A new class of heterogeneous Pd catalysts for synthetic organic chemistry

Pagliaro, Mario; Pandarus, Valerica; Béland, François; Ciriminna, Rosaria; Palmisano, Giovanni; Carà, Piera Demma

doi:10.1039/c1cy00119a

Cited by 71 publications

(65 citation statements)

References 16 publications

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“…[16] Recently,a ni mpressive advancementw as made by Pagliaroa nd co-workers, [17] who used SiliaCatPd 0 ,a no rganosilica catalyst. [18] Ther eaction proceeded at ambient temperature under atmospheric pressure in ethanol with aP dl oading of 0.2 mmol per gram of squalene.T he hydrogenation was performed under milder conditions and required low H 2 pressure and temperature. However, the reactionw as nonselective in the absence of as olvent and the catalyst wasn ot prepared in ac ost-effective manner.…”

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confidence: 99%

Palladium‐Nanoparticles‐Intercalated Montmorillonite Clay: A Green Catalyst for the Solvent‐Free Chemoselective Hydrogenation of Squalene

Soni

Sharma

2016

ChemCatChem

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Squalanei sa ni mportant ingredient in the cosmetic, nutraceutical, andp harmaceutical industries. It has also been used as am odel compound for the hydrocracking of crude and microalgae oil. Thus, as eries of green heterogeneousm etal catalysts were prepared to achievec omplete hydrogenation of highly unsaturated squalene into squalane. Surfacem odification of the clay and metal intercalation simultaneously occurred during wet impregnation. The Pd-nanoparticles-intercalated clay with ad ominating Pd(111)f acet showed the highest reactivity and selectivity.T he catalystw as stable with very low Pd leaching( % 0.03 ppm) and was recyclable withoutl osing any significant catalytic activity.The cost effectiveness ande asy availability of clays and claybased materials make them good choices as catalysts for the development of green methodsf or various chemical transformations.[1] Clay-based metal catalysts are preferred over metal catalysts owing to the advantagesa ssociated with the clays. [1b] Easy replacement of the interlamellarc ations in clays provides furtherp ossibilities to incorporate other cations or small molecules. Thus,s everal properties such as acidity,p ore size, and surfacea rea can be modified to influence catalytic performance. Naturally occurring clays can be modified either by physicalo rc hemical modification.[2] The treatment of natural montmorillonite clay with mineral acid is important for its improvedadsorption and catalytic properties. [3] The hydrogenation of unsaturated CÀCb onds by using heterogeneous catalysts [4] is an important industrial process.[5]Amongt hese processes, the chemoselective hydrogenation of highly unsaturated all-trans linear squalene into squalane is highly desirable. [6] Squalane is an exceptionale mollient with the distinct ability to penetrate human skin without feeling greasy and without harmful effects. [7] It is widely used in the cosmetic,n utraceutical, and pharmaceutical industries.[8] Recently,s qualane has drawn significant attentiona sahydrocracking model for crude and microalgae oil. [9] The hydrogenationo fs qualene was reported by Tsujimoto [10] in 1916 by using al arge amount of ap latinum catalyst in diethyl ether under H 2 pressure and was later reportedb yC hapman [11] in 1917 without any solvent at 190 8Ca nd under atmospheric H 2 pressure. An unsupported Raney-nickel catalystw as also used.[12] The industrial method for the hydrogenation of squalenei nto squalane involves an ickel-Kieselguhr catalyst under 4bar (1 bar = 0.1 MPa)o fH 2 pressure at 200 8C.[13] However,e xtensive purification is required to remove most of the nickel that leaches into the squalane product to meet the maximum acceptable levels of toxic nickel compounds. In one report, the reactiono ver Ni-based platinum catalysts resulted in extensive bond migration and dehydrogenation of squalene.[14] Phytosqualane was obtained [15] from trans-b-farnesene.[16] Recently,a ni mpressive advancementw as made by Pagliaroa nd co-workers, [17] who used SiliaCatPd 0 ,a no rganosilica ...

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confidence: 99%

Palladium‐Nanoparticles‐Intercalated Montmorillonite Clay: A Green Catalyst for the Solvent‐Free Chemoselective Hydrogenation of Squalene

Soni

Sharma

2016

ChemCatChem

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“…For instance industries have started employing green chemistry practices such as waste prevention by designing high performance heterogeneous catalysts based on naturally available materials and the use of less toxic solvents and reagents. [8][9][10][11] Palladium catalyzed cross-coupling reactions are important approaches for the formation of carbon-carbon and carbon-heteroatom bonds [12][13][14][15][16][17][18]. In recent years, because of high toxicity and price of palladium, growing interest has been paid to development of different heterogeneous palladium catalysts [19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

A fluorescence active catalyst support comprising carbon quantum dots and magnesium oxide doping for stabilization of palladium nanoparticles: Application as a recoverable catalyst for Suzuki reaction in water

Gholinejad

Bahrami

Nájera

2017

Molecular Catalysis

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Novel magnesium oxide-carbon quantum dots have been synthesized and used for the formation and stabilization of palladium nanoparticles. This highly water dispersible material, Pd@MgO-CQD, has been used as an active catalyst for Suzuki coupling of aryl bromides at room temperature and aryl chlorides at 80 °C in water. Using fluorescence emission of the material, a new protocol for determine of Pd loading and leaching in catalyst preparation and recycling process was developed.

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“…A whole series of different 75%-methyl modified ORMOSIL (organically modified silicate) catalysts doped with Pd 0 nanocrystals were prepared according to the alcohol-free sol-gel synthetic methodology described elsewhere [3], involving polycondensation of MeSi(OEt) 3 and Si(OEt) 4 precursors (Eq. 1): An alcohol-free sol undergoes further basic catalyzed polycondensation to yield a mesoporous hydrogel that is dried to afford a xerogel doped with Pd 2?…”

Section: Resultsmentioning

confidence: 99%

“…In this field, the new catalyst series SiliaCat Pd 0 (SiliaCat is a trademark of SiliCycle, Inc.) made of nanostructured Pd 0 organosilica xerogels was recently reported for application to truly heterogeneous carbon-carbon coupling [3], debenzylation [4] and hydrogenation [5] of functionalized nitroarenes reactions.…”

Section: Introductionmentioning

confidence: 99%