Jill Fisher

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Determining the Chemical Make-up of the Flavoring
of Coca-Colaand the Degradation of Plastic
Bottles

• Jill Fisher
• Science Seminar
• Dr. Heyen, Advisor

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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.

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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

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

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Target Chemicals
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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
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Vanillin derivative
Myristicin/Safrole derivative
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Results from Spectrophotometer

• Spectrum gave peaks for cinnamaldehyde and
  linalool
• Several targeted wavelengths formed one peak
• Photometer gave individual absorbencies for
  entered wavelengths

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Target Chemicals
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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.

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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
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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
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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

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Solid Phase Extraction (SPE)

• Water is pulled through column with suction
  filtration.
• Chemicals on media are eluted with methanol

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Sample Environments

• Water stored for 36 days in Greenhouse, Organic
  Lab, and Microbiology Refrigerator
• Temperatures of water at collection
• Greenhouse 29.5C
• Organic Lab 20.5C
• Refrigerator 6.0C

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Target Chemicals
DNPH Reaction
Solid Phase Extraction

• 2,4-dinitrolphenylhydrazone
• 2,4-dinitrolphenylhydrazine
• Ethyl ether

• Acetaldehyde
• Methanol

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Results from GC

• Samples mixed with DNPH reagent did not give any
  noticeable results
• Samples from SPE only showed excess chemicals
  from greenhouse container

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Greenhouse sample with DNPH
Organic lab sample with DNPH
Fridge sample with DNPH
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Greenhouse sample from SPE
Organic lab sample from SPE
Fridge sample from SPE
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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.

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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.

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Sources

• 2,4-dinitrophenylhydrazine. Wikipedia Free
  Encyclopedia.
• http//en.wikipedia.org/wiki/22C4-dinitrophenylh
  ydrazine
• 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/Polyeth
  ylene_terephthalate
• The Coca-Cola Recipe. Soda Museum.
  http//www.sodamuseum.bigstep.com/generic.jhtml?pi
  d10
• The Safety of Convenience-Size Plastic Beverage
  Bottles. Plastics Info. http//www.plasticsinfo.o
  rg/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.