Hostname: page-component-cd9895bd7-p9bg8 Total loading time: 0 Render date: 2024-12-27T18:45:04.341Z Has data issue: false hasContentIssue false
  • English
  • Français

Green synthesis of functionalized graphene and their use as solid acid catalysts

Published online by Cambridge University Press:  22 October 2018

Xu Zhang Open the ORCID record for Xu Zhang [Opens in a new window] ,
Qiuyu Fan  and
He Yang
Xu Zhang*
Affiliation:
School of Petroleum & Chemical Engineering, Dalian University of Technology, Panjin 124221, China
Qiuyu Fan
Affiliation:
School of Petroleum & Chemical Engineering, Dalian University of Technology, Panjin 124221, China
He Yang
Affiliation:
School of Petroleum & Chemical Engineering, Dalian University of Technology, Panjin 124221, China
*
a)Address all correspondence to this author. e-mail: [email protected]
Get access

Abstract

Here we report a facile and mild synthesis of the sulfonated graphene (PSS-RGO) catalysts by in situ polymerization of sodium p-styrenesulfonate. Graphene sheets can be used as the flat backbones to graft abundant sulfonate groups on both sides. The PSS-RGO catalysts were characterized by 1H Nuclear Magnetic Resonance (1H NMR), energy dispersive spectrometer, Raman spectroscopy, X-ray photoelectron spectroscopy, and so on. The catalytic properties of the PSS-RGO catalysts for the hydrolysis of ethyl acetate and the esterification of acetic acid with ethanol were evaluated, showing that the as-made PSS-RGO catalysts were active for both probe reactions. The possible deactivation mechanism involved in the surface catalysis of the graphene-based acid catalysts has been addressed.

Keywords

sulfonated graphenein situ polymerizationsolid acid catalystesterificationhydrolysis
Type
Article
Information
Journal of Materials Research , Volume 33 , Issue 23 , 14 December 2018 , pp. 3946 - 3952
Copyright
Copyright © Materials Research Society 2018 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

REFERENCES

Clark, J.H.: Solid acids for green chemistry. Acc. Chem. Res. 35, 791–797 (2002).CrossRefGoogle ScholarPubMed
Li, O.L., Ikura, R., and Ishizaki, T.: Hydrolysis of cellulose to glucose over carbon catalysts sulfonated via a plasma process in dilute acids. Green Chem. 19, 4774–4777 (2017).CrossRefGoogle Scholar
Miao, Z., Zhou, J., Zhao, J., Liu, D., Bi, X., Chou, L., and Zhuo, S.: A novel mesoporous sulfated zirconium solid acid catalyst for Friedel-Crafts benzylation reaction. Appl. Surf. Sci. 411, 419–430 (2017).CrossRefGoogle Scholar
Lu, Y., Sun, Z., and Huo, M.: Fabrication of a micellar heteropolyacid with Lewis–Bronsted acid sites and application for the production of 5-hydroxymethylfurfural from saccharides in water. RSC Adv. 5, 30869–30876 (2015).CrossRefGoogle Scholar
Mao, Z., Cao, L., Zhang, F., and Zhang, F.: Microwave-assisted rapid preparation of mesoporous phenolic resin nanospheres toward highly efficient solid acid catalysts. ACS Appl. Mater. Interfaces 10, 28709–28718 (2018).CrossRefGoogle ScholarPubMed
Van Chuc, N., Ngoc Quynh, B., Mascunan, P., Thi Thu Ha, V., Fongarland, P., and Essayem, N.: Esterification of aqueous lactic acid solutions with ethanol using carbon solid acid catalysts: Amberlyst 15, sulfonated pyrolyzed wood and graphene oxide. Appl. Catal., A 552, 184–191 (2018).Google Scholar
Thushari, I. and Babel, S.: Sustainable utilization of waste palm oil and sulfonated carbon catalyst derived from coconut meal residue for biodiesel production. Bioresour. Technol. 248, 199–203 (2018).CrossRefGoogle ScholarPubMed
Thushari, I. and Babel, S.: Preparation of solid acid catalysts from waste biomass and their application for microwave-assisted biodiesel production from waste palm oil. Waste Manage. Res. 36, 719–728 (2018).CrossRefGoogle ScholarPubMed
Cheng, J., Qiu, Y., Zhang, J., Huang, R., Yang, W., and Fan, Z.: Conversion of lipids from wet microalgae into biodiesel using sulfonated graphene oxide catalysts. Bioresour. Technol. 244, 569–574 (2017).CrossRefGoogle ScholarPubMed
Shanhui Zhu, J.W. and Fan, W.: Graphene-based catalysis for biomass conversion. Catal. Sci. Technol. 5, 3845–3858 (2015).Google Scholar
Santos, E.M., de Carvalho Teixeira, A.P., da Silva, F.G., Cibaka, T.E., Araujo, M.H., Coelho Oliveira, W.X., Medeiros, F., Brasil, A.N., de Oliveira, L.S., and Lago, R.M.: New heterogeneous catalyst for the esterification of fatty acid produced by surface aromatization/sulfonation of oilseed cake. Fuel 150, 408–414 (2015).CrossRefGoogle Scholar
Guan, Q., Li, Y., Chen, Y., Shi, Y., Gu, J., Li, B., Miao, R., Chen, Q., and Ning, P.: Sulfonated multi-walled carbon nanotubes for biodiesel production through triglycerides transesterification. RSC Adv. 7, 7250–7258 (2017).CrossRefGoogle Scholar
Zhang, Z., Liao, Y., Mei, Q., Liu, H., Tang, J., Fei, Z., Chen, X., Cui, M., Liu, Q., and Qiao, X.: Quest for a structure-property relationship in sulfonated graphene catalysts for the additive esterification of carboxylic acids and olefins. React. Kinet., Mech. Catal. 122, 901–914 (2017).CrossRefGoogle Scholar
Wang, L., Wang, D., Zhang, S., and Tian, H.: Synthesis and characterization of sulfonated graphene as a highly active solid acid catalyst for the ester-exchange reaction. Catal. Sci. Technol. 3, 1194–1197 (2013).CrossRefGoogle Scholar
Liu, F., Sun, J., Zhu, L., Meng, X., Qi, C., and Xiao, F.: Sulfated graphene as an efficient solid catalyst for acid-catalyzed liquid reactions. J. Mater. Chem. 22, 5495–5502 (2012).CrossRefGoogle Scholar
Valle-Vigon, P., Sevilla, M., and Fuertes, A.B.: Sulfonated mesoporous silica-carbon composites and their use as solid acid catalysts. Appl. Surf. Sci. 261, 574–583 (2012).CrossRefGoogle Scholar
D’Souza, R., Vats, T., Chattree, A., and Siril, P.F.: Graphene supported magnetically separable solid acid catalyst for the single step conversion of waste cooking oil to biodiesel. Renewable Energy 126, 1064–1073 (2018).CrossRefGoogle Scholar
Okamura, M., Takagaki, A., Toda, M., Kondo, J.N., Domen, K., Tatsumi, T., Hara, M., and Hayashi, S.: Acid-catalyzed reactions on flexible polycyclic aromatic carbon in amorphous carbon. Chem. Mater. 18, 3039–3045 (2006).CrossRefGoogle Scholar
Wataniyakul, P., Boonnoun, P., Quitain, A.T., Sasaki, M., Kida, T., Laosiripojana, N., and Shotipruk, A.: Preparation of hydrothermal carbon as catalyst support for conversion of biomass to 5-hydroxymethylfurfural. Catal. Commun. 104, 41–47 (2018).CrossRefGoogle Scholar
Stellwagen, D.R., van der Klis, F., van Es, D.S., de Jong, K.P., and Bitter, J.H.: Functionalized carbon nanofibers as solid-acid catalysts for transesterification. ChemSusChem 6, 1668–1672 (2013).CrossRefGoogle ScholarPubMed
Allen, M.J., Tung, V.C., and Kaner, R.B.: Honeycomb carbon: A review of graphene. Chem. Rev. 110, 132–145 (2010).CrossRefGoogle ScholarPubMed
Novoselov, K.S., Geim, A.K., Morozov, S.V., Jiang, D., Zhang, Y., Dubonos, S.V., Grigorieva, I.V., and Firsov, A.A.: Electric field effect in atomically thin carbon films. Science 306, 666–669 (2004).CrossRefGoogle ScholarPubMed
Zhu, Y.W., Murali, S., Cai, W.W., Li, X.S., Suk, J.W., Potts, J.R., and Ruoff, R.S.: Graphene and graphene oxide: Synthesis, properties, and applications. Adv. Mater. 22, 3906–3924 (2010).CrossRefGoogle ScholarPubMed
Yu, X., Cheng, H., Zhang, M., Zhao, Y., Qu, L., and Shi, G.: Graphene-based smart materials. Nat. Rev. Mater. 2, 17046 (2017).CrossRefGoogle Scholar
Ji, J., Zhang, G., Chen, H., Wang, S., Zhang, G., Zhang, F., and Fan, X.: Sulfonated graphene as water-tolerant solid acid catalyst. Chem. Sci. 2, 484–487 (2011).CrossRefGoogle Scholar
Mukherjee, A., Kang, J., Kuznetsov, O., Sun, Y., Thaner, R., Bratt, A.S., Lomeda, J.R., Kelly, K.F., and Billups, W.E.: Water-soluble graphite nanoplatelets formed by Oleum exfoliation of graphite. Chem. Mater. 23, 9–13 (2011).CrossRefGoogle Scholar
Mylvaganam, K. and Zhang, L.: In situ polymerization on graphene surfaces. J. Phys. Chem. C 117, 2817–2823 (2013).CrossRefGoogle Scholar
Wu, T., Xu, X., Zhang, L., Chen, H., Gao, J., and Liu, Y.: A polyaniline/graphene nanocomposite prepared by in situ polymerization of polyaniline onto polyanion grafted graphene and its electrochemical properties. RSC Adv. 4, 7673–7681 (2014).CrossRefGoogle Scholar
Mylvaganam, K. and Zhang, L.: In situ polymerization on graphene surfaces. J. Phys. Chem. C 117, 2817–2823 (2013).CrossRefGoogle Scholar
Kan, L., Xu, Z., and Gao, C.: General avenue to individually dispersed graphene oxide-based two-dimensional molecular brushes by free radical polymerization. Macromolecules 44, 444–452 (2011).CrossRefGoogle Scholar
Hummers, W.S. and Offeman, R.E.: Preparation of graphitic oxide. J. Am. Chem. Soc. 80, 1339 (1958).CrossRefGoogle Scholar
Kovtyukhova, N.I., Ollivier, P.J., Martin, B.R., Mallouk, T.E., Chizhik, S.A., Buzaneva, E.V., and Gorchinskiy, A.D.: Layer-by-layer assembly of ultrathin composite films from micron-sized graphite oxide sheets and polycations. Chem. Mater. 11, 771–778 (1999).CrossRefGoogle Scholar
He, X., Peng, Z., Yu, N., Han, J., and Wu, C.: Poly(sodium 4-styrenesulfonate) modified carbon nanoparticles by a thermo-mechanical technique and its reinforcement in natural rubber latex. Compos. Sci. Technol. 68, 3027–3032 (2008).CrossRefGoogle Scholar
Coughlin, J.E., Reisch, A., Markarian, M.Z., and Schlenoff, J.B.: Sulfonation of polystyrene: Toward the “ideal” polyelectrolyte. J. Polym. Sci., Part A: Polym. Chem. 51, 2416–2424 (2013).CrossRefGoogle Scholar
Zhang, X., Wang, Z., Li, S., Wang, C., and Qiu, J.: Recyclable catalyst for catalytic hydrogenation of phenylacetylene by coupling Pd nanoparticles with highly compressible graphene aerogels. RSC Adv. 4, 59977–59980 (2014).CrossRefGoogle Scholar
Lazzeri, M. and Mauri, F.: Nonadiabatic Kohn anomaly in a doped graphene monolayer. Phys. Rev. Lett. 97, 266407–266411 (2006).CrossRefGoogle Scholar
Wu, T., Wang, G., Dong, Q., Zhan, F., Zhang, X., Li, S., Qiao, H., and Qiu, J.: Starch derived porous carbon nanosheets for high-performance photovoltaic capacitive deionization. Environ. Sci. Technol. 51, 9244–9251 (2017).CrossRefGoogle ScholarPubMed
Stankovich, S., Dikin, D.A., Piner, R.D., Kohlhaas, K.A., Kleinhammes, A., Jia, Y., Wu, Y., Nguyen, S.T., and Ruoff, R.S.: Synthesis of graphene-based nanosheets via chemical reduction of exfoliated graphite oxide. Carbon 45, 1558–1565 (2007).CrossRefGoogle Scholar
Mo, X., Lopez, D., Suwannakarn, K., Liu, Y., Lotero, E., Goodwinjr, J., and Lu, C.: Activation and deactivation characteristics of sulfonated carbon catalysts. J. Catal. 254, 332–338 (2008).CrossRefGoogle Scholar
Supplementary material: File

Zhang et al. supplementary material

Zhang et al. supplementary material 1

Download Zhang et al. supplementary material(File)
File 1.7 MB