Analysis Of Eugenol: The Fragrant Component Of Cloves

Good Essays
Isolation and Identification of Eugenol: The Fragrant Component of Cloves
*Adri, Kiersten Jayne R., Aguinaldo, Samuel Jr.
Group 2
Department of Chemistry, College of Science
University of Santo Tomas, España, Manila 1008

Abstract. In this experiment, the primary objective was to isolate eugenol from cloves. An amount of 30 grams of dried cloves and 300 mL of water was distilled over a flame for over 2 hours. The distillate underwent extraction with dichloromethane, water and sodium hydroxide. Concentrated hydrochloric acid was added to the aqueous extract to lower it to pH 9; it was again extracted with 2 x 30 mL of DCM. These organic extracts were dried over anhydrous magnesium sulfate, filtered into a pre-weighed flask and had their
…show more content…
Since eugenol is not soluble in water, the concentration of the eugenol in the vapor over the boiling eugenol–water suspension does not depend on concentration of the eugenol. The relative amounts of eugenol and water in the vapor simply depend on the vapor pressures of the pure materials. The vapor pressure of water at 100 °C is 760 torr, and the vapor pressure of eugenol at 100 °C is approximately 4 torr; therefore, the vapor is roughly 0.5 % eugenol. The suspension boiled when its vapor pressure was equal to the external pressure. Since both the eugenol and the water contributed to the vapor pressure of the suspension, the suspension boiled before either pure substance would normally boil. Since many essential oils contain liquids that may not survive heating at higher temperatures, steam distillation is an especially advantageous technique for isolating them because their immiscible mixture with water boils below 100 …show more content…
After obtaining the oil of cloves by steam distillation, the eugenol was isolated by extraction. In this process the fact that eugenol, because it is a phenolic compound, is weakly acidic whereas both eugenol acetate and caryophllene are neutral was considered. Thus, when the clove oil was treated with a sodium hydroxide (a strong base) it resulted in the selective formation of the sodium salt of eugenol which was soluble in the aqueous phase. The other neutral compounds did not react with sodium hydroxide and therefore remained in the organic phase. After the separation of the aqueous phase, its extraction with DCM and its acidification, the organic extract was dried over anhydrous magnesium sulfate. The eugenol was finally isolated by evaporation of the organic solvent in the rotary

You May Also Find These Documents Helpful

  • Good Essays

    Eugenol Research Paper

    • 133 Words
    • 1 Page

    At high sustained temperatures, natural aromatic compounds can easily be decomposed after being evaporated. Thus, eugenol can be easily decomposed at atmospheric boiling point. In order to prevent this from occurring, the boiling point of the compound should be lowered. In steam distillation process, the boiling point are lowered by the addition of water in an partially vacuumed container, through Raoult’s Law. Eugenol and water has different vapor pressure. Water has a vapor pressure of 760 mmHg while Eugenol has a vapor pressure of 4 mmHg. Thus, the total vapor pressure in the closed system is 764 mmHg, resulting in lower boiling point. Using the Clausius-Clapeyron equation(ln (P1 / P2) = (ΔH / R) (1/T2 - 1/T1)), the boiling point of the…

    • 133 Words
    • 1 Page
    Good Essays
  • Good Essays

    There is a slight difference between the two molecules (see figure 1) is the placement of the alkene functional group is pointed (see figure 1). Both eugenol and isoeugenol possess the same physical properties. These molecules are a clear to yellow oily liquid with a consistency of higher viscosity than water. The chemical properties are very similar between the two. Both have the same molar mass and chemical formula. The only difference is eugenol has a slightly higher melting point and lower boiling point than isoeugenol by a couple of degrees Celsius; this is most likely because of some impurities in isoeugenol. Eugenol and isoeugenol only absorb strongly in the UV region of the spectrum is due to the arene functional group (lab 4 guidance).…

    • 161 Words
    • 1 Page
    Good Essays
  • Powerful Essays

    The purpose of this experiment was to use various methods of analysis to determine the identity of an unknown volatile liquid. In the first part of the experiment, the molecular mass was found by using water to find the volume of a flask through calculations and this as well as the mass of the gas of the unknown liquid were put into the a manipulated version of the ideal gas equation to determine the molar mass of the liquid, which was 14.21g per mole. The next part was used to determine the density of the volatile liquid. First the volatile liquid was placed in a pyncometer and massed; water was then placed in the same (now clean and empty) pyncometer and massed. The density equation was manipulated using the data for water to solve for the mL of the capillary tube. This new information was used to find the density of the liquid, which was 1.33g/mL. The last part of the experiment was used to determine the boiling point of the volatile liquid. A test tube was placed inverted in a flask filled with the unknown liquid that was in a water bath heating. When bubbles from the test tube slowed and began to go back into the test tube, the temperature was taken and this served as a measurement of the boiling point. The average measured boiling point was 60.2°C. The measured data was inadequate to identify the liquid with. The unknown liquid was revealed to be methanol; the revealed identity could then be used to compare the data to the actual information for methanol. The molar mass was found to have a percent error of 55.6%, the density had a percent error of 68.1% and the boiling point had one of 6.95%. The measured data for the boiling point was fairly accurate, but the molar mass and the density both had very large percent error. The reasons for this will be discussed more in the discussion.…

    • 2705 Words
    • 11 Pages
    Powerful Essays
  • Better Essays

    A reflux apparatus was assembled with a water-cooled condenser and a drying tube. Isopentyl alcohol, glacial acid sulfuric acid is added to a 25 milliliter round bottom flask and attached to the reflux apparatus. The mixture was boiled, the extracted first using water followed by aqueous sodium bicarbonate. The mixture was dried using anhydrous granular sodium sulfate. After dried, the sample was placed in a distillation apparatus and heated. This resulted in 1.8g of pure isopentyl acetate, a 44% yield.…

    • 1095 Words
    • 5 Pages
    Better Essays
  • Good Essays

    Since simple distillation is a physical process, it separated the two chemicals from the mixture based on how easily they vaporize. As the mixture was heated, the temperature rose until it reached the temperature of the lowest boiling substance in the mixture which was cyclohexane. The temperature at which the first drop was collected was 79.5oC and the distillation of cyclohexane was stopped when the still-head temperature was 94.5oC . Therefore, the boiling range of cyclohexane in this experiment was 79.5oC- 94.5oC.The resultant hot vapor passed through into the condenser and was converted into liquid, which was then collected into a graduated cylinder. During this time, the ethyl benzene remained in its original phase. Since cyclohexane had a lower boiling point, it is considered to be more volatile in comparison to ethyl benzene. After a plateau in temperature was observed, the temperature was increased in order for ethyl benzene to reach its boiling point. The temperature at which ethyl benzene was collected was 127oC and the distillation of ethyl benzene was stopped when the still-head temperature was 138.5oC. The boiling range for ethyl benzene was observed to be in between 127oC-138.5oC. The liquids were collected in increments of 4mL. The first 28mL collected were of cyclohexane and the last 16 mL collected were of ethyl benzene,…

    • 1803 Words
    • 8 Pages
    Good Essays
  • Good Essays

    • An ether soluble fraction of the whole plant yielded 4,7-dimethoxy-5-(2-propenyl)-1, 3-benzodioxole or apiol, in a liquid state, 2,4,5,-trimethoxy styrene, mp 138°, and three phytosterols, campesterol, stigmasterol and β-sitosterol.…

    • 626 Words
    • 3 Pages
    Good Essays
  • Good Essays

    Phytochemical analysis of plants has been supported enormously by the development of rapid and accurate methods of screening plants for particular chemicals. The phytochemical methods are widely used to screen and analyse bioactive phytochemicals, not only for the quality control of crude drugs, but also for the elucidation of their therapeutic mechanisms. There is a growing interest in correlating phytochemical constituents of a plant with its pharmacological…

    • 1117 Words
    • 5 Pages
    Good Essays
  • Good Essays

    Steam Distillation

    • 494 Words
    • 2 Pages

    In this experiment, the process of steam distillation was used to purify a natural product, (the essential oil of spearmint). This phenomenon works because when two immiscible liquids are distilled, the boiling point of the mixture is below the boiling point of the both pure compounds. Since water has a significantly lower boiling point than spearmint, a much greater proportion of water molecules was vaporizing at any time during the distillation. Even though the components of spearmint oil have low vapor pressure, they are volatile enough to vaporize to some extent and a small amount will lifted off with the water molecules. This boiling will occur when the independent internal vapor pressures are equal to 760 torr, which is the external vapor pressure. It is noted that steam distillation, unlike regular distillation, it does not follow Raoult's Law.…

    • 494 Words
    • 2 Pages
    Good Essays
  • Satisfactory Essays

    Fractional distillation

    • 923 Words
    • 4 Pages

    Fractional distillation separates a mixture of liquids based on differences in the boiling points of the liquid. The purpose of this experiment was to identify, separate and characterize liquids from a mixture. This experiment took two days to complete. On the first day, we examined the properties of the solution and prepared a heating curve. A certain amount of the liquid mixture was poured into a small flask fitted with a two-hole stopper. In the first hole there was a thermometer and in the second hole there was a rubber tube which was attached to a piece of glass. The flask was placed on top of a wire stand and it was clamped to a peg-board. A burner was placed under the wire stand. A cold water bath was placed close by with a test tube into it. The rubber tubing from the flask with the mixture was inserted into the test tube in the water bath. The mixture was slowly heated and the temperature was recorded every ten seconds. The mixture stopped heating before the test tube was dry. On the second day, we used the heating curve to help perform a fractional distillation to separate the liquids. The same apparatus as day one was set up with a fresh sample of the liquid mixture. Three test tubes were labeled as fraction I,II and III. The mixture was fractionally distilled and the collecting tubes was switched at the appropriate temperature. The volume, flammability, odour, density and boiling point of each fractions were recorded. After this experiment, we concluded that the liquids in the mixture were 2-propanol and water.…

    • 923 Words
    • 4 Pages
    Satisfactory Essays
  • Good Essays

    Extraction

    • 507 Words
    • 3 Pages

    Purpose: In this experiment we aim to demonstrate that we can separate two volatile compounds from a mixture due to the different chemical properties of each compound. We will accomplish this by a separation procedure known as distillation, which relies on each compound having a distinct and separate boiling point. Our pure products will be analyzed with gas chromatography to determine the success of the distillation.…

    • 507 Words
    • 3 Pages
    Good Essays
  • Powerful Essays

    Three solvents were used for the preparation of the extracts - distilled water, acetone, ethanol at four different concentrations. Plant powder was weighed and mixed with the three solvents to attain four different concentrations viz., 20%, 40% 60% and 80% respectively. These extracts were further used for the…

    • 1322 Words
    • 6 Pages
    Powerful Essays
  • Powerful Essays

    Anyone who has walked through a forest or who enjoys the variety of fragrances that flowers have to offer knows that many plants and trees have their own distinctively pleasant odors. These odors are due to the volatile essential oils, many of which have been prized commodities since ancient times. If a list of commercially important essential oils was compiled the list would exceed 200 essential oils. Thyme, garlic, peppermint, and spearmint are but a few examples of the many essential oils used in commercial goods. Essential oils have many applications in the world that can range from flavor enhancement to perfumes. Some oils have also been found to have medicinal properties such as antibacterial and antifungal abilities. Chaulmoogra oil is one of the few know curative agents for leprosy. The oils can also be used in the paint industry, where turpentine is used as a solvent for many paint products.…

    • 2108 Words
    • 9 Pages
    Powerful Essays
  • Good Essays

    In this study, the presence of menthol and camphor were determined from 5 different locally produced medicinal topical ointment samples. Sample of Vick® VapoRub® and Hurix’s Massage Balm were purchased from local pharmacies, Bunga Cengkih Balm and Serai Balm samples were purchased from the grocery shop. Buah Pala Balm sample was purchased from the night market. Sample of Serai and Buah Pala both do not have the meditag of hologram which indicates that they are not certified by the MOH.…

    • 896 Words
    • 4 Pages
    Good Essays
  • Powerful Essays

    antioxidant property

    • 4241 Words
    • 18 Pages

    6. Leal, P.F. Braga, M.E.M. Sato, D.N. Carvalho, J.E. Marques, M.O.M. Meireles, M.A.A. (2003). Functional properties of spice extracts obtained via supercritical fluid extraction. J. Agric. Food Chem., 51, 2520–2525.…

    • 4241 Words
    • 18 Pages
    Powerful Essays
  • Powerful Essays

    Journal of Medicinal Plants Research Vol. 5(10), pp. 2035-2040, 18 May, 2011 Available online at http://www.academicjournals.org/JMPR ISSN 1996-0875 ©2011 Academic Journals…

    • 2889 Words
    • 12 Pages
    Powerful Essays