1-Propanol

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1-Propanol
Skeletal formula of 1-propanol
Skeletal formula of 1-propanol with all explicit hydrogens added Ball and stick model of 1-propanol
Identifiers
CAS number 71-23-8 YesY
PubChem 1031
ChemSpider 1004 YesY
UNII 96F264O9SV YesY
EC number 200-746-9
UN number 1274
DrugBank DB03175
KEGG C05979 N
MeSH 1-Propanol
ChEBI CHEBI:28831 YesY
ChEMBL CHEMBL14687 YesY
RTECS number UH8225000
ATC code D08AX03
Beilstein Reference 1098242
Gmelin Reference 25616
3DMet B00883
Jmol-3D images Image 1
Properties
Molecular formula C3H8O
Molar mass 60.10 g mol−1
Appearance Colorless liquid
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
Solubility in water miscible
log P 0.329
Vapor pressure 1.99 kPa (at 20 °C)
Acidity (pKa) 16
Basicity (pKb) −2
Refractive index (nD) 1.387
Viscosity 1.938 mPa s
Dipole moment 1.68 D
Thermochemistry
Specific
heat capacity
C
143.96 J K−1 mol−1
Std molar
entropy
So298
192.8 J K−1 mol−1
Std enthalpy of
formation
ΔfHo298
−302.79–−302.29 kJ mol-1
Std enthalpy of
combustion
ΔcHo298
−2.02156–−2.02106 MJ mol-1
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H225, H318, H336
GHS precautionary statements P210, P261, P280, P305+351+338
EU Index 603-003-00-0
EU classification Highly Flammable F Irritant Xi
R-phrases R11, R41, R67
S-phrases (S2), S7, S16, S24, S26, S39
NFPA 704
Flammability code 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., gasoline) Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 22 °C (72 °F; 295 K)
Explosive limits 13.7%
Related compounds
Related compounds Butane

Propanamine

Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Propanol, technically known as 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[edit]

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[edit]

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.[2]

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[edit]

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.[3]

Inhalation[edit]

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[edit]

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.[4]

References[edit]

  1. ^ "1-Propanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 10 October 2011. 
  2. ^ Anthony J. Papa "Propanols" in Ullmann’s Encyclopedia of Industrial Chemistry 2011, Wiley-VCH, Weinheim. doi:10.1002/14356007.a22_173.pub2
  3. ^ "N-PROPANOL Health-Base Assessment and Recommendation for HEAC". 
  4. ^ "Bioalcohols". Biofuel.org.uk. Retrieved 2014-04-16. 

Further reading[edit]

  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, David R., ed. (2006-06-26). CRC Handbook of Chemistry and Physics, 87th Edition (87 ed.). TF-CRC. ISBN 0-8493-0487-3. 
  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. 
  4. Perkin, W. H.; Kipping, F. S (1922). Organic Chemistry. London: W. & R. Chambers. ISBN 0-08-022354-0. 

External links[edit]