1-Propanol

Last updated
1-Propanol
Propan-1-ol.svg
Propan-1-ol-3D-balls.png
Names
Pronunciationˈprəʊpən.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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-746-9
25616
KEGG
MeSH 1-Propanol
PubChem CID
RTECS number
  • UH8225000
UNII
UN number 1274
  • InChI=1S/C3H7OH/c1-2-3-4/h4H,2-3H2,1H3 Yes check.svgY
    Key: BDERNNFJNOPAEC-UHFFFAOYSA-N Yes check.svgY
  • CCCO
Properties
C3H8O
Molar mass 60.096 g·mol−1
AppearanceColorless 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)
Std molar
entropy (S⦵298)
192.8 J/(K·mol)
−302.79…−302.29 kJ/mol
−2.02156…−2.02106 MJ/mol
Pharmacology
D08AX03 ( WHO )
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable liquid
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Danger
H225, H302, H318, H336
P210, P261, P280, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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
 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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 Propanol reactions.png
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, 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]

Related Research Articles

<span class="mw-page-title-main">Alcohol (chemistry)</span> Organic compound with at least one hydroxyl (–OH) group

In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl functional group bound to a saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sugar alcohols and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.

<span class="mw-page-title-main">Ethanol</span> Organic compound (CH₃CH₂OH)

Ethanol is an organic compound with the chemical formula CH3CH2OH. It is an alcohol, with its formula also written as C2H5OH, C2H6O or EtOH, where Et stands for ethyl. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive recreational drug, and the active ingredient in alcoholic drinks.

<span class="mw-page-title-main">Solvent</span> Substance dissolving a solute resulting in a solution

A solvent is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for polar molecules, and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within the cell.

Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4H9OH, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; all are a butyl or isobutyl group linked to a hydroxyl group (sometimes represented as BuOH, 1-BuOH, i-BuOH, and t-BuOH). These are 1-butanol, two stereoisomers of sec-butyl alcohol, isobutanol and tert-butyl alcohol. Butanol is primarily used as a solvent and as an intermediate in chemical synthesis, and may be used as a fuel. Biologically produced butanol is called biobutanol, which may be n-butanol or isobutanol.

<span class="mw-page-title-main">Propylene oxide</span> Chemical compound

Propylene oxide is an acutely toxic and carcinogenic organic compound with the molecular formula C3H6O. This colourless volatile liquid with an odour similar to ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols for use in making polyurethane plastics. It is a chiral epoxide, although it is commonly used as a racemic mixture.

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

<span class="mw-page-title-main">Isobutanol</span> Chemical compound

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

<span class="mw-page-title-main">Allyl alcohol</span> Organic compound (CH2=CHCH2OH)

Allyl alcohol is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers. Allyl alcohol is the smallest representative of the allylic alcohols.

<span class="mw-page-title-main">Propyl acetate</span> Chemical compound

Propyl acetate, also known as propyl ethanoate, is an organic compound. Nearly 20,000 tons are produced annually for use as a solvent. This colorless liquid is known by its characteristic odor of pears. Due to this fact, it is commonly used in fragrances and as a flavor additive. It is formed by the esterification of acetic acid and propan-1-ol, often via Fischer–Speier esterification, with sulfuric acid as a catalyst and water produced as a byproduct.

<span class="mw-page-title-main">Isopropyl acetate</span> Chemical compound

Isopropyl acetate is an ester, an organic compound which is the product of esterification of acetic acid and isopropanol. It is a clear, colorless liquid with a characteristic fruity odor.

<span class="mw-page-title-main">1-Butanol</span> Chemical compound

1-Butanol, also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and tert-butanol. The unmodified term butanol usually refers to the straight chain isomer.

<span class="mw-page-title-main">Propargyl alcohol</span> Chemical compound

Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula C3H4O. It is the simplest stable alcohol containing an alkyne functional group. Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents.

<span class="mw-page-title-main">1-Bromopropane</span> Chemical compound

1-Bromopropane (n-propylbromide or nPB) is an organobromine compound with the chemical formula CH3CH2CH2Br. It is a colorless liquid that is used as a solvent. It has a characteristic hydrocarbon odor. Its industrial applications increased dramatically in the 21st century due to the phasing out of chloro­fluoro­carbons and chloro­alkanes such as 1,1,1-Trichloro­ethane under the Montreal Protocol.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.

Propyl propanoate (also known as propyl propionate and n-propyl propionate) is the organic compound with the molecular formula C6H12O2. It is the ester of propanol and propionic acid. Like most esters, propyl propanoate is a colorless liquid with a fruity odor. The scent of propyl propionate is described as a chemically tinged pineapple or pear. It is used in perfumery and as a solvent. The refractive index at 20 °C is 1.393.

Isopropyl alcohol is a colorless, flammable organic compound with a pungent alcoholic odor.

<span class="mw-page-title-main">Hydrophile</span> Molecular entity that is attracted to water

A hydrophile is a molecule or other molecular entity that is attracted to water molecules and tends to be dissolved by water.

Propyl hexanoate (C9H18O2), also known as propyl caproate, is an ester formed by the reaction of propanol with hexanoic acid. Although it is a completely different ester, propyl hexanoate shares the same chemical formula with methyl octanoate, ethyl heptanoate, butyl pentanoate, etc. because they all have the same total carbon chain length. The scent of this ester can be described as that of blackberries, pineapple, cheese or wine.

Propionitrile, also known as ethyl cyanide and propanenitrile, is an organic compound with the formula CH3CH2CN. It is a simple aliphatic nitrile. The compound is a colourless, water-soluble liquid. It is used as a solvent and a precursor to other organic compounds.

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. 1 2 3 4 5 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. ↑ Pourkarim, Fariba; Mirheydari, Seyyedeh Narjes; Martinez, Fleming; Jouyban, Abolghasem (2019-05-05). "Solubility of acetaminophen in 1-propanol + water mixtures at T = 293.2–313.2 K". Physics and Chemistry of Liquids. 58 (4): 456–472. doi:10.1080/00319104.2019.1611827. ISSN   0031-9104.
  6. ↑ Ohtake, Toshiyuki; Kawase, Naoki; Pontrelli, Sammy; Nitta, Katsuaki; Laviña, Walter A.; Shen, Claire R.; Putri, Sastia P.; Liao, James C.; Fukusaki, Eiichiro (2022-04-14). "Metabolomics-Driven Identification of the Rate-Limiting Steps in 1-Propanol Production". Frontiers in Microbiology. 13. doi: 10.3389/fmicb.2022.871624 . ISSN   1664-302X. PMC   9048197 . PMID   35495658.
  7. 1 2 Jiménez-Serra, Izaskun; Rodríguez-Almeida, Lucas F.; Martín-Pintado, Jesús; Rivilla, Víctor M.; Melosso, Mattia; Zeng, Shaoshan; Colzi, Laura; Kawashima, Yoshiyuki; Hirota, Eizi; Puzzarini, Cristina; Tercero, Belén; de Vicente, Pablo; Rico-Villas, Fernando; Requena-Torres, Miguel A.; Martín, Sergio (July 2022). "Precursors of fatty alcohols in the ISM: Discovery of n-propanol". Astronomy & Astrophysics. 663: A181. arXiv: 2204.08267 . Bibcode:2022A&A...663A.181J. doi:10.1051/0004-6361/202142699. ISSN   0004-6361.
  8. ↑ Jiménez-Serra, Izaskun; Rodríguez-Almeida, Lucas F.; Martín-Pintado, Jesús; Rivilla, Víctor M.; Melosso, Mattia; Zeng, Shaoshan; Colzi, Laura; Kawashima, Yoshiyuki; Hirota, Eizi; Puzzarini, Cristina; Tercero, Belén; de Vicente, Pablo; Rico-Villas, Fernando; Requena-Torres, Miguel A.; Martín, Sergio (July 2022). "Precursors of fatty alcohols in the ISM: Discovery of n-propanol". Astronomy & Astrophysics. 663: A181. arXiv: 2204.08267 . Bibcode:2022A&A...663A.181J. doi:10.1051/0004-6361/202142699. ISSN   0004-6361.
  9. 1 2 Papa AJ (2011). "Propanols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_173.pub2. ISBN   9783527303854.
  10. 1 2 3 4 5 6 Zhang, Lin-Shang; Xu, Pei; Chu, Mei-Yun; Zong, Min-Hua; Yang, Ji-Guo; Lou, Wen-Yong (2019-10-21). "Using 1-propanol to significantly enhance the production of valuable odd-chain fatty acids by Rhodococcus opacus PD630". World Journal of Microbiology and Biotechnology. 35 (11). doi:10.1007/s11274-019-2748-0. ISSN   0959-3993.
  11. ↑ Lang, Reinhold Andreas; Egli-Gany, Dianne; Brill, Florian Holger Hubert; Böttrich, Johannes Georg; Breuer, Marion; Breuer, Burkhard; Kirschner, Martin Hartwig (2010-12-01). "Transdermal absorption of ethanol- and 1-propanol-containing hand disinfectants". Langenbeck's Archives of Surgery. 396 (7): 1055–1060. doi:10.1007/s00423-010-0720-4. ISSN   1435-2443. 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.
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