1. Synthesis and Resolution of a Substituted Dioxolane From Glycerol
Susannah Cox, Stacy O’Reilly

2. Common Uses of Glycerol
Sugar substitute and food filler
Window Washing Fluid
Beauty products
Preservative
Nitroglycerin
Triglyceride backbone
Glycerol is a clear and colorless viscous liquid that is commonly used as a preservative for leaves, and as a filler in “low-fat” foods and sugar substitute in the food industry, It also is used in suppositories, as well as in number of other personal-care goods, including mouthwash, toothpaste, hair and skin products. As a chemical intermediate, glycerol is utilized in the production of nitroglycerin as well as smokeless gunpowder and dynamite.

3. Purpose
Transform cheap and abundant glycerol into a chemical feedstock for the production of more complicated species.
Chemical Feedstock: A minimally processed material that is used to synthesize other chemicals.
Ideal chemical feedstocks are cheap, plentiful, renewable and safe.
Currently, most chemical feedstocks are petroleum based.

4. Chemical Feedstock
Differentiate the two ends of the glycerol with acetal
Removal of the acetal to resolve diastereomers
Allows for reactivity at all three –OH sites as well as chiral control
Resolve enantiomers
Making the acetal to differentiate the two ends of the glycerol
Once the acetal is removed can resolve diasteromers
Reactivity at all three sites and chiral control

5. Biofuel Production
Formation of biofuels and glycerol as waste material
Saponification of the fatty acid

6. Why Glycerol? By-product of biofuel production. Triglyceride backbone
Abundant waste material
By 2020, glycerol production
will exceed its demand by six
fold due to increased biofuel production.

7. Formation of Acetal General Reaction
*Graham, Andrew E., Tomasz M. Kubczyk, and Brendan M. Smith. “Metal triflate catalysed acetal exchange reactions of glycerol under solvent-free conditions.” RSC Advances. The Royal Society of Chemistry, 21 Feb. 2012: Web. 13 July 2012.

8. Formation of Acetal Specific Examples Focused on acetone
Incomplete reactions
Focused on acetone
Allowed study of chirality
Clean ring formation
*Graham, Andrew E., Tomasz M. Kubczyk, and Brendan M. Smith. “Metal triflate catalysed acetal exchange reactions of glycerol under solvent-free conditions.” RSC Advances. The Royal Society of Chemistry, 21 Feb. 2012: Web. 13 July 2012.

9. HNMR Analysis of Acetal
Eight unique hydrogen signals

10. Formation of the Ester
Exploiting chiral carbon to resolve diastereomers * *

11. Formation of the Ester
“R-Groups”

12. HNMR Analysis of the Ester
Synthesis affected by the presence of an acid

13. Formation of the Ester Reaction with S-Mosher’s Acid Chloride
Single product formed when two expected

14. HNMR Analysis of the Ester
Characteristic methyl groups

15. CNMR Analysis of the Ester
Only one product formed

16. Future Work
Optimize methods for reactions and isolation procedures to improve yields.
Experiment with chirality of the ester produced from the reaction with Mosher’s Acid.
Find other ways to elaborate the acetal formed from glycerol.
Attempt to resolve the diastereomers
Continue to try and develop reactions that take into consideration the safety of the materials used and the amount of waste produced.

17. Acknowledgements
Thanks to the Butler Chemistry Department for supplying reaction materials and lab space.
To Dr. Stacy O’Reilly, Dr. LuAnne McNulty, Dr. Anne Wilson, and Dr. John Esteb for their professional insight.
Also to BSI for funding my summer of research.

18. Works Cited
“Biodiesel.” Wikipedia, The Free Encyclopedia. Wikimedia Foundation, Inc. 17 Jan Web. 18 Jan  
Ciriminna, Rosaria, Cristina Della Pina, Hiroshi Kimura, Mario Pagliaro, and Micele Rossi. “From Glycerol to Value-Added Products.” Angewandte Chemie. Wiley Interscience, 2007: Web. July 2012. 
Graham, Andrew E., Tomasz M. Kubczyk, and Brendan M. Smith. “Metal triflate catalysed acetal exchange reactions of glycerol under solvent-free conditions.” RSC Advances. The Royal Society of Chemistry, 21 Feb. 2012: Web. 13 July 2012. 
March, Jerry, and Michael B. Smith. “ Direct Conversion of Alkyl Halides to Aldehydes and Ketones.” March’s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 5th ed. United States of America: John Wiley & Sons, Inc, Print.