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Synthesis of coumarin derivatives and E a determination Autor Max van Liesdonk Academy of Technology for Health and Environment Avans Hogeschool, Breda Jack van Schijndel Kees Kruithof oumarin derivatives and E a determination Abstract The goal of this research is to determine what the activation energy of the synthesis of coumarin derivatives by using the Green Knoevenagel Condensatie. The molecules that will be synthesized in this project are 3 -carboxycoumarin and 3- carboxy-6-methylcourmarin. A second goal is to determine the difference in activation energy when using different types of katalysts, which are ammonium bicarbonate and piperidine. To determine the reaction rate constant (k) rate every different reaction is done under 2 different temperatures. All together giving a total of 8 reactions that have to be followed in time by taking samples. From these samples the concentration of the reactants and product are determined. The gathered information can then be used to calculate the k form there the E a is calculated. Expectations for these experiments will be that the use of ammonium bicarbonate will give a lower activation energy then piperidine. Using the Green Knoevenagel reaction gives a mechanism which contains whats called a katalitic intermediair. The third goal is comparing the E a of the syntheses by using ammonium bicarbonate or the pre-synthesized katalytic intermediair to make 3-carboxycoumarin. The used method for synthesizing these components is adding salicylaldehyde, malonic acid and a catalyst in a reactor and let it stir for 1 hour at 90°C [1][2][3]. Keywords: Green Knoevenagel Condensation, katalytic intermediair, coumarin, activation energy, reaction rate constant Table of content Figure 1: The Green Knoevenagel reaction how it is used in this research project. [1] Temperature dependent green synthesis of 3-carboxycoumarins and 3,4- unisubstituted coumarins, 2018. [2] Mechanistic insight in the green knoevenagel reaction of furanic aldehydes using ammoniums salts as catalyst, 2018 [3] Chemical kinetics, 2017 24
Determination of activation energies of 3,4-unsubstituded coumarine synthesis using the green Knoevenagel condensation Autor Maudy Robben f coumarin derivatives and E a determination Academy of Technology for Health and Environment Avans Hogeschool, Breda Jack van Schijndel Kees Kruithof Abstract Coumarins are heterocyclic aromatic compounds and can be obtained naturally or synthetically. One of the synthesis routes to obtain coumarins is the solvent-free green Knoevenagel condensation[1]. The purpose of this research was to synthesize two 3,4-unsubstituded coumarins (standard coumarin and 6-carboxycoumarin) out of hydroxybenzaldehydes (2-hydroxybenzaldehyde and 2-hydroxy-5-methoxybenzaldehyde) (Figure 1). In this reactions was malonic acid and ammonium bicarbonate or piperidine used. Of all these synthesis, was the activation energy determined by carrying out the reaction to carboxycoumarins at 70⁰C and 90⁰C during 60 minutes. The carboxycoumarins were decarboxylated by heating the mixture during 120 minutes at a temperature of 140⁰C. The determined activation energies have been compared. As a side study has the catalytic intermediate (Figure 2) of the reaction between 2 -hydroxybenzaldehyde and ammonium bicarbonate been synthesized by heating those substances during 30 minutes at 50⁰C. The intermediate has been precipitated in a 30% ammonia solution. In co-operation with a research group at Avans is a comparison made between the activation energy of the reaction where the catalytic intermediate has been formed during the reaction and between the activation energy of the reaction where the catalytic intermediate has been formed previously. All products have been analysed by TLC, IR, NMR, melting point determination and HPLC. Keywords: Coumarin, green Knoevenagel condensation, catalytic intermediate Table of content Figure 1: Reaction equation of the coumarin synthesis . Figure 2: Catalitic intermediate. [1] J. van Schijndel, D. Molendijk, L. A. Canalle, E. T. Rump en J. Meuldijk, „Temperature Dependent Green Synthesis of 3 - Carboxycoumarins and 3,4-unsubstituded Coumarins,” Bentham Science, p. 6, 2017. 25
Page 1 and 2: Book of Abstracts Poster presentati
Page 3 and 4: Avans University of Applied Science
Page 5 and 6: Collaborations 5
Page 7 and 8: Preface Dear reader, We present her
Page 9 and 10: Index SPOC1 13 Tutor: Nishant Sewgo
Page 11 and 12: Group index SPOC1 The inhibition of
Page 13 and 14: The inhibition of the Pseudomonas A
Page 15 and 16: Synthesis of a surface-active RAFT-
Page 17 and 18: Synthesis for a building block for
Page 19 and 20: 19
Page 21 and 22: Group index SPOC2 In situ catalysed
Page 23: Book of abstracts SPOC 2018 3,4-uns
Page 27 and 28: Book of abstracts SPOC 2018 Synthes
Page 29 and 30: Group index SPOC3 Decarboxylation o
Page 31 and 32: Decarboxylation of ferulic acid to
Page 37 and 38: Group index SPOC4 The kinetics of t
Page 39 and 40: The kinetics of the Knoevenagel con
Page 41 and 42: Isolation of catalytic intermediate
Page 43 and 44: Chemical recycling to Oxazolines Au
Page 45 and 46: Group index SPOC5 Molecular Imprint
Page 47 and 48: Taxus extract Molecular Imprinted P
Page 49 and 50: MIP synthesis of 4-vinylpyridine Au
Page 51 and 52: Biobased Block-Copolymers due ATRP
Page 53 and 54: 53
Page 55 and 56: Group index SPOC6 Synthesis of Beta
Page 57 and 58: Synthesis of Beta-lactam in three s
Page 59 and 60: Isoxazoline ring opening by TBAT to
Page 61 and 62: Synthesis of a ligand for a synthet
Page 63 and 64: Group index SPOC7 Synthesis of a te
Page 67 and 68: Synthesis of a terpyridine ligand f
Page 69 and 70: Synthesis of peptides for IR foldin
Page 71 and 72: Peptide synthesis for unravelling p
Page 73 and 74: Dear reader, Acknowledgement s Afte

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