108-08-7

Basic information

• Product Name: 2,4-DIMETHYLPENTANE
• Synonyms: dimethylpentane(non-specificname);pentane,2,4-dimethyl-;2,4-DIMETHYLPENTANE;DIISOPROPYLMETHANE;Dimethylpentane;2,4-DIMETHYLPENTANE, STANDARD FOR GC;Heptan und Isomere;2,4-DIMETHYLPENTANE 99+%
• CAS NO: 108-08-7
• Molecular Formula: C₇H₁₆
• Molecular Weight: 100.2
• EINECS: 203-548-0
• Product Categories: Acyclic;Alkanes;Organic Building Blocks;Alphabetic;D;DID - DINChemical Class;Hydrocarbons;Neats;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 108-08-7.mol

Chemical Properties

• Melting Point: −123 °C(lit.)
• Boiling Point: 80 °C(lit.)
• Flash Point: 10 °F
• Appearance: /
• Density: 0.673 g/mL at 25 °C(lit.)
• Vapor Density: 3.48 (vs air)
• Vapor Pressure: 3.29 psi ( 37.7 °C)
• Refractive Index: n20/D 1.381(lit.)
• Solubility: Soluble in acetone, benzene, chloroform, alcohol and ether.
• PKA: >14 (Schwarzenbach et al., 1993)
• Explosive Limit: ~7%
• Water Solubility: 4.41mg/L(25 oC)
• BRN: 1696855
• CAS DataBase Reference: 2,4-DIMETHYLPENTANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIMETHYLPENTANE(108-08-7)
• EPA Substance Registry System: 2,4-DIMETHYLPENTANE(108-08-7)

Safety Data

• Hazard Codes: F,Xn,N
• Statements: 11-38-50/53-65-67
• Safety Statements: 9-16-29-33-60-61-62
• RIDADR: UN 3295 3/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 108-08-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2,4-DIMETHYLPENTANE is used as a chemical intermediate for the synthesis of various compounds, including WeiNiGuan. It serves as a crucial building block in the production of this compound, which has its own set of applications.
Used in Binder and Coating Industry:
In the binder and coating industry, 2,4-DIMETHYLPENTANE is utilized as a solvent or a component in the formulation of various products. Its ability to dissolve and mix with other substances makes it a valuable asset in this field.
Used in Resin Fiber Synthesis:
2,4-DIMETHYLPENTANE is also used in the synthesis of resin fiber, a material with a wide range of applications, including in the production of plastics, textiles, and other industrial products.
Used as Intermediates and Adhesives in Oil Drop Coagulation Thickener:
2,4-DIMETHYLPENTANE serves as an intermediate in the production of oil drop coagulation thickeners, which are used in various industrial processes to control the viscosity and consistency of fluids. Additionally, it is used as an adhesive in this application, providing a strong bond between different components.

Source

In diesel engine exhaust at a concentration of 0.3% of emitted hydrocarbons (quoted, Verschueren, 1983). Schauer et al. (1999) reported 2,4-dimethylpentane in a diesel-powered medium-duty truck exhaust at an emission rate of 410 μg/km. California Phase II reformulated gasoline contained 2,2-dimethylbutane at a concentration of 15,700 mg/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 2.92 and 354 mg/km, respectively (Schauer et al., 2002).

Environmental fate

Photolytic. Based on a photooxidation rate constant of 5.0 x 10-12 cm3/molecule?sec for the reaction of 2,3-dimethypentane and OH radicals in air, the half-life is 27 h (Alltshuller, 1991). Chemical/Physical. Complete combustion in air yields carbon dioxide and water vapor. 2,4- Dimethylpentane will not hydrolyze because it has no hydrolyzable functional group.

Purification Methods

Extract it repeatedly with conc H2SO4, wash with water, dry and distil it. Alternatively percolated it through silica gel (previously heated in nitrogen to 350o). Purify it by azeotropic distillation with EtOH, followed by washing out the EtOH with water, drying and distilling. [Beilstein 1 IV 406.]

InChI:InChI=1/C7H16/c1-6(2)5-7(3)4/h6-7H,5H2,1-4H3

Upstream product

• 1000-86-8 2,4-Dimethyl-1,3-pentadiene 
• 187737-37-7 propene 
• 75-28-5 Isobutane 
• 78-78-4 methylbutane 
• 565-59-3 2,3-dimethyl pentane 
• 74-85-1 ethene 
• 142-82-5 n-heptane 
• 24556-57-8 2-iodo-2,4-dimethylpentane 
• 625-06-9 2,4-dimethyl-2-pentanol 
• 625-65-0 2,4-dimethyl-2-pentene 
• 78757-65-0 1-isopropyl-2-methyl-cyclopropane 
• 589-34-4 3-methyl-hexane 
• 4127-47-3 2,2,3,3-tetramethylcyclopropane 
• 565-80-0 2,4-dimethylpentan-3-one 

Downstream Products

• 597-45-5 2,4-dimethyl-2-nitropentane 
• 565-59-3 2,3-dimethyl pentane 
• 123-44-4 2,2,4-trimethyl-1-pentanol 
• 76426-52-3 2,4,4,5,5,7-Hexamethyloctan 
• 18593-92-5 2-Isopropyl-3-methyl-1-butanol 
• 625-06-9 2,4-dimethyl-2-pentanol 
• 591-76-4 2-Methylhexane 
• 589-34-4 3-methyl-hexane 
• 2532-58-3 cis-1,3-dimethylcyclopentane 
• 1759-58-6 trans-1,3-dimethylcyclopentane 
• 108-88-3 toluene 
• 71-43-2 benzene 
• 142-82-5 n-heptane 
• 464-06-2 triptane 

Relevant articles and documents

Ring-opening of Alkyl-substituted Cyclopropanes in the Presence of Hydrogen on Copper

In the presence of hydrogen on copper, the cyclopropanes (1), (2), and (3) are transformed into saturated hydrocarbons containing the same number of carbon atoms (alkenes are also formed, through isomerization of the cyclopropanes); these studies reveal the importance of a previously unknown property of copper in heterogeneous metal catalysis.

Activation and isomerization of hydrocarbons over WO3/ZrO2 catalysts. II. Influence of tungsten loading on catalytic activity: Mechanistic studies and correlation with surface reducibility and tungsten surface species

We studied the correlation among the catalytic behavior of WO3/ZrO2 samples toward unsaturated and saturated hydrocarbons transformation, tungsten surface species oxidation states, and the crystallographic structure of the zirconia support. Different tungsten-loaded catalysts were studied, from 9 wt% (near-monolayer coverage) to 30 wt%. The resulting WO3/ZrO2 materials were obtained by impregnation of a tungsten salt on either a commercially available monoclinic zirconia or an amorphous hydroxide, ZrOx(OH)4-2x, followed by a calcination step (according to the Hino and Arata procedure), leading to a tetragonal structure. In contrast to previous works, here we demonstrate that the crystallographic structure of zirconia has no influence on catalytic properties. Correlations with XPS analyses revealed two aspects of catalytic behavior that depend strongly on the catalyst reducibility and thus on the W surface species oxidation states. First, on hardly reducible (tungsten loadings a purely acidic monomolecular mechanism for both isomerization (largely predominant) and cracking reactions, associated with W6+ and W5+ surface species, was demonstrated. Second, on easily reducible (tungsten loadings >15 wt%) or deeply reduced (over 723 K) surfaces, a bifunctional mechanism associating dehydrogenating/hydrogenating properties occurring on metallic tungsten and acidic isomerization and cracking on W5+ and W6+ surface species was observed. However, in this last case, we could not exclude the participation of a purely metallic isomerization mechanism occurring through σ-alkyl adsorbed species on the β-W metallic phase. A more pronounced reduction then led to an increase in the extensive hydrogenolysis mechanism, causing catalyst deactivation.

Reaction Mechanisms of Isomerization and Cracking of Heptane on Pd/H-Beta Zeolite

Tha vapor-phase isomerization and cracking of heptane on H-Beta zeolites loaded with various amounts of Pd metal has been studied at a temperature of 505 K and at a total pressure of 0,3 MPa.The cracking of heptane is interpreted as a combination of classic bifunctional hydrocracking and dimerization cracking.The isomerization of heptane proceeds through the classic-bifunctional mechanism and a second mechanism involving dimerization cracking.The contribution of the different mechanisms to the izomerization and cracking is derived from the formation of specific reaction products.The contribution of the different mechanisms is dependent on the Pd content of the zeolite.

Selective methylative homologation: An alternate route to alkane upgrading

InI3 catalyzes the reaction of branched alkanes with methanol to produce heavier and more highly branched alkanes, which are more valuable fuels. The reaction of 2,3-dimethylbutane with methanol in the presence of InI3 at 180-200°C affords the maximally branched C7 alkane, 2,2,3-trimethylbutane (triptane). With the addition of catalytic amounts of adamantane the selectivity of this transformation can be increased up to 60%. The lighter branched alkanes isobutane and isopentane also react with methanol to generate triptane, while 2-methylpentane is converted into 2,3-dimethylpentane and other more highly branched species. Observations implicate a chain mechanism in which InI3 activates branched alkanes to produce tertiary carbocations which are in equilibrium with olefins. The latter react with a methylating species generated from methanol and InI 3 to give the next-higher carbocation, which accepts a hydride from the starting alkane to form the homologated alkane and regenerate the original carbocation. Adamantane functions as a hydride transfer agent and thus helps to minimize competing side reactions, such as isomerization and cracking, that are detrimental to selectivity.

Mechanism of Isomerization of Hydrocarbons on Metals. Part 9.-Isomerization and Dehydrocyclization of 2,3-Dimethyl(2-(13)C)pentane on a 10percent Pt-Al2O3 Catalyst

The isomerization, dehydrocyclization and hydrogenolysis of 2,3-dimethyl(2-(13)C)pentane have been studied at 260 deg C over a 10percent Pt-Al2O3 catalyst of low dispersion, under various hydrocarbon and hydrogen pressures.Most of the isomerization products are accounted for either by a bond-shift mechanism or by a cyclic mechanism involving 1,2-dimethylcyclopentane intermediate.The absence of significant scrambling of the label suggests that the rate-determining step in isomerization is the skeletal rearrangement of highly dehydrogenated species.The positive order as a function of hydrogen which is found (0.8-1.2) cannot then be taken as evidence that desorption is rate-determining.It is best explained by assuming multisite adsorption of hydrocarbon and competition with hydrogen for chemisorption on the same sites.The results provide argument in favour of a reactive rather than dissociative-type adsorption step.

Isomerization of n-Heptane over Pd-Loaded Silico-Alumino-Phosphate Molecular Sieves

Isomerization of n-heptane was studied on a series of bifunctional SAPO-based catalysts with contents of 0.1 wtpercent Pd.From results on temperature programmed desorption of NH3 it is deduced that the different molecular sieve structures contain nearly identical amounts of silicon substituting for phosphorus in the framework (0.3 to 0.5 silicon atoms per unit cell).Best activities and selectivities for branched heptane isomers are achieved with SAPO-11 and SAPO-31.SAPO-17 and SAPO-5 show substantially lower activities.With SAPO-5, there is a high cracking selectivity which is assumed to be caused by the reduced accessibility of parts of the bridged hydroxyl groups within the molecular sieve framework.Different locations of these acid sites are evidenced by infrared OH vibration spectra recorded after adsorption of n-heptane.

Mechanism of Isomerization of Hydrocarbons on Metals. Part 11.-Isomerization and Dehydrocyclization of (13)C-labelled 3-Methylhexanes on Pt-Al2O3 Catalysts

The isomerization, dehydrocyclization and hydrogenolysis of 3-methylhexane have been studied at 320-380 deg C over a series of Pt-Al2O3 catalysts with a metal dispersion extending from 0.05 to 1.The use of five labelled compounds, 3-methyl(1-(13)C), (2-(13)C), (3-(13)C), (6-(13)C)hexanes and 3-methyl((13)C)hexane, alloved distinction between the various parallel pathways.On all catalysts the predominant reaction was the isomerization according to a cyclic mechanism involving either 1,3-dimethyl-, 1,2-dimethyl- or ethyl-cyclopentane intermediates with a relative contribution of 60, 40 and 20 percent, respectively.These results are consistent wiith a dehydrocyclization scheme involving a metallocarbene as precursor and dicarbene or dicarbyne recombination as the rate-determining step.

Influence of the Br?nsted acidity, SiO2/Al 2O3 ratio and Rh-Pd content on the ring opening. Part II. Selective ring opening of methylcyclohexane

Monometallic and bimetallic Pd-Rh catalysts with various Rh/Pd atomic ratios (=0.5, 1 and 2) and a total metal charge of 1 wt% supported on SiO 2-Al2O3 (SIRAL 40, 20, 5) were studied for the ring opening of methylcyclohexane (MCH). The results were compared with those obtained previously for ring opening of decalin. It was found that the total acidity and the Br?nsted acidity of the support have a higher influence on the activity for ring opening of naphthenic bicycles than on the activity for opening single rings. The influence of the metal charge is more important on the reaction of MCH. All the catalysts display a high MCH conversion, which increases with the reaction temperature. The bimetallic catalyst with the Rh/Pd ratio equal to 2 and supported on SIRAL 40 has the highest yield to ring opening products.

Silica-supported dendrimer-palladium complex-catalyzed selective hydrogenation of dienes to monoolefins

The selective hydrogenation of cyclic and acyclic dienes to monoolefins occurs under very mild conditions, in the presence of silica-supported PAMAM-Pd complexes. The activity and selectivity of this reaction is sensitive to the dendrimer structure. These dendritic complexes display excellent recycle properties, retaining activity for up to eight recycles.

Alkanethiolate-capped palladium nanoparticles for selective catalytic hydrogenation of dienes and trienes

Selective hydrogenation of dienes and trienes is an important process in the pharmaceutical and chemical industries. Our group previously reported that the thiosulfate protocol using a sodium S-alkylthiosulfate ligand could generate catalytically active Pd nanoparticles (PdNP) capped with a lower density of alkanethiolate ligands. This homogeneously soluble PdNP catalyst offers several advantages such as little contamination via Pd leaching and easy separation and recycling. In addition, the high activity of PdNP allows the reactions to be completed under mild conditions, at room temperature and atmospheric pressure. Herein, a PdNP catalyst capped with octanethiolate ligands (C8 PdNP) is investigated for the selective hydrogenation of conjugated dienes into monoenes. The strong influence of the thiolate ligands on the chemical and electronic properties of the Pd surface is confirmed by mechanistic studies and highly selective catalysis results. The studies also suggest two major routes for the conjugated diene hydrogenation: the 1,2-addition and 1,4-addition of hydrogen. The selectivity between two mono-hydrogenation products is controlled by the steric interaction of substrates and the thermodynamic stability of products. The catalytic hydrogenation of trienes also results in the almost quantitative formation of mono-hydrogenation products, the isolated dienes, from both ocimene and myrcene.