Replacing Benzyl Chloride with a Lignin-degradation Product in Cellulose Etherification Decreases the Melting Point

A cellulose ether that is easier to melt than benzyl cellulose was produced from the lignin degradation product veratryl alcohol. Veratryl chloride and bromide were synthesized from the alcohol, and these two chemicals were used to react with Avicel (R) cellulose to form the novel cellulose ether veratryl cellulose (VC). Spectroscopic characterisation techniques (1H NMR, FTIR) indicated the successful conversion of Avicel (R) cellulose to the cellulose ether VC, by both routes, at a degree of substitution of 1.4 to 1.6. Melting measurements of the VC samples showed a gradual softening from approximately 110 degrees C; the VC was melted below 200 degrees C. XRD analysis confirmed that the chemical treatments affect the degree of crystallinity. Size exclusion chromatography results showed that the products diller remarkably in molecular weight. The VC synthesized with veratryl chloride degraded almost twice as much as when veratryl bromide were used. The cellulose ethers were soluble in DMSO, DMAc, and CHCI3.

Automated summary

A new cellulose ether VC, which is easier to melt than benzyl cellulose, was synthesized from the lignin degradation product veratryl alcohol. VC showed a gradual softening from approximately 110 degrees C and can be dissolved in specific solvents.