Synthesis and Characterization of Isothiocyanate Poly(Methyl Eugenol) and Thiosemicarbazide Poly(Methyl Eugenol)

Abstract

Abstract. This study investigates the synthesis, chemical, and physical properties of isothiocyanate poly(methyl eugenol) or IPME and thiosemicarbazide poly(methyl eugenol) or TPME. The IPME synthesis as a precursor was firstly carried out by reacting Methyl Eugenol (ME) with potassium hydrogen sulfate and potassium thiocyanate in chloroform solution at room temperature. The TPME was synthesized using the intermediate compound and hydrazine in an ethanol-based at 70 °C for five hours. The IPME and TPME were observed by FTIR, dissolution test, SEM-EDX, XRD, GCMS, and LCMS-MS. The methyl eugenol : HSCN = 1:10 (mmol) ratio for 30 hours of reaction time was determined for the optimum IPME production. FTIR spectra consecutively identified specific wavenumbers at around 2049 cm-1 and 3488 cm-1 for isothiocyanate and thiosemicarbazide functional groups. IPME and TPME compounds were entirely soluble in DMSO and slightly soluble in n-hexane. SEM-EDX study showed that IPME had a denser surface than TPME; however, they all consisted of Carbon, Oxygen, Nitrogen, and Sulfur elemental composition. XRD analysis indicates that these two products were high and moderate crystalline compounds. The GCMS analysis showed m/z 503 for IPME, predicting that IPME was a copolymer composed of one methyl eugenol isothiocyanate molecule and two methyl eugenol bonded. The LCMS-MS chromatogram with m/z 449 for TPME proved the occurrence of a polymerization reaction.Keywords: Isothiocyanate, methyl eugenol, thiosemicarbazide.