Catalytic Hydrogenation of Squalene to Squalane

Ciriminna, Rosaria; Pandarus, Valerica; Béland, François; Pagliaro, Mario

doi:10.1021/op5002337

Cited by 32 publications

(37 citation statements)

References 18 publications

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“…Over the years, deep-sea shark liver oil has been the major natural source of squalene (Ronco and De Stéfani, 2013; Popa et al, 2015; Rosales-Garcia et al, 2017a). It is estimated that for producing 1 ton of squalene, it demands as many as about 3,000 sharks (Ciriminna et al, 2014). A single distillation under vacuum at a temperature of 200–230°C is required for recovering >98% purified squalene from the liver oil (Ciriminna et al, 2014).…”

Section: Natural Sources Of Squalenementioning

confidence: 99%

Engineering Strategies in Microorganisms for the Enhanced Production of Squalene: Advances, Challenges and Opportunities

Gohil

Bhattacharjee

Khambhati

et al. 2019

Front. Bioeng. Biotechnol.

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The triterpene squalene is a natural compound that has demonstrated an extraordinary diversity of uses in pharmaceutical, nutraceutical, and personal care industries. Emboldened by this range of uses, novel applications that can gain profit from the benefits of squalene as an additive or supplement are expanding, resulting in its increasing demand. Ever since its discovery, the primary source has been the deep-sea shark liver, although recent declines in their populations and justified animal conservation and protection regulations have encouraged researchers to identify a novel route for squalene biosynthesis. This renewed scientific interest has profited from immense developments in synthetic biology, which now allows fine-tuning of a wider range of plants, fungi, and microorganisms for improved squalene production. There are numerous naturally squalene producing species and strains; although they generally do not make commercially viable yields as primary shark liver sources can deliver. The recent advances made toward improving squalene output from natural and engineered species have inspired this review. Accordingly, it will cover in-depth knowledge offered by the studies of the natural sources, and various engineering-based strategies that have been used to drive the improvements in the pathways toward large-scale production. The wide uses of squalene are also discussed, including the notable developments in anti-cancer applications and in augmenting influenza vaccines for greater efficacy.

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Section: Natural Sources Of Squalenementioning

confidence: 99%

Engineering Strategies in Microorganisms for the Enhanced Production of Squalene: Advances, Challenges and Opportunities

Gohil

Bhattacharjee

Khambhati

et al. 2019

Front. Bioeng. Biotechnol.

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“…The hydrogenation of unsaturated C−C bonds by using heterogeneous catalysts is an important industrial process . Among these processes, the chemoselective hydrogenation of highly unsaturated all‐ trans linear squalene into squalane is highly desirable . Squalane is an exceptional emollient with the distinct ability to penetrate human skin without feeling greasy and without harmful effects .…”

Section: Figurementioning

confidence: 99%

“…[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.…”

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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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“…1,2 At present, for one of the most promising derivative, i.e. [7][8][9] In general, the hydrogenation reactions have a crucial role in the preparation of required products for biorefinery and for the flavor, fragrance and pharmaceutical industries, [10][11][12][13][14][15] which are obtained from highly oxygenated biomasses by lowering their O/H ratio. [3][4][5] At the contrary, a useful building block for chemical and pharmaceutical processes, 1-propanol, 6 could be obtained by hydrogenation of 2-propen-1-ol, which, in turn, can be produced by deoxydehydration of glycerol, a by-product of biodiesel production, available in large amounts and at relatively low costs.…”

Section: Introductionmentioning

confidence: 99%

Hydrogenation of allyl alcohols catalyzed by aqueous palladium and platinum nanoparticles

et al. 2015

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A series of Pd and Pt nanoparticles (NPs) was prepared starting from the corresponding metal ions and lignosulphonates; NPs were tested as catalysts for allyl alcohols hydrogenation in water at room temperature and pressure. All NPs were active with sharp differences in conversions and selectivites: Pt NPs formed mainly saturated alcohols, whereas Pd NPS were more active, but less selective, forming, in addition to saturated alcohols, also isomeric unsaturated alcohols and aldehydes, both saturated and unsaturated.. Results and DiscussionWe prepared a series of twelve NPs using two metals (Pt and Pd) and six water-soluble lignins: Kraft lignin (KrLig), ammonium lignosulphonate (AmLig), calcium (CaLig) and sodium (NaLig) lignosulphonates and the corresponding lowsugar ones (CaROLig and NaROLig); lignins, in water solution and at 80 °C, acted as both reducing agents for the metal ions, i.e. H 2 PtCl 6 and PdCl 2 , and as stabilizing agents for the formed

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Catalytic Hydrogenation of Squalene to Squalane

Cited by 32 publications

References 18 publications

Engineering Strategies in Microorganisms for the Enhanced Production of Squalene: Advances, Challenges and Opportunities

Engineering Strategies in Microorganisms for the Enhanced Production of Squalene: Advances, Challenges and Opportunities

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

Hydrogenation of allyl alcohols catalyzed by aqueous palladium and platinum nanoparticles

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