Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 69, Issue 45, Pages 13568-13577Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.1c05759
Keywords
ether bond cleavage; lithium bromide; methoxyl; phenolic hydroxyl; radical scavenger
Funding
- National Natural Science Foundation of China [31890773, 32071718]
- Research Funds of Jiangsu Key Laboratory for Biomass Energy and Material [JSBEM-S-201803]
- Fundamental Research Funds of Research Institute of Forestry New Technology [CA-FYBB2019SZ007]
- USDA NIFA grant [2018-67009-27902]
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Under acidic lithium bromide trihydrate conditions, kraft lignin can be successfully depolymerized and demethylated, generating new aromatic hydroxyl groups and demonstrating excellent antioxidant activity and Cr(VI)-scavenging capacity.
To improve the reactivity and enrich the functionality of lignin for valorization, kraft lignin was depolymerized and demethylated via cleaving aryl and alkyl ether bonds in acidic lithium bromide trihydrate (similar to 60% LiBr aqueous solution). It was found that the cleavage of the ether bonds followed the order of beta-O-4 ether > aryl alkyl ether in phenylcoumaran > dialkyl ether in resinol > methoxyl (MeO). The depolymerization via beta-O-4 cleavage occurred under mild conditions (e.g., <0.5 M HCl at 110 degrees C), while sufficient demethylation of the lignin needed harsher conditions (>1.5 M HCl). Both depolymerization and demethylation generated new aromatic hydroxyl (ArOH). With 2.4 M HCl, MeO content dropped from 4.85 to 0.95 mmol/g lignin, and ArOH content increased from 2.78 to 5.09 mmol/g lignin. The depolymerized and demethylated kraft lignin showed excellent antioxidant activity and Cr(VI)-scavenging capacity, compared with original kraft lignin and tannins.
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