Steam Distillation And Isolation of Eugenol Report Ramsey Padilla Jane Erwin 03/29/2012 Introduction: Steam distillation is completed

by the distillation of water and another liquid (1). Steam distillation allows mixtures of organic substances to distill and form a compound known as a distillate. Oil is often a water immiscible liquid that is separated by distillation. Clove oil consists predominately of an organic liquid called eugenol. Eugenol has a high boiling point and can be steam distillated from ground clove. Ground cloves are composed of about 16% oil (2). The clove oil consists of 58.2% of eugenol (3). Extraction is an experimental technique used in the separation of the oil and eugenol. The main objective of the experiment is to isolate eugenol from the oil obtained from the distillate produced by the steam distillation (4). Eugenol is the main product produced from the reagents in part one of the experiment.

Reactions for Clove Oil extraction: Eugenol Conjugate Base of Eugenol

+
Conjugate Base of Eugenol Eugenol

Table of Reagents: Reagents Quantity Ground Cloves 50.080g CH2Cl2 100 mL 5% KOH 75 mL 10% HCl As Needed Anhydrous sodium sulfate As Needed Water 150 mL

Procedure: Steam Distillation: Place approximately 50g of ground cloves and 150 mL of water in a 500 mL boiling flask. Collect distillate until the distillate is clear. Put into an Erlenmeyer flask and cover the top with aluminum foil with some wholes for next week. Separation of clove oil from distillate: Transfer half of distillate, about 75 mL, to a seperatory funnel and add 25 mL of CH2Cl2 to the funnel. Collect CH2Cl2 and aqueous layers in separate flasks. Repeat steps with other half of distillate. Isolation of Conjugate Base of Eugenol: Add combined layers of CH2Cl2 layers to funnel. Add 25 mL of 5% KOH. Separate aqueous layer and put CH2Cl2 layer back into funnel repeat steps with KOH two more times. Collect aqueous layers in a labeled Erlenmeyer flask. Isolation of Eugenol: Add 10% HCl to aqueous layer until the aqueous layer becomes acidic. In addition, add 25 mL of CH2Cl2 and separate two layers into separate flasks. Add 25 mL of CH2Cl2 to the aquesous layer one more time and collect the combined CH2Cl2 layers in a labeled flask. Dry combined layers of CH2Cl2 layers with anhydrous sodium sulfate. Filter and cover flask with foil with holes and store for next week. Results: Recovered Eugenol: 1.81g Oil in ground cloves: 16% Eugenol in oil: 58.2% 50.080g Clove 16g Oil 100g Cloves 58.2g Eugenol 100g Oil 4.663g Eugenol

Theoretical yield of Eugenol: 4.663g Actual yield of Eugenol: 1.81g Recovery yield: 1.81g/4.663g=38.82% Spectrum analysis Eugenol: Frequency (cm-1) Assignment 3517.5 O-H stretch 3078.5, 3011.2 C-H stretch 2975.6, 2936 C-H stretch 1510.76 C=C arene stretch 1265.02, 1231.23 C-O stretch Discussion: The theoretical yield based on the experimental conditions is 4.663g. The actual yield of eugenol obtained was 1.81g. This was due to the fact that the steam distillation did not reach completion. The distillate was not clear when the steam distillation was stopped. Thus, not all of the oil from the ground cloves was obtained causing for the recovery yield to be 38.82%. The IR spectrum for Eugenol was very similar to the actual Eugenol spectrum (5). The major peaks such as the O-H stretch, multiple C-H stretches, ad C=C stretch were present in both of

the spectrum. The O-H stretch on the actual spectrum had a much sharper and bigger peak than the experimental one obtained. Based on the results, the experimental eugenol obtained from the ground cloves appears to have not been contaminated by any other substances since the peaks are pretty much the same everywhere else on each of the spectrums. The recovered yield was really low since only about 13.84% of eugenol can be recovered theoretically from ground cloves. Thus, about 6.93g of eugenol is the amount that can be recovered from 50.080g of ground cloves. The recovered yield of eugenol was 26.12%. The reason that most of the eugenol was not recovered could have been due to the fact that some could have been evaporated over the two week break. Some of the material could have not been isolated from the other substances obtained from the ground cloves. There does not seem to be any contamination of other substances in the recovered product since the IR spectrum had no identifiable abnormalities when compared to the actual IR spectrum of eugenol. Conclusion: The main objective of the steam distillation was to recover as much of the clove oil from the ground cloves used as possible. This was successful since approximately 150 mL was obtained from the steam distillation. In addition, the main purpose for part two of the experiment was to isolate eugenol. Eugenol was effectively isolated from the oil obtained from the steam distillation. The recovery yield was fair due to the fact that the steam distillation did not go to completion. The goal of the experiment was accomplished and an IR spectrum was obtained of the product to identify any contamination that the compound might have. The compound has no contamination present since it was a good match with the literal IR of eugenol from source number 5. The experiments performed were both successful with favorable results. References: 1. Isolation and Distillation PowerPoints (Vista) 2. http://faculty.bennington.edu/~bullock/Chem1/clove.pdf 3. http://www.marinwater.org/documents/Chap6_CloveOil_8_28_08.pdf (page 6-6) 4. Eugenol PowerPoint (Vista) 5. http://www.chem2.bham.ac.uk/schools/eugenolir.htm (literal IR spectrum for Eugenol) 6. IR spectrum Handout (identify IR peaks) 7. ChemSketch

Synthesis of Eugenol Benzoate Report Ramsey Padilla Jane Erwin 03/29/2012 Introduction: Eugenol can react with benzoyl chloride to produce a solid named eugenol benzoate. The synthesis of eugenol benzoate is an indirect method used to characterize eugenol. The purpose of the experiment is to obtain a solid derivative known as eugenol benzoate to find the melting point and analyze the solid forms IR spectrum as well. The literature melting point for the solid derivative is 70C (1). The main product of the reaction between eugenol and benzoyl chloride is eugenol benzoate. This experiment is a very small-scaled one in terms of the amounts of reagents used. The eugenol benzoate obtained should effectively characterize the eugenol isolated. Reaction: Eugenol Benzoyl Chloride Eugenol Benzoate

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Table of Reagents Reagents 5% KOH Quantity As Needed Water 1 mL Benzoyl Chloride 5 drops

KOH H2O

+ KOH
Methanol & Ether 1 mL & 2mL

Anhydrous Sodium Sulfate As Needed

Reagent Eugenol Benzoyl Chloride

Formula C10H12O2 C7H5OCl

Melting Pt -7.5 C -1C

Density 1.06 g/cm^3 1.21 g/cm^3

Quantity Used 0.203g 5 drops

Molar Mass 164.2 g/mol 140.57 g/mol

Procedures: Record mass of eugenol obtained from previous weeks experiment. Weigh approximately 0.2g of eugenol in a test tube. Add 1 mL of water to test tube and add 5% aqueous KOH until oil dissolves. Add 5 drops of benzoyl chloride to the small test tube. Prepare a hot water bath and once the water is at 65 degrees Celsius, leave test tube in there for five minutes. Afterwards, cool the tube in an ice water bath. Wait until substance reaches room temperature and add 2 mL of ether. The top layer contains the product desired. Pipette the top layer into a separate tube and dry with anhydrous sodium sulfate. Filter the substance with a pipette and some cotton. Add 1mL of methanol to the substance and put tube into hot water bath until the solution has evaporated to approximately 0.5 mL. Cool the remaining substance and allow for crystals to form. Collect the crystals formed and allow for them to dry. Weigh to determine recovery yield of the experiment, obtain an IR spectrum, and determine the melting point of the crystals.

Results: Mass of crystals obtained: 0.14g (actual) Theoretical Yield calculations: 0.203g eugenol 1 mol eugenol 164.2g

1 mol EB 1 mol eugenol

268.1099g EB 1 mol EB

0.3315g EB

Theoretical Yield of EB: 0.3315g Recovered Yield: 0.14g/0.3315g=42.23% Melting point of crystals: 70C Literature Melting Point: 70C (1) Spectrum Analysis of Eugenol Benzoate Frequency (cm-1) Assignment 3062.6, 3007.3 C-H stretch 2948, 2926.2 C-H stretch 1734.88 C=O stretch 1599.2 C=C arene stretch 1261.93, 1147.38 C-O stretch Discussion: The melting point for the solid derivative was exactly the same as the literal value found from reference one. The melting point is listed as 70C for the eugenol benzoate in the preparation of eugenol benzoate handout. According to the results obtained, the solid crystals began to melt at 64C and reached completion at 70C. Thus, there appears to be no contamination of another substance in the sample solely based on the melting point results obtained. In addition, the IR spectrum for the solid crystals was very similar to the eugenol IR spectrum from the previous lab. The main differences are that the O-H stretch is no longer present in the eugenol benzoate IR. This correlates with the eugenol benzoate structure since it does not have an O-H functional group present. In addition, another main difference between the two is that eugenol benzoate has a C=O stretch and the eugenol IR spectrum does not have one. The C=O stretch present in eugenol benzoate connects the eugenol molecule with another arene ring based the structure of the solid derivative. Furthermore, the theoretical yield value was obtained by using the molar mass of eugenol and eugenol benzoate from sources two and four. The theoretical yield was mainly found by using the initial amount of eugenol put in the test tube and the two compounds have a 1:1 mole ratio based on the reaction Thus, the theoretical yield for eugenol benzoate based on the previous calculations is 0.3315g. The recovery yield of the solid is 42.23% since only 0.14g were obtained. A source of error could have been the fact that not all of the solid was transferred to the weighed filter paper since the substances were harder to acquire due to the small scale amounts used in the experiment. The overall results for the experiment were favorable ones since there was a fair recovery yield for the solid substance obtained from the main reaction in the experiment. In conclusion, the melting point of the eugenol benzoate was also exactly the same as the literature value and the IR spectrum accurately characterized the loss of an O-H stretch and the addition of a C=O stretch, or the addition of a carbonyl group. The eugenol benzoate effectively characterized the eugenol substance collected from the ground cloves.

Conclusion: The purpose of the experiment was met since a solid derivative was obtained from the reaction between eugenol and benzoyl chloride. Eugenol benzoate was obtained and it was used to characterize the eugenol isolated from the ground cloves. The melting point of eugenol benzoate was found to be 70C and the IR spectrum was very similar to the literal and to the experimental IR spectrum of eugenol. The main difference between the eugenol and the solids IR spectrums were the eugenol benzoates loss of an O-H stretch and addition of a C=O stretch due to eugenols reaction with benzoyl chloride. This suggests that the experiment was effective and that there was no contamination of unknown substance in the final products obtained. Refernces: 1. Preparation of Eugenol Benzoate (Vista Handout) 2. http://www.sciencelab.com/msds.php?msdsId=9924007 (Eugenol) 3. http://www.sciencelab.com/msds.php?msdsId=9927098 (Benzoyl Chloride) 4. http://www.chemspider.com/Chemical-Structure.56151.html (Eugenol Benzoate) 5. http://www.chem2.bham.ac.uk/schools/eugenolir.htm (literal IR spectrum for Eugenol) 6. EB=Eugenol Benzoate