Transcript Final-Presentation2

Determining the Chemical Make-up
of the Flavoring of Coca-Cola
and the Degradation of
Plastic Bottles
Jill Fisher
Science Seminar
Dr. Heyen, Advisor
Purpose of Experiment, Part 1
To compare chemicals of
proposed Coca-Cola recipe
with chemicals found from
Coca-Cola product using
gas chromatography/mass
spectroscopy and ultraviolet
spectrophotometry.
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
Methods
1. Extract organic compounds with ethyl ether,
compare using gas chromatography/mass
spectroscopy (GCMS), run spectrum using
ultraviolet (UV) spectrophotometer
2. Dilute with methanol, compare using GCMS
3. Dilute with water, run spectrum with UV
spectrophotometer
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
GCMS
Coca-Cola samples
dissolved in methanol
or extracted with ethyl
ether were heated
and detected for
comparison with
chemicals in a
database.
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
UV Spectrophotometry
• Extracted and diluted CocaCola samples were ran in a
spectrum of 190 nm – 320
nm
• Diluted sample was tested
with certain wavelengths for
absorbency/%transmittance
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
Target Chemicals
Ingredient
Chemical
Citric Acid
Structure
---
Wavelength (nm)
---
Vanilla
Vanillin
279, 309
Orange Oil
Limonene
220, 250
Cinnamon Oil
Eugenol
---
Cinnamaldehyde
291
Caryophyllene
280
Linalool
243
Estragole
Lemon Oil
Coriander Oil
230, 280
---
Linalool
--See above
Pinene
Nutmeg Oil
243
210
Myristicin
---
Elemicin
---
Pinene
See above
210
Sabinene
---
Terpinene
265
Safrole
Neroli Oil
---
236, 285
NerolMake-up of Coca-Cola and the Degradation of Plastic Bottles 189-190
The Chemical
Results from GCMS
• The GCMS analysis shows the presence of
several peaks, thus several chemicals
• No exact matches, but possible derivatives of
target chemicals
Example:
Vanillin
Vanilglycolic acid
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
Vanillin derivative
Myristicin/Safrole
derivative
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
Results from Spectrophotometer
• Spectrum gave peaks
for cinnamaldehyde
and linalool
• Several targeted
wavelengths formed
one peak
• Photometer gave
individual
absorbencies for
entered wavelengths
Wavelength (nm)
ABS/%T
Target
309
-0.03/136
vanillin
291
0.40/41.3
☺cinnamaldehyde
285
0.82/15.2
safrole
280
1.40/4.0
estragole/caryophyllene
279
1.48/3.2
vanillin
265
2.33/0.5
terpinene
250
3.01/0.1
limonene
243
3.10/0.1
☺linalool
236
2.60/0.3
safrole
230
2.30/0.5
estragole
220
1.80/1.5
limonene
210
0.92/15.0
pinene
194
0.40/34.0
nerol
192
0.33/42.0
nerol
190
0.10/100
nerol
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
Target Chemicals
Ingredient
Chemical
Citric Acid
Structure
---
Wavelength (nm)
---
Vanilla
Vanillin
279, 309
Orange Oil
Limonene
220, 250
Cinnamon Oil
Eugenol
---
Cinnamaldehyde
291
Caryophyllene
280
Linalool
243
Estragole
Lemon Oil
Coriander Oil
230, 280
---
Linalool
--See above
Pinene
Nutmeg Oil
243
210
Myristicin
---
Elemicin
---
Pinene
See above
210
Sabinene
---
Terpinene
265
Safrole
Neroli Oil
---
236, 285
NerolMake-up of Coca-Cola and the Degradation of Plastic Bottles 189-190
The Chemical
Conclusions
• The secret flavoring of Coca-Cola does include
citric acid, vanilla, and cinnamon oil.
• Coriander and nutmeg oil have a high possibility
of being included.
• Recipe may have changed over the decades.
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
Purpose of Experiment, Part 2
To test for the presence of acetaldehyde in water
contained in plastic bottles under different
environments for an extended period of time.
heat
Polyethylene terephthalate (PETE)
Acetaldehyde
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
Methods
• Extract organic compounds with ethyl ether
• React aldehyde with 2,4-dinitrophenylhydrazine
• Extract organic compounds with
Solid Phase Extraction tubes
• Identify with GCMS
2,4-dinitrophenylhydrazine
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
2,4-dinitrophenylhydrazine (DNPH)
• 2,4-DNPH reagent is
made with phosphoric
acid, ethyl ether, and
2,4-DNPH
• The DNPH will react with
aldehydes to give 2,4dinitrophenylhydrazone
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
Solid Phase Extraction (SPE)
• Water is pulled through
column with suction
filtration.
• Chemicals on media are
eluted with methanol
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
Sample Environments
• Water stored for 36 days in
Greenhouse, Organic Lab, and
Microbiology Refrigerator
• Temperatures of water at
collection:
– Greenhouse: 29.5°C
– Organic Lab: 20.5°C
– Refrigerator: 6.0°C
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
Target Chemicals
DNPH Reaction
Solid Phase Extraction
• 2,4-dinitrolphenylhydrazone • Acetaldehyde
• 2,4-dinitrolphenylhydrazine • Methanol
• Ethyl ether
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
Results from GC
• Samples mixed with DNPH reagent did not give
any noticeable results
• Samples from SPE only showed excess
chemicals from greenhouse container
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
Greenhouse sample with DNPH
Organic lab sample with DNPH
Fridge sample with DNPH
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
Greenhouse sample from SPE
Organic lab sample from SPE
Fridge sample from SPE
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
Conclusion
• The DNPH did not show the presence of
acetaldehyde.
• The SPE did show a presence of a larger
compound, perhaps from the PETE or from
the silica gel matrix.
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
Acknowledgements and Thanks
Thanks to Dr. Heyen for being my advisor and
helping with the equipment and procedure.
Thanks to Diane Soldan and Caleb Mason for
chugging Coca-Cola.
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles
Sources
2,4-dinitrophenylhydrazine. Wikipedia Free Encyclopedia.
http://en.wikipedia.org/wiki/2%2C4-dinitrophenylhydrazine
Acetaldehyde. Wikipedia Free Encyclopedia.
http://en.wikipedia.org/wiki/Acetaldehyde
Cinnamon. Wikipedia Free Encyclopedia. http://en.wikipedia.org/wiki/Cinnamon
Coca-Cola. Wikipedia Free Encyclopedia. http://en.wikipedia.org/wiki/Coca-Cola_formula
Coriander. Wikipedia Free Encyclopedia. http://en.wikipedia.org/wiki/Coriander
Neroli. Wikipedia Free Encyclopedia. http://en.wikipedia.org/wiki/Neroli
Nutmeg. Wikipedia Free Encyclopedia. http://en.wikipedia.org/wiki/Nutmeg
Orange Oil. Wikipedia Free Encyclopedia. http://en.wikipedia.org/wiki/Orange_oil
Polyethylene Terephthalate. Wikipedia Free Encyclopedia.
http://en.wikipedia.org/wiki/Polyethylene_terephthalate
The Coca-Cola Recipe. Soda Museum. http://www.sodamuseum.bigstep.com/generic.jhtml?pid=10
The Safety of Convenience-Size Plastic Beverage Bottles. Plastics Info.
http://www.plasticsinfo.org/beveragebottles/apc_faqs.html
Van Aardt, Marleen. “Effect of Shelf-Life and Light Exposure on Acetaldehyde Concentration in Milk
Packaged in HDPE and PETE Bottles.” Virginia Polytechnic Institute and State University, 2000.
Vanilla. Wikipedia Free Encyclopedia. http://en.wikipedia.org/wiki/Vanilla
Weast, Robert C, ed. CRC Handbook of Chemistry and Physics. 57th Ed. Cleveland: CRC Press, 1976.
Williamson, Kenneth. Macroscale and Microscale Organic Experiments. 3rd Ed. Boston: Houghton Mifflin,
1999.
Zubrick, James W. The Organic Chem Lab Survival Manual. New Jersey: John Wiley & Sons, Inc. 2004.
The Chemical Make-up of Coca-Cola and the Degradation of Plastic Bottles