Synthesis, antibiotic structure–activity relationships, and cellulose dissolution studies of new room-temperature ionic liquids derived from lignin
Abstract
Ionic liquids (ILs) are promising pretreatment solvents for lignocellulosic biomass, but are largely prepared from petroleum precursors. Benzaldehydes from depolymerized lignin, such as vanillin, syringaldehyde, and 4-methoxy benzaldehyde, represent renewable feedstocks for the synthesis of ionic liquids. We herein report syntheses of novel lignin-derived ionic liquids, with extended N-alkyl chains, and examine their melting points, cellulose dissolution capacities, and toxicity profiles against Daphnia magna and E. coli strain 1A1. The latter organism has been engineered to produce isoprenol, a drop-in biofuel and precursor for commodity chemicals. The new N,N-diethyl and N,N-dipropyl methyl benzylammonium ILs were liquids at room temperature, showing 75–100 °C decreased melting points as compared to their N,N,N-trimethyl benzylammonium analog. Extension of N-alkyl chains also increased antibacterial activity threefold, while ionic liquids prepared from vanillin showed 2- to 4-fold lower toxicity as compared to those prepared from syringaldehyde and 4-methoxybenzaldehyde. The trend of antibacterial activity for anions of lignin-derived ILs was found to be methanesulfonate < acetate < hydroxide. Microcrystalline cellulose dissolution, from 2 to 4 wt% after 20 min at 100 °C, was observed in all new ILs using light microscopy and IR spectroscopy. Ionic liquids prepared from H-, S- and G-lignin oxidation products provided differential cytotoxicmore »
- Authors:
-
[1]
- Queens Univ. of Charlotte, NC (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Queens Univ. of Charlotte, NC (United States)
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE Office of Energy Efficiency and Renewable Energy (EERE), Energy Efficiency Office. Building Technologies Office; National Science Foundation (NSF)
- OSTI Identifier:
- 1808520
- Grant/Contract Number:
- AC02-05CH11231; 1601636
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Biotechnology for Biofuels
- Additional Journal Information:
- Journal Volume: 14; Journal Issue: 1; Journal ID: ISSN 1754-6834
- Publisher:
- BioMed Central
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 09 BIOMASS FUELS
Citation Formats
Liu, Shihong, Gonzalez, Michael, Kong, Celine, Weir, Scott, and Socha, Aaron M. Synthesis, antibiotic structure–activity relationships, and cellulose dissolution studies of new room-temperature ionic liquids derived from lignin. United States: N. p., 2021.
Web. doi:10.1186/s13068-021-01898-x.
Liu, Shihong, Gonzalez, Michael, Kong, Celine, Weir, Scott, & Socha, Aaron M. Synthesis, antibiotic structure–activity relationships, and cellulose dissolution studies of new room-temperature ionic liquids derived from lignin. United States. https://doi.org/10.1186/s13068-021-01898-x
Liu, Shihong, Gonzalez, Michael, Kong, Celine, Weir, Scott, and Socha, Aaron M. Tue .
"Synthesis, antibiotic structure–activity relationships, and cellulose dissolution studies of new room-temperature ionic liquids derived from lignin". United States. https://doi.org/10.1186/s13068-021-01898-x. https://www.osti.gov/servlets/purl/1808520.
@article{osti_1808520,
title = {Synthesis, antibiotic structure–activity relationships, and cellulose dissolution studies of new room-temperature ionic liquids derived from lignin},
author = {Liu, Shihong and Gonzalez, Michael and Kong, Celine and Weir, Scott and Socha, Aaron M.},
abstractNote = {Ionic liquids (ILs) are promising pretreatment solvents for lignocellulosic biomass, but are largely prepared from petroleum precursors. Benzaldehydes from depolymerized lignin, such as vanillin, syringaldehyde, and 4-methoxy benzaldehyde, represent renewable feedstocks for the synthesis of ionic liquids. We herein report syntheses of novel lignin-derived ionic liquids, with extended N-alkyl chains, and examine their melting points, cellulose dissolution capacities, and toxicity profiles against Daphnia magna and E. coli strain 1A1. The latter organism has been engineered to produce isoprenol, a drop-in biofuel and precursor for commodity chemicals. The new N,N-diethyl and N,N-dipropyl methyl benzylammonium ILs were liquids at room temperature, showing 75–100 °C decreased melting points as compared to their N,N,N-trimethyl benzylammonium analog. Extension of N-alkyl chains also increased antibacterial activity threefold, while ionic liquids prepared from vanillin showed 2- to 4-fold lower toxicity as compared to those prepared from syringaldehyde and 4-methoxybenzaldehyde. The trend of antibacterial activity for anions of lignin-derived ILs was found to be methanesulfonate < acetate < hydroxide. Microcrystalline cellulose dissolution, from 2 to 4 wt% after 20 min at 100 °C, was observed in all new ILs using light microscopy and IR spectroscopy. Ionic liquids prepared from H-, S- and G-lignin oxidation products provided differential cytotoxic activity against E. coli and D. magna, suggesting these compounds could be tailored for application specificity within a biorefinery.},
doi = {10.1186/s13068-021-01898-x},
journal = {Biotechnology for Biofuels},
number = 1,
volume = 14,
place = {United States},
year = {Tue Feb 23 00:00:00 EST 2021},
month = {Tue Feb 23 00:00:00 EST 2021}
}
Free Publicly Available Full Text
Publisher's Version of Record
Other availability
Search WorldCat to find libraries that may hold this journal
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Ionic-Liquid-Mediated Extraction and Separation Processes for Bioactive Compounds: Past, Present, and Future Trends
journal, February 2017
- Ventura, Sónia P. M.; e. Silva, Francisca A.; Quental, Maria V.
- Chemical Reviews, Vol. 117, Issue 10
Using Caenorhabditis elegans to probe toxicity of 1-alkyl-3-methylimidazolium chloride based ionic liquids
journal, January 2004
- Swatloski, Richard P.; Holbrey, John D.; Memon, Shermeen B.
- Chemical Communications, Issue 6
Imidiazolium based ionic liquids: Effects of different anions and alkyl chains lengths on the barley seedlings
journal, March 2014
- Cvjetko Bubalo, Marina; Hanousek, Karla; Radošević, Kristina
- Ecotoxicology and Environmental Safety, Vol. 101
Predicting melting points of quaternary ammonium ionic liquidsElectronic supplementary information (ESI) available: training sets B and C. See http://www.rsc.org/suppdata/gc/b3/b301217d/
journal, January 2003
- Eike, David M.; Brennecke, Joan F.; Maginn, Edward J.
- Green Chemistry, Vol. 5, Issue 3
Dissolution of Cellose with Ionic Liquids
journal, May 2002
- Swatloski, Richard P.; Spear, Scott K.; Holbrey, John D.
- Journal of the American Chemical Society, Vol. 124, Issue 18, p. 4974-4975
Deconstruction of lignocellulosic biomass with ionic liquids
journal, January 2013
- Brandt, Agnieszka; Gräsvik, John; Hallett, Jason P.
- Green Chemistry, Vol. 15, Issue 3
Transforming biomass conversion with ionic liquids: process intensification and the development of a high-gravity, one-pot process for the production of cellulosic ethanol
journal, January 2016
- Xu, Feng; Sun, Jian; Konda, N. V. S. N. Murthy
- Energy & Environmental Science, Vol. 9, Issue 3
Cellulose Dissolution and Biomass Pretreatment Using Quaternary Ammonium Ionic Liquids Prepared from H-, G-, and S-Type Lignin-Derived Benzaldehydes and Dimethyl Carbonate
journal, May 2019
- Diez, Victoria; DeWeese, Andrew; Kalb, Roland S.
- Industrial & Engineering Chemistry Research, Vol. 58, Issue 35
Recent Advances in Solvents for the Dissolution, Shaping and Derivatization of Cellulose: Quaternary Ammonium Electrolytes and their Solutions in Water and Molecular Solvents
journal, February 2018
- Kostag, Marc; Jedvert, Kerstin; Achtel, Christian
- Molecules, Vol. 23, Issue 3
Anti-microbial activities of ionic liquids
journal, December 2002
- Pernak, Juliusz; Sobaszkiewicz, Kinga; Mirska, Ilona
- Green Chemistry, Vol. 5, Issue 1
Integration of renewable deep eutectic solvents with engineered biomass to achieve a closed-loop biorefinery
journal, June 2019
- Kim, Kwang Ho; Eudes, Aymerick; Jeong, Keunhong
- Proceedings of the National Academy of Sciences, Vol. 116, Issue 28
Screening ionic liquids for use in biotransformations with whole microbial cells
journal, January 2011
- Wood, Nicola; Ferguson, Jamie L.; Gunaratne, H. Q. Nimal
- Green Chemistry, Vol. 13, Issue 7
Cellulose solubilities in carboxylate-based ionic liquids
journal, January 2012
- Zhao, Bin; Greiner, Lasse; Leitner, Walter
- RSC Advances, Vol. 2, Issue 6
Biobased Ionic Liquids: Solvents for a Green Processing Industry?
journal, May 2016
- Hulsbosch, Joris; De Vos, Dirk E.; Binnemans, Koen
- ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 6
Biological effects of imidazolium ionic liquids with varying chain lengths in acute Vibrio fischeri and WST-1 cell viability assays
journal, July 2004
- Ranke, J.; Mölter, K.; Stock, F.
- Ecotoxicology and Environmental Safety, Vol. 58, Issue 3
Membrane interactions of ionic liquids: Possible determinants for biological activity and toxicity
journal, December 2012
- Gal, Noga; Malferarri, Danilo; Kolusheva, Sofiya
- Biochimica et Biophysica Acta (BBA) - Biomembranes, Vol. 1818, Issue 12
Electrochemical Deposition of Silver in Room-Temperature Ionic Liquids and Its Surface-Enhanced Raman Scattering Effect
journal, November 2004
- He, Ping; Liu, Hongtao; Li, Zhiying
- Langmuir, Vol. 20, Issue 23
Ionic liquid pretreatment of lignocellulosic biomass with ionic liquid–water mixtures
journal, January 2011
- Brandt, Agnieszka; Ray, Michael J.; To, Trang Q.
- Green Chemistry, Vol. 13, Issue 9
Effects of different head groups and functionalised side chains on the aquatic toxicity of ionic liquids
journal, January 2007
- Stolte, Stefan; Matzke, Marianne; Arning, Jürgen
- Green Chemistry, Vol. 9, Issue 11
Development of an E. coli strain for one-pot biofuel production from ionic liquid pretreated cellulose and switchgrass
journal, January 2016
- Frederix, Marijke; Mingardon, Florence; Hu, Matthew
- Green Chemistry, Vol. 18, Issue 15
Synthesis and anti-microbial activities of some pyridinium salts with alkoxymethyl hydrophobic group
journal, December 2001
- Pernak, J.
- European Journal of Medicinal Chemistry, Vol. 36, Issue 11-12
Optimization of the IPP-bypass mevalonate pathway and fed-batch fermentation for the production of isoprenol in Escherichia coli
journal, December 2019
- Kang, Aram; Mendez-Perez, Daniel; Goh, Ee-Been
- Metabolic Engineering, Vol. 56
A morpholinium ionic liquid for cellulose dissolution
journal, October 2015
- Raut, Dilip G.; Sundman, Ola; Su, Weiqing
- Carbohydrate Polymers, Vol. 130
Comparison of dilute acid and ionic liquid pretreatment of switchgrass: Biomass recalcitrance, delignification and enzymatic saccharification
journal, July 2010
- Li, Chenlin; Knierim, Bernhard; Manisseri, Chithra
- Bioresource Technology, Vol. 101, Issue 13
Efficient biomass pretreatment using ionic liquids derived from lignin and hemicellulose
journal, August 2014
- Socha, A. M.; Parthasarathi, R.; Shi, J.
- Proceedings of the National Academy of Sciences, Vol. 111, Issue 35
Understanding pretreatment efficacy of four cholinium and imidazolium ionic liquids by chemistry and computation
journal, January 2014
- Sun, Ning; Parthasarathi, Ramakrishnan; Socha, Aaron M.
- Green Chem., Vol. 16, Issue 5
Increased Use of Quaternary Ammonium Compounds during the SARS-CoV-2 Pandemic and Beyond: Consideration of Environmental Implications
journal, June 2020
- Hora, Priya I.; Pati, Sarah G.; McNamara, Patrick J.
- Environmental Science & Technology Letters, Vol. 7, Issue 9
Task Specific Ionic Liquids for Cellulose Technology
journal, January 2009
- Ohno, Hiroyuki; Fukaya, Yukinobu
- Chemistry Letters, Vol. 38, Issue 1
Unexpected improvement in stability and utility of cytochrome c by solution in biocompatible ionic liquids
journal, January 2006
- Fujita, Kyoko; Forsyth, Maria; MacFarlane, Douglas R.
- Biotechnology and Bioengineering, Vol. 94, Issue 6
Structural characterization of Argania spinosa Moroccan wooden artifacts during natural degradation progress using infrared spectroscopy (ATR-FTIR) and X-Ray diffraction (XRD)
journal, September 2019
- Boukir, Abdellatif; Fellak, Somia; Doumenq, Pierre
- Heliyon, Vol. 5, Issue 9
Fermentation of lignocellulosic hydrolysates. I: inhibition and detoxification
journal, August 2000
- Palmqvist, Eva; Hahn-Hägerdal, Bärbel
- Bioresource Technology, Vol. 74, Issue 1, p. 17-24
Synthesis of three advanced biofuels from ionic liquid-pretreated switchgrass using engineered Escherichia coli
journal, November 2011
- Bokinsky, G.; Peralta-Yahya, P. P.; George, A.
- Proceedings of the National Academy of Sciences, Vol. 108, Issue 50, p. 19949-19954
Deciphering interactions of ionic liquids with biomembrane
journal, March 2018
- Sharma, V. K.; Mukhopadhyay, R.
- Biophysical Reviews, Vol. 10, Issue 3
Ionic liquids in biotechnology: applications and perspectives for biotransformations
journal, December 2008
- Roosen, Christoph; Müller, Pia; Greiner, Lasse
- Applied Microbiology and Biotechnology, Vol. 81, Issue 4
Elucidation of molecular interactions between lipid membranes and ionic liquids using model cell membranes
journal, January 2012
- Jeong, Seunghwan; Ha, Sung Ho; Han, Sang-Hyun
- Soft Matter, Vol. 8, Issue 20
Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure–property relationship modeling
journal, January 2006
- Couling, David J.; Bernot, Randall J.; Docherty, Kathryn M.
- Green Chem., Vol. 8, Issue 1
Statistical design of experiments for production and purification of vanillin and aminophenols from commercial lignin
journal, January 2020
- Liu, Shihong; Das, Lalitendu; Blauch, David N.
- Green Chemistry, Vol. 22, Issue 12
Task-Specific Ionic Liquids
journal, September 2004
- H. Davis, Jr., James
- Chemistry Letters, Vol. 33, Issue 9
Novel biocompatible cholinium-based ionic liquids—toxicity and biodegradability
journal, January 2010
- Petkovic, Marija; Ferguson, Jamie L.; Gunaratne, H. Q. Nimal
- Green Chemistry, Vol. 12, Issue 4
Biomass pretreatment using deep eutectic solvents from lignin derived phenols
journal, January 2018
- Kim, Kwang Ho; Dutta, Tanmoy; Sun, Jian
- Green Chemistry, Vol. 20, Issue 4
Scale-up and process integration of sugar production by acidolysis of municipal solid waste/corn stover blends in ionic liquids
journal, January 2017
- Li, Chenlin; Liang, Ling; Sun, Ning
- Biotechnology for Biofuels, Vol. 10, Issue 1
A comparative study of ethanol production using dilute acid, ionic liquid and AFEX™ pretreated corn stover
journal, January 2014
- Uppugundla, Nirmal; da Costa Sousa, Leonardo; Chundawat, Shishir PS
- Biotechnology for Biofuels, Vol. 7, Issue 1
Applications of Ionic Liquids in the Food and Bioproducts Industries
journal, August 2016
- Toledo Hijo, Ariel A. C.; Maximo, Guilherme J.; Costa, Mariana C.
- ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 10
Membrane interactions of ionic liquids: Possible determinants for biological activity and toxicity
journal, December 2012
- Gal, Noga; Malferarri, Danilo; Kolusheva, Sofiya
- Biochimica et Biophysica Acta (BBA) - Biomembranes, Vol. 1818, Issue 12
Synthesis and antimicrobial activities of new pyridinium and benzimidazolium chlorides
journal, April 2001
- Pernak, J.
- European Journal of Medicinal Chemistry, Vol. 36, Issue 4
Ionic-Liquid-Mediated Extraction and Separation Processes for Bioactive Compounds: Past, Present, and Future Trends
journal, February 2017
- Ventura, Sónia P. M.; e. Silva, Francisca A.; Quental, Maria V.
- Chemical Reviews, Vol. 117, Issue 10
Predicting melting points of quaternary ammonium ionic liquidsElectronic supplementary information (ESI) available: training sets B and C. See http://www.rsc.org/suppdata/gc/b3/b301217d/
journal, January 2003
- Eike, David M.; Brennecke, Joan F.; Maginn, Edward J.
- Green Chemistry, Vol. 5, Issue 3
Integration of renewable deep eutectic solvents with engineered biomass to achieve a closed-loop biorefinery
journal, June 2019
- Kim, Kwang Ho; Eudes, Aymerick; Jeong, Keunhong
- Proceedings of the National Academy of Sciences, Vol. 116, Issue 28
Recent Advances in Solvents for the Dissolution, Shaping and Derivatization of Cellulose: Quaternary Ammonium Electrolytes and their Solutions in Water and Molecular Solvents
journal, February 2018
- Kostag, Marc; Jedvert, Kerstin; Achtel, Christian
- Molecules, Vol. 23, Issue 3