EPOXIDATION OF PALM OIL CATALYZED BY COMPLEX OF VANADYL PHENOXYIMINE

• Main Author: Putri Deningsih, Amelia
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/75790
• Institution: Institut Teknologi Bandung

Phthalates are chemicals that can be used as a plasticizer. Currently, the use of phthalate compounds is prohibited and limited due to the negative impact of phthalate compounds on the growth and development of children, the endocrine system and the reproductive system. Indonesia is the world's largest producer of palm oil (crude palm oil or CPO). One of the chemicals that can be reacted from palm oil is epoxidized palm oil (EPO). EPO can be an alternative to replace harmful phthalate compounds. Epoxidation is a chemical reaction that converts carbon double bonds (olefins) into oxiranes (epoxides). In previous studies, it was reported that epoxidation of palm oil could proceed with relatively low heat release using TBHP 70% and a catalyst. In this study, metal vanadium was prepared to become VO(acac)2, which was metallized with the phenoxyimine ligand FI-1 using a 4-nitroaniline precursor and FI-2 using a 3-nitroaniline precursor, forming vanadyl phenoxyimine complexes VO(FI-1)2 and VO(FI-2)2. The synthesis results were confirmed by FTIR, PXRD and 1H-NMR characterization. The catalytic test was carried out on the EPO reaction with vanadyl phenoxyimine VO(FI-1)2 catalyst and was characterized using 1H-NMR, there was an increase in the intensity of the methine proton resonance of the epoxidized group at a chemical shift of 2.8-3.0 ppm which indicated the presence of catalytic activity. The optimum conditions for the epoxidation of palm oil catalyzed by vanadyl phenoxyimine VO(FI-1)2 were 0.3 mol% catalyst VO(FI-1)2, 5 meq TBHP 70%, temperature 80 oC for 8 hours. The optimum condition results give an epoxidation value of 71%. The calculated turnover number (TON) under the optimum conditions of the vanadyl phenoxyimine VO(FI-1)2 catalyst was 479, while the turnover frequency (TOF) value was 60 per hour. Reaction kinetics studies show that the reaction is pseudo first order. Rate constant values (kobs) at temperatures 60 oC, 80 oC and 90 oC were 0.0185 hour-1 , 0.0261 hour-1 and 0.0298 hour-1 respectively, which means they tended to increase as the temperature increased. The activation energy (????a) obtained with the catalyst VO(FI-1)2 is 16 kJ.mol-1 , while without a catalyst it is 127 kJ.mol-1 . Other kinetic calculations with the catalyst VO(FI-1)2, obtained the activation enthalpy (?H ‡ ) is 13 kJ.mol-1 , the activation entropy (?S ‡ ) is -239 kJ.mol-1 .K-1 , and the Gibbs free energy of activation (?G ‡ ) is 97 kJ.mol-1 . If without a catalyst, the activation enthalpy (?H ‡ ) is 129 kJ.mol-1 , activation entropy (?S ‡ ) is -640 kJ.mol-1 .K-1 , and the Gibbs free energy of activation (?G ‡ ) is 355 kJ.mol-1 .