Preparation and characterization of cellulose p-phenylbenzoate by two-step synthesis from microcrystalline and kraft cellulose

• DOI: 10.1007/s00289-015-1451-z
• Publication Date: 2015-07-08T13:06:54Z
• Authors: Lahcen El Hamdaoui; Mohammed El Mouss...; Said Gmouh
• Keywords: Thermogravimetric analysis

Synthesis and structural characterizations of p-bromobenzoate and p-phenylbenzoate of cellulose were carried out. Cellulose derivatives were synthesized by esterification and Suzuki–Miyaura coupling. p-Bromobenzoylation produced 75 % yield by treating a mixture of microcrystalline or kraft cellulose, and p-bromobenzoyl chloride at 80 °C in 1-N-butyl-3-methylimidazolium chloride (Bmim)[Cl] for 2 h. The effects of reaction time, temperature and molar ratio of p-bromobenzoyl chloride/anhydroglucose unit on degree of substitution (DS) value of cellulose p-bromobenzoate were investigated. Cellulose p-bromobenzoate was then coupled with phenyl boronic acid with 87 % yield using standard Suzuki–Miyaura coupling conditions in dimethyl sulfoxide (DMSO). The structure as well as the properties of the obtained product was characterized using different analytical tools such as Fourier transform infrared (FT-IR) spectroscopy, nuclear magnetic resonance (NMR) and thermogravimetric analysis (TGA).