Isopropyl alcohol (

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 ...

name propan-2-ol and also called isopropanol or 2-propanol) is a colorless,

flammable A combustible material is a material that can burn (i.e., sustain a flame) in air under certain conditions. A material is flammable if it ignites easily at ambient temperatures. In other words, a combustible material ignites with some effort ...

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with a pungent alcoholic

odor An odor (American English) or odour ( Commonwealth English; see spelling differences) is a smell or a scent caused by one or more volatilized chemical compounds generally found in low concentrations that humans and many animals can perceive ...

. Isopropyl alcohol, an organic

polar molecule In chemistry, polarity is a separation of electric charge leading to a molecule or its chemical groups having an electric dipole moment, with a negatively charged end and a positively charged end. Polar molecules must contain one or more polar ...

, is

miscible Miscibility () is the property of two substances to mix in all proportions (that is, to fully dissolve in each other at any concentration), forming a homogeneous mixture (a solution). Such substances are said to be miscible (etymologically ...

water Water is an inorganic compound with the chemical formula . It is a transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance. It is the main constituent of Earth's hydrosphere and the fluids of all known liv ...

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

, and

chloroform Chloroform, or trichloromethane (often abbreviated as TCM), is an organochloride with the formula and a common solvent. It is a volatile, colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to refrigerants and po ...

, demonstrating its ability to dissolve a wide range of substances including

ethyl cellulose Ethyl cellulose (or ethylcellulose) is a derivative of cellulose in which some of the hydroxyl groups on the repeating glucose units are converted into ethyl ether groups. The number of ethyl groups can vary depending on the manufacturer. It i ...

polyvinyl butyral Polyvinyl butyral (or PVB) is a resin mostly used for applications that require strong binding, optical clarity, adhesion to many surfaces, toughness and flexibility. It is prepared from polyvinyl alcohol by reaction with butyraldehyde. The m ...

, oils,

alkaloids Alkaloids are a broad class of naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large variety of organisms i ...

, and natural

resin A resin is a solid or highly viscous liquid that can be converted into a polymer. Resins may be biological or synthetic in origin, but are typically harvested from plants. Resins are mixtures of organic compounds, predominantly terpenes. Commo ...

s. Notably, it is not

with salt solutions and can be separated by adding

sodium chloride Sodium chloride , commonly known as Salt#Edible salt, edible salt, is an ionic compound with the chemical formula NaCl, representing a 1:1 ratio of sodium and chloride ions. It is transparent or translucent, brittle, hygroscopic, and occurs a ...

in a process known as

salting out Salting out (also known as salt-induced precipitation, salt fractionation, anti-solvent crystallization, precipitation crystallization, or drowning out) is a purification technique that utilizes the reduced solubility of certain molecules in a s ...

. It forms an

azeotrope An azeotrope () or a constant heating point mixture is a mixture of two or more liquids whose proportions cannot be changed by simple distillation.Moore, Walter J. ''Physical Chemistry'', 3rd e Prentice-Hall 1962, pp. 140–142 This happens beca ...

with water, resulting in a

boiling point The boiling point of a substance is the temperature at which the vapor pressure of a liquid equals the pressure surrounding the liquid and the liquid changes into a vapor. The boiling point of a liquid varies depending upon the surrounding envi ...

of 80.37 °C and is characterized by its slightly bitter taste. Isopropyl alcohol becomes

viscous Viscosity is a measure of a fluid's rate-dependent resistance to a change in shape or to movement of its neighboring portions relative to one another. For liquids, it corresponds to the informal concept of ''thickness''; for example, syrup h ...

at lower temperatures, freezing at −89.5 °C, and has significant

ultraviolet Ultraviolet radiation, also known as simply UV, is electromagnetic radiation of wavelengths of 10–400 nanometers, shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight and constitutes about 10% of ...

-visible absorbance at 205 nm. Chemically, it can be oxidized to

acetone Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...

or undergo various reactions to form compounds like isopropoxides or aluminium isopropoxide. As an

isopropyl In organic chemistry, a propyl group is a three-carbon alkyl substituent with chemical formula for the linear form. This substituent form is obtained by removing one hydrogen atom attached to the terminal carbon of propane. A propyl substituent ...

group linked to a

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

group (

chemical formula 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, such as pare ...

) it is the simplest example of a

secondary alcohol In chemistry, an alcohol (), is a type of organic compound that carries at least one hydroxyl () functional group bound to a Saturated and unsaturated compounds, saturated carbon atom. Alcohols range from the simple, like methanol and ethanol ...

, where the

alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...

carbon atom is attached to two other carbon atoms. It is a

structural isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

of propan-1-ol and ethyl methyl ether, all of which share the formula . It was first synthesized in 1853 by

Alexander William Williamson Alexander William Williamson Fellow of the Royal Society, FRS FRSE Chemical Society, PCS MRIA (1 May 18246 May 1904) was an English chemist. He is best known today for the Williamson ether synthesis. Life Williamson was born in 1824 in Wands ...

and later produced for

cordite Cordite is a family of smokeless propellants developed and produced in Britain since 1889 to replace black powder as a military firearm propellant. Like modern gunpowder, cordite is classified as a low explosive because of its slow burni ...

preparation. It is produced through hydration of

propene Propylene, also known as propene, is an unsaturated organic compound with the chemical formula . 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 petroleum-like od ...

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...

of acetone, with modern processes achieving anhydrous alcohol through

azeotropic distillation In chemistry, azeotropic distillation is any of a range of techniques used to break an azeotrope in distillation. In chemical engineering, ''azeotropic distillation'' usually refers to the specific technique of adding another component to genera ...

. Beyond its production, isopropyl alcohol serves in medical settings as a

rubbing alcohol Rubbing alcohol, known as surgical spirit in the British Pharmacopoeia, refers to a group of denatured alcohol solutions commonly used as topical disinfectant. In addition to its medical applications, rubbing alcohol is employed in various indust ...

and

hand sanitizer Hand sanitizer (also known as hand antiseptic, hand disinfectant, hand rub, or handrub) is a liquid, gel, or foam used to kill viruses, bacteria, and other microorganisms on the hands. It can also come in the form of a cream, spray, or wipe. W ...

, and in industrial and household applications as a solvent. It is a common ingredient in products such as

antiseptic An antiseptic ( and ) is an antimicrobial substance or compound that is applied to living tissue to reduce the possibility of sepsis, infection, or putrefaction. Antiseptics are generally distinguished from ''antibiotics'' by the latter's abil ...

disinfectant A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than ...

s and

detergent A detergent is a surfactant or a mixture of surfactants with Cleanliness, cleansing properties when in Concentration, dilute Solution (chemistry), solutions. There are a large variety of detergents. A common family is the alkylbenzene sulfonate ...

s. More than a million tonnes are produced worldwide annually. Despite its utility, isopropyl alcohol poses safety risks due to its flammability and potential for

peroxide In chemistry, peroxides are a group of Chemical compound, compounds with the structure , where the R's represent a radical (a portion of a complete molecule; not necessarily a free radical) and O's are single oxygen atoms. Oxygen atoms are joined ...

formation. Its ingestion or absorption leads to

toxic Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst ...

effects including

central nervous system depression Central nervous system depression (or CNS depression) is a nervous system disorder characterized by a severely impaired physiological state in which patients may exhibit decreased rate of breathing, decreased heart rate, and loss of consciousnes ...

and

coma A coma is a deep state of prolonged unconsciousness in which a person cannot be awakened, fails to Nociception, respond normally to Pain, painful stimuli, light, or sound, lacks a normal Circadian rhythm, sleep-wake cycle and does not initiate ...

, primarily treated through supportive measures.

Properties

Isopropyl alcohol is

in water,

, and

, as it is an organic

. It dissolves

, many oils, alkaloids, and natural resins. Unlike

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

, isopropyl alcohol is not miscible with salt solutions and can be separated from

aqueous solution An aqueous solution is a solution in which the solvent is water. It is mostly shown in chemical equations by appending (aq) to the relevant chemical formula. For example, a solution of table salt, also known as sodium chloride (NaCl), in water ...

s by adding a salt such as

. The process is colloquially called ''

'', and causes concentrated isopropyl alcohol to separate into a distinct layer. Isopropyl alcohol forms an

with water, which gives a boiling point of and a composition of 87.7% by mass (91% by volume) isopropyl alcohol. It has a slightly bitter taste, and is not safe to drink. Isopropyl alcohol becomes increasingly viscous with decreasing temperature and freezes at . Mixtures with water have higher freezing points: 99% at , 91% (the azeotrope) at , and 70% at . Isopropyl alcohol has a maximal

absorbance Absorbance is defined as "the logarithm of the ratio of incident to transmitted radiant power through a sample (excluding the effects on cell walls)". Alternatively, for samples which scatter light, absorbance may be defined as "the negative log ...

at 205 nm in an

- visible spectrum.

Reactions

Isopropyl alcohol can be

oxidized Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...

, which is the corresponding

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

. This can be achieved using oxidizing agents such as

chromic acid Chromic acid is a chemical compound with the chemical formula . It is also a jargon for a solution formed by the addition of sulfuric acid to aqueous solutions of dichromate. It consists at least in part of chromium trioxide. The term "chromic ...

, or by

dehydrogenation In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At ...

of isopropyl alcohol over a heated copper

catalyst Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...

: Isopropyl alcohol is often used as both solvent and

hydride In chemistry, a hydride is formally the anion of hydrogen (H−), a hydrogen ion with two electrons. In modern usage, this is typically only used for ionic bonds, but it is sometimes (and has been more frequently in the past) applied to all che ...

source in the Meerwein-Ponndorf-Verley reduction and other

transfer hydrogenation In chemistry, transfer hydrogenation is a chemical reaction involving the addition of hydrogen to a compound from a source other than molecular . It is applied in laboratory and industrial organic synthesis to saturate organic compounds and re ...

reactions. Isopropyl alcohol may be converted to 2-bromopropane using

phosphorus tribromide Phosphorus tribromide is a colourless liquid with the formula P Br3. The liquid fumes in moist air due to hydrolysis and has a penetrating odour. It is used in the laboratory for the conversion of alcohols to alkyl bromides. Preparation PBr3 ...

, or dehydrated to

by heating with

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...

. Like most alcohols, isopropyl alcohol reacts with active

metal A metal () is a material that, when polished or fractured, shows a lustrous appearance, and conducts electrical resistivity and conductivity, electricity and thermal conductivity, heat relatively well. These properties are all associated wit ...

s such as

potassium Potassium is a chemical element; it has Symbol (chemistry), symbol K (from Neo-Latin ) and atomic number19. It is a silvery white metal that is soft enough to easily cut with a knife. Potassium metal reacts rapidly with atmospheric oxygen to ...

to form

alkoxide In chemistry, an alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They are written as , where R is the organyl substituent. Alkoxides are strong bases and, whe ...

s that are called isopropoxides. With

titanium tetrachloride Titanium tetrachloride is the inorganic compound with the formula . It is an important intermediate in the production of titanium metal and the pigment titanium dioxide. is a volatile liquid. Upon contact with humid air, it forms thick clouds o ...

, isopropyl alcohol reacts to give

titanium isopropoxide Titanium isopropoxide, also commonly referred to as titanium tetraisopropoxide or TTIP, is a chemical compound with the formula . This alkoxide of titanium(IV) is used in organic synthesis and materials science. It is a diamagnetic tetrahedral mol ...

: This and similar reactions are often conducted in the presence of base. The reaction with

aluminium Aluminium (or aluminum in North American English) is a chemical element; it has chemical symbol, symbol Al and atomic number 13. It has a density lower than that of other common metals, about one-third that of steel. Aluminium has ...

is initiated by a trace of mercury to give aluminium isopropoxide.

History

Isopropyl alcohol was first synthesized by the chemist

in 1853. He achieved this by heating a mixture of propene and sulfuric acid.

Standard Oil Standard Oil Company was a Trust (business), corporate trust in the petroleum industry that existed from 1882 to 1911. The origins of the trust lay in the operations of the Standard Oil of Ohio, Standard Oil Company (Ohio), which had been founde ...

produced isopropyl alcohol by hydrating

. Isopropyl alcohol was oxidized to

for the preparation of

, a smokeless,

low explosive An explosive (or explosive material) is a reactive substance that contains a great amount of potential energy that can produce an explosion if released suddenly, usually accompanied by the production of light, heat, sound, and pressure. An exp ...

propellant.

Production

In 1994, 1.5 million tonnes of isopropyl alcohol were produced in the United States, Europe, and Japan. It is primarily produced by combining water and

in a

hydration reaction In chemistry, a hydration reaction is a chemical reaction in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed indust ...

or by hydrogenating

. There are two routes for the hydration process and both processes require that the isopropyl alcohol be separated from water and other by-products by

distillation Distillation, also classical distillation, is the process of separating the component substances of a liquid mixture of two or more chemically discrete substances; the separation process is realized by way of the selective boiling of the mixt ...

. Isopropyl alcohol and water form an

, and simple distillation gives a material that is 87.9% by mass isopropyl alcohol and 12.1% by mass water. Pure (

anhydrous A substance is anhydrous if it contains no water. Many processes in chemistry can be impeded by the presence of water; therefore, it is important that water-free reagents and techniques are used. In practice, however, it is very difficult to achie ...

) isopropyl alcohol is made by

of the wet isopropyl alcohol using either

diisopropyl ether Diisopropyl ether is a secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is used as an extractant and an oxygenate gasoline additive. It is obtained i ...

cyclohexane Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexan ...

as azeotroping agents.

Biological

Small amounts of isopropyl alcohol are produced in the body in

diabetic ketoacidosis Diabetic ketoacidosis (DKA) is a potentially life-threatening acute complication of diabetes mellitus. Signs and symptoms may include vomiting, abdominal pain, deep gasping breathing, increased urination, weakness, confusion and occasionally ...

Indirect hydration

Indirect hydration reacts propene with

to form a mixture of sulfate esters. This process can use low-quality propene, and is predominant in the USA. These processes give primarily isopropyl alcohol rather than 1-propanol, because adding water or sulfuric acid to propene follows

Markovnikov's rule In organic chemistry, Markovnikov's rule or Markownikoff's rule describes the outcome of some addition reactions. The rule was formulated by Russian chemist Vladimir Markovnikov in 1870. Explanation The rule states that with the addition of a ...

. Subsequent

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

of these esters by steam produces isopropyl alcohol, by distillation.

Diisopropyl ether Diisopropyl ether is a secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is used as an extractant and an oxygenate gasoline additive. It is obtained i ...

is a significant by-product of this process; it is recycled back to the process and hydrolyzed to give the desired product.

Direct hydration

Direct hydration reacts propene and water, either in gas or liquid

phase Phase or phases may refer to: Science *State of matter, or phase, one of the distinct forms in which matter can exist *Phase (matter), a region of space throughout which all physical properties are essentially uniform *Phase space, a mathematica ...

, at high pressures in the presence of solid or supported acidic

s. This type of process usually requires higher-purity

propylene Propylene, also known as propene, is an unsaturated organic compound with the chemical formula . 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 petroleum-like o ...

(> 90%). Direct hydration is more commonly used in Europe.

Hydrogenation of acetone

Isopropyl alcohol can be prepared via the

, but this approach involves an extra step compared to the above methods, as acetone is itself normally prepared from propene via the

cumene process The cumene process (cumene-phenol process, Hock process) is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene (isopropyl benzene), the intermediate material during the process. It ...

. cost is primarily driven by raw material cost, and this way is economical when acetone is cheaper than propylene as a

byproduct A by-product or byproduct is a secondary product derived from a production process, manufacturing process or chemical reaction; it is not the primary product or service being produced. A by-product can be useful and marketable or it can be cons ...

phenol Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () ...

production (the coexistence of two ways on most markets allows them to balance the prices). A known issue is the formation of MIBK and other self-condensation products.

Raney nickel Raney nickel , also called spongy nickel, is a fine-grained solid composed mostly of nickel derived from a nickel–aluminium alloy. Several grades are known, of which most are gray solids. Some are pyrophoric, but most are used as air-stable s ...

was one of the original industrial catalysts, modern catalysts are often supported bimetallic materials.

Uses

In 1990, 45,000 metric tonnes of isopropyl alcohol were used in the United States, mostly as a solvent for coatings or for industrial processes. In that year, 5400 metric tonnes were used for household purposes and in personal care products. Isopropyl alcohol is popular in particular for pharmaceutical applications, due to its low toxicity. Some isopropyl alcohol is used as a chemical intermediate. Isopropyl alcohol may be converted to acetone, but the

is more significant.

Solvent

Isopropyl alcohol dissolves a wide range of

non-polar In chemistry, polarity is a separation of electric charge leading to a molecule or its chemical groups having an electric dipole moment, with a negatively charged end and a positively charged end. Polar molecules must contain one or more polar ...

compounds. It evaporates quickly and the typically available grades tend to not leave behind oil traces when used as a cleaning fluid unlike some other common solvents. It is also relatively non-toxic. Thus, it is used widely as a solvent and as a cleaning fluid, especially where there are oils or oil based residues which are not easily cleaned with water, conveniently evaporating and (depending on water content and other variables) posing less of a risk of corrosion or rusting than plain water. Together with

, ''n''-butanol, and

, it belongs to the group of alcohol solvents. Isopropyl alcohol is commonly used for cleaning

eyeglasses Glasses, also known as eyeglasses (American English), spectacles (Commonwealth English), or colloquially as specs, are Visual perception, vision eyewear with clear or tinted lens (optics), lenses mounted in a frame that holds them in front ...

electrical contact An electrical contact is an Electronic component, electrical circuit component found in electrical switches, relays, Electrical connector, connectors and circuit breakers. Each contact is a piece of electrically conductive material, typically meta ...

s, audio or video

tape head ''Tape Head'' is the seventh studio album by American rock band King's X, released in 1998 via Metal Blade Records. A music video was made for the song "Fade". "World" is a reworked song from the band's ''Sneak Preview'' demos. The controv ...

s, DVD and other

optical disc An optical disc is a flat, usuallyNon-circular optical discs exist for fashion purposes; see shaped compact disc. disc-shaped object that stores information in the form of physical variations on its surface that can be read with the aid o ...

lenses,

bong A bong (also known as a water pipe) is a filtration device generally used for smoking cannabis, tobacco, or other herbal substances. In the bong shown in the photo, the smoke flows from the lower port on the left to the upper port on the right ...

s, and for removing

thermal paste Thermal paste (also called thermal compound, thermal grease, thermal interface material (TIM), thermal gel, heat paste, heat sink compound, heat sink paste or CPU grease) is a thermally conductive (but usually not electrically conductive) ch ...

from

heatsink A heat sink (also commonly spelled heatsink) is a passive heat exchanger that transfers the heat generated by an electronic or a mechanical device to a fluid medium, often air or a liquid coolant, where it is dissipated away from the device, ...

s on

CPU A central processing unit (CPU), also called a central processor, main processor, or just processor, is the primary processor in a given computer. Its electronic circuitry executes instructions of a computer program, such as arithmetic, log ...

s and other IC packages. It is sometimes used by miniatures hobbyists to strip acrylic paints & primers from

high impact polystyrene In polymer chemistry, graft polymers are segmented copolymers with a linear backbone of one composite and randomly distributed branches of another composite. The picture labeled "graft polymer" shows how grafted chains of species B are coval ...

miniatures.

Intermediate

Isopropyl alcohol is

esterified In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distinct ...

to give isopropyl acetate, another solvent. It reacts with

carbon disulfide Carbon disulfide (also spelled as carbon disulphide) is an inorganic compound with the chemical formula and structure . It is also considered as the anhydride of thiocarbonic acid. It is a colorless, flammable, neurotoxic liquid that is used as ...

and

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...

to give sodium isopropylxanthate, which has use as an

herbicide Herbicides (, ), also commonly known as weed killers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page f ...

and an ore flotation reagent. Isopropyl alcohol reacts with

and

metal to give

titanium Titanium is a chemical element; it has symbol Ti and atomic number 22. Found in nature only as an oxide, it can be reduced to produce a lustrous transition metal with a silver color, low density, and high strength, resistant to corrosion in ...

and aluminium isopropoxides, respectively, the former a catalyst, and the latter a chemical reagent. This compound may serve as a chemical reagent in itself, by acting as a dihydrogen donor in

Medical

Rubbing alcohol Rubbing alcohol, known as surgical spirit in the British Pharmacopoeia, refers to a group of denatured alcohol solutions commonly used as topical disinfectant. In addition to its medical applications, rubbing alcohol is employed in various indust ...

, and disinfecting pads typically contain a 60–70%

solution Solution may refer to: * Solution (chemistry), a mixture where one substance is dissolved in another * Solution (equation), in mathematics ** Numerical solution, in numerical analysis, approximate solutions within specified error bounds * Solu ...

of isopropyl alcohol or

. Water is required to open up membrane pores of bacteria, which acts as a gateway for isopropyl alcohol. A 75% solution in water may be used as a hand sanitizer. Isopropyl alcohol is used as a water-drying aid for the prevention of

otitis externa Otitis externa, also called swimmer's ear, is inflammation of the ear canal. It often presents with ear pain, swelling of the ear canal, and occasionally decreased hearing. Typically there is pain with movement of the outer ear. A high fever ...

, better known as swimmer's ear. Inhaled isopropyl alcohol can be used for treating nausea in some settings by placing a disinfecting pad under the nose.

Early uses as an anesthetic

Although isopropyl alcohol can be used for anesthesia, its many negative attributes or drawbacks prohibit this use. Isopropyl alcohol can also be used similarly to ether as a solvent or as an anesthetic by inhaling the fumes or orally. Early uses included using the solvent as general anesthetic for small mammals and rodents by scientists and some veterinarians. However, it was soon discontinued, as many complications arose, including respiratory irritation, internal bleeding, and visual and hearing problems. In rare cases, respiratory failure leading to death in animals was observed.

Automotive

Isopropyl alcohol is a major ingredient in "gas dryer"

fuel additive Gasoline additives may increase gasoline's octane rating, thus allowing the use of higher compression ratios for greater efficiency and power, or act as corrosion inhibitors or lubricants. Other additives include metal deactivators, oxygenates an ...

s. In significant quantities,

is a problem in fuel tanks, as it separates from gasoline and can freeze in the supply lines at low temperatures. Alcohol does not remove water from gasoline, but the alcohol solubilizes water in gasoline. Once

soluble In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution. The extent of the solubi ...

, water does not pose the same risk as insoluble water, as it no longer accumulates in the supply lines and freezes but is dissolved within the fuel itself. Isopropyl alcohol is often sold in aerosol cans as a

windshield The windshield (American English and Canadian English) or windscreen (Commonwealth English) of an aircraft, car, bus, motorbike, truck, train, boat or streetcar is the front window, which provides visibility while protecting occupants from t ...

or door lock deicer. Isopropyl alcohol is also used to remove

brake fluid Brake fluid is a type of hydraulic fluid used in hydraulic brake and hydraulic clutch applications in automobiles, motorcycles, light trucks, and some bicycles. It is used to transfer force into pressure, and to amplify braking force. It wo ...

traces from hydraulic braking systems, so that the brake fluid (usually DOT 3, DOT 4, or

mineral oil Mineral oil is any of various colorless, odorless, light mixtures of higher alkanes from a mineral source, particularly a distillate of petroleum, as distinct from usually edible vegetable oils. The name 'mineral oil' by itself is imprecise, ...

) does not contaminate the

brake pads Brake pads are a component of disc brakes used in automotive and other applications. Brake pads are composed of steel backing plates with friction material bound to the surface that faces the disc brake rotors. Function Brake pads convert the ki ...

and cause poor braking. Mixtures of isopropyl alcohol and water are also commonly used in homemade windshield washer fluid.

Laboratory

As a biological specimen preservative, isopropyl alcohol provides a comparatively non-toxic alternative to

formaldehyde Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...

and other synthetic preservatives. Isopropyl alcohol solutions of 70–99% are used to preserve specimens. Isopropyl alcohol is often used in

DNA extraction The first isolation of deoxyribonucleic acid (DNA) was done in 1869 by Friedrich Miescher. DNA extraction is the process of isolating DNA from the cells of an organism isolated from a sample, typically a biological sample such as blood, saliva, ...

. A lab worker adds it to a DNA solution to precipitate the DNA, which then forms a pellet after centrifugation. This is possible because DNA is insoluble in isopropyl alcohol.

Semiconductors

Isopropyl alcohol is used as an additive in alkaline anisotropic etching of

monocrystalline silicon Monocrystalline silicon, often referred to as single-crystal silicon or simply mono-Si, is a critical material widely used in modern electronics and photovoltaics. As the foundation for silicon-based discrete components and integrated circuits, ...

, such as with

potassium hydroxide Potassium hydroxide is an inorganic compound with the formula K OH, and is commonly called caustic potash. Along with sodium hydroxide (NaOH), KOH is a prototypical strong base. It has many industrial and niche applications, most of which utili ...

tetramethylammonium hydroxide Tetramethylammonium hydroxide (TMAH or TMAOH) is a quaternary ammonium salt with molecular formula N(CH3)4+ OH−. It is commonly encountered in form of concentrated solutions in water or methanol. TMAH in solid state and its aqueous soluti ...

. This process is used in texturing of

silicon solar cells Silicon is a chemical element; it has symbol Si and atomic number 14. It is a hard, brittle crystalline solid with a blue-grey metallic lustre, and is a tetravalent metalloid (sometimes considered a non-metal) and semiconductor. It is a member ...

and microfabrication (e.g. in

MEMS MEMS (micro-electromechanical systems) is the technology of microscopic devices incorporating both electronic and moving parts. MEMS are made up of components between 1 and 100 micrometres in size (i.e., 0.001 to 0.1 mm), and MEMS devices ...

devices). Isopropyl alcohol increases the anisotropy of the etch by increasing the etch rate of 00plane relative to higher indexed planes.

Safety

Isopropyl alcohol vapor is denser than air and is

, with a flammability range of between 2% and 12.7% in air. It should be kept away from heat, sparks, and open flame. Distillation of isopropyl alcohol over magnesium has been reported to form

peroxides In chemistry, peroxides are a group of compounds with the structure , where the R's represent a radical (a portion of a complete molecule; not necessarily a free radical) and O's are single oxygen atoms. Oxygen atoms are joined to each other and ...

, which may explode upon concentration. Isopropyl alcohol can react with air and oxygen over time to form unstable peroxides that can explode.

Toxicology

Isopropyl alcohol, via its metabolites, is somewhat more toxic than ethanol, but considerably less toxic than

ethylene glycol Ethylene glycol ( IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula . It is mainly used for two purposes: as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odo ...

. Death from ingestion or absorption of even relatively large quantities is rare. Both isopropyl alcohol and its

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

, act as

central nervous system The central nervous system (CNS) is the part of the nervous system consisting primarily of the brain, spinal cord and retina. The CNS is so named because the brain integrates the received information and coordinates and influences the activity o ...

(CNS)

depressant Depressants, also known as central nervous system depressants, or colloquially known as "downers", are drugs that lower neurotransmission levels, decrease the electrical activity of brain cells, or reduce arousal or stimulation in various ...

s. Poisoning can occur from ingestion, inhalation, or skin absorption.

Symptom Signs and symptoms are diagnostic indications of an illness, injury, or condition. Signs are objective and externally observable; symptoms are a person's reported subjective experiences. A sign for example may be a higher or lower temperature ...

s of isopropyl alcohol poisoning include flushing,

headache A headache, also known as cephalalgia, is the symptom of pain in the face, head, or neck. It can occur as a migraine, tension-type headache, or cluster headache. There is an increased risk of Depression (mood), depression in those with severe ...

dizziness Dizziness is an imprecise term that can refer to a sense of disorientation in space, vertigo, or lightheadedness. It can also refer to Balance disorder, disequilibrium or a non-specific feeling, such as giddiness or foolishness. Dizziness is a ...

, CNS depression,

nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. It can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the throat. Over 30 d ...

vomiting Vomiting (also known as emesis, puking and throwing up) is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose. Vomiting can be the result of ailments like food poisoning, gastroenteritis, pre ...

anesthesia Anesthesia (American English) or anaesthesia (British English) is a state of controlled, temporary loss of sensation or awareness that is induced for medical or veterinary purposes. It may include some or all of analgesia (relief from or prev ...

hypothermia Hypothermia is defined as a body core temperature below in humans. Symptoms depend on the temperature. In mild hypothermia, there is shivering and mental confusion. In moderate hypothermia, shivering stops and confusion increases. In severe ...

low blood pressure Hypotension, also known as low blood pressure, is a cardiovascular condition characterized by abnormally reduced blood pressure. Blood pressure is the force of blood pushing against the walls of the arteries as the heart pumps out blood and is ...

shock Shock may refer to: Common uses Healthcare * Acute stress reaction, also known as psychological or mental shock ** Shell shock, soldiers' reaction to battle trauma * Circulatory shock, a medical emergency ** Cardiogenic shock, resulting from ...

respiratory depression Hypoventilation (also known as respiratory depression) occurs when ventilation is inadequate (''hypo'' meaning "below") to perform needed respiratory gas exchange. By definition it causes an increased concentration of carbon dioxide (hypercapni ...

, and

. Overdoses may cause a fruity odor on the breath as a result of its metabolism to

. Isopropyl alcohol does not cause an anion gap acidosis, but it produces an osmolal gap between the calculated and measured osmolalities of serum, as do the other alcohols. The findings of

without acidosis leads to the

sine qua non A ''sine qua non'' (, ) or ''condicio sine qua non'' (plural: ''condiciones sine quibus non'') is an indispensable and essential action, condition, or ingredient. It was originally a Latin legal term for " conditionwithout which it could not b ...

of "ketosis without acidosis." Isopropyl alcohol is oxidized to form acetone by

alcohol dehydrogenase Alcohol dehydrogenases (ADH) () are a group of dehydrogenase enzymes that occur in many organisms and facilitate the interconversion between alcohols and aldehydes or ketones with the reduction of nicotinamide adenine dinucleotide (NAD+) to N ...

in the liver and has a

biological half-life Biological half-life (elimination half-life, pharmacological half-life) is the time taken for concentration of a drug, biological substance (such as a medication) to decrease from its maximum concentration (chemistry), concentration (Cmax (pharm ...

in humans between 2.5 and 8.0 hours. Unlike

poisoning, the metabolites of isopropyl alcohol are considerably less toxic, and treatment is largely supportive. Furthermore, there is no indication for the use of

fomepizole Fomepizole, also known as 4-methylpyrazole, is a medication used to treat methanol and ethylene glycol poisoning. It may be used alone or together with hemodialysis. It is given by injection into a vein. Common side effects include headache ...

, an alcohol dehydrogenase inhibitor, unless co-ingestion with methanol or ethylene glycol is suspected. In

forensic pathology Forensic pathology is pathology that focuses on determining the cause of death by examining a corpse. A post mortem examination is performed by a medical examiner or forensic pathologist, usually during the investigation of criminal law cases ...

, people who have died as a result of

alcoholic ketoacidosis Alcoholic ketoacidosis (AKA) is a specific group of symptoms and metabolic state related to alcohol use. Symptoms often include abdominal pain, vomiting, agitation, a fast respiratory rate, and a specific "fruity" smell. Consciousness is generall ...

, with no isopropyl alcohol ingestion, usually have detectable blood concentrations of isopropyl alcohol of 1 to 40 mg/dL, while those by fatal isopropyl alcohol ingestion usually have blood concentrations of hundreds of mg/dL.

References

External links

CDC – NIOSH Pocket Guide to Chemical Hazards - Isopropyl alcohol
* Environmental Health Criteria 103
2-Propanol
{{GABAAR PAMs Alcohol solvents Oxygenates Antiseptics Disinfectants Secondary alcohols GABAA receptor positive allosteric modulators Alkanols Isopropyl compounds Household chemicals Nerve agent precursors