Isopropyl alcohol

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Isopropyl alcohol

Isopropyl alcohol (also propan-2-ol, 2-propanol, iso, isopro, isoprop, rubbing alcohol
Rubbing alcohol

Rubbing alcohol, United States Pharmacopeia / British Pharmacopoeia is a liquid prepared and used primarily for topical application. It is prepared from a special denatured alcohol solution and contains 97.5-100% by volume of pure, concentrated ethanol ....
, or the abbreviation IPA) is a common name for isopropanol, a colorless, flammable chemical compound

Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
with a strong odor

Odor

An odor or odour is a volatilized chemical compound, generally at a very low concentration, that humans or other animals perceive by the sense of olfaction....
. It has the molecular formula C₃H₇OH and is the simplest example of a secondary alcohol

Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
, where the alcohol

Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
carbon is attached to two other carbons. It is an isomer

Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
of propanol

Propan-1-ol

Propan-1-ol is a primary alcohol with the formula CH3CH2CH2OH. It is also known as 1-propanol, 1-propyl alcohol, n-propyl alcohol, or simply propanol....
.

Production
Isopropyl alcohol is produced by combining water and propene.

Discussion

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Production

Isopropyl alcohol is produced by combining water and propene. There are two processes for achieving this: indirect hydration

Hydration reaction

In organic chemistry, a hydration reaction is a chemical reaction in which a hydroxyl group and a hydrogen cation are added to the two carbon atoms covalent bonded together in the carbon-carbon double bond which makes up an alkene functional group....
via the sulfuric acid process and direct hydration. The former process, which can use low-quality propylene, predominates in the USA while the latter process, which requires high-purity propylene, is more commonly used in Europe. These processes give predominantly isopropyl alcohol rather than 1-propanol because the addition of water or sulfuric acid

Sulfuric acid

Sulfuric acid, hydrogen2sulfuroxygen4, is a strong mineral acid. It is soluble in water at all concentrations. Sulfuric acid has many applications, and is one of the top products of the chemical industry....
to propylene follows Markovnikov's rule

Markovnikov's rule

In organic chemistry, Markovnikov's rule or Markownikoff's rule is an observation based on Zaitsev's rule. It was formulated by the Russian chemist Vladimir Vasilevich Markovnikov in 1870 ....
.

The indirect process reacts propylene with sulfuric acid to form a mixture of sulfate esters. Subsequent hydrolysis

Hydrolysis

Hydrolysis is a chemical reaction during which one or more water are split into hydrogen and hydroxide ions which may go on to participate in further reactions....
of these esters produces isopropyl alcohol. Direct hydration reacts propylene and water, either in gas or liquid phases, at high pressures in the presence of solid or supported acidic catalysts. Both processes require that the isopropyl alcohol be separated from water and other by-products by distillation

Distillation

Distillation is a method of separation process mixtures based on differences in their Volatility in a boiling liquid mixture. Distillation is a unit operation, or a physical separation process, and not a chemical reaction....
. Isopropyl alcohol and water form an azeotrope

Azeotrope

An azeotrope is a mixture of two or more liquids in such a ratio that its composition cannot be changed by simple distillation. This occurs because, when an azeotrope is boiled, the resulting vapor has the same ratio of constituents as the original mixture....
and simple distillation gives a material which is 87.9% by weight isopropyl alcohol and 12.1% by weight water. Pure (anhydrous) isopropyl alcohol is made by azeotropic distillation

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 generate a new lower-boiling azeotrope that is heterogeneous, such as the example below with the additio...
of the "wet" isopropyl alcohol using either diisopropyl ether

Diisopropyl ether

Diisopropyl ether is secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with most organic solvents....
or cyclohexane

Cyclohexane

Cyclohexane is a cycloalkane with the molecular formula Carbon6Hydrogen12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which are intermediates used in the production of nylon....
as azeotroping agents.

Uses

Isopropyl alcohol is cheaply available. Like acetone

Acetone

Acetone is the organic compound with the chemical formula OC2. This colorless, mobile, flammable liquid is the simplest example of the ketones....
, it dissolves a wide range of nonpolar compounds. It is also relatively nontoxic and dries quickly. Thus it is used widely as a solvent and as a cleaning fluid (by dissolving lipophilic

Lipophilic

Lipophilicity, , refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene....
contaminants such as oil). Examples of this use include cleaning electronic

Electronics

Electronics refers to the flow of charge through nonmetal electrical conductor , whereas electrical refers to the flow of charge through metal electrical conductor....
devices such as contact pins (like those on ROM

Read-only memory

Read-only memory is a class of computer storage media used in computers and other electronic devices. Because data stored in ROM cannot be modified , it is mainly used to distribute firmware ....
cartridges

Cartridge (electronics)

In various types of electronic equipment, a cartridge can refer to one method of adding different functionality or content; for example, a video game played on a video game console; or a method by which consumables may be replenished, such as an ink cartridge for a printer....
), magnetic tape

Magnetic tape

Magnetic tape is a medium for magnetic recording generally consisting of a thin magnetizable coating on a long and narrow strip of plastic. Nearly all recording tape is of this type, whether used for recording Audio frequency or video or for computer data storage....
deck and floppy disk

Floppy disk

A floppy disk is a data storage medium that is composed of a disk of thin, flexible magnetic storage medium encased in a square or rectangle plastic shell....
drive heads, the lenses of laser

Laser

A laser is a device that emits light through a process called stimulated emission. The term laser is an acronym for light amplification by stimulated emission of radiation....
s in optical disc

Optical disc

In computing, sound reproduction, and video, an optical disc is a flat, circular disc wherein Data is stored in the pits in its flat surface ? sequentially on the continuous, spiral track extending from the innermost track to the outermost track, covering the entire disc surface....
drives (e.g. CD, DVD

DVD

DVD, also known as "Digital Versatile Disc" or "Digital Video Disc,"is a popular optical disc data storage device media format. Its main uses are video and data storage....
) and removing thermal paste from CPUs

Central processing unit

A central processing unit is an electronic circuit that can execute computer programs. This broad definition can easily be applied to many early computers that existed long before the term "CPU" ever came into widespread usage....
. It is also used to clean LCD

Liquid crystal display

A liquid crystal display is an Electro-optic modulator shaped into a thin, flat panel made up of any number of color or monochrome pixels filled with liquid crystals and arrayed in front of a Light#Light sources or reflector....
and glass computer monitor screens (at some risk to the anti-reflection coating of the screen), and used by many music shops to give second-hand or worn records

Gramophone record

A gramophone record is an analog signal sound storage medium consisting of a flat disc with an inscribed modulated spiral groove usually starting near the periphery and ending near the centre of the disc....
newer-looking sheens. It cleans white boards and other unwanted ink related marks very well (at the risk of damaging the non-stick surface of the white board). Isopropyl alcohol also works well at removing smudges, dirt, and fingerprints from cell phones and PDA

PDA

PDA may refer to:...
s. It is effective at removing residual glue from sticky labels. It can also be used to remove stains from most fabrics, wood, cotton, etc.

As a preservative (for biological specimens) isopropyl alcohol provides a cost-effective (when compared to pure ethanol

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
) and comparatively non-toxic alternative to formaldehyde

Formaldehyde

Formaldehyde is a chemical compound with the chemical formula H2CO. It is the simplest aldehyde. Formaldehyde exists in several forms aside from H2CO: the cyclic trimer trioxane and the polymer Polyoxymethylene....
and other synthetic preservatives. When used for the preservation of specimens in solution concentrations of 90-99% are optimal, though concentrations as low as 70% can be used in emergencies.

Sterilizing

Sterilization (microbiology)

Sterilization refers to any process that effectively kills or eliminates transmissible agents from a surface, equipment, article of food or medication, or biological culture medium....
pads typically contain a 60-70% solution

Solution

In chemistry, a solution is a homogeneous mixture composed of two or more substances. In such a mixture, a solute is dissolved in another substance, known as a solvent....
of isopropanol in water

Water (molecule)

File:Blue-water-pool.jpgWater is the most abundant molecule on Earth's surface, constituting about 70% of the Earth's surface in liquid, solid, and gaseous states....
. Isopropyl alcohol is also commonly used as a cleaner

Cleaner

Cleaner is the name of a Germany project specializing in electronic music. Formerly known as Cleen and Cleaner, Myer released several albums on the American industrial music record label, Metropolis Records, as well as the labels Zoth Ommog and Accession Records....
and solvent

Solvent

A solvent is a liquid or gas that dissolves a solid, liquid, or gaseous solute, resulting in a solution.The most common solvent in everyday life is water....
in industry.

Isopropanol is a major ingredient in "dry-gas" fuel additive. In significant quantities, water

Water

Water is a common chemical substance that is essential for the survival of all known forms of life. In typical usage, water refers only to its liquid form or States of matter, but the substance also has a solid state, ice, and a gaseous state, water vapor or steam....
is a problem in fuel tanks as it separates from the gasoline and can freeze in the supply lines at cold temperatures. The isopropanol does not remove the water from the gasoline; rather, the isopropanol solubilizes the water in the gasoline. Once soluble, the water does not pose the same risk as insoluble water as it will no longer accumulate in the supply lines and freeze. Isopropanol is often sold in aerosol cans as a windscreen

Windshield

The windshield or windscreen of an aircraft, automobile, bus, motorcycle, or tram is the front window. Modern windshields are generally made of Laminated glass, a type of treated glass, which consists of two curved sheets of glass with a plastic layer laminated between them for safety, and are Polyurethaned into the window frame....
de-icer.

Isopropanol is used as a water-drying aide for treating otitis externa

Otitis externa

Otitis externa is an inflammation of the outer ear and ear canal. Along with otitis media, external otitis is one of the two human conditions commonly called "earache"....
, better known as swimmers ear.

Chemistry

Unlike ethanol

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
or methanol

Methanol

Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naphtha or wood spirits, is a chemical compound with chemical formula carbonhydrogen3oxygenhydrogen ....
, isopropanol can be separated from aqueous solutions by adding a salt such as sodium chloride

Sodium chloride

Sodium chloride, also known as common salt, table salt, or halite, is a chemical compound with the chemical formula SodiumChlorine....
, sodium sulfate

Sodium sulfate

Sodium sulfate is the sodium salt of sulfuric acid. Anhydrous, it is a white crystalline solid of formula Na2SO4 known as the mineral thenardite; the hydrate Na2SO4?10H2O has been known as Glauber's salt or, historically, sal mirabilis since the 17th century....
, or any of several other inorganic salts, since the alcohol is much less soluble in saline solutions than in salt-free water The process is colloquially called salting out

Salting out

Salting out is a method of separating proteins based on the principle that proteins are less soluble at high salt concentrations. The salt concentration needed for the protein to precipitate out of the solution differs from protein to protein....
, and causes concentrated isopropanol to separate into a distinct layer.

Being a secondary alcohol, isopropanol can be oxidized

Organic redox reaction

Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. In organic chemistry oxidations and reductions are different from ordinary redox reactions because many reactions carry the name but do not actually involve electron transfer in the electrochemistry sense...
to the corresponding ketone

Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
acetone

Acetone

Acetone is the organic compound with the chemical formula OC2. This colorless, mobile, flammable liquid is the simplest example of the ketones....
. This can be achieved using oxidizing agents such as chromic acid

Chromic acid

Chromic acid generally refers to a collection of chemical compound generated by the acidification of solutions containing chromate and dichromate ion or the dissolving of chromium trioxide in sulfuric acid....
, or by dehydrogenation

Dehydrogenation

Dehydrogenation is a chemical reaction that involves the elimination of hydrogen . It is the reverse process of hydrogenation. Dehydrogenation reactions may be either large scale industrial processes or smaller scale laboratory procedures....
of isopropanol over a heated copper catalyst:

₂CH-OH ? (CH₃)₂CO

Acetone

Acetone is the organic compound with the chemical formula OC2. This colorless, mobile, flammable liquid is the simplest example of the ketones....
+ H₂

Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....

Isopropanol may be converted to 2-bromopropane

2-Bromopropane

2-Bromopropane, also known as isopropyl bromide and 2-propyl bromide, is the halogenated hydrocarbon with the formula CH3CHBrCH3....
using phosphorus tribromide

Phosphorus tribromide

Phosphorus tribromide is a colourless liquid with the formula PhosphorusBromine3. It fumes in air due to hydrolysis and has a penetrating odour....
, or dehydrated to propylene

Propylene

Propene, also known as propylene, is an saturation organic chemistry having the chemical formula Carbon3Hydrogen6. It has one covalent bond, and is the second simplest member of the alkene class of hydrocarbons, and it is also second in natural abundance....
by heating with sulfuric acid

Sulfuric acid

Hydride

Hydride is the name given to the Electric charge ion of hydrogen, H-. Although this ion does not exist except in extraordinary conditions, the term hydride is widely applied to describe Chemical compound of hydrogen with other chemical element, particularly those of Periodic table group 1–16....
source in the Meerwein-Ponndorf-Verley reduction

Meerwein-Ponndorf-Verley reduction

The Meerwein-Ponndorf-Verley Reduction in organic chemistry is the organic reduction of ketones to secondary alcohols with aluminumisopropylate catalysis in isopropanol solution ....
.

Like most alcohols, isopropyl alcohol reacts with active metal

Metal

In chemistry, a metal is a chemical element whose atoms readily lose electrons to form positive ions , and form metallic bonds between other metal atoms and ionic bonds between nonmetal atoms....
s such as potassium

Potassium

Potassium is a chemical element. It has the symbol K , atomic number 19, and atomic mass 39.0983. Potassium was first isolated from potash, hence the name....
to form alkoxide

Alkoxide

An alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They can be written as RO–, where R is the organic substituent....
s which can be called isopropoxides. The reaction with aluminium

Aluminium

Aluminium or aluminum is a silvery white and ductile member of the boron group of chemical elements. It has the symbol Al; its atomic number is 13....
(initiated by a trace of mercury

Mercury (element)

Mercury , also called quicksilver or hydrargyrum , is a chemical element with the symbol Hg and atomic number 80. A heavy, silvery d-block metal, mercury is one of six elements that are liquid at or near room temperature and pressure....
) is used to prepare the catalyst aluminium isopropoxide

Aluminium isopropoxide

Aluminium isopropoxide is the chemical compound usually described with the formula Al3, where i-Pr is the isopropyl group . This colourless solid is a useful reagent in organic synthesis....
.

Isopropanol has a maximum absorbance

Absorbance

In spectroscopy, the absorbance A is defined as,where is the intensity of light at a specified wavelength ? that has passed through a sample and is the intensity of the light before it enters the sample or incident light intensity....
at 204 nm in an ultraviolet-visible

Ultraviolet-visible spectroscopy

Ultraviolet-visible spectroscopy or ultraviolet-visible spectrophotometry involves the spectroscopy of photons in the UV-visible region....
spectrum.

Safety

Isopropyl alcohol vapor is more dense than air and is highly flammable with a very wide combustible range. It should be kept away from heat and open flame. When mixed with air or other oxidizers it can explode through deflagration

Deflagration

Deflagration is a technical term describing subsonic combustion that usually propagates through thermal conductivity . Most "fire" found in daily life, from flames to explosions, is technically deflagration....
. Isopropyl alcohol has also been reported to form explosive peroxides

Organic peroxide

Organic peroxides are organic compounds containing the peroxide functional group . If the R' is hydrogen, the compound is called an organic hydroperoxide....
.

Like many organic solvents, long term application to the skin can cause defatting

Defatting

Defatting is a term which is used to describe the removal of fatty acids from an object....
.

Toxicology

Isopropyl alcohol is oxidized by the liver into acetone

Acetone

Acetone is the organic compound with the chemical formula OC2. This colorless, mobile, flammable liquid is the simplest example of the ketones....
by alcohol dehydrogenase

Alcohol dehydrogenase

Alcohol dehydrogenase is an enzyme discovered in the mid-1960s in Drosophila melanogaster. Since then, there has been extensive research on the enzyme....
. Symptom

Symptom

A symptom is a departure from normal function or feeling which is noticed by a patient, indicating the presence of disease or abnormality. A symptom is subjective, observed by the patient, and not measured....
s of isopropyl alcohol poisoning include flushing

Flushing (physiology)

For a person to flush is to become markedly red in the face and often other areas of the skin, from various physiology conditions. Flushing is generally distinguished, despite a close physiological relation between them, from blushing, which is milder, generally restricted to the face or cheeks, and generally assumed to reflect embarrassment....
, headache

Headache

In medicine a headache or wiktionary:cephalalgia is a symptom of a number of different conditions of the head and sometimes neck. Some of the causes are benign while others are medical emergencies....
, dizziness

Dizziness

Dizziness describes a number of subjective symptoms, which the patient may describe as feelings of lightheadedness, floating, wooziness, giddiness, confusion, disorientation or loss of balance....
, CNS depression

CNS depression

Central nervous system depression or CNS depression refers to physiological Depression of the central nervous system that can result in decreased rate of breathing, decreased heart rate, and loss of consciousness possibly leading to coma or death....
, nausea

Nausea

Nausea is the sensation of unease and discomfort in the stomach with an urge to vomit....
, vomiting

Vomiting

Vomiting is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose. Undesired vomiting may result from many causes, ranging from gastritis or poisoning to brain tumors, or elevated intracranial pressure....
, anesthesia

Anesthesia

Anesthesia, or anaesthesia , has traditionally meant the condition of having sensation blocked or temporarily taken away. This allows patients to undergo surgery and other procedures without the distress and pain they would otherwise experience....
, and coma

Coma

In medicine, a coma is a profound state of unconsciousness. A comatose person cannot be awakened, fails to respond normally to pain or light, does not have sleep-wake cycles, and does not take voluntary actions....
. Use in well-ventilated areas and use protective gloves while using. Poisoning can occur from ingestion, inhalation, or absorption.

Isopropyl alcohol is about twice as toxic as ethanol

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
, though isopropyl alcohol does not cause an anion gap acidosis as do ethanol

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
and methanol

Methanol

Hypotension

In physiology and medicine, hypotension refers to an abnormally low blood pressure. This is best understood as a physiologic state, rather than a disease....
and lactic acidosis

Lactic acidosis

Lactic acidosis is a condition caused by the buildup of lactic acid in the body. It leads to acidification of the blood , and is considered a distinct form of metabolic acidosis....
. Such an acid gap is a chemical abnormality in the body fluids where elevated serum proton concentration (acidity) is balanced by an unusual anion that is not normally analysed, and the lowered pH causes depletion of bicarbonate anion. Isopropyl alcohol does produce an osmolal gap

Osmolal gap

Osmolal gap is the difference between measured serum osmolality and calculated serum osmolality....
between the calculated and measured osmolalities of serum, as do the other alcohols. Overdoses may cause a fruity odor on the breath as a result of its metabolism to give acetone

Acetone

Acetone is the organic compound with the chemical formula OC2. This colorless, mobile, flammable liquid is the simplest example of the ketones....
which is not further metabolized. Isopropyl alcohol is more potent than ethanol

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
as a CNS depressant, and its metabolite, acetone, is a CNS depressant in its own right. While around 15 g of isopropanol can be fatal to a 70kg human if left untreated, it is not nearly as toxic as methanol or ethylene glycol

Ethylene glycol

Ethylene glycol is an alcohol with two -OH groups , a chemical compound widely used as an automobile antifreeze. In its pure form, it is an odorless, colorless, syrupy, sweet tasting, toxic liquid....
.

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and calculation