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Stereoselective Reactions and Applications in Organic Synthesis

Abstract

Size exclusion chromatography with multi-angle laser light-scattering detectors was applied for acetylated softwood and hardwood kraft lignins (Ac-SKL and Ac-HKL) and 8-O-4′ type of linear polymeric lignin model (Ac-M-8O4′) to compare their swelling behaviors. The plot of molar mass (MM) vs. retention time for Ac-M-8O4′ was similar to that of polystyrene, which revealed that Ac-M-8O4′ exhibited swelling behavior that was similar to that of polystyrene. However, the MM values of both Ac-KLs were larger than those of polystyrene standards at any retention time. This difference indicated that both Ac-KLs had a more compact structure than those of polystyrene and Ac-M-8O4′. One hypothesis is that the larger MM of both Ac-KLs stems from their branched structures. To verify this hypothesis, the frequency of 5-5′ interunit linkage in lignin samples was determined by 1H NMR after nitrobenzene oxidation. A linear relationship between MM and 5-5′ abundance was observed in the high MM region.

Abstract

Wood decay is an economically significant process, as it is one of the major causes of wood deterioration in buildings. In this study, the decay process of Scots pine (Pinus sylvestris) samples caused by cellar fungus (Coniophora puteana) was followed by nuclear magnetic resonance (NMR) spectroscopy and magnetic resonance imaging (MRI) methods. Altogether, 30 wood sample pieces were exposed to fungus for 10 weeks. Based on the decrease of the dry mass, the samples were categorized into three classes: decomposed (mass decrease 50–70%), slightly decomposed (10–50%), and nondecomposed (<10%). MRI made it possible to identify the active regions of fungus inside the wood samples based on the signal of free water brought by the fungus and arisen from the decomposition of wood carbohydrates. MRI implies that free water is not only created by the decay process, but fungal hyphae also transports a significant amount of water into the sample. Two-dimensional 1H T 1-T 2 relaxation correlation NMR measurements provided detailed information about the changes in the microstructure of wood due to fungal decomposition. Overall, this study paves the way for noninvasive NMR and MRI detection of fungal decay at early stages as well as the related structural changes.

Abstract

Trees with high levels of growth stress begin to show log end splits (LES) immediately after harvesting, usually reaching its maximum end split in a week, and these tensions also create splits during lumber manufacturing. Interlocked grain is another characteristic that impacts the properties of eucalyptus wood. The aim of this study was to evaluate the effect of growth stress and interlocked grain patterns on log end splitting of seven different hybrid clones of Eucalyptus grandis × Eucalyptus urophylla planted in Brazil. The growth stress indicator (GSI) was measured in standing trees before harvesting. Splits were measured on logs in three different stages, and interlocked grain from wood blocks was obtained across the center of the cross-section. The results showed that LES occurred as soon as the trees were harvested; however, for better selection of clones, LES should be evaluated after a week of harvesting. There were statistically significant correlations for GSI with LES. Clones that presented higher values of interlocked grain tended to develop lower values of GSI and LES. Using GSI and interlocked grain measurements, it was possible to select the most indicated eucalyptus clones for lumber production.

Abstract

This paper deals with an original and non-biocidal chemical treatment consisting of a vacuum/pressure impregnation step of beech wood with a water-borne mixture made from heat-activated condensation of succinic anhydride (SA) and glycerol (G). Chemical structures of adducts were established using matrix-assisted laser desorption ionization time-of-flight mass spectroscopy (MALDI-TOF) investigations. Beech wood was impregnated and cured in order to induce in situ polymerization of glycerol/succinic adducts (GSA) in the cell walls, leading to the formation of polyglycerol succinate (PGS) polyester. Various treatment conditions were investigated depending on the duration (6–72 h) and curing temperature (103–160°C). Weight percent gains (WPGs) ranging between 40 and 60% were obtained. Attenuated total reflectance-middle infrared spectroscopy (ATR-MIR) and carbon-13 nuclear magnetic resonance (13C-NMR) spectroscopy confirmed polyester formation. A curing temperature of 160°C was found to be the best condition to totally avoid polymer leaching, and brought the anti-swelling efficiency (ASE) up to 64%. Decay resistance of PGS-treated wood against Trametes versicolor and Coniophora puteana was also strongly temperature and time dependent: performances fit with the EN113 standard requirements if a curing temperature of 160°C was applied.

Abstract

The aim of this study was to investigate Rhodonia placenta expression patterns of genes involved in the depolymerisation during the non-enzymatic phase in acetylated (WAc) and furfurylated wood (WFA). During the 98-day-long exposure, WAc [22.6% weight per cent gain (WPG) on average] and WFA (69% WPG on average) lost no more than 3% mass while the untreated wood (WUn) reached 41% mass loss (ML) in 55 days. Expression of six genes putatively involved in the non-enzymatic degradation process were investigated. In conclusion, expression levels of alcohol oxidase Ppl118723 (AlOx1) and laccase Ppl111314 (Lac) were significantly higher in the modified wood materials (WMod) than in WUn, which is in accordance with previous results and may be explained by the absence of the degradation products that have been proposed to down-regulate the non-enzymatic degradation process. However, copper radical oxidase Ppl156703 (CRO1) and a putative quinate transporter Ppl44553 (PQT) were expressed at significantly lower levels in WMod than in WUn while quinone reductase Ppl124517 (QRD) and glucose oxidase Ppl108489 (GOx) were expressed at similar levels as in WUn. These results suggest that gene regulation in WMod is more complex than a general up-regulation of genes involved in the non-enzymatic degradation phase.

Abstract

This study investigated several key parameters of deuterium exchange measurements in a dynamic vapour sorption apparatus to optimise the measurement protocol for hydroxyl (OH) group accessibility determination. The impact of changing the sample mass, the deuterium oxide (D2O) vapour exposure time and the rate of change in moisture content (dm dt−1) during the drying steps on the measured OH group accessibility were analysed. A sample mass of more than 10 mg, an exposure to D2O vapour of at least 10 h and a dm dt−1 of 0.0005% min−1 over a 10-min period during the drying steps gave the most reliable results. We also investigated the necessity of adding a method stage that eliminates the effect of inclusion compounds (ICs). The addition of an initial drying and wetting stage enabled the release of entrapped solvents.

Abstract

In built environments the combustibility of wood is a great concern, which limits the use of wood as a building material due to legislation. The reaction-to-fire properties of wood can be altered with the use of fire-retardant chemicals, and most of the commonly used fire retardants already have a long history of use. However, only limited information is available on the impact of different fire retardants on the adhesion properties of wood. Additionally, comparative studies between chemicals from different groups of fire retardants is scarce. The objective of this study was to investigate and compare the effects of two commonly used fire retardants, sodium silicate (SS) and diammonium phosphate (DAP), on veneer properties, the focus being especially on thermal behavior and adhesion. Thermal properties and combustibility were studied using thermogravimetric analysis (TGA), flame test and calorimetry. Glue bond strength was analyzed with an automated bonding evaluation system (ABES) and the leaching of chemicals was determined according to EN84. Additionally, the surface characteristics of modified veneers were imaged with scanning electron microscopy (SEM). Results revealed notable differences in the thermal properties of SS and DAP, with DAP having better fire-retardant performance in all thermal testing. SS also affected thermal properties and combustibility of modified veneers, but the effect was only moderate compared to DAP. Neither SS or DAP had any significant resistance against leaching but ABES testing showed a notable increase in the glue bond strength of DAP modified veneers.

Abstract

Carbon footprint over the life cycle is one of the most common environmental performance indicators. In recent years, several wood material producers have published environmental product declarations (EPDs) according to the EN 15804, which makes it possible to compare the carbon footprint of product alternatives. The objective of this study was to investigate the effect of service life aspects by comparing the carbon footprint of treated wood decking products with similar performance expectations. The results showed that the modified wood products had substantially larger carbon footprints during manufacturing than preservative-treated decking materials. Replacement of modified wood during service life creates a huge impact on life cycle carbon footprint, while maintenance with oil provided a large contribution for preservative-treated decking. Hence, service life and maintenance intervals are crucial for the performance ranking between products. The methodological issues to be aware of are: how the functional unit specifies the key performance requirements for the installed product, and whether full replacement is the best modeling option in cases where the decking installation is close to the end of the required service life.