Catalytic pyrolysis of cellulose was carried out focusing on the selective production of the anhy-drosugar (1R,5S)-1-hydroxy-3,6-dioxa-bicyclo[3.2.1]octan-2-one (LAC), a promising chiral chemical forapplication in organic synthesis. The catalyst Sn-MCM-41, montmorillonite K10 or aluminum titanatenanopowder was used by a suitable pyrolysis reactor performing the processes at 500◦C and 350◦C. Aftera workup adapted to optimize the production of LAC and to facilitate the following purification, its amountin the produced bio-oil samples was established by1H NMR spectroscopy using the standard-additionmethod. A further quantitative analysis was based on FT-IR technique performed using a CaF2liquid celland employing the calibration-curve method. Both the methods, which do not require any pre-treatmentsteps, provided comparable values (±1%) in terms of LAC abundance in bio-oil samples and validation ofthe FT-IR based method made it a rapid and efficient tool for quantitative LAC detection also without needof carbonyl band deconvolution. The data showed that (i) Sn-MCM-41 promoted the highest LAC produc-tion by pyrolysis at 500◦C (7.6 ± 0.1 wt.% from cellulose), with a lower than 1% decrease in the presence ofthis catalyst after a regeneration cycle, and (ii) the cheap and eco-friendly montmorillonite K10 emergedas the best alternative, with a yield from cellulose of 4.8 ± 0.1 wt.% at 500◦C and 4.6 ± 0.1 wt.% at 350◦C.

Upgraded production of (1R,5S)-1-hydroxy-3,6-dioxa-bicyclo[3.2.1]octan-2-one from cellulose catalytic pyrolysis and its detection in bio-oils by spectroscopic methods

Mancini, Ines;Dosi, Federico;Defant, Andrea;Miotello, Antonio
2014

Abstract

Catalytic pyrolysis of cellulose was carried out focusing on the selective production of the anhy-drosugar (1R,5S)-1-hydroxy-3,6-dioxa-bicyclo[3.2.1]octan-2-one (LAC), a promising chiral chemical forapplication in organic synthesis. The catalyst Sn-MCM-41, montmorillonite K10 or aluminum titanatenanopowder was used by a suitable pyrolysis reactor performing the processes at 500◦C and 350◦C. Aftera workup adapted to optimize the production of LAC and to facilitate the following purification, its amountin the produced bio-oil samples was established by1H NMR spectroscopy using the standard-additionmethod. A further quantitative analysis was based on FT-IR technique performed using a CaF2liquid celland employing the calibration-curve method. Both the methods, which do not require any pre-treatmentsteps, provided comparable values (±1%) in terms of LAC abundance in bio-oil samples and validation ofthe FT-IR based method made it a rapid and efficient tool for quantitative LAC detection also without needof carbonyl band deconvolution. The data showed that (i) Sn-MCM-41 promoted the highest LAC produc-tion by pyrolysis at 500◦C (7.6 ± 0.1 wt.% from cellulose), with a lower than 1% decrease in the presence ofthis catalyst after a regeneration cycle, and (ii) the cheap and eco-friendly montmorillonite K10 emergedas the best alternative, with a yield from cellulose of 4.8 ± 0.1 wt.% at 500◦C and 4.6 ± 0.1 wt.% at 350◦C.
Mancini, Ines; Dosi, Federico; Defant, Andrea; Crea, F.; Miotello, Antonio
File in questo prodotto:
File Dimensione Formato  
JAAP2014.pdf

Solo gestori archivio

Tipologia: Versione editoriale (Publisher’s layout)
Licenza: Tutti i diritti riservati (All rights reserved)
Dimensione 1.01 MB
Formato Adobe PDF
1.01 MB Adobe PDF   Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11572/97944
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 12
  • ???jsp.display-item.citation.isi??? 12
social impact