CHEM 31.

1 JK-1L

Exercise 3 Extraction of an Essential Oil from Pomelo (Citrus maxima) peel

ABSTRACT Extraction of essential oil from Pomelo peel was done through distillation and extraction set-ups. Distillation enabled the acquiring of Pomelo peel extract and extraction enabled the purification and separation of the essential oil from water. The obtained product was 0.97 g which is 0.37% out of all the obtained Pomelo peel. The identity of the essential oil present that was Limonene was confirmed through finding out the boiling point of the product through determining it in a number of trials. The determined boiling point was 150.5C whereas the theoretical boiling point is 176C. It may be quite far due to some errors in experimentation.

INTRODUCTION Distillation is a method of separating mixtures based on differences in their boiling points. It is a unit operation, or a physical separation process, and not a chemical reaction. In simple distillation, all the hot vapors produced are immediately channeled into a condenser that cools and condenses the vapors. Therefore, the distillate will not be pure - its composition will be identical to the composition of the vapors at the given temperature and pressure, and can be computed from Raoult's law. As a result, simple distillation is usually used only to separate liquids whose boiling points differ greatly (rule of thumb is 25 C), or to separate liquids from involatile solids or oils. For these cases, the vapor pressures of the components are usually sufficiently different that Raoult's law may be neglected due to the insignificant contribution of the less volatile component. In this case, the distillate may be sufficiently pure for its intended purpose.Like vacuum distillation, steam distillation is a method for distilling compounds which are heat-sensitive. This process involves bubbling steam through a heated mixture of the raw material. By Raoult's law, some of the target compound will vaporize (in accordance with its partial pressure). The vapor mixture is cooled and condensed, usually yielding a layer of oil and a layer of water.Steam distillation of various aromatic herbs and flowers can result in two products; an essential oil as well as a watery herbal distillate. The essential oils are often used in perfumery and aromatherapy while the watery distillates have many applications in aromatherapy, food processing and skin care (en.wikipedia.org). The boiling point is the temperature at which the vapor pressure of the liquid phase of a compound equals the external pressure acting on the surface of the liquid. The external pressure is usually the atmospheric pressure. For instance, consider a liquid heated in an open flask. The vapor pressure of the liquid will increase as the temperature of the liquid increases, and when the vapor pressure equals the atmospheric pressure, the liquid will boil. Different compounds boil at

different temperatures because each has a different, characteristic vapor pressure: compounds with higher vapor pressures will boil at lower temperatures. Boiling points are usually measured by recording the boiling point (or range) on a thermometer while performing a distillation. This method is used whenever there is enough of the compound to perform a distillation. The distillation method of boiling point determination measures the temperature of the vapors above the liquid. Since these vapors are in equilibrium with the boiling liquid, they are the same temperature as the boiling liquid. The vapor temperature rather than the pot temperature is measured because if you put a thermometer actually in the boiling liquid mixture, the temperature reading would likely be higher than that of the vapors. This is because the liquid can be superheated or contaminated with other substances, and therefore its temperature is not an accurate measurement of the boiling temperature. If you are using the boiling point to identify a solid compound which you have isolated in the lab, you will need to compare its boiling point with that of the true compound (orgchem.colorado.edu). Liquid-liquid extractions using a separatory funnel are essentially the only kind of extraction performed in the organic teaching labs. The "liquid-liquid" phrase means that two liquids are mixed in the extraction procedure. The liquids must be immiscible: this means that they will form two layers when mixed together, like oil and vinegar do in dressing. Some compounds are more soluble in the organic layer and some compounds are more soluble in the aqueous layer (orgchem.colorado.edu). In extracting essential oils from Pomelo (Citrus maxima), d-Limonene is obtained. dLimonene is the major component of the oil extracted from citrus rind. When citrus fruits are juiced, the oil is pressed out of the rind. This oil is separated from the juice, and distilled to recover certain flavor and fragrance compounds. The bulk of the oil is left behind and collected. This is food grade d-Limonene. After the juicing process, the peels are conveyed to a steam extractor. This extracts more of the oil from the peel. The moment that the steam is condensed, a layer of oil floats on the surface of the condensed water (www.floridachemical.com). Pure limonene is a clear liquid. Limonene is a monoterpene, made up of two isoprene units. Limonene occurs in two optically active forms, l-limonene and d-limonene. Both isomers have different odors: l-limonene smells piney and turpentine like and d-limonene has a pleasing orange scent. Limonene is found in the essential oils of citrus fruits and many other plant species. Industrial limonene is produced by alkali extraction of citrus residues and steam distillation. This distillate contains more than 90% d-limonene (www.phytochemicals.info).

OBJECTIVES This experiment mainly desire to extract the essential oils present in Pummelo (Citrus maxima) and to find out what essential oil does it contain. The specific objectives of this study are as follows: To be able to know the role or purpose of distillation and extraction To be able to identify and describe the process and set-up of distillation and extraction. To identify the essential oil in Pomelo (Citrus maxima) peel. METHODS The materials and procedure for this experiment is adapted from our chemistry lab manual entitled Chemistry 31.1 Organic Chemistry Laboratory. The procedure is found on pages 58-60.

PRESENTATION OF RESULTS Table 1 shows the weight of the obtained peel and essential oil extracted from the peel. The weight of Pomelo peel obtained was 261.98 g. The peel underwent distillation through the distillation set-up that was made. After distillation, the product obtained was 0.97 g. On the other hand, the computed percentage discovery was only 0.37%. Table 1. Data for obtained peel and essential oil Material Weight(g) Pomelo Peel 261.98 g Vial/Beaker 23.61 g Product 0.97 g Percent Recovery 0.37% In Table 2, the boiling point data of the essential oil after extraction was acquired. The determination of its boiling point was done for two trials in each trial made. The overall trials done were four trials to ensure accuracy.

Table 2. Boiling Point of d-Limonene from Pomelo peal Temperature of Condensing Liquid Trial 1 Trial 2 150C 150C T1 150C 152C T2

DISCUSSION OF RESULTS The results are shown in Table 1 and 2. The obtained values were clearly presented. After the distillation and extraction process for the acquiring of the essential oils of Pomelo, the obtained product which is the essential oil present in the peel was just 0.97 g. When computed the percentage recovery of the essential oil or d-limonene is from the Pomelo peel is just 0.37%. In the confirmation of the identity of the organic compound as the essential oil of Pomelo, the boiling point of the organic compound was acquired. This enables us to confirm the identity of the compound. This also tests the validity of the experiment and how near is their values from the theoretical value. Several trials were made in getting the boiling point of the obtained substance. Two setups were done and two trials were made in each set-up in order to confirm its accuracy. The average result in the boiling point of the substance was 150.5C. CONCLUSION In the experiment, the result has yield low percentage recovery. This experiment is effective since the desired extraction, purification/distillation, and identification of the essential oil found in Pomelo (Citrus maxima), was successfully done. The low percentage recovery may be caused by some technical and personal errors that were brought up in the experiment. The average boiling point of d-limonene that was obtained was 150.5C. The theoretical boiling point of this essential oil ranges around 176C. It is quite far but also quite near to the theoretical boiling point. Hence, it can still be confirmed that the identity of the essential oil is dlimonene.

QUESTION AND ANSWERS Pre-Laboratory Questions 1. Draw and label a diagram of a simple and a steam distillation set-up.

2. What is the purpose of extraction? Extraction is done in order to separate any unwanted substances from your desired product. It is also essential to separate all needed amounts and maximize the percentage recovery.

3. What properties are considered when choosing a good solvent for extraction? In choosing good solvent for extraction, you must consider its polarity in relevance to the polarity of your essential oil. The polarity of the solute and solvent must be the same. The organic compound must be highly miscible to the chosen solvent. It must not also be reactive with your organic compound to avoid alteration of the structure of the compounds. 4. Do you expect the hexane layer to lie above or below the aqueous layer? How would you prove its position? The position of the hexane layer should be above the aqueous layer. Hexane is less dense than water. It is also immiscible in water. Therefore the hexane layer should be above the aqueous layer. 5. Using the Handbook of Chemistry and Physics, look for the boiling point of the following substances and draw their structures: hexane, n-hexyl chloride and n-hexanol. Explain the difference of their boiling point. The boiling point of hexane is 69 C, n-hexyl chloride is 134 C, and n-hexanol is 155-159 C. As noticed, the structures of the three compounds are almost the same. The

differences in their boiling point is caused by the side chains of n-hexyl chloride and nhexanol in their structures. These side chains cause the boiling point to be higher.

Post-Laboratory Questions: 1. Why is distillation of two liquids carried out slow rather than fast? You'll get cleaner separation and a purer product with slow distillation. With rapid distillation, the flow of gaseous material into the condenser is faster, and it will tend to entrain and carry over other materials which will end up in the condensed liquid. The idea with slow distillation is to carefully regulate the process so that each "fraction" comes over in as pure a form as possible. 2. A 300 mL aqueous solution containing 30 g of compound A was to be extracted with ether. The solubility of compound A in ether at room temperature is 20.0 g per 100-mL and in water is 13.3 g per 100 mL. Calculate the weight of the compound that would be recovered by extraction with (a) two 150-mL portions of ether and (b) one 300mL portion of ether.

3. Compare the experimental boiling point of limonene with the literature value. Point out possible explanation for its difference, if any. The literature value of limonene is 176C and the obtained value is 150.5 C. The difference is quite near but also quite far. These errors might be caused by technical and personal errors that were done in the performing of the experiment.

REFERENCES Boiling poingt. Accessed on July 6, http://orgchem.colorado.edu/hndbksupport/dist/dist.html Distillation. Accessed on July 6, 2011. Accessed from http://en.wikipedia.org/wiki/Distillation d-limonene.Accessed on July 6, 2011. Accessed on July 6, 2011. Accessed from http://www.floridachemical.com/whatisd-limonene.htm d-Limonene. Accessed on July 6, 2011. Accessed from http://www.phytochemicals.info/phytochemicals/limonene.php Extraction.Accessed on July, 2011. http://orgchem.colorado.edu/hndbksupport/ext/ext.html Accessed from 2011. Accessed from