LAURYL GLUCOSIDE SYNTHESIS FROM GLUCOSE BROMIDE WITH DODEXIDE VIA WILLIAMSON ETHER SYNTHESIS REACTION

• Main Author: AKBAR FAJRIANSYAH NIM:10511040
• Format: Final Project
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/25259
• Institution: Institut Teknologi Bandung

Lauryl glucoside was synthesized from the reaction of bromoglucose, 2,3,4,6-tetra-acetyl-α-D-bromo glucopyranose (which has been protected by acetylation process), with dodexide via Williamson ether synthesis reaction method. Lauryl glucoside is a surfactant compound belonging to the glucolipid group; which is environmentally friendly "biodegradable", and has good toxicity properties (not irritating to the skin) and they can be synthesized from natural sources. The compounds in this group have been widely used in industrial cleaning materials (detergents), cosmetics, and dyes. In this study, the intemediet compound of glucose pentaacetate (1,2,3,4,6-penta-acetyl-β-D-glucopyranose) was synthesized by reacting glucose with acetate anhydride in an equivalent amount (1:1 mol). This product was purified by recrystallizing in a methanol solvent. The formation of intermediate products was ensured through FTIR analysis; which contains with the uptake of a typical number of OH, 3600 cm-1, which proves the OH group is replaced by an acetate group. While the acetate group attached to the absorption atoms in the wave number 1730 cm-1. Meanwhile, value of observation of thin layer chromoatography with the eluen of n-hexane: ethyl acetate (1: 1) showed Rf 0.52 (corresponding to the data literature). Furthermore, the bromination process of the intermediate compound (1,2,3,4,6-penta-acetyl-β-D-glucopyranose) was carried out by reacting the pentaacetic glucose with HBr solution 33% in an equivalent amount (moles) in glacial acetic acid, for 24 hours, at room temperature. The FTIR analysis of 2,3,4,6-tetra-acetyl-α -D-bromo glucopyranose products showed the formation of C-Br bonds, at 500-600 cm-1 waves. The thin layer chromatography observation of this product showed a Rf of 0.48, which corresponds to the literature data. Dodexide (alkoxide) is prepared from dodecanol using a method that reduces the methodology developed by Vacek, 1984. The obtained lauryl glucoside product, then characterized using FTIR and 1H NMR analysis; where the FTIR measurement results show the presence of C-O-C group with wake up absorption at 1054 cm-1 wave number. Meanwhile, the results of a 1H NMR measurement of lauryl glucoside product gave three peaks in the expected chemical shifts of lauryl glucoside based on literature reference data.