Acetaminophen Synthesis Lab Report
Experiment 1
Synthesis of Acetaminophen
Clifford Tse
20529845
Partner – Raminder Dhanoa
TA – Xiao Qi
CHEM 123L - 012
February 6, 2014
Introduction
Acetaminophen, also commonly known as Tylenol, is an over-the-counter medicine used to relieve pain and reduce fevers. Within this experiment, Acetaminophen will be formed through the reaction between p-aminophenol and acetic anhydride. This reaction will incur Acetaminophen as a crude solid being impure, which will be purified further through the use of a recrystallization technique. The purification process involves dissolving a solid and recrystallizing as a crystal solid from the solution. The process is follow by heating the crude solid to dissolve using a minimal amount of solvent, …show more content…
often referred to as recrystallization solvent. It is then cooled to room-temperature and cooled even further in an ice-bath in order to have the crystals solidify within the saturated solution. Both impure and purified crude solids will be obtained through vacuum filtration, a technique used to separate the solvent and solid through vacuum pressure. (Stathopulos, 2014)
The purpose of this experiment is to determine the melting point of the crude solid, Acetaminophen, in both impure and purified solids. This is accomplished through the process of recrystallization. The crude solids will then be extracted through the use of vacuum filtration and further accessed in determining the melting point. The melting points are determined through using an apparatus known as MelTemp. The experimental melting point values determined are then used to be compared with theoretical listed ranges of pure Acetaminophen.
Experimental Procedure The experimental procedure used for this experiment was outlined in the CHEM 123L lab manual, Experiment #1. All steps were followed without deviation.
Experimental Observation
Mass of p-aminophenol
3.00g
Mass of 125mL Erlenmeyer Flask
54.50g
Mass of Crude Products with 125mL
57.64g
Mass of Crude Products
3.14g
Volume of Deionized Water Added
31.4mL
Mass of Purified Products with 125mL
57.01g
Mass of Purified Products
2.51g
Melting Point of Crude Product
160○C - 165○C
Melting Point of Purified Product
160○C - 163○C
Results and Calculations
C6H7NO (s) + C4H6O3 (aq) → C8H9NO2 (s) + C2H4O2 (aq)
Theoretical Yield
C6H7NO (s)
Mp-aminophenol = 109.13 g/mol m = 3.00 g n = m/M n = 0.0274 mol
C4H6O3 (aq) d = 1.08 g/mL
V = 4 mL
M = 102.09 g/mol m = d x V m = 4.32 g n = m/M n = 0.0423 mol
C6H7NO (s) is the limiting reactant
Mass of Acetaminophen m = M x n m = (151.16 g/mol) (0.0274 mol) m = 4.14 g
Percent Yield
= 75.8 %
Discussion Within this experiment, the experimental melting point of both the crude and purified products have been determined to be 160 ○C - 165 ○C and 160 ○C - 163 ○C respectively. When comparing with the theoretical data of Acetaminophen’s melting point to be within the range of 169 ○C - 170 ○C, the experimental values prove to be fairly close with less than 10% deviation in range values. When comparing the melting point of the experimental value and theoretical value, the purified product’s melting point is used as it has complete the recrystallization process sustaining a more similar characteristic to the theoretical sample with respect to its properties. When looking at the values, there appears to be no significant differences between the crude and purified product, thus shows no real benefit in solely comparing the purified product only because of possible experimental deviations. Although the experiment appears to have highly accurate results when comparing experiment and theoretical values, it would appear as though possible errors may have incurred along the process. Some issues that may have been raised include the instrumental accuracy of measuring proper proportions of acetic anhydride and p-aminophenol. The result of having lesser amounts of p-aminophenol would have led to a lower yield, and ultimately a lower yield percentage. Additionally, the melting point was determined through the use of the MelTemp apparatus, which utilizes a thermometer while looking through a small eye piece to observe physically. This process may have resulted in possible procedural errors as the process could have been difficult to evaluate due to the small eye piece and keeping track of temperature ranges. Throughout this experiment, the overall recrystallization process of Acetaminophen appears to have a yield percentage of 75.8%, lacking almost 25% from the expected theoretical value. The lack of yield may be the result of the above stated errors incurred. The experiment a whole, accurately follows through the conceptual theory of chemistry throughout the entire process.
Questions
1.
a.
In this experiment, each 10 mL of water was added for every 1 g of crude product produced. This is due to the solution retaining its saturated state, where 10mL per 1 g of crude is the correct ratio to sustain the solution. If 5 mL of water were to be added as the ratio instead, the solution would become supersaturated, resulting in having an effect to the recrystallization process.
b. If 15 mL of water was added for every 1 g of crude product, the solution would become unsaturated. There would be an excess amount of water within the ratio thus affects the purity of the product since more of the crude product would be required.
c. If the room temperature was used rather than a cold solvent in aiding the transfer of recrystallized products, the solubility of the crystals would be higher, thus incurring a possible loss in crystals during the vacuum filtration process. This in turn, would result in a loss of yield and ultimately affects the overall yield calculations.
d. The purpose of scratching the inner walls of the round bottom flask is to initiate the recrystallization process through the crystal growth stage.
2. Within the field of chemistry, the definition of an organic compound is a compound that contains carbon (Petrucci, et al.,
2011).
3. Amine:
Amides:
(Wikimedia, 2014)
4. The aspirin, a salicylate drug, is a commonly used drug used to relieve minor aches, pains and reducing fevers. It is also known as acetylsalicylic acid. Similar to Acetaminophen, both are produced through organic synthesis. Acetylsalicylic acid is synthesized from salicylic acid and acetic anhydride, producing acetic acid; C7H6O3 + C4H6O3 → C9H8O4 + C2H4O2 (About.com Chemistry, 2014) The salicylic acid is required to further continue the process of esterification to reduce irritation as a result of the phenol group pertained in salicylic acid. In doing so, this has produced a product similar to Acetaminophen, while sustaining better taste with less irritation. Aspirins are now commonly seen around the world and used as an everyday drug to benefit lives everywhere.
Conclusion The experiment performed has demonstrated the reaction between p-aminophenol and acetic anhydride, producing Acetaminophen and acetic acid. The reaction occurred results in a crude product identified as impure Acetaminophen. Purification of the product is performed through the process of recrystallization. Samples of both the crude and purified products are taken and used to determine the experimental melting point. These values are then used to compare with theoretical data and assess the accuracy and reliability of the experiment. With the crude and purified products of Acetaminophen having an experimental melting point of 160 ○C - 165 ○C and 160 ○C - 163 ○C respectively, the theoretically melting point being 169 ○C - 170 ○C deems a fairly accurate result, having less than 10% in deviation between values. Additionally, the yield of the products are determined through comparing experimental and theoretical yields of the reaction. With the crude product having a percentage yield of 75.8%, lacking almost 25% from theoretical calculations, deviations that may have influenced this result could be deemed through instrumental and procedural errors. These errors include the accuracy of the equipment, along with performing the experiment under the limitation of being a human.
References
Department of Chemistry 2014 Chemistry Laboratory Manual Fall 2014. University of
Waterloo, Waterloo. (pp. 12-15).
Petrucci, R. H., Herring, F. G., Madura, J. D., & Bissonnette, C. (2011). General chemistry: Principles and modern applications. (10 ed., pp. 248-252, 274). Toronto, Ontario: Pearsons Canada Inc.
Wikimedia. "Amine." Amine. http://en.wikipedia.org/wiki/Amine (accessed February 3, 2014).
Wikimedia. "Amide." Amide. http://en.wikipedia.org/wiki/Amide (accessed February 3, 2014).
About.com Chemistry. How to Make Aspirin - Acetylsalicylic Acid. http://chemistry.about.com/od/demonstrationsexperiments/ss/aspirin.htm. (accessed February 3, 2014).
Synthesis of Acetaminophen
Clifford Tse
20529845
Partner – Raminder Dhanoa
TA – Xiao Qi
CHEM 123L - 012
February 6, 2014
Introduction
Acetaminophen, also commonly known as Tylenol, is an over-the-counter medicine used to relieve pain and reduce fevers. Within this experiment, Acetaminophen will be formed through the reaction between p-aminophenol and acetic anhydride. This reaction will incur Acetaminophen as a crude solid being impure, which will be purified further through the use of a recrystallization technique. The purification process involves dissolving a solid and recrystallizing as a crystal solid from the solution. The process is follow by heating the crude solid to dissolve using a minimal amount of solvent, …show more content…
often referred to as recrystallization solvent. It is then cooled to room-temperature and cooled even further in an ice-bath in order to have the crystals solidify within the saturated solution. Both impure and purified crude solids will be obtained through vacuum filtration, a technique used to separate the solvent and solid through vacuum pressure. (Stathopulos, 2014)
The purpose of this experiment is to determine the melting point of the crude solid, Acetaminophen, in both impure and purified solids. This is accomplished through the process of recrystallization. The crude solids will then be extracted through the use of vacuum filtration and further accessed in determining the melting point. The melting points are determined through using an apparatus known as MelTemp. The experimental melting point values determined are then used to be compared with theoretical listed ranges of pure Acetaminophen.
Experimental Procedure The experimental procedure used for this experiment was outlined in the CHEM 123L lab manual, Experiment #1. All steps were followed without deviation.
Experimental Observation
Mass of p-aminophenol
3.00g
Mass of 125mL Erlenmeyer Flask
54.50g
Mass of Crude Products with 125mL
57.64g
Mass of Crude Products
3.14g
Volume of Deionized Water Added
31.4mL
Mass of Purified Products with 125mL
57.01g
Mass of Purified Products
2.51g
Melting Point of Crude Product
160○C - 165○C
Melting Point of Purified Product
160○C - 163○C
Results and Calculations
C6H7NO (s) + C4H6O3 (aq) → C8H9NO2 (s) + C2H4O2 (aq)
Theoretical Yield
C6H7NO (s)
Mp-aminophenol = 109.13 g/mol m = 3.00 g n = m/M n = 0.0274 mol
C4H6O3 (aq) d = 1.08 g/mL
V = 4 mL
M = 102.09 g/mol m = d x V m = 4.32 g n = m/M n = 0.0423 mol
C6H7NO (s) is the limiting reactant
Mass of Acetaminophen m = M x n m = (151.16 g/mol) (0.0274 mol) m = 4.14 g
Percent Yield
= 75.8 %
Discussion Within this experiment, the experimental melting point of both the crude and purified products have been determined to be 160 ○C - 165 ○C and 160 ○C - 163 ○C respectively. When comparing with the theoretical data of Acetaminophen’s melting point to be within the range of 169 ○C - 170 ○C, the experimental values prove to be fairly close with less than 10% deviation in range values. When comparing the melting point of the experimental value and theoretical value, the purified product’s melting point is used as it has complete the recrystallization process sustaining a more similar characteristic to the theoretical sample with respect to its properties. When looking at the values, there appears to be no significant differences between the crude and purified product, thus shows no real benefit in solely comparing the purified product only because of possible experimental deviations. Although the experiment appears to have highly accurate results when comparing experiment and theoretical values, it would appear as though possible errors may have incurred along the process. Some issues that may have been raised include the instrumental accuracy of measuring proper proportions of acetic anhydride and p-aminophenol. The result of having lesser amounts of p-aminophenol would have led to a lower yield, and ultimately a lower yield percentage. Additionally, the melting point was determined through the use of the MelTemp apparatus, which utilizes a thermometer while looking through a small eye piece to observe physically. This process may have resulted in possible procedural errors as the process could have been difficult to evaluate due to the small eye piece and keeping track of temperature ranges. Throughout this experiment, the overall recrystallization process of Acetaminophen appears to have a yield percentage of 75.8%, lacking almost 25% from the expected theoretical value. The lack of yield may be the result of the above stated errors incurred. The experiment a whole, accurately follows through the conceptual theory of chemistry throughout the entire process.
Questions
1.
a.
In this experiment, each 10 mL of water was added for every 1 g of crude product produced. This is due to the solution retaining its saturated state, where 10mL per 1 g of crude is the correct ratio to sustain the solution. If 5 mL of water were to be added as the ratio instead, the solution would become supersaturated, resulting in having an effect to the recrystallization process.
b. If 15 mL of water was added for every 1 g of crude product, the solution would become unsaturated. There would be an excess amount of water within the ratio thus affects the purity of the product since more of the crude product would be required.
c. If the room temperature was used rather than a cold solvent in aiding the transfer of recrystallized products, the solubility of the crystals would be higher, thus incurring a possible loss in crystals during the vacuum filtration process. This in turn, would result in a loss of yield and ultimately affects the overall yield calculations.
d. The purpose of scratching the inner walls of the round bottom flask is to initiate the recrystallization process through the crystal growth stage.
2. Within the field of chemistry, the definition of an organic compound is a compound that contains carbon (Petrucci, et al.,
2011).
3. Amine:
Amides:
(Wikimedia, 2014)
4. The aspirin, a salicylate drug, is a commonly used drug used to relieve minor aches, pains and reducing fevers. It is also known as acetylsalicylic acid. Similar to Acetaminophen, both are produced through organic synthesis. Acetylsalicylic acid is synthesized from salicylic acid and acetic anhydride, producing acetic acid; C7H6O3 + C4H6O3 → C9H8O4 + C2H4O2 (About.com Chemistry, 2014) The salicylic acid is required to further continue the process of esterification to reduce irritation as a result of the phenol group pertained in salicylic acid. In doing so, this has produced a product similar to Acetaminophen, while sustaining better taste with less irritation. Aspirins are now commonly seen around the world and used as an everyday drug to benefit lives everywhere.
Conclusion The experiment performed has demonstrated the reaction between p-aminophenol and acetic anhydride, producing Acetaminophen and acetic acid. The reaction occurred results in a crude product identified as impure Acetaminophen. Purification of the product is performed through the process of recrystallization. Samples of both the crude and purified products are taken and used to determine the experimental melting point. These values are then used to compare with theoretical data and assess the accuracy and reliability of the experiment. With the crude and purified products of Acetaminophen having an experimental melting point of 160 ○C - 165 ○C and 160 ○C - 163 ○C respectively, the theoretically melting point being 169 ○C - 170 ○C deems a fairly accurate result, having less than 10% in deviation between values. Additionally, the yield of the products are determined through comparing experimental and theoretical yields of the reaction. With the crude product having a percentage yield of 75.8%, lacking almost 25% from theoretical calculations, deviations that may have influenced this result could be deemed through instrumental and procedural errors. These errors include the accuracy of the equipment, along with performing the experiment under the limitation of being a human.
References
Department of Chemistry 2014 Chemistry Laboratory Manual Fall 2014. University of
Waterloo, Waterloo. (pp. 12-15).
Petrucci, R. H., Herring, F. G., Madura, J. D., & Bissonnette, C. (2011). General chemistry: Principles and modern applications. (10 ed., pp. 248-252, 274). Toronto, Ontario: Pearsons Canada Inc.
Wikimedia. "Amine." Amine. http://en.wikipedia.org/wiki/Amine (accessed February 3, 2014).
Wikimedia. "Amide." Amide. http://en.wikipedia.org/wiki/Amide (accessed February 3, 2014).
About.com Chemistry. How to Make Aspirin - Acetylsalicylic Acid. http://chemistry.about.com/od/demonstrationsexperiments/ss/aspirin.htm. (accessed February 3, 2014).