2,2,4-Trimethylpentane Chemical Properties

Melting point:

-107 °C

Boiling point:

98-99 °C(lit.)

Density 

0.692 g/mL at 25 °C(lit.)

vapor density 

3.9 (vs air)

vapor pressure 

41 mm Hg ( 21 °C)

refractive index 

n20/D 1.391(lit.)

Flash point:

18 °F

storage temp. 

Store at +5°C to +30°C.

solubility 

water: insoluble

form 

Liquid

pka

>14 (Schwarzenbach et al., 1993)

Specific Gravity

0.692 (20/4℃)

color 

APHA: ≤10

Relative polarity

-0.4

Odor Threshold

0.11ppm

explosive limit

1%(V)

Water Solubility 

INSOLUBLE

FreezingPoint 

-107.52℃

λmax

λ: 205 nm Amax: 1.00
λ: 225 nm Amax: 0.10
λ: 254 nm Amax: 0.01

Merck 

14,5193

BRN 

1696876

Henry's Law Constant

3.23 at 25 °C (Mackay and Shiu, 1981)

Exposure limits

ACGIH TLV: TWA for all isomers 300 ppm (adopted).

Dielectric constant

2.1（Ambient）

Stability:

Stable. Highly flammable. Incompatible with oxidizing agents, reducing agents.

LogP

4.373 (est)

CAS DataBase Reference

540-84-1(CAS DataBase Reference)

NIST Chemistry Reference

Pentane, 2,2,4-trimethyl-(540-84-1)

EPA Substance Registry System

2,2,4-Trimethylpentane (540-84-1)

Safety Information

Hazard Codes 

F,Xn,N

Risk Statements 

11-38-50/53-65-67

Safety Statements 

9-16-29-33-60-61-62

RIDADR 

UN 1262 3/PG 2

WGK Germany 

1

RTECS 

SA3320000

Autoignition Temperature

745 °F

TSCA 

Yes

HS Code 

2901 10 00

HazardClass 

3

PackingGroup 

II

Hazardous Substances Data

540-84-1(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: > 2500 mg/kg

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,2,4-Trimethylpentane Usage And Synthesis

Description

Isooctane is a flammable liquid isomer of octane. It is best known for defining the octane number to rate the antiknock quality of gasoline, which is related to engine performance.
Since 1930, many chemical processes, such as alkylation and polymerization, have been developed to increase the production of branched compounds in refi nery operations. High octane numbers in gasoline are those associated with the alkenes (olefins) and aromatics, especially akyl benzene compounds. For example, 2-pentene has a RON of 154. Benzene itself has a RON of 98, but 1,3,5-trimethylbenzene has a RON of 170. The highest octane numbers in gasoline are associated with cyclic alkenes, but these account for only a minute fraction of gasoline.

Chemical Properties

2,2,4-Trimethylpentane (isooctane), C8H18, is a colorless liquid naturally found in crude petroleum and in small amounts in natural gas. It is released to the environment by the petroleum industries, by automotive exhausts and emissions, and from hazardous-waste sites, landfills, and emissions from wood combustion.

Physical properties

Octane is a colorless liquid with a gasoline-like odor. The odor threshold is 4 ppm and 48 ppm (New Jersey Fact Sheet). An odor threshold concentration of 670 ppbv was reported by Nagata and Takeuchi (1990).

Uses

In determining octane numbers of fuels; in spectrophotometric analysis; as solvent and thinner.

Uses

2,2,4-Trimethylpentane is used as a mobile phase in High Performance Liquid Chromatography and Liquid Chromatography coupled with Mass Spectrometry.

Uses

Isooctane is a petroleum product, producedby the refining of petroleum. It is used as thestandard in determining the octane numbersof fuels (its antiknock octane number is 100)and as a solvent in chemical analysis.

Production Methods

Isooctane is produced from the fractional distillation of petroleum fractions and naphthas. It is also produced from the alkylation of 2-methylpropene with isobutane.

Definition

ChEBI: 2,2,4-Trimethylpentane is an alkane that consists of pentane bearing two methyl substituents at position 2 and a single methyl substituent at position 4.

General Description

A clear colorless liquid with a petroleum-like odor. Flash point 10°F. Less dense than water and insoluble in water. Vapors are heavier than air.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Saturated aliphatic hydrocarbons, such as 2,2,4-Trimethylpentane, 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.

Hazard

Intermediate, azeotropic distillation entrainer.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Health Hazard

The acute toxicity of isooctane is very lowand is similar to n-octane. Exposure tohigh concentrations may produce irritationof respiratory tract. Exposure to 30,000 ppmfor an hour may be lethal to mice. There isno report of any other adverse effects fromexposure to isooctane.

Fire Hazard

Highly flammable liquid; flash point (closed cup) －12.2°C (10°F); autoignition temperature 418°C (784°F) (NFPA 1997); fireextinguishing agent: dry chemical, foam, or CO2; use a water spray to keep fire-exposed containers cool. Isooctane forms explosive mixtures with air within the range 1–4.6% by volume of air.

Flammability and Explosibility

Flammable

Safety Profile

Mutation data reported. High concentrations can cause narcosis. A very dangerous fire hazard when exposed to heat, flame, oxidmers. Can react vigorously with reducing materials. Explosive in the form of vapor when exposed to heat or flame. To fight fire, use CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALKANES.

Potential Exposure

Octane is used as a solvent; as a fuel; as an intermediate in organic synthesis; and in azeotropicdistillations.

Carcinogenicity

Male and female rats were initiated with 170 ppm N-ethyl-N-hydroxyethylnitrosamine for 2 weeks and subsequently exposed to isooctane for 61 weeks. An increase in atypical cell foci (a preneoplastic lesion) was observed in male but not female rats promoted with the high dose.

Source

Schauer et al. (1999) reported 2,2,4-trimethylpentane in a diesel-powered medium-duty truck exhaust at an emission rate of 1,240 μg/km.
A constituent in gasoline. Harley et al. (2000) analyzed the headspace vapors of three grades of unleaded gasoline where ethanol was added to replace methyl tert-butyl ether. The gasoline vapor concentrations of 2,2,4-trimethylpentane in the headspace were 2.7 wt % for regular grade, 2.8 wt % for mid-grade, and 3.3 wt % for premium grade.
California Phase II reformulated gasoline contained 2,2,4-trimethylpentane at a concentration of 34.6 g/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 8.20 and 1,080 mg/km, respectively (Schauer et al., 2002).

Environmental Fate

Surface Water. Mackay and Wolkoff (1973) estimated an evaporation half-life of 4.1 sec from a surface water body that is 25 °C and 1 m deep.
Photolytic. The following rate constants were reported for the reaction of 2,2,4-trimethylpentane and OH radicals in the atmosphere: 2.3 x 10^-12 cm³/molecule?sec at 300 K (Hendry and Kenley, 1979); 2.83 x 10^-12 cm³/molecule?sec at 298 K (Greiner, 1970); 3.73 x 10^-12 cm³/molecule?sec at 298–305 K (Darnall et al., 1978); 3.7 x 10^-12 cm³/molecule?sec (Atkinson et al., 1979); 3.90 x 10^-12 cm³/molecule?sec at 298 K (Atkinson, 1985). Based on a photooxidation rate constant of 3.68 x 10^-12 cm³/molecule?sec for the reaction of 2,2,4-trimethylpentane and OH radicals in summer sunlight, the lifetime is 16 h (Altshuller, 1991).
Products identified from the reaction of 2,2,4-trimethylpentane with OH radicals in the presence of nitric oxide included acetone, 2-methypropanal, 4-hydroxy-4-methyl-2-pentanone, and hydroxy nitrates (Tuazon et al., 2002).
Chemical/Physical. Complete combustion in air produces carbon dioxide and water vapor. 2,2,4-Trimethylpentane will not hydrolyze in water.

Shipping

UN1262 Octanes, Hazard Class: 3; Labels: 3-Flammable liquid.

Purification Methods

Distil isooctane from sodium, pass it through a column of silica gel or activated alumina (to remove traces of olefins), and again distilled from sodium. Extract repeatedly with conc H2SO4, then agitate it with aqueous KMnO4, wash it with water, dry (CaSO4) and distil it. Purify it also by azeotropic distillation with EtOH, which is subsequently washed out with water, and the trimethylpentane is dried and fractionally distilled. [Forziati et al. J Res Nat Bur Stand 36 126 1946.] [Beilstein 1 IV 439.]

Incompatibilities

Reacts with strong oxidizers, causing fire and explosion hazard. Attacks some forms of plastics, rubber and coatings.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an after burner and scrubber. All federal, state, and local environmental regulations must be observed.

2,2,4-Trimethylpentane(540-84-1)Related Product Information

• Cyclopentane
• Sodium pentanesulfonate
• 2-Methylbutane
• Pentane
• Bromocyclopentane
• 2,2-DIMETHYLPROPANE
• HEXANES
• Methylcyclopentane
• Hexane
• Isonicotinic acid
• Isoniazid
• 2-Ethylhexanol
• 2-Ethylhexanoic acid
• DECACHLOROBIPHENYL
• Toluene
• 2,2',4,4',5,5'-HEXACHLOROBIPHENYL
• Isooctanoic acid
• Phosphoric acid, isooctyl ester