HYDROGENATION OF FURFURAL TO FURFURYL ALCOHOL WITHOUT H2 BY NI(0) COMPLEXES

• Main Author: Ibnu Sulistia, Azi
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/64838
• Institution: Institut Teknologi Bandung

Furfural (FALD) is commonly produced from dehydration of xylose (C5 sugar resulting from hydrolysis of lignocellulose with an acid catalyst). FALD may be hydrogenated with a metal catalyst to form furfuryl alcohol (FOL). FOL is used in the resin industries, synthetic fibers, renitidine synthesis, and as an intermediate in the synthesis of tetrahydrofurfuryl alcohol, methyl furan, and polyfurfuryl alcohol. In most cases, hydrogenation reactions use pressurized H2. Hydrogen has low solubility in organic solvents (3.7?10?3 M ). Thus, hydrogen is used typically at high pressure (30-100 bar). Reactions with high-pressure hydrogen require relatively a sophisticated piping system. Therefore, research on hydrogenation with other hydrogen sources grows significantly. The method involves the addition of alcohols or organic acids. Primary and secondary alcohols has been used as effective hydrogen sources. As a pre-catalyst, NiCl2(PPh3)2, NiCl2(en)x (en = ethylenediamine), and NiCl2(o-PDA)y (o-PDA = o-phenylenediamine) were examined in the reaction. The complexes were reduced by Zn in situ to generate active complexes of Ni(0). FALD conversion of 87% and FOL yield of 42% were achieved when NiCl2(PPh3)2 of 1 mol% was employed in the reaction at 160 oC for 7 h in ethanol and with Zn as a reducing agent. The selectivity of FOL under this condition was 48%, with 8% of acetal (2-(diethoxymethyl)furan) and 44% of an unknown product. The acetal may be formed from the acetalization of furfural, catalyzed by unreduced Ni(II)