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Tetrazole ethers from lignin model phenols: synthesis, crystal structures, and photostability

TitleTetrazole ethers from lignin model phenols: synthesis, crystal structures, and photostability
Publication TypeJournal Article
Year of Publication2001
AuthorsLu, AZ, Hu, TQ, Osmond, DA, Patrick, BO, James, BR
JournalCanadian Journal of Chemistry-Revue Canadienne De Chimie
Volume79
Pagination1201-1206
Date PublishedAug
Type of ArticleArticle
ISBN Number0008-4042
KeywordsALKYLATION, ETHERS, HIGH-YIELD PULPS, LIGHT, LIGNIN MODEL COMPOUNDS, METHYLATION, PHENOLS, yellowing inhibition
Abstract

{The phenolic OH moiety in lignin is one of the key functional groups responsible for the photo-induced yellowing of mechanical wood pulps and papers. To evaluate new protective groups for the stabilization of lignin phenols, the model compounds, 2-methoxy-4-propylphenol (1) and 4-hydroxy-3-methoxyacetophenone (2) were reacted with 5-chloro-1-phenyl-1H-tetrazole to give the corresponding tetrazole ethers 1’ and 2’, respectively, that were then studied for their photostability. The synthesis of these ethers was more efficient than that of alkyl ethers because of less hydrolysis of the alkylating agent under the reaction conditions. Compounds 1’ and 2’ were fully characterized, including X-ray crystal structure analyses. Crystals of 1’ and 2’ were monoclinic of space groups P2(1)/c and P2(1)/a, respectively. For 1’: a = 9.8679(6)

URL<Go to ISI>://000171071400001