Micro-sized hydrothermal carbon supporting metal oxide nanoparticles as efficient catalyst for mono-dehydration of sugar alcohol
Received date: 07 Jun 2019
Accepted date: 02 Dec 2019
Published date: 15 Oct 2022
Copyright
Most known catalytic dehydration of sugar alcohols such as D-sorbitol and D-mannitol can only produce di-dehydrated forms as major product, but mono-dehydrated products are also useful chemicals. Moreover, both di- and mono-dehydration demand a high temperature (150°C or higher), which deserves further attentions. To improve the mono-dehydration efficiency, a series of metal-containing hydrothermal carbonaceous materials (HTC) are prepared as catalyst in this work. Characterization reveals that the composition of preparative solution has a key influence on the morphology of HTC. In transformation of D-sorbitol, all HTC catalysts show low conversions in water regardless of temperature, but much better outputs are obtained in ethanol, especially at a higher temperature. When D-mannitol is selected as substrate, moderate to high conversions are obtained in both water and ethanol. On the other hand, high mono-dehydration selectivity is obtained for both sugar alcohols by using all catalysts. The origin of mono-dehydration selectivity and role of carbon component in catalysis are discussed in association with calculations. This study provides an efficient, mild, eco-friendly, and cost-effective system for mono-dehydration of sugar alcohols, which means a lot to development in new detergents or other fine chemicals.
Key words: hydrothermal carbon; morphology; catalyst; mono-dehydration; sugar alcohol
Cheng PAN , Chao FAN , Wanqin WANG , Teng LONG , Benhua HUANG , Donghua ZHANG , Peigen SU , Aqun ZHENG , Yang SUN . Micro-sized hydrothermal carbon supporting metal oxide nanoparticles as efficient catalyst for mono-dehydration of sugar alcohol[J]. Frontiers in Energy, 2022 , 16(5) : 822 -839 . DOI: 10.1007/s11708-020-0677-0
1 |
Shen Y. Carbon dioxide bio-fixation and wastewater treatment via algae photochemical synthesis for biofuels production. RSC Advances, 2014, 91: 49672–49722
|
2 |
Alonso D M, Bond J Q, Dumesic J A. Catalytic conversion of biomass to biofuels. Green Chemistry, 2010, (9): 1493–1513
|
3 |
Zhang J, Li J, Wu S B, Liu Y. Advances in the catalytic production and utilization of sorbitol. Industrial & Engineering Chemistry Research, 2013, 2(34): 11799–11815
|
4 |
Zhang H, Rindt C C M, Smeulders D M J, Nedea S V. Nanoscale heat transfer in carbon nanotubes–sugar alcohol composite as heat storage materials. The Journal of Physical Chemistry C, 2016, 0(38): 21915–21924
|
5 |
Zhang M, Lai W, Su L, Wu G. Effect of catalyst on the molecular structure and thermal properties of isosorbide polycarbonates. Industrial & Engineering Chemistry Research, 2018, 7(14): 4824–4831
|
6 |
Ćirin D M, Poša M M, Krstonošić V S. Interactions between sodium cholate or sodium deoxycholate and nonionic surfactant (Tween 20 or Tween 60) in aqueous solution. Industrial & Engineering Chemistry Research, 2012, 1(9): 3670–3676
|
7 |
Baggett N, Mosihuzzaman M, Webber J M. Synthesis of some monoacetals of 1,4-anhydro-D-mannitol. Carbohydrate Research, 1983, 116(1): 49–60
|
8 |
Flèche G, Huchette M. Isosorbide. Preparation, properties and chemistry. Starch, 1986, 38(1): 26–30
|
9 |
Rusu O A, Hoelderich W F, Wyart H, Ibert M. Metal phosphate catalyzed dehydration of sorbitol under hydrothermal conditions. Applied Catalysis B: Environmental, 2015, 176–177: 139–149
|
10 |
Tang Z C, Yu D H, Sun P, Li H, Huang H. Phosphoric acid modified Nb2O5: a selective and reusable catalyst for dehydration of sorbitol to isosorbide. Bulletin of the Korean Chemical Society, 2010, 31(12): 3679–3683
|
11 |
Kobayashi H, Yokoyama H, Feng B, Fukuoka A. Dehydration of sorbitol to isosorbide over H-beta zeolites with high Si/Al ratios. Green Chemistry, 2015, 17(5): 2732–2735
|
12 |
Cubo A, Iglesias J, Morales G, Melero J A, Moreno J, Sánchez-Vázquez R. Dehydration of sorbitol to isosorbide in melted phase with propyl-sulfonic functionalized SBA-15: influence of catalyst hydrophobization. Applied Catalysis A: General, 2017, 531: 151–160
|
13 |
Zhang J, Wang L, Liu F, Meng X, Mao J, Xiao F S. Enhanced catalytic performance in dehydration of sorbitol to isosorbide over a superhydrophobic mesoporous acid catalyst. Catalysis Today, 2015, 242: 249–254
|
14 |
Robinson J M, Wadle A M, Reno M D, Kidd R, Barrett Hinsz S R, Urquieta J. Solvent- and microwave-assisted dehydrations of polyols to anhydro and dianhydro polyols. Energy & Fuels, 2015, 29(10): 6529–6535
|
15 |
Yamaguchi A, Hiyoshi N, Sato O, Shirai M. Sorbitol dehydration in high temperature liquid water. Green Chemistry, 2011, 13(4): 873–881
|
16 |
Yokoyama H, Kobayashi H, Hasegawa J, Fukuoka A. Selective dehydration of mannitol to isomannide over Hβ zeolite. ACS Catalysis, 2017, 7(7): 4828–4834
|
17 |
Okuhara T. Water-tolerant solid acid catalysts. Chemical Reviews, 2002, 102(10): 3641–3666
|
18 |
Dabbawala A A, Mishra D K, Huber G W, Hwang J S. Role of acid sites and selectivity correlation in solvent free liquid phase dehydration of sorbitol to isosorbide. Applied Catalysis A: General, 2015, 492: 252–261
|
19 |
Polaert I, Felix M C, Fornasero M, Marcotte S, Buvat J C, Estel L. A greener process for isosorbide production: kinetic study of the catalytic dehydration of pure sorbitol under microwave. Chemical Engineering Journal, 2013, 222: 228–239
|
20 |
Clancy A J, Bayazit M K, Hodge S A, Skipper N T, Howard C A, Shaffer M S P. Charged carbon nanomaterials: redox chemistries of fullerenes, carbon nanotubes, and graphenes. Chemical Reviews, 2018, 118(16): 7363–7408
|
21 |
Lee J S, Kim S I, Yoon J C, Jang J H. Chemical vapor deposition of mesoporous graphene nanoballs for supercapacitor. ACS Nano, 2013, 7(7): 6047–6055
|
22 |
Moothi K, Simate G S, Falcon R, Iyuke S E, Meyyappan M. Carbon nanotube synthesis using coal pyrolysis. Langmuir, 2015, 31(34): 9464–9472
|
23 |
Zhu L, Zhao X, Li Y, Yu X, Li C, Zhang Q. High-quality production of graphene by liquid-phase exfoliation of expanded graphite. Materials Chemistry and Physics, 2013, 137(3): 984–990
|
24 |
Ulstrup S, Lacovig P, Orlando F, Lizzit D, Bignardi L, Dalmiglio M, Bianchi M, Mazzola F, Baraldi A, Larciprete R, Hofmann P, Lizzit S. Photoemission investigation of oxygen intercalated epitaxial graphene on Ru(0001). Surface Science, 2018, 678: 57–64
|
25 |
Li S, Jia Z, Li Z, Li Y, Zhu R. Synthesis and characterization of mesoporous carbon nanofibers and its adsorption for dye in wastewater. Advanced Powder Technology, 2016, 27(2): 591–598
|
26 |
Salimi M, Balou S, Kohansal K, Babaei K, Tavasoli A, Andache M. Optimizing the preparation of meso- and microporous canola stalk-derived hydrothermal carbon via response surface methodology for methylene blue removal. Energy & Fuels, 2017, 31(11): 12327–12338
|
27 |
Zhao R, Wang Y, Li X, Sun B, Li Y, Ji H, Qiu J, Wang C. Surface activated hydrothermal carbon-coated electrospun PAN fiber membrane with enhanced adsorption properties for herbicide. ACS Sustainable Chemistry & Engineering, 2016, 4(5): 2584–2592
|
28 |
Qin Y, Zhang L, An T. Hydrothermal carbon-mediated Fenton-like reaction mechanism in the degradation of alachlor: direct electron transfer from hydrothermal carbon to Fe(III). ACS Applied Materials & Interfaces, 2017, 9(20): 17115–17124
|
29 |
Zhang P, Song X, Yu C, Gui J, Qiu J. Biomass-derived carbon nanospheres with turbostratic structure as metal-free catalysts for selective hydrogenation of o-chloronitrobenzene. ACS Sustainable Chemistry & Engineering, 2017, 5(9): 7481–7485
|
30 |
Bhattacharjee R, Datta A. Role of carbon support for subnanometer gold-cluster-catalyzed disiloxane synthesis from hydrosilane and water. The Journal of Physical Chemistry C, 2017, 121(37): 20101–20112
|
31 |
Johari P, Shenoy V B. Modulating optical properties of graphene oxide: role of prominent functional group. ACS Nano, 2011, 5(9): 7640–7647
|
32 |
Ahmadi M, Mistry H, Roldan Cuenya B. Tailoring the catalytic properties of metal nanoparticles via support interactions. The Journal of Physical Chemistry Letters, 2016, 7(17): 3519–3533
|
33 |
Luo Z, Lu Y, Somers L A, Johnson A T C. High yield preparation of macroscopic graphene oxide membranes. Journal of the American Chemical Society, 2009, 131(3): 898–899
|
34 |
Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Scalmani G, Barone V, Mennucci B, Petersson G A, Nakatsuji H, Caricato M, Li X, Hratchian H P, Izmaylov A F, Bloino J, Zheng G, Sonnenberg J L, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery J A Jr, Peralta J E, Ogliaro F, Bearpark M, Heyd J J, Brothers E, Kudin K N, Staroverov V N, Kobayashi R, Normand J, Raghavachary K, Rendell A, Burant J C, Iyengar S S, Tomasi J, Cossi M, Rega N, Millam N J, Klene M, Knox J E, Cross J B, Bakken V, Amado C, Jaramillo J, Gomperts R, Stratmann R E, Yazyev O, Austin A J, Cammi R, Pomelli C, Ochterski J W, Martin R L, Morokuma K, Zakrzewski V G, Voth G A, Salvador P, Dannenberg J J, Dapprich S, Daniels A D, Farkas Ö, Foresman J B, Ortiz J V, Cioslowski J, Fox D J. Gaussian 09W Revision D.01. Wallingford, CT: Gaussian, Inc., 2013
|
35 |
van Alem K, Sudhölter E J R, Zuilhof H. Quantum chemical calculations on α-substituted ethyl cations: a comparison between B3LYP and Post-HT method. The Journal of Physical Chemistry A, 1998, 102(52): 10860–10868
|
36 |
Zhao Z P, Li M S, Zhang J Y, Li H N, Zhu P P, Liu W F. New chiral catalytic membranes created by coupling UV-photografting with covalent immobilization of salen-Co(III) for hydrolytic kinetic resolution of racemic epichlorohydrin. Industrial & Engineering Chemistry Research, 2012, 51(28): 9531–9539
|
37 |
Chen H R, Shi J L, Zhang W H, Ruan M L, Yan D S. Incorporation of titanium into the inorganic wall of ordered porous zirconium oxide via direct synthesis. Chemistry of Materials, 2001, 13(3): 1035–1040
|
38 |
Ebina T, Iwasaki T, Chatterjee A, Katagiri M, Stucky G D. Comparative study of XPS and DFT with reference to the distributions of Al in tetrahedral octahedral sheets of phyllosilicates. The Journal of Physical Chemistry B, 1997, 101(7): 1125–1129
|
39 |
Jirka I. Initial and final state effects in the photoelectron and auger spectra of Si and Al bonded in zeolites. The Journal of Physical Chemistry B, 1997, 101(41): 8133–8140
|
40 |
Galindo I R, Viveros T, Chadwick D. Synthesis and characterization of titania-based ternary and binary mixed oxides prepared by the sol-gel method and their activity in 2-propanol dehydration. Industrial & Engineering Chemistry Research, 2007, 46(4): 1138–1147
|
41 |
Hiyoshi N. Nanocrystalline sodalite: preparation and application to epoxidation of 2-cyclohexen-1-one with hydrogen peroxide. Applied Catalysis A: General, 2012, 419–420: 164–169
|
42 |
Zhan H, Yang X, Wang C, Chen J, Wen Y, Liang C, Greer H F, Wu M, Zhou W. Multiple nucleation and crystal growth of barium titanate. Crystal Growth & Design, 2012, 12(3): 1247–1253
|
43 |
Sing K S W, Everett D H, Haul R A W, Moscou L, Pierotti R A, Rouquérol J, Siemieniewska T. Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity. Pure and Applied Chemistry, 1985, 57(4): 603–619
|
44 |
Zhang H, Wang Y M, Zhang L, Gerritsen G, Abbenhuis H C L, van Santen R A, Li C. Enantioselective epoxidation of β-methylstyrene catalyzed by immobilized Mn(salen) catalysts in different mesoporous silica supports. Journal of Catalysis, 2008, 256(2): 226–236
|
45 |
Lee K H, Kim K W, Pesapane A, Kim H Y, Rabolt J F. Polarized FT-IR study of macroscopically oriented electrospun Nylon-6 nanofibers. Macromolecules, 2008, 41(4): 1494–1498
|
46 |
Pan C, Huang B, Li X, Zhu H, Zhang D, Zheng A, Li Y, Sun Y. Synthesis and catalytic property of fibrous titanium-containing graphite oxide. Catalysis Surveys from Asia, 2017, 21(4): 160–174
|
47 |
Barroso-Bogeat A, Alexandre-Franco M, Fernández-González C, Macías-García A, Gómez-Serrano V. Preparation of activated carbon-SnO2, TiO2, and WO3 catalysts. Study by FT-IR spectroscopy. Industrial & Engineering Chemistry Research, 2016, 55(18): 5200–5206
|
48 |
Eryürek M, Haman Bayarı S, Yüksel D, Hanhan M E. Density functional investigation of the molecular structures, vibrational spectra and molecular properties of sulfonated pyridyl imine ligands and their palladium complexes. Computational and Theoretical Chemistry, 2013, 1013: 109–115
|
/
〈 | 〉 |