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Related Concept Videos

Free-Radical Chain Reaction and Polymerization of Alkenes02:35

Free-Radical Chain Reaction and Polymerization of Alkenes

The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.
Hydrolysis01:15

Hydrolysis

Overview
Hydrolysis is a chemical reaction in which the addition of water breaks down a polymer into its simpler monomer units. For example, peptides break into amino acids, carbohydrates into simple sugars, and DNA into nucleotides. Enzymes often facilitate these processes.
Hydrolysis Reverses Dehydration Synthesis
Complex carbohydrates can be broken down by breaking the bonds between individual sugar units. The reaction breaks a glycosidic bond as water is added to the compound. The...
Acid Halides to Alcohols: LiAlH4 Reduction01:19

Acid Halides to Alcohols: LiAlH4 Reduction

Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
Esters to Alcohols: Hydride Reductions01:17

Esters to Alcohols: Hydride Reductions

Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate.
Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...

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Related Experiment Video

Updated: Jun 29, 2026

Extraction of Lignin with High &#946;-O-4 Content by Mild Ethanol Extraction and Its Effect on the Depolymerization Yield
10:18

Extraction of Lignin with High β-O-4 Content by Mild Ethanol Extraction and Its Effect on the Depolymerization Yield

Published on: January 7, 2019

Structure-reactivity relationships in the mild reductive depolymerization of technical hydrolysis lignins.

Matteo Deroma1, Jeroen Lauwaert1, Paul Jusner2

  • 1Industrial Catalysis and Adsorption Technology (INCAT), Department of Materials Textiles and Chemical Engineering (MaTCh), Ghent University, Valentin Vaerwyckweg 1, 9000, Ghent, Belgium.

International Journal of Biological Macromolecules
|June 27, 2026
PubMed
Summary

Hydrolysis lignins (HLs) solubility and depolymerization depend on structure and carbohydrate content. The β-O-4 bond content is key for monomer yield and side chains during reductive catalytic depolymerization (RCD).

Keywords:
Bio-aromaticsHeterogeneous catalysisHydrolysis ligninLignin structureMild reductive depolymerization

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Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer
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Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer

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Quantitative 31P NMR Analysis of Lignins and Tannins
05:57

Quantitative 31P NMR Analysis of Lignins and Tannins

Published on: August 2, 2021

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Last Updated: Jun 29, 2026

Extraction of Lignin with High &#946;-O-4 Content by Mild Ethanol Extraction and Its Effect on the Depolymerization Yield
10:18

Extraction of Lignin with High β-O-4 Content by Mild Ethanol Extraction and Its Effect on the Depolymerization Yield

Published on: January 7, 2019

Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer
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Quantitative 31P NMR Analysis of Lignins and Tannins
05:57

Quantitative 31P NMR Analysis of Lignins and Tannins

Published on: August 2, 2021

Area of Science:

  • Biomass Valorization
  • Catalysis
  • Organic Chemistry

Background:

  • Hydrolysis lignins (HLs) are complex biopolymers with diverse structures.
  • Understanding HLs' behavior in depolymerization is crucial for biomass conversion.
  • Solubility and structural features influence processing efficiency.

Purpose of the Study:

  • To investigate the impact of hydrolysis lignin structure on solubility and reductive catalytic depolymerization (RCD).
  • To identify key structural factors governing depolymerization outcomes.
  • To assess the broad applicability of the RCD protocol for technical lignins.

Main Methods:

  • Characterization of eight different hydrolysis lignins.
  • Solubility testing using various ethanol/water mixtures.
  • Mild reductive catalytic depolymerization (RCD) analysis.
  • Analysis of structural properties including β-O-4 bond content and syringyl/guaiacyl ratio.

Main Results:

  • Solubility is influenced by intrinsic lignin properties and carbohydrate content; a 70/30 vol% ethanol/water mixture is generally optimal.
  • β-O-4 bond content is the primary determinant of monomer yield and para-substituted side chain formation during RCD.
  • Syringyl/guaiacyl ratio affects monomer yields per cleaved β-O-4 bond; para-substituted side chain selectivity is consistently high (~85%).
  • Carbohydrate content impacts hydroxyl group evolution; high molecular weight lignins may face diffusion limitations.

Conclusions:

  • Lignin structure, particularly β-O-4 bonds and S/G ratio, significantly dictates RCD outcomes.
  • The RCD protocol shows broad applicability across different technical lignins.
  • Carbohydrate content and molecular weight are critical factors influencing lignin solubility and depolymerization efficiency.