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- Page 6 and 7: PrefaceDear reader,It is our pleasu
- Page 8 and 9: IndexSPOC01Supervised by M.Sc. Nish
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- Page 12 and 13: SYNTHESIS OF 1,2:5,6-DI-ISOPROPYLID
- Page 14 and 15: SYNTHESIS OF T-BUTYL 16-BROMO-4,7,1
- Page 16 and 17: SYNTHESIS LEFT INHIBITORAUTHORSPhou
- Page 18 and 19: SPOC02Supervised by Dr. Kees Kruith
- Page 20 and 21: SYNTHESIS OF AMMONIUM CARBAMATE ASP
- Page 22 and 23: CURCUMIN DERIVATES TO IMPROVELIGHTF
- Page 24 and 25: CURCUMIN DERIVATIVES AS NATURAL RED
- Page 26 and 27: SYNTHESIS AND STABILISATION OF ABIO
- Page 28 and 29: SPOC03Supervised by M.Sc. Betty Oos
- Page 30 and 31: RING OPENING POLYMERISATION (ROP) O
- Page 32 and 33: PHYSICAL AND CHEMICAL PROPERTY-OPTI
- Page 34 and 35: SPOC04Supervised by Dr. Jack van Sc
- Page 36 and 37: Synthesis of Molecular Recyclable S
- Page 38 and 39: APPLICATION OF FLOW CHEMISTRY ON TH
- Page 40 and 41: COMPARING HMTA AND HYDROBENZAMIDEAS
- Page 42 and 43: SPOC05Supervised by M.Sc. Sonny van
- Page 44 and 45: PHTHALIC ANHYDRIDE AND ANALOGUES TO
- Page 46 and 47: A NOVEL APPROACH TO PHTHALICANHYDRI
- Page 48 and 49: CARDANOL-BASED EPOXY COATING BYCROS
- Page 50 and 51: MYCELIUM DERIVED LEATHERAUTHORSElis
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Avans University of Applied Sciences
Lovensdijkstraat 61-63 | 4818 AJ Breda
088 - 525 75 00
PO Box 90.116 4800 Breda
3
Collaborations
4
5
Preface
Dear reader,
It is our pleasure to present you: the Book of Abstracts of the
minor/specialization Polymer and Organic Chemistry (SPOC) 2020
– 2021, offered by the Academy of Technology for Health and
Environment at Avans University of Applied Sciences, Breda.
This book contains abstracts of 22 research projects, which are
currently in the process of being finalized. From the synthesis of
biobased colorants to the search for molecular recyclable plastic
alternatives, these projects hope to expand further research to a
sustainable future.
In the past 20 weeks, each student has worked passionately,
going to great lengths while expanding their knowledge in the
great world that is Polymer and Organic Chemistry. Under the
supervision of great minds, outstanding results have been
obtained.
We, the Book of Abstracts Committee, hope you will enjoy the
read.
Yours sincerely,
Paula Contreras Carballada, Rachel Owusu-Oduro and Mak
Medaric
6
7
Index
SPOC01
Supervised by M.Sc. Nishant Sewgobind
SPOC02
Supervised by Dr. Kees Kruithof
SPOC03
Supervised by M.Sc. Betty Oostenbrink
SPOC04
Supervised by Dr. Jack van Schijndel
SPOC05
Supervised by M.Sc. Sonny van Seeters
SPOC06
Supervised by Dr. Paula Contreras Callada
10
18
28
34
42
52
8
9
SPOC01
Supervised by M.Sc. Nishant V. Sewgobind
Synthesis of 1,2:5,6-di-isopropylidene-A-Dgulofuranose:
A Building Block for a Galectin-3
Inhibitor
Lars Middel and Sjoerd Jansen
Synthesis of t-Butyl 16-bromo-4,7,10,13-
tetraoxahexadecanoate: Spacer for a
Multivalent Galectin Inhibitor
Thomas Nouwt and Chloë Alsemgeest
Synthesis Left Inhibitor
Phoungahn Tran and Gert-Jan Hermans
12
14
16
10
11
SYNTHESIS OF 1,2:5,6-DI-ISOPROPYLIDENE-A-
D-GULOFURANOSE: A BUILDING BLOCK FOR
A GALECTIN-3 INHIBITOR
AUTHORS
Lars Middel and Sjoerd Jansen
SUPERVISOR
M.Sc. Nishant V. Sewgobind
#Inhibitor #Galectin-3 #Proteins #Buildingblock #Sugarchemistry
ABSTRACT
The aim of our research is to synthesize 1,2:5,6-Di-isopropylidene-a-Dgulofuranose,
through a 4-step synthesis (oxidation, acetylation,
hydrogenation and hydrolysis) starting with 1,2:5,6-Di-isopropylidene-Dglucose.
The gulofuranose is a building block for an inhibitor, to block
galectin-3 activity in the human body, because it has been demonstrated,
galectin-3 is involved in cancer, fibrosis and heart disease.
The synthesized products can be readily analysed by FTIR and H-NMR.
Because of the transformation of one functional group in each step,
different signals can be observed. (Alcohol to Ketone, Syn hydrogenation,
etc.) The starting material, intermediates and reagents are given in the
figure below.
Up to now, the acetylation, hydrogenation and hydrolysis were
performed on a test-scale. All the products have been analysed by TLC,
FTIR and H-NMR. All the peaks of the FTIR and H-NMR analysis,
corresponded with the expected signals of the products. Therefore it may
be concluded that all the products have been successfully synthesized.
Given below, are the FTIR and H-NMR spectra of product 5. In these
spectra, the peaks are circled with a colour corresponding to the coloured
circle in the structure of the product.
12
Lars Middel
Sjoerd Jansen
Figure 1: FT-IR spectrum of compound LS-5.1, each signal is marked with a colour to show
which functional group is responsible for the signal.
Figure 2: H-NMR spectrum of compound LS-5.1, the protons and their equivalent signals
marked with colors to distinguish them.
[1] Synthesis of Uridine 5’-[2-S-Pyridyl-3-thio-aaaa-D-galactopyranosyl Diphosphate]: Precursorof
UDP-Thiogal Sugar Nucleotide DonorSubstrate for B-1,4-Galactosyltransferase – Elhalabi, J; Rice,
K.G.
[2] Preparation and properties of the aldohexofuranose pentaacetates – Stevens, J.D.
[3] A convenient approach to an advanced intermediatefor (+)-lactacystin synthesis – Gonda, J.;
Malinak, D.; Kovacova, M.; Martinkova, M.
13
SYNTHESIS OF T-BUTYL 16-BROMO-4,7,10,13-
TETRAOXAHEXADECANOATE: SPACER FOR A
MULTIVALENT GALECTIN INHIBITOR
AUTHORS
Thomas Nouwt and Chloë Alsemgeest
SUPERVISOR
M.Sc. Nishant V. Sewgobind
#Spacer #Hydrobromination #Inhibitor #Anti-Markovnikov #PEG
ABSTRACT
The goal of this research was to create a synthetic procedure for t-butyl
16-bromo-4,7,10,13-tetraoxahexadecanoate, a spacer for a new
multivalent galectin inhibitor. This has been done by using an anti-
Markovnikov hydrobromination on an allylic precursor with HBr/Acetic
acid within a time span of 10 days.
The hypothesis was that the hydrobromination method would produce
multiple side reactions, such as Markovnikov hydrobromination, ether
cleavage [1] and deprotection of the t-butyl ester [2], resulting in a low
yield.
Currently the most promising results come from the synthesis of 1-
(allyloxy)octane, which was used as a test substance to resemble the
original precursor. The analysis of this substance show the expected
signals, therefore it could be used to test the hydrobromination
procedure before using the scarce substrate. This test has so far shown no
successful conversion of an alkene to a bromine group.
The next step is to carry out the hydrobromination with the substrate
while accurately following the protocol. [3]
14
Thomas Nouwt
Chloë Alsemgeest
Figure 1: The figure shown above describes the H-NMR signals of the 1-(allyloxy)octane (CATN
1). The signals correspond to the expected signals of the test substance, a little peak at 2.14
ppm shows some acetone residue.
Figure 2:The three attempts at the test substance are visible in the vials, where CATN 1 and
CATN 2 are 1-(allyloxy)octane and CATN 3 is 1-(allyloxy)hexane.
1] Burwell, R. L. The Cleavage of Ethers. Chem. Rev., 1954, 54 (4), 615-685.
[2] Anderson, G. W.; Callahan, F. M. T-Butyl Esters of Amino Acids and Peptides and Their Use in
Peptide Synthesis 1. J. Am. Chem. Soc., 1960, 82 (13), 3359–3363.
[3] Galli, M. Fletcher, C. J.; del Pozo, M.; Goldup, S. M. Scalable Anti-Markovnikov
Hydrobromination of Aliphatic and Aromatic Olefins. Org. Biomol. Chem., 2016, 14 (24), 5622-
5626.
15
SYNTHESIS LEFT INHIBITOR
AUTHORS
Phounganh Tran and Gert-Jan Hermans
SUPERVISOR
M.Sc. Nishant V. Sewgobind
#Williamsonether #Galactine-3 #Inhibitor #NMR #FTIR #TLC
ABSTRACT
The goal of this research Is to make a linker that can be incorporated into
a galectin 3 inhibitor, by use a semi-finished product with an alcohol
group and making the linker by using a Williamson ether reaction.
The expectation is that by using a Williamson ether reaction, sodium
hydrate and 1,3-dibromopropane the alcohol group turns into an ether
group.
We have done several reactions with the starting product. Thus far it
hasn’t given us the results we were hoping for. So we are now changing
the starting component to hexanol in the hope that we can improve the
reaction condition. So we can optimize the reaction for when the starting
material can be used again with an higher quantity.
16
Phoungah Tran
Gert-Jan Hermans
Figure 1: (Left). FTIR hexanol final
product.
Figure 2: (Below.) FTIR hexanol.
Figure 3: NMR overlay hexanol (blue) en final product (green).
[1] Brouns, F. Saccharide Characteristics and Their Potential Health Effects in Perspective. Frontiers
in nutrition (Lausanne) 2020, 7, 75.
[2] Johannes, L.; Jacob, R.; Leffler, H. Galectins at a glance. Journal of cell science 2018, 131,
jcs208884
[3] Modenutti, C. P.; Capurro, J. I. B.; Di Lella, S.; Martí, M. A. The Structural Biology of Galectin-
Ligand Recognition: Current Advances in Modeling Tools, Protein Engineering, and Inhibitor
Design. Front. Chem. 2019, 7.
[4] de Jong, Charlotte G H M; Gabius, H.; Baron, W. The emerging role of galectins in
(re)myelination and its potential for developing new approaches to treat multiple sclerosis. Cellular
and molecular life sciences : CMLS 2019, 77, 1289-1317.
17
SPOC02
Supervised by Dr. Kees Kruithof
Synthesis of Ammonium Carbamate as
Precursor for Urea
Bart de Jonge and Thijmen Willems
Curcumin Derivates to Improve Lightfastness
And Stability of the Natural Dye
Mischa Fraanje and Daan Welschen
Curcumin Derivatives as Natural Red Colorant
for Bioplastic Packaging Applications
Rachel Owusu-Oduro and Raiko Moerenhout
Curcumin Derivatives as Natural Red Colorant
for Bioplastic Packaging Applications
Byren Teuben en Christiaan Verdonk
20
22
24
26
18
19
SYNTHESIS OF AMMONIUM CARBAMATE AS
PRECURSOR FOR UREA
AUTHORS
Bart de Jonge and Thijmen Willems
SUPERVISOR
Dr. Kees Kruithof
#Ammoniumcarbamate #CirlcularFertilzer #MildConditions #Urea
ABSTRACT
The emission of nitrous gasses and carbon dioxide have a significant
contribution on climate change. The amount of production of these
greenhouse gasses can be reduced by creating a solid product out of
them. Ammonium carbamate can be a solution to this problem because it
can be produced using ammonia gas and carbon dioxide gas. Ammonium
carbamate is used in the production of urea, which is a commonly used
fertilizer. In this research several methods were used to make ammonium
carbamate. This was executed with both of the reactants in a gas form.
The reaction took place in a non-solvent to make it precipitate. A method
with a liquid form of ammonia was also used and reacted with solid
carbon dioxide. The advantage of the second method is the absence of
non-solvents. This would benefit the amount of waste. That method
unfortunately needs extreme low temperatures to make ammonia in a
liquid form and carbon dioxide in a solid form. The ammonium carbamate
was analyzed using H-NMR and FT-IR. Urea can be formed with the
ammonium carbamate with extreme high pressure and high
temperatures. The identification of urea also concludes if carbamate was
produced.
20
Bart de Jonge
Thijmen Willems
Figure 1: FT-IR spectra of the ammonium carbamate synthesis with gasious NH 3 /CO 2 in 100%
ethanol
Figure 2: The parr reactor
used for urea synthesis.
Figure 3: The reaction set up used for the gaseous NH 2 /
CO 2 synthesis
[1] F. Barzagli, „From greenhouse gas to feedstock: formation of ammonium carbamate from CO 2
and NH 3 in organic solvents and its catalytic conversion into urea under mild conditions,” Green
Chemistry, 2011.
[2] A. Brooks, „AMMONIUM CARBAMATE,” Inorganic Syntheses, 1946.
[3] K. O. Yoro, „CO2 emission sources, greenhouse gases, and the global warming effect,”Advances
in Carbon Capture, pp. 3-22, 2020.
21
CURCUMIN DERIVATES TO IMPROVE
LIGHTFASTNESS AND STABILITY OF THE
NATURAL DYE
AUTHORS
Mischa Fraanje and Daan Welschen
SUPERVISOR
Dr. Kees Kruithof
#Curcumin #Lightstability #Lightfastness #Renewable #NaturalDye
ABSTRACT
Avans is currently doing research on the use of curcumin as a dye in food
and bioplastics. The focus in this research is to improve stability against
photo-oxidation. Curcumin’s color can fade by exposure to light. To solve
this problem, research is being carried out to synthesize derivatives of
curcumin with a protective grouped linked to the CH 2 .
In this project, the goal is to synthesise 1 gram of curcumin derivative with
a higher light fastness than curcumin. It is expected that this derivative
has a longer conjugated system which provides a more stable molecule
with enhanced light fastness features.
The products are teste for photo-oxidation resistance and coloring.
Products are analysed using FTIR, TLC, H-NMR and light exposure test. In
this project, literature research by Kamal et. al. is being repeated to find
out if the reactions done are also suitable to be used with curcumin [1].
Another article by Sahu et. al. was reproduced to find whether curcumin
derivatives in a reaction with benzaldehyde gives a better stability [2].
Currently, derivatives have been made using phenylacetaldehyde and
dimethyl acetal, as pre-research on the curcumin derivatives. However,
conversion of the reaction was low and with multiple by-products. Further
research needs to be conducted to find a suitable way to functionalize the
CH 2 group of curcumin.
22
Mischa Fraanje
Daan Welschen
Figure 1: Reaction [1] with
dimethyl acetal.
Figure 2: Reaction with curcumin and benzaldehyde [2].
Figure 3: NMR spectrum curcumin
(top), Product synthesis (middle) en
reference literature (bottom).
[1] Kamal, A.; Sastry, K. N. V.; Chandrasekhar, D.; Mani, G. S.; Adiyala, P. R.; Nanubolu, J. B.;
Singarapu, K. K.; Maurya, R. A. One-Pot, Three-Component Approach to the Synthesis of 3,4,5-
Trisubstituted Pyrazoles. Journal of organic chemistry 1900, 80, 9-24
[2]Sahu, P. K.; Sahu, P. K.; Gupta, S. K.; Thavaselvam, D.; Agarwal, D. D. Synthesis and evaluation
of antimicrobial activity of 4H-pyrimido[2,1-b]benzothiazole, pyrazole and benzylidene derivatives
of curcumin. European journal of medicinal chemistry 2012, 54, 366-378
23
CURCUMIN DERIVATIVES AS NATURAL RED
COLORANT FOR BIOPLASTIC PACKAGING
APPLICATIONS
AUTHORS
Rachel Owusu-Oduro and Raiko Moerenhout
SUPERVISOR
Dr. Kees Kruithof
#Curcumin #Lightstability #Lightfastness #Renewable #NaturalDye
ABSTRACT
The Centre of Expertise Biobased Economy is currently researching how to
use curcumin as a colorant for food and bioplastics with improved stability
towards photo-oxidation. Studies have shown that complexation to zinc
improves lightfastness. A red substance was formed during
recrystallization of the zinc complex with DMF. Literature proves that zinc
complexes can coordinate with DMF. However, DMF is harmful to the
environment. Therefore, this research is conducted to find an alternative
to DMF. In addition, the molecule will be fully characterized, and the
lightfastness will be tested. A methanol reflux setup was used to
synthesize the zinc complex from Zn(AC) 2 and diacetylcurcumin (DAC).
Recrystallization with DMF followed. For the alternative solvent, 1-
formylpyrrolidine was used. This resulted in a red coloured powder. This
powder was characterized by 1 H-NMR, FT-IR, UV-VIS.
24
Rachel Owusu-Oduro
Raiko Moerenhout
Figure 2: Zn-(DAC)-DMF and Zn-(DAC)-1-formylpyrroline.
Figure 1: Reflux reaction to form Zn-(DAC) complex.
Figure 3: Reflux reaction to form Zn-(DAC) complex.
Figure 4: Zn-(DAC) complex.
1. W. Meza-Morales et al, „Full Structural Characterization of Homoleptic Complexes of
Diacetylcurcumin with Mg, Zn, Cu, and Mn: Cisplatin-level Cytotoxity in Vitro with Minimal Acute
Toxitiy in Vivo,” Molecules, vol. 24, nr. 1598, pp. 1-18, 2019.
2. E. Wouters, “Develoment of a photostability curcumin derivate and the study of the degradation
behaviour in bio polimers.,” Avans Universaty , Breda, 2020.
25
SYNTHESIS AND STABILISATION OF A
BIODEGRADABLE COLORANT BASED OF
CURCUMIN
AUTHORS
Byren Teuben and Christiaan Verdonk
SUPERVISOR
Dr. Kees Kruithof
#Curcumin #Rubrocurcumin #AlphaHydroxyAcid #UV-stability
ABSTRACT
Curcumin is an herb used in many Asian recipes and is recognised by its
bright orange colour. It´s also known for its beneficial effect health and
therefore an important ingredient in many cosmetics. In this study the
attention is focussed at colourants based on curcumin. Colourants are
molecules that interfere with the UV-spectrum and therefore have a
certain colour. The aim of this research is to synthesize at least 3 grams of
the rubrocurcumin derivatives: CBS, CBP OR CBIP, CBF and CBM. The
prepared molecules will be determined by TLC, FTIR, TGA, HPLC and NMR,
for purity and conversion rate. For this project curcumin, boric acid and an
alpha hydroxyacid will be solved in a ratio 1:1:1. The solvent is toluene
and this will be stirred in a setup with an Dean stark trap at 110°C. the
tested alpha hydroxy acids are: oxalic acid, salicylic acid, phthalic acid and
phenyl malonicacid. The reaction gives us a product of rubrocurcumin
with still a lot of curcumin inside, what makes it hard to analyse. Also, a
lot of solvents, like methanol and acetonitril will break down the product
to its starting materials.
Figure 1: Formed products.
26
Byren Teuben
Christiaan Verdonk
Figure 2: Reaction of curcumin to rubrocurcumin.
Figure 3: The spectra above is an LC-MS spectra taken of the CBS product. CBS was
synthesized by reacting curcumin with boric acid and salicylic acid. In the spectra we can see
multiple peaks which are derived from the reactants, intermediates, products and
degradation products their molecular masses.
Te first mass peak we are going to talk about is the peak around 369. This peak is caused by
left-over curcumin. A mass peak of 370 is also visible and is due to the carbon 13 isotope. This
will also occur in other signals. Then there is a mass peak around 515. This peak is from the
CBS product. This peak has 2 sidepeaks caused by the isotopes.
Finally we have a mass peak at 177 and 245. These peaks indicate the degradation products
of curcumin.
[1] S. D. R. a. B. S. N. JEENA JOHN, “Kinetic Analysis of Thermal and Hydrolytic Decomposition of
Spiroborate Ester of Curcumin with Salicylic Acid”.
[2] S. D. R. B. S. JEENA JOHN, “KINETIC ANALYSIS OF THERMAL DECOMPOSITION OF
RUBROCURCUMIN”.
[3] J. J. •. R. S. D. •. S. B. •. K. V. D. Babu2, “Synthesis, spectral characterization and thermal
analysis of rubrocurcumin and its analogues”.
27
SPOC03
Supervised by M.Sc. Betty Oostenbrink
Ring Opening Polymerisation (ROP) of
Valerolactone
Bas Klijn and Jonne de Vries
Physical and Chemical Property-Optimalisation
of Poly(ethylene succinate)
Joris Adank and Amy van Gestel
30
32
28
29
RING OPENING POLYMERISATION (ROP) OF
VALEROLACTONE
AUTHORS
Bas Klijn and Jonne de Vries
SUPERVISOR
M.Sc. Betty Oostenbrink
#RingOpeningPolymerisation #Biopolymerchemistry #TuCatalyst
ABSTRACT
The goal of our research was to create a biopolymer practicum that can
be used in de specialisation of organic chemistry, where a Ring Opening
was used to polymerise a monomer. In the reaction, gamma-Valero
lactone is used as monomer, a thiourea complex was used as catalyst for
the monomer and DBU was used as catalyst for the initiator 2-naphtol.
During the reaction, the conversion was determined with a H-NMR
analysis. When the reaction was stopped, the degree of polymerisation
was also determined with the H-NMR. A GPC analysis was done to
confirm the degree of polymerisation. To start the polymerisation, N-
Cyclohexyl-N'-(3,5-bis(trifluoromethyl)phenyl)thiourea (TU) was used as a
catalyst. TU was synthesised due to the high commercial price.
The TU catalyst was synthesized according to the article from C. B.
Tripathi and S. Mukherjee [1] after 2 hours, it was expected that 88%
conversion was obtained. In our reaction, we obtained 85% conversion.
With the synthesised TU as catalyst, the gamma-Valero lactone was
polymerised according to the article from B. G. G. Lohmeijer et al. After 3
hours it was expected that a new peak was formed around 3.26 ppm in
the H-NMR spectrum.
30
Bas Klijn
Jonne de Vries
Figure 1: Reaction scheme of polymerisation.
Figure 2: N-[3,5-bis(trifluoromethyl)phenyl]-N-clyclohexyl catalyst product
[1] C. B. Tripathi and S. Mukherjee, “Lewis Base Catalysis by Thiourea: N-Bromosuccinimide-
Mediated Oxidation of Alcohols,” doi: 10.1021/jo202269p.
[2] B. G. G. Lohmeijer et al., “Guanidine and Amidine Organocatalysts for Ring-Opening
Polymerization of Cyclic Esters,” doi: 10.1021/ma0619381.
31
PHYSICAL AND CHEMICAL PROPERTY-
OPTIMALISATION OF POLY(ETHYLENE
SUCCINATE)
AUTHORS
Joris Adank and Amy van Gestel
SUPERVISOR
M.Sc Betty Oostenbrink
#Polyester #Properties #Polymerization #Cuccinate #PES
ABSTRACT
Poly(ethylene succinate) (PES) is a derivative of the widely used PBS.
Instead, butanediol was replaced with ethylene glycol in order to obtain
PES. In this research the main goal was to determine the chemical and
physical properties of PES. This polyester was obtained by polyesterification
of ethylene glycol and succinic anhydride. The reaction was
performed under the catalysation of Titanium(IV)isopropoxide.
Two setups have been used throughout the research:
– Dean-Stark-conditions with tert-butylbenzene as reflux-liquid (170 ºC)
(24h)
– Overhead stirrer in plain reactants with increasing temperatures up to
170 ºC (6h
With the help of differential scanning calorimetry (DSC) an indication of
the chain length was determined. According to the findings of Zhang’s
research a molar weight of 87 kg/mol showed a glass transition
temperature of -8.9 ºC. With that knowledge the goal was to strive for
this result in order to obtain this desired chain length.
In order to determine physical properties, the chain length had to be
maximised, or else the results could have been affected.
32
Joris Adank
Amy van Gestel
Figure 1: PES synthesiZed under Dean-Stark conditions on the reflux of tert-butylbenzene
(170 ºC), catalysed by Titanium(IV)isopropoxide. Glass transition temperature at -10.0 ºC.
Figure 2: PES right after solidifying
from the liquid phase.
Figure 3: PES after some time
(crystallised).
[1] K. Zhang en Z. Qiu, „Effect of methyl as the simplest C–H side group on the significant variation
of physical properties of biodegradable poly(ethylene succinate),” Polymer Testing, nr. 90, p. 7,
33
SPOC04
Supervised by Dr. Jack van Schijndel
Synthesis of Molecular Recyclable Semi-
Aromatic Poly-Dihydro-Isosulfiric Acid
Mak Medaric and Jesper van der Vorm
Application of Flow Chemistry On The Green
Knoevenagel Condensation to Cinnamic Acid
Derivatives
Moctar Coulibaly and Dries Maessen
Comparing HMTA and Hydrobenzamide as
Catalysts at the Preparation of Styrene-Analog
from Ferulinacid
Kevin Smits and Kevin van Luijk
34
36
38
34
35
Synthesis of Molecular Recyclable Semi-
Aromatic Poly-Dihydro-Isosulfiric Acid
Authors
Mak Medaric and Jesper van der Vorm
Supervisor
Dr. Jack van Schijndel
#GreenChemistry #Green Knoevenagel #MolecularRecycling #PET
ABSTRACT
Jack van Schijndel et al. have showed that a molecular recyclable polyester
could be synthesized from vanillin. This polymer, however, was highly
crystalline which limited its possible uses, mainly in providing a possible
alternative to polyethylene terephthalate (PET). The goal of this research
was to synthesize poly-dihydro-isoferulic acid from iso-vanillin expecting an
increase in amorphicity due to the meta-substituted ring, resulting in less
linear polymer chains. At first, several Green Knoevenagel Condensation
reactions were performed to synthesize iso-ferulic acid from iso-vanillin. In
this first step, water proved to be a suitable alternative solvent to ethyl
acetate. Although there were mixed results in terms of yield, high purity
product was eventually obtained. The newly created double bond in isoferulic
acid was then hydrogenated to prevent conjugation within the
molecule, promoting the molecular recyclability of the final polyester. The
third step was acetylating the phenolic group to prevent sublimation
during polymerization. At last, the acetylated-dihydro-isoferulic acid was
polymerised in two steps. The first step involved adding caustic soda and
heating the mixture for three hours after which a Solvent Assisted
Polymerization was performed using o-xylene and refluxing for another 3
hours. Samples of each step were taken and analysed by determining its
melting point, H-NMR & FTIR spectroscopy. Reactions were followed by
TLC. The end polymer and its intermediate samples will be analysed by
GPC and HPLC. Physical properties will be characterized by DSC analysis.
36
Mak Medaric
Jesper van der Vorm
Figure 1: Reaction scheme.
Figure 2: HNMR spectrum of isoferulic acid.
Figure 3: HNMR spectrum dihydro-isoferulic acid.
[1] J. A. M. v. Schijndel, Exploring the Sustainable Production of Biobased Building Blocks for
Chemically Recyclable Aromatic Polymers, Eindhoven, Noord-Brabant: Technische Universiteit
Eindhoven, 2020.
[2] J. A. M. v. Schijndel, D. Molendijk, H. Spakman, E. Knaven, L. A. Canalle en J. Meuldijk
“Mechanistic Considerations and Characterization of Ammonia-Based Catalytic Active
Intermediates of the Green Knoevenagel reaction of Various Benzaldehydes,” Green Chemistry
Letters and Reviews, pp. 323-331, 2019
37
Figure 4: FTIR isoferulic acid.
APPLICATION OF FLOW CHEMISTRY ON THE
GREEN KNOEVENAGEL CONDENSATION TO
CINNAMIC ACID DERIVATIVES
AUTHORS
Moctar Coulibaly and Dries Maessen
SUPERVISOR
Dr. Jack van Schijndel
#FlowChemistry #GreenKnoevennagelCondensation #CinnamicAcid
ABSTRACT
Flow chemistry is an alternative way of synthesising chemicals by replacing
a batch reactor for a capillary tube with a continues flow of reagents. This
way of synthesis is safer, faster and better scalable than a usual batch
reactor setup. The aim of this project is to compose a protocol for
performing the green Knoevenagel condensation to synthesise different
cinnamic acid derivatives.
The setup used in this project consists of multiple lengths of PTFE tubing
arranged in such a way that both the reagents combine in a single tube
witch spirals down in a hot water/glycerol bath. Two syringes are used to
propel the reagents into the system, these syringes are not driven by a
syringe pump but rather by manually turning a screw.
The research shows that the reactions do take place in a flow
environment. However, the yield of the various products remains rather
low. Using 2-amino ethanol not only as catalyst but also as solvent,
instead of water, proved to be favourable for a higher yield.
38
Moctar Coulibaly
Dries Maessen
Figure 1: Flow setup.
Figure 2: Product of second attempt,
Ferulic acid with Rf = 0,06.
Figure 3: HPLC-chromatogram of Ferulic acid product of attempt 5 at 300nm (70/30%
acetonitrile/1% acetic acid).
1] van Schijndel, J., Canalle, L. A., Molendijk, D., & Meuldijk, J. (2017). The green Knoevenagel
condensation: solvent-free condensation of benzaldehydes. Green Chemistry Letters and Reviews,
10(4), 404–411. https://doi.org/10.1080/17518253.2017.1391881.
[2] van Beurden, K., de Koning, S., Molendijk, D., & van Schijndel, J. (2020). The Knoevenagel
reaction: a review of the unfinished treasure map to forming carbon–carbon bonds. Green
Chemistry Letters and Reviews, 13(4), 349–364. https://doi.org/10.1080/17518253.2020.1851398.
39
COMPARING HMTA AND HYDROBENZAMIDE
AS CATALYSTS AT THE PREPARATION OF
STYRENE-ANALOG FROM FERULINACID
AUTHORS
Kevin Smits and Kevin van Luijk
SUPERVISOR
Dr. Jack van Schijndel
#Ferulinacid #Green #Knoevenagel #HMTA #Hydrobenzamide
ABSTRACT
For the past 17 years at least, humanity has mined oil from the ground, it
was only a dozen years ago that we started to realize the downsides.
In order to abandon this concept we have to look further then just
electric cars and solar panels. We have to be able to replace every aspect
of the crude oil in order to be able to stop mining it. Hence this research;
to replace the most used polymer of all-time polystyrene, which is
synthesized from crude oil parts.
In order to replace polystyrene we need to have a new styrene molecule
that can be synthesized from molecules that exist in plants, trees or even
animals. We need a biobased styrene molecule.
Jack van Schijndel et al., 2020 has introduced a green variant of the
Knoevenagel Condensation, in which there is no longer need of Pyridine.
He has also synthesized different kind of biobased styrene’s.
This research is purely focused on the preparation of a styrene analog
through Ferulinacid.
In order to successfully polymerize this styrene analog, the Ferulinacid first
had to be decarboxylated and then acetylated.
The decarboxylation was executed using a catalyst. Both HMTA and
Hydrobenzamide were suitable because of the tertiary nitrogen atom.
Both were tried in order to properly compare these two catalysts. HMTA
had a better yield and a much lower reaction time.
After the preparations, the styrene analog was successfully polymerized.
40
Kevin Smits
Kevin van Luijk
Figure 1: Chromatogram GPC-analysis polymer.
Figure 2: GPC intergation.
Figure 4: HMTA crystals.
Figure 5: Styrene analog.
41
Figure 3: FTIR hydrobenzamide.
[1] Jack van Schijndel, “Exploring the sustainable production of biobased building blocks for
chemically recyclable aromatic polymers,” 2020.
[2] J. van Schijndel, D. Molendijk, K. van Beurden, L. A. Canalle, T. Noël, and J. Meuldijk,
“Preparation of bio-based styrene alternatives and their free radical polymerization,” Eur. Polym. J.,
vol. 125, p. 109534, 2020, doi: 10.1016/j.eurpolymj.2020.109534.
[3] J. van Schijndel, D. Molendijk, H. Spakman, E. Knaven, L. A. Canalle, and J. Meuldijk,
“Mechanistic considerations and characterization of ammonia-based catalytic active intermediates
of the green Knoevenagel reaction of various benzaldehydes*,” Green Chem. Lett. Rev., vol. 12,
no. 3, pp. 323–331, 2019, doi: 10.1080/17518253.2019.1643931.
SPOC05
Supervised by M.Sc. Sonny van Seeters
Phthalic Anhydride and Analogues to Polyesters
Tessa Lokate and Babette Fens
A Novel Approach to Phthalic Anhydride and
Analogues in Unsaturated Polyester Resins
Steven Tibosch and Jesper van der Welle
Cardanol-Based Epoxy Coating by Crosslinking
with Phthalic Anhydride
Curtis Ham and Tirza Huijboom
Mycelium Derived Leather
Elisia Hoek and Robin Bouman
44
46
48
50
42
43
PHTHALIC ANHYDRIDE AND ANALOGUES TO
POLYESTERS
AUTHORS
Tessa Lokate and Babette Fens
SUPERVISOR
M.Sc. Sonny van Seeters (Client: Arnold Nijhuis)
#Coatings #Polyesters #Analogue #Conversion #Transesterification
ABSTRACT
The aim of this project was to synthesize a linear polyester as a resin for
coatings using phthalic anhydride (PA) as a reference monomer and 1,4-
butanediol. Three analogues from seaweed were used to compare and
replace the PA. The properties of powder coatings are low molecular
weight (Mn ~2-6 kg/mol), are thermally stable, and have an amorphous
polymeric Tg of 45 °C. To make the polymers, transesterification
polycondensation reactions were performed with the diol, one of the
monomers, and titanium tetra-isopropoxide (2:1:0.033). The reaction was
done under 180 °C first under inert conditions and after one hour under
vacuum. H-NMR was used to determine the conversion during the
reaction as shown in figure 1. GPC and DSC were used to measure the
molecular weight and thermally properties. FTIR was used for
characterization. The analysis technics showed that the polymers were
formed, and a conversion between 20-80% was measured when the
reaction was optimized. The chains of the formed polymers were very
short, to the extent that the product didn’t precipitate appropriately. This
was also confirmed with the GPC analyses that gave low molecular
weight. The experiments show that the analogues can replace PA in the
synthesis of resins for a powder coating.
44
Tessa Lokate
Babette Fens
Calculated Conversion of Polymer
OH*2 (2pr): 3,37/2 =1,685 (black signal)
CH2*2 (4pr): 17,4/4 =4,425 (green signal)
1,685/4,425 = 0,381
0,381 × 100% = 38,09%
100 – 38,09 = 61,9%
Conversion is 62%
Figure 1: H-NMR spectrum of the polymer made from one of the analogues and 1.4-
butanediol to calculate the conversion
[1] A. Nijhuis, "Centre of Expertise Biobased Economy," CoE BBE, Januari 2020. [Online]. Available:
https://www.coebbe.nl/projecten/zcore-van-zeewier-naar-coating-resin-applicaties/. [Accessed 15
Februari 2021].
[2] E. Gubbels, J. P. Drijfhout, C. Posthuma-van Tent, L. Jasinska-Walc, B. A. Noordover and C. E.
Koning, "Bio-based semi-aromatic polyesters for coating applications," Organic Coatings, vol. 2014,
no. 77, pp. 277-284, 2013.
[3] Y. Tachibana, M. Yamahata and K. Kasuya, "Synthesis and characterization of a renewable
polyester containing oxabicyclic dicarboxylate derived from furfural," in Green Chemistry,
RSCPublishing, 2013.
45
A NOVEL APPROACH TO PHTHALIC
ANHYDRIDE AND ANALOGUES IN
UNSATURATED POLYESTER RESINS
AUTHORS
Steven Tibosch and Jasper van der Welle
SUPERVISOR
M.Sc. Sonny van Seeters
#PhthalicAnhydride #Unsaturated polyesters #Greenchemistry
ABSTRACT
Unsaturated polyester resins (UPRs) have many valuable properties, such
as excellent water repellency, resistance to chemicals and much more. In
this study, a UPR will be synthesized with maleic anhydride (MA),
propylene glycol (PG), and phthalic anhydride (PA) to be further
crosslinked with styrene. The UPR’s properties are determined by
differential scanning calorimetry (DSC), gel permeation chromatography
(GPC), and thermogravimetric analysis (TGA). Mechanical properties will
be analyzed by measuring Young’s modulus and elongation at break.
Multiple biobased analogues of phthalic anhydride will be used to make
UPR’s as well, to investigate whether these analogues are suitable
replacements for phthalic anhydride in unsaturated polyester resins. The
analogues used are H2-F/MA-DA-Adduct and H2-MF/MA-DA-Adduct, both
supplied by TNO. These analogues have proven to be less harmful than
phthalic anhydride, which is another reason why phthalic anhydride has
to be replaced. At the moment of submission of this abstract, not all data
is present. It is expected that the H2-F and H2-MF analogues will both
increase the glass-rubber transition temperature (Tg) and the average
molecular weight of their respective UPRs. The influence of the PA
analogues on the mechanical properties of their respective UPRs is still
unclear. Overall, this study will show the effects of phthalic anhydride
analogues on the unsaturated polyester resins and whether these
analogues are a suitable replacement for phthalic anhydride.
46
Steven Tibosch Jasper van der Welle
Figure 1: Maleic Anhydride, Phthalic Anhydride and Propylene glycol react to create an
unsaturated polyester.
Figure 2: The synthesized unsaturated polyester to be crosslinked with styrene.
Figure 3: The final product, an unsaturated polyester resin.
[1] B. Cherian en E. T. Tchachil, „Synthesis of Unsaturated Polyester Resin—Effect of Sequence of
Addition of Reactants,” Polymer-Plastics Technology and Engineering, vol. 44, nr. 5, pp. 931-938,
2005.
[2] A. A. Athawale en J. A. Pandit, „Unsaturated Polyester Resins, Blends, Interpenetrating Polymer
Networks, Composites, and Nanocomposites: State of the Art and New Challenges,” in
Unsaturated Polyester Resins, 2019, pp. 1-42.
[3] J. K. Fink, „Unsaturated Polyester Resins,” in Reactive Polymers Fundmentals and Applications,
2005, pp. 1-67.
47
CARDANOL-BASED EPOXY COATING BY
CROSSLINKING WITH PHTHALIC ANHYDRIDE
AUTHORS
Curtis Ham and Tirza Huijboom
SUPERVISOR
M.Sc. Sonny van Seeters
#Cardanol #Crosslink #Anhydride #Epoxy #Coating
ABSTRACT
Cardanol is retrieved from cashew nutshell liquid, and due to its molecular
structure capable of being epoxidized. With this epoxidized cardanol it is
possible to crosslink multiple molecules of epoxidized cardanol together
to form a polymer. In previous research a cardanol coating was created
using amine-based crosslinking agents, which are harmful for the
environment. This study resulted in cardanol coating with a Tg of 24°C. In
this study phthalic anhydride was used as a less harmful alternative with
the goal of later replacing phthalic anhydride with biobased alternatives.
A goal of this study was to make a cardanol epoxy coating with a higher
Tg, this has not yet been achieved. The crosslinking reaction performed in
this study has been optimized, the optimal temperature for the reaction is
180 °C. At this temperature the crosslinking rate is the highest. So far, the
Tg of the products has been around -20 °C. To improve this the reaction
time at 180 °C will be increased. The expectation is that this will increase
the crosslinking of the cardanol, and therefore will increase the Tg of the
product.
48
Curtis Ham
Tirza Huijboom
Figure 1: Reaction [1] with dimethyl acetal.
Figure 2: Crosslink reaction of epoxidized cardanol and phthalic anhydride with EMI as
catalyst.
49
Figure 3: Cardanol based
epoxy coating with Tg = 20°C.
[1] A.-S. Mora, M. Deconstanzi, G. David and S. Caillol, “Cardanol-Based Epoxy Monomers for High
Thermal Properties Thermosets,” European Journal of Lipid Science and Technology, vol. 121, pp. 1-
8, 2019.
[2] M. Muusz, “Biobased Epoxy Resin,” Avans Hogeschool, Breda, 2021.
MYCELIUM DERIVED LEATHER
AUTHORS
Elisia Hoek and Robin Bouman
SUPERVISOR
M.Sc. Sonny van Seeters
#Veganleather #Chitosan #Mycelium #Crosslinking
ABSTRACT
The aim of this study is to create a method to make a leather like material
out of mycelium by optimizing the crosslinking on chitosan (the active
part of mycelium).
This will be achieved by comparing the different crosslinkers vanillin, citric
acid and dialdehyde starch to one another. Analysis are TGA for thermal
properties, FTIR for structural analysis and Bradford essay for crosslinking
index.
This crosslinking method was first performed by taking pure chitosan and
dissolving in 2% acetic acid solution and after 10 minutes adding an
appropriate amount of crosslinking agent. The results of this are not yet
complete however the results shown so far prove that crosslinking took
place. The FTIR spectra shows the addition of the crosslinking agent
within the structure and the physical feel of the product is a stronger
material.
The same process was then repeated with mycelium itself under the same
conditions. Mycelium is a mushroom fungi so it already has fibers within
itself and with the addition of the crosslinking agent the hold of the fibers
is much stronger.
50
Elisia Hoek
Robin Bouman
Crosslinking agent
Mycelium
Figure 1: The set up for the
experiment. To 2% acetic acid,
chitosan was added along with a
crosslinker as citric acid, vanillin and
dialdehyde starch (DAS). The DAS
was synthesised before crosslinking.
Mycelium
Figure 2: An
example of
the product
(with
chitosan).
Figure 3: The FTIR of the products.
[1]K. W.-D. 1, „Crosslinking of Chitosan with Dialdehyde Chitosan as a New Approach for
Biomedical Applications,” Materials, 2019
[2]Mycoworks, „ISO/IEC 17025 Certified third party test report,” Vartest, San Francisco, CA, 2020.
51
SPOC06
Supervised by Dr. Paula Contreras Carballada
The Synthesis of Dopal from Dopamine and
Dopac
Anniek Willaert and Britt Vijverberg
In Search for the Dry Fluoride Source
Roel Kerkers and Norbert Mulkens
A Safer Syntheses Of Anti-Cancer Agent Fk866
Steyn Van Gerwen and Bas Schoone
54
56
58
52
53
THE SYNTHESIS OF DOPAL FROM DOPAMINE
AND DOPAC
AUTHORS
Anniek Willaert and Britt Vijverberg
SUPERVISOR
Dr. Paula Contreras Carballada
#DOPAL #Dopamine #DOPAC #PotassiumPermanganate #DIBAL-H
ABSTRACT
Addictive substances such as nicotine from tobacco, alcohol, and drugs
affect the dopamine system in the brain. Dopamine is a neurotransmitter
in the brain responsible for the reward system. Long-term use of addictive
substances can cause physical changes in the brain. From the RIVM, a new
animal model based on zebrafish in the embryonic state is used. This
model shows that the behavior of these fish changes significantly based
on the present concentration of Harman. To set up a suitable analysis
method for the concentration of dopamine in the brain, the RIVM needs
the metabolite of the transition from dopamine to DOPAC. This is mainly
DOPAL. DOPAL is commercially very difficult to obtain and thereby
expensive.
Therefore, the goal is to synthesize DOPAL from the neurotransmitter
dopamine and its metabolite DOPAC using potassium permanganate
(oxidation) and DIBALH (reduction). It is expected that 1 gram of DOPAL
will be synthesized with a yield between 10 and 15%. The FT-IR and 1H
NMR analyses will show characteristic aldehyde signals; at the FT-IR
spectrum, it will be seen at 1740-1720 cm-1, and the NMR spectrum will
show the signal at 9.7 ppm.
So far, DOPAL has probably been synthesized twice, both times in the
oxidation reactions. Characterization of these products showed a clear
aldehyde peak around 9.7 ppm.
54
Anniek Willaert
Britt Vijverberg
Figure 1: The 1H-NMR spectrum of 3,4-diphenylacetic acid methyl ester. This is the product
after the second step in the reduction reaction. Hereby is the most important chemical shift
the multiplet at 3,7 ppm from the ester group.
Figure 2: The 1H-NMR spectrum of DOPAL with THP (protecting group). Hereby is the most
important chemical shift the triplet at 9,8 ppm from the aldehyde group. This product is
synthesized from the oxidation of dopamine.
[1] D. C. Barman, P. Saikia, D. Prajapati en J. S. Sandhu, „Heteregeneous permanganate oxidations.
A novel method for the deamination using solid supported iron-permanganate,” Synthetic
Communications, vol. 32, nr. 22, pp. 3407-3412, 2002.
[2] J. Narayanan, Y. Hayakawa, J. Fan en K. L. Kirk, „Convenient syntheses of biogenic aldehydes,
3,4-dihydroxyphenylacetaldehyde and 3,4-dihydroxyphenylglycolaldehyde,” Bioorganic chemistry,
vol. 31, pp. 191-197, 2003.
[3] D. J. Nutt, A. Lingford-Hughes, D. Erritzoe en P. R. Stokes, „The dopmaine theory of addiction:
40 years of highs and lows,” Nature Reviews: Neuroscience, vol. 16, nr. 5, pp. 305-312, 2015.
55
IN SEARCH FOR THE DRY FLUORIDE SOURCE
AUTHORS
Roel Kerkers and Norbert Mulkens
SUPERVISOR
Dr. Paula Contreras Carballada
#Beta-Lactam #Penicillin #Antibiotics #Cyclization #Fluoride
ABSTRACT
Antibiotics are common medicines that are used to treat or prevent
bacterial infections within the human body. Antimicrobial resistance is a
serious threat that is no longer a prediction for the future but happening
right now in every region of the world. In this research, a general
synthesis method towards the beta-lactam functional group present in
penicillins is explored via three synthesis steps. This four-membered ring
with a nitrogen and a carbonyl next to it is formed by fluoride induced
desilylation of an isoxazoline, followed by recyclization, resulting in the
four-cyclic beta-lactam (3). Isoxazoline (2) is formed by a 1,3-dipolar
cycloaddition with TMS-acetylene to a nitrone. Nitrone (1) in formed by a
condensation reaction. The fluoride source needs to be completely dry for
the last reaction to work, which TBAF – a well-known F- donor used by
Ahn et. Al. – is not, as proven by Dr. P. Contreras Carballada. In this
research, TBAT (Tetrabutylammonium difluorotriphenylsilicate) is tried as
a fluoride donor to no prevail so far. Further research is necessary to
realize this goal. Advised is to look further into F- donors or to tread a
different chemical route.
56
Roel Kerkers
Norbert Mulkins
Figure 1: Total synthesis of the beta-lactam.
Figure 2: H-NMR spectrum of nitrone (1).
Figure 3: H-NMR spectrum of isoxazoline (2).
[1] C. Ahn, J.W. Kennington and P. DeShong, “A New Approach to the Synthesis of Monocyclic -
Lactam Derivatives”, The Journal of Organic Chemistry, vol. 59, nr. 21, pp. 6282-6286, 1994
[2] P. Contreras Carballada “Synthesis of 5-silyl substituted Isoxazolines and their conversion to
beta lactames” – unpublished results
[3] C. J. Hayes, N. S. Simpkins, D. T. Kirk, L. Mitchell, J. Baudoux,A. J. Blake and C. Wilson,
“Bridgehead Lithiation-Substitution of Bridged Ketones, Lactones, Lactams, and Imides:
Experimental Observations and Computational Insights”, Journal of the American Chemical Society,
vol. 131, nr. 23, pp. 8196–8210, 2009.
57
A SAFER SYNTHESES OF ANTI-CANCER
AGENT FK866
AUTHORS
Steyn van Gerwen en Bas Schoone
SUPERVISOR
Dr. Paula Contreras Carballada
#Cancer #Anti-CancerAgent #OrganicChemistry #IR #HNMR
ABSTRACT
Cancer is the number 2 cause of death in the world, after heart disease.
Luckily, there are a lot of known treatments for patients with cancer.
Unfortunately, these treatments have several side effects. Chemotherapy
doesn’t only target the cells in a tumor, but also healthy fast-growing
cells. Hair loss is a common side effect of the therapy. Los of fertility and a
restless feeling also occur often. Radiotherapy has the same side effect.
This is why research into alternative treatments of cancer with less or no
side effects is needed.
To cure people of cancer, the cells inside the tumor have to be killed. This
can be done through apoptosis, programmed cell death. Because tumors
require lots of nutrition and energy, if the supply of energy can be
stopped, the cells undergo apoptosis. The enzyme NAPRT regulates the
energy supply inside of cells. By inhibiting NAPRT, cells can’t obtain
energy, which cause the cells to undergo apoptosis. Tissue around the
tumor will survive because of another energy obtaining route. Healthy
tissue uses a slower route than tumors via ATP and therefore live on.
One such inhibitor is FK866. In this synthesis harmful chemicals like sodium
azide or hydrazine are used. These compounds are deadly or toxic when
in contact with the skin, inhaled or swallowed. From this follows the
objective of this research, to synthesize FK866 through a safer synthesis
route.
58
Steyn van Gerwen
Bas Schoone
Figure 1: IR spectrum van 4-piperidinebutanol.
Figure 3: IR spectrum van 4-piperidinebutanol.
[1] Frontiers in Pharmacology, vol. 11, nr. 656, pp. 1 - 20, 2020.
[2] ChemMedChem, vol. 3, nr. 5, pp. 771 - 779, 2008.
[3] Patent WO2019171379A1, 8 2 2018.
Figure 2: HNMR spectrum van 4-piperidinebutanol.
59
60
Acknowledgements
Dear reader,
A global pandemic that keeps us in its grasp is what makes this
year stand out. Keeping 1.5 m distance from each other and with
face masks hiding our beautiful smiles, a work environment has
never been as anti-social as it was during this time. Nevertheless,
the minor/specialization of Polymer and Organic Chemistry (SPOC)
2021 has come to an end. But achieving greatness through
hardship is what makes us human. Full of energy and inspiration,
we students strive to deliver a product through our research that
makes the world of chemistry quiver with excitement. New ideas
and aspirations to make the world a better place. Greener
alternatives and a biobased future. We did all that within mere
months while being surrounded by negativity.
Special thanks go to the professors and technical staff for their
guidance during this minor; Paula Contreras Carballada, Kees
Kruithof, Jack van Schijndel, Betty Oostenbrink, Arnold Nijhuis,
Han van Kasteren and Qian Zhou, Thom Klein, Dennis Molendijk
and Koen van Beurden. Your support has been enlightening to
say the least.
Without further ado, we, the Book of Abstracts Committee, hope
you have enjoyed this book and that it has given you a glimpse of
the bright future of these remarkable students.
Although the path seems dark, and the times seem difficult,
please remember:
Per aspera ad astra.
Yours truly,
SPOC 2021
61
The Committee
Rachel Owusu-Oduro was born in
Amsterdam on the 7 th of August
2000 in a family of Ghanan origin.
She always found chemistry an
interesting subject and learned
with growing enjoyment during
her high school years. The thing
she likes the most about chemistry
is the power you have in the lab
to change matter and molecules,
and specifically organic chemistry
is her favourite topic. She would
like to continue in the academic
world with a MSc program at the
university but until then Paula is
trying to convince her to go to
Ghana for an internship.
Rachel is fluent in Dutch, Twi and
English and has a good
knowledge of German and French.
Mak Medaric was born in
Waalwijk on the 31st of July 1996
in a family of Bosnian origin. His
favorite topic in chemistry is
Organic Chemistry and Pharma, a
direction he would like to walk to
in the future. His grandfather was
a chemist and he worked at a
paper bleaching plant in Bosnia.
Conversations with his
grandfather opened his eyes to
the broad possibilities chemists
have, and led Mak to decide to
choose chemistry for his studies.
He has a completed a minor in
Business and Economics at the
Universitá Cattolica del Sacro
Cuore in Piacenza, Milan.
Mak is fluent in Dutch, Bosnian,
English and has a good
knowledge of German and Italian.
62
Paula Contreras-Carballada was born in Cologne, Germany, on the
12th of July 1977 in a family of Spanish origin. She decided to study
chemistry because she wanted to make medicines to cure children’s
illnesses and it was the only subject that made sense during high
school. She decided to become an organic chemist the day she
learned about the Diels-Alder cycloaddition. She received a MSc at
the Universidad Complutense de Madrid with a final project on
synthesis of antibiotics at the Technische Universität Berlin in 2003.
She completed a Phd in Photophysics at the University of Amsterdam
in 2009 and after a few years working as a post doc on hydrogen
evolution and artificial photosynthesis she became a chemistry
lecturer at Avans Hogeschool.
Paula is fluent in Spanish, German, English, French, Dutch, has
extensive knowledge of Italian and Dutch sign language and is
currently learning Japanese.
Dear Rachel, it was lovely working with you on the BofA project!! I
wish you all the best for the brilliant future that is waiting for you ;) !
Dear Mak, what an experience it has been to be your mentor this last
years! I wish you all the best making biobased polymers next year
and all the luck for the future ;) !
Paula
63