Isopropyl alcohol: Difference between revisions
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===Intermediate=== |
===Intermediate=== |
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Isopropyl alcohol is esterified to give [[isopropyl acetate]], another solvent. It reacts with [[carbon disulfide]] to give [[sodium isopropylxanthate]], a weed killer. Isopropyl alcohol reacts with [[titanium tetrachloride]] and [[aluminium]] metal to give [[titanium isopropoxide|titanium]] and [[aluminium isopropoxide]]s respectively, the former a catalyst, and the latter a chemical reagent.<ref name = Ullmann/> This compound may serve as a chemical reagent in itself, by acting as a dihydrogen donor in [[transfer hydrogenation]]. |
Isopropyl likes having sex with alcohol is esterified to give [[isopropyl acetate]], another solvent. It reacts with [[carbon disulfide]] to give [[sodium isopropylxanthate]], a weed killer. Isopropyl alcohol reacts with [[titanium tetrachloride]] and [[aluminium]] metal to give [[titanium isopropoxide|titanium]] and [[aluminium isopropoxide]]s respectively, the former a catalyst, and the latter a chemical reagent.<ref name = Ullmann/> This compound may serve as a chemical reagent in itself, by acting as a dihydrogen donor in [[transfer hydrogenation]]. |
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===Medical=== |
===Medical=== |
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Revision as of 17:07, 20 January 2012
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| Names | |||
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| IUPAC name
isopropyl alcohol
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| Preferred IUPAC name
propan-2-ol | |||
| Other names
2-propanol, isopropanol, isopropyl alcohol, rubbing alcohol, iPrOH
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| Identifiers | |||
3D model (JSmol)
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| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.000.601 | ||
| KEGG | |||
PubChem CID
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| RTECS number |
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| UNII | |||
| UN number | 1219 | ||
CompTox Dashboard (EPA)
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| Properties | |||
| C3H8O | |||
| Molar mass | 60.096 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Density | 0.786 g/cm3 (20 °C) | ||
| Melting point | −89 °C (−128 °F; 184 K) | ||
| Boiling point | 82.5 °C (180.5 °F; 355.6 K) | ||
| miscible | |||
| Solubility | miscible in benzene, chloroform, ethanol, ether, glycerin soluble in acetone insoluble in salt solutions | ||
| Acidity (pKa) | 16.5 | ||
Refractive index (nD)
|
1.3776 | ||
| Viscosity | 2.86 cP at 15 °C 1.96 cP at 25 °C[1] 1.77 cP at 30 °C For 187K-500K, viscosity (cP) =10^(-0.7009+(8.4150E+02/T)+(-8.6068E-03*T)+(8.2964E-06*(T^2))) (Temp in K)[1] | ||
| 1.66 D (gas) | |||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards
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Flammable | ||
| NFPA 704 (fire diamond) | |||
| Flash point | 11.7 °C (open cup) 13 °C (closed cup) | ||
Threshold limit value (TLV)
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400 ppm (TWA), 500 ppm (STEL) | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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5050 mg/kg (rat, oral)[2] | ||
| Related compounds | |||
| Supplementary data page | |||
| Isopropyl alcohol (data page) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Isopropyl alcohol (also Isopropanol, propan-2-ol, 2-propanol or the abbreviation IPA) is a common name for a chemical compound with the molecular formula C3H8O. It is a colorless, flammable chemical compound with a strong odor. It is the simplest example of a secondary alcohol, where the alcohol carbon is attached to two other carbons sometimes shown as (CH3)2CHOH. It is a structural isomer of propanol.
Properties
Isopropyl alcohol has a maximum absorbance at 204 nm in an ultraviolet-visible spectrum.[citation needed] Unlike ethanol or methanol, isopropyl alcohol can be separated from aqueous solutions by adding a salt such as sodium chloride, sodium sulfate, or any of several other inorganic salts, since the alcohol is much less soluble in saline solutions than in salt-free water[3] The process is colloquially called salting out, and causes concentrated isopropyl alcohol to separate into a distinct layer.[citation needed]
Being a secondary alcohol, 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:
Isopropyl alcohol is often used as both solvent and hydride source in the Meerwein-Ponndorf-Verley reduction and other transfer hydrogenation reactions; it is oxidized to acetone.
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 which can be called isopropoxides. The reaction with aluminium (initiated by a trace of mercury) is used to prepare the catalyst aluminium isopropoxide.[4]
Production
In 1994, 1.5 million tonnes of isopropyl alcohol was produced in the United States, Europe, and Japan.[5] This compound is primarily produced by combining water and propene in a hydration reaction. Of minor significance is the hydrogenation of acetone.[5][6]
There are two routes for the hydration process: indirect hydration via the sulfuric acid process, and direct hydration. The former process, which can use low-quality propene, predominates in the USA while the latter process, which requires high-purity propene, is more commonly used in Europe. These processes give predominantly isopropyl alcohol rather than 1-propanol because the addition of water or sulfuric acid to propene follows Markovnikov's rule.
- Indirect hydration
The indirect process reacts propene with sulfuric acid to form a mixture of sulfate esters. Subsequent hydrolysis of these esters by steam produces isopropyl alcohol, which is distilled. Diisopropyl ether is a significant by-product of this process; it is recycled back to the process and hydrolyzed to give the desired product.[5]
- Direct hydration
Direct hydration reacts propene and water, either in gas or liquid phases, at high pressures in the presence of solid or supported acidic catalysts. Higher purity propylene (> 90 %) tends to be required for this type of process.[5]
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 which is 87.9% by weight isopropyl alcohol and 12.1% by weight water.[7] Pure (anhydrous) isopropyl alcohol is made by azeotropic distillation of the wet isopropyl alcohol using either diisopropyl ether or cyclohexane as azeotroping agents.[5]
- 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 coupled with excess acetone production, such as the cumene process.[5]
Uses
In 1990, 45 thousand tonnes of isopropyl alcohol was consumed in the United States. The vast majority of isopropyl alcohol was used as a solvent for coatings or for industrial processes. Isopropyl alcohol in particular is popular for pharmaceutical applications,[5] presumably due to the low toxicity of any residues. Some isopropyl alcohol is used as a chemical intermediate. Isopropyl alcohol may be converted to acetone, but the cumene process is more significant. In that year, a significant fraction (5.4 tonnes) was consumed for household use and in personal care products. It is also used as a gasoline additive.[5]
Solvent
Isopropyl alcohol dissolves a wide range of non-polar compounds. It also evaporates quickly 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.
Examples of this application include cleaning electronic devices such as contact pins (like those on ROM cartridges), magnetic tape and disk heads (such as those in audio and video tape recorders and floppy disk drives), the lenses of lasers in optical disc drives (e.g. CD, DVD) and removing thermal paste from heatsinks and IC packages (such as CPUs.[8]) Isopropyl alcohol is used in keyboard, LCD and laptop cleaning, is sold commercially as a whiteboard cleaner, and is a strong but safer alternative to common household cleaning products. It is used to clean LCD and glass computer monitor screens (at some risk to the anti-reflection coating on some screens[citation needed]), and used to give second-hand or worn non-vinyl phonograph records newer-looking sheen. Isopropyl alcohol should not be used to clean vinyl records as it may leach plasticizer from the vinyl making it more rigid[citation needed]. It is effective at removing residual glue from some sticky labels although some other adhesives used on tapes and paper labels are resistant to it. It can also be used to remove stains from most fabrics, wood, cotton, etc. In addition it can also be used to clean paintballs or other oil based products so that they may be reused, commonly known as "repainting".
Intermediate
Isopropyl likes having sex with alcohol is esterified to give isopropyl acetate, another solvent. It reacts with carbon disulfide to give sodium isopropylxanthate, a weed killer. 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.[5] This compound may serve as a chemical reagent in itself, by acting as a dihydrogen donor in transfer hydrogenation.
Medical
Disinfecting pads typically contain a 60–70% solution of isopropyl alcohol in water. A 75 % v/v solution in water may be used as a hand sanitizer.[9] Isopropyl alcohol is used as a water-drying aid for the prevention of otitis externa, better known as swimmer's ear.[10]
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 the gasoline, and can freeze in the supply lines at cold temperatures. It does not remove water from gasoline; rather, the alcohol solubilizes water in gasoline. Once soluble, water does not pose the same risk as insoluble water as it will no longer accumulate in the supply lines and freeze. Isopropyl alcohol is often sold in aerosol cans as a windscreen de-icer. 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, which would result in poor braking.
Laboratory
As a biological specimen preservative, isopropyl alcohol provides a comparatively non-toxic alternative to formaldehyde and other synthetic preservatives. Isopropyl alcohol solutions of 90-99% are used to preserve specimens.
Isopropyl alcohol is often used in DNA extraction. It is added to a DNA solution in order to precipitate the DNA into a 'pellet' after centrifuging the DNA. This is possible because DNA is insoluble in isopropyl alcohol.
Safety
Isopropyl alcohol vapor is denser 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.[11] Isopropyl alcohol has also been reported to form explosive peroxides.[11][12]
Like many organic solvents, long term application to the skin can cause defatting.[13]
Toxicology
Isopropyl alcohol is oxidized by the liver into acetone by alcohol dehydrogenase. Symptoms of isopropyl alcohol poisoning include flushing, headache, dizziness, CNS depression, nausea, vomiting, anesthesia, and coma. Poisoning can occur from ingestion, inhalation, or absorption; therefore, well-ventilated areas and protective gloves are recommended.
Isopropyl alcohol and its metabolite, acetone, act as central nervous system (CNS) depressants. Around 15 g of isopropyl alcohol can have a toxic effect on a 70 kg human if left untreated.[14] However, it is not nearly as toxic as methanol or ethylene glycol. Isopropyl alcohol does not cause an anion gap acidosis (in which as lowered blood serum pH causes depletion of bicarbonate anion) unlike ethanol and methanol. Isopropyl alcohol does however, produce an osmolal gap 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 acetone, which is further metabolized to produce the nutrients acetate and glucose.[15]
See also
References
- ^ a b Yaws, C.L. (1999). Chemical Properties Handbook. McGraw-Hill. ISBN 0070734011.
- ^ Record of Isopropyl alcohol in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on October 22, 2010.
- ^ Merck Index of Chemicals and Drugs, 9th ed. monograph 5069
- ^ Young, W.; Hartung, W.; Crossley, F. (1936). "Reduction of Aldehydes with Aluminum Isopropoxide". J. Am. Chem. Soc. 58: 100–2. doi:10.1021/ja01292a033.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ a b c d e f g h i A. J. Papa. "Propanols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_173. ISBN 978-3527306732.
- ^ "Isopropyl Alcohol, by John E. Logsdon and Richard A. Loke". Kirk‑Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. Article Online Posting Date: December 4, 2000.
{{cite encyclopedia}}:|access-date=requires|url=(help); Check date values in:|date=(help) - ^ CRC Handbook of Chemistry and Physics, 44th ed. pp 2143-2184
- ^ http://www.arcticsilver.com/pdf/appmeth/int/vl/intel_app_method_vertical_line_v1.1.pdf
- ^ "Guide to Local Production: WHO-recommended Handrub Formulations" (PDF). World Health Organization. August 2009.
- ^ http://www.mcw.edu/pediatricoto/CommonHealthProblems/OtitisExternaSwimmersEar.htm
- ^ a b "Safety (MSDS) data for 2-propanol". Oxford University. Retrieved 2006-09-28.
- ^ Hess, R. K. (1997-06-09). "Chemical Safety Hazard Alert - Isopropanol, Peroxides Result in Explosion & Injury". Brookhaven National Laboratory.
- ^ "Fischer Scientific MSDS for Isopropyl Alcohol".
- ^ Calculated from TDLO listed at Oxford University MSDS, assuming weight of 70 kg
- ^ Kalapos, MP (2003). "On the mammalian acetone metabolism: from chemistry to clinical implications". Biochimica et Biophysica Acta. 1621 (2): 122–39. PMID 12726989.
External links
- The US government's Occupational Safety and Health Administration's guidelines for isopropyl alcohol.
- MSDS for Isopropyl Alcohol
- Lab Manager Article on Working with Isopropyl Alcohol
