1-Propanol

1-Propanol

Skeletal formula of 1-propanol
Ball and stick model of 1-propanol
Names
Pronunciation	ˈprəʊpən.wən.ɒl
Preferred IUPAC name Propan-1-ol [1]
Other names n-Propyl alcohol n-Propanol n-PrOH Ethyl carbinol 1-Hydroxypropane Propionic alcohol Propionyl alcohol Propionylol Propyl alcohol Propylic alcohol Propylol
Identifiers
CAS Number	71-23-8  Y
3D model (JSmol)	Interactive image
Beilstein Reference	1098242
ChEBI	CHEBI:28831  Y
ChEMBL	ChEMBL14687  Y
ChemSpider	1004  Y
DrugBank	DB03175  Y
ECHA InfoCard	100.000.679
EC Number	200-746-9
Gmelin Reference	25616
KEGG	C05979  Y
MeSH	1-Propanol
PubChem CID	1031
RTECS number	UH8225000
UNII	96F264O9SV  Y
UN number	1274
CompTox Dashboard (EPA)	DTXSID2021739
InChI InChI=1S/C3H7OH/c1-2-3-4/h4H,2-3H2,1H3 Y Key: BDERNNFJNOPAEC-UHFFFAOYSA-N Y
SMILES CCCO
Properties
Chemical formula	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
Solubility in water	miscible
log P	0.329
Vapor pressure	1.99 kPa (at 20 °C)
Acidity (pKa)	16
Basicity (pKb)	−2
Magnetic susceptibility (χ)	−45.176·10−6 cm3/mol
Refractive index (nD)	1.387
Viscosity	1.959 mPa·s (at 25 °C) [3]
Dipole moment	1.68 D
Thermochemistry
Heat capacity (C)	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
ATC code	D08AX03 ( WHO )
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Flammable liquid
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H318, H336
Precautionary statements	P210, P261, P280, P305+P351+P338
NFPA 704 (fire diamond)	1 3 0
Flash point	22 °C (72 °F; 295 K)
Autoignition temperature	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 their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

1-Propanol (also propan-1-ol, propanol, n-propyl alcohol) is a primary alcohol with the formula CH₃CH₂CH₂OH and sometimes represented as PrOH or n-PrOH. It is a colourless liquid and an isomer of 2-propanol. 1-Propanol is used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.

History

The compound was discovered by Gustave Chancel in 1853 by fractional distillation of fusel oil. He measured its boiling point at 96°C, correctly identified its empirical formula, studied some of its chemical properties and gave it two names: propionic alcohol and hydrate of trityl. ^{[5] [6]}

After several unsuccessful attempts, it was synthesized independently and by two different routes by Eduard Linnemann and Carl Schorlemmer in 1868. ^{[7] [8] [9]}

Occurrence

Fusel alcohols like 1-Propanol are grain fermentation byproducts, and therefore trace amounts of 1-Propanol are present in many alcoholic beverages.

Chemical properties

Some example reactions of 1-propanol

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 n-propyl chloride. 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 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. Propionaldehyde is 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. ^[10]

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.

Safety

1-Propanol is thought to be similar to ethanol 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 into propionic acid. Effects include alcoholic intoxication and high anion gap metabolic acidosis. As of 2011, one case of lethal poisoning was reported following oral ingestion of 500mL of 1-propanol. ^[11] Due to a lack of long term data, the carcinogenicity of 1-propanol in humans is unknown.

1-Propanol as fuel

1-Propanol has a high octane number and is suitable for use as engine fuel. However, propanol is too expensive to use as a motor fuel. The research octane number (RON) of propanol is 118, and the anti-knock index (AKI) is 108. ^[12]

References

1. Favre HA, Powell WH (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. p. 61. doi:10.1039/9781849733069. ISBN   9780854041824.
2. NIOSH Pocket Guide to Chemical Hazards. "#0533". National Institute for Occupational Safety and Health (NIOSH).
3. Pal A, Gaba R (2008). "Volumetric, acoustic, and viscometric studies of molecular interactions in binary mixtures of dipropylene glycol dimethyl ether with 1-alkanols at 298.15 K". J. Chem. Thermodyn. 40 (5): 818–828. doi:10.1016/j.jct.2008.01.008.
4. "n-Propyl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
5. Wisniak, Jaime (2013). "Gustav Charles Bonaventure Chancel". Educación Química. 24 (1): 23–30. doi: 10.1016/S0187-893X(13)73191-4 . ISSN   0187-893X.
6. s:fr:Page:Comptes rendus hebdomadaires des séances de l’Académie des sciences, tome 037, 1853.djvu/414
7. Linnemann, Eduard (1868). "Ueber die Darstellung der Fettalkohole aus ihren Anfangsgliedern. Reduction des Essigsäure-Anhydrids zu Aethylalkohol". Justus Liebigs Annalen der Chemie (in German). 148 (2): 249–251. doi:10.1002/jlac.18681480216. ISSN   1099-0690.
8. Zeitschrift für Chemie (in German). Quandt & Händel. 1868.
9. Schorlemmer, C. (1869). "On the Derivatives of Propane (Hydride of Propyl)". Proceedings of the Royal Society of London. 17: 372–376. doi:10.1098/rspl.1868.0072. ISSN   0370-1662.
10. Papa AJ (2011). "Propanols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_173.pub2. ISBN   9783527303854.
11. Unmack JL (2011). "N-PROPANOL Health-Base Assessment and Recommendation for HEAC" (PDF).
12. "Bioalcohols". Biofuel.org.uk. 2010. Retrieved 16 Apr 2014.

Further reading

1. 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
2. Lide DR, ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). TF-CRC. ISBN   0849304873.
3. O'Neil MJ, ed. (2006). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (14th ed.). Merck. ISBN   091191000X.
4. Perkin WH, Kipping FS (1922). Organic Chemistry. London: W. & R. Chambers. ISBN   0080223540.

External links

• International Chemical Safety Card 0553
• NIOSH Pocket Guide to Chemical Hazards