SINTESIS SENYAWA 2-CYANOPROP-2-YL DITHIOBENZOATE SEBAGAI CHAIN TRANSFER AGENT PADA POLIMERISASI REVERSIBLE ADDITION-FRAGMENTATION CHAIN TRANSFER

  • James Sibarani Program Studi Kimia, Fakultas MIPA Universitas Udayana, Bali-Indonesia
  • Oscar Yonathan Hambiyono Program Studi Kimia, Fakultas MIPA Universitas Udayana, Bali-Indonesia
  • Manuntun Manurung Program Studi Kimia, Fakultas MIPA Universitas Udayana, Bali-Indonesia
  • Ni Made Puspawati Program Studi Kimia, Fakultas MIPA Universitas Udayana, Bali-Indonesia

Abstract

2-Cyanoprop-2-yl Dithiobenzoate merupakan salah satu transfer agen pada polimerisasi Reversible Addition-Fragmentation Chain Transfer (RAFT). Senyawa ini telah banyak digunakan dalam proses sintesis polimer yang diperuntukan dalam bidang kesehatan. Tujuan penelitian ini adalah untuk mensintesis 2-cyanoprop-2-yl dithiobenzoate. Senyawa tersebut disintesis elalui proses pembentukan senyawa asam ditiobenzoat dan di(tiobenzil) disulfida sebagai senyawa antara atau intermediet. Keberhasilan pembentukan senyawa target dipastikan dengan menggunakan Fourier Transform Infrared (FTIR) dan Nuclear Magnetic Resonance (13C-NMR dan 1H-NMR). Serapan pada bilangan gelombang 2239,36 cm-1 merupakan karakteristik untuk gugus (CN) dan serapan dengan bilangan gelombang 854 cm-1 dan 773 cm-1 merupakan karakteristik untuk gugus tiol (-C-SH). Sedangkan pada 1H-NMR terdapat serapan dengan pergeseran kimia 1,55 ppm yang mengindikasikan bahwa produk yang dihasilkan merupakan campuran. Spektra 1H-NMR memberikan pergeseran kimia pada 1,4 –1,7 ppm (proton CH3) dan 7,7 - 8,1 ppm (proton aromatik) . Spektra 13C-NMR memberikan pergeseran kimia 10,0 – 30,0 ppm (karbon CH3), 69,0 – 70,5 ppm (karbon OCH3), 120,00 – 121,00 ppm (karbon CN), 123,00 – 124,00 ppm (karbon S-C-CN), 130,00 – 140,00 ppm (karbon aromatik), dan 178,00 – 181,00 ppm (CS2). Dapat disimpulkan bahwa sintesis senyawa 2-cyanoprop-2-yl dithiobenzoate sudah berhasil dilakukan dengan rendemen sebesar 84,7%.


 


The purpose of this study was to synthesize 2-cyanoprop-2-yl dithiobenzoate, one of the transfer agents on Reversibble Addition-Fragmentation Chain Transfer (RAFT) polymerizations widely used in polymer synthesis processes intended for health purposes. The compound was synthesized through the formation of dithioobenzoic acid and di(thiobenzyl) disulfide as intermediate compounds. The confirmation of the reaction was conducted by Fourier Transform Infrared (FTIR) and Nuclear Magnetic Resonance (1H-NMR and 13C-NMR). The FTIR spectrum confirmed the formation of the target compound with some characteristic bands at 2289.36 cm-1 assigned for –CN and at 854 cm-1 and 773 cm-1 assigend for –CS group. Moreover, the 1H-NMR spectrum showed chemical shifts at 1.4 – 1.7 ppm and 7.7 – 8.1 pmm assigned for –CH3 and aromatic protons respectively. The 13C-NMR spectrum showing chemical shifts at 10.0 – 30.0 ppm (-CH3), 69.0 – 70.5 ppm (-OCH3), 120.0 – 121.0 ppm (-CN), 123.0 – 124.0 ppm (-S-C-CN), 130.0 – 140.0 ppm (aromatic carbons), and 178.0 – 181.0 ppm (-CS2-) also confirmed the formation of the target compound. It can be concluded that the synthesis of 2-cyanoprop-2-yl dithiobenzoate has been successfully carried out with a yield of 84.7%.

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References

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Published
2019-05-31
How to Cite
SIBARANI, James et al. SINTESIS SENYAWA 2-CYANOPROP-2-YL DITHIOBENZOATE SEBAGAI CHAIN TRANSFER AGENT PADA POLIMERISASI REVERSIBLE ADDITION-FRAGMENTATION CHAIN TRANSFER. CAKRA KIMIA (Indonesian E-Journal of Applied Chemistry), [S.l.], v. 7, n. 1, p. 20 - 27, may 2019. ISSN 2302-7274. Available at: <https://ojs.unud.ac.id/index.php/cakra/article/view/51313>. Date accessed: 07 oct. 2022.