DigitalCommons@UMaine Creating Renewable Tunable Polymers from Hydroxymethylfurfural CREATING RENEWABLE TUNABLE POLYMERS FROM HYDROXYMETHYLFURFURAL CREATING RENEWABLE TUNABLE POLYMERS FROM HYDROXYMETHYLFURFURAL
Meredith Allen, Meredith Allen, Meredith Allen, Thomas Schwartz
2013
unpublished
This research addresses the conversion of 5-hydroxymethylfurfural (HMF) into a tunable polymer. HMF is a known cellulose derivative that can be acquired from biomass via hydrolysis of cellulose followed by isomerization and selective dehydration. The process considered here is being developed to create tunable polymers from HMF and involves several different steps, three of which are covered in this thesis. The first step, an etherification, is the reaction of HMF with an alcohol. This step is
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... ignificant because the R-group from the alcohol is added to HMF and the resulting side-chain is carried over to the final polymer giving the polymer unique properties. Thus, by changing the reacting alcohol in the first reaction the final polymer is changed. Upon evaluation of this step various catalysts were tested to identify what active site is needed as well as how the morphology of different catalysts with the previously determined site affect the reactivity. In addition, R-group identity was evaluated to determine if the alcohol used affects the reactivity of the catalyst. For this reaction, it was found that a Brønsted acid active site is needed and that the pore structure of β-Zeolite (BEA) aids the production of an ether product giving both a high production rate and high selectivity for this product. Another important finding is that the identity of the R-group does not greatly affect the amount of ether product produced, suggesting a role of the catalyst in the stabilization of HMF. The second step, not investigated here, is to oxidize the aldehyde group in HMF to create a carboxyl group in its place. The other two reactions investigated involve the hydrogenation of the furan ring followed by a ring-rearrangement which causes the ring to grow to a six-membered lactone, still maintaining the ether branch from the first step. These two processes were first combined to determine if a bifunctional acid-metal catalyst could perform both steps under the same conditions. After it was determined that the conditions would need to be changed between reactions they were performed separately. For both reactions, it was found that bifunctional catalyst consisting of palladium supported on β-Zeolite (Pd /BEA) was effective, and separate reaction conditions were then developed for each step. The final step, not examined here, is a ring-opening transesterification polymerization to form the final polyester product. All three reactions evaluated here were performed individually to evaluate catalysts and reaction conditions. The products of each reaction were analyzed using GC-MS, GC-FID and HPLC.
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