@article {LIAO2024129677, title = {Eco-friendly regeneration of lignin with acidic deep eutectic solvent for adsorption of pollutant dyes for water cleanup}, journal = {International Journal of Biological Macromolecules}, volume = {260}, year = {2024}, pages = {129677}, abstract = {In this study, a simple and eco-friendly method was used to treat alkaline lignin with an acidic deep eutectic solvent (DES) to obtain regenerated lignin for the efficient adsorption of pollutant dyes from aqueous environment. Based on the yield and adsorption capacity of the sorbent for these dyes, conditions such as the type and concentration of DES component, solid-to-liquid ratio, reaction time, and temperature were optimized. By characterizing and comparing alkali lignin with regenerated lignin, a series of reactions were demonstrated to occur during the DES treatment process. The performance and mechanism of methylene blue and rhodamine B adsorption on regenerated lignin were studied systematically, and the maximum adsorbed amounts were 348.29 and 551.05~mg/g at 323~K, respectively. This study provides a new strategy for the green preparation of functionalized lignin and its use in the water pollutant treatment.}, keywords = {Deep eutectic solvent, Green regeneration of lignin, LIGNIN, Pollutant adsorption}, issn = {0141-8130}, doi = {https://doi.org/10.1016/j.ijbiomac.2024.129677}, url = {https://www.sciencedirect.com/science/article/pii/S014181302400480X}, author = {Yuqing Liao and Wuxia Ge and Min Liu and Wentao Bi and Can Jin and David Da Yong Chen} } @article {2537, title = {Reactions of Tertiary Phosphines with Alcohols in Aqueous Media}, journal = {Inorganic Chemistry}, volume = {48}, number = {1}, year = {2009}, note = {ISI Document Delivery No.: 388HUTimes Cited: 4Cited Reference Count: 29Moiseev, Dmitry V. Patrick, Brian O. James, Brian R.}, month = {Jan}, pages = {239-245}, type = {Article}, abstract = {The phosphines R2R{\textquoteright}P [R = R{\textquoteright} = Me, Et, Pr-n, Pr-i, (CH2)(3)OH; Me2PhP and MePh2P] react with 2- or 4-hydroxybenzyl alcohols, including "lignin-type" vanillyl, syringyl, and alpha-methylvanillyl alcohols, in a 1:1 ratio in aqueous media, to give zwitterionic phosphobetaine products; these on treatment with aq HCl form the corresponding phosphonium chlorides in good to excellent yields. The syringyl derivative [3,5-(OMe)(2)-4-OH-C6H2CH2PEt3]Cl was structurally characterized by X-ray analysis. Kinetically, the reactivity of the benzyl alcohols, studied with the water-soluble [HO(CH2)(3)](3)P, decreases with substituents in the order 2-hydroxy > 4-hydroxy > vanillyl > syringyl > alpha-methylvanillyl, while 3-hydroxybenzyl alcohol is unreactive; the trend is consistent with reactivity requiring the presence of an ortho- or para-OH substituent in the aromatic ring of the alcohol, and that the reactions proceed via a carbocation species stabilized as a quinone methide. Triethylphosphine reacts with coniferyl alcohol at the C=C moiety to give a zwitterionic intermediate that is again converted by aq HCl to a phosphonium chloride; no reaction was observed with cinnamyl alcohol. The effect on a phenolic pK(a) by incorporation of a phosphonium substituent is also measured.}, keywords = {ALDEHYDES, BENZYL, FACILE SYNTHESIS, LIGNIN, PHOSPHONIUM SALTS, QUINONE METHIDE}, isbn = {0020-1669}, url = {://000262011700032}, author = {Moiseev, D. V. and Patrick, B. O. and James, Brian R.} } @article {2536, title = {Reversible decomposition of mono(alpha-hydroxy)phosphines and their reaction with alpha,beta-unsaturated aldehydes}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {87}, number = {4}, year = {2009}, note = {ISI Document Delivery No.: 431IGTimes Cited: 4Cited Reference Count: 24Moiseev, Dmitry V. Marcazzan, Paolo James, Brian R.}, month = {Apr}, pages = {582-590}, type = {Article}, abstract = {{The mono (alpha-hydroxy) phosphines R2PCH(OH)R{\textquoteright} (R = Ph, R{\textquoteright} = H, Et, CH2Ph, Ph, p-X-C6H4; R = cyclohexyl, R{\textquoteright} = Ph) are prepared under solvent-free conditions by a 1:1 reaction of Ph2PH with the appropriate aldehyde, and their stabilities (with respect to reversible dissociation into reactants), studied in DMSO, Et2O, and MeOH, increase with decreased basicity of the hydroxyphosphine; for example, for the Ph2PCH (OH) C6H4-p-X phosphines, stability decreases in the order:X = CN > Cl > F > H > Me > OMe. A 1:1 room-temperature reaction of the (alpha-hydroxy) phosphines (except for R{\textquoteright} = H) with cinnamaldehyde in DMSO slowly yields the known mono-and di-phosphines Ph2PCH(Ph)CH2CHO (4a) and Ph2PCH(Ph)CH2CH(PPh2)OH (10a), and the corresponding R{\textquoteright}CHO aldehyde. In MeOH, the sequentially formed intermediates}, keywords = {(alpha-hydroxy)phosphines, alpha, beta-unsaturated aldehydes, CHEMISTRY, CHLORIDE, diphenylphosphine, FORMALDEHYDE, hydrophosphination, LIGNIN, NUCLEAR MAGNETIC-RESONANCE, PHOSPHONIUM CHLORIDE, TERTIARY PHOSPHINES, TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM, TRIS(HYDROXYMETHYL)PHOSPHINE, WATER}, isbn = {0008-4042}, url = {://000265054200007}, author = {Moiseev, D. V. and Marcazzan, P. and James, Brian R.} } @article {4385, title = {(13)CPMAS-NMR spectroscopy and chemical analysis of coarse woody debris in coastal forests of Vancouver Island}, journal = {Forest Ecology and Management}, volume = {111}, number = {1}, year = {1998}, note = {ISI Document Delivery No.: 137DZTimes Cited: 46Cited Reference Count: 52}, month = {Nov}, pages = {51-68}, type = {Article}, abstract = {The coastal forests of British Columbia have large accumulations of coarse woody debris, and information on this pool is considered essential in developing sustainable management practices. We characterized coarse woody debris (7-12 and >12 cm diameter) in forest chronosequences of four age classes located on the eastern and western sides of Vancouver Island. For three species (Douglas-fir (Pseudotsuga menziesii (Mirb.) France), western hemlock (Tsuga heterophylla (Raf.) Sarg), western red cedar (Thuja plicata Donn.)) and unidentified samples, increases in decay class (I to V, assigned in the field) were associated with decreasing density, and small increases in concentrations of C, N, and P. Sulfur concentrations (0.6-2.4 g/kg) were higher than those found elsewhere for wood and did not show any significant changes with decay class. C-13 nuclear magnetic resonance spectroscopy with cross polarization and magic-angle spinning (C-13-CPMAS-NMR) was used to analyze organic components in a subset of samples >12 cm. Logs up to decay class III generally showed little change in composition or a slight increase in polysaccharide C. After this, polysaccharide was lost more quickly and logs of decay class V were composed almost entirely of lignin, a pattern consistent with decay by brown-rot fungi. However, two samples of western red cedar decay class III and IV showed accumulation of polysaccharide, the pattern expected from white-rot fungi. The results of the density, chemical and NMR analysis indicate that for management purposes, a system with fewer decay classes would suffice. (C) 1998 Elsevier Science B.V.}, keywords = {BRITISH-COLUMBIA, brown-rot, chronosequence, COLORADO BLUE SPRUCE, cross polarization, CUO OXIDATION, DECOMPOSITION, DOUGLAS-FIR FORESTS, LIGNIN, NUCLEAR-MAGNETIC-RESONANCE, NUTRIENT CONTENT, SOLID-STATE NMR, SULFUR, WESTERN OREGON, white-rot, WHITE-ROT DECAY}, isbn = {0378-1127}, url = {://000076900700005}, author = {Preston, C. M. and Trofymow, J. A. and Niu, J. and Fyfe, C. A.} } @article {4001, title = {Towards inhibition of yellowing of mechanical pulps .2. Water-soluble catalysts for the hydrogenation of lignin model compounds}, journal = {Journal of Pulp and Paper Science}, volume = {23}, number = {5}, year = {1997}, note = {ISI Document Delivery No.: WY102Times Cited: 18Cited Reference Count: 32}, month = {May}, pages = {J200-J205}, type = {Article}, abstract = {Water-soluble, polymer-stabilized, colloidal rhodium is an effective catalyst for the hydrogenation of the aromatic rings of the lignin model compounds 4-propylphenol, 2-methoxy-4-propylphenol, and 1,2-dimethoxy-4-propylbenzene under extremely mild conditions (25 degrees C, 1 atm H-2) in a one-phase, aqueous ethanol medium. The water-soluble catalyst is prepared by reducing rhodium trichloride trihydrate with ethanol in the presence of polyvinylpyrrolidone (PVP) and triethylamine, The reactivity of various chromophore precursors in lignin toward hydrogenation catalyzed by water-soluble, colloidal rhodium follows the descending order of carbon-carbon double bond > aromatic ring in 4-propylphenol > carbonyl group and the aromatic rings in 2-methoxy-4-propylphenol and 1,2-dimethoxy-4-propylbenzene, The hydrogenation of 2-methoxy-4-propylphenol and 1,2-dimethoxy-4-propylbenzene is accompanied by some hydrogenolysis and removal of the OMe group.}, keywords = {aromatic compounds, aromatic groups, CARBON-MONOXIDE, CARBONYL, CATALYSTS, CHROMOPHORES, CLUSTERS, colloids, GROUPS, HIGH-YIELD PULPS, HYDROGENATION, HYDROGENOLYSIS, INHIBITION, LIGNIN, mechanical pulps, model compounds, water solubles, yellowing}, isbn = {0826-6220}, url = {://A1997WY10200002}, author = {Hu, Thomas Q. and James, Brian R. and Lee, C. L.} } @article {4001, title = {Towards inhibition of yellowing of mechanical pulps .2. Water-soluble catalysts for the hydrogenation of lignin model compounds}, journal = {Journal of Pulp and Paper Science}, volume = {23}, number = {5}, year = {1997}, note = {ISI Document Delivery No.: WY102Times Cited: 18Cited Reference Count: 32}, month = {May}, pages = {J200-J205}, type = {Article}, abstract = {Water-soluble, polymer-stabilized, colloidal rhodium is an effective catalyst for the hydrogenation of the aromatic rings of the lignin model compounds 4-propylphenol, 2-methoxy-4-propylphenol, and 1,2-dimethoxy-4-propylbenzene under extremely mild conditions (25 degrees C, 1 atm H-2) in a one-phase, aqueous ethanol medium. The water-soluble catalyst is prepared by reducing rhodium trichloride trihydrate with ethanol in the presence of polyvinylpyrrolidone (PVP) and triethylamine, The reactivity of various chromophore precursors in lignin toward hydrogenation catalyzed by water-soluble, colloidal rhodium follows the descending order of carbon-carbon double bond > aromatic ring in 4-propylphenol > carbonyl group and the aromatic rings in 2-methoxy-4-propylphenol and 1,2-dimethoxy-4-propylbenzene, The hydrogenation of 2-methoxy-4-propylphenol and 1,2-dimethoxy-4-propylbenzene is accompanied by some hydrogenolysis and removal of the OMe group.}, keywords = {aromatic compounds, aromatic groups, CARBON-MONOXIDE, CARBONYL, CATALYSTS, CHROMOPHORES, CLUSTERS, colloids, GROUPS, HIGH-YIELD PULPS, HYDROGENATION, HYDROGENOLYSIS, INHIBITION, LIGNIN, mechanical pulps, model compounds, water solubles, yellowing}, isbn = {0826-6220}, url = {://A1997WY10200002}, author = {Hu, Thomas Q. and James, Brian R. and Lee, C. L.} } @article {3287, title = {Iron porphyrin catalyzed oxidation of lignin model compounds: Oxidation of phenylpropane and phenylpropene model compounds}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {73}, number = {12}, year = {1995}, note = {ISI Document Delivery No.: TV232Times Cited: 4Cited Reference Count: 41}, month = {Dec}, pages = {2153-2157}, type = {Article}, abstract = {The oxidation of 1-(4-ethoxy-3-methoxyphenyl)propane (2) and 1-(4-ethoxy-3-methoxyphenyl)propene (3) by meso-tetra(2,6-dichloro-3-sulphonatophe)porphyrin iron chloride (TDCSPPFeCl, 1) and tert-butylhydroperoxide (t-BuOOH) are discussed. In addition to a C-alpha-hydroxylation product, demethoxylation and direct aromatic ring cleavage products were found in the oxidation of 2. When 3 was oxidized by 1 and t-BuOOH in aqueous acetonitrile, an acetonitrile-incorporated product was found. A mechanism for the oxidation of 3 is proposed.}, keywords = {AROMATIC RING CLEAVAGE, BASIDIOMYCETE PHANEROCHAETE-CHRYSOSPORIUM, C BOND-CLEAVAGE, CHARACTERIZATION, DEGRADATION, DEGRADING ENZYME, DIARYLPROPANE, HEME-ENZYME, iron porphyrin, LIGNIN, ligninase, MODEL, OXYGENASE, POTASSIUM MONOPERSULFATE, SPECTRAL, VERATRYL ALCOHOL, WHITE ROT BASIDIOMYCETE}, isbn = {0008-4042}, url = {://A1995TV23200008}, author = {Cui, F. and Dolphin, D.} } @article {2912, title = {X-RAY PHOTOELECTRON SPECTROSCOPIC ANALYSIS OF CCA-TREATED WOOD}, journal = {Holzforschung}, volume = {47}, number = {6}, year = {1993}, note = {ISI Document Delivery No.: ML941Times Cited: 17Cited Reference Count: 25}, pages = {458-464}, type = {Article}, abstract = {Ponderosa pine and Douglas-fir wood sections were treated with CCA preservative. To elucidate the mechanism of fixation of the CCA, the wood surface was analyzed by X-ray photoelectron spectroscopy (XPS). CCA treatment increased C1 (carbon bonded to carbon and/or hydrogen) and decreased C2 (carbon bonded to one oxygen) in XPS C1s spectra, in both unextracted and pre-extracted sections. This suggested oxidation of hydroxyl groups on cellulose and/or lignin by CCA occurred, followed by the decarboxylation of carbonyl and carboxyl groups. However, the large changes in the state of the carbon atoms recorded during CCA treatment of unextracted wood would appear to include combined effects of the migration of extractives to analyzed surfaces as well as the oxidation of hydroxyl groups in wood by CCA. Accelerating the fixation produced more C1 than fixation at ambient temperatures. This increase in C1 also correlated with a higher resistance to preservative leaching in wood in which the CCA was fixed under accelerating conditions. Surface concentrations of the CCA components determined by XPS were lower in wood in which the fixation was accelerated, and this may contribute to their lower water repellency. CCA treatment enhanced the water repellency of wood, especially in the presence of extractives.}, keywords = {CCA PRESERVATIVES, CHROMATED COPPER ARSENATE, ESCA ANALYSIS, FIXATION, LEACHING, LIGNIN, photoelectron spectroscopy, PINUS-PONDEROSA, PSEUDOTSUGA-MENZIESII, SURFACES, WATER REPELLENCY, X-RAY, XPS}, isbn = {0018-3830}, url = {://A1993ML94100002}, author = {Ruddick, J. N. R. and Yamamoto, K. and Wong, P. C. and Mitchell, K. A. R.} } @article {6996, title = {VERATRYL ALCOHOL AS A MEDIATOR IN LIGNIN MODEL-COMPOUND BIODEGRADATION}, journal = {Holzforschung}, volume = {45}, number = {1}, year = {1991}, note = {ISI Document Delivery No.: FC210Times Cited: 7Cited Reference Count: 22}, month = {Feb}, pages = {31-35}, type = {Article}, abstract = {Veratryl alcohol and 1,4-dimethoxybenzene were found to be ineffective mediators for the oxidation of anisyl alcohol by the lignin peroxidase model, iron meso-tetra(2,6-dichloro-3-sulfonatophenyl)porphyrin chloride (TDCSPPFeCl). However, veratryl alcohol can mediate the electrochemical oxidation of the polymeric dye Poly B-411. The TDCSPPFeCl catalyzed reactions of lignin model compounds were found to be dependent on pH and the solvent being used. The importance of the mediating role of veratryl alcohol in lignin degradation is discussed.}, keywords = {APPROACH, BASIDIOMYCETE PHANEROCHAETE-CHRYSOSPORIUM, BIOMIMETIC, BURDS, C BOND-CLEAVAGE, DEGRADATION, ENZYME, IRON PORPHYRINS, LIGNIN, MECHANISM, MEDIATOR, OXIDATION, PEROXIDASE, PORPHYRIN, SYSTEM, VERATRYL ALCOHOL}, isbn = {0018-3830}, url = {://A1991FC21000006}, author = {Cui, F. T. and Dolphin, D.} }