Developing New Methods to Produce Bioderived Molecules from Carbohydrates and Biomass
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Authors
Smith, Bailey
Date
Type
thesis
Language
eng
Keyword
Biomass conversion , Furans , Sustainable chemistry
Alternative Title
Abstract
The growth in fossil fuel consumption and greenhouse gas emissions has encouraged the development and implementation of biobased products as replacements for fossil fuel-derived products. Specifically, bioplatform molecules have been identified as versatile molecules that can be produced from biomass, such as wood and algae, and further converted into high-value products. The use of bioplatform molecules is anticipated to provide a renewable alternative for many petroleum-based products, including fuels, specialty chemicals and monomers.
Two widely studied bioplatform molecules are 5-hydroxymethylfurfural (HMF) and 5-chloromethylfurfural (CMF) due to the versatility of their hydroxyl/chlorine, aldehyde and furan ring functionalities that can be utilized for further conversion. However, some challenges have emerged with the use of both molecules. HMF and, to a lesser extent, CMF are easily converted into humins, an unwanted polymeric side-product, during synthesis and storage. Additionally, HMF can be difficult to isolate due to its high polarity, and CMF synthesis methods, unfortunately, use halogenated solvents. With these challenges in mind, this work has investigated alternative routes to produce bioproducts.
A less environmentally harmful CMF synthesis method and using CMF as a substrate were studied. A new method for the production of CMF using a semi-batch flow system was developed, where toluene and cyclopentyl methyl ether were explored as successful alternatives to the chlorinated solvents currently used in obtaining high yields of CMF. To investigate the benefits or drawbacks of CMF compared to HMF, CMF was studied as a substrate in a variety of reactions to produce biofuel precursors and monomers. Improvements in the CMF synthesis method and benefits of its use as a substrate were demonstrated.
Cascade reaction methods were studied for synthesizing select bioproducts from fructose to produce and use HMF in situ without requiring its isolation. The cascade Ritter reaction was the most successful; therefore, its environmental impact was also assessed. Cascade reactions can provide a less environmentally and economically costly route to bioproducts directly from carbohydrates.
This thesis demonstrates methods that have been developed to overcome the challenges encountered using HMF and CMF for bioproduct synthesis, while also establishing successful bioproduct synthesis reactions from both CMF and fructose.
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ProQuest PhD and Master's Theses International Dissemination Agreement
Intellectual Property Guidelines at Queen's University
Copying and Preserving Your Thesis
This publication is made available by the authority of the copyright owner solely for the purpose of private study and research and may not be copied or reproduced except as permitted by the copyright laws without written authority from the copyright owner.