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Green Isolation of Limonene
Essential oils are organic compounds that are extracted from natural sources and used in many products such as flavorings, fragrances, and cleaning products. The optically active enantiomer, D-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.
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. Large-scale CO2 processing has had commercial success in many separation and extraction processes. The tunable solubility properties, low toxicity, and ease of removal of CO2 have led to well established CO2 technology for the extraction of various food products, including essential oils and hops, and for the decaffeination of coffee and tea.
Another major benefit of using carbon dioxide 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 3, CO2 sublimes at atmospheric pressure of 1.01 bar. The triple point of CO2, where solid, liquid, and gas phases coexist in equilibrium, is achieved at 5.2 bar and -56.6 oC. At or near this point, dry ice melts, forming liquid carbon dioxide. If the temperature and pressure are increased to the critical point (73.8 bar and 31.0 oC), the CO2 exists as a supercritical fluid and has no distinct liquid or vapor phase but properties that are similar to both.
Figure 1: The temperature-pressure diagram for CO2 shows phase transformations, triple point, and critical point.
Siena Green Chemistry Summer Institute Lucas Tucker, V1 Page 1
Image | Green Isolation of Limonene
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