Isobutane, also known as ''i''-butane, 2-methylpropane or methylpropane, is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

with

molecular formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

HC(CH₃)₃. It is an

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...

butane Butane () or ''n''-butane is an alkane with the formula C4H10. Butane is a gas at room temperature and atmospheric pressure. Butane is a highly flammable, colorless, easily liquefied gas that quickly vaporizes at room temperature. The name but ...

. Isobutane is a colourless, odourless gas. It is the simplest

alkane In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which ...

with a

tertiary carbon Tertiary ( ) is a widely used but obsolete term for the geologic period from 66 million to 2.6 million years ago. The period began with the demise of the non-avian dinosaurs in the Cretaceous–Paleogene extinction event, at the star ...

atom. Isobutane is used as a precursor molecule in the

petrochemical industry The petrochemical industry is concerned with the production and trade of petrochemicals. A major part is constituted by the plastics (polymer) industry. It directly interfaces with the petroleum industry, especially the downstream sector. Compan ...

, for example in the synthesis of

isooctane 2,2,4-Trimethylpentane, also known as isooctane or iso-octane, is an organic compound with the formula (CH3)3CCH2CH(CH3)2. It is one of several isomers of octane (C8H18). This particular isomer is the standard 100 point on the octane rating sc ...

Production

Isobutane is obtained by

isomerization In chemistry, isomerization or isomerisation is the process in which a molecule, polyatomic ion or molecular fragment is transformed into an isomer with a different chemical structure. Enolization is an example of isomerization, as is tautomeriz ...

. :

Uses

Isobutane is the principal feedstock in

alkylation unit An alkylation unit (alky) is one of the conversion processes used in petroleum refineries. It is used to convert isobutane and low-molecular-weight alkenes (primarily a mixture of propene and butene) into alkylate, a high octane gasoline componen ...

s of refineries. Using isobutane, gasoline-grade "blendstocks" are generated with high branching for good combustion characteristics. Typical products created with isobutane are

2,4-dimethylpentane 2,4-Dimethylpentane is an alkane with the chemical formula H3C)2CHsub>2CH2. This colorless hydrocarbon is produced in large quantities in oil refineries. It results from the alkylation of isobutane by propylene Propylene, also known as prop ...

and especially

2,2,4-trimethylpentane 2,2,4-Trimethylpentane, also known as isooctane or iso-octane, is an organic compound with the formula (CH3)3CCH2CH(CH3)2. It is one of several isomers of octane (C8H18). This particular isomer is the standard 100 point on the octane rating scale ...

Solvent

In the Chevron Phillips slurry process for making

high-density polyethylene High-density polyethylene (HDPE) or polyethylene high-density (PEHD) is a thermoplastic polymer produced from the monomer ethylene. It is sometimes called "alkathene" or "polythene" when used for HDPE pipes. With a high strength-to-density ratio, ...

, isobutane is used as a diluent. As the slurried polyethylene is removed, isobutane is "flashed" off, and condensed, and recycled back into the loop reactor for this purpose.

Precursor to ''tert''-butyl hydroperoxide

Isobutane is oxidized to ''tert''-butyl hydroperoxide, which is subsequently reacted with

propylene Propylene, also known as propene, is an unsaturated organic compound with the chemical formula CH3CH=CH2. It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petrole ...

to yield

propylene oxide Propylene oxide is an acutely toxic and carcinogenic organic compound with the molecular formula CH3CHCH2O. This colourless volatile liquid with an odour similar to ether, is produced on a large scale industrially. Its major application is its us ...

. The

tert-butanol ''tert''-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as ''t''-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. ''tert''-Butyl alcohol is a colorless solid, which melts near roo ...

that results as a by-product is typically used to make gasoline additives such as

methyl tert-butyl ether Methyl ''tertiary''-butyl ether (MTBE), also known as methyl tert-butyl ether and ''tert''-butyl methyl ether, is an organic compound with a structural formula (CH3)3COCH3. MTBE is a volatile, flammable, and colorless liquid that is sparingly sol ...

(MTBE).

Miscellaneous uses

Isobutane is also used as a propellant for aerosol spray cans. Isobutane is used as part of blended fuels, especially common in fuel canisters used for

camping Camping is an outdoor activity involving overnight stays away from home, either without shelter or using basic shelter such as a tent, or a recreational vehicle. Typically, participants leave developed areas to spend time outdoors in more nat ...

Refrigerant

Isobutane is used as a

refrigerant A refrigerant is a working fluid used in the heat pump and refrigeration cycle, refrigeration cycle of air conditioning systems and heat pumps where in most cases they undergo a repeated phase transition from a liquid to a gas and back again. Ref ...

. Use in refrigerators started in 1993 when

Greenpeace Greenpeace is an independent global campaigning network, founded in Canada in 1971 by Irving Stowe and Dorothy Stowe, immigrant environmental activists from the United States. Greenpeace states its goal is to "ensure the ability of the Earth t ...

presented the Greenfreeze project with the former East German company . In this regard, blends of pure, dry "isobutane" (R-600a) (that is, isobutane mixtures) have negligible

ozone depletion potential The ozone depletion potential (ODP) of a chemical compound is the relative amount of degradation to the ozone layer it can cause, with trichlorofluoromethane (R-11 or CFC-11) being fixed at an ODP of 1.0. Chlorodifluoromethane (R-22), for exampl ...

and very low

global warming potential Global warming potential (GWP) is the heat absorbed by any greenhouse gas in the atmosphere, as a multiple of the heat that would be absorbed by the same mass of carbon dioxide (). GWP is 1 for . For other gases it depends on the gas and the time f ...

(having a value of 3.3 times the GWP of carbon dioxide) and can serve as a functional replacement for R-12, R-22 (both of these being commonly known by the trademark

Freon Freon ( ) is a registered trademark of the Chemours Company and generic descriptor for a number of halocarbon products. They are stable, nonflammable, low toxicity gases or liquids which have generally been used as refrigerants and as aerosol prop ...

R-134a 1,1,1,2-Tetrafluoroethane (also known as norflurane (INN), R-134a, Freon 134a, Forane 134a, Genetron 134a, Green Gas, Florasol 134a, Suva 134a, or HFC-134a) is a hydrofluorocarbon (HFC) and haloalkane refrigerant with thermodynamic properties ...

, and other

chlorofluorocarbon Chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) are fully or partly halogenated hydrocarbons that contain carbon (C), hydrogen (H), chlorine (Cl), and fluorine (F), produced as volatile derivatives of methane, ethane, and prop ...

hydrofluorocarbon Hydrofluorocarbons (HFCs) are man-made organic compounds that contain fluorine and hydrogen atoms, and are the most common type of organofluorine compounds. Most are gases at room temperature and pressure. They are frequently used in air condi ...

s in conventional stationary refrigeration and air conditioning systems. As a refrigerant, isobutane poses a fire and explosion risk in addition to the hazards associated with non-flammable CFC refrigerants. Substitution of this refrigerant for motor vehicle air conditioning systems not originally designed for isobutane is widely prohibited or discouraged. Vendors and advocates of hydrocarbon refrigerants argue against such bans on the grounds that there have been very few such incidents relative to the number of vehicle air conditioning systems filled with hydrocarbons.

Nomenclature

The traditional name isobutane was still retained in the 1993

IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...

recommendations, https://www.acdlabs.com/iupac/nomenclature/93/r93_679.htm but is no longer recommended according to the 2013 recommendations. Since the longest continuous chain in isobutane contains only three carbon atoms, the

preferred IUPAC name In chemical nomenclature, a preferred IUPAC name (PIN) is a unique name, assigned to a chemical substance and preferred among the possible names generated by IUPAC nomenclature. The "preferred IUPAC nomenclature" provides a set of rules for choo ...

is 2-methylpropane but the

locant In the nomenclature of organic chemistry, a locant is a term to indicate the position of a functional group or substituent within a molecule. Numeric locants The International Union of Pure and Applied Chemistry (IUPAC) recommends the use of n ...

(2-) is typically omitted in general nomenclature as redundant; C2 is the only position on a propane chain where a methyl substituent can be located without altering the main chain and forming the constitutional isomer ''n''-butane.

References

External links

International Chemical Safety Card 0901
{{Authority control Alkanes Butane E-number additives Propellants Refrigerants