Theoretical study on the effect of H₂O on the formation mechanism of NO_x precursors during indole pyrolysis

Abstract

The incineration technology of kitchen waste is one of the effective technologies to achieve the resource utilization of municipal solid waste. Pyrolysis is an important stage of incineration. Indole is a rich initial product in the pyrolysis process of kitchen waste, and the presence of H₂O has a significant impact on the decomposition of indole to form NO_x precursors. Therefore, this study uses density functional theory method to study the effect of H₂O on the thermal decomposition of indole to produce NH₃, HNCO, and HCN. When H₂O participates in the reaction, it can provide oxidative groups to generate a new product HNCO, which is different from the previous findings by indole pyrolysis without the presence of H₂O. Meanwhile, this study theoretically proves that NH₃ is easier to form than HCN. This is consistent with the phenomenon that NH₃ release is higher than HCN release in pyrolysis experiment. In addition, compared with the individual pyrolysis of indole, the participation of H₂O reduces the energy barriers for the formation of NH₃ and HCN during indole pyrolysis, thereby promoting the formation of NH₃ and HCN.

Key words： indole; pyrolysis; H₂O; NO_x precursors; DFT

Competing interests

The authors declare that they have no competing interests.

Acknowledgements

This work was supported by National Natural Science Foundation of China (Grant Nos. 52276127 and 51704194) and Youth Scientific Research Team Cultivation Program of Shanghai University of Engineering and Technology (Grant No. QNTD202101).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://doi.org/10.1007/s11705-024-2425-1 and is accessible for authorized users.

References

1 Li H , Xu J , Mbugua Nyambura S , Wang J , Li C , Zhu X , Feng X , Wang Y . Food waste pyrolysis by traditional heating and microwave heating: a review. Fuel, 2022, 324: 124574

2 Zhang R , Zhang M , Mou H , An Z , Fu H , Su X , Chen C , Chen J , Lin H , Sun F . Comparation of mesophilic and thermophilic anaerobic co-digestion of food waste and waste activated sludge driven by biochar derived from kitchen waste. Journal of Cleaner Production, 2023, 408: 137123

3 Nyambura S M , Jufei W , Hua L , Xuebin F , Xingjia P , Bohong L , Ahmad R , Jialiang X , Bertrand G , Ndiithi J , Xuhui L . Microwave co-pyrolysis of kitchen food waste and rice straw for waste reduction and sustainable biohydrogen production: thermo-kinetic analysis and evolved gas analysis. Sustainable Energy Technologies and Assessments, 2022, 52: 102072

4 Elgarahy A M , Eloffy M G , Alengebawy A , El Sherif D , Gaballah M , Elwakeel K , El Qelish M . Sustainable management of food waste; pre-treatment strategies, techno-economic assessment, bibliometric analysis, and potential utilizations: a systematic review. Environmental Research, 2023, 225: 115558

5 Cai P T , Chen T , Chen B , Wang Y , Ma Z , Yan J . The impact of pollutant emissions from co-incineration of industrial waste in municipal solid waste incinerators. Fuel, 2023, 352: 129027

6 Liu X , Shen J , Guo Y , Wang S , Chen B , Luo L , Zhang H . Technical progress and perspective on the thermochemical conversion of kitchen waste and relevant applications: a comprehensive review. Fuel, 2023, 331: 125803

7 Zhang W , Tan H , Chen Y , Yang H , Chen H . Pyrolysis of hydrochar from hydrothermal treatment of kitchen waste: effects of temperature, catalysts, and KOH addition. Journal of Analytical and Applied Pyrolysis, 2022, 167: 105664

8 Feng Y , Bu T , Zhang Q , Han M , Tang Z , Yuan G , Chen D , Hu Y . Pyrolysis characteristics of anaerobic digestate from kitchen waste and availability of phosphorus in pyrochar. Journal of Analytical and Applied Pyrolysis, 2022, 168: 105729

9 Wang Z , Shen J , Liu X , Guo Y , Wang S , Deng S , Zhang H . A review on nitrogen migration mechanism during the pyrolysis of organic solid waste: DFT, ReaxFF MD and experimental study. Journal of Analytical and Applied Pyrolysis, 2023, 176: 106250

10 Zhang J , Tian Y , Cui Y , Zuo W , Tan T . Key intermediates in nitrogen transformation during microwave pyrolysis of sewage sludge: a protein model compound study. Bioresource Technology, 2013, 132: 57–63

11 Jiang D , Li J , Wang S , Li H , Qian L , Li B , Cheng X , Hu Y , Hu X . Cyclic compound formation mechanisms during pyrolysis of typical aliphatic acidic amino acids. ACS Sustainable Chemistry & Engineering, 2020, 8(45): 16968–16978

12 Ebikade E O , Sadula S , Gupta Y , Vlachos D . A review of thermal and thermocatalytic valorization of food waste. Green Chemistry, 2021, 23(8): 2806–2833

13 Li K , Zhang L , Zhu L , Zhu X . Comparative study on pyrolysis of lignocellulosic and algal biomass using pyrolysis-gas chromatography/mass spectrometry. Bioresource Technology, 2017, 234: 48–52

14 Shen J , Liu X , Wang S , Chen B , Deng X , Qiu X , Wang Z , Zhang H , Guo Y . Theoretical study on nitrogen migration mechanism during the pyrolysis of 2-pyrrolidone. Fuel, 2023, 345: 128260

15 Qing M , Zheng Y , Liu L , Huang S , Zeng H , Tian H , Xiang J . Experimental and DFT study on the migration and transformation mechanism of nitrogen during the pyrolysis of food waste. Fuel, 2023, 342: 127773

16 Guo S , Liu T , Hui J , Che D , Li X , Sun B , Li S . Effects of calcium oxide on nitrogen oxide precursor formation during sludge protein pyrolysis. Energy, 2019, 189: 116217

17 Yamamoto Y , Sato Y , Ebina T , Yokoyama C , Takahasi S , Mito Y , Tanabe H , Nishiguchi N , Nagaoka K . Separation of high purity indole from coal tar by high pressure crystallization. Fuel, 1991, 70(4): 565–566

18 Shui H , Zhou Y , Li H , Wang Z , Lei Z , Ren S , Pan C , Wang W . Thermal dissolution of Shenfu coal in different solvents. Fuel, 2013, 108: 385–390

19 Ren Q , Zhao C . NO_x and N₂O precursors from biomass pyrolysis: nitrogen transformation from amino acid. Environmental Science & Technology, 2012, 46(7): 4236–4240

20 ZhouXLiuR. A density functional theory study of the pyrolysis mechanisms of indole. Journal of Molecular Structure THEOCHEM, 1999, 461–462: 569–579

21 Lixia L , Zhang R , Wang B , Xie K . Pyrolysis mechanisms of quinoline and isoquinoline with density functional theory. Chinese Journal of Chemical Engineering, 2009, 17(5): 805–813

22 Corval M . An electron impact study of HCN elimination from indole by use of ¹³C labelling. OMS, Organic Mass Spectrometry, 1981, 16(10): 444–447

23 Laskin A , Lifshitz A . Isomerization and decomposition of indole. Experimental results and kinetic modeling. Journal of Physical Chemistry A, 1997, 101(42): 7787–7801

24 Liu J , Zhang X , Hu B , Lu Q , Liu D , Dong C , Yang Y . Formation mechanism of HCN and NH₃ during indole pyrolysis: a theoretical DFT study. Journal of the Energy Institute, 2020, 93(2): 649–657

25 Cheng F , Bayat H , Jena U , Brewer C . Impact of feedstock composition on pyrolysis of low-cost, protein- and lignin-rich biomass: a review. Journal of Analytical and Applied Pyrolysis, 2020, 147: 104780

26 Maliutina K , Tahmasebi A , Yu J . The transformation of nitrogen during pressurized entrained-flow pyrolysis of Chlorella vulgaris. Bioresource Technology, 2018, 262: 90–97

27 Wei Y , Tian H , Liu L , Cheng S , Qing M , Chen Y , Yang H , Yang Y . The effects of alkali metals and alkaline earth metals on the mechanism of N-containing gases production during glutamic acid pyrolysis. Journal of Analytical and Applied Pyrolysis, 2022, 168: 105787

28 Park D C , Day S J , Nelson P F . Nitrogen release during reaction of coal char with O₂, CO₂, and H₂O. Proceedings of the Combustion Institute, 2005, 30(2): 2169–2175

29 Hu E , Zeng X , Ma D , Wang F , Yi X , Li Y , Fu X . Effect of the moisture content in coal on the pyrolysis behavior in an indirectly heated fixed-bed reactor with internals. Energy & Fuels, 2017, 31(2): 1347–1354

30 Liu J , Lu Q , Jiang X , Hu B , Zhang X , Dong C , Yang Y . Theoretical investigation of the formation mechanism of NH₃ and HCN during pyrrole pyrolysis: the effect of H₂O. Molecules. Molecules, 2018, 23(4): 711

31 DenningtonRKeithT AMillamJ M. GaussianView. Version6. Semichem, Inc, Shawnee Mission KS

32 Xu G , Wang H , Yu Y , He H . Role of silver species in H₂-NH₃-SCR of NO_x over Ag/Al₂O₃ catalysts: operando spectroscopy and DFT calculations. Journal of Catalysis, 2021, 395: 1–9

33 Zhao D , Liu H , Lu P , Yu H , Qin M . A DFT study of the mechanism of H transfer during steam gasification. Combustion and Flame, 2020, 219: 327–338

34 Yun H , Kim Y J , Kim S B , Yoon H J , Kwak S K , Lee K B . Preparation of copper-loaded porous carbons through hydrothermal carbonization and ZnCl₂ activation and their application to selective CO adsorption: experimental and DFT calculation studies. Journal of Hazardous Materials, 2022, 426: 127816

35 Liu J , Zhao W , Yang S , Hu B , Xu M , Ma S , Lu Q . Formation mechanism of NO_x precursors during the pyrolysis of 2,5-diketopiperazine based on experimental and theoretical study. Science of the Total Environment, 2021, 801: 149663

36 Liu J , Zhang X , Lu Q , Shaw A , Hu B , Jiang X , Dong C . Mechanism study on the effect of alkali metal ions on the formation of HCN as NO_x precursor during coal pyrolysis. Journal of the Energy Institute, 2019, 92(3): 604–612

37 Liu J , Zhao W , Fan X , Xu M , Zheng S , Lu Q . Effect of alkali metal ions on the formation mechanism of HCN during pyridine pyrolysis. International Journal of Coal Science & Technology, 2021, 8(3): 349–359

38 Jiang D , Li H , Wang S , Cheng X , Bartocci P , Fantozzi F . Insight the CO₂ adsorption onto biomass-pyrolysis derived char via experimental analysis coupled with DFT calculation. Fuel, 2023, 332: 125948

39 Jiang D , Li H , Cheng X , Ling Q , Barati B , Yao Q , Abomohra A , Hu X , Bartocci P . . A mechanism study of methylene blue adsorption on seaweed biomass derived carbon: from macroscopic to microscopic scale. Process Safety and Environmental Protection, 2023, 172: 1132–1143

40 Jiang D , Li H , Cheng X , Abomohra A , Hu Y , Babadi A , Bartocci P , Hu X , Wang S . Chemical process of multiphase system in lignin-biochar co-pyrolysis for enhanced phenol recovery. Fuel Processing Technology, 2023, 250: 107882

41 Jiang D , Yuan C , Cheng X , Wang S , Li H , Yang X . Study on the pyrolysis mechanism of unsaturated fatty acid: a combined density functional theory and experimental study. International Journal of Energy Research, 2022, 46(2): 2029–2040

42 FrischM JTrucksG WSchlegelH BScuseriaG ERobbM ACheesemanJ R. Gaussian 16, Revision A.03. Wallingford CT: Gaussian Inc, 2016

43 Lu T , Chen F . Multiwfn: a multifunctional wavefunction analyzer. Journal of Computational Chemistry, 2012, 33(5): 580–592

44 Poutsma M L . Free-radical thermolysis and hydrogenolysis of model hydrocarbons relevant to processing of coal. Energy & Fuels, 1990, 4(2): 113–131

45 Vernon L W . Free radical chemistry of coal liquefaction: role of molecular hydrogen. Fuel, 1980, 59(2): 102–106

46 WangZShenJLiuXGuoYWangSDengSWuTZhangH. Theoretical study on the formation mechanism of NO_x precursors during the pyrolysis of 2,4-imidazolinediketone. Combustion Science and Technology, Taylor & Francis, 2023, 1–19

47 Wehrli B , Stumm W . Vanadyl in natural waters: adsorption and hydrolysis promote oxygenation. Geochimica et Cosmochimica Acta, 1989, 53(1): 69–77

48 Jiang D , Wang S , Li H , Xu L , Hu X , Barati B , Zheng A . Insight into the mechanism of glycerol dehydration and subsequent pyridine synthesis. ACS Sustainable Chemistry & Engineering, 2021, 9(8): 3095–3103

49 Zhu X , Yang S , Wang L , Liu L , Qian F , Yao W , Zhang S , Chen J . Tracking the conversion of nitrogen during pyrolysis of antibiotic mycelial fermentation residues using XPS and TG-FTIR-MS technology. Environmental Pollution, 2016, 211: 20–27

50 Meng J , Wang J , Yang F , Cheng F . Unveiling the complex effect of Fe₂O₃ on NO_x precursors evolution mechanism during sludge protein pyrolysis based on product characteristics. Fuel, 2024, 358: 130105

51 Liu X , Shen J , Deng S , Wang S , Chen B , Wang Z , Zhang H , Guo Y . Unveiling the role of sodium ion in the conversion of amino acid intermediates and the formation mechanism of NO_x precursors during kitchen waste pyrolysis. Journal of Analytical and Applied Pyrolysis, 2023, 173: 106085

52 Tian F J , Yu J , McKenzie L J , Hayashi J , Li C . Conversion of fuel-N into HCN and NH₃ during the pyrolysis and gasification in steam: a comparative study of coal and biomass. Energy & Fuels, 2007, 21(2): 517–521

53 Ren Q , Zhao C , Chen X , Duan L , Li Y , Ma C . NO_x and N₂O precursors (NH₃ and HCN) from biomass pyrolysis: Co-pyrolysis of amino acids and cellulose, hemicellulose and lignin. Proceedings of the Combustion Institute, 2011, 33(2): 1715–1722

54 Jiang J , Wang Q , Wang Y , Tong W , Xiao B , Xiao B . GC/MS analysis of coal tar composition produced from coal pyrolysis. Bulletin of the Chemical Society of Ethiopia, 2007, 21(2): 229–240