Book of abstracts version 5

Synthesis of a surface-active RAFT-agent 4-thiobenzyl
sulfanylmethyl benzoate
hesis of a surface-active RAFT-agent 4-thiobenzyl sulfanylmethyl benzoa
Author
Rashmi Garib
Academy Synthesis of Technology for of Health a surface-active and Environment RAFT-agent 4-thiobenzyl
Avans Hogeschool, Breda
sulfanylmethyl benzoate
Sonny van Seeters
Nishant Sewgobind
Abstract
In this study, a surface-active RAFT-agent, 4-thiobenzoyl sulfanylmethyl benzoate, was synthesized and characterized for
further emulsion polymerization (figure 1). RAFT-agents are very expensive and hard to purify. They can be used at a large
scale of monomers, including determination of molecular weight. A surface active RAFT-agent is partially polair and
partially apolair, this way it is easier to polymerize a block copolymer instead of using a normal RAFT-agent. After
synthesizing it is expected to have similar characteristics in H 1 -NMR spectrum [1] (figure 2).
The first step is the attack of the Grignard reagent with carbon disulfide in dry THF and under dry conditions. Second is
adding 2:1 molar ratio to the synthesized magnesium benzodithioate bromide and 4 -(bromomethyl)benzoate acid. After
these steps, the unreacted reagents were removed by distillation under pressure[2] . L/L-extraction with acidified water of
a pH level between 1-2, MTBE and 1M NaOH to deprotonate[3]. The product was characterized with LC -MS and H 1 -NMR.
Keywords: RAFT-agent, living radical polymerization
Table of content
Figure 4: Reaction scheme of the synthesis of 4-thiobenzoyl sulfanylmethyl
benzoate.
Figure 3: H 1 -NMR spectrum of synthesized
product.
[1] H. Lee, S. E. Shim, H. Jung en S. Choe, „Poly(methyl methacrylate) Latex Prepared by living free radical Emulsion
polymerization using a sufrace active iniferter (Suriniferter) and its properties,” Applied Chemistery, may 2003
[2] S. E. Shim, H. Jung, H. Lee, J. Biswas en S. Choe, „Living radical dispersion photopolymerization of styrene by a
reversible addition - fragmentation chain transfer (RAFT) agent,” Polymer, vol. 2003, nr. 14 july, p. 10, 2003.
[3] Y. K. Chong, K. Julia, T. P. T. Le, G. Moad, A. Postma, E. Rizzardo en S. H. Thang, „Thiocarbonylthio Compounds
[S=C(Ph)S-R] in Free Radical Polymerization with Reversible Addition-Fragmentation Chain Transfer (RAFT Polymerization).
Role of the Free-Radical Leaving Group (R),” p. 17, 16 December 2002.
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