Biobased diamines are excellent precursors for the synthesis of non-isocyanate polyurethanes (NIPUs). We have prepared several biobased diamines using three different reactions for their synthesis. In the first method, we have carried out chain elongation of cellulose-derived 2,5-diformylfuran by the Henry reaction followed by reduction of the nitroalkene. Yields of the key step: Hantzsch Ester reduction, were 70-80%. Method two involves the Friedel-Crafts alkylation of furfurylamine with different ketones under acidic conditions. Yields of large-scale alkylation reaction were 60-77%. In method three, we combined the Henry reaction and Friedel-Crafts alkylation techniques to access diamines from hemicellulose-derived furfural. These diamines can be reacted with carbonates to access hydroxyalkylcarbamates in good yields, around 80%. We have also developed a novel method for accessing biscarbamates directly from dialdehydes in good yields, 70-94%. The hydroxyalkylcarbamates and biscarbamates are valuable precursors to obtain polyurethanes via the phosgene-free route.
| Identifer | oai:union.ndltd.org:ndsu.edu/oai:library.ndsu.edu:10365/29167 |
| Date | January 2018 |
| Creators | Wei, Manqing |
| Publisher | North Dakota State University |
| Source Sets | North Dakota State University |
| Detected Language | English |
| Type | text/thesis |
| Format | application/pdf |
| Rights | NDSU Policy 190.6.2, https://www.ndsu.edu/fileadmin/policy/190.pdf |
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