Subcritical water hydrolysis of N-acetyl-D-glucosamine: hydrolysis mechanism, reaction pathways and optimization for selective production of 5-HMF and levulinic acid

TitleSubcritical water hydrolysis of N-acetyl-D-glucosamine: hydrolysis mechanism, reaction pathways and optimization for selective production of 5-HMF and levulinic acid
Publication TypeJournal Article
Year of Publication2022
AuthorsKulkarni, SPrakash, Dure, SN, Joshi, SS, Pandare, KV, Mali, NA
JournalCarbohydrate Research
Volume516
Pagination108560
Date PublishedJUN
Type of ArticleArticle
ISSN0008-6215
Keywords5-Hydroxymethylfurfural, chitin, Glucosamine, levulinic acid, Response surface methodology, Subcritical water
Abstract

In this study, the subcritical water hydrolysis of N-acetyl-D-glucosamine (NAG), a monomer of abundant renewable marine biopolymer chitin, for production of value-added chemicals is investigated. The enhanced ionization of water at subcritical conditions (200 degrees C; 50-100 bar), provides enough acidity for deacetylation of NAG resulting in 80% yield of acetic acid along with traces of formic acid, lactic acid, glucose, fructose, 5hydroxymethylfurfural (5-HMF),etc. The significant humin formation indicates that the self-condensation and polymerisation of 5-HMF is favored in water at subcritical conditions. A catalyst p-toluenesulfonic acid (p-TsOH) was employed to selectively convert NAG to levulinic acid (LA) via ring opening of 5-HMF previously formed during hydrolysis. The maximum yield of 27.13 +/- 1% and 53.46 +/- 1% of 5-HMF and LA, respectively, was obtained at process conditions optimized using Box-Behnken design coupled with response surface methodology. Subcritical water enables greener conversion of NAG to platform chemicals wherein the selective production can be achieved by tuning the process conditions.

DOI10.1016/j.carres.2022.108560
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.975

Divison category: 
Chemical Engineering & Process Development
Polymer Science & Engineering
Database: 
Web of Science (WoS)

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