関: 1-propanol、propanol

WordNet

the 14th letter of the Roman alphabet (同)n
a clear colorless volatile liquid (alcohol) used as a solvent and antiseptic (同)propyl alcohol

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nitrogenの化学記号

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/16 14:12:46」(JST)

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1-Propanol, is a primary alcohol with the formula CH₃CH₂CH₂OH. 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.

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 indeed 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.

External links

International Chemical Safety Card 0553
NIOSH Pocket Guide to Chemical Hazards

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リンク元	「n-プロパノール」「1-propanol」
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「n-プロパノール」

1-Propanol
Names
	IUPAC name Propan-1-ol
	Other names n-Propyl alcohol; n-Propanol; n-PrOH; Ethylcarbinol; 1-Hydroxypropane; Propionic alcohol; Propionyl alcohol; Propionylol; Propyl alcohol; Propylic alcohol; Propylol;
Identifiers
CAS Registry Number	71-23-8
3DMet	B00883
ATC code	D08AX03
Beilstein Reference	1098242
ChEBI	CHEBI:28831
ChEMBL	ChEMBL14687
ChemSpider	1004
DrugBank	DB03175
EC number	200-746-9
Gmelin Reference	25616
	InChI InChI=1S/C3H8O/c1-2-3-4/h4H,2-3H2,1H3 ; Key: BDERNNFJNOPAEC-UHFFFAOYSA-N ;
Jmol-3D images	Image
KEGG	C05979
MeSH	1-Propanol
PubChem	1031
RTECS number	UH8225000
	SMILES CCCO ;
UNII	96F264O9SV
UN number	1274
Properties
Chemical formula	C3H8O
Molar mass	60.10 g·mol−1
Appearance	Colorless liquid
Odor	mild, alcohol-like
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
Solubility in water	miscible
log P	0.329
Vapor pressure	1.99 kPa (at 20 °C)
Acidity (pKa)	16
Basicity (pKb)	−2
Refractive index (nD)	1.387
Viscosity	1.959 mPa×s (at 25 °C)
Dipole moment	1.68 D
Thermochemistry
Specific; heat capacity (C)	143.96 J K−1 mol−1
Std molar; entropy (So298)	192.8 J K−1 mol−1
Std enthalpy of; formation (ΔfHo298)	−302.79–−302.29 kJ mol−1
Std enthalpy of; combustion (ΔcHo298)	−2.02156–−2.02106 MJ mol−1
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H225, H318, H336
GHS precautionary statements	P210, P261, P280, P305+351+338
EU classification	F Xi
R-phrases	R11, R41, R67
S-phrases	(S2), S7, S16, S24, S26, S39
NFPA 704	3 1 0
Flash point	22 °C (72 °F; 295 K)
Autoignition; temperature	371 °C (700 °F; 644 K)
Explosive limits	2.2% - 13.7%
	Lethal dose or concentration (LD, LC):
LD50 (Median dose)	2800 mg/kg (rabbit, oral); 6800 mg/kg (mouse, oral); 1870 mg/kg (rat, oral)
	US health exposure limits (NIOSH):
PEL (Permissible)	TWA 200 ppm (500 mg/m3)
REL (Recommended)	TWA 200 ppm (500 mg/m3) ST 250 ppm (625 mg/m3) [skin]
IDLH (Immediate danger	800 ppm
Related compounds
Related compounds	Butane; Propanamine; Ethanol; Butanol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references