1-Propanol

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
3DMet	B00883
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, water-miscible liquid. It is an isomer of 2-propanol. 1-Propanol is used as a solvent.

History

1-Propanol was first discovered in 1853 by the French chemist Marcellin Berthelot through the hydrolysis of propyl chloride.^[5] Since then, it has been extensively studied and utilized in various fields.

Recently, the discovery of n-propanol in the interstellar medium (ISM) has garnered significant attention. Researchers detected both conformers of n-propanol (Ga-n-C3H7OH and Aa-n-C3H7OH) in the Giant Molecular Cloud G+0.693-0.027 located in the Galactic Center.^[6][7] The derived column densities of n-propanol are (5.5±0.4)×10^13 cm^-2 for the Ga conformer and (3.4±0.3)×10^13 cm^-2 for the Aa conformer, which imply molecular abundances of (4.1±0.3)×10^-10 for Ga-n-C3H7OH and of (2.5±0.2)×10^-10 for Aa-n-C3H7OH^[7]

Occurrence

Fusel alcohols like 1-Propanol are grain fermentation byproducts, and therefore trace amounts of 1-Propanol are present in many alcoholic beverages. Propanol has been detected in the interstellar medium.^[8]

Reactions

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, 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. When treated with formic acid it converts to propyl formate. Oxidation of 1-propanol with Na₂Cr₂O₇ and H₂SO₄ gives propionaldehyde, as does PCC and the Swern oxidation. 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.^[9]

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.

Applications

1-Propanol, also known as n-propanol or propyl alcohol, is a colorless, flammable liquid with a distinct odor. It is an important organic compound with the chemical formula CH3CH2CH2OH. 1-Propanol finds extensive applications across various industries due to its unique properties and versatility.

Solvent Applications

One of the primary uses of 1-propanol is as a solvent in the production of cosmetics, pharmaceuticals, and food additives.^[10] Its excellent solvent properties make it suitable for dissolving a wide range of organic compounds. In the cosmetics industry, 1-propanol is used in the formulation of perfumes, lotions, and other personal care products.^[10] It helps to dissolve essential oils, fragrances, and other ingredients, ensuring a homogeneous mixture.

Chemical Intermediate

1-Propanol is an important chemical intermediate in the synthesis of various organic compounds.^[10] It serves as a raw material for the production of propyl acetate, which is widely used as a solvent in the paint and coatings industry.^[10] Propyl acetate is known for its fast evaporation rate and excellent solvency, making it suitable for use in quick-drying paints and lacquers.

Another important derivative of 1-propanol is propyl amine, which is used in the production of pesticides, herbicides, and other agricultural chemicals.^[10] Propyl amine is also used as a corrosion inhibitor in the oil and gas industry, helping to protect pipelines and equipment from corrosion damage.

Antiseptic Properties

Due to its antimicrobial properties, 1-propanol is commonly used in hand sanitizers and disinfectants.^[10] It is effective against a wide range of bacteria, viruses, and fungi, making it a valuable ingredient in products designed to prevent the spread of infections. 1-Propanol works by denaturing proteins and disrupting the cell membranes of microorganisms, leading to their inactivation.

In healthcare settings, 1-propanol-based hand sanitizers are widely used by healthcare professionals to maintain hand hygiene and reduce the risk of hospital-acquired infections.^[11] The rapid evaporation and non-sticky nature of 1-propanol make it a preferred choice for hand sanitizers compared to other alcohols like ethanol or isopropanol.

Safety

1-Propanol is thought to be similar to ethanol in its effects on the human body, but 2–4 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.^[12] Due to lack of long term data, the carcinogenicity of 1-propanol in human beings is unknown.

Uses

1-Propanol is mainly used as a solvent, e.g., for inks, resins, and cellulose esters. It is a precursor to more specialized solvents such as glycol monopropyl ether and propyl propionate that are of commercial interest.^[9] It is sometimes used as a disinfecting agent.

1-Propanol has high octane number and would be suitable as a motor fuel, but it is too expensive. The research octane number of propanol is 118, and anti-knock index is 108.^[13]

References

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