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Propan-1-ol

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Propan-1-ol
Skeletal formula of 1-propanol
Ball and stick model of 1-propanol
Names
Pronunciation ˈprəʊpən.wən.ɒl
Preferred IUPAC name
Propan-1-ol
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
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 checkY
    Key: BDERNNFJNOPAEC-UHFFFAOYSA-N checkY
  • CCCO
Properties
C3H8O
Molar mass 60.096 g·mol−1
Appearance Colorless liquid
Odor mild, alcohol-like
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)
1.68 D
Thermochemistry
143.96 J/(K·mol)
Std molar
entropy
(S298)
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:
GHS02: Flammable GHS07: Exclamation mark
Danger
H225, H302, H318, H336
P210, P261, P280, P305+P351+P338
NFPA 704 (fire diamond)
1
3
0
Flash point 22 °C (72 °F; 295 K)
371 °C (700 °F; 644 K)
Explosive limits 2.2–13.7%
Lethal dose or concentration (LD, LC):
2800 mg/kg (rabbit, oral)
1699 mg/kg (mouse, oral)
1870 mg/kg (rat, oral)
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 200 ppm (500 mg/m3)
REL (Recommended)
TWA 200 ppm (500 mg/m3) ST 250 ppm (625 mg/m3) [skin]
IDLH (Immediate danger)
800 ppm
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).
☒N verify (what is checkY☒N ?)

Propan-1-ol (also propanol, n-propyl alcohol) is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colourless liquid and an isomer of 2-propanol. 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, and, sometimes, as a disinfecting agent.

Chemical properties

Some example reactions of propan-1-ol

Propan-1-ol 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 n-propyl chloride. 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 propan-1-ol with Na2Cr2O7 and H2SO4 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

Propan-1-ol 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.

H2C=CH2 + CO + H2 → CH3CH2CH=O
CH3CH2CH=O + H2 → CH3CH2CH2OH

A traditional laboratory preparation of propan-1-ol involves treating n-propyl iodide with moist Ag2O.

Safety

Propan-1-ol is thought to be similar to ethanol in its effects on the 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, one case of lethal propan-1-ol poisoning was reported.

Propan-1-ol as fuel

Propan-1-ol has high octane number and is suitable for engine fuel usage. However, propanol is too expensive to use as a motor fuel. The research octane number (RON) of propanol is 118, and anti-knock index (AKI) is 108.

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


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