CORE-SCCER CONFERENCE, 20 November 2020, Bern
CORE-SCCER CONFERENCE, 20 November 2020, Bern
KEY RESULT
Lignocellulosic biomass can be fully fractionated with high recovery of both structural carbohydrates and stabilized lignin/lignin monomers
through the use of protective aldehydes in the fractionation step. This not only lead to a wide pool of commonly used chemicals, but also expand the actual chemical space with the creation of novel upgrading pathways.
Energy research conference, 20 November 2020, Biel
Chemical Functionalization of Plants as a Tool for the Production of Renewables Chemicals
and Fuels
Aldehyde-assisted stabilization of lignin
Example of Application: Production of Vanillin from Hardwood
[4]O R1 H ,H+
H2O R1 = H, Et
No Aldehyde With Aldehyde
Hydrogenolysis
R1 = H, R2 = H, CH2OH R1 = Et, R2 = H
O O
OMe O
O R1 MeO
O OMe
R2
HO MeO
HO O
OH
OH O
OH OMe MeO
OH O
OH MeO
OMe HO
O
OH OMe MeO
HO O
MeO
O
OH
O O
MeO
OH OMe
O
OMe OMe
O O
MeO OMe
MeO OMe
OH
H2O H+
H+
O
OH OMe
O
O
OMe O
OH OMe
O
MeO
O OMe
MeO
RECONDENSATION R1 = H, R3 = H (Modd), Me (Meven) R1 = Et, R3 = H (Modd)
Me HO
MeO
R3
M1/M2
HO
MeO Me
R3
M3/M4 Me HO
MeO
OMe R3
M5/M6
HO MeO
OMe
Me
R3 M7/M8 HO
MeO
OMe
OH R3 M9/M10
LIGNIN
Aldehyde-assisted stabilization of carbohydrates
Selective oxidation
Hydrolysis Hydroge- nation
Oxidative cleavage
Lignin separated by aldehyde stabilized extraction method, with nearly complete extraction
[1-3]VANILLIN
> 80% yield 90% selectivity
Jessica C. Rohrbach, Jeremy S. Luterbacher
Laboratory of Sustainable and Catalytic Processing, Institute of Chemical Sciences and Engineering. École Polytechnique Fédérale de Lausanne (EPFL). CH-1015 Lausanne, Switzerland
[1] L. Shuai, M. T. Amiri, Y. M. Questell-Santiago, F. Heroguel, Y. D. Li, H. Kim, R. Meilan, C. Chapple, J. Ralph, J. S. Luterbacher, Science 2016, 354, 329-333.
[2] W. Lan, M. T. Amiri, C. M. Hunston, J. S. Luterbacher, Angew Chem Int Edit 2018, 57, 1356-1360.
[3] M. T. Amiri, G. R. Dick, Y. M. Questell-Santiago, J. S. Luterbacher, Nat Protoc 2019, 14, 921-954.
[4] W. Lan, J. B. de Bueren, J. S. Luterbacher, Angew Chem Int Edit 2019, 58, 2649-2654.
[5] Y. M. Questell-Santiago, J. Yeap, M. T. Amiri, B. P. Le Monnier, J. S. Luterbacher, ACS Sustain Chem Eng 2020, 8,
1709-1714
References
Development of a clean, economically competitive and widely available renewable energy- and carbon-source is required to supplant the current dependence of economies on unsustainable fossil resources
Agricultural- and forestry-residues arise as promising feedstocks, but the harsh conditions required to overcome their recalcitrance to hydrolysis impede their large-scale implementation
We demonstrate the application of protective chemistry during fractionation to prevent lignin recondensation and degradation products formation, paving the way to the full valorization of the lignocellulosic feedstocks
! Up to 95% stabilization and recovery of xylose, compared to 16%
xylose recovery without formaldehyde.
GLUCOSE
DEGRADATION PRODUCTS
No Aldehyde With Aldehyde
O
O O
O O O
O
O O
O O
HO O
HO HO
OH OH HO
OH
O
OH O
H, H H+
H+
3 H2O Diformylglucose isomers
+
O O
O O
O OH
Diformylxylose
XYLOSE
HO O HO
OH OH OH
O
HO O H+
3 H2O
O H, H H+
