1-Propanol

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1-Propanol
Ball and stick model of 1-propanol
Names
IUPAC name
Propan-1-ol[1]
Other names
  • n-Propyl alcohol
  • n-Propanol
  • n-PrOH
  • Ethylcarbinol
  • 1-Hydroxypropane
  • Propionic alcohol
  • Propionyl alcohol
  • Propionylol
  • Propyl alcohol
  • Propylic alcohol
  • Propylol
Identifiers
71-23-8 YesY
3DMet B00883
1098242
ChEBI CHEBI:28831 YesY
ChEMBL ChEMBL14687 YesY
ChemSpider 1004 YesY
DrugBank DB03175 YesY
EC Number 200-746-9
25616
Jmol 3D model Interactive image
KEGG C05979 N
MeSH 1-Propanol
PubChem 1031
RTECS number UH8225000
UNII 96F264O9SV YesY
UN number 1274
Properties
C3H8O
Molar mass 60.10 g·mol−1
Appearance Colorless liquid
Odor mild, alcohol-like[2]
Density .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
1.387
Viscosity 1.959 mPa×s (at 25 °C) [3]
1.68 D
Thermochemistry
143.96 J K−1 mol−1
192.8 J K−1 mol−1
−302.79–−302.29 kJ mol−1
−2.02156–−2.02106 MJ mol−1
Pharmacology
ATC code D08AX03
Vapor pressure {{{value}}}
Related compounds
Related compounds
Butane
Propanamine
Ethanol
Butanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

1-Propanol, is a primary alcohol with the formula CH3CH2CH2OH. This colorless liquid is also known as propan-1-ol, 1-propyl alcohol, n-propyl alcohol, and n-propanol. It is an isomer of isopropanol (2-propanol, isopropyl alcohol). It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry mainly for resins and cellulose esters.

Chemical properties

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 1-chloropropane. 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 only 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.

Some example reactions of 1-propanol

Preparation

1-Propanol is manufactured by catalytic hydrogenation of propionaldehyde. The propionaldehyde is itself 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.[4]

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.

1-Propanol was discovered in 1853 by Chancel, who obtained it by fractional distillation of fusel oil. Indeed, 1-propanol is a major constituent of fusel oil, a by-product formed from certain amino acids when potatoes or grains are fermented to produce ethanol. This process is no longer a significant source of 1-propanol.

Safety

1-Propanol is thought to be similar to ethanol in its effects on human body, but 2-4 times more potent. Oral LD50 in rats is 1870 mg/kg (compared to 7060 mg/kg for ethanol). It is metabolized into propionic acid. Effects include alcoholic intoxication and high anion gap metabolic acidosis. As of 2011, only one case of lethal 1-propanol poisoning was reported.[5]

Inhalation

Although this method is rare, it does indeed exist. Propanol might be much more convenient than ethanol for inhalation because of its potency with nebulizers.

Propanol as fuel

1-propanol has high octane numbers and it is suitable to engine fuel usage. However, production of propanol has been too expensive to be a common fuel. The Research octane number (RON) of propanol is 118 and Anti-Knock Index (AKI) is 108.[6]

References

  1. "1-Propanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 10 October 2011.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  2. Cite error: Invalid <ref> tag; no text was provided for refs named PGCH
  3. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  4. Anthony J. Papa "Propanols" in Ullmann’s Encyclopedia of Industrial Chemistry 2011, Wiley-VCH, Weinheim. doi:10.1002/14356007.a22_173.pub2
  5. "N-PROPANOL Health-Base Assessment and Recommendation for HEAC".<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  6. "Bioalcohols". Biofuel.org.uk. Retrieved 2014-04-16.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>

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 <templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  2. Lide, David R., ed. (2006-06-26). CRC Handbook of Chemistry and Physics, 87th Edition (87 ed.). TF-CRC. ISBN 0-8493-0487-3.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  3. Maryadele J. O'Neil, ed. (2006-11-03). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (14 ed.). Merck. ISBN 0-911910-00-X.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  4. Perkin, W. H.; Kipping, F. S (1922). Organic Chemistry. London: W. & R. Chambers. ISBN 0-08-022354-0.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>

External links