Clean production of lactic acid by selective carbon-carbon bond cleavage of biomass feedstock over a novel carbon-bismuth oxychloride photocatalyst

Abstract

The use of functional materials such as carbon-bismuth oxyhalides in integrated photorefineries for the clean production of fine chemicals requires restructuring. A facile biomass-assisted solvothermal fabrication of carbon/bismuth oxychloride nanocomposites (C/BiOCl) was achieved at various temperatures. Compared with BiOCl and C/BiOCl-120, C/BiOCl-180 exhibited higher crystallinity, wider visible light absorption, and a faster migration/separation rate of photoinduced carriers. For the selective C–C bond cleavage of biomass-based feedstocks photocatalyzed by C/BiOCl-180, the xylose conversion and lactic acid yield were 100% and 92.5%, respectively. C/BiOCl-180 efficiently converted different biomass-based monosaccharides to lactic acid, and the efficiency of pentoses was higher than that of hexoses. Moreover, lactic acid synthesis was favored by all active radicals including superoxide ion (·O₂⁻), holes (h⁺), hydroxyl radical (·OH), and singlet oxygen (¹O₂), with ·O₂⁻ playing a key role. The fabricated photocatalyst was stable, economical, and recyclable. The use of biomass-derived monosaccharides for the clean production of lactic acid via the C/BiOCl-180 photocatalyst has opened new research horizons for the investigation and application of C–C bond cleavage in biomass-based feedstocks.

Graphical abstract

Keywords

carbon-carbon bond cleavage / biomass reforming / C/BiOCl / lactic acid / photocatalysis

References

[1] Wuebbles D J , Jain A K . Concerns about climate change and the role of fossil fuel use. Fuel Processing Technology, 2001, 71(1–3): 99–119

[2] Bilal I , Khan D , Tan W , Azam Hassan S . Alternate energy sources and environmental quality: the impact of inflation dynamics. Gondwana Research, 2022, 106: 51–63

[3] Lin Q , Li Y H , Tang Z R , Xu Y J . Valorization of biomass-derived platform molecules via photoredox sustainable catalysis. Transactions of Tianjin University, 2020, 26(5): 325–340

[4] Qi M Y , Conte M , Anpo M , Tang Z R , Xu Y J . Cooperative coupling of oxidative organic synthesis and hydrogen production over semiconductor-based photocatalysts. Chemical Reviews, 2021, 121(21): 13051–13085

[5] Ma J L , Liu K N , Yang X P , Jin D N , Li Y C , Jiao G J , Zhou J H , Sun R C . Recent advances and challenges in photoreforming of biomass-derived feedstocks into hydrogen, biofuels, or chemicals by using functional carbon nitride. ChemSusChem, 2021, 14(22): 4903–4922

[6] Vijayakumar J , Aravindan R , Viruthagiri T . Recent trends in the production, purification and application of lactic acid. Chemical and Biochemical Engineering Quarterly, 2008, 22: 245–264

[7] Castillo Martinez F A , Balciunas E M , Salgado J M , Domínguez González J M , Converti A , Oliveira R P S . Lactic acid properties, applications and production: a review. Trends in Food Science & Technology, 2013, 30(1): 70–83

[8] Ahmad A , Banat F , Taher H . A review on the lactic acid fermentation from low-cost renewable materials: recent developments and challenges. Environmental Technology & Innovation, 2020, 20: 101138

[9] Li Y , Bhagwat S S , Cortés-Peña Y R , Ki D , Rao C V , Jin Y S , Guest J S . Sustainable lactic acid production from lignocellulosic biomass. ACS Sustainable Chemistry & Engineering, 2021, 9(3): 1341–1351

[10] Yang B Y , Montgomery R . Alkaline degradation of fructofuranosides. Carbohydrate Research, 1996, 280(1): 47–57

[11] Zhao H , Li C F , Yong X , Kumar P , Palma B , Hu Z Y , Van Tendeloo G , Siahrostami S , Larter S , Zheng D . . Coproduction of hydrogen and lactic acid from glucose photocatalysis on band-engineered Zn_1−xCd_xS homojunction. iScience, 2021, 24(2): 102109

[12] Wu Y , Qi M , Tan C , Tang Z , Xu Y . Photocatalytic selective oxidation of aromatic alcohols coupled with hydrogen evolution over CdS/WO₃ composites. Chinese Journal of Catalysis, 2022, 43(7): 1851–1859

[13] Xu Z , Zhang C , Zhang Y , Gu Y , An Y . BiOCl-based photocatalysts: synthesis methods, structure, property, application, and perspective. Inorganic Chemistry Communications, 2022, 138: 109277

[14] Wang C , Shao C , Liu Y , Zhang L . Photocatalytic properties BiOCl and Bi₂O₃ nanofibers prepared by electrospinning. Scripta Materialia, 2008, 59(3): 332–335

[15] Liu R , Wu Z , Tian J , Yu C , Li S , Yang K , Liu X , Liu M . The excellent dye-photosensitized degradation performance over hierarchical BiOCl nanostructures fabricated via a facile microwave-hydrothermal process. New Journal of Chemistry, 2018, 42(1): 137–149

[16] Yu J , Wei B , Zhu L , Gao H , Sun W , Xu L . Flowerlike C-doped BiOCl nanostructures: facile wet chemical fabrication and enhanced UV photocatalytic properties. Applied Surface Science, 2013, 284: 497–502

[17] Yang J , Liang Y , Li K , Yang G , Yin S . One-step low-temperature synthesis of 0D CeO₂ quantum dots/2D BiOX (X = Cl, Br) nanoplates heterojunctions for highly boosting photo-oxidation and reduction ability. Applied Catalysis B: Environmental, 2019, 250: 17–30

[18] Jiang J , Zhang L , Li H , He W , Yin J J . Self-doping and surface plasmon modification induced visible light photocatalysis of BiOCl. Nanoscale, 2013, 5(21): 10573–10581

[19] Gao Y , Yang W , Shan X , Chen Y . Synthesis of “walnut-like” BiOCl/Br solid solution photocatalyst by electrostatic self-assembly method. International Journal of Energy Research, 2020, 44(3): 2226–2242

[20] He Y , Li J , Li K , Sun M , Yuan C , Chen R , Sheng J , Leng G , Dong F . Bi quantum dots implanted 2D C-doped BiOCl nanosheets: enhanced visible light photocatalysis efficiency and reaction pathway. Chinese Journal of Catalysis, 2020, 41(9): 1430–1438

[21] Sun J , Wu S , Yang S-Z , Li Q , Xiong J , Yang Z , Gu L , Zhang X , Sun L . Enhanced photocatalytic activity induced by sp³ to sp² transition of carbon dopants in BiOCl crystals. Applied Catalysis B: Environmental, 2018, 221: 467–472

[22] Wang C , Liu N , Zhao X , Tian Y , Chen X , Zhang Y , Fan L , Hou B . C-doped BiOCl/Bi₂S₃ heterojunction for highly efficient photoelectrochemical detection and photocatalytic reduction of Cr(VI). Journal of Materials Science and Technology, 2023, 164: 188–197

[23] Li J , Cai L , Shang J , Yu Y , Zhang L . Giant enhancement of internal electric field boosting bulk charge separation for photocatalysis. Advanced Materials, 2016, 28(21): 4059–4064

[24] Li S , Liu S , Colmenares J , Xu Y . A sustainable approach for lignin valorization by heterogeneous photocatalysis. Green Chemistry, 2016, 18(3): 594–607

[25] Shang F , Li Y , Qi M , Tang Z , Xu Y . Photocatalytic materials for sustainable chemistry via cooperative photoredox catalysis. Catalysis Today, 2023, 410: 85–101

[26] Li B , Shao L , Wang R , Dong X , Zhao F , Gao P , Li Z . Interfacial synergism of Pd-decorated BiOCl ultrathin nanosheets for the selective oxidation of aromatic alcohols. Journal of Materials Chemistry A, 2018, 6(15): 6344–6355

[27] Jiang J , Zhao K , Xiao X , Zhang L . Synthesis and facet-dependent photoreactivity of BiOCl single-crystalline nanosheets. Journal of the American Chemical Society, 2012, 134(10): 4473–4476

[28] Pennycook S J , Jesson D E , McGibbon A J , Nellist P D . High angle dark field STEM for advanced materials. Microscopy, 1996, 45: 36–43

[29] Wu S , Wang J , Li Q , Huang Z , Rao Z , Zhou Y . Bi/BiOCl nanosheets enriched with oxygen vacancies to enhance photocatalytic CO₂ reduction. Transactions of Tianjin University, 2021, 27(2): 155–164

[30] DingLWeiRChenHHuJLiJ. Controllable synthesis of highly active BiOCl hierarchical microsphere self-assembled by nanosheets with tunable thickness. Applied Catalysis B: Environmental, 2015, 172–173: 91–99

[31] Ye L , Jin X , Leng Y , Su Y , Xie H , Liu C . Synthesis of black ultrathin BiOCl nanosheets for efficient photocatalytic H₂ production under visible light irradiation. Journal of Power Sources, 2015, 293: 409–415

[32] Hou J , Dai D , Wei R , Wu X , Wang X , Tahir M , Zou J . Narrowing the band gap of BiOCl for the hydroxyl radical generation of photocatalysis under visible light. ACS Sustainable Chemistry & Engineering, 2019, 7(19): 16569–16576

[33] Huang X , Zhang H , Zhao J , Jiang D , Zhan Q . Carbon quantum dot (CQD)-modified Bi₃O₄Br nanosheets possessing excellent photocatalytic activity under simulated sunlight. Materials Science in Semiconductor Processing, 2021, 122: 105489

[34] Wang H , Zhang W , Li X , Li J , Cen W , Li Q , Dong F . Highly enhanced visible light photocatalysis and in situ FT-IR studies on Bi metal/defective BiOCl hierarchical microspheres. Applied Catalysis B: Environmental, 2018, 225: 218–227

[35] Revathi B , Chandar N K . Clad-modified fiber-optic magnetic field sensing characteristics of anion-doped bismuth manganite nanopowders. Journal of Materials Science Materials in Electronics, 2022, 33(19): 15742–15753

[36] Liu W , Li Q , Yang X , Chen X , Xu X . Synthesis of SiC/BiOCl composites and its efficient photocatalytic activity. Catalysts, 2020, 10(8): 946

[37] Kauffman K L , Culp J T , Goodman A , Matranga C . Matranga C. FT-IR study of CO₂ adsorption in a dynamic copper(II) benzoate-pyrazine host with CO₂–CO₂ interactions in the adsorbed state. Journal of Physical Chemistry C, 2011, 115(5): 1857–1866

[38] Kang S , Pawar R C , Pyo Y , Khare V , Lee C S . Size-controlled BiOCl-RGO composites having enhanced photodegradative properties. Journal of Experimental Nanoscience, 2016, 11(4): 259–275

[39] Hao C , Xu Y , Bao M , Wang X , Zhang H , Li T . Hydrothermal synthesis of sphere-like BiOCl using sodium lignosulphonate as surfactant and its application in visible light photocatalytic degradation of rodamine B. Journal of Materials Science, 2017, 28: 3119–3127

[40] Li J , Guo L , Lei N , Song Q , Liang Z . Metallic Bi nanocrystal-modified defective BiVO₄ photoanodes with exposed (040) facets for photoelectrochemical water splitting. ChemElectroChem, 2017, 4(11): 2852–2861

[41] Kumar M K , Bhavani K , Srinivas B , Kumar S N , Sudhakar M , Naresh G , Venugopal A . Nano structured bismuth and nitrogen co-doped TiO₂ as an efficient light harvesting photocatalyst under natural sunlight for the production of H₂ by H₂O splitting. Applied Catalysis A, General, 2016, 515: 91–100

[42] Lee S F , Jimenez-Relinque E , Martinez I , Castellote M . Effects of mott-schottky frequency selection and other controlling factors on flat-band potential and band-edge position determination of TiO₂. Catalysts, 2023, 13(6): 1000

[43] Gai Y , Li J , Li S , Xia J B , Wei S H . Design of narrow-gap TiO₂: a passivated codoping approach for enhanced photoelectrochemical activity. Physical Review Letters, 2009, 102(3): 036402

[44] Ali Z , Ma J , Hong M , Sun R . Review: applications of the functional photocatalysts BiOX (X = Cl, Br, I) for clean energy, the environment, and future photobiorefineries. Journal of Materials Chemistry A, 2023, 11(7): 3297–3314

[45] Zhang Y , Yang S , Wang Z , Qin H , Lyu G , Chen J , Yang G . High selective conversion of fructose to lactic acid by photocatalytic reforming of BiOBr/Zn_x@SnO_2−n in alkaline condition. Journal of Catalysis, 2022, 413: 843–857

[46] Lv Y , Shao W , Kong Y , Li N , Huang X , Tang Z , Gong M , Li L , Wei W . Boron doping g-C₃N₄ supported Cu₂O for photocatalytic reforming of xylose into lactic acid. Journal of Environmental Chemical Engineering, 2023, 11(3): 109981

[47] Zhang Y , Luo H , Kong L , Zhao X , Miao G , Zhu L , Li S , Sun Y . Highly efficient production of lactic acid from xylose using Sn-beta catalysts. Green Chemistry, 2020, 22(21): 7333–7336

[48] Kosri C , Kiatphuengporn S , Butburee T , Youngjun S , Thongratkaew S , Faungnawakij K , Yimsukanan C , Chanlek N , Kidkhunthod P , Wittayakun J . . Selective conversion of xylose to lactic acid over metal-based Lewis acid supported on γ-Al₂O₃ catalysts. Catalysis Today, 2021, 367: 205–212

[49] Liu Y , Wang M , Zhang B , Yan D , Xiang X . Mediating the oxidizing capability of surface-bound hydroxyl radicals produced by photoelectrochemical water oxidation to convert glycerol into dihydroxyacetone. ACS Catalysis, 2022, 12(12): 6946–6957

[50] Luo L , Wang Z J , Xiang X , Yan D , Ye J . Selective activation of benzyl alcohol coupled with photoelectrochemical water oxidation via a radical relay strategy. ACS Catalysis, 2020, 10(9): 4906–4913

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

[52] Li Y , Zhang F , Chen Y , Li J , Xu Y . Photoredox-catalyzed biomass intermediate conversion integrated with H₂ production over Ti₃C₂T_x/CdS composites. Green Chemistry, 2020, 22(1): 163–169

[53] Li Y , Tang Z , Xu Y . Multifunctional graphene-based composite photocatalysts oriented by multifaced roles of graphene in photocatalysis. Chinese Journal of Catalysis, 2022, 43(3): 708–730

Competing interests

The authors declare that they have no competing interests.

Acknowledgements

This work was supported by the Foundation of the NSFC-CONICFT Joint Project (Grant No. 51961125207), National Natural Science Foundation of China (Grant No. 22008018), Innovation Support Program for High-level Talents of Dalian (Top and Leading Talents) (Grant No. 201913), and Dalian City Outstanding Talent Project (Grant No. 2019RD13).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://doi.org/10.1007/s11705-023-2380-2 and is accessible for authorized users.

RIGHTS & PERMISSIONS

2024 Higher Education Press