IDENTIFICATION BY GAS-LIQUID CHROMATOGRAPHY-MASS SPECTROMETRY OF LOW-MOLECULAR-WEIGHT PRODUCTS FROM THE AQUEOUS ALKALINE-DEGRADATION OF CELLULOSE

Low-molecular-weight products from the degradation of pure cellulose in 0.3-0.65M sodium carbonate or hydrogencarbonate at 300° have been identified by g.l.c-m.s. Both the aqueous residual phase and the floating-oil product phase were examined, and contained essentially the same compounds, which were further characterized by the trifluoroacetyl derivatives. They consisted primarily of unsaturated aliphatic and alicyclic hydrocarbons, aldehydes, ketones, alcohols, and furans. Specifically identified were cyclopentanone, cyclohexanone, phenol, cresols, 2-ethyl- cyclopentanone, 2- or 3-methylcyclopentanone, 2,5-dimethyl-2- cyclopentenone, acrolein, 2,5-dimethyl-2,4-hexadiene, and octene. Probably present were 2,4-dimethylfuran, 2,5-diethylfuran, ethylmethylfuran, 4-octyne, and decyne. The formation of these compounds demonstrates not only the degradation of cellulose but the resynthesis of molecules with carbon-chain lengths greater than 6 atoms. © 1979.