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OBJECTIVE BACKGROUND Lab #7: GREEN CHEMISTRY CO2 extraction--Isolation of Limonene from Orange Rind To extract the essential oil limonene from orange rind using a green chemistry method. Essential oils are organic compounds that are extracted from natural sources and used in many products such as flavorings, fragrances, and cleaning products. Limonene is the major component of orange oil, which is found in the outer, colored portion of the rinds of oranges and other citrus fruits. The structure of limonene is shown below. Traditionally essential oils have been extracted through the use of steam distillation or organic solvent extraction. During the past two decades, great strides have been made in technology that uses supercritical or liquid carbon dioxide in place of organic solvents. CO2 is useful as a ‘green’ alternative solvent because it provides environmental and safety advantages; it is nonflammable, relatively nontoxic, readily available, and environmentally benign. Although CO2 is a greenhouse gas, when used as a solvent it is captured from the atmosphere, not generated, resulting in no net environmental harm. Another major benefit of using CO2 as a solvent is its accessible phase changes. Unlike other gases, relatively low temperatures and pressures can be used to form liquid and supercritical CO2. As shown on the phase diagram in Figure 1, CO2 sublimes (goes directly from solid to gas) at normal atmospheric pressure of ~1atm. The triple point of CO2, where solid, liquid, and gas phases coexist in equilibrium, is achieved at 5.1atm and -56.6°C. At or near this point, dry ice melts, forming liquid carbon dioxide. If the temperature and pressure are increased to the critical point (72.8atm and 31.0°C), the CO2 exists as a supercritical fluid and has no distinct liquid or vapor phase, but properties that are similar to both. Dry ice sublimes at atmospheric pressure and temperatures above -78°C. If the CO2 is sealed in a vessel during sublimation, the internal pressure in the vessel increases. After the temperature and pressure have increased sufficiently, liquid CO2 forms. In this experiment, you will use liquid CO2 to extract the essential oil limonene from orange rind. You may also choose to extract and isolate the essential oil from something other than orange rind. You may, for instance, choose to extract eugenol from cloves or cinnamaldehyde from cinnamon. You may also try lemon peel instead of orange etc. If you do want to be adventurous you may extract the essential oil of any natural product as long as you supply it (spices and fruit peelings work well).PDF Image | GREEN CHEMISTRY CO2 extraction Limonene Orange Rind
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