Aleks Glod

TA: Lauren Pepi

Chem 2211 L
February 12, 2017
Removing Trimyristin from Nutmeg Using Solid-Liquid Extraction
I. Introduction: The purpose of this lab is to use extraction to isolate the compound of
trimyristin from commercial nutmeg using a new technique called solid-liquid extraction. Solid-
liquid extraction allows for the removal of a pure substance, like trymyristin, from permeable,
composite solids, like nutmeg seeds, based on the target compounds solubility in a solvent.
Reflux heating will be used to utilize trymyristins solubility in the solvent methylene chloride
and will prevent the escape of any vapors containing dissolved trimyristin. Along with the new
extraction and and reflux technique, previously learned techniques that will be utilized to
separate and purify trimyristin include vacuum suction filtration, simple distillation and hot
gravity filtration. Once the trimyristi has been isolated, melting point determination will be
utilized to help confirm purity and mass will be used to calculate a percent yield of trimyristin
from the original sample.
II. Experimental Procedure:
Part A: Solid-Liquid Extraction by Reflux
1. Obtain approximately 4.5 grams of ground nutmeg and place it in a 100 ml round bottom
flask.
2. Add boiling chips to the flask, then add 45 ml of the methylene chloride to the flask.
3. Build the reflux apparatus shown below in Figure 1.

4. Ensure that your system is properly clamped and cooled with water flowing through the
condenser.
5. Reflux the mixture for 30 minutes. Begin timing when the solution in the flask begins
boiling and a condensation ring forms.
6. Remove the heating mantle and allow the reflux apparatus to cool.
 7. Position the snorkel over the reflux apparatus and disassemble the apparatus.
8. Using another 100 ml round bottomed flask, short stem funnel and fluted filter paper
( refer to recrystallization experiment for reminders on how to fold filter paper into a
fluted cone) hot filtrate the solution taken from the reflux apparatus .
9. Rinse reflux flask with roughly 5 ml of fresh methylene chloride. Pour the solvent though
the filter to wash any remaining trimyristin into the catch flask.

Part B: Simple Distillation and Filtration

10. Construct a simple distillation apparatus and place boiling chips in the bottom of the
round bottom flask.
11. Distill the solution until about 2-3 ml remains in the boiling flask. Do not heat a dry flask.
12. Allow the apparatus to cool then disassemble.
13. After the flask has reached room temperature, cool the flask in an ice bath to induce
recrystallization of the trimyristin.
14. Add about 10 ml of the acetone to the cooled mixture and swirl the flask, using a stirring
rod to break up any clumps of crystal. The acetone will remove any remaining impurities
from your crystals.
15. Build a suction filtration apparatus and collect product crystals using suction filtration.
16. Move the crystals to a 100 ml beaker, rinse with 10 ml of acetone, and repeat the previous
step.
17. Dry the crystals by pulling air through the Buchner funnel for 5-6 minutes.
18. Collect and reweigh pure trimyristin crystals.
19. Determine the melting point of the purified product.
20. Calculate percent recovery.
21. Clean and store glassware in proper locations and dispose of any waste in waste container
under the fume hood.
III. Safety:
General: This lab will require students to work with boiling water, hot glassware, and
potentially harmful chemicals. Students should report any contact with chemicals, whether liquid
or vapor, to the TA immediately. Safety glasses and gloves must be worn at all times in the
organic chemistry laboratory.
i. Hot Glassware: never heat a closed vessel; always test the temperature before
handling glassware; pain and burning may occur if handled without proper
protection.

ii. Boiling Water/Liquids: Add boiling chips to any liquid before heating; monitor
boiling liquids to ensure they do not boil over; pain and burning will occur if
boiling liquids are touched without protection

Reagent Safety:
 i. Acetone: It can be inhaled or ingested, causes irritation to eyes, nose, throat;
headache, dizziness, central nervous system depression and dermatitis. If comes
in contact with eyes or skin proceed to wash. If wet, then it can be flammable.

ii. Methylene Chloride (Dichloromethane) : Can enter the body through means of
inhalation, skin absorption, ingestion, skin and/or eye contact, leading to an
individual experiencing irritation to eyes, skin; weakness or exhaustion,
drowsiness, dizziness; numbness, tingle limbs and nausea. It is considered a
potential occupational carcinogen.

iii. Trimyristin: Eye contact may cause irritation, redness or tears; skin contact may
cause redness, irritation, dry skin or allergic reaction; ingestion may cause
irritation or nausea; inhalation may cause coughing or irritation and a burning
sensation in the throat and lungs.
IV. Table of Reagents:
Compoun Structure Molecular Boiling Point Density Melting
d Name weight(g/mol) (C) point

Citations
"Acetone." Acetone | C3H6O | ChemSpider. Royal Society of Chemistry 2015, n.d. Web. 12 Feb.
2017. <http://www.chemspider.com/Chemical-Structure.175.html?rid>.
"Dichloromethane." Dichloromethane | CH2Cl2 | ChemSpider. Royal Society of Chemistry
2015, n.d. Web. 12 Feb. 2017. <http://www.chemspider.com/Chemical-Structure.6104.html?
rid=1e136cd5-fefd-4664-99a5-3153a2c56338>.
"Trimyristin." Trimyristin | C45H86O6 | ChemSpider. Royal Society of Chemistry 2015, n.d.
Web. 12 Feb. 2017. <http://www.chemspider.com/Chemical-Structure.10675.html?
rid=63721d36-859c-4cb9-9798-113d9e758d0b>.