Isolation of a Natural Product by Steam Distillation: Cinnamaldehyde from Cinnamon Cinnamaldehyde
Nojan Nasseri Niaki
Thursdays 6:30pm – 9:20pm
Organic Chemistry Laboratory
(CHE.231.L.1)
Instructor: Dr. Kafle
Lab Report – Experiment II
ABSTRACT: The main purpose of this lab is to extract the organic compound cinnamaldehyde from cinnamon. The process used in order to execute the extraction of the cinnamaldehyde is called steam distillation. After massing the Cinnamaldehyde on a scale in the laboratory, its total mass came out to 0.050 grams. The calculated percent yield came out to around 1.55%. The experiment yielded success due to the fact that my data fell in the range (of the expected percent yield.)
PROCEDURES: The procedure for this lab experiment is located in Professor Zachary J. Poulos’ manual A Laboratory Manual for the Health Science Major: Organic Chemistry I. Refer to pages 36-42 for a detailed procedure regarding this experiment. Refer to the second page in the back of the laboratory manual (lab notebook) for a short and concise written version of this procedure.
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After steam distillation occurred, the solvent was exposed to the open air for seven days. The Cinnamaldehyde built up in the bottom of the test tube, baring the color brown. The calculated actual percent yield of my experiment was 1.55%. This calculation fell in the range of the literature percent yield of Cinnamaldehyde which is between 1.00-3.00%. Due to my calculation falling in range to what is was supposed to be (literature percent yield), I would have to conclude that my experiment in this lab was successful. However, there are many ways that this experiment could have gone wrong but didn’t. If I had not extracted enough crystals, or spilled some out of my container, my calculation would not have fell in the range of the literature percent
C. Pour about one quarter of the first unknown packet into the first cup and add
With a 9-inch pipet was used to add water through the condenser to keep the flask no more than half way full. Clove oil was extracted from the distillate in 1 mL increments every 5 to 10 minutes. The distillation and extraction process was approximately 37 minutes with 7 mL of distillate recovered. The product recovered was a light yellow liquid color with the same strong, sweet, cinnamon odor as the raw clove. 1 mL of dichloromethane solution was used to rinse the Hickman still and was then transferred to the centrifuge tube. Another 2 mL more of dichloromethane was added and shaken vigorously. Upon shaking the the mixture turned a cloudy white color with two layers resulting. The major component of clove oil was extracted with two more 3 mL portions of dichloromethane solution. The mixture was allowed to cool and left in the hood overnight to dry.
Everything went according to plan in this lab. The steam distillation actually went well overall and we had a successful system. Through the analysis of the IR spectrum, it can be seen that the unknown constituent of the major constituent contained a O-H-N-H stretch, Phenol ring and C7H16. Reading peaks was a little iffy, because some peaks were hard to read or interpret. Through using figure 10.1 on page 110, I came to the conclusion that the structure of the major constituent is:
Working in the hood or a designated work area, add about 1 mL of ethyl alcohol to a clean evaporating dish. Place the evaporating dish on a heat- resistant pad.
1.) Briefly explain the concept of steam distillation. What is the difference between a simple distillation and a steam distillation? When a mixture of two immiscible liquids are distilled it is referred to as codistillation. This process is referred to as steam distillation when one of the liquids is water. This distillation is used to separate organic liquids from natural products and reaction mixtures in which the final product results in high boiling residues such as tars, inorganic salts, and other relatively involatile components. It is useful in isolating volatile oils from various parts of plants and not useful in the final purification of a
In the separating funnel, a heterogeneous mixture was formed: resulting in an organic layer (top) and a solvent layer (bottom). This effectively allowed the draining of the solvent, in order to isolate the organic layer, the impure ester (1-pentyl ethanoate)
Distillation is a method of separating two volatile chemicals on the basis of their differing boiling points. During this lab, students were given 30 mL of an unknown solution containing two colorless chemicals. Because the chemicals may have had a relatively close boiling point, we had to employ a fractional distillation over a simple distillation. By adding a fractionating column between the boiling flask and the condenser, we were able to separate the liquids more efficiently due to the fact that more volatile liquids tend to push towards the top of the fractionating column, thereby leaving the liquid with the lower boiling point towards the bottom. After obtaining the distillates, we utilized a gas chromatograph in order to analyze the volatile substances in the gas phase and determine their composition percentage of the initial solution. Overall, through this lab we were able to enhance our knowledge on the practical utilization of chemical theories, and thus also demonstrated technical fluency involving the equipment.
1 ml of water should be added to the first test tube and make a note. In the second test tube, 1 ml of methyl alcohol should be added. In the third test tube, 1 ml of hexane must be added. Lastly, the fourth test tube will be a control.
An ester was synthesized during an organic reaction and identified by IR spectroscopy and boiling point. Acetic acid was added to 4-methyl-2-pentanol, which was catalyzed by sulfuric acid. This produced the desired ester and water. After the ester was isolated a percent yield of 55.1% was calculated from the 0.872 g of ester recovered. This quantitative error was most likely due to product getting stuck in the apparatus. The boiling point of the ester was 143° C, only one degree off from the theoretical boiling point of the ester 1,3-dimethylbutyl, 144 ° C. The values of the
It is not uncommon to have a percent yield less than 100% as was observed in our experiment. Imperfect percent yield can be interpreted that the condition were not optimal and could be improved. Despite careful measurements some component will still be lost during transferring between containers. One way to get a better percent yield is by minimizing transfers. A low percent yield could be a result of evaporation
In this experiment, solutions of 2-naphthol will be prepared in buffer solutions with pH values near the expected pKa (refer to Table 7.1 in the lab Manual) at 25 °C and the UV-visble spectra of each solution will be measured using a Cary 50 spectrometer. For detailed procedure, refer to the lab manual (J. F. Wójcik and T. S. Ahmadi, Experimental Physical Chemistry, 2015; p.3-5.). A modification of the procedure is, time drift of the pH was not calculated. The pH of the pH = 4.00 buffer was not measured every 45 minutes to 1 hour.
The filter paper, holding the aspirin crystals, was removed from the funnel and was left to dry before being weighed. Once the aspirin crystals were weighed, the theoretical yield and the percent yield of the experiment were calculated. The procedure was repeated once more using the same steps.
Part 2 to determine the empirical formula and percentage yield of the compound synthesized in Part 1. Spectrophotometry is a routine laboratory test that has the added advantage
A good yield of isopentyl acetate was obtained during this experiment. Loss of the product was likely through transferring liquid from separatory funnel to the Erlenmeyer flask and residual material left in the distillation flask. Using an organic solvent like benzene or cyclohexane as a transfer agent would improve the yield, since their boiling points were around 80 oC and could be easily separated from the final product through simple distillation. However this
Cinnamaldehyde, cinnamic aldehyde or 3-phenyl-2-propenal is the major constituent of cinnamon oil, extracted from several species of Cinnamomum (C. verum, C. burmanii, C. cassia), under the family Lauraceae, a group of evergreen trees. Cinnamon bark (particularly C. verum) yields 0.4-0.8% oil, which contains 60-80% cinnamaldehyde, 4-5% sesquiterpenoids (α-humulene, β-caryophyllene, limonene and others), eugenol, cinnamyl acetate, eugenol acetate, cinnamyl alcohol, methyl eugenol, benzaldehyde, benzyl benzoate, cuminaldehyde, monoterpenes (linalool, pinene,