Abstract
Green chemistry has fostered research on recyclable, insoluble and easily separable heterogeneous catalysts. Carbon materials are widely used for renewable energy and environmental studies. Here, we review the synthesis, properties and applications of carbon solid acids in the form of biomass, polymers, and carbon/silica-based catalysts. We show in particular that mesoporosity has a major role in catalysis, notably when bulk materials are transformed into valuable products.
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Chen T, Peng L, Yu X, He L (2018) Magnetically recyclable cellulose derived carbonaceous solid acid catalyzed the biofuel 5-ethoxymethylfurfural synthesis from renewable carbohydrates. Fuel 219:344–352. https://doi.org/10.1016/j.fuel.2018.01.129
Cui X, Antonietti M, Yu SH (2006) Structural effects of Iron oxide nanoparticles and iron ions on the hydrothermal carbonization of starch and rice carbohydrates. Small 2:756–759. https://doi.org/10.1002/smll.200600047
Demir-Cakan R, Baccile N, Antonietti M, Titirici M-M (2009) Carboxylate-rich carbonaceous materials via one-step hydrothermal carbonization of glucose in the presence of acrylic acid. Chem Mater 21:484–490. https://doi.org/10.1021/cm802141h
Demir-Cakan R, Makowski P, Antonietti M, Goettmann F, Titirici M-M (2010) Hydrothermal synthesis of imidazole functionalized carbon spheres and their application in catalysis. Catal Today 150:115–118. https://doi.org/10.1016/j.cattod.2009.05.003
Dong X, Jiang Y, Shan W, Zhang MA (2016) A novel highly ordered mesoporous carbon based solid for synthesis of bisphenol-A. RSC Adv 6:17118–17124. https://doi.org/10.1039/C5RA24966J
Guo HX, Lian YF, Yan LL, Qi XH, Smith RL Jr (2013) Cellulose derived superparamagnetic carbonaceous solid acid catalyst for cellulose hydrolysis in an ionic liquid or aqueous reaction system. Green Chem 15:2167–2174. https://doi.org/10.1039/C3GC40433A
Gupta P, Paul S (2011) Amorphous carbon-silica composites bearing sulfonic acid as solid acid catalysts for the chemoselective protection of aldehydes as 1,1-diacetates and for N- O- and S- acylations. Green Chem 13:2365–2372. https://doi.org/10.1039/c0gc00900h
Gupta P, Paul S (2012) Sulfonated carbon/silica composite functionalized lewis acids for one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles, 3,4-dihydropyrimidin-2(1H)-ones and for Michael addition of indole to α, β-unsaturated ketones. J Mol Catal A Chem 352:75–80. https://doi.org/10.1016/j.molcata.2011.10.016
Gupta P, Paul S (2014) Sulfonated carbon/silica composites: heterogeneous catalysts for the one-pot synthesis of Hantzsch 1,4-dihydropyridines, 2,4,5-trisubstituted imidazoles and 2-arylbenzimidazoles. Curr Catal 3:53–64
Gupta P, Kour M, Paul S, Clark JH (2014) Ionic liquid coated sulfonated carbon/silica composites: novel heterogeneous catalysts for organic syntheses in water. RSC Adv 4:7461–7470. https://doi.org/10.1039/c3ra45229h
Hara M, Yoshida T, Takagaki A, Takata T, Kondo JN, Domen K, Hayashi S (2004) A carbon material as a strong protonic acid. Angew Chem Int Ed 43:2955–2958. https://doi.org/10.1002/anie.200453947
Hu B, Yu S-H, Wang K, Liu L, Xu X-W (2008) Functional carbonaceous materials from hydrothermal carbonization of biomass: an effective chemical process. Dalton Trans 40:5414–5423. https://doi.org/10.1039/B804644C
Janaun J, Safie NN, Siambun NJ (2016) Synthesis, characterization and catalytic activity of carbon-silica hybrid catalyst from rice straw. AIP Conf Proc 1756:090007
Jia R, Ren J, Liu X, Lu G, Wang Y (2014) Design and synthesis of sulfonated carbons with amphiphilic properties. J Mater Chem A 2:11195–11201. https://doi.org/10.1039/c4ta01836b
Jun S, Joo SH, Ryoo R, Kruk M, Jaroniec M, Liu Z, Ohsuna T, Terasaki O (2000) Synthesis of new, nanoporous carbon with hexagonally ordered mesostructure. J Am Chem Soc 122:10712–10713. https://doi.org/10.1021/ja002261e
Karimi B, Mirzaei HM, Behzadnia H, Vali H (2015) Novel ordered mesoporous carbon based sulfonic acid as an efficient catalyst in the selective dehydration of fructosed into 5-HMF: the role of solvent and surface chemistry. ACS Appl Mater Interfaces 7:19050–19059. https://doi.org/10.1021/acsami.5b03985
Khatri PK, Manchanda M, Ghosh IK, Jain SL (2015) Polymer impregnated sulfonated carbon composite solid acid catalyst for alkylation of phenol with methyl-tert-butyl ether. RSC Adv 5:3286–3290. https://doi.org/10.1039/c4ra11033a
Kumar H, Alén R (2016) Microwave assisted esterification of Tall oil fatty acids with methanol using lignin based solid catalyst. Energy Fuels 30:9451–9455. https://doi.org/10.1021/acs.energyfuels.6b01718
Laohapornchaiphan J, Smith CB, Smith SM (2017) One step preparation of carbon based solid acid catalyst from water hyacinth leaves for esterification of oleic acid and dehydration of xylose. Chem Asian J 12:3178–3186. https://doi.org/10.1002/asia.201701369
Li T, Shen S, Cai B, Wang Y, Peng X, Li Y (2016) High performance carbon based solid acid prepared by environmental and efficient recycling of PVC waste for cellulose hydrolysis. RSC Adv 6:91921–91929. https://doi.org/10.1039/c6ra13358d
Li X, Shi J, Wang J, Duan X, Chen G, Guan Q, Li X, Lei T (2017) Preparation of carbon based magnetic solid acid catalyst from various carbon sources and characterization of its catalytic performance. Bioresoures 12:7525–7538. https://doi.org/10.15376/biores.12.4.7525-7538
Li X, Shu F, He C, Liu S, Leksawasdi N, Wang Q, Qi Q, Alam Md AL, Yuanbd Z, Gaoe Y (2018) Preparation and investigation of highly selective solid acid catalysts with sodium lignosulfonate for hydrolysis of hemicelluloses in corncob. RSC Adv 8:10922–10929. https://doi.org/10.1039/c7ra13362f
Liang X (2015) Novel magnetic carbon based solid acid for alkylation of benzene and dodecene. Chem Eng J 264:251–257. https://doi.org/10.1016/j.cej.2014.11.105
Lin Q-X, Zhang C-H, Wang X-H, Cheng B-G, Mai N, Ren J-L (2019) Impact of activation on properties of carbon based solid acid catalysts for the hydrothermal conversion of xylose and hemicelluloses. Catal Today 319:31–40. https://doi.org/10.1016/j.cattod.2018.03.070
Liu F, Kong W, Wang L, Yi X, Noshadi I, Zheng A, Qi C (2015a) Efficient biomass transformations catalyzed by graphene like nanoporous carbons functionalized with strong acid ionic liquids and sulfonic groups. Green Chem 17:480–489. https://doi.org/10.1039/c4gc01052c
Liu R-L, Gao XY, An L, Ma J, Zhang JF, Zhang ZQ (2015b) Fabrication of magnetic carbonaceous solid acids from banana peel for the esterification of oleic acid. RSC Adv 5:93858–93866. https://doi.org/10.1039/c5ra15767f
Liu WJ, Jiang H, Yu HQ (2015c) Development of biochar based functional materials: toward a sustainable platform carbon material. Chem Rev 115:12251–12285. https://doi.org/10.1021/acs.chemrev.5b00195
Liu F, Li B, Liu C, Kong W, Yi X, Zheng A, Qi C (2016a) Template free synthesis of porous carbonaceous solid acids with controllable acid sites and their excellent activity for catalyzing the synthesis of biofuels and fine chemicals. Catal Sci Technol 6:2995–3007. https://doi.org/10.1039/C5CY01226K
Liu H, Chen J, Chen L, Xu Y, Guo X, Fang D (2016b) Carbon nanotube based solid sulfonic acids as catalysts for production of fatty acid methyl ester via transesterification and esterification. ACS Sustain Chem Eng 4:3140–3150. https://doi.org/10.1021/acssuschemeng.6b00156
Liu Y, Liu W, Wang L, Su M, Liu F (2018) Efficient hydrolysis of cyclohexyl acetate to cyclohexanol catalyzed by dual –SO3H-functionalized heteropolyacid-based solid acids. Ind Eng Chem Res 57:5207–5214. https://doi.org/10.1021/acs.iecr.8b00240
Ma J, Peng X, Zhong L, Sun R (2018) Sulfonation of carbonized xylan-type hemicellulose: a renewable and effective biomass based biocatalyst for the synthesis of O– and N– heterocycles. New J Chem 42:9140–9150. https://doi.org/10.1039/C8NJ01329B
Mesquita LMM, Pinto RMA, Salvador JAR, Clark JH, Budarin VL (2015) Starbon@400-HSO3: a green mesoporous carbonaceous solid acid catalyst for the Ritter reaction. Catal Commun 69:170–173. https://doi.org/10.1016/j.catcom.2015.06.010
Nakajima K, Hara M (2012) Amorphous carbon with SO3H groups as a solid brønsted acid catalyst. ACS Catal 2:1296–1304. https://doi.org/10.1021/cs300103k
Nakajima K, Okamura M, Kondo JN, Domen K, Tatsumi T, Hayashi S, Hara M (2009) Amorphous carbon bearing sulfonic acid groups in mesoporous silica as a selective catalyst. Chem Mater 21:186–193. https://doi.org/10.1021/cm801441c
Nakhate AV, Yadav GD (2016) Synthesis and characterization of sulfonated carbon based Graphene oxide monolith by solvothermal carbonization for esterification and unsymmetrical ether formation. ACS Sustain Chem Eng. 4:1963–1973. https://doi.org/10.1021/acssuschemeng.5b01205
Okamura M, Takagaki A, Toda M, Kondo JN, Tatsumi T, Domen K, Hara M, Hayashi S (2006) Acid catalyzed reactions on flexible polycyclic aromatic carbon in amorphous carbon. Chem Mater 18:3039–3045. https://doi.org/10.1021/cm0605623
Ouyang S, Kuang X, Xu Q, Yi D (2014) Preparation of a carbon based solid acid with high density via a novel method. J Mater Sci Chem Eng 2:4–8. https://doi.org/10.4236/msce.2014.26002
Pang Q, Wang L, Yang H, Jia L, Pan X, Qiu C (2014) Cellulose derived carbon bearing –Cl and –SO3H groups as a highly selective catalyst for the hydrolysis of cellulose to glucose. RSC Adv 4:41212–41218. https://doi.org/10.1039/c4ra05520a
Patil SKR, Lund CRF (2011) Formation and growth of humans via aldol addition and condensation during acid catalyzed conversion of 5-hydroxymethylfurfural. Energy Fuels 25:4745–4755. https://doi.org/10.1021/ef2010157
Qi W, He C, Wang Q, Liu S, Yu Q, Wang W (2018) Carbon based solid acid pretreatment in Corncob saccharification: specific xylose production and efficient enzymatic hydrolysis. ACS Sustain Chem Eng. 6:3640–3648. https://doi.org/10.1021/acssuschemeng.7b03959
Reddy TVK, Rani GS, Prasad RBN, Devi BLAP (2015) Green recyclable SO3H carbon catalyst for the selective synthesis of isomannide based fatty acid monoesters as non ionic bio-surfactants. RSC Adv 5:40997–41005. https://doi.org/10.1039/c5ra03605d
Russo PA, Antunes MM, Neves P, Wiper PV, Fazio E, Neri F, Barreca F, Mafra L, Pillinger M, Pinna N, Valente AA (2014) Mesoporous carbon-silica acid catalyst for producing useful bio-products within the sugar platform of biorefineries. Green Chem 16:4292–4305. https://doi.org/10.1039/c4gc01037j
Savaliya ML, Dholakiya BZ (2015) A simpler and highly efficient protocol for the preparation of biodiesel from soap stock oil using a BBSA catalyst. RSC Adv 5:74416–74424. https://doi.org/10.1039/C5RA13422F
Sevilla M, Fuertes AB (2009) The production of carbon materials by hydrothermal carbonization of cellulose. Carbon 47:2281–2289. https://doi.org/10.1016/j.carbon.2009.04.026
Su TC, Fang Z, Zhang F, Luo J, Li XK (2015) Hydrolysis of selected tropical plant wastes catalyzed by a magnetic carbonaceous acid with microwave. Sci Rep 5:17538–17542. https://doi.org/10.1038/srep17538
Suganuma S, Nakajima K, Kitano M, Yamaguchi D, Kato H, Hayashi S, Hara M (2008) Hydrolysis of cellulose by amorphous carbon bearing SO3H, COOH and OH groups. J Am Chem Soc 131:12787–12793. https://doi.org/10.1021/ja803983h
Sukma LPP, Qian EW (2017) Fabrication of weak acid functionalized mesoporous carbon solid acid from tannic acid and its use for saccharification of cellulose. Environ Prog Sustain Energy. https://doi.org/10.1002/ep.12709
Sun X, Li Y (2004) Ga3O3 and GaN semiconductor hollow spheres. Angew Chem Int Ed 43:3827–3831. https://doi.org/10.1002/anie.200353212
Thombal RS, Jadhav AR, Jadhav VH (2015) Biomass derived β-cyclodextrin SO3H as a solid acid catalyst for esterification of carboxylic acids with alcohols. RSC Adv 5:12981–12986. https://doi.org/10.1039/c4ra16699j
Titirici MM, Thomas A, Antonietti M (2007a) Back in the black: hydrothermal carbonization of plant material as an efficient chemical 22 process to treat the CO2 problem? New J Chem 31:787–789. https://doi.org/10.1039/B616045J
Titirici MM, Thomas A, Yu SH, Muller JO, Antonietti M (2007b) A direct synthesis of mesoporous carbons with bicontinuous pore morphology from crude plant material by hydrothermal carbonization. Chem Mater 19:4205–4212. https://doi.org/10.1021/cm0707408
Titirici MM, Antonietti M, Baccile N (2008) Hydrothermal carbon from biomass: a comparison of the local structure from poly-to monosaccharides and pentoses/hexoses. Green Chem 10:1204–1212. https://doi.org/10.1039/b807009a
Titirici M-M, White RJ, Falcoa C, Sevilla M (2012) Black perspectives for a green future: hydrothermal carbons for environment protection and energy storage. Energy Environ Sci 5:6796–6822. https://doi.org/10.1039/c2ee21166a
Toda M, Takagaki A, Okamura M, Kondo JN, Hayashi S, Domen K, Hara M (2005) Green Chemistry: biodiesel made with sugar catalyst. Nature 438:178. https://doi.org/10.1038/438178a
Wang Y, Wang D, Tan M, Jiang B, Zheng J, Tsubaki N, Wu M (2015) Monodispersed hollow SO3H-functionalized carbon/silica as efficient solid acid catalyst for esterification of oleic acid. ACS Appl Mater Interfaces 7:26767–26775. https://doi.org/10.1021/acsami.5b08797
Wang K, Jiang J, Xu J, Feng J, Wang J (2016) Effective saccharification of holocellulose over multifunctional sulfonated char with fused ring structures under microwave irradiation. RSC Adv 6:14164–14170. https://doi.org/10.1039/c5ra28113j
Wang W, Lu P, Tang H, Ma Y, Yang XA (2017) Zanthoxylum bungeanum seed oil based carbon solid acid catalyst for the production of biodiesel. New J Chem 41:9256–9261. https://doi.org/10.1039/C7NJ01271C
Yamaguchi D, Watanabe K, Fukumi S (2016) Hydrolysis of cellulose by a mesoporous carbon-Fe2(SO4)3/γ-Fe2O3 nanoparticle based solid acid catalyst. Sci Rep 6:20327. https://doi.org/10.1038/srep20327
Yu SH, Cui XJ, Li LL, Li K, Yu B, Antonietti M, Colfen H (2004) From starch to Metal/carbon hybrid nanostructures: hydrothermal metal-catalyzed carbonization. Adv Mater 16:1636–1640. https://doi.org/10.1002/adma.200400522
Zeng D, Zhang Q, Chen S, Liu S, Wang G (2016) Synthesis porous carbon based solid acid from rice husk for esterification of fatty acids. Microporous Mesoporous Mater 219:54–58. https://doi.org/10.1016/j.micromeso.2015.07.028
Zhan S, Tao X, Cai L, Liu X, Liu T (2014) The carbon material functionalized with NH2+ and SO3H groups catalyzed esterification with high activity and selectivity. Green Chem 16:4649–4653. https://doi.org/10.1039/c4gc01395f
Zhang BH, Ren JW, Liu XH, Guo YL, Guo Y, Lu GZ, Wang YQ (2010) Novel sulfonated carbonaceous materials from p-toluenesulfonic acid/glucose as a high-performance solid acid catalyst. Catal Commun 11:629–632. https://doi.org/10.1016/j.catcom.2010.01.010
Zhang C, Wang H, Liu F, Wang L, He H (2013) Magnetic core shell Fe3O4@C-SO3H nanoparticle catalyst for hydrolysis of cellulose. Cellulose 20:127–134. https://doi.org/10.1007/s10570-012-9839-5
Zhang F, Fang Z, Wang YT (2015) Biodiesel production direct from high acid value oil with a novel magnetic carbonaceous acid. Appl Energy 155:637–647. https://doi.org/10.1016/j.apenergy.2015.06.044
Zhang F, Tian X, Shahac M, Yang W (2017) Synthesis of magnetic carbonaceous acids derived from hydrolysates of Jatropha hulls for catalytic biodiesel production. RSC Adv 7:11403–11413. https://doi.org/10.1039/c6ra28796d
Zhang H, Lu Y, Wang Y, Zhang X, Wang T (2018) D-glucosamine production from chitosan hydrolyzation over a glucose derived solid acid catalyst. RSC Adv 8:5608–5613. https://doi.org/10.1039/c7ra12490b
Zhao D, Feng J, Huo Q, Melosh N, Fredrickson HG, Chmelka BF, Stucky GD (1998a) Triblock copolymer synthesis of mesoporous silica with periodic 50 to 300 angstrom pores. Science 279:548–552. https://doi.org/10.1126/science.279.5350.548
Zhao D, Huo Q, Freng J, Chmelka BF, Stucky GD (1998b) Nonionic triblock and star diblock copolymer and oligomeric surfactant syntheses of highly ordered, hydrothermally stable, mesoporous silica structures. J Am Chem Soc 120:6024–6036. https://doi.org/10.1021/ja974025i
Zhong R, Liao Y, Peng L, Iacobescu RI, Pontikes Y, Shu R, Ma L, Sels BF (2018) Silica-carbon nanocomposite acid catalyst with large mesopore interconnectivity by vapour-phase assisted hydrothermal treatment. ACS Sustain Chem Eng. 6:7859–7870. https://doi.org/10.1021/acssuschemeng.8b01003
Acknowledgements
One of the authors Dr. Princy Gupta gratefully acknowledges the financial support from University Grants Commission (Ministry of Human Resource Development, Govt. of India) under UGC-BSR Start-up Grant No. F.30-35/2017(BSR) and the financial support from Central University of Jammu under Minor Research Project No. CUJ/Acad/Proj-CHE/2017/105.
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Mahajan, A., Gupta, P. Carbon-based solid acids: a review. Environ Chem Lett 18, 299–314 (2020). https://doi.org/10.1007/s10311-019-00940-7
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DOI: https://doi.org/10.1007/s10311-019-00940-7