Lab 3 Hall 1

Isolating of Trimsyristin from Nutmeg

Hannah Hall

Introduction

In this experiment, the student employs extraction, reflux, simple distillation, vacuum

filtration, and melting point determination in order to effectively achieve solid/liquid extraction

to isolate the triglyceride trimyristin from ground nutmeg seeds. To do this, several specific

techniques are used; extraction, reflux, simple distillation, vacuum filtration, and melting point

determination. ​A solid-liquid extraction involves the extraction of a compound from a solid using

a liquid, depending on the compound’s solubility in a particular solvent system. In this case we

are extracting trimyristin from the ground nutmeg seeds. This extraction process involves reflux,

in which a mixture is heated to the boiling point of its solvent, and the solvent vapors are then

caught, cooled, and returned to the original mixture. Following the reflux process, gravity

filtration is used to remove the trimyristin from the residue of the ground nutmeg. The solvent is

then separated from the trimyristin product using simple distillation. Finally, the trimyristin is

crystallized in an ice bath and suction filtration is used to isolate the pure crystals. The

combination of these processes are used to isolate Trimsyristin from Nutmeg, and the mel-temp

apparatus is used to confirm the identity of Trimsyristin.

Lab 3 Hall 1

Table of Reagents

Name Structure Molecular Boiling Density

Weight Point

Acetone 58.08 g/mol 56.0°C 784 kg/m³

Methylene 84.93 g/mol 39.6°C 1.33 g/cm³

Chloride

Trimyristin 723.16 g/mol 311°C 885 kg/m³

General Safety Information:

● Safety glasses and gloves should be worn at all times
● Acetone and methylene chloride: highly flammable; avoid sparks, flames and hot
surfaces. Both liquids are toxic and fumes cannot be inhaled, ensure snorkels are on and
functioning
● Methylene chloride is highly carcinogenic, take care when dispensing and distilling
● Add a boiling chip to a liquid before heating it
● Ensure apparatus has completely cooled before dismantling
● Dispose of all liquid waste in appropriately labeled bottle in lab hood

Reagent Safety:
● Acetone: ​Extremely flammable liquid and vapor. Vapor may cause flash fire. Causes eye
irritation. Breathing vapors may cause drowsiness and dizziness. Causes respiratory tract
irritation. Aspiration hazard if swallowed. Can enter lungs and cause damage. Prolonged
or repeated contact may dry the skin and cause irritation. Wash thoroughly after handling.
Remove contaminated clothing and wash before reuse. Ground and bond containers when
transferring material. Avoid contact with eyes, skin, and clothing. Empty containers
retain product residue, (liquid and/or vapor), and can be dangerous. Keep container
tightly closed. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty
containers to heat, sparks or open flames. Use only with adequate ventilation. Keep away
from heat, sparks and flame. Avoid breathing vapor.
Lab 3 Hall 1

● Methylene Chloride:​ Methylene chloride is metabolically converted to carbon monoxide

after systemic absorption, which yields increased concentrations of carboxyhemoglobin
in the blood. Harmful if swallowed. Causes eye, skin, and respiratory tract irritation. May
be harmful if inhaled. Potential cancer hazard. This substance has caused adverse
reproductive and fetal effects in animals. May cause central nervous system effects. May
cause kidney damage. Wash thoroughly after handling. Remove contaminated clothing
and wash before reuse. Avoid contact with eyes, skin, and clothing. Keep container
tightly closed. Keep away from heat, sparks and flame. Use only with adequate
ventilation. Avoid breathing vapor or mist.

● Trimyristin: ​Avoid contact with skin and eyes. Do not breathe dust. Storage Keep in a
dry, cool and well-ventilated place. Keep container tightly closed. Ensure adequate
ventilation. Use personal protective equipment.

Experimental Procedure:

Reflux:

Weigh out 4.5 grams of nutmeg and place it in a 100 mL round-bottom flask with several boiling
chips. Add 45 mL of dichloromethane. Assemble the reflux apparatus and reflux the mixture for
30 minutes which begins once the mixture flask starts to boil. As the vapor cools, a condensation
ring should be visible. Select a Variac setting that allows the ring to form about halfway up the
length of the condenser. Allow the apparatus to cool before putting it away. Hot filter your
solution into a round-bottom flask.

Simple Distillation and Filtration:

Set up a simple distillation apparatus. A temperature plateau is generally an indicator of a

successful separation of the liquids. Use a cooled flask to collect the distillate. The distillation is
stopped after all except 2-3 mL has been removed from the flask. Dispose of the distillate in the
waste container (methylene chloride). Further cool the remaining methylene chloride-trimyristin
mixture in an ice bath. The trimyristin should crystallize. To remove any remaining impurities,
add 10 mL acetone to the mixture. Swirl and separate any clumps with a stirring rod. Place the
crystals in a beaker and wash with acetone again. Collect the product using suction filtration for
5-6 minutes. Weigh the dry product (pure trimyristin) and record mass, then find the melting
point of the crystals using the Mel-Temp apparatus. Calculate percent recovery.