Preparation of lactic acid from glucose in ionic liquid solvent system

Abstract

A new reaction system was designed to economically convert glucose to lactic acid environment-friendly. Hydrophobic ionic liquids were chosen as solvent that can promote the decomposition reaction of glucose, and the catalytic performance of the solid bases was evaluated. Both the reaction temperature and time can affect the yield of lactic acid. A high yield (97%) of lactic acid was achieved under the optimal reaction condition. The ¹H NMR spectra and HPLC-MS were used to identify the formation of the lactic acid and variations of ionic liquid. It is found that ionic-liquids have a unique solvent effect for glucose and bases. Water can be used as solvent to extract calcium lactate. This shows a great potential of hydrophobic ionic liquids in the solid bases catalyzed reaction that is limited by the weak solubility of solid bases in organic and water solution.

Keywords

glucose / lactic acid / ionic liquid / solid base / catalysis

References

[1] LeshkovY. R., ChhedA. J. N., DumesicJ. A.. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose [J]. Science, 2006, 312: 1933-1937

[2] OndaA., OchiT., KajiyoshiK., YanagisawaK.. Lactic acid production from glucose over activated hydrotalcites as solid base catalysts in water [J]. Catalysis Communication, 2008, 9: 1050-1053

[3] BruijnJ. M., TouwslagerF., KieboomA. P. G., BekkumH.. Alkaline degradation of monosaccharides. Part VIII: A13C NMR spectroscopic study [J]. Starch, 1987, 39(2): 49-52

[4] YangB. Y., MontgomeryR.. Alkaline degradation of glucose: Effect of initial concentration of reactants [J]. Carbohydrates Research, 1996, 280(1): 27-45

[5] TheaderO., NelsonD. A.. Aqueous, high-temperature transformation of carbohydrates relatives to utilization of biomass [J]. Advanced Carbohydrates Chemical Biochemistry, 1998, 46: 273-326

[6] BickerM., EndresS., OttL., VogelH.. Catalytical conversion of carbhydrates in subcritical water: A new chemical process for lactic acid production [J]. Journal of Molecular Catalysis, 2005, 239: 151-157

[7] JinF., ZhouZ., EnomotoH., MoriyaT., HigashijimaH.. Conversion mechanism of cellulosic biomass to lactic acid in subcritical water and acid-base catalytic effect of subcritical water [J]. Chemistry Letters, 2004, 33: 126-127

[8] AmassW., AmassA., TigheB.. A review of biodegradable polymers: Uses, current developments in the synthesis and characterization of biodegradable polyesters, blends of biodegradable polymers and recent advances in biodegradation studies [J]. Polymer International, 1998, 47: 89-144

[9] CortrightR. D., CastilloM. S., DumesicJ. A.. Conversion of biomass to 1, 2-propanediol by selective catalytic hydrogenation of lactic acid over silica-supported copper [J]. Applied Catalysis B, 2002, 39: 353-359

[10] LuntJ.. Large-scale production, properties and commercial applications of polylactic acid polymers [J]. Polymer Degradation and Stability, 1998, 59: 145-152

[11] OndaA., OchiT., KajiyoshiK., K YanagisawaK.. A new chemical process for catalytic conversion of D-glucose into lactic acid and gluconic acid [J]. Applied Catalysis A: General, 2008, 343: 49-54

[12] OndaA., OchiT., YanagisawaK.. Selective hydrolysis of cellulose into glucose over solid acid catalysts [J]. Green Chemistry, 2008, 10: 1033-1037

[13] JinF. M., YunJ., LiG. M., KishitaA., TohjiK., EnomotoH.. Hydrothermal conversion of carbohydrate biomass into formic acid [J]. Green Chemistry, 2008, 10: 612-615

[14] ZhaoH., HolladayJ. E., BrownH., ZhangZ. C.. Metal chloride in ionic liquid solvents convert sugar to 5-hydroxymethylfurfural [J]. Science, 2007, 316: 1597-1600

[15] VARMA R S, NAMBOODIRI V V. An expeditious solvent-free route to ionic liquids using microwaves [J]. Chemical Communication, 2001: 634–644.

[16] BonhoteP., DiasA., PapageorgiouN., KalyanasundaramK., GratzelM.. Hydrophobic, high conductive ambient-temperature molten salts [J]. Inorganic Chemistry, 1996, 35: 1168-1178