Singlet oxygen mediated degradation of lignin—isolation of oxidation products from steam-exploded lignin from pine

Bonini, Carlo; D’Auria, Maurizio; Ferri, Rachele

doi:10.1039/b202209e

Cited by 15 publications

(9 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The dissolution capacity of different solvents toward lignin was analyzed by UV-Vis spectroscopy according to the literature. [44][45][46][47][48][49][50][51] In a typical run, birch sawdust (1.0 g) and methanol (10 mL) were placed in a 50 mL Teon-lined autoclave reactor. The mixture was stirred for 30 min before sealing.…”

Section: Measurement Of Lignin Solubility In Various Solventsmentioning

confidence: 99%

“…A UV-Vis spectrometer is used to measure birch sawdust solutions. [45][46][47][48] The absorption peak at ca. 275 nm represents dissolved lignin.…”

Section: The Proposed Reaction Coursementioning

confidence: 99%

“…[44][45][46][47][48][49][50][51] In a typical run, birch sawdust (1.0 g) and methanol (10 mL) were placed in a 50 mL Teon-lined autoclave reactor. The mixture was stirred for 30 min before sealing.…”

Section: Measurement Of Lignin Solubility In Various Solventsmentioning

confidence: 99%

See 2 more Smart Citations

Lignin depolymerization (LDP) in alcohol over nickel-based catalysts via a fragmentation–hydrogenolysis process

Song

Wang

Cai

et al. 2013

Energy Environ. Sci.

805

661

View full text Add to dashboard Cite

Valorization of native birch wood lignin into monomeric phenols over nickel-based catalysts has been studied. High chemoselectivity to aromatic products was achieved by using Ni-based catalysts and common alcohols as solvents. The results show that lignin can be selectively cleaved into propylguaiacol and propylsyringol with total selectivity >90% at a lignin conversion of about 50%. Alcohols, such as methanol, ethanol and ethylene glycol, are suitable solvents for lignin conversion. Analyses with MALDI-TOF and NMR show that birch lignin is first fragmented into smaller lignin species consisting of several benzene rings with a molecular weight of m/z ca. 1100 to ca. 1600 via alcoholysis reaction. The second step involves the hydrogenolysis of the fragments into phenols. The presence of gaseous H 2 has no effect on lignin conversion, indicating that alcohols provide active hydrogen species, which is further confirmed by isotopic tracing experiments. Catalysts are recycled by magnetic separation and can be reused four times without losing activity. The mechanistic insights from this work could be helpful in understanding native lignin conversion and the formation of monomeric phenolics via reductive depolymerization. Broader contextNature efficiently synthesizes aromatic structures and deposits them as lignin in plants. Incorporation of catalytic technologies into lignin conversion is a possible option for valorizing the feedstock as a renewable raw material for aromatic chemical production. Use of heterogeneous catalysts facilitates separation and recycling, and has attracted great attention. However, the detailed chemistry between solid catalysts and solid feedstocks still remains unknown because of mass transfer limitations. Herein we report the valorization of native birch wood lignin into monomeric phenols over nickel-based catalysts. High chemoselectivity to aromatic products was achieved by using Ni-based catalysts and common alcohols as solvents. The results show that lignin can be selectively cleaved into propylguaiacol and propylsyringol with total selectivity >90% at a lignin conversion of about 50%. Analysis results show that birch lignin is rst fragmented into smaller lignin species consisting of several benzene rings with a molecular weight of m/z ca. 1100 to ca. 1600 via alcoholysis reaction. The second step involves the hydrogenolysis of the fragments into phenols. This study will greatly contribute to the understanding of the lignin depolymerization reaction and will be interesting for other biomass conversion.

show abstract

Section: Measurement Of Lignin Solubility In Various Solventsmentioning

confidence: 99%

“…A UV-Vis spectrometer is used to measure birch sawdust solutions. [45][46][47][48] The absorption peak at ca. 275 nm represents dissolved lignin.…”

Section: The Proposed Reaction Coursementioning

confidence: 99%

See 1 more Smart Citation

Lignin depolymerization (LDP) in alcohol over nickel-based catalysts via a fragmentation–hydrogenolysis process

Song

Wang

Cai

et al. 2013

Energy Environ. Sci.

805

661

View full text Add to dashboard Cite

show abstract

“…The average molecular weight of spruce lignin is between 4300 and 6965 Da. SEL is expected to contain more condensed structures and frequent carbon‐carbon inter‐unit linkages compared to its native counterpart …”

Section: Current Schemes For Biorefining Ligninmentioning

confidence: 99%

Pathways for biomass‐derived lignin to hydrocarbon fuels

Laskar

Yang

Wang

et al. 2013

Biofuels Bioprod Bioref

177

133

View full text Add to dashboard Cite

Production of hydrocarbon fuel from biomass‐derived lignin sources with current vision of biorefinery infrastructure would significantly improve the total carbon use in biomass and make biomass conversion more economically viable. Thus, developing specialty and commodity products from biomass derived‐lignin has been an important industrial and scientific endeavor for several decades. However, deconstruction of lignin's complex polymeric framework into low molecular weight reactive moieties amenable for deoxygenation and subsequent processing into hydrocarbons has proven challenging. This review offers a comprehensive outlook on the existing body of work that has been devoted to catalytic processing of lignin derivatives into hydrocarbon fuels, focusing on: (i) the intrinsic complexity and characteristic structural features of biomass‐derived lignin; (ii) existing processing technologies for the isolation and depolymerization of bulk lignin (including detailed mechanistic considerations); (iii) approaches aimed at significantly improving the yields of depolymerized lignin species amenable to catalytic upgrading; and (iv) catalytic upgrading, using aqueous phase processes for transforming depolymerized lignin to hydrocarbon derivatives. Technical barriers and challenges to the valorization of lignin are highlighted throughout. The central goal of this review is to present an array of strategies that have been reported to obtain lignin, deconstruct it to reactive intermediates, and reduce its substantial oxygen content to yield hydrocarbon liquids. In this regard, reaction networks with reference to studies of lignin model compounds are exclusively surveyed. Special attention is paid to catalytic hydrodeoxygenation, hydrogenolyis, and hydrogenation. Finally, this review addresses important features of lignin that are vital to economic success of hydrocarbon production. Published in 2013 by John Wiley & Sons, Ltd

show abstract

“…Lignin is an abundant heterogeneous aromatic polymer biosynthesized from phenylpropanoid building blocks in the cell walls of vascular plants. , It has significant potential to serve as a renewable source of aromatic chemicals; − however, the inherent recalcitrance , of this energy-dense polymer presents major obstacles to the production of well-defined aromatic products via chemical − or biochemical , depolymerization. Consequently, lignin is often simply burned as low-cost fuel .…”

Section: Introductionmentioning

confidence: 99%

Lignin Conversion to Low-Molecular-Weight Aromatics via an Aerobic Oxidation-Hydrolysis Sequence: Comparison of Different Lignin Sources

Das

Rahimi

Ulbrich

et al. 2018

ACS Sustainable Chem. Eng.

130

115

View full text Add to dashboard Cite

Diverse lignin samples have been subjected to a catalytic aerobic oxidation process, followed by formic-acid-induced hydrolytic depolymerization. The yield of monomeric aromatic compounds varies depending on the lignin plant source and pretreatment method. The best results are obtained from poplar lignin isolated via a acidolysis pretreatment method, which gives 42 wt% yield of low-molecular-weight aromatics. Use of other pretreatment methods and/or use of maple and maize lignins afford yields of aromatics ranging from 3 to 31 wt%. These results establish useful references for the development of improved oxidation/depolymerization protocols.

show abstract

Singlet oxygen mediated degradation of lignin—isolation of oxidation products from steam-exploded lignin from pine

Cited by 15 publications

References 12 publications

Lignin depolymerization (LDP) in alcohol over nickel-based catalysts via a fragmentation–hydrogenolysis process

Lignin depolymerization (LDP) in alcohol over nickel-based catalysts via a fragmentation–hydrogenolysis process

Pathways for biomass‐derived lignin to hydrocarbon fuels

Lignin Conversion to Low-Molecular-Weight Aromatics via an Aerobic Oxidation-Hydrolysis Sequence: Comparison of Different Lignin Sources

Contact Info

Product

Resources

About