1-Propanol

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.

After several unsuccessful attempts, it was synthesized independently and by two different routes by Eduard Linnemann and Carl Schorlemmer in 1868.

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

Oxidation of 1-propanol with and 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.

Other proposed industrial processes include the two-step isomerization and hydrogenation of propylene oxide.

A traditional laboratory preparation of 1-propanol involves treating n-propyl iodide with moist .

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. 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.

References

References

1. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
2. (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.
3. {{PGCH. 0533
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8. Linnemann, Eduard. (1868). "Ueber die Darstellung der Fettalkohole aus ihren Anfangsgliedern. Reduction des Essigsäure-Anhydrids zu Aethylalkohol". Justus Liebigs Annalen der Chemie.
9. (1868). "Zeitschrift für Chemie". Quandt & Händel.
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11. Papa, Anthony J.. (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Wiley.
12. Unmack JL. (2011). "N-PROPANOL Health-Base Assessment and Recommendation for HEAC".
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