2,2-Dimethylbutane

2,2-Dimethylbutane Basic information
Product Name:2,2-Dimethylbutane
Synonyms:(CH3)3CCH2CH3;2,2-dimethyl-butan;butane,2,2-dimethyl-;NEOBUTANE;2,2-DIMETHYLBUTANE, STANDARD FOR GC;2,2-dinethyl butane;neobutan;(4-Heptoxyphenyl)-(4-heptoxyphenyl)imino-oxidoazanium
CAS:75-83-2
MF:C6H14
MW:86.18
EINECS:200-906-8
Product Categories:Acyclic;Alkanes;Building Blocks;Chemical Synthesis;Organic Building Blocks;Organics
Mol File:75-83-2.mol
2,2-Dimethylbutane Structure
2,2-Dimethylbutane Chemical Properties
Melting point −100 °C(lit.)
Boiling point 50 °C(lit.)
density 0.649 g/mL at 25 °C(lit.)
vapor density 2.97 (vs air)
vapor pressure 5.35 psi ( 20 °C)
refractive index n20/D 1.369(lit.)
Fp <−30 °F
storage temp. Flammables area
solubility In methanol: 590 and 800 g/L at 5 and 10 °C, respectively. Miscible at higher temperatures (Kiser et al., 1961). Miscible with other aliphatic hydrocarbons, e.g., pentane, hexane, heptane, etc.
form Liquid
pka>14 (Schwarzenbach et al., 1993)
color Clear colorless to slightly yellow
explosive limit~7.7%
Odor Threshold20ppm
Water Solubility insoluble
BRN 1730736
Henry’s Law Constant1.69(atm?m3/mol) at 25 °C (Mackay and Shiu, 1981)
Exposure limitsACGIH TLV: TWA and STEL for all isomers except n-hexane are 500 and 1,000 ppm, respectively (adopted).
Stability:Stable, but may be moisture sensitive. Highly flammable. Incompatible with strong oxidizing agents.
CAS DataBase Reference75-83-2(CAS DataBase Reference)
NIST Chemistry ReferenceButane, 2,2-dimethyl-(75-83-2)
EPA Substance Registry System2,2-Dimethylbutane (75-83-2)
Safety Information
Hazard Codes F,Xn,N
Risk Statements 11-38-51/53-65-67
Safety Statements 9-16-29-33-61-62
RIDADR UN 1208 3/PG 2
WGK Germany 3
RTECS EJ9300000
Autoignition Temperature797 °F
HazardClass 3
PackingGroup II
HS Code 29011000
Hazardous Substances Data75-83-2(Hazardous Substances Data)
ToxicityReported as an impurity (0.2 wt %) in 99.0–99.7 wt % 2,3-dimethylbutane (Chevron Phillips, 2004).
MSDS Information
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2,2-DimethylbutaneEnglish
SigmaAldrichEnglish
ACROSEnglish
ALFAEnglish
2,2-Dimethylbutane Usage And Synthesis
Chemical Properties2,2-dimethylbutane is the chain isomeric form of hexane. It is a colorless and flammable liquid with a specific gravity of 0.6444. Insoluble in water, miscible with alcohol, ether, acetone, benzene and petroleum ether. The solubility is similar to that of hexane and 2-methylpentane.
Physical propertiesClear, colorless liquid with a mild petroleum-like odor. Liquid quickly evaporates and forms conbustible fumes. An odor threshold concentration of 20 ppmv was reported by Nagata and Takeuchi (1990).
Uses2,2-Dimethylbutane is an acyclic alkane. Its Research Octane Number (RON) has been reported to be 91.8. It is used to Component of high-octane motor and aviation fuels, intermediate for agricultural chemicals.
Preparation2,2-Dimethylbutane can be synthesised by the hydroisomerisation of 2,3-dimethylbutane using an acid catalyst.
By the thermal or catalytic union (alkylation) of ethylene and isobutane, both recovered from refinery gases.
Production Methods2,2-Dimethylbutane is produced from crude oil, natural liquid gases, and petroleum refining processes.
Application2,2-Dimethylbutane may be employed as probe to investigate the nature of possible active sites in supported metal catalysts.
Some of the reported applications of 2,2-dimethylbutane include:
Palladium-catalyzed radical oxidative alkoxycarbonylation to prepare various alkyl carboxylates.
Iridium-iron-catalyzed tandem dehydrogenation-isomerization-hydrosilylation to synthesize corresponding silane.
General DescriptionColorless liquid with an odor of gasoline. Less dense than water and insoluble in water. Hence floats on water. Irritating vapor. Flash point -54°F.
Air & Water ReactionsHighly flammable. Insoluble in water.
Reactivity Profile2,2-Dimethylbutane may be incompatible with strong oxidizing agents like nitric acid. Charring may occur followed by ignition of unreacted material and other nearby combustibles. In other settings, mostly unreactive. Not affected by aqueous solutions of acids, alkalis, most oxidizing agents, and most reducing agents. When heated sufficiently or when ignited in the presence of air, oxygen or strong oxidizing agents, burns exothermically to produce carbon dioxide and water.
HazardHighly flammable, dangerous fire and explosion risk, explosion limits 1.2–7%
Health HazardInhalation causes dizziness, nausea, and vomiting; concentrated vapor may cause unconsciousness and collapse. Contact with liquid causes irritation of eyes; repeated contact may produce irritation of skin. Ingestion causes irritation of stomach. Aspiration causes severe lung irritation, rapidly developing pulmonary edema, and central nervous system excitement followed by depression.
Safety ProfileProbably an irritant and narcotic in high concentration. A very dangerous fire and explosion hazard when exposed to heat or flame; can react vigorously with oxidzing materials. Keep away from heat or open flame. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.
Environmental fatePhotolytic. Reported photooxidation rate constants for the reaction of 2,2-dimethylbutane with OH radicals at 297, 299, and 300 K are 2.59 x 10-12, 6.16 x 10-12, and 2.59 x 10-12 cm3/molecule?sec, respectively (Atkinson, 1985, 1990).
Chemical/Physical. Complete combustion in air yields carbon dioxide and water vapor. 2,2- Dimethylbutane will not hydrolyze because it has no hydrolyzable functional group.
Purification MethodsDistil it azeotropically with MeOH, then wash it with water, dry (Na2SO4) it, and distil it. [Beilstein 1 IV 367.]
2,2-Dimethylbutane Preparation Products And Raw materials
Raw materialsCYCLOPROPANE,1-ETHYL-1-METHYL-–>Pentanal, 4,4-dimethyl-–>2-Methyl-2-butene
Preparation Products2,2-DIMETHYLPROPANE–>1H-2-Benzopyran–>CIS-1,3-PENTADIENE–>3,3-Dimethylpentane–>Hexane

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