Analytical pyrolysis of lignin: Products stemming from [beta]-5 substructures Export

@article{citeulike:671234, abstract = {This paper addresses the behavior of [beta]-5 substructures in analytical pyrolysis of lignin. Five phenolic 2-arylcoumarans containing a [beta]-5 linkage, dehydrodiconiferyl alcohol (I) and II-V, and diazomethane-methylated I (Im), were pyrolyzed at 500 [deg]C for 4 s. The products were analyzed by gas chromatography and gas chromatography/mass spectrometry. The major products of I-IV and Im were 4-methylguaiacol (4) and 1,2-dimethoxy-4-methylbenzene (4m), respectively, stemming from the A moiety of the 2-arylcoumarans. 2-Arylcoumarans I-IV having the ring B with a CHCHCH2OH or CHCHCHO side chain provided 4 in a larger yield than dehydrodiisoeugenol (V) having the ring B with a CHCHCH3 side chain; the yields of 4 were \~{}6.6, 5.7-4.6, and 0.9 mol\% from I, II-IV and V, respectively. Characterization of the dimeric products of I showed the [alpha]-aryl ether opened-dimers with the hydrogenated C[alpha]-C[beta] bond being the precursors of 4. Based on these results, guaiacyl and syringyl [beta]-5 substructures were proposed as potential pyrolytic origins for 4 and 3,5-dimethoxy-4-methylphenol in analytical pyrolysis of soft- and hardwood lignins.}, author = {Kuroda, Ken-Ichi and Nakagawa-Izumi, Akiko}, citeulike-article-id = {671234}, citeulike-linkout-0 = {http://dx.doi.org/10.1016/j.orggeochem.2006.01.012}, citeulike-linkout-1 = {http://www.sciencedirect.com/science/article/B6V7P-4JTR959-4/2/3348418ab1611c257a7126e0d8c8bc02}, doi = {10.1016/j.orggeochem.2006.01.012}, journal = {Organic Geochemistry}, keywords = {gc-ms, lignin, purolysis}, month = {June}, number = {6}, pages = {665--673}, posted-at = {2006-05-26 12:51:09}, priority = {2}, title = {Analytical pyrolysis of lignin: Products stemming from [beta]-5 substructures}, url = {http://dx.doi.org/10.1016/j.orggeochem.2006.01.012}, volume = {37}, year = {2006} }

TY - JOUR ID - citeulike:671234 L3 - citeulike-article-id:671234 N2 - This paper addresses the behavior of [beta]-5 substructures in analytical pyrolysis of lignin. Five phenolic 2-arylcoumarans containing a [beta]-5 linkage, dehydrodiconiferyl alcohol (I) and II-V, and diazomethane-methylated I (Im), were pyrolyzed at 500 [deg]C for 4 s. The products were analyzed by gas chromatography and gas chromatography/mass spectrometry. The major products of I-IV and Im were 4-methylguaiacol (4) and 1,2-dimethoxy-4-methylbenzene (4m), respectively, stemming from the A moiety of the 2-arylcoumarans. 2-Arylcoumarans I-IV having the ring B with a CHCHCH2OH or CHCHCHO side chain provided 4 in a larger yield than dehydrodiisoeugenol (V) having the ring B with a CHCHCH3 side chain; the yields of 4 were ~6.6, 5.7-4.6, and 0.9 mol% from I, II-IV and V, respectively. Characterization of the dimeric products of I showed the [alpha]-aryl ether opened-dimers with the hydrogenated C[alpha]-C[beta] bond being the precursors of 4. Based on these results, guaiacyl and syringyl [beta]-5 substructures were proposed as potential pyrolytic origins for 4 and 3,5-dimethoxy-4-methylphenol in analytical pyrolysis of soft- and hardwood lignins. IS - 6 JF - Organic Geochemistry EP - 673 TI - Analytical pyrolysis of lignin: Products stemming from [beta]-5 substructures VL - 37 SP - 665 KW - gc-ms KW - lignin KW - purolysis AU - Kuroda, Ken-Ichi AU - Nakagawa-Izumi, Akiko PY - 2006/06// UR - http://dx.doi.org/10.1016/j.orggeochem.2006.01.012 ER -