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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.

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Diol-enhanced natural deep eutectic solvents for efficient poplar pretreatment.

Chaehwi Yoon1, Jiae Ryu1, Soyeon Jeong1

  • 1Department of Chemical Engineering, State University of New York Environmental Science and Forestry, Syracuse, NY, United States.

Frontiers in Chemistry
|May 15, 2026
PubMed
Summary

Natural deep eutectic solvents (NDESs) show promise for biomass pretreatment. Adding diols like 1,4-butanediol to these systems reduces viscosity and enhances lignin extraction for better biofuel production.

Keywords:
3,4-dihydroxybenzoic aciddiolsfractionationnatural deep eutectic solventsviscosity

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Area of Science:

  • Biomass Pretreatment
  • Green Chemistry
  • Biorefining

Background:

  • Natural deep eutectic solvents (NDESs) are effective for biomass pretreatment but suffer from high viscosity, limiting industrial use.
  • High viscosity impedes mass transfer and scalability in NDES-based biomass processing.

Purpose of the Study:

  • To develop diol-enhanced ternary deep eutectic solvents (TDESs) with reduced viscosity for improved biomass pretreatment.
  • To investigate the impact of diols on lignin solubility, condensation, and preservation of linkages during pretreatment.
  • To evaluate the overall effectiveness of TDESs for enhanced delignification and enzymatic digestibility.

Main Methods:

  • Ternary deep eutectic solvents (TDESs) were synthesized by incorporating 1,4-butanediol (1,4-BDO) or ethylene glycol (EG) into a choline chloride (ChCl) and 3,4-dihydroxybenzoic acid (DHBA) system.
  • Viscosity, lignin solubility, and lignin condensation were analyzed for TDESs compared to binary DES (BDES).
  • Biomass pretreatment efficiency was assessed through delignification rates and enzymatic digestibility.

Main Results:

  • TDESs exhibited significantly lower viscosity than BDES while maintaining a liquid state at room temperature.
  • Diol addition enhanced lignin solubility and suppressed lignin condensation by intercepting carbocation intermediates.
  • Recovered lignin showed improved preservation of β-O-4 linkages, and TDES pretreatment led to higher delignification and enzymatic digestibility.
  • 1,4-BDO-enhanced DES successfully pretreated DHBA-enriched transgenic poplar.

Conclusions:

  • Diol-enhanced TDESs offer a synergistic approach to biomass pretreatment by reducing viscosity, increasing lignin solubility, and minimizing condensation.
  • These TDES systems improve biomass delignification and enzymatic digestibility, making lignin more amenable to downstream valorization.
  • The developed TDESs show potential for processing both conventional and engineered biomass feedstocks in biorefineries.