25. The synthesis of acetaminophen can be achieved in two ways. As with all drug

Question

25. The synthesis of acetaminophen can be achieved in two ways. As with all drug discovery, smal amounts of a drug are first made to determine the most efficient method of synthesis. As the bench chemist, you are in charge of determining the best method to make acetaminophen. After 5 years of working on this project, you run two final reactions to reach your determination. In the first reaction you react 1.36 g of p-aminophenol (CsH-ON) with 1.750 g of acetic anhydride (CaHeO,). The products of this reaction are acetaminophen (CaHoON) and acetic acid. In the second reaction, you react 1.47 g of p-aminophenol (CGH,ON) with 1.830 g of acetyl chloride (C2H,OCI). The products of this reaction are acetaminophen (CeHO2N) and hydrochloric acid. The first reaction yields 1.28 g of acetaminophen in 2.5 hours and the second reaction yields 1.66 g of acetaminophen in 3.75 hours Which reaction would you select to use for mass production of acetaminophen? Justify your choice The costs of p-aminophenol, acetyl chloride, and acetic anhydride are $86.50/kg, $43.20 per 50g, and $128.00 per 3 kg, respectively. Considering this information, would you change the reaction that you selected in part a? Why or why not? Be as specific as possible Once the production is moved to a production plant, the reaction can be scaled up 1000 times. One tablet of Tylenol Regular Strength contains 325 mg of acetaminophen. A production run lasts 7 days before the plant must close and be thoroughly cleaned. Each production run is required to make at least 185,000 dosages. In considering this information, along with all other information provided above, which reaction would you select for making acetaminophen? Justify your choice; consider all factors. What other factors do you think might influence what reaction would you select for making acetaminophen? Justify your choice. a. b. c. d.

Explanation / Answer

a) For bulk production, normaly we will go for the yield. but other factores also influence. but the answer for this first question is the second reaction. because yield of first reaction is 68% and for second reaction is 82%. so based on yield, second reaction is prefered.

b) When we consider the cost of the reactents, we will go for the first reaction. because p-aminophenol is commen for both the reactions. but acetic anhydride is very cheap. it is only $ 42.66 per Kg. but for acetyl chloride is $ 864 per Kg. so cost is very important for the bulk production.

c) here if we go for the second reaction we will get more dosages. but for bulk production we have to consider the cost and timeas well.

d) Based on the informatiom, my openion is, we have to select first reaction. because cost is low compared to the second step. acetyl chloride is almost 20 times costlier than acetic anhydride. and time also low (1.25 h) when we compare with second reaction. this will impact in the bulk production. the utillity cost can also reduce by this reduced time. in the first reaction the side product is acetic acid. it is a mild organic acid. but in the second reaction the side product is HCl. HCl is stron minaral acid and have corrosive nature. so first reaction is preffered.

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