1. Jill Fisher Science Seminar Dr. Heyen, Advisor
Determining the Chemical Make-up of the Flavoring of Coca-Cola and the Degradation of Plastic Bottles
Jill Fisher
Science Seminar
Dr. Heyen, Advisor

2. 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.

3. Methods
Extract organic compounds with ethyl ether, compare using gas chromatography/mass spectroscopy (GCMS), run spectrum using ultraviolet (UV) spectrophotometer
Dilute with methanol, compare using GCMS
Dilute with water, run spectrum with UV spectrophotometer

4. GCMS
Coca-Cola samples dissolved in methanol or extracted with ethyl ether were heated and detected for comparison with chemicals in a database.

6. UV Spectrophotometry
Extracted and diluted Coca-Cola samples were ran in a spectrum of 190 nm – 320 nm
Diluted sample was tested with certain wavelengths for absorbency/%transmittance

7. Target Chemicals Ingredient Chemical Structure Wavelength (nm)
Citric Acid
---
Vanilla
Vanillin
279, 309
Orange Oil
Limonene
220, 250
Cinnamon Oil
Eugenol
Cinnamaldehyde
291
Caryophyllene
280
Linalool
243
Estragole
230, 280
Lemon Oil
Coriander Oil
See above
Pinene
210
Nutmeg Oil
Myristicin
Elemicin
Sabinene
Terpinene
265
Safrole
236, 285
Neroli Oil
Nerol

8. 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

10. Myristicin/Safrole derivative
Vanillin derivative
Myristicin/Safrole derivative

11. Results from Spectrophotometer
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
265
2.33/0.5
terpinene
250
3.01/0.1
limonene
243
3.10/0.1
☺linalool
236
2.60/0.3
230
2.30/0.5
estragole
220
1.80/1.5
210
0.92/15.0
pinene
194
0.40/34.0
nerol
192
0.33/42.0
190
0.10/100
Spectrum gave peaks for cinnamaldehyde and linalool
Several targeted wavelengths formed one peak
Photometer gave individual absorbencies for entered wavelengths

12. Target Chemicals Ingredient Chemical Structure Wavelength (nm)
Citric Acid
---
Vanilla
Vanillin
279, 309
Orange Oil
Limonene
220, 250
Cinnamon Oil
Eugenol
Cinnamaldehyde
291
Caryophyllene
280
Linalool
243
Estragole
230, 280
Lemon Oil
Coriander Oil
See above
Pinene
210
Nutmeg Oil
Myristicin
Elemicin
Sabinene
Terpinene
265
Safrole
236, 285
Neroli Oil
Nerol

13. 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.

14. 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

15. 2,4-dinitrophenylhydrazine
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

16. 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 2,4-dinitrophenylhydrazone

17. Solid Phase Extraction (SPE)
Water is pulled through column with suction filtration.
Chemicals on media are eluted with methanol

18. 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

19. Solid Phase Extraction
Target Chemicals
DNPH Reaction
Solid Phase Extraction
2,4-dinitrolphenylhydrazone
2,4-dinitrolphenylhydrazine
Ethyl ether
Acetaldehyde
Methanol

20. Results from GC
Samples mixed with DNPH reagent did not give any noticeable results
Samples from SPE only showed excess chemicals from greenhouse container

21. Greenhouse sample with DNPH
Organic lab sample with DNPH
Fridge sample with DNPH

22. Greenhouse sample from SPE Organic lab sample from SPE
Fridge sample from SPE

23. 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.

24. 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.

25. Sources 2,4-dinitrophenylhydrazine. Wikipedia Free Encyclopedia.
Acetaldehyde. Wikipedia Free Encyclopedia.
Cinnamon. Wikipedia Free Encyclopedia.
Coca-Cola. Wikipedia Free Encyclopedia.
Coriander. Wikipedia Free Encyclopedia.
Neroli. Wikipedia Free Encyclopedia.
Nutmeg. Wikipedia Free Encyclopedia.
Orange Oil. Wikipedia Free Encyclopedia.
Polyethylene Terephthalate. Wikipedia Free Encyclopedia.
The Coca-Cola Recipe. Soda Museum.
The Safety of Convenience-Size Plastic Beverage Bottles. Plastics Info.
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.
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