Efficient oxidation of monosaccharides to sugar acids under neutral condition in flow reactors with gold-supported activated carbon catalysts

Abstract

A significant reaction in the synthesis of biomass-based chemicals is the catalyst-based and targeted oxidation of monosaccharides into valuable sugar acids. In this study, an activated carbon supported gold catalyst was used to oxidize glucose and xylose to gluconic acid and xylonic acid under neutral condition. Optimization of reaction conditions for the catalysts was performed using both a batch reactor and a flow-through reactor. In a batch reactor, the yields of gluconic and xylonic acid reached 93% and 92%, respectively, at 90 °C within 180 min. In a flow reactor, both reactions reached a similar yield at 80 °C with the weight hourly space velocity of 47.1 h^–1. The reaction kinetics were explored in the flow reactor. The oxidation of glucose and xylose to gluconic and xylonic acid followed a first-order kinetics and the turnover frequency was 0.195 and 0.161 s^–1, respectively. The activation energy was evaluated to be 60.58 and 59.30 kJ·mol^–1, respectively. This study presents an environmentally friendly and feasible method for the selective oxidation of monosaccharides using an activated carbon supported gold catalyst, benefiting the high-value application of carbohydrates.

Graphical abstract

Keywords

monosaccharides oxidation / gluconic acid / xylonic acid / flow reactor / kinetics

References

[1] Qiang R , Feng S , Chen Y , Ma Q , Chen B W . Recent progress in biomass-derived carbonaceous composites for enhanced microwave absorption. Journal of Colloid and Interface Science, 2022, 606: 406–423

[2] Wan Y , Lee J M . Toward value-added dicarboxylic acids from biomass derivatives via thermo-catalytic conversion. ACS Catalysis, 2021, 11(5): 2524–2560

[3] Yan J P , Oyedeji O , Leal J H , Donohoe B S , Semelsberger T A , Li C L , Hoover A N , Webb E , Bose E A , Zeng Y N . . Characterizing variability in lignocellulosic biomass: a review. ACS Sustainable Chemistry & Engineering, 2020, 8(22): 8059–8085

[4] Zhang Q Z , Wan Z H , Yu I K M , Tsang D C W . Sustainable production of high-value gluconic acid and glucaric acid through oxidation of biomass-derived glucose: a critical review. Journal of Cleaner Production, 2021, 312: 127745–127762

[5] Hu L , Wu Z , Jiang Y T , Wang X Y , He A Y , Song J , Xu J M , Zhou S Y , Zhao Y J , Xu J X . Recent advances in catalytic and autocatalytic production of biomass-derived 5-hydroxymethylfurfural. Renewable & Sustainable Energy Reviews, 2020, 134: 110317–110375

[6] Kang S M , Fu J X , Zhang G . From lignocellulosic biomass to levulinic acid: a review on acid-catalyzed hydrolysis. Renewable & Sustainable Energy Reviews, 2018, 94: 340–362

[7] Niu W , Molefe M N , Frost J W . Microbial synthesis of the energetic material precursor 1,2,4-butanetriol. Journal of the American Chemical Society, 2003, 125(43): 12998–12999

[8] Chun B W , Dair B , Macuch P J , Wiebe D , Porteneuve C , Jeknavorian A . The development of cement and concrete additive: based on xylonic acid derived via bioconversion of xylose. Applied Biochemistry and Biotechnology, 2006, 129(1-3): 645–658

[9] Jin X , Liu M , Zhang G , Wang J , Xia Q , Sun Y , Zhou Z , Zhang W , Wang S , Lam C H . . Chemical synthesis of adipic acid from glucose and derivatives: challenges for nanocatalyst design. ACS Sustainable Chemistry & Engineering, 2020, 8(51): 18732–18754

[10] Ma J L , Zhong L X , Peng X W , Sun R C . D-Xylonic acid: a solvent and an effective biocatalyst for a three-component reaction. Green Chemistry, 2016, 18(6): 1738–1750

[11] Ye Q Q , Han Y F , Liu T , Bai Y , Chen Y J , Li J Z , Shi S Q . Magnesium oxychloride cement reinforced via D-gluconic acid sodium salt for slow-curing, with enhanced compressive strength and water resistance. Construction & Building Materials, 2021, 280: 122487–122496

[12] Choi I , Zhong Q X . Gluconic acid as a chelator to improve clarity of skim milk powder dispersions at pH 3.0. Food Chemistry, 2021, 344: 128639–128646

[13] Chu Q , Liao L H , Liu B , Han G R , Li X . Sulfite-inserted Mg-Al layered double hydroxides loaded with glucose oxidase to enable SO₂-mediated synergistic tumor therapy. Advanced Functional Materials, 2021, 31(33): 2103262–2103273

[14] Chen L , Huang Y M , Zou R , Ma J L , Li T Z , Li M S , Hao Q , Xie H B , Peng X W . Regulating TiO₂/mxenes catalysts to promote photocatalytic performance of highly selective oxidation of D-xylose. Green Chemistry, 2021, 23(3): 1382–1388

[15] Sadula S , Saha B . Aerobic oxidation of xylose to xylaric acid in water over Pt catalysts. ChemSusChem, 2018, 11(13): 2124–2129

[16] Önal Y , Schimpf S , Claus P . Structure sensitivity and kinetics of D-glucose oxidation to D-gluconic acid over carbon-supported gold catalysts. Journal of Catalysis, 2004, 223(1): 122–133

[17] Solmi S , Morreale C , Ospitali F , Agnoli S , Cavani F . Oxidation of D-glucose to glucaric acid using Au/C catalysts. ChemCatChem, 2017, 9(14): 2797–2806

[18] Megías-Sayago C , Santos J L , Ammari F , Chenouf M , Ivanova S , Centeno M A , Odriozola J A . Influence of gold particle size in Au/C catalysts for base-free oxidation of glucose. Catalysis Today, 2018, 306: 183–190

[19] Cappello V , Plais C , Vial C , Augier F . Bubble size and liquid-side mass transfer coefficient measurements in aerated stirred tank reactors with non-Newtonian liquids. Chemical Engineering Science, 2020, 211: 115280–115293

[20] Koklin A E , Klimenko T A , Kondratyuk A V , Lunin V V , Bogdan V I . Transformation of aqueous solutions of glucose over the Pt/C catalyst. Kinetics and Catalysis, 2015, 56(1): 84–88

[21] Li Z Y , Li D , Lan W , Li X H , Wan X F , Sun R C , Liu C F , Peng X W . Highly selective oxidation of monosaccharides to sugar acids at room temperature over palladium supported on surface functionalized carbon nanotubes. Green Chemistry, 2021, 23(18): 7084–7092

[22] Qi P Y , Chen S S , Chen J , Zheng J W , Zheng X L , Yuan Y Z . Catalysis and reactivation of ordered mesoporous carbon-supported gold nanoparticles for the base-free oxidation of glucose to gluconic acid. ACS Catalysis, 2015, 5(4): 2659–2670

[23] Wan Y , Zhang L N , Chen Y Y , Lin J H , Hu W D , Wang S , Lin J D , Wan S L , Wang Y . One-pot synthesis of gluconic acid from biomass-derived levoglucosan using an Au/Cs_2.5H_0.5PW₁₂O₄₀ catalyst. Green Chemistry, 2019, 21(23): 6318–6325

[24] Cattaneo S , Stucchi M , Villa A , Prati L . Gold catalysts for the selective oxidation of biomass-derived products. ChemCatChem, 2018, 11(1): 309–323

[25] Megías-Sayago C , Chakarova K , Penkova A , Lolli A , Ivanova S , Albonetti S , Cavani F , Odriozola J A . Understanding the role of the acid sites in 5-hydroxymethylfurfural oxidation to 2,5-furandicarboxylic acid reaction over gold catalysts: surface investigation on Ce_xZr_1–xO₂ compounds. ACS Catalysis, 2018, 8(12): 11154–11164

[26] Meng X T , Li Z Y , Li D , Huang Y M , Ma J J , Liu C F , Peng X W . Efficient base-free oxidation of monosaccharide into sugar acid under mild conditions using hierarchical porous carbon supported gold catalysts. Green Chemistry, 2020, 22(8): 2588–2597

[27] Jiang H , Gu J X , Zheng X S , Liu M , Qiu X Q , Wang L B , Li W Z , Chen Z F , Ji X B , Li J . Defect-rich and ultrathin N doped carbon nanosheets as advanced trifunctional metal-free electrocatalysts for the ORR, OER and HER. Energy & Environmental Science, 2019, 12(1): 322–333

[28] Qiu Y Y , Ali S , Lan G J , Tong H Q , Fan J T , Liu H Y , Li B , Han W F , Tang H D , Liu H Z . . Defect-rich activated carbons as active and stable metal-free catalyst for acetylene hydrochlorination. Carbon, 2019, 146: 406–412

[29] Tang C , Zhang Q . Nanocarbon for oxygen reduction electrocatalysis: dopants, edges, and defects. Advanced Materials, 2017, 29(13): 1604103–1604111

[30] Bezemer G L , Radstake P B , Koot V , van Dillen A J , Geus J W , de Jong K P . Preparation of fischer-tropsch cobalt catalysts supported on carbon nanofibers and silica using homogeneous deposition-precipitation. Journal of Catalysis, 2006, 237(2): 291–302

[31] Hu C G , Dai L M . Multifunctional carbon-based metal-free electrocatalysts for simultaneous oxygen reduction, oxygen evolution, and hydrogen evolution. Advanced Materials, 2017, 29(9): 1604942–1604950

[32] Zhang J , Jin Y , Li C Y , Shen Y N , Han L , Hu Z X , Di X W , Liu Z L . Creation of three-dimensionally ordered macroporous Au/CeO₂ catalysts with controlled pore sizes and their enhanced catalytic performance for formaldehyde oxidation. Applied Catalysis B: Environmental, 2009, 91(1-2): 11–20

[33] Zhang Z H , Huber G W . Catalytic oxidation of carbohydrates into organic acids and furan chemicals. Chemical Society Reviews, 2018, 47(4): 1351–1390

[34] Lai L Y , Liu M Y , Liu J Y , Li W H , Miao W , Sun Z L , Wang Z Y , Wang Y A , Shi H B , Chen C . . Kinetic modeling of glucose oxidation to tartaric acid over monometallic Pt/TiO₂ and bimetallic AuPt/TiO₂ catalysts: role of bimetals on C−H and C−C cleavages. ACS Sustainable Chemistry & Engineering, 2023, 11(44): 15851–15864

[35] Abad A , Corma A , García H . Catalyst parameters determining activity and selectivity of supported gold nanoparticles for the aerobic oxidation of alcohols: the molecular reaction mechanism. Chemistry, 2008, 14(1): 212–222

[36] Zhang J Y , Li Z M , Huang J H , Liu C , Hong F , Zheng K , Li G . Size dependence of gold clusters with precise numbers of atoms in aerobic oxidation of D-glucose. Nanoscale, 2017, 9(43): 16879–16886

[37] Li Z Y , Li D , Zhong L X , Li X H , Liu C F , Peng X W . Base-free selective oxidation of monosaccharide into sugar acid by surface-functionalized carbon nanotube composites. Chinese Chemical Letters, 2023, 34(11): 108370–108378

[38] Qi X Y , He Y L , Yao Y , Li Y R , Zhang L , Geng M , Wei H , Chu H B , Chu H . Effect of CeO₂ morphology on the catalytic properties of Au/CeO₂ for base-free glucose oxidation. Catalysis Science & Technology, 2022, 12(4): 1313–1323

[39] Pereira C C M , Lachter E R . Alkylation of toluene and anisole with 1-octen-3-ol over niobium catalysts. Applied Catalysis A, General, 2004, 266(1): 67–72

[40] de la Cruz M H C , da Silva J F C , Lachter E R . Catalytic activity of niobium phosphate in the Friedel-Crafts reaction of anisole with alcohols. Catalysis Today, 2006, 118(3-4): 379–384

[41] Carniti P , Gervasini A , Bossola F , Dal Santo V . Cooperative action of Bronsted and Lewis acid sites of niobium phosphate catalysts for cellobiose conversion in water. Applied Catalysis B: Environmental, 2016, 193: 93–102

Competing interests

The authors declare that they have no competing interests.

Acknowledegments

We thank the support from the National Key Research and Development Program of China (Grant No. 2021YFC2101604), the National Natural Science Foundation of China (Grant No. 22108088), and the Natural Science Foundation of Guangdong, China (Grant No. 2023A1515012740). We are grateful to Oushisheng (Beijing) Technology Co., Ltd. for providing H-Flow-S10 Flow-through Reactor and Mr. Pengfei Zhang for technical support.

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://doi.org/10.1007/s11705-024-2457-6 and is accessible for authorized users.

RIGHTS & PERMISSIONS

2024 Higher Education Press