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Gas chromatography/mass spectrometric characterisation of pyrolysis/silylation products of glucose and cellulose
Author(s) -
Fabbri Daniele,
Chiavari Giuseppe,
Prati Silvia,
Vassura Ivano,
Vangelista Marta
Publication year - 2002
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.856
Subject(s) - chemistry , levoglucosan , silylation , trimethylsilyl , pyrolysis , cellulose , maltol , mass spectrum , mass spectrometry , organic chemistry , gas chromatography , electron ionization , chromatography , catalysis , ionization , ion , aerosol , biomass burning
The mass spectra of trimethylsilyl (TMS) derivatives of possible hydroxylated pyrolysis products of glucose and cellulose were recorded by gas chromatography/mass spectrometry (GC/MS) analyses of TMS derivatives of 2‐hydroxymethylfuran, 2‐hydroxy‐1‐methyl‐1‐cyclopenten‐3‐one, 5‐(hydroxymethyl)‐2‐furaldehyde, 5‐methyl‐2‐furoic acid, 4‐hydroxy‐6‐methyl‐(2 H )‐pyran‐2‐one, 2‐methyl‐3‐hydroxy‐(4 H )‐pyran‐4‐one (maltol) and 1,6‐anhydro‐β‐D‐glucopyranose (levoglucosan, LG). Also, 2‐ O ‐TMS‐1,6‐anhydro‐β‐D‐glucopyranose, 4‐ O ‐TMS‐1,6‐anhydro‐β‐D‐glucopyranose and 2,4‐bis‐ O ‐TMS‐1,6‐anhydro‐β‐D‐glucopyranose were identified from the interpretation of electron impact and chemical ionisation mass spectra of products obtained from partially silylated levoglucosan solutions, together with information from the known relative reactivities of OH groups of anhydrosugars. A peak at m/z 116 was found to be characteristic of the mass spectra of partially silylated anhydrosugars, and is absent from the mass spectra of the persilylated species. Pyrolysis/GC/MS of cellulose in the presence of hexamethyldisilazane afforded principally the 2‐ and 4‐TMS ethers and the 2,4‐bis‐TMS ether of LG, whereas the 5‐TMS‐oxymethyl‐2‐furaldehyde was a prominent pyrolysis/silylation product of glucose. The mass spectra of other relevant pyrolysis/silylation products are presented. Copyright © 2002 John Wiley & Sons, Ltd.