1-Propanol

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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
3D model (
JSmol
)
3DMet
1098242
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.000.679 Edit this at Wikidata
EC Number
  • 200-746-9
25616
KEGG
MeSH 1-Propanol
RTECS number
  • UH8225000
UNII
UN number 1274
  • InChI=1S/C3H7OH/c1-2-3-4/h4H,2-3H2,1H3 checkY
    Key: BDERNNFJNOPAEC-UHFFFAOYSA-N checkY
  • CCCO
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
log P 0.329
Vapor pressure 1.99 kPa (at 20 °C)
Acidity (pKa) 16
Basicity (pKb) −2
−45.176·10−6 cm3/mol
1.387
Viscosity 1.959 mPa·s (at 25 °C) [3]
1.68 D
Thermochemistry
143.96 J/(K·mol)
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:
GHS02: Flammable GHS07: Exclamation mark
Danger
H225, H302, H318, H336
P210, P261, P280, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
3
0
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):
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
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 checkY☒N ?)

1-Propanol (also propan-1-ol, propanol, n-propyl alcohol) is a

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

Some example reactions of 1-propanol

1-Propanol shows the normal reactions of a

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

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

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,

propyl propionate that are of commercial interest.[9] It is sometimes used as a disinfecting
agent.

1-Propanol has high

anti-knock index is 108.[13]

References

  1. ISBN 9780854041824
    .
  2. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0533". National Institute for Occupational Safety and Health (NIOSH).
  3. 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. ISSN 0031-9104
    .
  6. PMID 35495658
    .
  7. ^
    ISSN 0004-6361
    .
  8. ISSN 0004-6361
    .
  9. ^ a b Papa AJ (2011). "Propanols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.
    ISBN 9783527303854
    .
  10. ^
    ISSN 0959-3993
    .
  11. PMID 21116645
    .
  12. ^ Unmack JL (2011). "N-Propanol Health-Base Assessment and Recommendation for HEAC" (PDF).
  13. ^ "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
Retrieved from "https://en.wikipedia.org/w/index.php?title=1-Propanol&oldid=1219549972"