Skip to main content
Disciplines
Automotive Business IT + Informatics Construction + Real Estate Electrical Engineering + Electronics Energy + Sustainability Insurance + Risk Finance + Banking Management + Leadership Marketing + Sales Mechanical Engineering + Materials
Events
DE
EN
Books
Journals
Topic Page
Marketing
Start single access now
Access for companies
EXTENDED SEARCH
Log in
Top
Journal of Sol-Gel Science and Technology
Published in: Journal of Sol-Gel Science and Technology 3/2020

19-03-2020 | Review Paper: Sol-gel and hybrid materials for catalytic, photoelectrochemical and sensor applications

Sol–gel catalysts for synthetic organic chemistry: milestones in 30 years of successful innovation

Author: Mario Pagliaro

Published in: Journal of Sol-Gel Science and Technology | Issue 3/2020

Log in

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Abstract

First commercialized in the second half of the 1990s as organosilica-entrapped lipases, sol–gel catalysts share several unique properties that make them ideally suited for process chemistry, namely synthetic organic chemistry in the fine chemicals industry. Is their application potential fully realized? What are the obstacles to their widespread uptake in the specialty and fine chemicals industry? Can they also be employed in visible-light photocatalysis?
previous article Hierarchically porous monoliths prepared via sol–gel process accompanied by spinodal decomposition
next article Mechanisms for texture in BaTiO3 thin films from aqueous chemical solution deposition

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now
Literature
1.
Braun S, Shtelzer S, Rappoport S, Avnir D, Ottolenghi M (1992) Biocatalysis by sol-gel entrapped enzymes. J Non-Cryst Solids 147–148:739–743
2.
López T, Bosch P, Asomoza M, Gomez R (1992) Ru/SiO2-impregnated and sol-gel-prepared catalysts: synthesis, characterization, and catalytic properties. J Catal 133:247–259
3.
Avnir D (1995) Organic chemistry within ceramic matrixes: doped sol-gel materials. Acc Chem Res 28:328–334
4.
5.
Cauqui MA, Rodríguez-Izquierdo JM (1992) Application of the sol-gel methods to catalyst preparation. J Non-Cryst Solids 147/148:724–738
6.
Yanagisawa T, Shimizu T, Kuroda K, Kato C (1990) The preparation of alkyltrimethylammonium-kanemite complexes and their conversion to microporous materials. Bull Chem Soc Jpn 63:988–992
7.
8.
Reetz MT, Zonta A, Simpelkamp J (1995) Efficient heterogeneous biocatalysts by entrapment of lipases in hydrophobic sol–gel materials. Angew Chem Int Ed Engl 34:301–303
9.
Reetz MT, Zonta A, Simpelkamp J (1996) Efficient immobilization of lipases by entrapment in hydrophobic sol-gel materials. Biotechnol Bioeng 49:527–534
10.
Reetz MT, Tielmann P, Wiesenhöfer W, Könen W, Zonta A (2003) Second generation sol-gel encapsulated lipases: robust heterogeneous biocatalysts. Adv Synth Catal 345:717–728
11.
Ciriminna R, Demma Carà P, Sciortino M, Pagliaro M (2011) Catalysis with doped sol-gel silicates. Adv Synth Catal 353:677–687
12.
Avnir D, Blum J, Nairoukh Z (2015) Better catalysis with organically modified sol-gel materials. In: Levy D, Zayat M (eds) The sol-gel handbook, vol 2, Wiley-VCH, Weinheim, Germany, pp 963–985
13.
Esposito S (2019) “Traditional” sol-gel chemistry as a powerful tool for the preparation of supported metal and metal oxide catalysts. Materials 12:668
14.
Ozin G (1992) Nanochemistry: synthesis in diminishing dimensions. Adv Mater 4:612–649
15.
Pagliaro M (2015) Advancing nanochemistry education. Chem Eur J 21:11931–11936
16.
Pagliaro M (2019) Chemistry education fostering creativity in the digital era. Isr J Chem 59:565–571
17.
Hübner S, de Vries JG, Farina V (2016) Why does industry not use immobilized transition metal complexes as catalysts? Adv Synth Catal 358:3–25
18.
Cole-Hamilton DJ (2003) Homogeneous catalysis–new approaches to catalyst separation, recovery, and recycling. Science 299:1702–1706
19.
20.
Ciriminna R, Bolm C, Fey T, Pagliaro M (2002) Sol-gel ormosils doped with TEMPO as recyclable catalysts for the selective oxidation of alcohols. Adv Synth Catal 344:159–163
21.
Michaud A, Gingras G, Morin M, Béland F, Ciriminna R, Avnir D, Pagliaro M (2007) SiliaCat TEMPO: an effective and useful oxidizing catalyst. Org Process Res Dev 11:766–768
22.
Pandarus V, Ciriminna R, Gingras G, Béland F, Drobod M, Jima O, Pagliaro M (2013) Greening heterogeneous catalysis for fine chemicals. Tetrahedron Lett 54:1129–1132
23.
Pagliaro M, Bolm C, Ciriminna R (2002) Sol-gel ormosils doped with TEMPO as recyclable catalysts for the selective oxidation of alcohols. Adv Synth Catal 344:159–163
24.
Fidalgo A, Ciriminna R, Ilharco LM, Pagliaro M (2005) Role of the alkyl-alkoxide precursor on the structure and catalytic properties of hybrid sol-gel catalysts. Chem Mater 17:6686–6694
25.
26.
Jun SH, Park SG, Kang NG (2019) One-pot method of synthesizing TEMPO-oxidized bacterial cellulose nanofibers using immobilized TEMPO for skincare applications. Polymers 11:1044
27.
Saito T, Nishiyama Y, Putaux JL, Vignon M, Isogai A (2006) Homogeneous suspensions of individualized microfibrils from TEMPO-catalyzed oxidation of native cellulose. Biomacromolecul 7:1687–1691
28.
Pagliaro M (2018) Cellulose nanofiber: an advanced biomaterial soon to become ubiquitous. Chim Oggi 36(4):61–62
29.
Jetten J, Besemer A (2003) Process for the recovery of nitroxy compounds from organic solutions and oxidation process. US20050154206A1
30.
Patankar C, Renneckar S (2017) Greener synthesis of nanofibrillated cellulose using magnetically separable TEMPO nanocatalyst. Green Chem 19:4792–4797
31.
Isogai A, Saito T, Fukuzumi H (2011) TEMPO-oxidized cellulose nanofibers. Nanoscale 3:71–85
32.
Ferrer ML, del Monte F, Levy D (2002) A novel and simple alcohol-free sol−gel route for encapsulation of labile proteins. Chem Mater 14:3619–3621
33.
Pagliaro M, Pandarus V, Béland F, Ciriminna R, Palmisano G, Demma Carà P (2011) A new class of heterogeneous Pd catalysts for synthetic organic chemistry. Catal Sci Technol 1:736–739
34.
Pandarus V, Ciriminna R, Béland F, Pagliaro M (2011) A new class of heterogeneous Pt catalysts for the chemoselective hydrogenation of nitroarenes. Adv Synth Catal 353:1306–1316
35.
Ciriminna R, Ilharco LM, Pandarus V, Fidalgo A, Béland F, Pagliaro M (2014) Towards waste free organic synthesis via nanostructured hybrid silicas. Nanoscale 6:6293–6300
36.
Fidalgo A, Ciriminna R, Lopes L, Pandarus V, Béland F, Ilharco LM, Pagliaro M (2013) The sol-gel entrapment of noble metals in hybrid silicas: a molecular insight. Chem Centr J 7:161
37.
Ciriminna R, Pandarus V, Béland F, Pagliaro M (2016) Fine chemical synthesis under flow using the siliacat catalysts. Catal Sci Technol 6:4678–4685
38.
Ciriminna R, Pandarus V, Fidalgo A, Ilharco LM, Béland F, Pagliaro M (2015) SiliaCat: a versatile catalyst series for synthetic organic chemistry. Org Process Res Dev 19:755–768
39.
Ciriminna R, Della Pina C, Falletta E, Teles JH, Pagliaro M (2016) Industrial applications of gold catalysis. Angew Chem Int Ed 55:14210–14217
40.
Ramirez Côté C, Ciriminna R, Pandarus V, Béland F, Pagliaro M (2018) Comparing the pyrophoricity of palladium catalysts for heterogeneous hydrogenation. Org Process Res Dev 22:1852–1855
41.
Ciriminna R, Pandarus V, Béland F, Pagliaro M (2014) Catalytic hydrogenation of squalene to squalane. Org Process Res Dev 18:1110–1115
42.
Pandarus V, Ciriminna R, Kaliaguine S, Béland F, Pagliaro M (2015) Heterogeneously catalyzed hydrogenation of squalene to squalane under mild conditions. ChemCatChem 7:2071–2076
43.
Pandarus V, Ciriminna R, Kaliaguine S, Béland F, Pagliaro M (2017) Solvent-free chemoselective hydrogenation of squalene to squalane. ACS Omega 2:3989–3996
44.
Pagliaro M, Sciortino M, Ciriminna R, Alonzo G, De Schrijver A (2011) From molecules to systems: sol-gel microencapsulation in silica-based materials. Chem Rev 111:765–789
45.
Pandarus V, Ciriminna R, Gingras G, Béland F, Pagliaro M, Kaliaguine S (2019) Waste-free and efficient hydrosilylation of olefins. Green Chem 21:129–140
46.
Ghahremani M, Ciriminna R, Pandarus V, Scurria A, La Parola V, Giordano F, Avellone G, Béland F, Karimi B, Pagliaro M (2018) Green and direct synthesis of benzaldehyde and benzyl benzoate in one pot. ACS Sust Chem Eng 6:15441–15446
47.
Lemay M, Pandarus V, Simard M, Marion O, Tremblay L, Béland F (2010) SiliaCat S-Pd and SiliaCat DPP-Pd: highly reactive and reusable heterogeneous silica-based palladium catalysts. Top Catal 53:1059–1062
48.
de Juan M. Muñoz, Alcázar J, de la Hoz A, Díaz-Ortiz A(2012) Cross‐coupling in flow using supported catalysts: mild, clean, efficient and sustainable Suzuki–Miyaura coupling in a single pass Adv Synth Catal 354:3456–3460
49.
Egle B, de Muñoz JM, Alonso N, De Borggraeve WM, de la Hoz A, Díaz-Ortiz A, Alcázar J (2014) First example of alkyl–aryl Negishi cross-coupling in flow: mild, efficient and clean introduction of functionalized alkyl groups. J Flow Chem 4:22–25
50.
Greco R, Goessler W, Cantillo D, Kappe CO (2015) Benchmarking immobilized di- and triarylphosphine palladium catalysts for continuous-flow cross-coupling reactions: efficiency, durability, and metal leaching studies. ACS Catal 5:1303–1312
51.
McAfee SM, Welch GC (2019) Development of organic dye‐based molecular materials for use in fullerene‐free organic solar cells. Chem Rec 19:989–1007
52.
53.
Pandarus V, Desplantier-Giscard D, Gingras G, Ciriminna R, Béland F, Pagliaro M (2013) Greening the valsartan synthesis: scale-up of key Suzuki-Miyaura coupling over SiliaCat DPP-Pd. Org Process Res Dev 17:1492–1497
54.
Martin AD, Siamaki AR, Belecki K, Gupton F (2015) A flow-based synthesis of telmisartan. J Flow Chem 5:145–147
55.
Ciriminna R, Hesemann P, Moreau J, Carraro M, Campestrini S, Pagliaro M (2006) Aerobic oxidation of alcohols in carbon dioxide with silica-supported ionic liquids doped with perruthenate. Chem Eur J 12:5220–5224
56.
Ciriminna R, Campestrini S, Pagliaro M (2006) FluoRuGel: a versatile catalyst for aerobic alcohol oxidation in dense phase carbon dioxide. Org Biomol Chem 4:2637–2641
57.
58.
Ciriminna R, Pagliaro M (2013) Green chemistry in the fine chemicals and pharmaceutical industries. Org Process Res Dev 17:1479–1484
59.
Pagliaro M (2019) An industry in transition: the chemical industry and the megatrends driving its forthcoming transformation. Angew Chem Int Ed 58:11154–11159
60.
61.
Bryan MC, Dunn PJ, Entwistle D, Gallou F, Koenig SG, Hayler JD, Hickey MR, Hughes S, Kopach ME, Moine G, Richardson PI, Roschangar F, Steven A, Weiberth FJ (2018) Key green chemistry research areas from a pharmaceutical manufacturers’ perspective revisited. Green Chem 20:5082–5103
62.
Jensen KF (2017) Flow chemistry-microreaction technology comes of age. AIChE J 63:858–869
63.
Porcu L (2019) A flow chemistry approach for the supply risk management: optimization of industrial processes. Making Pharmaceuticals, Milano
64.
Zhang Y, Ciriminna R, Palmisano G, Xu YJ, Pagliaro M (2014) Sol-gel entrapped visible light photocatalysts for selective conversions. RSC Adv 4:18341–18346
65.
Ciriminna R, Delisi R, Parrino F, Palmisano L, Pagliaro M (2017) Tuning the photocatalytic activity of bismuth wolframate: towards selective oxidations for the biorefinery driven by solar-light. Chem Commun 53:7521–7524
66.
Ciriminna R, Delisi R, Xu YJ, Pagliaro M (2016) Towards the waste-free synthesis of fine chemicals with visible light. Org Process Res Dev 20:403–408
67.
Smith JD, Jamhawi AM, Jasinski JB, Gallou F, Ge J, Advincula R, Liu J, Handa S (2019) Organopolymer with dual chromophores and fast charge-transfer properties for sustainable photocatalysis. Nat Commun 10:1837
68.
Karimi B, Ghahremani M, Ciriminna R, Pagliaro M (2018) New stable catalytic electrodes functionalized with TEMPO for the waste-free oxidation of alcohols. Org Process Res Dev 22:1298–1305
Metadata
Title
Sol–gel catalysts for synthetic organic chemistry: milestones in 30 years of successful innovation
Author
Mario Pagliaro
Publication date
19-03-2020
Publisher
Springer US
Published in
Journal of Sol-Gel Science and Technology / Issue 3/2020
Print ISSN: 0928-0707
Electronic ISSN: 1573-4846
DOI
https://doi.org/10.1007/s10971-020-05266-3

Other articles of this Issue 3/2020

Journal of Sol-Gel Science and Technology 3/2020 Go to the issue

Original Paper: Sol-gel and hybrid materials for biological and health (medical) applications

Synthesis of (Mn(1−x)Znx)Fe2O4 nanoparticles for magnetocaloric applications

Editorial

Donald R. Ulrich Award 2019

Editorial

Preface

Review Paper: Sol–gel and hybrid materials for biological and health (medical) applications

Antifouling and antimicrobial coatings based on sol–gel films

Original Paper: Nano- and macroporous materials (aerogels, xerogels, cryogels, etc.)

Silica-based microspheres with interconnected macroporosity by phase separation

Original Paper: Sol-gel and hybrid materials for biological and health (medical) applications

Magnetic polyelectrolyte-based composites with dual anticoagulant and thrombolytic properties: towards optimal composition

Premium Partners

    Image Credits