| Citation: |
Xiaoming Xu, Yuanming Zhang, Yong Chen, Changhao Liu, Yang Li, Zhonghua Li, Zhetong Yang, Zhaosheng Li, Zhigang Zou. Green organic conversion with H2O2: challenges and opportunities[J]. Energy Lab, 2024, 2(1): 230011. doi: 10.54227/elab.20230011
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Green organic conversion with H2O2: challenges and opportunities
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Abstract
Hydrogen peroxide (H2O2), as a green oxidant, plays an important role in organic conversion reactions, such as cyclohexanone ammoximation and olefin oxidation. However, the production of H2O2 relies on the anthraquinone process, which is costly, complex, and typically done on clustered production. Furthermore, H2O2 is prone to decomposition or the generation of ineffective byproducts and unfavorable reactive groups, leading to low efficiency and waste of resources. Achieving the widespread application of H2O2 in green organic conversion reactions requires efficient utilization and low-cost on-site production of H2O2. Effective activation of H2O2 is the key to realizing efficient utilization of H2O2, which has been widely recognized. In addition, some emerging methods of on-site production of H2O2 are convenient and low-cost. These methods may gradually overcome the shortcomings of traditional methods in the future. In this review, we introduce common organic conversion reactions with H2O2, summarize the challenges of H2O2 activation, and review the progress on electrochemical, photoelectrochemical or photochemical H2O2 production. We also discuss the vision of organic conversion reactions via in-situ-generated H2O2.
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Keywords:
- organic conversion /
- H2O2 production /
- activation of H2O2 /
- in-situ-generated H2O2
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Author Biographies
Xiaoming Xu obtained his bachelor’s degree in Materials Science and Engineering from Zhengzhou University in 2019. Now, he is a Ph.D. student at Nanjing University under the supervision of Prof. Zhaosheng Li. His research interest mainly focuses on the study of H2O2 activation and utilization. 
Zhaosheng Li received his Ph.D. degree in Condensed Matter Physics from the Institute of Solid State Physics, Chinese Academy of Sciences, in 2003. After a two-year postdoctoral fellowship at Nanjing University, he became a Lecturer at this university. In 2006, he was promoted to Associate Professor. Since 2011, he has become a full Professor of Materials Science and Engineering at the College of Engineering and Applied Sciences, Nanjing University. His current research interest includes photochemistry and photocatalysis. -
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Xiaoming Xu, Yuanming Zhang, Yong Chen, Changhao Liu, Yang Li, Zhonghua Li, Zhetong Yang, Zhaosheng Li, Zhigang Zou. Green organic conversion with H2O2: challenges and opportunities[J]. Energy Lab, 2024, 2(1): 230011. doi: 10.54227/elab.20230011
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Figure 1.
a Reactions involved in cyclohexanone ammoximation methods.[5] Copyright 2021, Elsevier. b Industrial processes for propylene oxide production through the hydrogen peroxide propylene oxide (HPPO) process. c A plausible reaction pathway for the epoxidation of styrene. d Production of adipic acid with H2O2.[23] Copyright 2006, John Wiley and Sons. e Selective oxidation of (E)-cinnamyl alcohol with H2O2 using continuous flow reactors.[28] Copyright 2021, Royal Society of Chemistry.
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Figure 2.
a Reaction paths of styrene under different oxygen radicals. b Possible pathways for oxygen transfer to CyH from peroxo and hydroperoxo species in transition-metal-substituted polyoxometalates. c Calculated potential free-energy profile (kcal mol–1) for cyclohexene epoxidation with H2O2.[32] Copyright 2019, American Chemical Society. d Experimental and calculated solid-state 17O NMR spectra. e Calculated energy surface of propylene epoxidation at a dinuclear Ti site (electronic energies are given in kcal mol−1).[7] Copyright 2020, Springer Nature.
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Figure 3.
a Schematic of shell-isolated nanoparticle-enhanced Raman spectroscopy (SHINERS) detection process. b SHINERS spectra of isotope labelling. c The correlated Raman frequencies of the Fe-O stretching vibration for Fe-OOH species (grey: H, red: O, blue: Fe and yellow: Y). d SHINERS spectra in different systems. e SHINERS spectra in the decomposition process of H2O2 as a function of time. f The possible mechanism for the activation process of H2O2. g Electron transfer process in the formation of •OH by H2O2 activation. h The different charge densities of *OOH adsorbed on YFeO3 (left) and Ti-YFeO3 (right). i The corresponding integral crystal orbital Hamilton populations (ICOHP) in YFeO3-OOH and Ti-YFeO3-OOH.[9] Copyright 2022, National Academy of Science.
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Figure 4.
a Schematic illustration of H2O2 production in a half-reaction achieved by water oxidation and oxygen reduction.[38] Copyright 2020, John Wiley and Sons. b Schematic illustration of ORR and WOR pathways.[40] Copyright 2022, Elsevier. c Electrochemical of H2O2 production using pure H2 and O2 streams separately introduced to the anode and cathode, respectively. d Stability tests for continuous generation of pure H2O2 solutions with concentrations >10,000 ppm. [44] Copyright 2019, American Association for the Advancement of Science. e In situ selectivity modulation by surface-acting cations at the carbon surface. f Comparisons of peroxide selectivity and potential window width among reported electrocatalyst systems.[45] Copyright 2020, Elsevier.
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Figure 5.
a Energy diagram for photocatalytic H2O2 production via oxygen reduction. b Proposed reaction mechanism for photocatalytic H2O2 production.[47] Copyright 2022, Elsevier. c UV-vis-NIR DRS of SA-TCPP supramolecular assembly and UV–vis absorption spectrum of TCPP molecules. The strongest peak of SA-TCPP and TCPP molecules is located approximately at 415-430 nm. In contrast to TCPP molecules, the energy band absorption of SA-TCPP nanosheets extends up to 1,100 nm. d Quantum efficiency on SA-TCPP supramolecular photocatalysts with different bandpass filters.[48] Copyright 2023, Springer Nature.
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Figure 6.
a Proposed reaction pathways in the ammoximation of cyclohexanone-to-cyclohexanone oxime via in-situ-generated H2O2. In-situ H2O2 was generated on AuPd nanoparticles by binding with commercial TS-1 catalyst. And direct synthesis of H2O2 is combined with cyclohexanone ammoximation to produce oxime yields comparable to commercial processes. b Optimization of reaction parameters for the 0.33%Au-0.33%Pd/TS-1(Acetate-O+R) catalyst in a continuous regime. Cyclohexanone oxime yield (blue squares), H2 conversion (orange circles), H2 selectivity (green triangles).[13] Copyright 2022, American Association for the Advancement of Science. c PO production rate and PO selectivity after 5 h of reaction in solutions with different pH values. d PO production in the presence of photo-electro-heterogeneous catalytic and photo-heterogeneous catalytic systems. Inset: PO production for 24 h.[61] Copyright 2021, Springer Nature.
