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Molecular modelling approach to elucidate the thermal decomposition routes of vanillin


The presence of huge number of oxy-components in the unprocessed bio-oil, after thermochemical conversion of lignocellulosic biomass, is an undesired property of bio-oil. This results into severe drawbacks of raw bio-oil which are not considered as desirable characteristics of any fuel, e.g., low heating value, corrosiveness, high viscosity, low stability, etc. Therefore, the elimination of oxygen atoms from the components of bio-oil becomes mandatory. On the other hand, the huge number of oxy-components in the unprocessed bio-oil offers a fantastic platform to accomplish various specialty chemicals. Therefore, in this work, the vanillin (4-hydroxy-3-methoxy-benzaldehyde) component is considered as a model compound of lignin derived bio-oil and carried out various chemical conversions to achieve lower molecular weight hydrocarbon fractions and several important intermediates, e.g., benzene, guaiacol, o-cresol, p-hydroxybenzaldehyde, m-methoxybenzaldehyde, phenol and o-quinonemethide. The bond dissociation energy study is carried out to observe the potential chemical breakage site of vanillin. According to the various bond dissociation possibility, the chemical reaction is proceeded and reported as a potential energy surface for each reaction scheme. The production of guaiacol from vanillin using atomic hydrogenation at the aromatic carbon of Caromatic-CHO bond of vanillin followed by formyl group removal is found to be the least activation energy (10.13 kcal/mol only) demanding pathway. The present results are in the accordance with their experimental counterparts wherever applicable. The thermochemical phenomena of these reactions are carried out in the wide range of temperature, i.e., 598-898 K for gas phase and 298-498 K for aqueous phase at a fixed pressure of 1 atm. The aqueous phase environment is created by SMD model using water as solvent. The thermochemical parameters using solvation model in the range of 298-498 K are more stable than gas phase for all reaction schemes. In addition, All reaction schemes in both phases are favourable at each temperature condition except the formation of phenol from vanillin via the formation of 5-formylsalicylaldehyde reported in the reaction schemes 7a and 7a1.

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Publication details

The article was accepted on 27 Jun 2017 and first published on 04 Jul 2017

Article type: Paper
DOI: 10.1039/C7NJ02004J
Citation: New J. Chem., 2017, Accepted Manuscript
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    Molecular modelling approach to elucidate the thermal decomposition routes of vanillin

    A. M. Verma and N. KISHORE, New J. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7NJ02004J

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