Gas Chromatography Investigations 2009 Vernier Software & Technology 2 - 1

Experiment
2
Verification of Esterification
Esters compose an important class of organic compounds. Esters often have a pleasant scent and
are found in natural fragrances. Esters can be prepared synthetically for use in foods, flavorings
and perfumes. Ethyl acetate is often used as a solvent in fingernail polish remover. Polyesters are
used in fabrics and clothing.
The esterification process produces esters through a condensation reaction. Condensation
reactions have water as one of the products. The reactants for esters are an alcohol and an acid
(either an organic or an inorganic acid). A catalyst, such as concentrated acid or an ion echange
resin, is added to accelerate the reaction. This reaction will not go to completion, but instead
reaches e!uilibrium after an amount of time. The e!uilibrium can be shifted toward the product
by adding more reactants or removing products.
Although the esterification reaction produces water as a ma"or product, the mechanism is not an
acid#base neutrali$ation reaction. The esters are named as salts of the acids prefaced with name
of the alcohol. Eamples are shown in the chart.
Alcohol Acid Ester Odor
methyl acetic methyl acetate sweet
ethyl acetic ethyl acetate fruity
isoamyl acetic isoamyl acetate banana
isoamyl butyric isoamyl butyrate pear
%n this eperiment you will conduct the reaction between ethyl alcohol and acetic acid. &y
in"ecting a sample of the reaction miture into a 'ernier (ini )C you will follow and confirm
the production of the ester ethyl acetate.
OBJECTIVES
%n this eperiment, you will
Conduct an esterification reaction to produce ethyl acetate.
(easure and analy$e the )C retentions time of the reactants and products involved in
synthesi$ing ethyl acetate.
(easure and analy$e the )C retentions time of the reaction miture to confirm the
production of ethyl acetate.
MATERIALS
'ernier (ini )C glacial acetic acid
computer or *ab+uest ethanol, ,-.
*ogger Pro / or *ab+uest App ethyl acetate
Temperature Probe 0owe -1 2 ion echange resin
3 * glass syringe acetone
plastic &eral pipets 4imwipes
5
or paper towels
three test tubes, 2- 211 mm Parafilm
5
or cor6 stoppers for test tubes
test tube rac6 hot plate
test tube clamp ice bath
two 2-1 m* bea6ers
2 - 2 Gas Chromatography Investigations
Eperiment 2
SAET!
Please adhere to the following safety concerns as you prepare and conduct this eperiment.
4eep the reagents away from open flames.
)lacial acetic acid is a strong irritant to the nose, s6in and eyes.
*ocate the eyewash and acid safety stations in the laboratory.
"ROCE#$RE
"art I% #etermine the &C Retention Times for the Indi'id(al Reactants and "rod(cts
3. 7btain and wear goggles.
2. 7btain a glass syringe and a set of vials of ethanol, glacial acetic acid, and ethyl acetate.
CAUTION8 Handle the glacial acetic acid with care. It can cause painful burns if it comes
in contact with the skin.
Important8 The glass syringe is fragile and can be easily damaged. &e careful not to bend the
needle or bend the plunger. %f the plunger is accidentally pulled out of the glass barrel, reinserting
it is etremely difficult, sometimes impossible.
/. Prepare the 'ernier (ini )C for data collection.
a. Turn on the (ini )C.
b. Connect the 9:& cable of the (ini )C to the 9:& port on your computer or *ab+uest.
c. :tart the data#collection program, and then choose ;ew from the <ile menu.
d. Clic6 Collect in *ogger Pro, or tap = in *ab+uest, to bring up the Temperature#Pressure
profile.
e. :et the Temperature#Pressure values to8
Start temperature 35C
Hold time 1 min
Ramp rate 5C/min
Final temperature 45C
Hold time 5 min
Total lenth !"# min
$ressure 3"5 %$a
f. :elect 0one to initiate the (ini )C warm up. ;ote8 A new message will appear, >0o not
in"ect until )C is ready?, and the *E0 on the (ini )C is red. The (ini )C will ta6e a
few minutes to warm up and stabili$e. @hen the (ini )C is ready for in"ection, the
message will read, >%n"ect and select Collect simultaneously?, and the *E0 will turn to
green. @hile the mini )C is warming up, complete :teps A and -.
Gas Chromatography Investigations 2 - 3
Verification of Esterification
A. <ollow the steps below to clean and flush the syringe with ethanol. Important8 The glass
syringe is fragile. &e careful not to bend the needle or bend the plunger. ;ever pull the
plunger bac6 more than -1. of its total volume. &e careful not to bend the plunger as you
press it down.
a. 0epress the plunger fully.
b. :ubmerge the tip of the syringe needle into the vial of ethanol.
c. Pull bac6 the plunger to fill the barrel about 3B/ full of ethanol. Eamine the barrel of the
syringe and estimate the amount of ethanol in the barrel.
d. Epel the li!uid onto a 4imwipe or a paper towel.
e. Cepeat :teps aDd at least two times, until you are comfortable pulling up a li!uid into the
syringe and measuring the volume in the syringe barrel. 9se a 4imwipe or a paper towel
to carefully pat around the tip of the syringe needle.
-. Collect a volume of ethanol for in"ection.
a. :ubmerge the needle into the vial of ethanol
one last time.
b. 0raw up approimately 1.2 * of li!uid. %t is
not critical that the volume be eactly 1.2 *.
c. After collecting your sample, gently wipe the
needle from barrel to tip, with a 4imwipe.
E. Prepare for in"ection and the start of data collection. %t is important for you and your lab
partner to divide the tas6s in this step. 7ne person will operate the syringe and the other
person will operate the computer controls.
a. @hen the (ini )C has reached the correct start temperature
and pressure, the message reads, >Ceady to %n"ect,? and the
*E0 on the (ini )C is green.
b. To insert the needle of the syringe into the in"ection port of
the (ini )C, hold the syringe with one hand and steady the
needle with your other hand. %nsert the needle into the
in"ection port until the needle stop is fully seated, as shown
in <igure /. %f the needle stic6s, rotate it slightly while
inserting. 0o not move the plunger yet.
c. :imultaneously, depress the syringe plunger and select
Collect to begin data collection. Pull the needle out of the
in"ection port immediately.
F. @hile the data collection proceeds, repeat :tep A and use ethyl acetate to thoroughly clean
the syringe and needle. %t may ta6e three or more flushes to feel the syringe plunger move
smoothly again, which is your indicator that the syringe and needle are both suitably clean.
G. 0ata collection will end after eight minutes. 7bserve the graphed data that characteri$es an
ethanol chromatogram.
Figure 2
Figure 3
2 - 4 Gas Chromatography Investigations
Eperiment 2
,. Analy$e your chromatogram.
a. Choose Pea6 %ntegration from the Analy$e menu.
b. :elect and integrate the left#most pea6. To do this, drag from a little before the pea6 to a
point far enough to the right that includes all of the pea6. Then choose Add.
c. Cecord the retention time and pea6 area in your data table.
d. To analy$e another pea6 on the same graph, repeat :teps b and c.
e. Enter the name of the compound, if 6nown.
f. @hen you are finished with all of the pea6s, select 74.
31. (optional) Hou can choose to save this chromatogram and pea6 analysis for later use, with a
uni!ue file name, by choosing :ave from the <ile menu.
33. Test the ethyl acetate sample.
a. Clic6 Collect in *ogger Pro, or tap & in *ab+uest, to bring up the Temperature#Pressure
profile. This profile will be the same as for your previous run. %f you are satisfied with
these values, clic6 74 to initiate the (ini )C profile.
b. @hile the (ini )C ad"usts to its Temperature#Pressure profile, repeat :teps A and - with
the ethyl acetate sample.
c. After the (ini )C is ready, repeat :teps ED31.
32. Cepeat :tep 33 for the glacial acetic acid sample.
"art II% Cond(ct the Esterification Reaction
3/. Place the hot plate in a hood. Prepare a water bath by pouring approimately 321 m* water
into a 2-1 m* bea6er and place it on the hotplate. 9se a temperature probe or thermometer to
monitor the temperature of the water bath. Turn on the hot plate and warm the water
temperature to between E-DF1C.
3A. Add ice and cold water to a second 2-1 m* bea6er. This will be the !uenching bath. Place
this bea6er near the hot water bath.
3-. Place three test tubes in a rac6. *abel the test tubes 1, 2 and 3. 9se a spatula to place a small
amount of 0owe ion#echange resin into each test tube. Add the resin to barely cover the
bottom of the test tube. The eact amount of resin is not importantI its function is to act as a
surface catalyst.
3E. 9se separate plastic &eral pipettes to add J3 m* (J2- drops) of glacial acetic acid and
ethanol to each test tube. 9se a small s!uare of Parafilm or a cor6 stopper to seal each test
tube. (a6e a pin hole in the Parafilm, or fit the cor6 stopper loosely on the test tube, for a
pressure release.
3F. Carefully transfer the three test tubes, at the same time, to the hot water bath on the hot plate.
Important: :tart timing the reactionI you will be removing the test tubes, one at a time, at
twenty minute intervals.
3G. (onitor the water temperature. %f it drops below E-
o
C, turn up the heatI if it rises above F1
o
C,
turn the heat down or off and add some cold water.
3,. At the end of twenty minutes, remove test tube 1 from the hot plate and place it in the cold
water bath for two minutes to !uench the reaction.
Gas Chromatography Investigations 2 - 5
Verification of Esterification
21. <ollow :tep 33 to in"ect a sample from test tube 3. Important8 The chromatogram for this
sample will contain more than one pea6. Cecord the retention time and pea6 area for each
pea6 and write down this information in your data table.
23. After forty minutes, remove test tube 2 from the hot plate and place it in the cold water bath
for two minutes to !uench the reaction. <ollow :tep 33 for the contents of test tube 2.
22. After sity minutes, remove test tube 3 from the hot plate and place it in the cold water bath
for two minutes. <ollow :tep 33 for the contents of test tube /.
2/. After you have tested your final sample, flush and clean the syringe with acetone. Turn off
the (ini )C.
2 - 6 Gas Chromatography Investigations
Eperiment 2
#ATA TABLE
"art I Res(lts
Compound
Retention time
'min(
$ea% area
ethanol
acetic acid
ethyl acetate
"art II Res(lts
Sample
Retention
time
'min(
$ea% area )dentity * +rea
Test tube 1, pea% 1
Test tube 1, pea% -
Test tube 1, pea% 3
Test tube -, pea% 1
Test tube -, pea% -
Test tube -, pea% 3
Test tube 3, pea% 1
Test tube 3, pea% -
Test tube 3, pea% 3
Gas Chromatography Investigations 2 - 7
Verification of Esterification
#ATA A)AL!SIS
3. 0id the reaction between acetic acid and ethanol produce ethyl acetateK Eplain how you
used chromatographic data to analy$e the esterification reaction.
2. 0id the )C test results after 21, A1, and E1 minutes show significant differences in the
progress of the reactionK :upport your answer with data.
/. :uggest factors that would cause a low yield of the ester in the reaction.