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Pd supported on N-doped-ordered mesoporous carbons’ catalysts for selective hydrodechlorination of 4-chlorophenol

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Abstract

Pd catalysts supported on N-doped-ordered mesoporous carbons (NOMC) have been prepared and tested for selective hydrogenation of 4-chlorophenol (4-CP) with H2. The difference from the previous methods is that the NOMC was synthesized using urea as nitrogen source via one-pot route. The rate constant of Pd/NOMC for hydrodechlorination of 4-CP was about 135.9 h−1 which were higher than Pd/OMC (65.6 h−1) and Pd/AC (20.8 h−1). It could be attributed to the synergetic effects of mesoporous structure, N-doped supports, and the stabilized small PdNPs. The conversion changed from 100 to 90.2% after the sixth reaction using Pd/NOMC which could be caused by the palladium leaching.

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Abbreviations

NOMC:

N-doped-ordered mesoporous carbons

4-CP:

4-Chlorophenol

HDC:

Catalytic hydrodechlorination

SAXRD:

Small-angle X-ray diffraction

TEM:

Transmission electron microscopy

HMT:

Hexamethylenetetramine

TMB:

1,3,5-Trimethylbenzene

PdNPs:

Pd nanoparticles

References

  • Albers P, Pietsch J, Parker S (2001) Poisoning and deactivation of palladium catalysts. J Mol Catal A Chem 173:275–286

    Article  CAS  Google Scholar 

  • Aramendıa M, Borau V, Garcıa I, Jimenez C, Lafont F, Marinas A, Marinas J, Urbano F (1999) Influence of the reaction conditions and catalytic properties on the liquid-phase hydrodechlorination of chlorobenzene over palladium-supported catalysts: activity and deactivation. J Catal 187:392–399

    Article  Google Scholar 

  • Baeza J, Calvo L, Rodriguez J, Gilarranz M (2016) Catalysts based on large size-controlled Pd nanoparticles for aqueous-phase hydrodechlorination. Chem Eng J 294:40–48

    Article  CAS  Google Scholar 

  • Benitez J, Gloria D (2000) Effect of chlorine released during hydrodechlorination of chlorobenzene over Pd, Pt and Rh supported catalysts. React Kinet Catal Lett 70:67–72

    Article  CAS  Google Scholar 

  • Bernard C, Marie C, Francois F, Didier T (1993) Conversion under hydrogen of dichlorodifluoromethane over supported palladium catalysts. J Catal 141:21–33

    Article  Google Scholar 

  • Böhringer B, Guerra Gonzalez O, Eckle I, Müller M, Giebelhausen J, Schrage C, Fichtner S (2011) Polymer-based spherical activated carbons-from adsorptive properties to filter performance. Chem Ing Tech 83:53–60

    Article  CAS  Google Scholar 

  • Bovkun TT, Sasson Y, Blum J (2005) Conversion of chlorophenols into cyclohexane by a recyclable Pd-Rh catalyst. J Mol Catal A Chem 242:68–73

    Article  CAS  Google Scholar 

  • Calvol L, Gilarranz M, Casas J, Mohedano A, Rodriquez J (2009) Hydrodechlorination of 4-chlorophenol in water with formic acid using a Pd/activated carbon catalyst. J Hazard Mater 161:842–847

    Article  CAS  Google Scholar 

  • Chang W, Kim H, Lee G, Byoung J (2016) Catalytic hydrodechlorination reaction of chlorophenols by Pd nanoparticles supported on graphene research on chemical intermediates. Res Chem Intermed 42:71–82

    Article  CAS  Google Scholar 

  • Datta K, Reddy K, Ariga K, Vinu A (2010) Gold nanoparticles embedded in a mesoporous carbon nitride stabilizer for highly efficient three-component coupling reaction. Angew Chem 49:5961–5965

    Article  CAS  Google Scholar 

  • Deng H, Fan G, Wang C, Zhang L (2014) Aqueous phase catalytic hydrodechlorination of 4-chlorophenol over palladium deposited on reduced graphene oxide. Catal Commun 46:219–223

    Article  CAS  Google Scholar 

  • Diaz E, Ordóñez S, Bueres R, Asedegbega-Nieto E, Sastre H (2010) High-surface area graphites as supports for hydrodechlorination catalysts: tuning support surface chemistry for an optimal performance. Appl Catal B Environ 99:181–190

    Article  CAS  Google Scholar 

  • Diaz E, Mohedano A, Casas J, Calvo J, Gilarranz M, Rodriguez J (2011) Comparison of activated carbon-supported Pd and Rh catalysts for aqueous-phase hydrodechlorination. Appl Catal B Environ 106:469–475

    Article  CAS  Google Scholar 

  • Diaz E, Mohedano A, Casas J, Rodriguez J (2016) Analysis of the deactivation of Pd, Pt and Rh on activated carbon catalysts in the hydrodechlorination of the MCPA herbicide. Appl Catal B Environ 181:429–435

    Article  CAS  Google Scholar 

  • Gómez-Quero S, Díaz E, Cárdenas-Lizana F, Keane M (2010a) Solvent effects in the catalytic hydrotreament of haloaromatics over Pd/Al2O3 in water + organic mixtures. Chem Eng Sci 65:3786–3797

    Article  CAS  Google Scholar 

  • Gómez-Quero SF, Cárdenas-Lizana F, Keane MA (2010b) Solvent effects in the hydrodechlorination of 2,4-dichlorophenol over Pd/Al2O3. AlChE J 56:756–767

    Google Scholar 

  • Gómez-Quero S, Cárdenas-Lizana F, Keane M (2011) Liquid phase catalytic hydrodechlorination of 2,4-dichlorophenol over Pd/Al2O3: batch vs. continuous operation. Chem Eng J 166:1044–1051

    Article  CAS  Google Scholar 

  • Gómez-Sainero LM, Seoane XL, Fierro JLG, Arcoya A (2002) Liquid-phase hydrodechlorination of CCl4 to CHCl3 on Pd/carbon catalysts: nature and role of pd active species. J Catal 209:279–288

    Article  CAS  Google Scholar 

  • Gong Y, Zhang P, Xu X, Li Y, Li H, Wang Y (2013) A novel catalyst Pd@ompg-C3N4 for highly chemoselective hydrogenation of quinoline under mild conditions. J Catal 297:272–280

    Article  CAS  Google Scholar 

  • Hashimoto Y, Ayame A (2003) Low-temperature hydrodechlorination of chlorobenzenes on platinum-supported alumina catalysts. Appl Catal A Gen 250:247–254

    Article  CAS  Google Scholar 

  • Hildebrand H, Mackenzie K, Kopinke F-D (2009) Highly active Pd-on-magnetite nanocatalysts for aqueous phase hydrodechlorination reactions. Energy Environ Sci 43:3254–3259

    CAS  Google Scholar 

  • Huang Y, Cai H, Feng D, Gu D, DengY TuB, Wang H, Webley P, Zhao D (2008) One-step hydrothermal synthesis of ordered mesostructured carbonaceous monoliths with hierarchical porosities. Chem Commun 23:2641–2643

    Article  CAS  Google Scholar 

  • Jadbabaei N, Ye T, Shuai D, Zhang H (2017) Development of palladium-resin composites for catalytic hydrodechlorination of 4-chlorophenol. Appl Catal B Environ 205:576–586

    Article  CAS  Google Scholar 

  • Li X, Wang H, Robinson J, Sanchez H, Diankov G, Dai H (2009) Simultaneous nitrogen doping and reduction of graphene oxide. Am Chem Soc 131:15939–15944

    Article  CAS  Google Scholar 

  • Li X, Wang X, Markus A (2012) Mesoporous g-C3N4 nanorods as multifunctional supports of ultrafine metal nanoparticles: hydrogen generation from water and reduction of nitrophenol with tandem catalysis in one step. Chem Sci 3:2170–2174

    Article  CAS  Google Scholar 

  • Li Y, Xu X, Zhang P, Wang Y (2013) Highly selective Pd@mpg-C3N4 catalyst for phenol hydrogenation in aqueous phase. RSC Adv 27:10973–10982

    Article  CAS  Google Scholar 

  • Li R, Zhao J, Han D, Li X (2017) One-step synthesis of B-doped mesoporous carbon as supports of Pd nanoparticles for liquid phase catalytic hydrodechlorination. Catal Commun 97:116–119

    Article  CAS  Google Scholar 

  • Liu L, Wang F, Shao G, Yuan Z (2010) A low-temperature autoclaving route to synthesize monolithic carbon materials with an ordered mesostructure. Carbon 48:2089–2099

    Article  CAS  Google Scholar 

  • Liu D, Lei J, Guo L, Deng K (2011) Simple hydrothermal synthesis of ordered mesoporous carbons from resorcinol and hexamine. Carbon 49:2113–2119

    Article  CAS  Google Scholar 

  • Liu D, Lei J, Guo L, Qu D, Li Y, Su B (2012) One-pot aqueous route to synthesize highly ordered cubic and hexagonal mesoporous carbons from resorcinol and hexamine. Carbon 50:476–487

    Article  CAS  Google Scholar 

  • Lyonnard S, Bartlett J, Sizgek E, Finnie K, Zemb T, Woolfrey J (2002) Role of interparticle potential in controlling the morphology of spray-dried powders from aqueous nanoparticle sols. Langmuir 18:10386–10397

    Article  CAS  Google Scholar 

  • Mitoma Y, Kakeda M, Simion A, Egashira N, Simion C (2009) Metallic Ca-Rh/C-methanol, a high-performing system for the hydrodechlorination/ring reduction of mono- and poly chlorinated aromatic substrates. Energy Environ Sci 43:5952–5958

    CAS  Google Scholar 

  • Molina C, Pizarro A, Gilarranz M, Casas J, Rodriguez J (2010) Hydrodechlorination of 4-chlorophenol in water using Rh-Al pillared clays. Chem Eng J 160:578–585

    Article  CAS  Google Scholar 

  • Molina CB, Pizarro AH, Casas JA, Rodriguez JJ (2014) Aqueous-phase hydrodechlorination of chlorophenols with pillared clays-supported Pt, Pd and Rh catalysts. Appl Catal B Environ 148:330–338

    Article  CAS  Google Scholar 

  • Molina CB, Calvo L, Gilarranz MA, Casas JA, Rodriguez JJJ (2009) Pd–Al pillared clays as catalysts for the hydrodechlorination of 4-chlorophenol in aqueous phase. J Hazard Mater 172:214–223

    Article  CAS  PubMed  Google Scholar 

  • Moon D, Jo Chung M, You Park K, In Hong S (1998) Deactivation of Pd catalysts in the hydrodechlorination of chloropentafluoroethane. Appl Catal A Gen 168:159–170

    Article  CAS  Google Scholar 

  • Munoz M, de Pedro ZM, Casas JA, Rodriguez JJ (2014) Combining efficiently catalytic hydrodechlorination and wet peroxide oxidation (HDC–CWPO) for the abatement of organochlorinated water pollutants. Appl Catal A 488:78–85

    Article  CAS  Google Scholar 

  • Öcal M, Maciejewski M, Baiker A (1999) Conversion of CCl2F2(CFC-12) in the presence and absence of H2 on sol-gel derived Pd/Al2O3 catalysts. Appl Catal B Environ 21:279–289

    Article  Google Scholar 

  • Osegueda O, Dafinov A, Llorca J, Medina F, Sueiras J (2015) Heterogeneous catalytic oxidation of phenol by in situ generated hydrogen peroxide applying novel catalytic membrane reactors. Chem Eng J 262:344–355

    Article  CAS  Google Scholar 

  • Romero-Anaya AJ, Ouzzine M, Lillo-Ródenas MA, Linares-Solano A (2014) Carbon 68:296–307

    Article  CAS  Google Scholar 

  • Rong H, Cai S, Niu Z, Li Y (2013) Composition-dependent catalytic activity of bimetallic nanocrystals: AgPd-catalyzed hydrodechlorination of 4-chlorophenol. ACS Catal 3:1560–1563

    Article  CAS  Google Scholar 

  • Santiago G, Fernando C, Mark K (2008) Effect of metal dispersion on the liquid-phase hydrodechlorination of 2,4-dichlorophenol over Pd/Al2O3. Ind Eng Chem Res 47:6841–6853

    Article  CAS  Google Scholar 

  • Shao Y, Xu Z, Wan H, Chen H, Liu F, Li L, Zheng S (2010) Influence of ZrO2 properties on catalytic hydrodechlorination of chlorobenzene over Pd/ZrO2 catalysts. J Hazard Mater 179:135–140

    Article  CAS  PubMed  Google Scholar 

  • Shao Y, Xu Z, Wan H, Wan Y, Chen H, Zheng S, Zhu D (2011) Enhanced liquid phase catalytic hydrodechlorination of 2,4-dichlorophenol over mesoporous carbon supported Pd catalysts. Catal Commun 12:1405–1409

    Article  CAS  Google Scholar 

  • Sohn H, Celik G, Gunduz S, Majumdar SS, Dean SL, Edmiston PL, Ozkan US (2017) Effect of high-temperature on the swellable organically-modified silica (SOMS) and its application to gas-phase hydrodechlorination of trichloroethylene. Appl Catal B Environ 209:80–90

    Article  CAS  Google Scholar 

  • Vinu A, Ariga K, Mori T, Nakanishi T, Hishita S, Golberg D, Bando Y (2005) Preparation and characterization of well-ordered hexagonal mesoporous carbon nitride & dagger. Adv Mater 17:1648–1652

    Article  CAS  Google Scholar 

  • Wang Y, Yao J, Li H, Su D, Markus A (2011) Highly selective hydrogenation of Phenol and derivatives over a Pd@Carbon nitride catalyst in aqueous media. J Am Chem Soc 133:2362–2365

    Article  CAS  PubMed  Google Scholar 

  • Wang J, Liu H, Gu X, Wang H, Su D (2014) Synthesis of nitrogen-containing ordered mesoporous carbon as a metal-free catalyst for selective oxidation of ethylbenzene. Chem Commun 50:9182–9184

    Article  CAS  Google Scholar 

  • Wiersma A, Van de Sandt E, Makkee M, Luteijn C, Van Bekkum H, Moulijn JA (1996) Process for the selective hydrogenolysis of CCl2F2(CFC-12) into CH2F2(HFC-32). Catal Today 27:257–264

    Article  CAS  Google Scholar 

  • Wiersma A, van de Sandt E, Makkee M, Moulijn JA (2001) Deactivation of palladium on activated carbon in the selective hydrogenolysis of CCl2F2(CFC-12) into CH2F2(HFC-32). Appl Catal A Gen 212:223–238

    Article  CAS  Google Scholar 

  • Xia C, Xu J, Wu W, Liang X (2004) Pd/C-catalyzed hydrodehalogenation of aromatic halides in aqueous solutions at room temperature under normal pressure. Catal Commun 5:383–386

    Article  CAS  Google Scholar 

  • Xia C, Liu Y, Zhou S, Yang C, Liu S, Xu J, Yu J, Chen J, Liang X (2009) The Pd-catalyzed hydrodechlorination of chlorophenols in aqueous solutions under mild conditions: a promising approach to practical use in wastewater. J Hazard Mater 169:1029–1033

    Article  CAS  PubMed  Google Scholar 

  • Xu X, Li Y, Gong Y, Zhang P, Li H, Wang Y (2012) Synthesis of palladium nanoparticles supported on mesoporous N-doped carbon and their catalytic ability for biofuel upgrade. J Am Chem Soc 134:16987–16990

    Article  CAS  PubMed  Google Scholar 

  • Xue C, Tu B, Zhao D (2008) Evaporation-induced coating and self-assembly of ordered mesoporous carbon–silica composite monoliths with macroporous architecture on polyurethane foams. Adv Funct Mater 18:3914–3921

    Article  Google Scholar 

  • Yoneda T, Takido T, Konuma K (2007) Hydrodechlorination reactivity of para-substituted chlorobenzenes over platinum/carbon catalyst. J Mol Catal A Chem 265:80–89

    Article  CAS  Google Scholar 

  • Yuan G, Keane M (2004a) Liquid phase hydrodechlorination of chlorophenols over Pd/C and Pd/Al2O3: a consideration of HCl/catalyst interactions and solution pH effects. Appl Catal B Environ 52:301–314

    Article  CAS  Google Scholar 

  • Yuan G, Keane M (2004b) Role of base addition in the liquid-phase hydrodechlorination of 2,4-dichlorophenol over Pd/Al2O3 and Pd/C. J Catal 225:510–522

    Article  CAS  Google Scholar 

  • Yuan G, Keane M (2007) Aqueous-phase hydrodechlorination of 2,4-dichlorophenol over Pd/Al2O3: reaction under controlled pH. Ind Eng Chem Res 46:705–715

    Article  CAS  Google Scholar 

  • Zhang F, Meng Y, Gu D, Chen Y, Tu B, Zhao D (2006) An aqueous cooperative assembly route to synthesize ordered mesoporous carbons with controlled structures and morphology. Chemistry 18:5279–5288

    CAS  Google Scholar 

  • Zhang F, Jin J, Zhong X, Li S, Niu J, Li R, Ma J (2011) Pd immobilized on amine-functionalized magnetite nanoparticles: a novel and highly active catalyst for hydrogenation and Heck reactions. Green Chem 13:1238–1243

    Article  CAS  Google Scholar 

  • Zhang P, Gong Y, Li H, Chen Z, Wang Y (2013) Solvent-free aerobic oxidation of hydrocarbons and alcohols with Pd@N-doped carbon from glucose. Nat Commun 4:1593

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

The project was supported by the National Natural Science Foundation, China (21506138), and the Natural Science Foundation of Zhejiang Province, China (LQ15B060001).

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Authors and Affiliations

  1. School of Pharmaceutical and Chemical Engineering, TaiZhou University, Taizhou, 318000, Zhejiang, People’s Republic of China

    Rongrong Li, Shiting Wang, Yuan Hu, Hong Chen, Jingjing Chen, Chu Chu & Jianli Zheng

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  1. Rongrong Li
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  2. Shiting Wang
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  3. Yuan Hu
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  4. Hong Chen
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  5. Jingjing Chen
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Correspondence to Rongrong Li.

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Li, R., Wang, S., Hu, Y. et al. Pd supported on N-doped-ordered mesoporous carbons’ catalysts for selective hydrodechlorination of 4-chlorophenol. Chem. Pap. 72, 2425–2432 (2018). https://doi.org/10.1007/s11696-018-0477-8

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