91-17-8 Usage
Description
Decahydronaphthalene also referred to as Decalin is an organic compound that dissolves rubber, resins, waxes, fats, and oils. It is a colorless, aromatic hydrocarbon which is used as an alternative to turpentine, as a cleaning fluid and as a stain remover. Decahydronaphthalene was also used as a varnish remover for oil-based paintings in the past.
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.
Chemical Properties
colourless liquid
Physical properties
Clear, colorless, flammable liquid with a mild methanol or hydrocarbon-like odor
Uses
Different sources of media describe the Uses of 91-17-8 differently. You can refer to the following data:
1. Solvent for naphthalene, waxes, fats, oils, resins, rubbers; motor fuel and lubricants;
cleaning machinery; substitute for turpentine; shoe-creams; stain remover.
2. Solvent for naphthalene, fats, resins,
oils; alternate for turpentine in lacquers, shoe
polishes, and waxes; component in motor fuels
and lubricants
3. Decahydronaphthalene is widely used as an industrial solvent for resins and fuel additives. It is a substitute for turpentine in lacquers, shoe polishes and waxes.
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.
Definition
ChEBI: An ortho-fused bicyclic hydrocarbon that is the decahydro- derivative of naphthalene.
General Description
A clear colorless liquid with an aromatic odor. Flash point 134°F. Less dense than water and insoluble in water. Vapors heavier than air.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 91-17-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 1 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 91-17:
(4*9)+(3*1)+(2*1)+(1*7)=48
48 % 10 = 8
So 91-17-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2/t9-,10+
91-17-8Relevant articles and documents
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Sternberg et al.
, p. 186 (1967)
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Fabricating nickel phyllosilicate-like nanosheets to prepare a defect-rich catalyst for the one-pot conversion of lignin into hydrocarbons under mild conditions
Cao, Meifang,Chen, Bo,He, Chengzhi,Ouyang, Xinping,Qian, Yong,Qiu, Xueqing
supporting information, p. 846 - 857 (2022/02/09)
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.
Supported noble metal catalyst with a core-shell structure for enhancing hydrogenation performance
Lu, Ningyue,Zhao, Jiaxin,Dong, Qi,Zhao, Yanpeng,Fan, Binbin
, (2021/04/12)
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.
Chemoselective and Tandem Reduction of Arenes Using a Metal–Organic Framework-Supported Single-Site Cobalt Catalyst
Akhtar, Naved,Begum, Wahida,Chauhan, Manav,Manna, Kuntal,Newar, Rajashree,Rawat, Manhar Singh
supporting information, (2022/01/19)
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.
