Isopropyl alcohol

Isopropyl alcohol (IUPAC name propan-2-ol; commonly called

isopropanol or 2-propanol) is a colorless, flammable chemical Isopropyl alcohol
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.

It is used in the manufacture of a wide variety of industrial and Names

household chemicals and is a common ingredient in chemicals such
as antiseptics, disinfectants, and detergents. Preferred IUPAC name
Propan-2-ol[2]
Other names

Contents 2-Propanol
Isopropanol[1]
Names Rubbing alcohol
Properties sec-Propyl alcohol
2-Hydroxypropane
Reactions
i-PrOH
History Dimethyl carbinol
Production IPA
Biological
Identifiers
Indirect hydration
CAS Number 67-63-0 (http://www.co
Direct hydration
mmonchemistry.org/C
Hydrogenation of acetone
hemicalDetail.aspx?re
Uses f=67-63-0)
Solvent
3D model (JSmol) Interactive image (http
Intermediate
Medical s://chemapps.stolaf.ed
u/jmol/jmol.php?model
Early uses as an anesthetic
=CC%28O%29C)
Automotive
Laboratory Beilstein 635639
Reference
Safety
ChEBI CHEBI:17824 (https://
Toxicology www.ebi.ac.uk/chebi/s
References earchId.do?chebiId=1
External links 7824)
ChEMBL ChEMBL582 (https://w
ww.ebi.ac.uk/chembld
Names b/index.php/compoun
d/inspect/ChEMBL58
Isopropyl alcohol is also known as 2-propanol, sec-propyl alcohol,
2)
IPA, or isopropanol. IUPAC considers isopropanol an incorrect
name as the hydrocarbon isopropane does not exist.[1] ChemSpider 3644 (http://www.che
mspider.com/Chemica
Properties l-Structure.3644.html)

ECHA InfoCard 100.000.601 (https://e

cha.europa.eu/substa
Isopropyl alcohol is miscible in water, ethanol, ether, and nce-information/-/subs
chloroform. It dissolves ethyl cellulose, polyvinyl butyral, many oils, tanceinfo/100.000.60
alkaloids, gums and natural resins.[9] Unlike ethanol or methanol, 1)
isopropyl alcohol is not miscible with salt solutions and can be
Gmelin Reference 1464
separated from aqueous solutions by adding a salt such as sodium
chloride. The process is colloquially called salting out, and causes KEGG D00137 (https://www.k
concentrated isopropyl alcohol to separate into a distinct layer.[10] egg.jp/entry/D00137)

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% PubChem CID 3776 (https://pubche
(91 vol%) isopropyl alcohol. Water–isopropyl alcohol mixtures have m.ncbi.nlm.nih.gov/co
depressed melting points.[10] It has a slightly bitter taste, and is not mpound/3776)
safe to drink.[10][11]
RTECS number NT8050000
Isopropyl alcohol becomes increasingly viscous with decreasing UNII ND2M416302 (https://
temperature and freezes at −89 °C (−128 °F). fdasis.nlm.nih.gov/srs/
Isopropyl alcohol has a maximal absorbance at 205 nm in an srsdirect.jsp?regno=N
ultraviolet–visible spectrum.[12][13] D2M416302)
UN number 1219
Reactions CompTox DTXSID7020762 (http
Dashboard (EPA)
s://comptox.epa.gov/d
Isopropyl alcohol can be oxidized to acetone, which is the ashboard/DTXSID702
corresponding ketone. This can be achieved using oxidizing agents 0762)
such as chromic acid, or by dehydrogenation of isopropyl alcohol
over a heated copper catalyst: InChI
InChI=1S/C3H7OH/c1-3(2)4/h3-4H,1-2H3
(CH3)2CHOH → (CH3)2CO + H2 Key: KFZMGEQAYNKOFK-UHFFFAOYSA-N

SMILES
Isopropyl alcohol is often used as both solvent and hydride source
CC(O)C
in the Meerwein-Ponndorf-Verley reduction and other transfer
hydrogenation reactions. Isopropyl alcohol may be converted to 2- Properties
bromopropane using phosphorus tribromide, or dehydrated to
Chemical formula C3H8O
propene by heating with sulfuric acid.
Molar mass 60.096 g·mol−1
Like most alcohols, isopropyl alcohol reacts with active metals such Appearance Colorless liquid
as potassium to form alkoxides that can be called isopropoxides.
The reaction with aluminium (initiated by a trace of mercury) is Odor pungent alcoholic
used to prepare the catalyst aluminium isopropoxide.[14] odour
Density 0.786 g/cm3 (20 °C)
History Melting point −89 °C (−128 °F;
184 K)
In 1920, Standard Oil first produced isopropyl alcohol by hydrating Boiling point 82.6 °C (180.7 °F;
propene. Its major use at the time was not rubbing alcohol but for
355.8 K)
oxidation to acetone, whose first major use was in World War I for
the preparation of cordite, a smokeless, low explosive propellant.[15] Solubility in water Miscible with water
Solubility Miscible with
Production benzene, chloroform,
ethanol, ether,
In 1994, 1.5 million tonnes of isopropyl alcohol were produced in glycerin; soluble in
the United States, Europe, and Japan.[16] It is primarily produced acetone
by combining water and propene in a hydration reaction or by log P 0.16[3]
hydrogenating acetone.[16][17] There are two routes for the
Acidity (pKa) 16.5[4]
hydration process and both processes require that the isopropyl
alcohol be separated from water and other by-products by Magnetic −45.794·10−6 cm3/mol
distillation. Isopropyl alcohol and water form an azeotrope, and susceptibility (χ)
simple distillation gives a material that is 87.9% by weight isopropyl 1.3776
alcohol and 12.1% by weight water.[18] Pure (anhydrous) isopropyl Refractive index
alcohol is made by azeotropic distillation of the wet isopropyl (nD)
alcohol using either diisopropyl ether or cyclohexane as azeotroping Viscosity 2.86 cP at 15 °C
agents.[16] 1.96 cP at 25 °C[5]
1.77 cP at 30 °C[5]
Biological Dipole moment 1.66 D (gas)
Pharmacology
Small amounts of isopropyl alcohol are produced in the body in
ATC code D08AX05 (WHO (http
diabetic ketoacidosis.[19]
s://www.whocc.no/atc
_ddd_index/?code=D
Indirect hydration 08AX05))
Hazards
Indirect hydration reacts propene with sulfuric acid to form a
mixture of sulfate esters. This process can use low-quality propene, Main hazards Flammable
and is predominant in the USA. These processes give primarily Safety data sheet See: data page
isopropyl alcohol rather than 1-propanol, because adding water or External MSDS (http://
sulfuric acid to propene follows Markovnikov's rule. Subsequent msds.chem.ox.ac.uk/
hydrolysis of these esters by steam produces isopropyl alcohol, by
PR/2-propanol.html)
distillation. Diisopropyl ether is a significant by-product of this
process; it is recycled back to the process and hydrolyzed to give the GHS pictograms
desired product.[16]
H2SO4 GHS Signal word Danger
CH3CH=CH2 + H2O ⟶ (CH3)2CHOH
GHS hazard H225, H319, H336
statements
Direct hydration GHS P210, P261,
precautionary P305+351+338
Direct hydration reacts propene and water, either in gas or liquid statements
phase, at high pressures in the presence of solid or supported acidic NFPA 704
catalysts. This type of process usually requires higher-purity (fire diamond) 3
propylene (> 90%).[16] Direct hydration is more commonly used in 1 0
Europe.
Flash point Open cup: 11.7 °C
Hydrogenation of acetone (53.1 °F; 284.8 K)
Closed cup: 13 °C
Isopropyl alcohol may be prepared via the hydrogenation of (55 °F)
acetone, however this approach involves an extra step compared to Autoignition 399 °C (750 °F;
the above methods, as acetone is itself normally prepared from temperature 672 K)
propene via the cumene process.[16] It may remain economical
depending on the value of the products. A known issue is the Explosive limits 2–12.7%
formation of MIBK and other self-condensation products. Raney Threshold limit 980 mg/m3
nickel was one of the original industrial catalysts, modern catalysts value (TLV) (TWA), 1225 mg/m3
are often supported bimetallic materials. This is an efficient process (STEL)
and easy
Lethal dose or concentration (LD, LC):

Uses LD50 (median

dose)
12800 mg/kg (dermal,
rabbit)
In 1990, 45,000 metric tonnes of isopropyl alcohol were used in the 3600 mg/kg (oral,
United States, mostly as a solvent for coatings or for industrial mouse)
processes. In that year, 5400 metric tonnes were used for 5045 mg/kg (oral, rat)
household purposes and in personal care products. Isopropyl
alcohol is popular in particular for pharmaceutical applications,[16] 6410 mg/kg (oral,
due to its low toxicity. Some isopropyl alcohol is used as a chemical rabbit)[7]
intermediate. Isopropyl alcohol may be converted to acetone, but LC50 (median 53,000 mg/m3
the cumene process is more significant. [16] concentration)
Solvent (inhalation, mouse)
12,000 ppm (rat,
Isopropyl alcohol dissolves a wide range of non-polar compounds. 8 hr)[7]
It also evaporates quickly, leaves nearly zero oil traces, compared to
ethanol, and is relatively non-toxic, compared to alternative LCLo (lowest 16,000 ppm (rat, 4 hr)
published)
solvents. Thus, it is used widely as a solvent and as a cleaning fluid, 12,800 ppm (mouse,
especially for dissolving oils. Together with ethanol, n-butanol, and 3 hr)[7]
methanol, it belongs to the group of alcohol solvents, about 6.4
million tonnes of which were used worldwide in 2011.[20] NIOSH (US health exposure limits):
PEL TWA 400 ppm
Isopropyl alcohol is commonly used for cleaning eyeglasses, (Permissible) (980 mg/m3)[6]
electrical contacts, audio or video tape heads, DVD and other
REL TWA 400 ppm
optical disc lenses, removing thermal paste from heatsinks on CPUs (Recommended) (980 mg/m3), ST
and other IC packages, etc.
500 ppm (1225
mg/m3)[6]
Intermediate IDLH 2000 ppm[6]
(Immediate
Isopropyl alcohol is esterified to give isopropyl acetate, another danger)
solvent. It reacts with carbon disulfide and sodium hydroxide to
Related compounds
give sodium isopropylxanthate, a herbicide and an ore flotation
reagent.[21] Isopropyl alcohol reacts with titanium tetrachloride and Related alcohols 1-Propanol, ethanol,
aluminium metal to give titanium and aluminium isopropoxides, 2-butanol
respectively, the former a catalyst, and the latter a chemical Supplementary data page
reagent.[16] This compound may serve as a chemical reagent in
Structure and Refractive index (n),
itself, by acting as a dihydrogen donor in transfer hydrogenation. properties Dielectric constant
(εr), etc.
Medical Thermodynamic Phase behaviour
data solid–liquid–gas
Rubbing alcohol, hand sanitizer, and disinfecting pads typically
contain a 60–70% solution of isopropyl alcohol or ethanol in water. Spectral data UV, IR, NMR, MS
Water is required to open up membrane pores of bacteria, which Except where otherwise noted, data are
acts as a gateway for isopropyl alcohol. A 75% v/v solution in water given for materials in their standard state
may be used as a hand sanitizer.[22] Isopropyl alcohol is used as a (at 25 °C [77 °F], 100 kPa).
water-drying aid for the prevention of otitis externa, better known verify (what is ?)
as swimmer's ear.[23]
Infobox references

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[24] or as an anesthetic by inhaling the
fumes or orally. Early uses included using the solvent as general
anesthetic for small mammals[25] 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 Isopropyl alcohol
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 One of the small scale uses of

isopropanol is in cloud chambers.
Isopropanol has ideal physical and
As a biological specimen preservative, isopropyl alcohol provides a
chemical properties to form a
comparatively non-toxic alternative to formaldehyde and other synthetic
supersaturated layer of vapor which
preservatives. Isopropyl alcohol solutions of 70–99% are used to
can be condensed by particles of
preserve specimens. radiation.

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.[26] Distillation of isopropyl alcohol over
magnesium has been reported to form peroxides, which may explode upon concentration.[27][28] Isopropyl
alcohol is a skin irritant.[26][29][30] Wearing protective gloves is recommended.

Toxicology
Isopropyl alcohol and its metabolite, acetone, act as central nervous system (CNS) depressants.[31] 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.[31] Overdoses may cause a fruity odor on the breath as a
result of its metabolism to acetone.[32] 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.[31]

Isopropyl alcohol is oxidized to form acetone by alcohol dehydrogenase in the liver,[31] and has a biological
half-life in humans between 2.5 and 8.0 hours.[31] 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.[33]

In forensic pathology, people who have died as a result of diabetic ketoacidosis usually have blood
concentrations of isopropyl alcohol of tens of mg/dL, while those by fatal isopropyl alcohol ingestion usually
have blood concentrations of hundreds of mg/dL.[19]

References
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D, E, F, and H. Oxford: Pergamon Press. 1979. "Designations such as isopropanol, sec-butanol, and tert-
butanol are incorrect because there are no hydrocarbons isopropane, sec-butane, and tert-butane to
which the suffix "-ol" can be added; such names should be abandoned. Isopropyl alcohol, sec-butyl
alcohol, and tert-butyl alcohol are, however, permissible (see Rule C-201.3) because the radicals
isopropyl, sec-butyl, and tert-butyl do exist."
2. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book).
Cambridge: The Royal Society of Chemistry. 2014. p. 631. doi:10.1039/9781849733069 (https://doi.org/1
0.1039%2F9781849733069). ISBN 978-0-85404-182-4.
 3. "Isopropanol_msds" (https://www.chemsrc.com/en/cas/67-63-0_766167.html). chemsrc.com.
4. Reeve, W.; Erikson, C.M.; Aluotto, P.F. (1979). "A new method for the determination of the relative
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Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
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Detection of Isopropanol in Ketoacidosis". Journal of Forensic Sciences. 57 (3): 674–678.
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ricoto/CommonHealthProblems/OtitisExternaSwimmersEar.htm). Medical College of Wisconsin
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External links
CDC – NIOSH Pocket Guide to Chemical Hazards - Isopropyl alcohol (https://www.cdc.gov/niosh/npg/np
gd0359.html)
Environmental Health Criteria 103: 2-Propanol (http://www.inchem.org/documents/ehc/ehc/ehc103.htm)

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