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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

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Collaborations

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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

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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

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18

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34

42

52

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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

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14

16

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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.

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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.

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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]

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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.

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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.

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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.

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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

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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.

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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.

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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.

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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

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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.

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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.

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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.

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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”.

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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

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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.

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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.

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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.

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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,

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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

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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.

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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

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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.

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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.

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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


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