Isopropyl alcohol

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Isopropyl alcohol
Skeletal formula of isopropyl alcohol 2-Propanol.svg
Skeletal formula of isopropyl alcohol
Ball-and-stick model of isopropyl alcohol Propan-2-ol-3D-balls.png
Ball-and-stick model of isopropyl alcohol
Names
Preferred IUPAC name
Propan-2-ol [1]
Other names
2-Propanol
Isopropanol [2]
Rubbing alcohol
sec-Propyl alcohol
s-Propanol
iPrOH
i-PrOH
IpOH
Dimethyl carbinol
IPA
Identifiers
3D model (JSmol)
635639
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.601
1464
KEGG
PubChem CID
RTECS number
  • NT8050000
UNII
UN number 1219
Properties
C3H8O
Molar mass 60.096 g·mol−1
AppearanceColorless liquid
Density 0.786 g/cm3 (20 °C)
Melting point −89 °C (−128 °F; 184 K)
Boiling point 82.6 °C (180.7 °F; 355.8 K)
Miscible with water
Solubility Miscible with benzene, chloroform, ethanol, ether, glycerin; soluble in acetone
log P 0.16 [3]
Acidity (pKa)16.5 [4]
−45.794·10−6 cm3/mol
1.3776
Viscosity 2.86 cP at 15 °C
1.96 cP at 25 °C [5]
1.77 cP at 30 °C [5]
1.66  D (gas)
Pharmacology
D08AX05 ( WHO )
Hazards
Main hazards Flammable
Safety data sheet See: data page
External MSDS
GHS pictograms GHS-pictogram-exclam.svg GHS-pictogram-flamme.svg
GHS Signal word Danger
H225, H319, H336
P210, P261, P305+351+338
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeIsopropyl alcohol
3
1
0
Flash point Open cup:11.7 °C (53.1 °F; 284.8 K)
Closed cup: 13 °C (55 °F)
399 °C (750 °F; 672 K)
Explosive limits 2–12.7%
980 mg/m3 (TWA), 1225 mg/m3 (STEL)
Lethal dose or concentration (LD, LC):
  • 12800 mg/kg (dermal, rabbit)[ citation needed ]
  • 3600 mg/kg (oral, mouse)
  • 5045 mg/kg (oral, rat)
  • 6410 mg/kg (oral, rabbit) [6]
  • 16,000 ppm (rat, 4 hr)
  • 12,800 ppm (mouse, 3 hr) [6]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 400 ppm (980 mg/m3) [7]
REL (Recommended)
TWA 400 ppm (980 mg/m3), ST 500 ppm (1225 mg/m3) [7]
IDLH (Immediate danger)
2000 ppm [7]
Related compounds
Related alcohols
1-Propanol, ethanol, 2-butanol
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solidliquidgas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Isopropyl alcohol (IUPAC name propan-2-ol; commonly called isopropanol or 2-propanol) is a colorless, flammable chemical compound (chemical formula CH3CHOHCH3) with a strong odor. [8] As an isopropyl group linked to a hydroxyl group, it is the simplest example of a secondary alcohol, where the alcohol carbon atom is attached to two other carbon atoms. It is a structural isomer of 1-propanol and ethyl methyl ether.

Contents

It is used in the manufacture of a wide variety of industrial and household chemicals, and is a common ingredient in chemicals such as antiseptics, disinfectants, and detergents.

Names

Isopropyl alcohol is also known as 2-propanol, sec-propyl alcohol, IPA, or isopropanol. IUPAC considers isopropanol an incorrect name as the hydrocarbon isopropane does not exist. [2]

Properties

Isopropyl alcohol is miscible in water, ethanol, ether, and chloroform. It dissolves ethyl cellulose, polyvinyl butyral, many oils, alkaloids, gums and natural resins. [9] Unlike ethanol or methanol, isopropyl alcohol is not miscible with salt solutions and can be separated from aqueous solutions by adding a salt such as sodium chloride. The process is colloquially called salting out , and causes concentrated isopropyl alcohol to separate into a distinct layer. [10]

Isopropyl alcohol forms an azeotrope with water, which gives a boiling point of 80.37 °C (176.67 °F) and a composition of 87.7 wt% (91 vol%) isopropyl alcohol. Water-isopropyl alcohol mixtures have depressed melting points. [10] It has a slightly bitter taste, and is not safe to drink. [10] [11]

Isopropyl alcohol becomes increasingly viscous with decreasing temperature and freezes at −89 °C (−128 °F).

Isopropyl alcohol has a maximum absorbance at 205 nm in an ultraviolet-visible spectrum. [12] [13]

Reactions

Isopropyl alcohol can be oxidized to acetone, which is the corresponding ketone. This can be achieved using oxidizing agents such as chromic acid, or by dehydrogenation of isopropyl alcohol over a heated copper catalyst:

(CH3)2CHOH → (CH3)2CO + H2

Isopropyl alcohol is often used as both solvent and hydride source in the Meerwein-Ponndorf-Verley reduction and other transfer hydrogenation reactions. Isopropyl alcohol may be converted to 2-bromopropane using phosphorus tribromide, or dehydrated to propene by heating with sulfuric acid.

Like most alcohols, isopropyl alcohol reacts with active metals such as potassium to form alkoxides that can be called isopropoxides. The reaction with aluminium (initiated by a trace of mercury) is used to prepare the catalyst aluminium isopropoxide. [14]

History

In 1920, Standard Oil first produced isopropyl alcohol by hydrating propene. Its major use at the time was not rubbing alcohol but for oxidation to acetone, whose first major use was in World War I for the preparation of cordite, a smokeless, low explosive propellant. [15]

Production

In 1994, 1.5 million tonnes of isopropyl alcohol were produced in the United States, Europe, and Japan. [16] It is primarily produced by combining water and propene in a hydration reaction or by hydrogenating acetone. [16] [17] 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. Isopropyl alcohol and water form an azeotrope and simple distillation gives a material that is 87.9% by weight isopropyl alcohol and 12.1% by weight water. [18] Pure (anhydrous) isopropyl alcohol is made by azeotropic distillation of the wet isopropyl alcohol using either diisopropyl ether or cyclohexane as azeotroping agents. [16]

Indirect hydration

Indirect hydration reacts propene with sulfuric acid 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. Subsequent hydrolysis of these esters by steam produces isopropyl alcohol, by distillation. Diisopropyl ether is a significant by-product of this process; it is recycled back to the process and hydrolyzed to give the desired product. [16]

Direct hydration

Direct hydration reacts propene and water, either in gas phase or in liquid phase, at high pressures in the presence of solid or supported acidic catalysts. This type of process usually requires higher-purity propylene (> 90%). [16] Direct hydration is more commonly used in Europe.

Hydrogenation of acetone

Crude acetone is hydrogenated in the liquid phase over Raney nickel or a mixture of copper and chromium oxide to give isopropyl alcohol. This process is useful, when it is coupled with excess acetone production, such as the cumene process. [16]

Uses

One of the small scale uses of isopropanol is in cloud chambers. Isopropanol has ideal physical and chemical properties to form a supersaturated layer of vapor which can be condensed by particles of radiation. One of the small scale uses of isopropanol is in cloud chambers. Isopropanol has ideal physical and chemical properties to form a supersaturated layer of vapor which can be condensed by particles of radiation.jpg
One of the small scale uses of isopropanol is in cloud chambers. Isopropanol has ideal physical and chemical properties to form a supersaturated layer of vapor which can be condensed by particles of radiation.

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 tons were used for household purposes and in personal care products. Isopropyl alcohol is popular in particular for pharmaceutical applications, [16] due to its low toxicity. Some isopropyl alcohol is used as a chemical intermediate. Isopropyl alcohol may be converted to acetone, but the cumene process is more significant. It is also used as a gasoline additive. [16]

Solvent

Isopropyl alcohol dissolves a wide range of non-polar compounds. It also evaporates quickly, leaves nearly zero oil traces, compared to ethanol, and is relatively non-toxic, compared to alternative solvents. Thus, it is used widely as a solvent and as a cleaning fluid, especially for dissolving oils. Together with ethanol, n-butanol, and methanol, it belongs to the group of alcohol solvents, about 6.4 million tonnes of which were used worldwide in 2011. [19]

Isopropyl alcohol is commonly used for cleaning eyeglasses, electrical contacts, audio or video tape heads, DVD and other optical disc lenses, removing thermal paste from heatsinks on CPUs and other IC packages, etc.

Intermediate

Isopropyl alcohol is esterified to give isopropyl acetate, another solvent. It reacts with carbon disulfide and sodium hydroxide to give sodium isopropylxanthate, a herbicide and an ore flotation reagent. [20] Isopropyl alcohol reacts with titanium tetrachloride and aluminium metal to give titanium and aluminium isopropoxides, respectively, the former a catalyst, and the latter a chemical reagent. [16] This compound may serve as a chemical reagent in itself, by acting as a dihydrogen donor in transfer hydrogenation.

Medical

Rubbing alcohol, hand sanitizer, and disinfecting pads typically contain a 60–70% solution of isopropyl alcohol or ethanol in water. Water is required to open up membrane pores of bacteria, which acts as a gateway for isopropyl alcohol. A 75% v/v solution in water may be used as a hand sanitizer. [21] Isopropyl alcohol is used as a water-drying aid for the prevention of otitis externa, better known as swimmer's ear. [22]

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 [23] or as an anesthetic by inhaling the fumes or orally. Early uses included using the solvent as general anesthetic for small mammals [24] 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 additives. In significant quantities water 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, water does not pose the same risk as insoluble water, as it no longer accumulates in the supply lines and freezes, but is consumed with the fuel itself. Isopropyl alcohol is often sold in aerosol cans as a windshield or door lock deicer. Isopropyl alcohol is also used to remove brake fluid traces from hydraulic braking systems, so that the brake fluid (usually DOT 3, DOT 4, or mineral oil) does not contaminate the brake pads 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 and other synthetic preservatives. Isopropyl alcohol solutions of 70–99% are used to preserve specimens.

Isopropyl alcohol is often used in DNA extraction. 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.

Safety

Isopropyl alcohol vapor is denser than air and is flammable, with a flammability range of between 2 and 12.7% in air. It should be kept away from heat and open flame. [25] Distillation of isopropyl alcohol over magnesium has been reported to form peroxides, which may explode upon concentration. [26] [27] Isopropyl alcohol is a skin irritant. [25] [28] [29] Wearing protective gloves is recommended.

Toxicology

Isopropyl alcohol and its metabolite, acetone, act as central nervous system (CNS) depressants. [30] Poisoning can occur from ingestion, inhalation, or skin absorption. Symptoms of isopropyl alcohol poisoning include flushing, headache, dizziness, CNS depression, nausea, vomiting, anesthesia, hypothermia, low blood pressure, shock, respiratory depression, and coma. [30] Overdoses may cause a fruity odor on the breath as a result of its metabolism to acetone. [31] 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. [30]

Isopropyl alcohol is oxidized to form acetone by alcohol dehydrogenase in the liver, [30] and has a biological half-life in humans between 2.5 and 8.0 hours. [30] Unlike methanol or ethylene glycol 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, an alcohol dehydrogenase inhibitor, unless co-ingestion with methanol or ethylene glycol is suspected. [32]

Related Research Articles

Alcohol any organic compound in which the hydroxyl functional group (–OH) is bound to a saturated carbon atom

In chemistry, alcohols are organic compounds that carry at least one hydroxyl functional group (−OH) bound to a saturated carbon atom. The term alcohol originally referred to the primary alcohol ethanol (ethyl alcohol), which is used as a drug and is the main alcohol present in alcoholic beverages. An important class of alcohols, of which methanol and ethanol are the simplest members, includes all compounds for which the general formula is CnH2n+1OH. Simple monoalcohols that are the subject of this article include primary (RCH2OH), secondary (R2CHOH) and tertiary (R3COH) alcohols.

Ethanol is a chemical compound, a simple alcohol with the chemical formula C
2
H
6
O
. Its formula can be also written as CH
3
CH
2
OH or C
2
H
5
OH, and is often abbreviated as EtOH. Ethanol is a volatile, flammable, colorless liquid with a slight characteristic odor. It is a psychoactive substance and is the principal active ingredient found in alcoholic drinks.

Solvent substance that dissolves a solute (a chemically different liquid, solid or gas), resulting in a solution

A solvent is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. The quantity of solute that can dissolve in a specific volume of solvent varies with temperature. Common uses for organic solvents are in dry cleaning, as paint thinners, as nail polish removers and glue solvents, in spot removers, in detergents and in perfumes (ethanol). Water is a solvent for polar molecules and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within a cell. Solvents find various applications in chemical, pharmaceutical, oil, and gas industries, including in chemical syntheses and purification processes.

Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4H9OH, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; all are a butyl or isobutyl group linked to a hydroxyl group (sometimes represented as BuOH, n-BuOH, i-BuOH, and t-BuOH). These are n-butanol, 2 stereoisomers of sec-butanol, isobutanol and tert-butanol. Butanol is primarily used as a solvent, as an intermediate in chemical synthesis, and as a fuel. It is sometimes also called biobutanol when produced biologically and petrobutanol when produced from petroleum; those two names refer to the same substance, but highlight their different origins.

Azeotrope mixture of two or more liquids whose proportions do not change while the mixture is boiling

An azeotrope or a constant boiling point mixture is a mixture of two or more liquids whose proportions cannot be altered or changed by simple distillation. This happens because when an azeotrope is boiled, the vapour has the same proportions of constituents as the unboiled mixture. Because their composition is unchanged by distillation, azeotropes are also called constant boiling point mixtures.

Petrochemical chemical product derived from petroleum

Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.

Denatured alcohol Ethanol with additives to discourage recreational consumption

Denatured alcohol, also called methylated spirit or denatured rectified spirit, is ethanol that has additives to make it poisonous, bad-tasting, foul-smelling, or nauseating to discourage recreational consumption. It is sometimes dyed so that it can be identified visually. Pyridine, methanol, or both can be added to make denatured alcohol poisonous, and denatonium can be added to make it bitter.

Tetrahydrofuran chemical compound

Tetrahydrofuran (THF) is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent.

Propylene oxide chemical compound

Propylene oxide is an organic compound with the molecular formula CH3CHCH2O. This colourless volatile liquid with an odour resembling ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols for use in making polyurethane plastics. It is a chiral epoxide, although it is commonly used as a racemic mixture.

Fusel alcohols or fuselol, also sometimes called fusel oils in Europe, are mixtures of several alcohols produced as a by-product of alcoholic fermentation. The word Fusel[ˈfuːzl̩] is German for "bad liquor".

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 addition of benzene to water and ethanol. This practice of adding an entrainer which forms a separate phase is a specific sub-set of (industrial) azeotropic distillation methods, or combination thereof. In some senses, adding an entrainer is similar to extractive distillation.

Diisopropyl ether chemical compound

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 organic solvents. It is used as an extractant and an oxygenate gasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propene. Diisopropyl ether is sometimes represented by the abbreviation "DIPE".

Isobutylene chemical compound

Isobutylene is a hydrocarbon of industrial significance. It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. At standard temperature and pressure it is a colourless flammable gas.

2-Butanol group of stereoisomers

2-Butanol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. This secondary alcohol is a flammable, colorless liquid that is soluble in 3 parts water and completely miscible with organic solvents. It is produced on a large scale, primarily as a precursor to the industrial solvent methyl ethyl ketone. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-butanol and (S)-(+)-2-butanol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

Acetone chemical compound

Acetone, or propanone, is an organic compound with the formula (CH3)2CO. It is the simplest and smallest ketone. It is a colorless, volatile, flammable liquid with a characteristic odor.

<i>tert</i>-Butyl alcohol chemical compound

tert-Butyl alcohol (TBA), also called tert-butanol or t-butanol, is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). It is one of the four isomers of butanol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

Reactive distillation is a process where the chemical reactor is also the still. Separation of the product from the reaction mixture does not need a separate distillation step which saves energy and materials. This technique can be useful for equilibrium-limited reactions such as esterification and ester hydrolysis reactions. Conversion can be increased beyond what is expected by the equilibrium due to the continuous removal of reaction products from the reactive zone. This approach can also reduce capital and investment costs.

1-Propanol chemical compound

1-Propanol is a primary alcohol with the formula CH
3
CH
2
CH
2
OH
. This colorless liquid is also known as propan-1-ol, 1-propyl alcohol, n-propyl alcohol, and n-propanol. It is an isomer of 2-propanol. It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters.

Acetic acid A colorless and faint liquid organic compound found in vinegar

Acetic acid, systematically named ethanoic acid, is a colourless liquid organic compound with the chemical formula CH3COOH (also written as CH3CO2H or C2H4O2). When undiluted, it is sometimes called glacial acetic acid. Vinegar is no less than 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. Acetic acid has a distinctive sour taste and pungent smell. In addition to household vinegar, it is mainly produced as a precursor to polyvinyl acetate and cellulose acetate. It is classified as a weak acid since it only partially dissociates in solution, but concentrated acetic acid is corrosive and can attack the skin.

References

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