Category
Oral - Basic
Description
Bisphenol A (BPA, 4-[1-(4-hydroxyphenyl)-1-methylethyl]phenol) is a monomer utilized to produce epoxy resins and in thermal printing processes. Two primary problems are posed by the production of BPA: It is environmentally and toxicologically damaging. If a molecule that mimicked the properties and structure of BPA yet lacked its toxicologically damaging effects could be manufactured from renewable sources these concerns could be greatly reduced. One such monomer is bisguaiacol F (BGF, 4-[(4-Hydroxy-3-methoxyphenyl)methyl]-2-methoxyphenol). While BGF mimics BPA, typical reaction mechanisms require a laborious workup resulting in diminished yield and purity. We hypothesize that utilizing microwave assistance in the synthesis of BGF will ultimately increase the efficiency and renewability of the reaction, as well as the purity of the product. BGF was synthesized by electrophilic aromatic coupling of vanillyl alcohol and guaiacol. In preliminary experiments, Amberlyst resin was used as the acidic catalyst in water. Reactions run at 65° C and 100° C resulted in moderate yields (40-60%) of a mixture of p,p’ and o,p’ isomers following laborious workup and purification. An additional reaction was run using ethanol as a solvent and sulfuric acid as a catalyst and produced low yields (15.6%) of BGF. Current conclusions indicate that reaction conditions of water and Amberlyst resin reacted at higher temperatures produce higher yields of BGF. Future work involves utilization of microwave assisted synthesis to optimize the synthesis BGF. Water and Amberlyst resin will be used to establish baseline conditions concerning optimal time, temperature, and heating rate. Once determined, solvent (i.e. DMF, ethanol, DME) and catalyst (i. e. Amberlyst resin, sulfuric acid, functionalized silica gel) will be varied to determine which combination produces the greatest yield and purity of p,p’ BGF. Simplification of reaction workup and purification will be investigated throughout the project.
Optimization of bisguaiacol F Synthesis via Microwave Assistance
Oral - Basic
Bisphenol A (BPA, 4-[1-(4-hydroxyphenyl)-1-methylethyl]phenol) is a monomer utilized to produce epoxy resins and in thermal printing processes. Two primary problems are posed by the production of BPA: It is environmentally and toxicologically damaging. If a molecule that mimicked the properties and structure of BPA yet lacked its toxicologically damaging effects could be manufactured from renewable sources these concerns could be greatly reduced. One such monomer is bisguaiacol F (BGF, 4-[(4-Hydroxy-3-methoxyphenyl)methyl]-2-methoxyphenol). While BGF mimics BPA, typical reaction mechanisms require a laborious workup resulting in diminished yield and purity. We hypothesize that utilizing microwave assistance in the synthesis of BGF will ultimately increase the efficiency and renewability of the reaction, as well as the purity of the product. BGF was synthesized by electrophilic aromatic coupling of vanillyl alcohol and guaiacol. In preliminary experiments, Amberlyst resin was used as the acidic catalyst in water. Reactions run at 65° C and 100° C resulted in moderate yields (40-60%) of a mixture of p,p’ and o,p’ isomers following laborious workup and purification. An additional reaction was run using ethanol as a solvent and sulfuric acid as a catalyst and produced low yields (15.6%) of BGF. Current conclusions indicate that reaction conditions of water and Amberlyst resin reacted at higher temperatures produce higher yields of BGF. Future work involves utilization of microwave assisted synthesis to optimize the synthesis BGF. Water and Amberlyst resin will be used to establish baseline conditions concerning optimal time, temperature, and heating rate. Once determined, solvent (i.e. DMF, ethanol, DME) and catalyst (i. e. Amberlyst resin, sulfuric acid, functionalized silica gel) will be varied to determine which combination produces the greatest yield and purity of p,p’ BGF. Simplification of reaction workup and purification will be investigated throughout the project.
Comments
Undergraduate - 2nd Place Award Winner