Denisse Cuarteros

Chem 243A-005

Laboratory 6A: Hydrogenation


1. For the hydrogenation reaction, which phases of matter are present, and which
reaction components are present in which phase?

The goal of the experiment is to turn methyl oleate (a liquid monounsaturated
fatty acid) into solid, through a process called catalytic hydrogenation by using Hydrogen
gas (

) and a catalyst, 10% Pd/C which is a solid (metal) and is insoluble in the solvent
used. Hydrogenation is a very slow process unless theres a catalyst that makes it possible
to convert the unsaturated fatty acid into a saturated fatty acid (methyl stearate) because it
increases the rate of reaction by decreasing the activation energy required. Catalytic
hydrogenation is a type of heterogeneous reaction because different components of
reaction are involved and are present in different phases such as solid, liquid, and gas
phases.

2. Which peaks are present in the IR spectrum of methyl oleate and methyl stearate?
What is the main difference and why?

Groups Present Methyl oleate Methyl stearate
Ester

(~1743.29

(~1742.57

Phenyl shoulder (~3000

H-C=C (shoulder) (~1743.29

The main difference between methyl oleate and methyl stearate is that, methyl
stearate doesnt have C=C shoulder and H-C=C shoulder present on the IR spectrum.
Methyl oleate is an unsaturated fatty acid ester, which has an alkene (groups with C=C
bonds), hydrocarbons, and ester group, compared to methyl stearate which is a saturated
fatty acid ester which contains hydrocarbons, methyl group, and ester group. Methyl
oleate has lower melting point than methyl stearate because the double bond in the
methyl oleate creates restriction in movement whereas the straight long hydrocarbons of
the methyl stearate has more freedom in movement. Since methyl stearate has more
freedom in movement, it needs a higher temperature or energy to break the bonds.


Denisse Cuarteros
Chem 243A-005



3. Why is methyl stearate (the product) a solid and methyl oleate a liquid? Explain in
terms related to the structure of these fatty acid methyl esters.
Methyl oleate is a monounsaturated fatty acid and thus, has a lower melting
point (approximately -20 degrees Celsius) than methyl stearate which is a saturated fatty
acid. Methyl oleate is liquid at room temperature because it has way lower melting point
than the average room temperature (approximately 20-25 degrees Celsius). Methyl
stearate is a solid at room temperature because it has an approximate melting point of 37
degrees Celsius. Because of the long straight hydrocarbons that the methyl stearate
contains, it will take a higher penalty to break the bonds resulting in higher melting point,
thus allowing it to be solidified at a temperature thats lower than 37 degrees Celsius.