title: Gas chromatography/mass spectrometric characterisation of pyrolysis/silylation products of glucose and cellulose.
abstract: 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-(2H)-pyran-2-one, 2-methyl-3-hydroxy-(4H)-pyran-4-one (maltol) and 1,6-anhydro-beta-D-glucopyranose (levoglucosan, LG). Also, 2-O-TMS-1,6-anhydro-beta-D-glucopyranose, 4-O-TMS-1,6-anhydro-beta-D-glucopyranose and 2,4-bis-O-TMS-1,6-anhydro-beta-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.
authors.affiliation: Laboratorio di Chimica Ambientale, C.I.R.S.A. - Università di Bologna, via Marconi 2, 48100 Ravenna, Italy. dfabbri@ambra.unibo.it
authors.forename: Daniele
authors.initials: D
authors.lastname: Fabbri
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Chiavari
authors.forename: Silvia
authors.initials: S
authors.lastname: Prati
authors.forename: Ivano
authors.initials: I
authors.lastname: Vassura
authors.forename: Marta
authors.initials: M
authors.lastname: Vangelista
mesh_terms: D002482:Cellulose / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D005947:Glucose / Q000737:chemistry*; D006358:Hot Temperature; D015394:Molecular Structure
chemical_list: D002482:Cellulose; D005947:Glucose