Effect of Water on Fructone Synthesis from Ethyl Acetoacetate
Asep Kadarohman1,*, Iim Ismaya1, Sopi Alawiah1, Ratnaningsih E. Sardjono1, Amelinda Pratiwi1, Vidia Afina1, and LL Khumaisah2

1 Department of Chemistry Education, Faculty of Mathematics and Science Education, Universitas Pendidikan Indonesia, Jalan Dr. Setiabudhi No. 229 Bandung 40154, Indonesia
2 Department of Chemistry, Faculty of Science and Technology, Universitas Muhammadiyah Sukabumi, Jalan R. Syamsudin, S.H. No. 50 Sukabumi 43113 Indonesia
* Email: kadar[at]upi.edu

Abstract

The reaction of the synthesis of fructone (Ethyl 2-methyl-1,3-dioxolan-2-acetate) from ethyl acetoacetate with an acid catalyst produces 2-methyl-2-(ethoxycarbonylmethyl)-1,3-dioxolane and triethylene glycol diacetate as side products. This research aims to study the effect of water on increasing the amount of fructone produced and reducing the amount of side products. Fructone synthesis reaction uses a reflux system with azeotrope technique equipped by Dean Stark to attract water with cyclohexane as a solvent. Fructone synthesis reaction was carried out at a mole ratio of ethyl acetoacetate and ethylene glycol 1:2 with sulfuric acid and para toluene sulfonic acid as catalysts at temperature of 78 oC, 80 oC, and 82 oC. To determine the effect of water, a fructone synthesis reaction was carried out without using the azeotrope technique and the azeotrope technique with variations in the amount of cyclohexane 20 mL, 30 mL, and 40 mL. The reaction products were analyzed by GC and GCMS. It was found that reducing the amount of water in the reaction system increased the amount of fructone produced. The addition of cyclohexane as an azeotrope reduces the number of side products. The amount of fructone produced in the use of sulfuric acid and para toluene sulfonic acid catalysts is almost the same. In the fructone synthesis reaction at 80 oC, 40 mL cyclohexane, 2 hours reaction time, and 0.006 moles H2SO4 catalyst, 95.66% fructone was produced, the remaining unreacted ethyl acetoacetate was 3.24% and the by-product was 1.1%.

Keywords: Synthesis, fructone, water

Topic: Organic Synthesis and Medicinal Chemistry