NOVEL CELLULOSIC ETHERS WITH LOW DEGREES OF SUBSTITUTION .1. PREPARATION AND ANALYSIS OF LONG-CHAIN ALKYL ETHERS

Twenty 'hydrophobic' ethers (S1-S20) of hardwood cellulose were prepared by reaction with suitable alkane derivatives in the presence of alkali (sodium hydroxide or hydride) and either isopropanol or dimethyl sulfoxide. The alkylating reagents were the 1-bromo-, 1-iodo-, or 1,2-epoxy-derivatives of butane, octane, decane, dodecane, tetradecane, hexadecane and octadecane. The products were characterised by elemental analysis, FT-IR spectroscopy, thin layer chromatography (TLC) and [H-1](NMR) nuclear magnetic resonance degraded of samples by acetolysis and gas-liquid chromatography (GLC) and mass spectrometry (MS) of the alditol acetates prepared from the acetolysates. The capacities of the products to bind a hydrophilic dye (methylene blue) were also measured. Degrees of substitution (DS) ranging from <0.01 to 0.58 were found. All of the derivatives retained some of the fibrous character of the cellulose, and those of higher DS floated on water like cork.