Limonene Lab Report

Part 1: Esters aromas are very distinct and often pleasant, they are often used in food aroma and fragrances.1 Esters chemical properties are distinguished by their low molecular weight and low boiling points, caused by their dipole-dipole and dispersion interaction.2 Esters are the result of a condensation reaction, in which a carboxylic acid, an alcohol, and an acid catalyst react to create a water molecule and an ester.

14 mL of 9 M H2SO4 was added to the separatory funnel and the mixture was shaken. The layers were given a small amount of time to separate. The remaining n-butyl alcohol was extracted by the H2SO4 solution therefore, there was only one organic top layer. The lower aqueous layer was drained and discarded. 14 mL of H2O was added to the separatory funnel. A stopper was placed on the separatory funnel and it was shaken while being vented occasionally. The layers separated and the lower layer which contained the n-butyl bromide was drained into a smaller beaker. The aqueous layer was then discarded after ensuring that the correct layer had been saved by completing the "water drop test" (adding a drop of water to the drained liquid and if the water dissolves, it confirms that it is an aqueous layer). The alkyl halide was then returned to the separatory funnel. 14 mL of saturated aqeous sodium bicarbonate was added a little at a time while the separatory funnel was being swirled. A stopper was placed on the funnel and it was shaken for 1 minute while being vented frequently to relieve any pressure that was being produced. The lower alkyl halide layer was drained into a dry Erlenmeyer flask and 1.0 g of anhydrous calcium chloride was added to dry the solution. A stopper was placed on the Erlenmeyer flask and the contents were swirled until the liquid was clear. For the distillation

Materials: In lab 3, we used 75 g of cloves from which we must extract Eugenol. Water was largely used as a solvent. A polar solvent used was Dichloromethane. The drying agent used was Calcium Chloride. An acid and a base used were hydrochloric acid and Sodium Hydroxide, respectfully. The

1.5mL of phosphoric acid including 3-4 boiling chips were also added to the 25mL flask. The short path distillation apparatus was set up as shown in Figure 1. A heating mantle was used to heat up the 25mL flask. The solution was distilled to the receiving flask until a small amount of liquid remained in the initial RBF flask. At this point the presence of thick grey smoke pulling over into the entire apparatus was observed. The apparatus was then left to cool down. Through the use of pasture pipette, the aqueous layer from the distilled solution was drawn out. Sodium carbonate was then added to the remaining organic solution in order to check the pH and to verify the basicity of the solution. The aqueous layer was again drawn out from the solution. Next, 0.5g of sodium sulfate was added to the remaining organic layer and was swirled until the liquid appeared to be dry and clear. The alkenes were transferred into a clean 10mL flaks using another clean pasture pipe. The apparatus from the first distillation was rinsed off with

After about 1 minute of shaking, the two layers separated. The organic layer on the top layer (consisted of ethyl acetate and naphthalene) collected for further experiment; by adding Sodium Sulfate into organic phase and filtering the Na2So4 from the solution using the wool. The dried organic layer was weighed to get its mass and the residue of Na2SO4 were rinsed with ethyl acetate under vacuum (rotary evaporator). The acid extract on the bottom layer which is a combination of benzoic acid and NaOH were collected in the 50 mL Erlenmeyer beaker for the recovery of acid.

In this experiment, a mixture of unknown #3 was used. That mixture had acid, base, and neutral. We added solvent to the unknown. It is important to know the density of the solvent in order to determine which is the aqueous layer and which is the organic layer. If the solvent that has more density than water, so the organic layer will be the lower layer, while if the solvent has lower density than water, the organic layer will be the upper layer. This will make an error if the determination of the layers was wrong after added the strong acid or the strong base. We added 5% HCl to the mixture in order to separate the base in the aqueous layer and form its salt. Same thing, we add 5% NaOH to the mixture in order to separate the acid and form its salt. In order to recover the base, we add 10% NaOH to the HCl extraction. The result will be salt with a base. Same thing for the acid, in order to recovered it, we added 10% HCl. The reaction will give us salt with an acid. For the neutral, we added sodium sulfate as a drying reagent in order to dry water and separate the neutral part as pure.

To start off, in an Erlenmeyer flask approximately 0.51 g of E-stilbene with 10 mL of acetic acid was dissolved. A hot water bath was prepared and the mixture was warmed until the solid is completely dissolved. After the solution was dissolved, 1.02 gram of pyridinium hydromide perbromide was added. The crystals around the flask were rinsed with a small amount of acetic acid and the solution was continued in the hot water bath for one to two minutes.

The purpose of this laboratory experiment was to isolate and characterize clove oil in order to understand how to isolate organic compounds with high boiling points, how to perform and interpret qualitative tests for organic compound functionality, and to continue to learn how to perform and interpret IR spectrometry. Steam distillation was used in order to prevent the organic compound from decomposing at temperatures approaching the compound's boiling point.

In this experiment, 0.31 g (2.87 mmol) of 2-methylphenol was suspended in a 10 mL Erlenmeyer flask along with 1 mL of water and a stir bar. The flask was clamped onto a hotplate/stirrer and turned on so that the stir bar would turn freely. Based on the amount of 2-methylphenol, 0.957 mL (0.00287 mmol) NaOH was calculated and collected in a syringe. The NaOH was then added to the 2-methylphenol solution and allowed to mix completely. In another 10 mL Erlenmeyer flask, 0.34 g (2.92 mmol) of sodium chloroacetate was calculated based on the amount of 2-methylphenol and placed into the flask along with 1 mL of water. The sodium chloroacetate solution was mixed until dissolved. The sodium chloroacetate solution was poured into the 2-methylphenol and NaOH solution after it was fully dissolved using a microscale funnel.

Initially, the entire impure product was mixed with diethyl ether for extraction. Upon mixing, the solution separates into two layers; an organic layer and an aqueous layer. The organic layer contains the desired product. Additional extractions using sodium carbonate solution and sodium hydroxide solution were used as well to ensure removal of undesired molecules. The reason that two layers form is due to the fact that water is immiscible with organic products and diethyl ether meaning that they do not dissolve into one another.

Dispense .5 mL water into the already weighed conical vial, replace cap and face insert on its down side.

“Present in the leaves are severl phenolic compounds such as protocatechuic acid, ferulic acid, quercetin and guavin B” [10], “quercetin, ascorbic acid, gallic acid and caffeic acid Others include Terpenoids and flavonoids such as Oleanolic acid Nerolidiol, β-sitosterol, ursolic, crategolic and guayavolic acids as well as essential oil including α-pinene, β-pinene, limonene, menthol, terpenyl acetate, isopropyl alcohol, longicyclene, caryophyllene, β-bisabolene, cineol, caryophyllene oxide, β-copanene, farnesene, humulene, selinene, cardinene and curcumene” [9].

Eucalyptol is also known as 1,8-cineole (1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane) is a monocyclic monoterpene ether (oxide) (figure 1) with an aromatic and camphor like odour found in essential oils of Eucalyptus globules, Eucalyptus polybractea (not less than 70% of Eucalyptol)1, Helichrysum gymnocephalum (47.4% Eucalyptol)2 ,Zingiber chrysanthum Rosc. (42% Eucalyptol) 3 and many other aromatic plants. Because of its pleasant spicy aroma and taste, eucalyptol is used in flavouring agent, fragrances, and cosmetics. Eucalyptol is listed in Code of Federal Regulation as Flavouring Agents and Related Substances 4. Eucalyptol has been considered as generally recognised as safe (GRAS)

The main objective of the lab work done was the extraction of eugenol from cloves, after which a calculation of the the percentage recovery of it is researched, and to the running of an IR in order to analyze the purity of the lab sample. Eugenol is the byproduct of the oil extract from cloves. This produced oil consists of mostly eugenol and acetyleugenol. In medical purposes, the oil could be used as a dental anesthetic. It is also one of the best over the counter cure for a toothache. (Kluger, 2016) Dentists use it as an antiseptic and anti-inflammatory weapon agains dental pain for patients, as well as to kill germs. Because some research shows that eugenol is a good weapon against bacteria and other harmful dental threats, Eugenol is often

Cinnamaldehyde, cinnamic aldehyde or 3-phenyl-2-propenal is the major constituent of cinnamon oil, extracted from several species of Cinnamomum (C. verum, C. burmanii, C. cassia), under the family Lauraceae, a group of evergreen trees. Cinnamon bark (particularly C. verum) yields 0.4-0.8% oil, which contains 60-80% cinnamaldehyde, 4-5% sesquiterpenoids (α-humulene, β-caryophyllene, limonene and others), eugenol, cinnamyl acetate, eugenol acetate, cinnamyl alcohol, methyl eugenol, benzaldehyde, benzyl benzoate, cuminaldehyde, monoterpenes (linalool, pinene,