Date of Award
2018
Publisher
North Dakota State University
Document Type
Thesis
Degree Awarded
Master of Science (MS)
Department
Chemistry and Biochemistry
College
Science and Mathematics
Faculty Advisor
Sibi, Mukund P.
Description
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.
Recommended Citation
Wei, Manqing, "Synthesis of Precursors to Non-isocyanate Polyurethanes" (2018). Chemistry and Biochemistry. 42.
https://digitalcommons.ndsu.edu/chem-biochem/42
Rights
NDSU Policy 190.6.2
Rights Link
https://www.ndsu.edu/fileadmin/policy/190.pdf
Author ORCID Identifier
0000-0003-1488-4786
Handle Identifier
https://hdl.handle.net/10365/29167