extraction

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Jan 9, 2024

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Extraction of Chemical Compounds to Individual Constituents Experiment 2: Extraction

I. Purpose The purpose of the lab is to isolate p-toluic acid, p-tert Butylphenol, and acetanilide through recrystallization. As well as using different temperatures and pressures to isolate terpenes from orange and lemon peels using liquid CO2. Thereafter using organic compounds to obtain both chromatography and spectroscopy to identify the terpenes. II. Experiment Refer to Appendix D below III. Discussion Part I For the first portion of the lab, the original mass of the orange peel was 2.719 grams and the mass after the liquid CO2 extraction was 2.255. Thus, the essential oil recovery was about 82.93%. The important IR properties of the orange and lemon are at 1644.07 and 1644.04 𝑐𝑚 −1 respectively which exhibit an aromatic C=C bond. Thereafter, one can observe the peak for limonene for orange and lemon respectively at 2964.44 𝑐𝑚 −1 and 2964.90 𝑐𝑚 −1 with 𝑠𝑝 2 hybridization due to the alkene bond exhibited on the IR spectrum. One may also observe an alkane for orange and lemon respectively at 2913.04 and 2910.30 𝑐𝑚 −1 . The only confounding variable observed in both of the IR’s is the presence of an O -H bond of the orange and lemon respectively at 3350.93 and 3351.62 𝑐𝑚 −1

After obtaining the IR, the next portion referrences the GC data. The orange oil showed the area percent for α - pinene, β -myrcene, limonene, and terpinene respectively as 10.124% (∫520.180), 85.86% (∫4411.760), 3.70% (∫ 1.280 𝑒 5 ), and .3159% (∫16.230). For the lemon oil the area percent for the terpenes is as follows respectively 33.796% (∫1223.997), 50.58% (∫1682.150), 12.03% (∫7.326 𝑒 5 ), .591% (∫19.654 ). When examining the GC data, I compared the GC1 standards to the data obtained in class as a-pinene has the lowest melting point so the retention time will be the first to appear, thereafter myrcene, limonene, and terpinene with the highest melting point. Part II Through isolating each compound within the mixture, the percent recovery for crude p- Toluic, p - Toluic acid , p-tert butylphenol, and acetanilide is as follows 18.66%, 10.4%, 33.88%, and 58.96 percent. In terms of the relative melting points, the experimental data was 150-152 ℃ , 155- 165 ℃ , 90-130 ℃ and 30-35 ℃ . When examining the standard melting point for p-Toluic acid, the range is between 178-182 ℃ which indicates that there were impurities within the solution, or a common case is that the apparatus to measure the specimen was already set higher than the observed melting point. On the other hand, the butylphenol melting point does not deviate as much from the observed as the actual is between 96-101 ℃ within the scientific literature. For acetanilide, the melting point greatly deviates from the actual literature of 114.3 ℃ . This value could be due to several compounding variables. Either I forget to write 130-135 ℃ in my experimental portion since the thermometer doesn’t manufacture the 100 alongside the ten’s place. Thus, a human error in terms of reading the thermometer, or the temperature tells me that the acetanilide that gave us percent recovery of 58.96 is extremely impure and is most likely a

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combination of other compounds. With this in mind, the compounds most likely to be true to that of the original mixture would be the butylphenol. IV. Conclusion Overall, the experiment was relatively successful as the data was able to examine the properties of terpenes through IR and GC. As well as the second portion of the lab to separate the mixture for recrystallization by introducing a series of techniques that will be continue to be used for multiple labs such as the rotoVap, filtration, sandbath etc. The application of terpenes is especially prevalent within the medicinal use of cannabis; thus, the orange and lemons gave us a more practical and legal application of the terpene structure.. To reduce compounding variables in the future, one methodology would be to prevent any of the peel from getting to the bottom of the tube as well as to make sure there is no mixing of the aqueous and organic phase when the solution is being filtered into the flask. Overall, the goal was to extract each of the mixtures into their constituent components.

Calculation of Percent Recovery Example: P-toluic Percent Recovery: 18.66% = .125 g of isolated p-toluic/.67 (2/3 of the 1:1:1 mixture) Appendix B

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Appendix D Part A Oil Peel Mass (g) Oil Extracted (g) Essential Oil Content (%) Orange 2.719 .24 8% Lemon 2.9 .95 32.76 Orange Oil Limonene B-myrcene a-pinene y-terpinene Retention time 3.784 2.866 2.602 3.978 Integration (area) 1.280e^5 4411.760 520.180 16.230 Area percent 3.70% 85.86% 10.124% .3159% Lemon Oil Limonene B-myrcene a-pinene y-terpinene Retention time 3.644 2.836 2.562 3.900 Integration (area) 7.326e^4 1682.150 1223.997 19.653 Area percent 12.03% 50.58% 39.796% .591% Part B Starting Mass of 1:1:1 Mixture, Amount Used (g): 2.5 Name % Recovery Mass after recrystallization (g) Melting Range (C) Crude p-toluic acid 18.66 .125 150-152

P-toluic acid 10.4 .013 155-165 p-tert-butylphenol 33.88 .227 90-130 acetanilide 58.96 .395 30-35 Revised Experimental Data for Part B Accredited to Nina Carnavelle References Friestad, G.K. Techniques and Experiments in Organic Chemistry: Biological Perspectives and Sustainability W.W. Norton, 2023

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