Synthesis of 1,4:3,6-dianhydrohexitols diesters from the palladium-catalyzed hydroesterification reaction

ChemSusChem. 2014 Nov;7(11):3157-63. doi: 10.1002/cssc.201402584. Epub 2014 Sep 10.

Abstract

The hydroesterification of alpha olefins has been used to synthesize diesters from bio-based secondary diols: isosorbide, isomannide, and isoidide. The reaction was promoted by 0.2% palladium catalyst generated in situ from palladium acetate/triphenylphosphine/para-toluene sulfonic acid. Optimized reaction conditions allowed the selective synthesis of the diesters with high yields and the reaction conditions could be scaled up to the synthesis of hundred grams of diesters from isosorbide and 1-octene with solvent-free conditions.

Keywords: diester; hydroesterification; isosorbide; olefin; palladium.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Carbon Monoxide / chemistry*
  • Catalysis
  • Esterification
  • Esters
  • Iodides / chemistry
  • Isosorbide / chemistry*
  • Palladium / chemistry*

Substances

  • 1,4-3,6-dianhydromannitol
  • Alkenes
  • Bridged Bicyclo Compounds, Heterocyclic
  • Esters
  • Iodides
  • Palladium
  • Carbon Monoxide
  • 1-octene
  • Isosorbide