner funner, filtering flask,rubber tubing, and filter paper in the Buchner funnel. I turned on the aspirator and pored some water over the filtering paper in order to create a good
Esterification was used to synthesize aspirin which was by reacting salicylic acid with acetic anhydride. To speed up the reaction, dehydrating agent and conc. sulphuric acid was present. The purity of a substance, which is the aspirin in this particular experiment, can be determined by the identification of its melting point.
Aspirin contains the substance acetylsalicylic acid (ASA), which can relieve inflammation, fever, pain, and known as a “blood thinner”. Aspirin was not officially trademarked until March 6, 1899 when the Imperial Office of Berlin made it official. It has been used for the last 110 years, but its natural form, salicylic acid has been around for thousands by Egyptians, Greeks, and Romans. Aspirin is available in over 80 countries and known as the best non-prescription drug. The most common use of aspirin is to cure headaches and use it as a pain reliever, but aspirin is known to prevent heart attack and strokes. It was first proposed in 1940, but wasn’t confirmed until 1970 when doctors would recommend taking aspirin daily [1].
Ensure gloves are worn at all times when handling strong acids and bases within the experiment of the preparation of benzocaine. 4-aminobenzoic acid (3.0g, 0.022 moles) was suspended into a dry round-bottomed flask (100cm3) followed by methylated sprits (20 cm3). Taking extra care the concentrated sulphuric acid of (3.0 cm3, 0.031 moles) was added. Immediately after the condenser was fitted on, and the components in the flask were swirled gently to mix components. It should be ensured that the reactants of the concentrated sulphuric acid and the 4-aminobenzoic acid were not clustered in the ground glass joint between the condenser itself and the flask. In order to heat the mixture to a boiling point, a heating mantle was used and then further left for gently refluxing for a constituent time of forty minutes. After the duration of the consistent forty minutes the rou...
The purpose of this experiment was to learn and preform an acid-base extraction technique to separate organic compounds successfully and obtaining amounts of each component in the mixture. In this experiment, the separation will be done by separatory funnel preforming on two liquids that are immiscible from two layers when added together. The individual components of Phensuprin (Acetylsalicylic acid, Acetanilide, and Sucrose as a filler) was separated based upon their solubility and reactivity, and the amount of each component in the mixture was obtained. Also, the purity of each component will be determined by the melting point of the component.
The conical vial was placed in a small beaker and allowed to cool to room temperature. The mixture was Cooled thoroughly in an ice bath for 15-20 minutes and crystals collected by vacuum filtration on a Hirsch funnel. The vial was rinsed with about 5 mL of ice water and transferred into to the Hirsch funnel and again washed with two additional 5mL portions of ice water. Crystals were dried for 5-10 minutes by allowing air to be drawn through them while they remained on the Hirsch funnel. The product was transferred to a watch glass plate and allow the crystals to dry in air. Crude acetaminophen product was weighed and set aside a small sample for a melting point determination and a color comparison after the next step. Calculation of the percentage yield of crude acetaminophen (MW = 151.2). was done and recorded in the lab notebook.
The solvent should be easily removed from the purified product, not react with the target substances, and should only dissolve the target substance near it’s boiling point, but none at freezing. A successful recrystallization uses minimum amount of solvent, and cools the solution slowly, if done to fast, many impurities will be left in the crystals. Using the correct solvent, in this case ice water and ethyl acetate, the impurities in the compound can be dissolved to obtain just the pure compound. A mixed solvent was used to control the solubility of the product. The product is soluble in ethanol an insoluble in water. Adding water reduced solubility and saturates the solution and then the crystals
Background Information Aspirin is an analgesic (pain relieving) and an antipyretic drug (a drug that lowers body temperature). The main constituent of aspirin is 2 - ethanoythydroxybenzoic acid, also known as acetylsalicyclic acid (shown below right). It was originally made from just salicylic acid (which is found in the bark of a willow tree) when used by the Ancient Greeks to counter fever and pain, but its bitterness and tendency to irritate the stomach caused problems. These were resolved by the German chemist Felix Hoffman, who made the acetyl derivative of salicylic acid in the
·Aspirin (salicylic acid acetate) is an anti-inflammatory (decreases swelling and inflammation), anti-pyretic (fever reducing), and anti-platelet (decreases platelets in the body to thin blood). Many heart treatment patients take an aspirin a day to prevent blood clotting. However, if aspirin is taken in large quantities over long periods of time, it may cause gastric ulcers or other internal damage. The molecular formula of aspirin is C9H8O4. Some examples of Aspirin are Bayer, Ecotrin, and Aspergum.
Drug is a chemical which alters the processes in the organism, which is used in the medicine for prevention, diagnosis and treatment of the diseases (Farlex, 2011). Drug discovery is a long term process that needs money investment. The process of drug investigation takes approximately from 9 to 15 years during which the number of chemicals that can become drug is reduced from 10,000 to 1-2 (Saparov, 2011). Even after manufacturing the drug is studied by scientists for modifying its structure, delivery and effects on the organism. Drug discovery consists of several stages which help to examine its effectiveness and side effects.
A mixture of 2 mL aniline, 15 mL deionized water and 3 mL acetic anhydride were stirred. After thirty minutes the reaction was complete and the product was completely precipitated out of the solution. Vacuum filtration was used to isolate the crude acetanilide using a 125 mL filter flask and porcelain Büchner funnel. The product was then washed with 2 mL of ice water and left to dry for about twenty minutes. The observed melting point for the crude acetanilide was 114.3 °C - 115.7 °C. The second procedure dealt with finding a suitable solvent to recrystallize the crude acetanilide. A sand bath was set up and 0.5 mL of each solvent was added to 50 mg of acetanilide in four different test tubes. The four solvents used to test the solubility of the acetanilide were water, ethanol, dichloromethane and hexanes. If the solid dissolved in the solvent at room temperature then it was too soluble and that solvent could be eliminated. The acetanilide completely dissolved in ethanol and dichloromethane, therefore eliminating them from being the suitable solvent. If the solid did not dissolve in room temperature then it was placed in the sand bath and left to boil. If the solid dissolved, it was placed in the ice bath and if crystals were observed coming out of the solution then the suitable solvent was found. The suitable solvent was water as the crystals came out once placed in the ice bath. The