Antioxidant properties of phenolic lignin model compounds
Antioxidant activities of phenolic lignin model compounds were determined by measurements of inhibition rate constants (kinh) during inhibited peroxidation of styrene in chlorobenzene initiated by azobisisobutyrylnitrile with known rates of initiation (Ri). The number of peroxyl radicals trapped by...
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Veröffentlicht in: | Journal of wood chemistry and technology 1997-01, Vol.17 (1/2), p.73-90 |
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description | Antioxidant activities of phenolic lignin model compounds were determined by measurements of inhibition rate constants (kinh) during inhibited peroxidation of styrene in chlorobenzene initiated by azobisisobutyrylnitrile with known rates of initiation (Ri). The number of peroxyl radicals trapped by each antioxidant, stoichiometric factors (n), were determined by comparison with pentamethyl-hydroxychroman, PMHC, n = 2. Monomeric lignin models, 4-propylguaiacol (1), eugenol (2), isoeugenol (3), coniferyl alcohol (4), coniferyl aldehyde (5), and 4-allyl-2,6-dimethoxyphenol (6) were all more active antioxidants than the commercial inhibitor 2,6-di-tert-butyl-4-methylphenol (BHT). Two dimer models, bis(2-hydroxy-3-methoxyl-5-allylphenyl),methane (7) and 2,2'-dihydroxy-3,3'-dimethoxy-5,5'-dimethoxymethylbiphenyl (8) and a synthetic tetramer, bis[2-hydroxy-5-(2'-hydroxy-3'-methoxy-5'-methylbenzyl)-3- methoxyphenyl]methane (9) were more active antioxidants. The overall relative activity was tetramer dimers monomers BHT. The stoichiometric factors of 1 to 6 ranged from 1.6 to 1.7 compared to PMHC. The n factors for 7, 8, and 9, showed an additive effect per phenolic hydroxyl. Phenolic groups in lignin may protect lignin-containing pulps and paper against damaging free radical peroxidation |
doi_str_mv | 10.1080/02773819708003119 |
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(Mount Allison University, Sackville, NB, Canada.) ; Xi, F ; Norris, J.Q</creator><creatorcontrib>Barclay, L.R.C. (Mount Allison University, Sackville, NB, Canada.) ; Xi, F ; Norris, J.Q</creatorcontrib><description>Antioxidant activities of phenolic lignin model compounds were determined by measurements of inhibition rate constants (kinh) during inhibited peroxidation of styrene in chlorobenzene initiated by azobisisobutyrylnitrile with known rates of initiation (Ri). The number of peroxyl radicals trapped by each antioxidant, stoichiometric factors (n), were determined by comparison with pentamethyl-hydroxychroman, PMHC, n = 2. Monomeric lignin models, 4-propylguaiacol (1), eugenol (2), isoeugenol (3), coniferyl alcohol (4), coniferyl aldehyde (5), and 4-allyl-2,6-dimethoxyphenol (6) were all more active antioxidants than the commercial inhibitor 2,6-di-tert-butyl-4-methylphenol (BHT). Two dimer models, bis(2-hydroxy-3-methoxyl-5-allylphenyl),methane (7) and 2,2'-dihydroxy-3,3'-dimethoxy-5,5'-dimethoxymethylbiphenyl (8) and a synthetic tetramer, bis[2-hydroxy-5-(2'-hydroxy-3'-methoxy-5'-methylbenzyl)-3- methoxyphenyl]methane (9) were more active antioxidants. The overall relative activity was tetramer dimers monomers BHT. The stoichiometric factors of 1 to 6 ranged from 1.6 to 1.7 compared to PMHC. The n factors for 7, 8, and 9, showed an additive effect per phenolic hydroxyl. 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Non wovens</subject><ispartof>Journal of wood chemistry and technology, 1997-01, Vol.17 (1/2), p.73-90</ispartof><rights>Copyright Taylor & Francis Group, LLC 1997</rights><rights>1997 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c395t-f3b50e6ae89114fff91014666923783f74169ff5e65bae488272f2fea213040e3</citedby><cites>FETCH-LOGICAL-c395t-f3b50e6ae89114fff91014666923783f74169ff5e65bae488272f2fea213040e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.1080/02773819708003119$$EPDF$$P50$$Ginformaworld$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.1080/02773819708003119$$EHTML$$P50$$Ginformaworld$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,59647,60436</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2715414$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Barclay, L.R.C. (Mount Allison University, Sackville, NB, Canada.)</creatorcontrib><creatorcontrib>Xi, F</creatorcontrib><creatorcontrib>Norris, J.Q</creatorcontrib><title>Antioxidant properties of phenolic lignin model compounds</title><title>Journal of wood chemistry and technology</title><description>Antioxidant activities of phenolic lignin model compounds were determined by measurements of inhibition rate constants (kinh) during inhibited peroxidation of styrene in chlorobenzene initiated by azobisisobutyrylnitrile with known rates of initiation (Ri). The number of peroxyl radicals trapped by each antioxidant, stoichiometric factors (n), were determined by comparison with pentamethyl-hydroxychroman, PMHC, n = 2. Monomeric lignin models, 4-propylguaiacol (1), eugenol (2), isoeugenol (3), coniferyl alcohol (4), coniferyl aldehyde (5), and 4-allyl-2,6-dimethoxyphenol (6) were all more active antioxidants than the commercial inhibitor 2,6-di-tert-butyl-4-methylphenol (BHT). Two dimer models, bis(2-hydroxy-3-methoxyl-5-allylphenyl),methane (7) and 2,2'-dihydroxy-3,3'-dimethoxy-5,5'-dimethoxymethylbiphenyl (8) and a synthetic tetramer, bis[2-hydroxy-5-(2'-hydroxy-3'-methoxy-5'-methylbenzyl)-3- methoxyphenyl]methane (9) were more active antioxidants. The overall relative activity was tetramer dimers monomers BHT. The stoichiometric factors of 1 to 6 ranged from 1.6 to 1.7 compared to PMHC. The n factors for 7, 8, and 9, showed an additive effect per phenolic hydroxyl. Phenolic groups in lignin may protect lignin-containing pulps and paper against damaging free radical peroxidation</description><subject>ANTIOXIDANTES</subject><subject>ANTIOXIDANTS</subject><subject>ANTIOXYDANT</subject><subject>Applied sciences</subject><subject>COMPOSE PHENOLIQUE</subject><subject>COMPUESTOS FENOLICOS</subject><subject>Exact sciences and technology</subject><subject>LIGNINAS</subject><subject>LIGNINE</subject><subject>LIGNINS</subject><subject>MODELE</subject><subject>MODELOS</subject><subject>Paper, paperboard, non wovens</subject><subject>PASTA</subject><subject>PATE CELLULOSIQUE</subject><subject>PHENOLIC COMPOUNDS</subject><subject>Polymer industry, paints, wood</subject><subject>Properties and testing</subject><subject>PULP</subject><subject>Wood. Paper. 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(Mount Allison University, Sackville, NB, Canada.)</creator><creator>Xi, F</creator><creator>Norris, J.Q</creator><general>Taylor & Francis Group</general><general>Taylor & Francis</general><scope>FBQ</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19970101</creationdate><title>Antioxidant properties of phenolic lignin model compounds</title><author>Barclay, L.R.C. (Mount Allison University, Sackville, NB, Canada.) ; Xi, F ; Norris, J.Q</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c395t-f3b50e6ae89114fff91014666923783f74169ff5e65bae488272f2fea213040e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><topic>ANTIOXIDANTES</topic><topic>ANTIOXIDANTS</topic><topic>ANTIOXYDANT</topic><topic>Applied sciences</topic><topic>COMPOSE PHENOLIQUE</topic><topic>COMPUESTOS FENOLICOS</topic><topic>Exact sciences and technology</topic><topic>LIGNINAS</topic><topic>LIGNINE</topic><topic>LIGNINS</topic><topic>MODELE</topic><topic>MODELOS</topic><topic>Paper, paperboard, non wovens</topic><topic>PASTA</topic><topic>PATE CELLULOSIQUE</topic><topic>PHENOLIC COMPOUNDS</topic><topic>Polymer industry, paints, wood</topic><topic>Properties and testing</topic><topic>PULP</topic><topic>Wood. Paper. Non wovens</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Barclay, L.R.C. (Mount Allison University, Sackville, NB, Canada.)</creatorcontrib><creatorcontrib>Xi, F</creatorcontrib><creatorcontrib>Norris, J.Q</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Journal of wood chemistry and technology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Barclay, L.R.C. (Mount Allison University, Sackville, NB, Canada.)</au><au>Xi, F</au><au>Norris, J.Q</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antioxidant properties of phenolic lignin model compounds</atitle><jtitle>Journal of wood chemistry and technology</jtitle><date>1997-01-01</date><risdate>1997</risdate><volume>17</volume><issue>1/2</issue><spage>73</spage><epage>90</epage><pages>73-90</pages><issn>0277-3813</issn><eissn>1532-2319</eissn><coden>JWCTDJ</coden><abstract>Antioxidant activities of phenolic lignin model compounds were determined by measurements of inhibition rate constants (kinh) during inhibited peroxidation of styrene in chlorobenzene initiated by azobisisobutyrylnitrile with known rates of initiation (Ri). The number of peroxyl radicals trapped by each antioxidant, stoichiometric factors (n), were determined by comparison with pentamethyl-hydroxychroman, PMHC, n = 2. Monomeric lignin models, 4-propylguaiacol (1), eugenol (2), isoeugenol (3), coniferyl alcohol (4), coniferyl aldehyde (5), and 4-allyl-2,6-dimethoxyphenol (6) were all more active antioxidants than the commercial inhibitor 2,6-di-tert-butyl-4-methylphenol (BHT). Two dimer models, bis(2-hydroxy-3-methoxyl-5-allylphenyl),methane (7) and 2,2'-dihydroxy-3,3'-dimethoxy-5,5'-dimethoxymethylbiphenyl (8) and a synthetic tetramer, bis[2-hydroxy-5-(2'-hydroxy-3'-methoxy-5'-methylbenzyl)-3- methoxyphenyl]methane (9) were more active antioxidants. The overall relative activity was tetramer dimers monomers BHT. The stoichiometric factors of 1 to 6 ranged from 1.6 to 1.7 compared to PMHC. The n factors for 7, 8, and 9, showed an additive effect per phenolic hydroxyl. Phenolic groups in lignin may protect lignin-containing pulps and paper against damaging free radical peroxidation</abstract><cop>Colchester</cop><pub>Taylor & Francis Group</pub><doi>10.1080/02773819708003119</doi><tpages>18</tpages></addata></record> |
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subjects | ANTIOXIDANTES ANTIOXIDANTS ANTIOXYDANT Applied sciences COMPOSE PHENOLIQUE COMPUESTOS FENOLICOS Exact sciences and technology LIGNINAS LIGNINE LIGNINS MODELE MODELOS Paper, paperboard, non wovens PASTA PATE CELLULOSIQUE PHENOLIC COMPOUNDS Polymer industry, paints, wood Properties and testing PULP Wood. Paper. Non wovens |
title | Antioxidant properties of phenolic lignin model compounds |
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