5 Commercial Aspects of Biomass Deconstruction with Ionic Liquids
121
41. Zhang Y-HP, Cui J, Lynd LR, Kuang LR (2006) A transition from cellulose swelling to cellulose dissolution by o-phosphoric acid: Evidence from enzymatic hydrolysis and supramolecular structure. Biomacromolecules 7: 644–648. https://doi.org/10.1021/bm050799c
42. Charles G (1933) Cellulose solution and cellulose derivative and process of making same, US
patent no 1,924,238. US Patent and Trademark Office, Washington
43. Tadesse H, Luque R (2011) Advances on biomass pretreatment using ionic liquids: an
overview. Energy Environ Sci 4:3913–3929. https://doi.org/10.1039/c0ee00667j
44. Michud A, Tanttu M, Asaadi S, Ma Y, Netti E, Kääriainen P, Persson A, Berntsson A, Hummel
M, Sixta H (2016) Ioncell-F: ionic liquid-based cellulosic textile fibers as an alternative to
viscose and Lyocell. Text Res J 86:543–552. https://doi.org/10.1177/0040517515591774
45. Zhao H, Holladay JE, Brown H, Zhang ZC (2007) Metal chlorides in ionic liquid solvents
convert sugar to 5-hydroxymethylfurfural. Science 316:1597–1600. https://doi.org/10.1126/
science.1141199
46. van Putten RJ, van der Waal JC, de Jong ED, Rasrendra CB, Heeres HJ, de Vries JG (2013)
Hydroxymethylfurfural, a versatile platform chemical made from renewable resources. Chem
Rev 113:1499−1597. https://doi.org/10.1021/cr300182k
47. Werpy T, Petersen G (eds.) (2004) Top value added chemicals from biomass volume I—
results of screening for potential candidates from sugars and synthesis gas. U.S. Department of Energy, National Renewable Energy Laboratory, Golden, CO. https://doi.org/10.
2172/15008859
48. Eminov S, Brandt A, Wilton-Ely JDET, Hallett JP (2016) The highly selective and nearquantitative conversion of glucose to 5-hydroxymethylfurfural using ionic liquids. PLoS ONE
11:e0163835. https://doi.org/10.1371/journal.pone.0163835
49. Rosatella AA, Simeonov SP, Frade RFM, Afonso CAM (2011) 5-Hydroxymethylfurfural
(HMF) as a building block platform: biological properties, synthesis and synthetic applications. Green Chem 13:754–793. https://doi.org/10.1039/c0gc00401d
50. Hou Q, Li W, Zhen M, Liu L, Chen Y, Yang Q, Huang F, Zhang S, Ju M (2017) An ionic
liquid–organic solvent biphasic system for efficient production of 5-hydroxymethylfurfural
from carbohydrates at high concentrations. RSC Adv 7:47288–47296. https://doi.org/10.1039/
C7RA10237B
51. Lima S, Neves P, Antunes MM, Pillinger M, Ignatyev N, Valente AA (2009) Conversion
of mono/di/polysaccharides into furan compounds using 1-alkyl-3-methylimidazolium ionic
liquids. Appl Catal A Gen 363:93–99. https://doi.org/10.1016/j.apcata.2009.04.049
52. Greaves TL, Drummond CJ (2008) Protic ionic liquids: properties and applications. Chem
Rev 108:206–237. https://doi.org/10.1021/cr068040u
53. Greaves TL, Kennedy DF, Mudie ST, Drummond CJ (2010) Diversity observed in the nanostructure of protic ionic liquids. J Phys Chem B 114:10022–10031. https://doi.org/10.1021/
jp103863z
54. Deetlefs M, Seddon KR (2010) Assessing the greenness of some typical laboratory ionic
liquid preparations. Green Chem 12:17–30. https://doi.org/10.1039/B915049H
55. Greaves TL, Weerawardena A, Krodkiewska I, Drummond CJ (2008) Protic ionic liquids:
physicochemical properties and behavior as amphiphile self-assembly solvents. J Phys Chem
B 112:896–905. https://doi.org/10.1021/jp0767819
56. Greaves TL, Weerawardena A, Fong C, Krodkiewska I, Drummond CJ (2006) Protic ionic
liquids: Solvents with tunable phase behavior and physicochemical properties. J Phys Chem
B Ibid. 110:26506. https://doi.org/10.1021/jp068102k
57. Yoshizawa M, Xu W, Angell CA (2003) Ionic liquids by proton transfer: vapor pressure,
conductivity, and the relevance of pK a from aqueous solutions. J Am Chem Soc 125:15411–
15419. https://doi.org/10.1021/ja035783d
58. Greaves TL, Drummond CJ (2015) Protic ionic liquids: evolving structure–property relationships and expanding applications. Chem Rev 115:11379–11448. https://doi.org/10.1021/acs.
chemrev.5b00158
121
41. Zhang Y-HP, Cui J, Lynd LR, Kuang LR (2006) A transition from cellulose swelling to cellulose dissolution by o-phosphoric acid: Evidence from enzymatic hydrolysis and supramolecular structure. Biomacromolecules 7: 644–648. https://doi.org/10.1021/bm050799c
42. Charles G (1933) Cellulose solution and cellulose derivative and process of making same, US
patent no 1,924,238. US Patent and Trademark Office, Washington
43. Tadesse H, Luque R (2011) Advances on biomass pretreatment using ionic liquids: an
overview. Energy Environ Sci 4:3913–3929. https://doi.org/10.1039/c0ee00667j
44. Michud A, Tanttu M, Asaadi S, Ma Y, Netti E, Kääriainen P, Persson A, Berntsson A, Hummel
M, Sixta H (2016) Ioncell-F: ionic liquid-based cellulosic textile fibers as an alternative to
viscose and Lyocell. Text Res J 86:543–552. https://doi.org/10.1177/0040517515591774
45. Zhao H, Holladay JE, Brown H, Zhang ZC (2007) Metal chlorides in ionic liquid solvents
convert sugar to 5-hydroxymethylfurfural. Science 316:1597–1600. https://doi.org/10.1126/
science.1141199
46. van Putten RJ, van der Waal JC, de Jong ED, Rasrendra CB, Heeres HJ, de Vries JG (2013)
Hydroxymethylfurfural, a versatile platform chemical made from renewable resources. Chem
Rev 113:1499−1597. https://doi.org/10.1021/cr300182k
47. Werpy T, Petersen G (eds.) (2004) Top value added chemicals from biomass volume I—
results of screening for potential candidates from sugars and synthesis gas. U.S. Department of Energy, National Renewable Energy Laboratory, Golden, CO. https://doi.org/10.
2172/15008859
48. Eminov S, Brandt A, Wilton-Ely JDET, Hallett JP (2016) The highly selective and nearquantitative conversion of glucose to 5-hydroxymethylfurfural using ionic liquids. PLoS ONE
11:e0163835. https://doi.org/10.1371/journal.pone.0163835
49. Rosatella AA, Simeonov SP, Frade RFM, Afonso CAM (2011) 5-Hydroxymethylfurfural
(HMF) as a building block platform: biological properties, synthesis and synthetic applications. Green Chem 13:754–793. https://doi.org/10.1039/c0gc00401d
50. Hou Q, Li W, Zhen M, Liu L, Chen Y, Yang Q, Huang F, Zhang S, Ju M (2017) An ionic
liquid–organic solvent biphasic system for efficient production of 5-hydroxymethylfurfural
from carbohydrates at high concentrations. RSC Adv 7:47288–47296. https://doi.org/10.1039/
C7RA10237B
51. Lima S, Neves P, Antunes MM, Pillinger M, Ignatyev N, Valente AA (2009) Conversion
of mono/di/polysaccharides into furan compounds using 1-alkyl-3-methylimidazolium ionic
liquids. Appl Catal A Gen 363:93–99. https://doi.org/10.1016/j.apcata.2009.04.049
52. Greaves TL, Drummond CJ (2008) Protic ionic liquids: properties and applications. Chem
Rev 108:206–237. https://doi.org/10.1021/cr068040u
53. Greaves TL, Kennedy DF, Mudie ST, Drummond CJ (2010) Diversity observed in the nanostructure of protic ionic liquids. J Phys Chem B 114:10022–10031. https://doi.org/10.1021/
jp103863z
54. Deetlefs M, Seddon KR (2010) Assessing the greenness of some typical laboratory ionic
liquid preparations. Green Chem 12:17–30. https://doi.org/10.1039/B915049H
55. Greaves TL, Weerawardena A, Krodkiewska I, Drummond CJ (2008) Protic ionic liquids:
physicochemical properties and behavior as amphiphile self-assembly solvents. J Phys Chem
B 112:896–905. https://doi.org/10.1021/jp0767819
56. Greaves TL, Weerawardena A, Fong C, Krodkiewska I, Drummond CJ (2006) Protic ionic
liquids: Solvents with tunable phase behavior and physicochemical properties. J Phys Chem
B Ibid. 110:26506. https://doi.org/10.1021/jp068102k
57. Yoshizawa M, Xu W, Angell CA (2003) Ionic liquids by proton transfer: vapor pressure,
conductivity, and the relevance of pK a from aqueous solutions. J Am Chem Soc 125:15411–
15419. https://doi.org/10.1021/ja035783d
58. Greaves TL, Drummond CJ (2015) Protic ionic liquids: evolving structure–property relationships and expanding applications. Chem Rev 115:11379–11448. https://doi.org/10.1021/acs.
chemrev.5b00158