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Studies of the effect of different salts using 1-butanol as the extracting solvent showed that K? and Na? generated the best combination of extracting power and high HMF selectivity from the monovalent and divalent chloride salts

Solvent Effects on Fructose Dehydration to 5-Hydroxymethylfurfural in Biphasic Systems Saturated with Inorganic Salts

Topics in Catalysis, no. 3 (2009): 297-303

Cited: 308|Views13

Abstract

Furan derivatives, such as 5-hydroxymethylfurfural (HMF), obtained from acid-catalyzed dehydration of carbohydrates, can serve as renewable chemical platforms for the production of fuels and chemical intermediates. Addition of an inorganic salt to concentrated aqueous solutions of fructose (30 wt% fructose on salt free basis) in biphasi...More

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Introduction
  • Major scientific interest exists in developing new technologies for the conversion of renewable resources into sustainable energy and chemical materials, due to environmental, political, and economic concerns associated with the dependence on petroleum.
  • An abundant and carbon-neutral source that contains a broad class of compounds with different extents of functionality and molecular weights, has the potential to serve as a competitive renewable feedstock for the chemical industry.
  • Molecules derived from biomass could serve to supply a portion of the petroleumbased building blocks, and to establish a new set of chemicals with properties analogous to, or even superior to, those of current petrochemicals.
  • The main challenge in establishing a biomass-based chemical platform is to develop novel methods to efficiently separate, refine, and transform biomass while maximizing feed conversion, minimizing waste, and successfully establishing economies of scale
Highlights
  • Major scientific interest exists in developing new technologies for the conversion of renewable resources into sustainable energy and chemical materials, due to environmental, political, and economic concerns associated with our dependence on petroleum
  • The significant improvement in the value of R is attributed to the salting-out effect that NaCl induces on the extracting solvent, whereby the ions in solution alter the intermolecular forces between the liquids in equilibrium, resulting in an increased immisciblity envelope; the decreased mutual solubility of the aqueous and organic phases enhances the extraction of HMF from the aqueous phase [20, 24, 25]
  • C4 solvents generated the highest HMF yields among the C3 to C6 range aliphatic alcohols, ketones, and ethers studied, most likely due to the fact that these solvents posses the highest R-value at the reaction temperature
  • The R-value measured at room temperature may be different than the value of the HMF partition coefficient at reaction temperature, it still provides a good indication of the performance of the biphasic system and appears to be a useful tool in the solvent selection process
  • Studies of the effect of different salts using 1-butanol as the extracting solvent showed that K? and Na? generated the best combination of extracting power and high HMF selectivity from the monovalent and divalent chloride salts
  • These results indicate that the combined effects of the cation and anion species must to be taken into account when selecting the most appropriate salt to improve the selectivity for HMF formation and the partition coefficient for HMF extraction
Results
  • Results and Discussion

    Saturating the aqueous phase of a biphasic system with an inorganic salt, such as NaCl, significantly alters the extraction equilibrium of HMF (Fig. 2).
  • The significant improvement in the value of R is attributed to the salting-out effect that NaCl induces on the extracting solvent, whereby the ions in solution alter the intermolecular forces between the liquids in equilibrium, resulting in an increased immisciblity envelope; the decreased mutual solubility of the aqueous and organic phases enhances the extraction of HMF from the aqueous phase [20, 24, 25].
  • It has been reported that lower fructose concentrations generate a higher HMF selectivity [28, 29],, the authors observed that operating under biphasic conditions by using NaCl is more advantageous, generating a higher HMF selectivity than the non-salt monophasic 1-butanol system at 423 K (Table 1, runs 2 and 19)
Conclusion
  • The presence of NaCl increases the partition coefficient of HMF in biphasic systems, increasing HMF selectivity by removing it more efficiently from the reactive aqueous solution.
  • When the anion was changed from Cl- to Br-, both the R-value and the HMF selectivity resembled the non-salt system, and when it was changed to SO42-, the Rvalue increased considerably, but the HMF selectivity remained low
  • These results indicate that the combined effects of the cation and anion species must to be taken into account when selecting the most appropriate salt to improve the selectivity for HMF formation and the partition coefficient for HMF extraction
Tables
  • Table1: Dehydration results for 30 wt% fructose solutions in biphasic systems using different classes of solvents. Fructose weight percent calculated on a salt-free basis. Reaction conditions used were T = 423 K, Vorg/Vaq = 3.2 with the aqueous phase adjusted to a pH = 0.6 using HCl, and a reaction time of 35 min (85 min for run 16 using THF)
  • Table2: Dehydration results for 30 wt% fructose solutions using different salts to saturate the aqueous layer of biphasic systems using 1-butanol as the extracting solvent
Download tables as Excel
Funding
  • This work was supported by the National Science Foundation Chemical and Transport Systems Division of the Directorate for Engineering, the Great Lakes Bioenergy Research Center (GLBRC), and Virent Energy Systems
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