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 | |
| Names | |
|---|---|
| Pronunciation | /ˈprəʊpən.wən.ɒl/ |
| Preferred IUPAC name Propan-1-ol[1] | |
Other names
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| Identifiers | |
| |
3D model (JSmol) | |
| 1098242 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
|
| DrugBank |
|
| ECHA InfoCard | 100.000.679 |
| EC Number |
|
| 25616 | |
| KEGG |
|
| MeSH | 1-Propanol |
| RTECS number |
|
| UNII | |
| UN number | 1274 |
| |
| |
| Properties | |
| C3H8O | |
| Molar mass | 60.096 g·mol−1 |
| Appearance | Colorless liquid |
| Odor | mild, alcohol-like[2] |
| Density | 0.803 g/mL |
| Melting point | −126 °C; −195 °F; 147 K |
| Boiling point | 97 to 98 °C; 206 to 208 °F; 370 to 371 K |
| miscible | |
| logP | 0.329 |
| Vapor pressure | 1.99 kPa (at 20 °C) |
| Acidity (pKa) | 16 |
| Basicity (pKb) | −2 |
| −45.176·10−6 cm3/mol | |
Refractive index (nD) | 1.387 |
| Viscosity | 1.959 mPa·s (at 25 °C)[3] |
| 1.68 D | |
| Thermochemistry | |
| 143.96 J/(K·mol) | |
Std molar entropy(S⦵298) | 192.8 J/(K·mol) |
Std enthalpy of formation(ΔfH⦵298) | −302.79…−302.29 kJ/mol |
Std enthalpy of combustion(ΔcH⦵298) | −2.02156…−2.02106 MJ/mol |
| Pharmacology | |
| D08AX03 (WHO) | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | Flammable liquid |
| GHS labelling: | |
  | |
| Danger | |
| H225,H302,H318,H336 | |
| P210,P261,P280,P305+P351+P338 | |
| NFPA 704 (fire diamond) | |
| Flash point | 22 °C (72 °F; 295 K) |
| 371 °C (700 °F; 644 K) | |
| Explosive limits | 2.2–13.7%[2] |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 2800 mg/kg (rabbit, oral) 1699 mg/kg (mouse, oral) 1870 mg/kg (rat, oral)[4] |
| NIOSH (US health exposure limits): | |
PEL (Permissible) | TWA 200 ppm (500 mg/m3)[2] |
REL (Recommended) | TWA 200 ppm (500 mg/m3) ST 250 ppm (625 mg/m3) [skin][2] |
IDLH (Immediate danger) | 800 ppm[2] |
| Related compounds | |
Related compounds | Propane Isopropyl alcohol Propanamine Ethanol Butanol |
| Supplementary data page | |
| 1-Propanol (data page) | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
1-Propanol (alsopropan-1-ol,propanol,n-propyl alcohol) is aprimary alcohol with the formulaCH3CH2CH2OH and sometimesrepresented asPrOH orn-PrOH. It is a colourless liquid and anisomer of2-propanol. 1-Propanol is used as asolvent in the pharmaceutical industry, mainly forresins andcellulose esters, and, sometimes, as adisinfecting agent.
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The compound was discovered byGustave Chancel in 1853 byfractional distillation offusel oil.[5] He measured its boiling point at 96°C, correctly identified itsempirical formula, studied some of its chemical properties and gave it two names:propionic alcohol andhydrate of trityl.[6][7]
After several unsuccessful attempts, it was synthesized independently and by two different routes byEduard Linnemann andCarl Schorlemmer in 1868.[8][9][10]
Fusel alcohols like 1-Propanol are grain fermentation byproducts, and therefore trace amounts of 1-Propanol are present inmany alcoholic beverages.
1-Propanol shows the normal reactions of aprimary alcohol. Thus it can be converted toalkyl halides; for example redphosphorus andiodine producen-propyl iodide in 80% yield, whilePCl3 with catalyticZnCl2 givesn-propyl chloride. Reaction withacetic acid in the presence of anH2SO4 catalyst underFischer esterification conditions givespropyl acetate, while refluxing propanol overnight with formic acid alone can produce propyl formate in 65% yield.
Oxidation of 1-propanol withNa2Cr2O7 andH2SO4 gives a 36% yield ofpropionaldehyde, and therefore for this type of reaction higher yielding methods usingPCC or theSwern oxidation are recommended. Oxidation withchromic acid yieldspropionic acid.
1-Propanol is manufactured by catalytichydrogenation ofpropionaldehyde. Propionaldehyde is produced via theoxo process byhydroformylation ofethylene usingcarbon monoxide andhydrogen in the presence of a catalyst such ascobalt octacarbonyl or arhodium complex.[11]
A traditional laboratory preparation of 1-propanol involves treatingn-propyl iodide with moistAg2O.
1-Propanol is thought to be similar toethanol in its effects on the human body, but 2 to 4 times more potent according to a study conducted on rabbits. Many toxicology studies find oral acute LD50 ranging from 1.9 g/kg to 6.5 g/kg (compared to 7.06 g/kg for ethanol). It is metabolized intopropionic acid. Effects includealcoholic intoxication andhigh anion gap metabolic acidosis. As of 2011, one case of lethal poisoning was reported following oral ingestion of 500mL of 1-propanol.[12] Due to a lack of long term data, the carcinogenicity of 1-propanol in humans is unknown.
1-Propanol has a highoctane number and is suitable for use asengine fuel. However, propanol is too expensive to use as a motor fuel. Theresearch octane number (RON) of propanol is 118, and theanti-knock index (AKI) is 108.[13]
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