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WO2025024437A1 - Production d'acide oxalique et utilisation dans le ciment séquestrant le co2. - Google Patents

Production d'acide oxalique et utilisation dans le ciment séquestrant le co2. Download PDF

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Publication number
WO2025024437A1
WO2025024437A1 PCT/US2024/039140 US2024039140W WO2025024437A1 WO 2025024437 A1 WO2025024437 A1 WO 2025024437A1 US 2024039140 W US2024039140 W US 2024039140W WO 2025024437 A1 WO2025024437 A1 WO 2025024437A1
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WO
WIPO (PCT)
Prior art keywords
oxalic acid
niger
carbohydrate source
cement
fermentation broth
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Pending
Application number
PCT/US2024/039140
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English (en)
Inventor
Michael Ladisch
Luna LU
Hongyan Ma
Fernanda DA CUHNA
Eduardo XIMENES
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Purdue Research Foundation
University of Missouri Columbia
University of Missouri St Louis
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Purdue Research Foundation
University of Missouri Columbia
University of Missouri St Louis
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Publication of WO2025024437A1 publication Critical patent/WO2025024437A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12F—RECOVERY OF BY-PRODUCTS OF FERMENTED SOLUTIONS; DENATURED ALCOHOL; PREPARATION THEREOF
    • C12F3/00—Recovery of by-products
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • C12P7/44—Polycarboxylic acids
    • C12P7/46—Dicarboxylic acids having four or less carbon atoms, e.g. fumaric acid, maleic acid
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
    • C04B2111/00017—Aspects relating to the protection of the environment
    • C04B2111/00019—Carbon dioxide sequestration
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P2203/00—Fermentation products obtained from optionally pretreated or hydrolyzed cellulosic or lignocellulosic material as the carbon source
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/645—Fungi ; Processes using fungi
    • C12R2001/66—Aspergillus
    • C12R2001/685—Aspergillus niger

Definitions

  • the present disclosure relates generally to the manufacture and utilization of oxalic acid, derived from lignocellulosic biomass.
  • the oxalic acid is manufactured and then used as the acidic activator in a new-concept, acid-base cement (ABC) made exclusively from abundant but under-utilized base materials obtained from local industrial byproducts or solid wastes.
  • ABSC acid-base cement
  • the methods of the present disclosure allow for reduction in atmospheric CO2 by transforming cement manufacturing into a calcination-free (i.e. , low embodied energy) and CCh-negative process by avoiding energy- and CCh-intensive ( ⁇ 1 t CCh/t cement), thermal decomposition of CaCCh and kiln-processing of other raw materials.
  • Recent advances in preprocessing of biomass into high concentration slurries provides a unique feedstock for cost-effective production of oxalic acid, which can then be used as a cement additive, thereby sequestering atmospheric CO2, initially captured in biomass, in the concrete manufacturing process.
  • cement refers to the hydraulic binders of concretes that are formulated from Portland cement (PC) clinker.
  • Electrochemical approaches to CaO conversion may reduce a portion of emission from fuel burning, but have little impact on emissions due to decomposition and conversion of CaO into clinker.
  • the new-concept ABC avoids kiln processing and decreases CO2 emissions by 80%, while maintaining desired concrete properties.
  • ABC thus represents a novel carbon capture, utilization, and storage (CCUS) strategy that sequesters CO2 in mineralized form in concrete that when successfully developed, is applicable at a Gt scale.
  • the present disclosure is directed to methods of producing oxalic acid by fermenting a carbohydrate source with a microbial to form a fermentation broth and then isolating oxalic acid from the fermentation broth.
  • the present disclosure is further directed to methods of manufacturing CCh-sequestering cement.
  • the methods provide for the manufacture and utilization of oxalic acid, derived from lignocellulosic biomass, as the acidic activator in a new- concept, acid-base cement (ABC).
  • ABSC acid-base cement
  • the methods of the present disclosure allow for reduction in atmospheric CO2 by transforming cement manufacturing into a calcination-free (i.e., low embodied energy) and C Ch-negative process by avoiding energy- and CCh-intensive ( ⁇ 1 1 CCh/t cement), thermal decomposition of CaCCh and kiln-processing of other raw materials.
  • the method comprises: fermenting a carbohydrate source with a microbial to form a fermentation broth; isolating oxalic acid from the fermentation broth; mixing oxalic acid with at least one material comprising silicate or oxide to produce the CCh-sequestering cement.
  • FIG. 1 depicts the combination of biomass derived carboxylic acid (i.e., oxalic acid) that sequesters CO2 within a new' concept acid-base (ABC) cement as described in the present disclosure.
  • biomass derived carboxylic acid i.e., oxalic acid
  • ABSC acid-base
  • FIG. 2A depicts traditional cement (i.e., Portland cement (PC) manufacturing paradigm and sources of CO2 emission.
  • FIG. 2B depicts future manufacturing paradigm of the carbon-negative OxCem and sources of CO2 emission.
  • FIG. 3 shows a standard curve for mixed organic acids that was diluted accordingly from the stock solution as described in Example 1.
  • FIG. 4 depicts comparison of the oxalic acid peak in the samples and the standards as analyzed in Example 1.
  • FIG. 5 depicts yield stress of 300 g/L decreased from > 6000 (not shown) to ⁇ 200 (liquefied slurry) as analyzed in Example 2.
  • FIG. 6 depicts oxalic acid (OA) precipitation with CaC'E from fermentation broth. Day 0 and 10, ImL of sample in 30 mL of 10% (w/v) CaCh as analyzed in Examples 2 and 3.
  • OA oxalic acid
  • FIG. 7 depicts rheology of liquefied 300 g/L biomass as described in Example 3.
  • the present disclosure is directed to the manufacture and utilization of oxalic acid, derived from lignocellulosic biomass, as the acidic activator in a new- concept, acid-base cement (ABC) made exclusively from abundant but under-utilized base materials obtained from local industrial byproducts or solid wastes. These materials may include copper and steel slags and mine tailings abundant in certain regions, and globally abundant concrete recycling fines (CRF). Unlike traditional Portland Cement (PC), ABC does not require energy-intensive manufacturing processes and 1450°C temperatures that generates nearly 1-ton CO2 per ton of cement. The new-concept ABC avoids kiln processing and CO2 emissions due to limestone decomposition, maintains desired concrete properties, and, in addition, sequesters CO2 when biomass-derived oxalic acid is used.
  • ABS acid-base cement
  • Biomass itself integrates CO2 into its structure and thereby represents a form of sequestered carbon.
  • Sustainable sources of lignocellulosic biomass are available at the meaningful scale required for the proposed approach with 1 to 1.5 gigaton (Gt) generated annually and available for bioconversion according to a recent Department of Energy (DOE) study (reported at BETO Peer Review, April 2023).
  • Gt gigaton
  • DOE Department of Energy
  • Carbon integrated into biomass remains sequestered when the cellulosic fraction is fermented to oxalic acid (C2O4H2). This results in long-term carbon sequestration when concrete is formed from ABC.
  • oxalic acid is an effective curing agent that improves the properties of cement/concrete, and is more effective than concentrated CO2, which also has been tested for this purpose.
  • Biomass-derived Oxalic Acid Traditional methods to produce oxalic acid face several issues including: high cost, energy-intensity, and pollution (due to heavy usage of strong acids). Further, energy-efficient synthesis of oxalic acid from biomass or CO2, as envisioned by EU’s OCCEAN project (EU, "Oxalic acid from CO2 using electrochemistry at demonstration scale," SPIRE 2030, 2018. [Online], Available: https://www.spire2030.eu/ocean; E. Schuler, M. Demetriou, N. R. Shiju and G. Gruter, "Towards sustainable oxalic acid from CO2 and biomass," ChemSusChem, vol. 14. pp. 3636-3664. 2021), utilizes renewable resources (i.e.. biomass) or energy (e.g., solar thermal energy and electricity for electrochemical reduction). However, electrochemical reduction of CO2 is associated with high electricity consumption that competes with other manufacturing sectors.
  • renewable resources i.e.. biomass
  • energy e.g., solar
  • the invention described here utilizes oxalic acid from biomass via fermentation pathways.
  • Feedstock for oxalic acid manufacture Biomass slurries are formed using a recently developed approach and achieve up to 300 g/L lignocellulose in a pumpable fluid (i.e,. a shear thinning slurry with a low yield stress) based on a results with a 1 liter, agitated fed batch bioreactor containing low levels of endoglucanase enzyme (Szeto et al, Biotech Prog 37(6), e3216)).
  • a pumpable fluid i.e,. a shear thinning slurry with a low yield stress
  • endoglucanase enzyme Szeto et al, Biotech Prog 37(6), e3216
  • the fermentation used in the methods of the present disclosure include the use of carbohydrate sources such as glucose from starch in com, sucrose from sugarcane or sugar beet, sugars from food processing wastes, as well as glucose derived from lignocellulosic materials including crop residues (including com stover, wheat straw, soybean hulls, sugar cane bagasse, hardwood chips), as well as purposely grown cellulosic crops including grasses and energy cane.
  • carbohydrate sources such as glucose from starch in com, sucrose from sugarcane or sugar beet, sugars from food processing wastes, as well as glucose derived from lignocellulosic materials including crop residues (including com stover, wheat straw, soybean hulls, sugar cane bagasse, hardwood chips), as well as purposely grown cellulosic crops including grasses and energy cane.
  • the latter category 7 of materials, i.e., lignocellulosics are processed to glucose, xylose, and other monosacchari
  • lignocellulosic materials are hydrolyzed to sugars when acids in aqueous media are used at temperatures above 140°C, or by enzymes that represent a consortium of hydrolytic enzymes (cellulose enzyme mixtures that include endocellulases, cellobiohydrolases, and beta- glucosidases) that carry out hydrolysis at about 50°C and pH 4.5 to 5.5.
  • hydrolytic enzymes cellulose enzyme mixtures that include endocellulases, cellobiohydrolases, and beta- glucosidases
  • the amount of carbohydrate (i.e. lignocellulosic) required for the fermentation step is in the range of 100 to 300 g/L solids initially, at an enzyme loading of 1 to 20 FPU / g solids (equivalent to about 2 to 40 mg enzyme protein per g solids).
  • Hydrolysis to sugars that may be fermented to oxalic acid by a separate microorganism (or the same microorganisms in cases where the microbe generates its own cellulases) is carried out at pH 4 to 6 (depending on type of enzyme that is used), 50°C, mild agitation, for 24 to 96 hours.
  • the hydrolysis (which may be accompanied by simultaneous fermentation to the desired product, oxalic acid, but also to fuels and other bioproducts) occurs, the total undissolved solids will decrease and sugars that are fermentable by Aspergillus or yeasts or other microbes as described herein are generated at equivalent concentrations of between 30 and 180 g/L.
  • Suitable microbes for use in the fermentation process includes fungi strains of Aspergillus, Trichoderma and Penicillium species.
  • the fungi produce a mixture of oxalic acid, citric acid and gluconic acid, as a media acidification mechanism to prevent competitive microorganisms' growth.
  • oxalic acid production With the goal of biomass fermentation for oxalic acid production, it is fundamental that the fungus is able to produce cellulolytic enzymes in order to be able to break down cellulose into sugars.
  • Most of the research available in the literature report the use of modified Aspergillus niger strains, with overexpression of oxaloacetate hydrolase enzyme and/or lacking glucose oxidase.
  • OA titers up to 21 g/L have also been reported in fermentations with wild-type A. niger strain, in periods of 10 to 12 days.
  • particularly suitable strains include P. stiptica (BRFM1148), G. weberianum (BRFM1548), A. brasiliensis (BRFM103), A. niger (BRFM420), A. niger (BRFM421).A. niger (BRFM422), A. niger (BRFM431).
  • removal may be achieved by addition of small amounts of cement to the clarified filtration broth.
  • Acid-base cements are special alternative cements formulated by a base (e.g., MgO and FeO) and an acidic component (e.g., hydrophosphates).
  • MgO and FeO a base
  • hydrophosphates a component that is a base
  • MgO and FeO a base
  • hydrophosphates a component that is a base
  • MgO and FeO a base
  • hydrophosphates e.g., hydrophosphates
  • MPC Magnesium phosphate cement
  • MPC is the most widely-studied ABC because of its performance merits. MPC sets quickly even at low temperatures ( ⁇ -10°C). and produces high strength concrete with little shrinkage and superior durability as compared to Portland cement (PC) concrete.
  • CHCs Carbonation-hardening cements
  • CHCs are another class of ABCs, which use reactive MgO or wollastonite (CaO SiO2) as base, and CO2 as the acidic component.
  • the methods of the present disclosure seek to revolutionize cement manufacturing by avoiding calcination; leveraging abundant but overlooked raw materials with low/negative carbon-embodiment; enabling carbon-negative manufacturing to result in precipitated oxalic acid, enabling carbon sequestration by added lignocellulosic biomass derived OA to cement, to serve as a curing agent for concrete formation and simultaneously sequestering OA.
  • oxalic acid is produced from com stover using the methods of the present disclosure.
  • the growth medium for amplifying Aspergillus niger contained 1.4 g of (NH4)2SO4, 2 g of KH2PO4, 0.3 g of CaCh, 0.3 g of urea, 5 g of Soy peptone, 2 of g yeast extract, 1 ml of Tween 80, 1 ml of lx salt solution, 0.2g of MgSO ⁇ YFbO, and 30 g of Glucose.
  • a lx salt solution contained 5 mg FeSO4-7H2O, 1.6 mg MnSCh-FhO, 1.4 mg ZnSO4-7H2O, and 2 mg CaCh per liter. Because of the difficulty in measuring small amounts of chemicals above, the salt solution used was prepared as 10 times concentrated and 0. 1 ml if the 1 Ox salt solution was inoculated in growth medium. The pH of the medium was 5.04 initially and adjusted to 4.55 for 4. niger to grow by adding NaOH. The grow th medium and containers were autoclaved.
  • Aspergillus niger spores were collected and counted under microscope. Around 2 * 10 9 spores were inoculated into growth medium to make a total of 200 ml mixture (10 7 spores/ml). Then, the fungi were incubated at 32 °C and 200 rpm for 50 hours as a pre-culture.
  • a total of 11 flasks were prepared. Each flask contained 50 ml of liquified biomass, 38 ml of lx salt solution, and 10 ml pre-culture. The pH of these mixtures fell in the range from 4.09 to 4.21. In flask 1, 2 ml of IM NaOH was added and raised pH to 7.58. Because the liquified biomass solution has a buffer capacity, the pH decreased to 7. 17 after 5 minutes. Final decisions were made to add 2 ml of the NaOH in every flask to make a 100 ml reaction volume and a pH around 7. pH adjustment
  • a stock solution containing 10 g/L oxalic acid, 2 g/L citric acid and 1 g/L formic acid was first prepared. Data points on standard curve ware tested by diluting the stock solution to 1.5, 1, 0.75, 0.5, 0.25, 0.1 g/L oxalic acid concentration (FIG. 3). The areas under the curve were calculated using the embedded integration function in EMPOWER (HPLC software). Then, the areas under the oxalic acid peak were plotted with their concentration and fitted into a linear model so that an empirical relationship was determined. The model showed a reasonable R square value.
  • the proposed research plan may at first appear to be counter-intuitive since acids may be corrosive to formed concrete and since the emphasis on directing evolution of industrial Aspergillus strains has been on suppressing oxalic acid formation in order to maximize citric acid production for a range of metallurgical and food uses.
  • Citric acid is the world's largest consumed organic acid, and has been produced by A. niger for over 50 years.
  • oxalic acid is incorporated as part of the concrete curing process, and forms oxalate hydrates of Ca, Mg, or Fe, the effect is the opposite.
  • the concrete is protected.
  • the carboxylate hydrates become an integral part of the concrete structure and inhibit corrosion of concrete and imbedded iron rebar.
  • a slurry fermentation is carried out to obtain oxalic with an in-house strain of A. niger (A-12), and then detect the product by adding fermentation broth to CaCl 2 (FIG. 4). These conditions are not practical, but demonstrate the concept of production of oxalic acid directly from cellulosic slurry prepared using enzyme, water, and agitation without heating or pretreatment.
  • Aspergillus niger is also capable of producing cellulolytic enzymes, which are key for lignocellulose bioconversion and more recently liquefaction of lignocellulosic biomass (Cunha et al, 2014; Liaud et al., 2014). Advances in A. niger CRISPR/Cas9 genome editing for citric acid production by CRISPR/Cas9 is very well developed, leading to a yield of 0.95 g citric acid/g of glucose after fermentation optimization (Tong, 2019; Pappagiani, 2007). These methods will be applied to maximize another product of the citric acid cycle, i.e.. oxalic acid.
  • biomass-derived oxalic acid will be separated and recovered from the fermentation broth by methanol + HC1 precipitation and then added to various formulations of the modified cement for testing.
  • a “breadboard'’ will be assembled that scales fermentation to 10 L and employs OA recovery by precipitation with Ca++ or other divalent cations.
  • Sufficient OA will result to be able to formulate and test 2 to 5 kg cement samples at environmentally realistic conditions. This will culminate in a prototy pe demonstration, accompanied with a full economic analysis, assessment of Life Cycle Assessment (LCA) parameters and GHG impact based on bench-scale measurements.
  • Models that relate cement properties to carbon sequestration potential will be developed and validated against experimental measurements, resulting in a scalable protype, i.e., cement formulations for alternative concrete that are positioned for development of manufacturing accompanied by large scale testing.

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Abstract

La présente invention concerne des procédés de fabrication d'acide oxalique à partir de biomasse lignocellulosique et l'utilisation de l'acide oxalique fabriqué en tant qu'activateur acide dans un nouveau concept de ciment acido-basique (ABC).
PCT/US2024/039140 2023-07-24 2024-07-23 Production d'acide oxalique et utilisation dans le ciment séquestrant le co2. Pending WO2025024437A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5879463A (en) * 1996-03-08 1999-03-09 Dedini S/A.Administracao E Participacoes Process for rapid acid hydrolysis of lignocellulosic material and hydrolysis reactor
US20110165617A1 (en) * 2008-09-30 2011-07-07 Novozymes North America, Inc. Enzymatic Hydrolysis Of Pretreated Lignocellulose-Containing Material With Distillers Dried Grains
CN103641708A (zh) * 2013-11-25 2014-03-19 日照鲁信金禾生化有限公司 一种柠檬酸发酵过程中草酸的去除方法
CN113292309A (zh) * 2021-05-26 2021-08-24 深圳大学 一种供3d打印的磷酸镁水泥增材及其应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5879463A (en) * 1996-03-08 1999-03-09 Dedini S/A.Administracao E Participacoes Process for rapid acid hydrolysis of lignocellulosic material and hydrolysis reactor
US20110165617A1 (en) * 2008-09-30 2011-07-07 Novozymes North America, Inc. Enzymatic Hydrolysis Of Pretreated Lignocellulose-Containing Material With Distillers Dried Grains
CN103641708A (zh) * 2013-11-25 2014-03-19 日照鲁信金禾生化有限公司 一种柠檬酸发酵过程中草酸的去除方法
CN113292309A (zh) * 2021-05-26 2021-08-24 深圳大学 一种供3d打印的磷酸镁水泥增材及其应用

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
BILGINER ET AL.: "Development of magnesium/calcium oxalate cements", MATERIALS DE CONSTRUCCION, vol. 73, no. 350, 11 April 2023 (2023-04-11), Retrieved from the Internet <URL:https://materconstrucc.revistas.csic.es/index.php/materconstrucc/article/view/2981> [retrieved on 20240924] *
ESPEJO ET AL.: "Production and Degradation of Oxalic Acid by Brown Rot Fungi", APPLIED AND ENVIRONMENTAL MICROBIOLOGY, vol. 57, no. 7, 1 July 1991 (1991-07-01), pages 1980 - 1986, Retrieved from the Internet <URL:https://journals.asm.org/doi/abs/10.1128/aem.57.7.1980-1986.1991> [retrieved on 20240924] *
LIAUD ET AL.: "Exploring fungal biodiversity: organic acid production by 66 strains of filamentous fungi", FUNGAL BIOLOGY AND BIOTECHNOLOGY, vol. 1, no. 1, 1 November 2014 (2014-11-01), XP021203057, Retrieved from the Internet <URL:https://fungalbiolbiotech.biomedcentral.com/articles/10.1186/s40694-014-0001-z> [retrieved on 20240924], DOI: 10.1186/s40694-014-0001-z *
MAI ET AL.: "Enhanced oxalic acid production from corncob by a methanol-resistant strain of Aspergillus niger using semi solid-sate fermentation", PROCESS BIOCHEMISTRY, vol. 51, no. 1, 10 November 2015 (2015-11-10), pages 9 - 15, Retrieved from the Internet <URL:https://www.sciencedirect.com/science/article/abs/pii/S135951131530115X> [retrieved on 20240924] *

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