Separation of Bio-Based Glucaric Acid via Antisolvent Crystallization and Azeotropic Drying

Choi, Hoon; Soland, Nathan E.; Buss, Bonnie L.; Honeycutt, Nora C.; Tomashek, Emily G.; Haugen, Stefan J.; Ramirez, Kelsey J.; Miscall, Joel; Tan, Eric C. D.; Smith, Tyler N.; Saboe, Patrick O.; Karp, Eric M.

doi:10.1039/D1GC03984A

Separation of Bio-Based Glucaric Acid via Antisolvent Crystallization and Azeotropic Drying

Journal Article · 17 January 2022 · Green Chemistry

DOI:https://doi.org/10.1039/D1GC03984A· OSTI ID:1847084

; Soland, Nathan E.; Buss, Bonnie L.; Honeycutt, Nora C.; Tomashek, Emily G.; Haugen, Stefan J.; Ramirez, Kelsey J.; Miscall, Joel; ; Smith, Tyler N.; ;

Glucaric acid is regarded as a top-value added compound from biomass, however, due to prevalent lactonization, the recovery of purified glucaric acid is challenging. Accordingly, an efficient method for glucaric acid separation, especially its diacid form, is necessary to facilitate its valorization. Here, we report a robust separation process that produces glucaric acid crystals from fermentation broth. This process first recovers purified monopotassium glucarate from broth and then recovers purified glucaric acid through acidification and antisolvent crystallization. Isopropanol was found to be an effective antisolvent reducing the solubility of glucaric acid while concomitantly forming an azeotrope with water. This allows solvent removal at low temperature through azeotropic drying, which avoids lactonization, and thus prevents impurities in the resulting crystals. Overall, this process was found to separate monopotassium glucarate and glucaric acid with a recovery yield of >99.9% and 71% at purities of ca. 95.6 and 98.3%, respectively. Process modeling demonstrates the ability to recycle the antisolvents IPA and acetone with >99% recovery and determined the energy input to be ~20 MJ kg-1 for isolation of monopotassium glucarate and 714 MJ kg-1 for glucaric acid (0.06 M). The approach detailed in this work is likely applicable to the separation of other highly oxygenated bio-carboxylic acids (e.g., mevalonic acid) from fermentation broths, as well as to their recovery from abiotic reaction solutions.

Research Organization:: National Renewable Energy Laboratory (NREL), Golden, CO (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Bioenergy Technologies Office (EE-3B)

DOE Contract Number:: AC36-08GO28308

OSTI ID:: 1847084

Report Number(s):: NREL/JA-2800-81293; MainId:82066; UUID:ea0359ce-7558-4c4b-86bb-68e126ef8d91; MainAdminID:63943

Journal Information:: Green Chemistry, Journal Name: Green Chemistry Journal Issue: 3 Vol. 24

Country of Publication:: United States

Language:: English

References (39)

Emerging catalytic processes for the production of adipic acid Van de Vyver, Stijn; Román-Leshkov, Yuriy Catalysis Science & Technology, Vol. 3, Issue 6, p. 1465-1479 https://doi.org/10.1039/C3CY20728E	journal	January 2013
In situ recovery of bio-based carboxylic acids Saboe, Patrick O.; Manker, Lorenz P.; Michener, William E. Green Chemistry, Vol. 20, Issue 8 https://doi.org/10.1039/C7GC03747C	journal	January 2018
A new general method for designing affinity chromatography processes Ling, Lei; Kao, Lee-Wei; Wang, Nien-Hwa Linda Journal of Chromatography A, Vol. 1355 https://doi.org/10.1016/j.chroma.2014.05.081	journal	August 2014
Characterization of d-glucaric acid using NMR, X-ray crystal structure, and mm3 molecular modeling analyses Denton, Travis T.; Hardcastle, Kenneth I.; Dowd, Michael K. Carbohydrate Research, Vol. 346, Issue 16 https://doi.org/10.1016/j.carres.2011.08.016	journal	November 2011
Tailoring the Structure, Morphology, and Crystallization of Isodimorphic Poly(butylene succinate- ran -butylene adipate) Random Copolymers by Changing Composition and Thermal History Pérez-Camargo, Ricardo A.; Fernández-d’Arlas, Borja; Cavallo, Dario Macromolecules, Vol. 50, Issue 2 https://doi.org/10.1021/acs.macromol.6b02457	journal	January 2017
Exceptional performance of bimetallic Pt1Cu3/TiO2 nanocatalysts for oxidation of gluconic acid and glucose with O2 to glucaric acid Jin, Xin; Zhao, Meng; Shen, Jian Journal of Catalysis, Vol. 330 https://doi.org/10.1016/j.jcat.2015.05.018	journal	October 2015
Shock layer thickness and optimum linear velocity in displacement chromatography Zhu, Jie; Guiochon, Georges Journal of Chromatography A, Vol. 659, Issue 1 https://doi.org/10.1016/0021-9673(94)85003-8	journal	January 1994
An NMR Study of the Equilibration of d ‐Glucaric Acid with Lactone Forms in Aqueous Acid Solutions Brown, Jolene M.; Manley‐Harris, Merilyn; Field, Richard J. Journal of Carbohydrate Chemistry, Vol. 26, Issue 8-9 https://doi.org/10.1080/07328300701787172	journal	December 2007
Synergistic Effects of Bimetallic PtPd/TiO ₂ Nanocatalysts in Oxidation of Glucose to Glucaric Acid: Structure Dependent Activity and Selectivity Jin, Xin; Zhao, Meng; Vora, Muzzammil Industrial & Engineering Chemistry Research, Vol. 55, Issue 11 https://doi.org/10.1021/acs.iecr.5b04841	journal	March 2016
Determination of the Solubility, Dissolution Enthalpy, and Entropy of Pioglitazone Hydrochloride (Form II) in Different Pure Solvents Tao, Mengying; Wang, Zhao; Gong, Junbo Industrial & Engineering Chemistry Research, Vol. 52, Issue 8 https://doi.org/10.1021/ie303588j	journal	February 2013
How to Synthesise High Purity, Crystalline d -Glucaric Acid Selectively: How to Synthesise High Purity, Crystalline d -Glucaric Acid Selectively Armstrong, Robert D.; Kariuki, Benson M.; Knight, David W. European Journal of Organic Chemistry, Vol. 2017, Issue 45 https://doi.org/10.1002/ejoc.201701343	journal	December 2017
Optimising the design and operation of semi-continuous affinity chromatography for clinical and commercial manufacture Pollock, James; Bolton, Glen; Coffman, Jon Journal of Chromatography A, Vol. 1284 https://doi.org/10.1016/j.chroma.2013.01.082	journal	April 2013
Modifications in the nitric acid oxidation of d-glucose Smith, Tyler N.; Hash, Kirk; Davey, Cara-Lee Carbohydrate Research, Vol. 350 https://doi.org/10.1016/j.carres.2011.12.024	journal	March 2012
Pt catalysts for efficient aerobic oxidation of glucose to glucaric acid in water Lee, Jechan; Saha, Basudeb; Vlachos, Dionisios G. Green Chemistry, Vol. 18, Issue 13 https://doi.org/10.1039/C6GC00460A	journal	January 2016
Aerobic Oxidation of Glucose to Glucaric Acid under Alkaline-Free Conditions: Au-Based Bimetallic Catalysts and the Effect of Residues in a Hemicellulose Hydrolysate Derrien, Elie; Mounguengui-Diallo, Modibo; Perret, Noémie Industrial & Engineering Chemistry Research, Vol. 56, Issue 45 https://doi.org/10.1021/acs.iecr.7b01571	journal	June 2017
Biodegradable and High-Performance Poly(butylene adipate- co -terephthalate)–Lignin UV-Blocking Films Xing, Qianqiu; Ruch, David; Dubois, Philippe ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 11 https://doi.org/10.1021/acssuschemeng.7b02370	journal	September 2017
Sustainable production of glucaric acid from corn stover via glucose oxidation: An assessment of homogeneous and heterogeneous catalytic oxidation production routes Thaore, Vaishali B.; Armstrong, Robert D.; Hutchings, Graham J. Chemical Engineering Research and Design, Vol. 153 https://doi.org/10.1016/j.cherd.2019.10.042	journal	January 2020
Separation of furans and carboxylic acids from sugars in dilute acid rice straw hydrolyzates by nanofiltration Weng, Yu-Hsiang; Wei, Hwa-Jou; Tsai, Tsung-Yen Bioresource Technology, Vol. 101, Issue 13 https://doi.org/10.1016/j.biortech.2009.11.090	journal	July 2010
Potential Explosion Hazards Associated with the Autocatalytic Thermal Decomposition of Dimethyl Sulfoxide and Its Mixtures Yang, Qiang; Sheng, Min; Li, Xiaoyong Organic Process Research & Development, Vol. 24, Issue 6 https://doi.org/10.1021/acs.oprd.0c00159	journal	May 2020
Vapor−Liquid Equilibria by UNIFAC Group Contribution. 6. Revision and Extension Wittig, Roland; Lohmann, Jürgen; Gmehling, Jürgen Industrial & Engineering Chemistry Research, Vol. 42, Issue 1 https://doi.org/10.1021/ie020506l	journal	January 2003
Effects of Mass Action Equilibria on Fixed-Bed Multicomponent Ion-Exchange Dynamics Ernest, Michael V.; Whitley, Roger D.; Ma, Zidu Industrial & Engineering Chemistry Research, Vol. 36, Issue 1 https://doi.org/10.1021/ie960167u	journal	January 1997
Four Challenges for Better Biocatalysts Timson, David J. Fermentation, Vol. 5, Issue 2 https://doi.org/10.3390/fermentation5020039	journal	May 2019
Improvement of glucaric acid production in E. coli via dynamic control of metabolic fluxes Reizman, Irene M. Brockman; Stenger, Andrew R.; Reisch, Chris R. Metabolic Engineering Communications, Vol. 2 https://doi.org/10.1016/j.meteno.2015.09.002	journal	December 2015
Efficient Catalysts for the Green Synthesis of Adipic Acid from Biomass Deng, Weiping; Yan, Longfei; Wang, Binju Angewandte Chemie International Edition, Vol. 60, Issue 9 https://doi.org/10.1002/anie.202013843	journal	January 2021
4-AcNH-TEMPO-CATALYZED OXIDATION OF ALDOSES TO ALDARIC ACIDS USING CHLORINE OR BROMINE AS TERMINAL OXIDANTS Merbouh, Nabyl; Bobbitt, James M.; Brückner, Christian Journal of Carbohydrate Chemistry, Vol. 21, Issue 1-2 https://doi.org/10.1081/CAR-120003738	journal	May 2002
Purification and concentration of gluconic acid from an integrated fermentation and membrane process using response surface optimized conditions Pal, Parimal; Kumar, Ramesh; Banerjee, Subhamay Frontiers of Chemical Science and Engineering, Vol. 13, Issue 1 https://doi.org/10.1007/s11705-018-1721-z	journal	July 2018
Production of Glucaric Acid from a Synthetic Pathway in Recombinant Escherichia coli Moon, T. S.; Yoon, S. -H.; Lanza, A. M. Applied and Environmental Microbiology, Vol. 75, Issue 3 https://doi.org/10.1128/AEM.00973-08	journal	December 2008
Industrial Applications of Enzymes: Recent Advances, Techniques, and Outlooks Chapman, Jordan; Ismail, Ahmed; Dinu, Cerasela Catalysts, Vol. 8, Issue 6 https://doi.org/10.3390/catal8060238	journal	June 2018
Key parameters controlling the development of constant-pattern isotachic trains of two rare earth elements in ligand-assisted displacement chromatography Choi, Hoon; Harvey, David; Ding, Yi Journal of Chromatography A, Vol. 1563 https://doi.org/10.1016/j.chroma.2018.05.057	journal	August 2018
Crude glycerol as feedstock for the sustainable production of p-hydroxybenzoate by Pseudomonas putida S12 Verhoef, Suzanne; Gao, Nisi; Ruijssenaars, Harald J. New Biotechnology, Vol. 31, Issue 1 https://doi.org/10.1016/j.nbt.2013.08.006	journal	January 2014
Purification of single-chain antibody fragments exploiting pH-gradients in simulated moving bed chromatography Martínez Cristancho, Carlos Andrés; Seidel-Morgenstern, Andreas Journal of Chromatography A, Vol. 1434 https://doi.org/10.1016/j.chroma.2016.01.001	journal	February 2016
Design and Control of an Isopropyl Alcohol Dehydration Process via Extractive Distillation Using Dimethyl Sulfoxide as an Entrainer Arifin, Saiful; Chien, I-Lung Industrial & Engineering Chemistry Research, Vol. 47, Issue 3 https://doi.org/10.1021/ie070996n	journal	February 2008
Design of a carousel process for cesium removal using crystalline silicotitanate Hritzko, Benjamin J.; Walker, D. Douglas; Wang, N. -H. Linda AIChE Journal, Vol. 46, Issue 3 https://doi.org/10.1002/aic.690460314	journal	March 2000
Economic comparison between azeotropic distillation and different hybrid systems combining distillation with pervaporation for the dehydration of isopropanol Van Hoof, Veerle; Van den Abeele, Liesbet; Buekenhoudt, Anita Separation and Purification Technology, Vol. 37, Issue 1 https://doi.org/10.1016/j.seppur.2003.08.003	journal	June 2004
Hydroxylated nylons based on unprotected esterified D-glucaric acid by simple condensation reactions Kiely, D. E.; Chen, L.; Lin, T. H. Journal of the American Chemical Society, Vol. 116, Issue 2, p. 571-578 https://doi.org/10.1021/ja00081a018	journal	January 1994
Combinatorial synthetic pathway fine-tuning and cofactor regeneration for metabolic engineering of Escherichia coli significantly improve production of D-glucaric acid Su, Hui-Hui; Peng, Fei; Ou, Xiao-Yang New Biotechnology, Vol. 59 https://doi.org/10.1016/j.nbt.2020.03.004	journal	November 2020
Role of Biocatalysis in Sustainable Chemistry Sheldon, Roger A.; Woodley, John M. Chemical Reviews, Vol. 118, Issue 2 https://doi.org/10.1021/acs.chemrev.7b00203	journal	September 2017
Sugar Oxidation, Saccharic and Oxalic Acids by the Nitric Acid Oxidation of Dextrose Mehltretter, C. L.; Rist, C. E. Journal of Agricultural and Food Chemistry, Vol. 1, Issue 12 https://doi.org/10.1021/jf60012a005	journal	September 1953
Quantitative Determination of Pt- Catalyzed d -Glucose Oxidation Products Using 2D NMR Armstrong, R. D.; Hirayama, J.; Knight, D. W. ACS Catalysis, Vol. 9, Issue 1 https://doi.org/10.1021/acscatal.8b03838	journal	November 2018

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Separation of Bio-Based Glucaric Acid via Antisolvent Crystallization and Azeotropic Drying

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