111-01-3 Usage
Occurrence
Squalane is obtained through the hydrogenation of squalene, and can be used as the oily raw materials of balsam, nutritional emulsion and other basic cosmetics. Squalene was obtained from the liver oil of Centrophorus or other deep-sea shark. Initially, it is the byproduct during the Vitamin A production process from shark liver oil. In recent years, it has been found that unsaponifiable oil of olive oil is rich in squalene, which can be used as the raw material of production of squalane (i.e., fully hydrogenated squalene).
Physical and chemical properties
Refined squalane is a colorless, odorless, inert and transparent oily viscous liquid. Slightly soluble in methanol, ethanol, acetone and glacial acetic acid. It is miscible with benzene, chloroform, carbon tetrachloride, petroleum ether, ether, mineral oil and other animal and vegetable oils. The relative density (15 °C/ 4 ℃) 0.812, refractive index (15 ℃) 1.4530, iodine value 0 ~ 5, saponification value 0 ~ 5, acid value 0 ~ 0.2, freezing point -38 ℃, boiling point 350 ℃. It is stable in the air, but can be slowly oxidized upon the action of sunlight. Sebaceous glands can synthesize squalene. Sebum contain squalene at a content of 1% in children and up to 10% in adult; sebum contains a squalane mass fraction of about 2%. Its permeability, lubricity and breathability is better than other fats, matching well with most cosmetic raw materials.
Squalane application
Squalane is widely used as a cosmetic base and finishing cosmetics, precise machinery lubricants, perlite agent of medical ointment and advanced soap.
Squalane is a natural product, being inert and non-toxic. It has good affinity to human skin without irritating the skin and causing allergies. It can accelerate the penetration of other actives into the skin. Squalane is a high-grade cosmetic oily raw materials, such as various types of creams and lotions, eyeliners, eyeshadow and conditioner. Cosmetics is mostly natural product extracted directly from cod liver oil. Synthetic products have stimulating effect on the human body, only used as lubricants and UV agents.
Squalane is the most commonly used standard non-polar fixative with its polarity being set to zero. Such fixed liquid and component molecules is the dispersion force, mainly used for the separation of general hydrocarbons and non-polar compounds.
Preparation
It can be refined directly from the cod liver oil with refinement the first vacuum decompression obtained crude squalane, and then in the nickel catalyst, high temperature, high pressure hydrogenation, remove the double bond part, and then vacuum distillation available.
Synthesis method. Take isoprene as raw material; first apply chlorination of isoprene, generating methyl heptanone, followed by dehydrogenation to generate linalool; further apply linalool and geranyl acetone, finally generating squalane.
Squalene can be used as raw material with direct hydrogenation to obtain it.
Take olive oil as raw material, extract the squalene, and then perform hydrogenation to obtain it.
Linalool can react with ethyl acetoacetate to generate 3, 7, 11-trimethyl-dodecane-6, 10-dien-1-yn-3-ol; further use cuprous oxide as a catalyst for oxidation and coupling, hydrogenation to obtain the finished product of squalane.
Cooling Experiment
This product at -55 ℃ without losing its liquidity. Test based on the freezing-point determination method. The thermometer used was a low flow point thermometer, glass bath D, and put into dry ice and acetone for cooling.
Chemical Properties
viscous colourless liquid
Uses
Different sources of media describe the Uses of 111-01-3 differently. You can refer to the following data:
1. health foods
2. Squalane has been used: as solvent in the synthesis of Europium dibenzoylmethide triethylammonium, brightest known triboluminescent (TL) material;as lubricant for fatty acid surfactant films adsorbed on iron oxide surfaces
3. Lubricant, transformer oil. Ingredient of watch and chronometer oils. Perfume fixative. In pharmacy and cosmetics as skin lubricant, ingredient of suppositories, carrier of lipid-soluble drugs.
4. squalane is an excellent moisturizer and lubricant, it softens and smoothes the skin while also replenishing skin lipids. Its compatibility with skin lipids can be attributed to the fact that human sebum is made up of 25 percent squalane. Squalane has traditionally been obtained by hydrogenation of shark liver oil or other natural oils. Components found in fish oils may reduce skin irritation and allergic responses. It can also be derived from plant sources or synthetically manufactured.
Definition
A saturated hydrocarbon.
General Description
Dielectrophoretic deformation of thin liquid fillm of squalane has been investigated. Microfluidized squalenes are efficient adjuvants, eliciting both humoral and cellular immune responses.
Purification Methods
Purify squalane by fractional distillation in vacuo or evaporative distillation. It is soluble in pet ether, *C6H6, Et2O and CHCl3, slightly soluble in alcohols, Me2CO and AcOH but insoluble in H2O. Small quantities can be purified by TLC as for squalene below. It is used as a marker in GLC and HPLC. [Staudinger & Leupold Helv Chim Acta 15 223 1932, Sax & Stross Anal Chem 29 1700 1951, Mandai et al. Tetrahedron Lett 22 763 1981, Beilstein 1 IV 593.]
Check Digit Verification of cas no
The CAS Registry Mumber 111-01-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 1 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 111-01:
(5*1)+(4*1)+(3*1)+(2*0)+(1*1)=13
13 % 10 = 3
So 111-01-3 is a valid CAS Registry Number.
InChI:InChI=1/C30H62/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h25-30H,9-24H2,1-8H3
111-01-3Relevant articles and documents
Heterogeneously Catalyzed Hydrogenation of Squalene to Squalane under Mild Conditions
Pandarus, Valerica,Ciriminna, Rosaria,Kaliaguine, Serge,Béland, Fran?ois,Pagliaro, Mario
, p. 2071 - 2076 (2015)
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.
Palladium-Nanoparticles-Intercalated Montmorillonite Clay: A Green Catalyst for the Solvent-Free Chemoselective Hydrogenation of Squalene
Soni, Vineet Kumar,Sharma, Rakesh K.
, p. 1763 - 1768 (2016)
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.
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Akutagawa,S. et al.
, p. 1158 - 1162 (1978)
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SQUALENE AND SQUALANE OF HIGH QUALITY PRODUCED BY MICROWAVE ASSISTED PROCESS
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Page/Page column 14, (2020/05/15)
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.
CATALYTIC PROCESS FOR DIENE DIMERIZATION
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Page/Page column 19; 20, (2018/02/28)
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.
Flow Dehydration and Hydrogenation of Allylic Alcohols: Application to the Waste-Free Synthesis of Pristane
Furuta, Akihiro,Hirobe, Yuki,Fukuyama, Takahide,Ryu, Ilhyong,Manabe, Yoshiyuki,Fukase, Koichi
supporting information, p. 1365 - 1368 (2017/03/23)
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.
