HETEROGENEOUS CATALYSIS IN SUSTAINABLE GREEN SOLVENT: ALKENES HYDROGENATION WITH NEW SILICA IMMOBILIZED PALLADIUM COMPLEX CONTAINING S,O-CHELATING LIGAND

Filiz Yılmaz

doi:10.18038/aubtda.409518

EN

HETEROGENEOUS CATALYSIS IN SUSTAINABLE GREEN SOLVENT: ALKENES HYDROGENATION WITH NEW SILICA IMMOBILIZED PALLADIUM COMPLEX CONTAINING S,O-CHELATING LIGAND

Abstract

Pd(II) complex containing S,O-chelating ligand was immobilized on surface of the amine functionalized silica support in scCO₂ media. Silica-based catalyst (SiO₂-ThiophPd(II)) were characterized by IR, SEM, XRF, and BET analyses. The catalytic activity of the immobilized catalyst in hydrogenation reactions of alkenes has been compared with the homogeneous counterpart. SiO₂-ThiophPd(II) catalyst showed good activity and reusability than homogeneous system. The best conversion in styrene hydrogenation was obtained with TOF value as 5871 h^-1 at 370 K, 10 bar H₂ and 1500 psi total pressure. Especially, while homogeneous counterpart has not activity in cyclohexene hydrogenation, it has been provided 100% cyclohexane conversion with the immobilized catalyst. It has also been found that the catalyst can be reused at least ten times without significant loss of activity in the styrene hydrogenation

Keywords

Immobilized Pd(II) complex,Alkene Hydrogenation,Reusability

References

[1] Mehendale NC, Bezemer C, Walree CA Van, et al. Novel silica immobilized NCN-pincer palladium ( II ) and platinum ( II ) complexes : Application as Lewis acid catalysts. 2006; 257:167–175.
[2] Jessop PG, Heldebrant DJ. Green Biphasic Homogeneous Catalysis. ChemInform 2006; 37(35):627–648.
[3] Mäki-Arvela P, Hájek J, Salmi T, et al. Chemoselective hydrogenation of carbonyl compounds over heterogeneous catalysts. Appl Catal A Gen 2005; 292:1–49.
[4] Cornils B, Herrmann WA. Concepts in homogeneous catalysis : the industrial view. 2003; 216:23–31.
[5] Corma A, Garcia H. Silica-bound homogenous catalysts as recoverable and reusable catalysts in organic synthesis. Adv Synth Catal 2006; 348:1391–1412.
[6] Wang Z, Ding K, Uozumi Y. An Overview of Heterogeneous Asymmetric Catalysis. In: Handbook of Asymmetric Heterogeneous Catalysis. 2008; pp. 1–24.
[7] Merckle C, Blümel J. Improved Rhodium Hydrogenation Catalysts Immobilized on Oxidic Supports. Adv Synth Catal 2003; 34:5–15.
[8] Margelefsky EL, Zeidan RK, Davis ME. Cooperative catalysis by silica-supported organic functional groups. Chem Soc Rev 2008; 37:1118–1126.
[9] Jannes G. Supported homogeneous catalysts. Appl Catal 1985; 14(2):394.
[10] Thomas JM, Raja R. Catalytic significance of organometallic compounds immobilized on mesoporous silica: Economically and environmentally important examples. J Organomet Chem 2004; 689:4110–4124.

[11] Dioos BML, Vankelecom IFJ, Jacobs PA. Aspects of immobilisation of catalysts on polymeric supports. Adv Synth Catal 2006; 348:1413–1446.
[12] Hauthal WH. Advances with supercritical fluids [ review ]. Chemos 2001; 43:123–35.
[13] Sheldon RA. Green solvents for sustainable organic synthesis: state of the art. Green Chem 2005; 7:267–278.
[14] Mizuuchi H, Jaitely V, Murdan S, et al. Room temperature ionic liquids and their mixtures: Potential pharmaceutical solvents. Eur J Pharm Sci 2008; 33:326–31.
[15] Pozzi G, Cavazzini M, Cinato F, et al. Enantioselective catalysis in fluorinated media - Synthesis and properties of chiral perfluoroalkylated (salen)manganese complexes. European J Org Chem 1999; (8):1947–1955.
[16] Kankala RK, Zhang YS, Wang S, et al. Supercritical Fluid Technology : An Emphasis on Drug Delivery and Related Biomedical Applications. Adv Heal Mater 2017; 6:2–31.
[17] Budisa N, Schulze-makuch D. Supercritical Carbon Dioxide and Its Potential as a Life-Sustaining Solvent in a Planetary Environment. Life 2014; 4:331–340.
[18] Leitner W. Supercritical carbon dioxide as a green reaction medium for catalysis. Acc Chem Res 2002; 35(9):746–756.
[19] Rajagopalan B, Wei M, Musie GT, et al. Homogeneous catalytic epoxidation of organic substrates in CO2-expanded solvents in the presence of water-soluble oxidants and catalysts. Ind Eng Chem Res 2003; 42(25):6505–6510.
[20] Wang X, Kawanami H, Dapurkar SE, et al. Selective oxidation of alcohols to aldehydes and ketones over TiO2-supported gold nanoparticles in supercritical carbon dioxide with molecular oxygen. Appl Catal A Gen 2008; 349:86–90.
[21] Wu W, Li W, Han B, et al. Effect of organic cosolvents on the solubility of ionic liquids in supercritical CO2. J Chem Eng Data 2004; 49:1597–1601.
[22] Zhang X, Heinonen S, Levanen E. Applications of supercritical carbon dioxide in materials processing and synthesis. RSC Adv 2014; 4:61137–61152.
[23] Cooper BAI. Porous Materials and Supercritical Fluids. Adv Mater 2003; 15(13):1049–1059.
[24] Yilmaz F, Mutlu A, Unver H, et al. Hydrogenation of olefins catalyzed by Pd(II) complexes containing a perfluoroalkylated S,O-chelating ligand in supercritical CO2 and organic solvents. J Supercrit Fluids 2010; 54(2):202–209.
[25] Sharma RK, Mishra M, Sharma S, et al. Zinc ( II ) complex immobilized on amine functionalized silica gel : a novel , highly efficient and recyclable catalyst for multicomponent click synthesis of 1,4-disubstituted 1,2,3-triazoles. J Coord Chem Taylor & Francis 2016; 69:1152–1165.
[26] F Yilmaz, Y Karaağaç İK. Heterogenization of Homogeneous Perfluorothiophene Rh(I) Complex And Examination of Hydrogenation Activity in scCO2 Media. Anadolu Univ J Sci Technol A - Appl Sci Eng 2017.

Details

Primary Language

English

Subjects

Engineering

Journal Section

Research Article

Authors

Filiz Yılmaz ^*
0000-0002-6138-0460
Türkiye

Publication Date

June 30, 2018

Submission Date

March 26, 2018

Acceptance Date

June 4, 2018

Published in Issue

Year 2018 Volume: 19 Number: 2

DOI

https://doi.org/10.18038/aubtda.409518

IZ

https://izlik.org/JA28YE99GM

APA

Yılmaz, F. (2018). HETEROGENEOUS CATALYSIS IN SUSTAINABLE GREEN SOLVENT: ALKENES HYDROGENATION WITH NEW SILICA IMMOBILIZED PALLADIUM COMPLEX CONTAINING S,O-CHELATING LIGAND. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, 19(2), 546-554. https://doi.org/10.18038/aubtda.409518

AMA

1.Yılmaz F. HETEROGENEOUS CATALYSIS IN SUSTAINABLE GREEN SOLVENT: ALKENES HYDROGENATION WITH NEW SILICA IMMOBILIZED PALLADIUM COMPLEX CONTAINING S,O-CHELATING LIGAND. AUJST-A. 2018;19(2):546-554. doi:10.18038/aubtda.409518

Chicago

Yılmaz, Filiz. 2018. “HETEROGENEOUS CATALYSIS IN SUSTAINABLE GREEN SOLVENT: ALKENES HYDROGENATION WITH NEW SILICA IMMOBILIZED PALLADIUM COMPLEX CONTAINING S,O-CHELATING LIGAND”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 19 (2): 546-54. https://doi.org/10.18038/aubtda.409518.

EndNote

Yılmaz F (June 1, 2018) HETEROGENEOUS CATALYSIS IN SUSTAINABLE GREEN SOLVENT: ALKENES HYDROGENATION WITH NEW SILICA IMMOBILIZED PALLADIUM COMPLEX CONTAINING S,O-CHELATING LIGAND. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 19 2 546–554.

IEEE

[1]F. Yılmaz, “HETEROGENEOUS CATALYSIS IN SUSTAINABLE GREEN SOLVENT: ALKENES HYDROGENATION WITH NEW SILICA IMMOBILIZED PALLADIUM COMPLEX CONTAINING S,O-CHELATING LIGAND”, AUJST-A, vol. 19, no. 2, pp. 546–554, June 2018, doi: 10.18038/aubtda.409518.

ISNAD

Yılmaz, Filiz. “HETEROGENEOUS CATALYSIS IN SUSTAINABLE GREEN SOLVENT: ALKENES HYDROGENATION WITH NEW SILICA IMMOBILIZED PALLADIUM COMPLEX CONTAINING S,O-CHELATING LIGAND”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 19/2 (June 1, 2018): 546-554. https://doi.org/10.18038/aubtda.409518.

JAMA

1.Yılmaz F. HETEROGENEOUS CATALYSIS IN SUSTAINABLE GREEN SOLVENT: ALKENES HYDROGENATION WITH NEW SILICA IMMOBILIZED PALLADIUM COMPLEX CONTAINING S,O-CHELATING LIGAND. AUJST-A. 2018;19:546–554.

MLA

Yılmaz, Filiz. “HETEROGENEOUS CATALYSIS IN SUSTAINABLE GREEN SOLVENT: ALKENES HYDROGENATION WITH NEW SILICA IMMOBILIZED PALLADIUM COMPLEX CONTAINING S,O-CHELATING LIGAND”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, vol. 19, no. 2, June 2018, pp. 546-54, doi:10.18038/aubtda.409518.

Vancouver

1.Filiz Yılmaz. HETEROGENEOUS CATALYSIS IN SUSTAINABLE GREEN SOLVENT: ALKENES HYDROGENATION WITH NEW SILICA IMMOBILIZED PALLADIUM COMPLEX CONTAINING S,O-CHELATING LIGAND. AUJST-A. 2018 Jun. 1;19(2):546-54. doi:10.18038/aubtda.409518

Cited By

The green chemistry paradigm in modern organic synthesis

Russian Chemical Reviews

https://doi.org/10.59761/RCR5104