Book of abstracts version 5

Book of abstracts SPOC 2018
Synthesis and purification of bio-based monomers
Author
Keanu Manders
Academy of Technology for Health and Environment
Avans Hogeschool, Breda
University of Maastricht
purification of bio-based monomers
Abstract
The synthesis of bio-based polymers is a growing subject, not only due to their green qualities, but also because they have
better physical characteristics compared to other plastics. With the combination of itaconic acid and a diamine,
Maastricht University, formed a bio-degradable monomer (fig 1.) The possibility to apply variation in the chain length (n)
of the diamine, gives the molecule the ability to form a monomer with great variation of chain lengths. The challenging
part of this research is however the purification of the molecule. When the chain length is varied, the yield of the target
molecule decreases. The objective of this research is finding the most efficient way to synthesize and purify the monomer.
It is expected that when a more efficient method is determined a yield of 85% is possible for t he most difficult chain
lengths [1]. However the presence of chiral centrums in the molecule could complicate the purification. To determine the
purity of the molecule DSC will be used to compare the Tg (˚C), Tm (˚C) and Td (˚C) with previous found results. The
molecule will be synthesized via a Michael addition. Three different diamines (1,4 -diaminobutane; ethylenediamine; 1,5-
diaminopropane) are used as starting reactants. In the presence o f water, itaconic acid will react via the Michael addition
to form the desired monomer [2]. The next step is then to purify the molecule via different methods such as
recrystallization in 50%/50% methanol water; vapor diffusion recrystallization or column chromatography [3].
When the purity is satisfactory a final analysis of the product will happen at Maastricht University via NMR.
Keywords: Bio-based, Bio-degradable monomer, diamines, Michael addition, recrystallization, purification
Table of content
Figure 1: The different target molecules using multiple diamines (1= ethylenediamine (n=2); 2= 1,4 -diaminobutane (n=4);
3=1,5-diaminopropane (n=5)).
Figure 2: The reaction equation of the monomer (1) and the polymerization of the monomer (2); with n for chain length
and m for the number of monomers.
[1] Roy, M., Noordzij, G. J., van den Boomen, Y., Rastogi, S., & Wilsens, C. H. (2018). Renewable (Bis) pyrrolidone Based
Monomers as Components for Thermally Curable and Enzymatically Depolymerizable 2 -Oxazoline Thermoset Resins. ACS
Sustainable Chemistry & Engineering, 6(4), 5053-5066.
[2] Ayadi, F., Mamzed, S., Portella, C., & Dole, P. (2013). Synthesis of bis (pyrrolidone-4-carboxylic acid)-based polyamides
derived from renewable itaconic acid—application as a compatibilizer in biopolymer blends. Polymer journal, 45(7), 766.
[3] "Growing quality crystals," MIT Departement of Chemistry X -ray diffraction Facility, [Online]. Available:
http://web.mit.edu /x-ray/cystallize.html. [Accessed 07 02 2018].
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