- Heterogeneously Catalyzed Hydrogenation of Squalene to Squalane under Mild Conditions
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The full chemoselective hydrogenation of highly unsaturated all-trans linear squalene into valuable fully saturated squalane is achieved smoothly under mild conditions over the sol-gel-entrapped Pd catalyst SiliaCat Pd0. The catalysis is truly heterogeneous, and the catalyst is stable and recyclable, which opens the route to an easier and less expensive hydrogenation of squalene.
- Pandarus, Valerica,Ciriminna, Rosaria,Kaliaguine, Serge,Béland, Fran?ois,Pagliaro, Mario
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- NEW INDUSTRIAL SYNTHESIS OF SQUALANE.
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Squalane is synthesized by the ethynylation reaction of geranylacetone with a complex of 1,3-butadiyne:N-methylpyrrolidone ( equals 1:1) in the presence of a KOH catalyst and by hydrogenation with a Raney nickel catalyst, followed by hydrogenation hydrogenolysis with a mixed catalyst of nickel/diatomaceous earth and silica-alumina. An alternative synthesis of squalane from dehydronerolidol is also achieved by oxidative coupling reaction with a copper(II) catalyst under a helium atmosphere.
- Nishida,Ninagawa,Itoi,Fujita
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- Palladium-Nanoparticles-Intercalated Montmorillonite Clay: A Green Catalyst for the Solvent-Free Chemoselective Hydrogenation of Squalene
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Squalane is an important ingredient in the cosmetic, nutraceutical, and pharmaceutical industries. It has also been used as a model compound for the hydrocracking of crude and microalgae oil. Thus, a series of green heterogeneous metal catalysts were prepared to achieve complete hydrogenation of highly unsaturated squalene into squalane. Surface modification of the clay and metal intercalation simultaneously occurred during wet impregnation. The Pd-nanoparticles-intercalated clay with a dominating Pd(1 1 1) facet showed the highest reactivity and selectivity. The catalyst was stable with very low Pd leaching (≈0.03 ppm) and was recyclable without losing any significant catalytic activity. Play with clay: Metal (Pt, Pd, and Ni)-intercalated clay catalysts are prepared, and their catalytic activity in the hydrogenation of squalene is tested. The clay/Pd catalyst shows the highest catalytic activity and selectivity in the chemoselective reduction of squalene under solvent-free conditions, and this is attributed to the highly faceted Pd(1 1 1) plane. This catalyst can be recycled without a significant loss of activity.
- Soni, Vineet Kumar,Sharma, Rakesh K.
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- SQUALENE AND SQUALANE OF HIGH QUALITY PRODUCED BY MICROWAVE ASSISTED PROCESS
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The present invention relates to a product comprising squalene according to Formula I in an amount of equal or more than 50 wt.-% related to the total weight of the product according to Formula I, the product being produced by a continuous flow, microwave assisted process comprising the steps: a) preparing a reaction mixture containing an oily or fatty material of plant origin and aqueous methanol or aqueous ethanol, b) continuously conveying of the reaction mixture through a microwave-transparent reaction zone and irradiating the reaction mixture with microwaves inside the reaction zone in the presence of an acidic catalyst, whereby the retention time of the reaction mixture in the microwave-transparent reaction zone is 1 s to 180 s, the temperature in the reaction zone being equal to or between 100 °C and 220 °C, the pressure in the reaction zone being 1.5 bar to 30 bar, wherein a reaction of the reaction mixture takes place in the reaction zone resulting in a mixture of polar substances comprising glycerol, methanol or ethanol, and water, and non-polar substances comprising fatty acid methylesters or fatty acid ethylesters and unsaponifiable components, c) releasing the pressure to ambient pressure, d) after phase separation the polar phase is separated from the non-polar phase containing the non-polar substances, e) separating fatty acid methylesters or fatty acid ethylesters from the non-polar phase by falling film evaporation or thin-layer evaporation, f) separating squalene according to Formula I from the unsaponifiable components by molecular distillation, short-pass distillation, extraction or freeze separation.
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Page/Page column 14
(2020/05/15)
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- Application of Silicon-Initiated Water Splitting for the Reduction of Organic Substrates
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The use of water as a donor for hydrogen suitable for the reduction of several important classes of organic compounds is described. It is found that the reductive water splitting can be promoted by several metalloids among which silicon shows the best efficiency. The developed methodologies were applied for the reduction of nitro compounds, N-oxides, sulfoxides, alkenes, alkynes, hydrodehalogenation as well as for the gram-scale synthesis of several substrates of industrial importance.
- Gevorgyan, Ashot,Mkrtchyan, Satenik,Grigoryan, Tatevik,Iaroshenko, Viktor O.
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p. 375 - 382
(2018/06/04)
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- CATALYTIC PROCESS FOR DIENE DIMERIZATION
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The invention relates to a process for the dimerization of conjugated diene compounds by a heterogeneous catalytic process using a supported palladium catalyst in the presence of at least one palladium activator and at least one palladium coordinating agent.
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Page/Page column 19; 20
(2018/02/28)
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- CATALYTIC PROCESS FOR DIENE DIMERIZATION
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The invention relates to a selective head-to-tail dimerization of conjugated diene compounds by a heterogeneous catalytic process using a supported catalyst comprising ligands and a transition metal selected from titanium and zirconium.
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Page/Page column 24; 26; 28
(2018/02/20)
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- Flow Dehydration and Hydrogenation of Allylic Alcohols: Application to the Waste-Free Synthesis of Pristane
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Hydroxy-substituted sulfonic acid functionalized silica (HO-SAS) in combination with THF containing a small amount of water as a solvent proved to be a reliable system for the dehydration of allylic alcohols. This process generally caused dehydration within 1 min through a column reactor charged with HO-SAS. The flow dehydration was sequenced by flow hydrogenation, which resulted in the synthesis of pristane. A scalable flow synthesis of pristane was successfully performed and afforded 10 g of pristane after an operation of 2 h. We also performed dehydration and hydrogenation by using a mixed column of HO-SAS and 10 % Pd/C.
- Furuta, Akihiro,Hirobe, Yuki,Fukuyama, Takahide,Ryu, Ilhyong,Manabe, Yoshiyuki,Fukase, Koichi
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supporting information
p. 1365 - 1368
(2017/03/23)
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- CATALYTIC PROCESS FOR DIENE DIMERIZATION
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The invention relates to a selective head-to-head dimerization of conjugated diene compounds by a catalytic process in a reaction medium without solvent or with solvent comprising hydrocarbons, in the presence of a specific additive of the phenol type.
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Page/Page column 15-17; 20-22
(2016/11/07)
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- SQUALANE AND ISOSQUALANE COMPOSITIONS AND METHODS FOR PREPARING THE SAME
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Provided herein are methods comprising catalytic dimerization of β-farnesene to obtain squalane and/or isosqualane. Compositions comprising squalane and/or isosqualane are provided. In certain embodiments, squalane and isosqualane prepared by the methods provided herein can be useful for applications in cosmetic industry and/or in the lubricants industry.
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Page/Page column 54-55; 59
(2011/12/04)
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- Lubricant compositions
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Compositions comprising a farnesane dimer and/or a farnesene dimer and a compound selected from squalene, squalene and dehydrosqualene are described. The compositions provided comprise conventional additives. Methods of making and using the compounds and composition are also disclosed.
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- Highly pure squalane, raw material for pharmaceuticals and cosmetics prepared by using the same and method for producing the same
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Highly pure squalane in which the content of pristane is reduced to 10 wt ppm or less, can be obtained by refining the squalane of animal oil or fat origin through thin film distillation, said highly pure squalane is useful as a raw material for producing cosmetics and medical and pharmaceutical preparations and especially, it is quite effective as a lubricating agent for condoms and as a component of adjuvant composition.
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- Electron Transfer Reactions and Mobile Holes in Radiolysis of Squalane. Time-Resolved FDMR Study
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Fluorescence detected magnetic resonance (FDMR) is applied to study ion-molecule reactions in squalane (2,6,10,15,19,23-hexamethyltetracosane).Several time-resolved pulsed FDMR experiments are suggested to measure rate constants of scavenging by aromatic solutes.These constants vary from 5E8 to 1.6E9 mol-1 dm3 s-1.The ion-molecule reactions of radical cations are somewhat slower than reactions of radical anions.The scavenging of the alkane hole is significantly faster than ion-molecule reactions of molecular cations.The mobile hole decays on a time scale of several tens of nanoseconds.These FDMR results are in accord with our recent work on transient absorption spectroscopy in radiolysis of squalane.
- Shkrob, I. A.,Trifunac, A. D.
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p. 14681 - 14687
(2007/10/03)
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- Complexes η3-allylpalladium : isomerisation et photolyse ; synthese du squalene
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Complexation of primary allylic chlorides in the presence of Pdo may lead to a mixture of syn and anti η3-allylpalladium complexes.Photolysis or thermolysis also causes syn-anti isomerisation.A mixture of squalene stereoisomers is obtained by photolysis of the η3-farnesylpalladium complexes.
- Muzart, J.,Pete, J. P.
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- 2-HYDROXYMETHYL-4-PHENYLTHIO-1-BUTENE AS A KEY COMPOUND FOR TOTAL SYNTHESIS OF ACYCLIC TERPENOIDS
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A new total synthesis of myrcene, citral, squalane, and isophytol employing 2-hydroxymethyl-4-phenylthio-1-butene as a starting material is described.
- Mandai, Tadakatsu,Yamaguchi, Hirofumi,Nishikawa, Kengo,Kawada, Mikio,Otera, Junzo
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p. 763 - 764
(2007/10/02)
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- Preparation of squalane by hydrogenolysis
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Novel 2,6,10,15,19,23-hexamethyltetracosane-10,15-diol derivatives. Such derivatives are prepared by hydrogenation of 2,6,10,15,19,23-hexamethyltetracosa-11,13-diyne-10,15-diol derivatives and used as starting materials for preparing squalane.
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- Process for preparing 2,6,10,15,19,23-hexamethyltetracosane
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A non-irritating base component useful for cosmetics and topical preparations consisting of 2,6,10,15,19,23-hexamethyltetracosane having a high stability and being very safe for use on skin are hereby disclosed. Said component is synthesized by (a) preparing diacetylene dialcohol by reacting at least one ketone selected from the group consisting of 6,10-dimethylundecan-2-one, 6,10-dimethylundeca-3,9-dien-2-one, 6,10-dimethylundeca-5,9-dien-2-one, 6,10-dimethylundeca-5,10-dien-2-one and 6,10-dimethylundeca-3,5,9-trien-2-one, with acetylene and then subjecting the reaction product to the oxidation coupling, or by reacting ketone with diacetylene and (b) hydrocracking the diacetylene dialcohol directly or after hydrogenation.
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- Diacetylene diol derivatives and process for preparing the same
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Novel 2,6,10,15,19,23-hexamethyltetracosa-11,13-diin-10,15-diol derivatives. Such derivatives are prepared by oxydative coupling of 3,7,11-trimethyldodeca-1-in-3-ol derivatives or by ethynylation of 6,10-dimethylundecan-2-on derivatives with diacetylene and used as starting materials for preparing squalane.
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