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Phase Transitions: Melting and Freezing02:39

Phase Transitions: Melting and Freezing

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Heating a crystalline solid increases the average energy of its atoms, molecules, or ions, and the solid gets hotter. At some point, the added energy becomes large enough to partially overcome the forces holding the molecules or ions of the solid in their fixed positions, and the solid begins the process of transitioning to the liquid state or melting. At this point, the temperature of the solid stops rising, despite the continual input of heat, and it remains constant until all of the solid is...
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Ethers to Alkyl Halides: Acidic Cleavage02:18

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Ethers are generally unreactive and unsuitable for direct nucleophilic substitution reactions since the alkoxy groups are strong bases and, therefore, poor leaving groups. However, ethers readily undergo acidic-cleavage reactions. Ethers can be converted to alkyl halides when heated with strong acids such as HBr and HI in a sequence of two substitution reactions.
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Polymer Classification: Crystallinity01:21

Polymer Classification: Crystallinity

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Unlike ionic or small covalent molecules, polymers do not form crystalline solids due to the diffusion limitations of their long-chain structures. However, polymers contain microscopic crystalline domains separated by amorphous domains.
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Cationic Chain-Growth Polymerization: Mechanism00:57

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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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C–C Bond Cleavage: Retro-Aldol Reaction00:57

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The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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Condensed lignin depolymerization via C-C bond cleavage with a disordered crystalline mesoporous zeolite.

Xiangchen Kong1, Leilei Bie2, Chao Liu3

  • 1MOE Key Laboratory of Energy Thermal Conversion & Control, School of Energy and Environment, Southeast University, Nanjing, China. xiangchen.kong@seu.edu.cn.

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Summary

A novel mesoporous zeolite efficiently breaks down condensed lignin, a biorefining byproduct. This process significantly boosts yields of valuable aromatic compounds, enabling sustainable lignin valorization.

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Area of Science:

  • Chemical Engineering
  • Materials Science
  • Catalysis

Background:

  • Condensed lignin, a byproduct of pulping and biorefining, presents a challenge for sustainable biorefineries due to recalcitrant C-C bonds.
  • These bonds limit lignin's reactivity and accessibility, hindering its efficient depolymerization and valorization.
  • Developing effective methods for condensed lignin depolymerization is crucial for maximizing the value of biomass feedstocks.

Purpose of the Study:

  • To develop an efficient catalytic strategy for the depolymerization of condensed lignin.
  • To investigate the role of disordered crystalline mesoporous zeolite (Meso-Z) in breaking C-C bonds in lignin.
  • To enhance the yield of aromatic monomers and dimers (MDs) from condensed lignin.

Main Methods:

  • Utilized a disordered crystalline mesoporous zeolite (Meso-Z) with integrated strong acidity and enhanced mass transfer.
  • Compared the performance of Meso-Z with conventional microporous zeolites for condensed lignin processing.
  • Conducted mechanistic studies involving hydrolysis and hydrogenolysis of Cα-Caryl bonds facilitated by zeolite mesoporosity.

Main Results:

  • Meso-Z achieved 3.7-7.9 times higher yields of aromatic monomers and dimers (32.0-45.6 wt%) compared to conventional zeolites.
  • The yields of aromatic compounds exceeded the theoretical maximum based on C-O bond cleavage by 250-759% due to C-C bond cleavage.
  • Mechanistic studies confirmed Brønsted and Lewis acid-assisted hydrolysis and hydrogenolysis of Cα-Caryl bonds.
  • Meso-Z demonstrated robust recyclability with stable catalytic activity over ten cycles.

Conclusions:

  • Disordered crystalline mesoporous zeolite (Meso-Z) offers an efficient strategy for depolymerizing condensed lignin.
  • The synergistic integration of acidity and mesoporosity in Meso-Z facilitates C-C bond cleavage, significantly enhancing aromatic monomer and dimer yields.
  • This approach provides a viable pathway for the valorization of industrial lignin streams, contributing to sustainable biorefining.