91-17-8

Basic information

• Product Name: Decahydronaphthalene
• Synonyms: Decahydronaphthalene, 99%, Mixture of cis and trans, anhydrous, AcroSeal;Decahydronaphthalene, SuperDry, J&KSeal;Ten hydrogen naphthalene;Decahydronapht;Decahydronaphthalene [Testing Methods for Sulfur in Crude Oil and Petroleum Products];Decahydronaphthalene, mixture of cis + trans anhydrous, >=99%;Decahydronaphthalene, mixture of cis + trans reagent grade, 98%;DECAHYDRONAPHTHALENE MIX CIS/TRANS TECHN
• CAS NO: 91-17-8
• Molecular Formula: C₁₀H₁₈
• Molecular Weight: 138.25
• EINECS: 202-046-9
• Product Categories: ACS and Reagent Grade Solvents;Amber Glass Bottles;Carbon Steel Cans with NPT Threads;Reagent;Reagent Grade Solvents;Semi-Bulk Solvents;Solvent Bottles;Solvent by Application;Solvent Packaging Options;Solvents
• Mol File: 91-17-8.mol

Chemical Properties

• Melting Point: −125 °C(lit.)
• Boiling Point: 189-191 °C(lit.)
• Flash Point: 57 °C
• Appearance: Clear/Liquid
• Density: 0.896 g/mL at 25 °C(lit.)
• Vapor Density: 4.76 (vs air)
• Vapor Pressure: 42 mm Hg ( 92 °C)
• Refractive Index: n20/D 1.474(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 0.006g/l (experimental)
• Explosive Limit: 0.7-4.9%, 100°F
• Water Solubility: 6 mg/L at 20 ºC
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with oxidizing agents. Combustible. May form explosive peroxides. Heat and light accelerate peroxide format
• Merck: 14,2846
• BRN: 878165
• CAS DataBase Reference: Decahydronaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: Decahydronaphthalene(91-17-8)
• EPA Substance Registry System: Decahydronaphthalene(91-17-8)

Safety Data

• Hazard Codes: C,N,Xi
• Statements: 20-34-51/53-36/37/38-65
• Safety Statements: 26-36/37/39-45-60-24/25-23-62-61
• RIDADR: UN 1147 3/PG 3
• WGK Germany: 1
• RTECS: QJ3150000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 91-17-8(Hazardous Substances Data)

Usage

Chemical and Physical Properties

Decahydronaphthalene has a molecular weight of 138.254 g/mol, a monoisotopic mass of 138.141 g/mol and an exact mass of 138.141 g/mol. It has a heavy atom count of 10 and a complexity of 80.6. It is a clear, colorless liquid with a characteristic odor that resembles that of methanol. Decahydronaphthalene has a flash point of 134°F?and it is less dense than water. It indicates poor solubility in water at 250℃ and its vapours are denser than air. It has a density of 0.89 at 68°F220℃. Decalin is very soluble in chloroform, ether, methanol and alcohol, and it is miscible with isopropyl alcohol, propyl, esters and a majority of the ketones. Decalin has a boiling point of 383/ 155.50℃ at 760 mm Hg and a melting point of -44°F -40°C. After long periods of exposure, Decalin forms toxic concentrations of peroxides. When Decalin is heated to decomposition, it released acrid fumes and smoke.

Preparation

Decahydronaphthalene is prepared by the hydrogenation of tetralin at low pressure with rhodium as the catalyst. Decalin can be oxidized to yield a significant amount of the hydroperoxide derivative. The cis isomer of Decahydronaphthalene can be oxidized at a higher rate than the combination of the trans and cis isomers, or the trans isomer solely. Therefore, when Decahydronaphthalene is synthesized through the hydrogenation of an unsaturated homolog such as 1,2,3,4-tetrahydronaphthalene for application in the synthesis of hydroperoxide, the resulting product is made of the cis isomer primarily. This method results in Decahydronaphthalene that is saturated with the cis isomer. Such high-pressure processes are technical to execute, and they are relatively expensive. A low-pressure preparation process that entails the hydrogenation of tetralin to obtain cis Decahydronaphthalene is yet to be developed. The rhodium catalyst is maintained on an inert support such as carbon or alumina, and the reaction is best conducted in the presence of a solvent, which may include a lower saturated carboxylic acid such as acetic acid. Other solvents such as propionic acid, mineral acids and non-acid solvents which may consist of water, hydrocarbons, ethers, esters, amines, amides and alcohol can also be used. The portion of the solvent should be one in which the reaction apparatus can withstand, while in some instances it may be best to omit the solvent. Acetic acid yields a higher rate of the cis isomer when it is applied as the solvent as opposed to the application of alumina as the support substance for the catalyst. The rhodium catalyst is applied as the hydrogenation catalyst, and it is best prepared through reduction of rhodium salts, which may include oxide or chloride. The progress of the hydrogenation reaction may depend on the quantity of the rhodium catalyst applied to the reaction. The tetralin to rhodium ratio is also dependent on the positioning of rhodium with an inert support, the configuration of the support and the apparatus used during the hydrogenation process. For instance, if the rhodium catalyst on an inert support such as carbon or alumina is about 5%, the reaction will yield satisfactory results. Furthermore, approximately 12-25g of the catalyst per mole of the Tetralin may result in satisfactory results. The optimum temperatures for this reaction are 50 C but the rate of the reaction may increase if the temperature is increased gradually from approximately 200 C250 C. The main advantage of this method is the fact that it can be conducted under low pressures of hydrogen, which may be as low as 0.5 atmospheres. Based on the above catalyst concentrations and reaction conditions, the total conversion of tetralin to Decahydronaphthalene may be obtained in about 1-2 hours. This reaction also yields the cis isomer which could be more than 90% of the product, which is relative to the total hydrogenation process which may be ascertained by the absorption of the theoretical amount of hydrogen by tetralin. To attain the desired cis Decahydronaphthalene, the reaction contents should be passed through a conventional fractional distillation to remove any trans isomers. It is fundamental to exercise care while conducting the distillation process using a basic packed column to yield a chromatographically pure cis Decahydronaphthalene.

Hazard Statements

Decalin is a flammable liquid, and it may also cause acute toxicity upon inhalation. It may cause skin irritation/corrosion upon contact as well as severe eye irritation/damage.

Production Methods

Decalin occurs naturally in crude oil and is produced commercially by the catalytic hydrogenation of naphthalene. It is also a product of combustion and is released from natural fires.

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

Saturated aliphatic hydrocarbons, such as Decahydronaphthalene, may be incompatible with strong oxidizing agents like nitric acid. Charring of the hydrocarbon may occur followed by ignition of unreacted hydrocarbon and other nearby combustibles. In other settings, aliphatic saturated hydrocarbons are mostly unreactive. They are not affected by aqueous solutions of acids, alkalis, most oxidizing agents, and most reducing agents. Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154].

Health Hazard

Inhalation or ingestion irritates nose and throat, causes numbness, headache, vomiting; urine may become blue. Irritates eyes. Liquid de-fats skin and causes cracking and secondary infection; eczema may develop.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

Moderately toxic by inhalation and ingestion. Questionable carcinogen with experimental carcinogenic and neoplastigenic data. Mildly toxic by skin contact. Human systemic effects by inhalation: conjunctiva irritation, unspecified olfactory and pulmonary system changes. Can cause kidney damage. Mutation data reported. A skin and eye irritant. Flammable liquid when exposed to heat or flame, can react with oxidzing materials. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and fumes.

Environmental fate

Photolytic. The following rate constants were reported for the reaction of decahydronaphthalene and OH radicals in the atmosphere: 1.96 x 10-11 and 2.02 x 10-11 cm3/molecule?sec at 299 K for cis and trans isomers, respectively (Atkinson, 1985). A photooxidation reaction rate constant of 2.00 x 10-11 was reported for the reaction of decahydronaphthalene (mixed isomers) and OH radicals in the atmosphere at 298 K (Atkinson, 1990). Chemical/Physical. Decahydronaphthalene will not hydrolyze because it has no hydrolyzable functional group.

Purification Methods

Then the organic phase is separated, washed with water, saturated aqueous Na2CO3, again with water, dried with CaSO4 or CaH2 (and perhaps dried further with Na), filtered and distilled under reduced pressure (b 63-70o/10mm). It has also been purified by repeated passage through long columns of silica gel previously activated at 200-250o, followed by distillation from LiAlH4 and storage under N2. Type 4A molecular sieves can be used as a drying agent. Storage over silica gel removes water and other polar substances. [For the separation of cis and trans isomers see Seyer & Walker J Am Chem Soc 60 2125 1938, and Baker & Schuetz J Am Chem Soc 69 1250 1949.]

InChI:InChI=1/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2/t9-,10+

Upstream product

• 91-20-3 naphthalene 
• 119-64-2 tetralin 
• 90-15-3 α-naphthol 
• 85-01-8 phenanthrene 
• 135-19-3 β-naphthol 
• 493-03-8 1,2,3,4,5,6,7,8-octahydro-naphthalene 
• 75-76-3 tetramethylsilane 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 1579-21-1 2-decalone 
• 3618-12-0 Cyclodecene 
• 85807-82-5 1,2-Bis-(2-iodo-ethyl)-cyclohexane 
• 85807-82-5 cis-1,2-bis(2-iodoethyl)cyclohexane 
• 80025-15-6 1,2,5,6-Tetrahydronaphthalin 
• 20432-40-0 (E)-penta-2,4-dienal 

Downstream Products

• 29528-30-1 2-(2-pyridyl)aniline 
• 244-69-9 γ-carboline 
• 244-76-8 α-carboline 
• 15264-63-8 5-(pyridin-4-yl)-1,3,4-oxadiazol-2(3H)-thione 
• 1884-68-0 tetraphenylthiophene 
• 492-70-6 1,2-diphenyl-1,2-ethanediol 
• 655-48-1 DL-1,2-diphenylethane-1,2-diol 
• 130-80-3 Clinestrol 
• 130-80-3 3,4-bis-(4-propionyloxy-phenyl)-hex-3c-ene 
• 725-12-2 2,5-bis-(phenyl)-1,3,4-oxadiazole 
• 93-97-0 benzoic acid anhydride 
• 774-55-0 6-Acetyl-1,2,3,4-tetrahydronaphthalene 
• 588-59-0 stilbene 
• 806-69-9 1,2,3,4-tetraphenylbutane 

Relevant articles and documents

Inhibition of the hydrogenation of tetralin by nitrogen and sulfur compounds over Ir/SBA-16

In this work we study the catalytic properties of 5 wt.% Ir-containing SBA-16 catalysts (with and without aluminum as heteroatom), in the hydrogenation of tetralin to decalin, in the presence of 100 ppm of N as quinoline, indole and carbazole, and 100 ppm of S as dibenzothiophene and 4,6-dimethyl- dibenzothiophene at 250 °C and 15 atm of pressure of hydrogen, using a Parr reactor. Ir/SBA-16 and Ir/Al-SBA-16 were prepared by wetness impregnation using Iridium Acetylacetonate as source of Ir. The Ir/SBA-16 catalyst synthesized by us had high activity measured in tetralin hydrogenation at mild conditions. The experimental data was quantitatively represented by a modified Langmuir-Hinshelwood type rate equation, using the apparent adsorption constants calculated from the inhibition results for the individual compounds. The catalyst showed a good resistance to sulfur and nitrogen compounds. The inhibiting effect increased in the order: DBT quinoline 4,6-dimethyl-DBT indole carbazole. The inhibiting effect of the nitrogen/sulfur compounds was strong, but the activity was still higher than with commercial NiMo/alumina catalyst. We present in this contribution a successfully developed, high loaded and well dispersed Ir/SBA-16 catalysts, that have been shown to maintain a useful catalytic activity, even in the presence of relatively high amounts of sulfur compounds (up to 100 ppm, sulfur basis). Consequently, economically successful processes have evolved, based on this class of catalysts.

Fabricating nickel phyllosilicate-like nanosheets to prepare a defect-rich catalyst for the one-pot conversion of lignin into hydrocarbons under mild conditions

The one-pot conversion of lignin biomass into high-grade hydrocarbon biofuels via catalytic hydrodeoxygenation (HDO) holds significant promise for renewable energy. A great challenge for this route involves developing efficient non-noble metal catalysts to obtain a high yield of hydrocarbons under relatively mild conditions. Herein, a high-performance catalyst has been prepared via the in situ reduction of Ni phyllosilicate-like nanosheets (Ni-PS) synthesized by a reduction-oxidation strategy at room temperature. The Ni-PS precursors are partly converted into Ni0 nanoparticles by in situ reduction and the rest remain as supports. The Si-containing supports are found to have strong interactions with the nickel species, hindering the aggregation of Ni0 particles and minimizing the Ni0 particle size. The catalyst contains abundant surface defects, weak Lewis acid sites and highly dispersed Ni0 particles. The catalyst exhibits excellent catalytic activity towards the depolymerization and HDO of the lignin model compound, 2-phenylethyl phenyl ether (PPE), and the enzymatic hydrolysis of lignin under mild conditions, with 98.3% cycloalkane yield for the HDO of PPE under 3 MPa H2 pressure at 160 °C and 40.4% hydrocarbon yield for that of lignin under 3 MPa H2 pressure at 240 °C, and its catalytic activity can compete with reported noble metal catalysts.

Palladium Nanoparticles in Hypercrosslinked Polystyrene: Synthesis and Application in the Hydrogenation of Arenes

Abstract: A novel method for incorporation of palladium nanoparticles into a poroushypercrosslinked polystyrene matrix has been developed. The composite obtainedby reduction of [Pd(π-allyl)Cl]2 with hydrogen insupercritical CO2 shows high catalytic activity in thehydrogenation of benzene and can be used twelve (12) times in a row without anydecrease in conversion rate. The catalyst is also suitable for quantitativehydrogenation of toluene, tetralin and phenol. The obtained catalytic system iscompared with the palladium composite synthesized by a conventional method basedon hypercrosslinked polystyrene.

Aromatic compound hydrogenation and hydrodeoxygenation method and application thereof

The invention belongs to the technical field of medicines, and discloses an aromatic compound hydrogenation and hydrodeoxygenation method under mild conditions and application of the method in hydrogenation and hydrodeoxygenation reactions of the aromatic compounds and related mixtures. Specifically, the method comprises the following steps: contacting the aromatic compound or a mixture containing the aromatic compound with a catalyst and hydrogen with proper pressure in a solvent under a proper temperature condition, and reacting the hydrogen, the solvent and the aromatic compound under the action of the catalyst to obtain a corresponding hydrogenation product or/and a hydrodeoxygenation product without an oxygen-containing substituent group. The invention also discloses specific implementation conditions of the method and an aromatic compound structure type applicable to the method. The hydrogenation and hydrodeoxygenation reaction method used in the invention has the advantages of mild reaction conditions, high hydrodeoxygenation efficiency, wide substrate applicability, convenient post-treatment, and good laboratory and industrial application prospects.

Supported noble metal catalyst with a core-shell structure for enhancing hydrogenation performance

Supported noble metal nanoparticles are a kind of high efficiency of catalysts in aromatics hydrogenation, and the properties and structures of supports are of great importance to improve hydrogenation behaviors. In this work, an efficient Pd/S-1@ZSM-5 core-shell catalyst with an enhanced naphthalene hydrogenation ability was prepared by building acidic nano-ZSM-5 shells surrounding silicalite-1 supported Pd NPs. The acidic nano-ZSM-5 shell can strengthen the spillover hydrogenation due to the increase of the strong acid sites around Pd NPs, and the strong acid sites around metal NPs can be regulated by controlling the coverage of nano-ZSM-5 shell. Additionally, the formed mesoporous structure of nano-ZSM-5 shell is beneficial for the diffusion of bulky reactants. These are the two important factors for enhancing hydrogenation ability of Pd/S-1@ZSM-5 catalyst. Furthermore, Pd/S-1@ZSM-5 catalyst also shows good sulfur-tolerance in the presence of thionaphthene. This work presents an elegant example for enhancing hydrogenation abilities of noble metal catalysts by constructing a core-shell structure.

A new precursor for synthesis of nickel-tungsten sulfide aromatic hydrogenation catalyst

The unsupported NiWS-catalyst was obtained from the precursor [Ph3S]2Ni(WS4)2 in a hydrocarbon medium (in situ) for hydrogenation bicyclic aromatic compounds. The precursor [Ph3S]2Ni(WS4)2 and the catalyst prepared on its basis were studied by the X-ray diffraction and X-ray absorption methods, XPS and TEM. It was found that the new catalyst formed in situ contains tungsten sulfide and nickel sulfide nanophases. Tungsten sulfide, which has a layered structure, partially forms an insertion compound with nickel that enters between the WS2 layers and bonds covalently to sulfur. The proposed catalyst has proved to be active in the hydrodearomatization processes of model aromatic compounds (naphthalene, methylnaphthalenes) and exhibited the maximum selectivity with the formation of decalins compared to other earlier studied catalysts formed from other precursors in the reaction medium.

Chemoselective and Tandem Reduction of Arenes Using a Metal–Organic Framework-Supported Single-Site Cobalt Catalyst

The development of heterogeneous, chemoselective, and tandem catalytic systems using abundant metals is vital for the sustainable synthesis of fine and commodity chemicals. We report a robust and recyclable single-site cobalt-hydride catalyst based on a porous aluminum metal–organic framework (DUT-5 MOF) for chemoselective hydrogenation of arenes. The DUT-5 node-supported cobalt(II) hydride (DUT-5-CoH) is a versatile solid catalyst for chemoselective hydrogenation of a range of nonpolar and polar arenes, including heteroarenes such as pyridines, quinolines, isoquinolines, indoles, and furans to afford cycloalkanes and saturated heterocycles in excellent yields. DUT-5-CoH exhibited excellent functional group tolerance and could be reusable at least five times without decreased activity. The same MOF-Co catalyst was also efficient for tandem hydrogenation–hydrodeoxygenation of aryl carbonyl compounds, including biomass-derived platform molecules such as furfural and hydroxymethylfurfural to cycloalkanes. In the case of hydrogenation of cumene, our spectroscopic, kinetic, and density functional theory (DFT) studies suggest the insertion of a trisubstituted alkene intermediate into the Co–H bond occurring in the turnover limiting step. Our work highlights the potential of MOF-supported single-site base–metal catalysts for sustainable and environment-friendly industrial production of chemicals and biofuels.

Short time synthesis of titania modified-CMK-3 carbon mesostructure as support for Ir-catalyst applied in catalytic hydrotreating

Ti-CMK-3 carbon mesoporous was prepared using a novel synthesis method. This new method avoids the hard template synthesis used commonly. The method developed here, allows to reduce time, energy consumptionand cost. Structural and textural characterization of the titanium modified-mesoporous carbonwas performed by N2 adsorption, XRD, UV–vis-DRS, Raman spectroscopy and TEM. The characterization results indicated that the textural and structural properties of the material synthesized by the short time method are comparable with the properties of the material prepared by the hard template method. Ti modified-mesoporous carbon was used as support of the iridium nanoparticles, in order to prepare a catalyst to be tested in model hydrotreating reactions. The catalyst obtained by wet impregnation with iridium acetylacetonate were characterized by ICP-AES, H2 chemisorption, TEM, XPS and FTIR of adsorbed pyridine. The high Ir dispersion and small particle size, along with the moderate Lewis acidity generated by the presence of titanium in the support, were responsible for the good performance and stability of the catalyst in the hydrogenation of tetralin in presence of nitrogen compounds. Main advantage of the present study is the reduction of time and cost in the synthesis of the new material and the applicability for HDT reactions.

Fused-ring alkane fuel and photocatalytic preparation process thereof

A process for preparing a fused-ring alkane fuel, wherein the fused-ring alkane fuel has the following structure: wherein n is 1 or 2; R1, R2, R3, R4 and R5 are H or —CH3 or —CH2CH3; the fused-ring alkane fuel has a density of greater than 0.870 g/cm3, a freezing point of not higher than ?50° C., and a net mass heat value of not less than 42.0 MJ/kg; the process for preparing a fused-ring alkane fuel, wherein the process includes steps of: (1) in a presence of ultraviolet light and a photocatalyst, a Diels-Alder cycloaddition reaction between a substituted or unsubstituted cyclic enone and a substituted or unsubstituted furan molecule occurs to produce a fuel precursor molecule: (2) the fuel precursor molecule obtained in the step (1) is subjected to hydrodeoxygenation to produce the fused-ring alkane fuel.

Preparation of highly active unsupported Ni–Si–Mo catalyst for the deep hydrogenation of aromatics

A mesoporous nickel-silicon-molybdenum composite oxide with the phase of ammonium nickel (or silicon) molybdate was synthesized by chemical precipitation and unsupported nickel-silicon-molybdenum sulfide catalysts with various Ni/Si ratios were obtained by sulfidation of the oxide precursors. The oxide precursors and unsupported sulfide catalysts were characterized by XRD, N2 adsorption-desorption, SEM, TPR, and HRTEM. The unsupported nickel-silicon-molybdenum sulfide catalysts were tested in the hydrogenation of naphthalene. It was found that the introduction of Si could increase the specific surface area and improve the pore structure of precursors, and reduce the reduction temperature of Mo species. The results of naphthalene hydrogenation showed that the introduction of Si could significantly improve the hydrogenation activity of the catalysts, especially the Ni9.5Si0.5Mo10 catalyst exhibited the highest aromatic hydrogenation activity at low temperature. Interestingly, it is found that the tetralin selectivity is 100% in the low temperature range (220–260 °C) over Si10Mo10 catalyst, which might be attractive in the production of tetralin and other industrial application.