Book of abstracts version 5

Book of abstracts SPOC 2018
Biobased Polyesters From Ferulic Acid Derivatives
Author
Robin van den Kieboom
Academy of Technology for Health and Environment
Avans Hogeschool, Breda
Dennis Molendijk, Jack van Schijndel
esters From Ferulic Acid Derivatives
Abstract
The polymer industry is one of the most important chemical industries in the world. Many of the polymers used
worldwide are based from oil. 4% of the global oil- and gas production is used to produce polymers [1]. With the oil
reserves slowly running dry, the demand for biobased polymers is quickly rising. Polyesters synthesized from ferulic acid
could be a possible replacement for the oil-based PET (polyethylene terephthalate). Ferulic acid is a hydroxycinnamic acid
derivative that can be produced from vanillin, a naturally occurring hydroxybenzaldehyde. The aim of this project produce
at least dimers from ferulic acid, using a melt-polycondensation reaction. Secondly, to hydrolyse the polymer back to
monomer, and finally, to re-polymerize the monomer to prove that the polymer can be recycled. FTIR, HPLC, DSC and
HNMR were used to analyse both the polymer and monomer. A yield of at leas t 70% was expected within 3 hours. The
project started with a screening (1/5 of full-scale) to find de fastest catalyst for the polycondensation. The catalysts were
chosen for their use in standard esterfications, and cons isted of various Lewis acids [2] and Bronsted acids. This catalyst
was used in the full-scale polymerisation. 5 mol% catalyst was used in both cases. The polycondensation was executed
under vacuum at 110ºC. The reaction stops when the melting point of the polymer exceeds this temperature. After
analysis the polymer was hydrolysed using 1M NaOH solution, and purified with L/L extraction to retrieve the monomer.
Keywords: Polyester, Ferulic Acid, Biobased Polymer, PET replacement, Polymerisation, Polycondensation, Melt -
Polycondensation, Hydrolysis.
Table of contents
Figure 11: Full reaction equation.
[1] L. Mialon, A. G. Pemba en S. A. Miller, „Biorenewable Polyethylene Terephtalate Minics Derived From Lignin and Acetic Acid,”
Green Chemistry, vol. 12, nr. 10, pp. 1677-1872, 2010.
[2] A. M. B. Santos, M. Martinez en J. A. Mira, „Comparison Study of Lewis Acid Type Catalysts on the Esterification of Octanoic Acid
and n-Octyl Alcohol,” Chem. Eng, Technol., vol. 19, nr. 1, pp. 538 -542 , 1996.
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