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citation needed 12 000 ppm rat 8 h 8 lc lo lowest published 16 000 ppm rat 4 h 12 800 ppm mouse 3 h 8 niosh us health exposure limits pel permissible twa 400 ppm 980 mg m 3 7 rel recommended twa 400 ppm 980 mg m 3 st 500 ppm 1225 mg m 3 7 idlh immediate danger 2000 ppm 7 safety data sheet sds 1 related compounds related alcohols 1 propanol ethanol 2 butanol related compounds acetone 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 y verify what is y n infobox references chemical compound isopropyl alcohol iupac name propan 2 ol and also called isopropanol or 2 propanol commonly abbreviated as ipa is a colorless flammable organic compound with a pungent odor 9 10 isopropyl alcohol an organic polar molecule is miscible in water ethanol and chloroform demonstrating its ability to dissolve a wide range of substances including ethyl cellulose polyvinyl butyral oils alkaloids and natural resins notably it is not miscible with salt solutions and can be separated by adding sodium chloride in a process known as salting out it forms an azeotrope with water resulting in a boiling point of 80 37 c and is characterized by its slightly bitter taste isopropyl alcohol becomes viscous at lower temperatures freezing at 89 5 c and has significant ultraviolet visible absorbance at 205 nm chemically it can be oxidized to acetone or undergo various reactions to form compounds such as isopropoxides e g aluminium isopropoxide as an isopropyl group linked to a hydroxyl group chemical formula ch 3 2 choh 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 propan 1 ol and ethyl methyl ether all of which share the formula c 3 h 8 o it was first synthesized in 1853 by alexander william williamson and later produced for cordite preparation it is produced through hydration of propene or hydrogenation of acetone with modern processes achieving anhydrous alcohol through azeotropic distillation isopropyl alcohol serves in medical settings as a rubbing alcohol and hand sanitizer and in industrial and household applications as a solvent it is a common ingredient in products such as antiseptics disinfectants and detergents more than a million tonnes are produced worldwide annually isopropyl alcohol poses safety risks due to its flammability and potential for peroxide formation its ingestion or absorption leads to toxic effects including central nervous system depression and coma properties edit isopropyl alcohol is miscible in water ethanol and chloroform as it is an organic polar molecule it dissolves ethyl cellulose polyvinyl butyral many oils alkaloids and natural resins 11 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 12 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 by mass 91 by volume isopropyl alcohol it has a slightly bitter taste and is toxic when ingested 12 13 isopropyl alcohol becomes increasingly viscous with decreasing temperature and freezes at 89 5 c 129 1 f 9 mixtures with water have higher freezing points 99 at 89 5 c 129 1 f 91 the azeotrope at 75 5 c 103 9 f and 70 at 61 7 c 79 1 f 14 isopropyl alcohol has a maximal absorbance at 205 nm in an ultraviolet visible spectrum 15 16 reactions edit 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 ch 3 2 choh ch 3 2 co h 2 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 are called isopropoxides with titanium tetrachloride isopropyl alcohol reacts to give titanium isopropoxide ticl 4 4 ch 3 2 choh ti och ch 3 2 4 4 hcl this and similar reactions are often conducted in the presence of base the reaction with aluminium is initiated by a trace of mercury to give aluminium isopropoxide 17 history edit isopropyl alcohol was first synthesized by the chemist alexander william williamson in 1853 he achieved this by heating a mixture of propene and sulfuric acid standard oil produced isopropyl alcohol by hydrating propene isopropyl alcohol was oxidized to acetone for the preparation of cordite a smokeless low explosive propellant 18 production edit in 1994 1 5 million tonnes of isopropyl alcohol were produced in the united states europe and japan 19 it is primarily produced by combining water and propene in a hydration reaction or by hydrogenating acetone 19 20 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 mass isopropyl alcohol and 12 1 by mass water 21 pure anhydrous isopropyl alcohol is made by azeotropic distillation of the wet isopropyl alcohol using either diisopropyl ether or cyclohexane as azeotroping agents 19 biological edit small amounts of isopropyl alcohol are produced in the body in diabetic ketoacidosis 22 indirect hydration edit 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 19 ch 3 ch ch 2 h 2 o h 2 so 4 ch 3 2 choh direct hydration edit see also heteropoly acid direct hydration reacts propene and water either in gas or liquid phase at high pressures in the presence of solid or supported acidic catalysts this type of process usually requires higher purity propylene 90 19 direct hydration is more commonly used in europe hydrogenation of acetone edit isopropyl alcohol can be prepared via the hydrogenation of acetone but this approach involves an extra step compared to the above methods as acetone is itself normally prepared from propene via the cumene process 19 ipa cost is primarily driven by raw material cost and this way is economical when acetone is cheaper than propylene as a byproduct of phenol 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 was one of the original industrial catalysts modern catalysts are often supported bimetallic materials uses edit one of the small scale uses of isopropyl alcohol is in cloud chambers isopropyl alcohol 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 tonnes were used for household purposes and in personal care products isopropyl alcohol is popular in particular for pharmaceutical applications 19 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 19 solvent edit isopropyl alcohol dissolves a wide range of non polar compounds it evaporates quickly and the typically available grades tend not to leave behind oil traces when used as a cleaning fluid unlike some other common solvents citation needed 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 ethanol n butanol and methanol it belongs to the group of alcohol solvents isopropyl alcohol is commonly used for cleaning eyeglasses electrical contacts audio or video tape heads dvd and other optical disc lenses bongs 23 and for removing thermal paste from heatsinks on cpus 24 and other ic packages it is sometimes used by miniatures hobbyists to strip acrylic paints primers from high impact polystyrene miniatures 25 26 27 intermediate edit isopropyl alcohol is esterified to give isopropyl acetate another solvent it reacts with carbon disulfide and sodium hydroxide to give sodium isopropylxanthate which has use as an herbicide and an ore flotation reagent 28 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 19 this compound may serve as a chemical reagent in itself by acting as a dihydrogen donor in transfer hydrogenation medical edit 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 29 isopropyl alcohol is used as a water drying aid for the prevention of otitis externa better known as swimmer s ear 30 inhaled isopropyl alcohol can be used for treating nausea in some settings by placing a disinfecting pad under the nose 31 early uses as an anesthetic edit 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 32 or as an anesthetic by inhaling the fumes or orally early uses included using the solvent as general anesthetic for small mammals 33 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 edit 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 dissolved within 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 edit 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 semiconductors edit isopropyl alcohol is used as an additive in alkaline anisotropic etching of monocrystalline silicon such as with potassium hydroxide or tetramethylammonium hydroxide this process is used in texturing of silicon solar cells and microfabrication e g in mems devices isopropyl alcohol increases the anisotropy of the etch by increasing the etch rate of 100 plane relative to higher indexed planes 34 safety edit 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 sparks and open flame 35 distillation of isopropyl alcohol over magnesium has been reported to form peroxides which may explode upon concentration 36 37 isopropyl alcohol can react with air and oxygen over time to form unstable peroxides that can explode 38 toxicology edit isopropyl alcohol via its metabolites is somewhat more toxic than ethanol but considerably less toxic than ethylene glycol or methanol death from ingestion or absorption of even relatively large quantities is rare both isopropyl alcohol and its metabolite acetone act as central nervous system cns depressants 39 poisoning can occur from ingestion inhalation or skin absorption 40 symptoms of isopropyl alcohol poisoning include flushing headache dizziness cns depression nausea vomiting anesthesia hypothermia low blood pressure shock respiratory depression and coma 39 overdoses may cause a fruity odor on the breath as a result of its metabolism to acetone 41 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 39 the findings of acetone without acidosis leads to the sine qua non of ketosis without acidosis isopropyl alcohol is oxidized to form acetone by alcohol dehydrogenase in the liver 39 and has a biological half life in humans between 2 5 and 8 0 hours 39 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 42 in forensic pathology people who have died as a result of diabetic ketoacidosis or alcoholic ketoacidosis 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 22 references edit alcohols rule c 201 1 nomenclature of organic chemistry the iupac blue book sections a b c 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 ter...
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