Nitrogen-Doped Porous Carbon Derived from Covalent Triazine Framework for Catalytic Oxidation of Benzyl Alcohol

Overview

Journal Nanomaterials (Basel)

Date 2024 May 10

PMID 38727338

Authors

Xin Pan

Yanan Zhu

Yongchang Yang

Qianqian Zhu

Affiliations

Soon will be listed here.

Abstract

The catalytic oxidation of alcohols is an important transformation in the chemical industry. Carbon materials with a large surface area and N doping show great promise as metal-free catalysts for the reaction. In this study, a rich N-containing covalent triazine framework polymerized by cyanuric chloride and p-phenylenediamine was used to synthesize N-doped porous carbon with the assistance of a pore-forming agent-NaCl. First, the mass ratio of the polymer/NaCl was optimized to 1:9. Then, the influence of the pyrolysis temperatures (700-1000 °C) on the materials was studied in detail. It was found that the carbon materials were gradually exfoliated by molten salt at high temperatures. XRD and Raman characterizations showed them with a certain graphitization. The optimal doped carbon CNN-1-9-900 achieved the highest surface area of 199.03 mg with the largest pore volume of 0.29 cmg. Furthermore, it had a high N content of 9.9 at% with the highest relative proportion of pyridinic/graphitic N. Due to the synergistic effect between the surface area and pyridinic/graphitic N, CNN-1-9-900 showed the best performance for benzyl alcohol oxidation with TBHP at moderate conditions, and the process also worked for its derivatives.

References

Liao L, Li M, Yin Y, Chen J, Zhong Q, Du R . Advances in the Synthesis of Covalent Triazine Frameworks. ACS Omega. 2023; 8(5):4527-4542. PMC: 9909813. DOI: 10.1021/acsomega.2c06961. View

Sun R, Tan B . Covalent Triazine Frameworks (CTFs): Synthesis, Crystallization, and Photocatalytic Water Splitting. Chemistry. 2022; 29(17):e202203077. DOI: 10.1002/chem.202203077. View

Xie Y, Hu W, Wang X, Tong W, Li P, Zhou H . Molten salt induced nitrogen-doped biochar nanosheets as highly efficient peroxymonosulfate catalyst for organic pollutant degradation. Environ Pollut. 2020; 260:114053. DOI: 10.1016/j.envpol.2020.114053. View

Picheau E, Impellizzeri A, Rybkovskiy D, Bayle M, Mevellec J, Hof F . Intense Raman D Band without Disorder in Flattened Carbon Nanotubes. ACS Nano. 2021; 15(1):596-603. DOI: 10.1021/acsnano.0c06048. View

Yang J, Xu M, Wang J, Jin S, Tan B . A Facile Approach to Prepare Multiple Heteroatom-Doped Carbon Materials from Imine-Linked Porous Organic Polymers. Sci Rep. 2018; 8(1):4200. PMC: 5844873. DOI: 10.1038/s41598-018-22507-2. View

Kuhn P, Antonietti M, Thomas A . Porous, covalent triazine-based frameworks prepared by ionothermal synthesis. Angew Chem Int Ed Engl. 2008; 47(18):3450-3. DOI: 10.1002/anie.200705710. View

Jiang Q, Sun L, Bi J, Liang S, Li L, Yu Y . MoS Quantum Dots-Modified Covalent Triazine-Based Frameworks for Enhanced Photocatalytic Hydrogen Evolution. ChemSusChem. 2018; 11(6):1108-1113. DOI: 10.1002/cssc.201702220. View

Iraqui S, Kashyap S, Rashid M . NiFeO nanoparticles: an efficient and reusable catalyst for the selective oxidation of benzyl alcohol to benzaldehyde under mild conditions. Nanoscale Adv. 2022; 2(12):5790-5802. PMC: 9417505. DOI: 10.1039/d0na00591f. View

Cai C, Chen Y, Hu P, Zhu T, Li X, Yu Q . Regulating the Interlayer Spacings of Hard Carbon Nanofibers Enables Enhanced Pore Filling Sodium Storage. Small. 2021; 18(6):e2105303. DOI: 10.1002/smll.202105303. View

10.

Quilez-Bermejo J, Morallon E, Cazorla-Amoros D . Polyaniline-Derived N-Doped Ordered Mesoporous Carbon Thin Films: Efficient Catalysts towards Oxygen Reduction Reaction. Polymers (Basel). 2020; 12(10). PMC: 7602833. DOI: 10.3390/polym12102382. View

11.

Rangraz Y, Heravi M, Elhampour A . Recent Advances on Heteroatom-Doped Porous Carbon/Metal Materials: Fascinating Heterogeneous Catalysts for Organic Transformations. Chem Rec. 2021; 21(8):1985-2073. DOI: 10.1002/tcr.202100124. View

12.

Sun R, Wang X, Wang X, Tan B . Three-Dimensional Crystalline Covalent Triazine Frameworks via a Polycondensation Approach. Angew Chem Int Ed Engl. 2022; 61(15):e202117668. DOI: 10.1002/anie.202117668. View

13.

Li H, Qin F, Yang Z, Cui X, Wang J, Zhang L . New Reaction Pathway Induced by Plasmon for Selective Benzyl Alcohol Oxidation on BiOCl Possessing Oxygen Vacancies. J Am Chem Soc. 2017; 139(9):3513-3521. DOI: 10.1021/jacs.6b12850. View

14.

Zhang Q, Fu M, Ning G, Sun Y, Wang H, Fan X . Co/FeC core-nitrogen doped hollow carbon shell structure with tunable shell-thickness for oxygen evolution reaction. J Colloid Interface Sci. 2020; 580:794-802. DOI: 10.1016/j.jcis.2020.07.031. View

15.

Liu M, Wang X, Liu J, Wang K, Jin S, Tan B . Palladium as a Superior Cocatalyst to Platinum for Hydrogen Evolution Using Covalent Triazine Frameworks as a Support. ACS Appl Mater Interfaces. 2020; 12(11):12774-12782. DOI: 10.1021/acsami.9b21903. View

16.

Cai A, He H, Zhang Q, Xu Y, Li X, Zhang F . Synergistic Effect of N-Doped sp Carbon and Porous Structure in Graphene Gels toward Selective Oxidation of C-H Bond. ACS Appl Mater Interfaces. 2021; 13(11):13087-13096. DOI: 10.1021/acsami.0c21177. View

17.

Li J, Sun H, Wang S, Dong Y, Liu S . Selective oxidation of alcohols by graphene-like carbon with electrophilic oxygen and integrated pyridinic nitrogen active sites. Nanoscale. 2021; 13(30):12979-12990. DOI: 10.1039/d1nr03157k. View

18.

Liu M, Huang Q, Wang S, Li Z, Li B, Jin S . Crystalline Covalent Triazine Frameworks by In Situ Oxidation of Alcohols to Aldehyde Monomers. Angew Chem Int Ed Engl. 2018; 57(37):11968-11972. DOI: 10.1002/anie.201806664. View

19.

Lin Y, Liu Z, Niu Y, Zhang B, Lu Q, Wu S . Highly Efficient Metal-Free Nitrogen-Doped Nanocarbons with Unexpected Active Sites for Aerobic Catalytic Reactions. ACS Nano. 2019; 13(12):13995-14004. DOI: 10.1021/acsnano.9b05856. View

20.

Kicinski W, Dyjak S . Nitrogen-Doped Carbons Derived from Imidazole-Based Cross-Linked Porous Organic Polymers. Molecules. 2021; 26(3). PMC: 7865342. DOI: 10.3390/molecules26030668. View