WordNet
- a clear colorless volatile liquid (alcohol) used as a solvent and antiseptic (同)propyl alcohol
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/02/13 19:30:21」(JST)
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| Names | |
|---|---|
| IUPAC name
Propan-1-ol[1]
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Other names
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| Identifiers | |
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CAS Number
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71-23-8 Y |
| 3D model (Jmol) | Interactive image |
| 3DMet | B00883 |
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Beilstein Reference
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1098242 |
| ChEBI | CHEBI:28831 Y |
| ChEMBL | ChEMBL14687 Y |
| ChemSpider | 1004 Y |
| DrugBank | DB03175 Y |
| ECHA InfoCard | 100.000.679 |
| EC Number | 200-746-9 |
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Gmelin Reference
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25616 |
| KEGG | C05979 N |
| MeSH | 1-Propanol |
| PubChem | 1031 |
| RTECS number | UH8225000 |
| UNII | 96F264O9SV Y |
| UN number | 1274 |
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InChI
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SMILES
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| Properties | |
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Chemical formula
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C3H8O |
| Molar mass | 60.10 g·mol−1 |
| Appearance | Colorless liquid |
| Odor | mild, alcohol-like[2] |
| Density | .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 |
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Solubility in water
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miscible |
| log P | 0.329 |
| Vapor pressure | 1.99 kPa (at 20 °C) |
| Acidity (pKa) | 16 |
| Basicity (pKb) | −2 |
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Magnetic susceptibility (χ)
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-45.176·10−6 cm3/mol |
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Refractive index (nD)
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1.387 |
| Viscosity | 1.959 mPa·s (at 25 °C) [3] |
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Dipole moment
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1.68 D |
| Thermochemistry | |
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Specific
heat capacity (C) |
143.96 J K−1 mol−1 |
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Std molar
entropy (S |
192.8 J K−1 mol−1 |
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Std enthalpy of
formation (ΔfH |
−302.79–−302.29 kJ mol−1 |
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Std enthalpy of
combustion (ΔcH |
−2.02156–−2.02106 MJ mol−1 |
| Pharmacology | |
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ATC code
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D08AX03 (WHO) |
| Hazards | |
| GHS pictograms | |
| GHS signal word | DANGER |
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GHS hazard statements
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H225, H318, H336 |
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GHS precautionary statements
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P210, P261, P280, P305+351+338 |
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EU classification (DSD)
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F Xi |
| R-phrases | R11, R41, R67 |
| S-phrases | (S2), S7, S16, S24, S26, S39 |
| NFPA 704 |
3
1
0
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| Flash point | 22 °C (72 °F; 295 K) |
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Autoignition
temperature |
371 °C (700 °F; 644 K) |
| Explosive limits | 2.2% - 13.7%[2] |
| Lethal dose or concentration (LD, LC): | |
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LD50 (median dose)
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2800 mg/kg (rabbit, oral) 6800 mg/kg (mouse, oral) |
| US health exposure limits (NIOSH): | |
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PEL (Permissible)
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TWA 200 ppm (500 mg/m3)[2] |
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REL (Recommended)
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TWA 200 ppm (500 mg/m3) ST 250 ppm (625 mg/m3) [skin][2] |
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IDLH (Immediate danger)
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800 ppm[2] |
| Related compounds | |
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Related compounds
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Butane Propanamine |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| N verify (what is YN ?) | |
| Infobox references | |
1-Propanol, is a primary alcohol with the formula CH3CH2CH2OH (sometimes represented as PrOH or n-PrOH). This colorless liquid is also known as propan-1-ol, 1-propyl alcohol, n-propyl alcohol, and n-propanol. It is an isomer of isopropanol (2-propanol, isopropyl alcohol). 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.
Contents
- 1 Chemical properties
- 2 Preparation
- 3 Safety
- 3.1 Inhalation
- 4 Propanol as fuel
- 5 References
- 6 Further reading
- 7 External links
Chemical properties
1-Propanol shows the normal reactions of a primary alcohol. Thus it can be converted to alkyl halides; for example red phosphorus and iodine produce n-propyl iodide in 80% yield, while PCl3 with catalytic ZnCl2 gives 1-chloropropane. Reaction with acetic acid in the presence of an H2SO4 catalyst under Fischer esterification conditions gives propyl acetate, while refluxing propanol overnight with formic acid alone can produce propyl formate in 65% yield. Oxidation of 1-propanol with Na2Cr2O7 and H2SO4 gives only a 36% yield of propionaldehyde, and therefore for this type of reaction higher yielding methods using PCC or the Swern oxidation are recommended. Oxidation with chromic acid yields propionic acid.
Preparation
1-Propanol is manufactured by catalytic hydrogenation of propionaldehyde. The propionaldehyde is itself produced via the oxo process, by hydroformylation of ethylene using carbon monoxide and hydrogen in the presence of a catalyst such as cobalt octacarbonyl or a rhodium complex.[5]
- H2C=CH2 + CO + H2 → CH3CH2CH=O
- CH3CH2CH=O + H2 → CH3CH2CH2OH
A traditional laboratory preparation of 1-propanol involves treating n-propyl iodide with moist Ag2O.
1-Propanol was discovered in 1853 by Chancel, who obtained it by fractional distillation of fusel oil. Indeed, 1-propanol is a major constituent of fusel oil, a by-product formed from certain amino acids when potatoes or grains are fermented to produce ethanol. This process is no longer a significant source of 1-propanol.
Safety
1-Propanol is thought to be similar to ethanol in its effects on human body, but 2-4 times more potent. Oral LD50 in rats is 1870 mg/kg (compared to 7060 mg/kg for ethanol). It is metabolized into propionic acid. Effects include alcoholic intoxication and high anion gap metabolic acidosis. As of 2011, only one case of lethal 1-propanol poisoning was reported.[6]
Inhalation
Although this method is rare, it does exist. Propanol might be much more convenient than ethanol for inhalation because of its potency with nebulizers.
Propanol as fuel
1-propanol has high octane numbers and it is suitable to engine fuel usage. However, production of propanol has been too expensive to be a common fuel. The research octane number (RON) of propanol is 118 and anti-knock index (AKI) is 108.[7]
References
- ^ "1-Propanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 10 October 2011.
- ^ a b c d e "NIOSH Pocket Guide to Chemical Hazards #0533". National Institute for Occupational Safety and Health (NIOSH).
- ^ Pal, Amalendu; Gaba, Rekha (2008). "Volumetric, acoustic, and viscometric studies of molecular interactions in binary mixtures of dipropylene glycol dimethyl ether with 1-alkanols at 298.15 K". The Journal of Chemical Thermodynamics. 40 (5): 818–828. doi:10.1016/j.jct.2008.01.008.
- ^ "n-Propyl alcohol". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
- ^ Anthony J. Papa "Propanols" in Ullmann’s Encyclopedia of Industrial Chemistry 2011, Wiley-VCH, Weinheim. doi:10.1002/14356007.a22_173.pub2
- ^ "N-PROPANOL Health-Base Assessment and Recommendation for HEAC".
- ^ "Bioalcohols". Biofuel.org.uk. Retrieved 2014-04-16.
Further reading
- Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. (1989), Vogel's Textbook of Practical Organic Chemistry (5th ed.), Harlow: Longman, ISBN 0-582-46236-3
- Lide, David R., ed. (2006-06-26). CRC Handbook of Chemistry and Physics, 87th Edition (87 ed.). TF-CRC. ISBN 0-8493-0487-3.
- Maryadele J. O'Neil, ed. (2006-11-03). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (14 ed.). Merck. ISBN 0-911910-00-X.
- Perkin, W. H.; Kipping, F. S (1922). Organic Chemistry. London: W. & R. Chambers. ISBN 0-08-022354-0.
External links
- International Chemical Safety Card 0553
- NIOSH Pocket Guide to Chemical Hazards
Alcohols
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| Straight-chain primary |
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| Other primary alcohols |
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| Secondary alcohols (2°) |
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| Tertiary alcohols (3°) |
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Antiseptics and disinfectants (D08)
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| Acridine derivatives |
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| Biguanides and amidines |
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| Phenol and derivatives |
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| Nitrofuran derivatives |
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| Iodine products |
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| Quinoline derivatives |
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| Quaternary ammonium compounds |
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| Mercurial products |
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| Silver compounds |
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| Alcohols |
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| Other |
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Hypnotics/sedatives (N05C)
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GABAA receptor positive allosteric modulators
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| Alcohols |
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| Barbiturates |
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| Benzodiazepines |
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| Carbamates |
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| Flavonoids |
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| Imidazoles |
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| Kava constituents |
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| Monoureides |
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| Neuroactive steroids |
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| Nonbenzodiazepines |
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| Phenols |
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| Piperidinediones |
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See also: GABAergics
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UpToDate Contents
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- The fabrication of monolithic capillary column based on poly (bisphenol A epoxy vinyl ester resin-co-ethylene glycol dimethacrylate) and its applications for the separation of small molecules in high performance liquid chromatography.
- Niu W, Wang L, Bai L, Yang G.SourceKey Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding 071002, China.
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- A novel chemoenzymatic synthesis of propyl caffeate using lipase-catalyzed transesterification in ionic liquid.
- Pang N, Gu SS, Wang J, Cui HS, Wang FQ, Liu X, Zhao XY, Wu FA.SourceSchool of Biology and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212018, PR China.
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- NAID 40019513157
- 超臨界CO_2-エントレーナー法による多孔性シリカからのテンプレート剤抽出
- 宇敷 育男,寺谷 彰悟,大田 昌樹,佐藤 善之,猪股 宏
- 化学工学論文集 = Kagaku kogaku ronbunshu 37(5), 512-517, 2011-11-20
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Related Pictures
-1-propanol.svg)
★リンクテーブル★
| リンク元 | 「1-プロパノール」「n-propanol」 |
| 関連記事 | 「propanol」 |
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