PittConn 2019

Pittsburgh Conference Memorial National College Grants Program

...form the PittConn website...

The Pittsburgh Conference on Analytical Chemistry and Applied Spectroscopy (a Pennsylvania non-profit Corporation) and its co-sponsoring technical societies, The Society for Analytical Chemists of Pittsburgh (SACP) and The Spectroscopy Society of Pittsburgh (SSP) proudly announce the 2020 Pittsburgh Conference Memorial National College Grants (PCMNCG) Program.

Grants will be awarded to small college science departments for the purchase of scientific equipment, audio-visual or other teaching aids, and/or library materials for use in the teaching of science at the undergraduate level.

The amount requested in each proposal may not exceed $10,000. Submission deadline is October 31, 2019.

2020 Proposal

Monmouth College's Chemistry Department (ACS certified) has made the commitment to the ACS 12 green chemistry principles. Our program has recently signed the Green Chemistry Commitment (BeyondBenign.com) and will utilize these resources to guide the implementation of these principles throughout our curriculum. As a part of this initiative, we have begun to explore the use of microwave synthesis technologies in three parts of our academic program: 1) organic chemistry labs, 2) physical chemistry lab, and 3) a few selected research projects. All chemistry and biochemistry majors take a 1-year organic course, 1/2 or 1-year physical chemistry course, and a 1-year research experience; many biology students take these courses as well. Future plans include the use of this technology in our inorganic and general chemistry labs, as well as our upper-level integrated lab course. At this time our department has 65 majors (50/50 male/female), graduate ~14 students per year, and over the past 5 years, 25% of our students have continued into professional programs (medical, pharmacy, dental, etc), 30% have continued into graduate programs, and 40% have pursued employment within industry. Monmouth College is grateful to the PCMNCG Program for past funding.

We propose to purchase an Anton-Paar Monowave 400 unit (~$23k, request $10k with $13k match). This instrument will be used in conjunction with our suite of analytical instruments to study and implement small-scale, synthesis reactions, as well as study the principles and applications of microwave technologies. Anton-Paar offers a low-cost (~$5k) microwave synthesis unit designed for small scale microwave reactions, but we have chosen to purchase the Monowave 400 due to the additional features which include real-time monitoring of temperature, pressure, power, as well as the built-in camera to visualize the reaction mixture. As our program integrates microwave technologies into other program areas, additional low-cost microwave reactors can be added to increase the throughput of reactions.

Anton-Paar Microwave-Assisted Synthesis Wiki

Use in Organic Chemistry

During the 2019 MACTLAC conference at St. Catherine's University, Anton-Paar, in conjunction with the St. Kate's Organic Professor Jame Wollack. shared a collection of 5 organic chemistry lab activities, currently in use, that contrast conventional and microwave synthesis techniques. The synthesis of cinnamic acid derivatives by Pellon, et al. (2000) [Syn. Comm., 30(20), pp. 3769-3774] highlights the early use of the microwave synthesis technique. Professor Wollack has adapted this lab activity for use with the Anton-Paar Monowave 400 instrument; products are evaluated using NMR analysis. Other successful lab activities include:

- Nitration of Phenol, using Silica column and TLC chromatography.

- Fischer Esterification: Synthesis of Flavorings and Scents, using GC and NMR analysis, as well as olfactory senses.

- Base Bulkiness Effects on Elimination of 2-Bromoheptane, using GC analysis.

- Microwave Assisted Diels-Alder Reaction, using NMR, GC, and IR analysis.

- Synthesis of Chalcone and Avobenzone, using NMR analysis.

Use in Physical Chemistry

The development of thermodynamic principles required the knowledge of whether a reaction/process was being done under constant pressure conditions (open systems) or under constant volume conditions (closed systems). It is traditional to contrast these types of processes using a solution (coffee-cup) calorimeter (open system/constant pressure) verses a bomb calorimeter (closed system/constant volume). Most organic reactions are done using constant pressure (open) reactors, which limits the reaction temperatures to the solvent boiling point. When using a microwave reactor, the reactions are under constant volume (closed) conditions hence are no longer constrained by the solvent boiling point. As noted above, the Anton-Paar Monowave 400 instrument monitors/displays the reaction temperature, pressure, and input energy; having access to this data provides additional insights into the reaction chemistry.

Use in Research Activities

Synthesis of Lignin Monomers.

Lignin is a biopolymer composed of three substituted phenol monomer units, p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol. These monomers differ by the number of methoxy substituents. Although lignin chemistry is very interesting, we are particularly interested in the dimer lignin products, called lignans, due to their biological activity. The lignin monomers are quite costly, but the corresponding carboxylic acid forms can be purchased at a reasonable cost. For this reason we have been synthesizing the lignin monomers by carrying out an esterification of these carboxylic acids. This initial step requires a 2-day reflux in ethanol; it is our hope that the microwave synthesis instrument will allow us to run these reaction at ~140 deg C in order to complete this reaction in under 1 hour.

Dimerization (Cross-linking) of Biological Relevant Phenols.

As noted above, the dimerization (or cross-linking) of lignin monomers results in biologically active lignans. This type of reaction is quite common in many biological environments including tyrosine cross-links in proteins. Phenolic drugs, like acetaminophen, undergo similar reactions leading the adverse side-effects. We are currently exploring the radical intermediates that occur during the cross-linking using ESR spectroscopy and would like to include the dimer in our studies, but these are not commercially available. The approach by Skaff, Jolliffe, and Hutton (J. Org. Chem, 2005, 70, pp. 7353-7363) to synthesize the di and trimers may benefit from the use of microwave technology.