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Analysis of aspirin
Synthesis of aspirin discussion
Synthesis of aspirin discussion
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Discussion 19 The purpose of this experiment was to synthesize and purify of Aspirin and Oil in wintergreen. While determining the purity through analytical techniques. During the first part of the lab the crude sample of acetylsalicylic acid, Aspirin, was synthesized. The synthesis of Aspirin shows a general trend of chemical reactions known as esterification reactions. The compound containing a hydroxyl group reacts with a compound containing a carboxylic acid group, producing an ester molecule and water. Since this reaction is slow, the lab used acetic anhydride instead of acetic acid to drive the reaction to completion. As a result, the chemical formula is C7H6O3(s) + C4H6O3(l) → C4H8O4(s) + C2H4O2(l) The mass of aspirin produced was 6.051g producing a high percent yield …show more content…
Since salicylic acid is insoluble in water, a method called recrystallization was used, by mixing with ethanol. Ethanol is non-polar which makes it a great solvent for salicylic acid. The solution was cooled so that the Aspirin was no longer soluble and it left the impure salicylic acid in the solution and the solid left was pure aspirin. The mass of the pure aspirin produced was 0.609g which gave a low percent yield of 20.32%. The low % yield was probably due to unsuccessful recrystallization. Recrystallization shows a very reasonable way to eliminate unwanted impurities. Part 4 of this lab showed a way to observe impurities by comparing the melting point of crude and pure samples. Since impurities are to be shown in the crude sample it would have a lower melting point and larger range. The known melting point of aspirin is to be 135 oC. The crude sample had a melting point range from 69oC to 81 oC. While the Pure sample melting point range was from 116oC to 125oC. Since the Pure sample was still below 135 oC, this shows that there are still some impurities
As a final point, the unknown secondary alcohol α-methyl-2-naphthalenemethanol had the R-configuration since it reacted the fastest with S-HBTM and much slower with R-HBTM. TLC was a qualitative method and ImageJ served as a quantitative method for determining which reaction was the faster esterification. Finally, 1H NMR assisted in identifying the unknown from a finite list of possible alcohols by labeling the hydrogens to the corresponding peaks.
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.
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
Mixed melting point was used to confirm the identity of the product. The smaller the range, the more pure the substance. When the two substances are mixed; the melting point should be the same melting range as the as the melting range obtained after filtering. If the mixed melting point is lower one taken from the crystals, then the two substances are different.
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.
Esters are defined as molecules consisting of a carbonyl group which is adjacent to an ether linkage. They are polar molecules which are less polar than alcohols but more so than ethers, due to their degree of hydrogen bonding ability. Most often derived from reacting an alcohol with a carboxylic acid, esters are a unique, ubiquitous class of compounds with many useful applications in both natural and industrial processes 1. For example, within mammals, esters are used in triglycerides and other lipids as they are the main functional group attacking fatty acids to the glycerol chain 2. A unique property of esters is their tendency to give off distinct aromas such as the scent of apples (Ethyl caprylate) and bananas (Isoamyl acetate). This is of a unique importance especially in industries that utilize flavors and aromas such as the tobacco, candy and alcohol industry. Consistent research is conducted in order to enhance and increase the effectiveness of esters in these products 3.
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].
The purpose of this experiment was to study the reactions of amino acids and aspartame. Several solutions were prepared and used in TLC analysis. A permanganate test and a ceric nitrate test were also performed. The summary of the results is shown below.
The purpose of conducting this experiment was to synthesise and characterise for the preparation of benzocaine via a fishcer esterification reaction by the means of amino benzoic acid alongside ethanol. The product was also precipitated from a solution in order to gain a pH of 8.The secondary aim was to esterify the reaction in an equilibrium reaction catalysed via the addition of acid shown below:
The discovery of captopril as a potent inhibitor of ACE led to the recent development of many series of novel structures with similar biological activity [9]. To date a wide variety of ACE inhibitors from various land and marine food sources have been reported such as milk [10], cheese [11], egg white [12], canola [13], peanut [14], rapeseed [15], antler [16], fish muscle [17], seaweeds [18] and tuna [2].
Aspartame or known by its chemical formula of C14H18N2O5, is a very common chemical food additive usually added in artificial sweeteners for coffee and other products like Splenda and Equal. It is also mixed with other food products like candy, gum, vitamins and supplements. Its molar mass is 294 grams per mol or it has 294 as its molecular mass. Its chemical structure forms a dipeptide-methyl ester (Walters, 2001). Aspartame is known as a synthetic chemical combination which is built approximately on phenylalanine, aspartic acid and methanol (Wells, 2011). It is a solid and can dissolve with water (Walters (2)). It is chemically manufactured by using tritylation and chlorination ("Chemical Process Steps," n.d.). But when its manufacturing process is discussed, its patent reveals that it uses by-products of genetically-modified cells and later treated with chemicals and methanol to produce aspartame (Butler, 2013).
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.
Dr. Ketchum knew before starting the study that contamination would be a concern. Throughout the study, steps were taken to ensure that there was no contamination and that the samples were of high quality. The results themselves prove there was no contamination. This is demonstrated by the high Q30 scores and the lack heteroplasmic bases when the samples were screened for
Analysis of Aspirin Tablets Aim --- To discover the percentage of acetylsalicylic acid in a sample of aspirin tablets. ----------------------------------------------------------------- In order to do this, the amount of moles that react with the sodium hydroxide must be known. This is achieved by using the method of back titration.
These were all naturally occurring substances. No refinement had occurred, and isolation of specific compounds (drugs) had not taken place.