1-propanol

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Structural formula
Structural formula of 1-propanol
General
Surname 1-propanol
other names
  • Propan-1-ol ( IUPAC )
  • n -propanol
  • Propyl alcohol
  • Propanol
  • Optal
  • Terosol
  • 1-hydroxypropane
  • PROPYL ALCOHOL ( INCI )
Molecular formula C 3 H 8 O
Brief description

colorless liquid smelling of alcohol

External identifiers / databases
CAS number 71-23-8
EC number 200-746-9
ECHA InfoCard 100,000,679
PubChem 1031
ChemSpider 1004
DrugBank DB03175
Wikidata Q14985
properties
Molar mass 60.10 g mol −1
Physical state

liquid

density

0.80 g cm −3 (20 ° C)

Melting point

−126 ° C

boiling point

97 ° C

Vapor pressure

20.3 h Pa (20 ° C)

solubility

miscible with water, ethanol and diethyl ether

Refractive index

1.385 (at 20 ° C)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
02 - Highly / extremely flammable 05 - Corrosive 07 - Warning

danger

H and P phrases H: 225-318-336
P: 210-240-280-305 + 351 + 338-313-403 + 233
MAK

Switzerland: 200 ml m −3 or 500 mg m −3

Toxicological data

1870 mg kg −1 ( LD 50ratoral )

Thermodynamic properties
ΔH f 0

−302.6 kJ / mol

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

1-Propanol (also: n -propanol , n -propyl alcohol , according to IUPAC propan-1-ol ), but mostly only referred to as propanol , is an organic compound from the alcohol class . It is a monohydric, primary alkanol. There is exactly one isomeric alcohol of 1-propanol, branched 2-propanol (or isopropyl alcohol or isopropanol).

Systematics

1-Propanol (C 3 H 7 OH) belongs to the linear n - alkanols . 1-Propanol is derived from the alkane ( saturated hydrocarbon ) propane (C 3 H 8 ) by formally replacing a hydrogen atom with the functional hydroxyl group  (-OH). To name the name is propane , the suffix ol appended. The empirical formula for 1-propanol according to the Hill system is C 3 H 8 O, the notation C 3 H 7 OH , which is also used, is not a sum formula but a semi-structural formula .

Occurrence

1-Propanol is a component of fusel oils , i.e. a natural breakdown product of the yeast metabolism.

Extraction and presentation

1-Propanol is produced on an industrial scale exclusively by the catalytic hydrogenation of propionaldehyde at temperatures of 110-150 ° C and pressures of 1.5-10 bar in the presence of copper- nickel- zinc- chromium catalysts based on aluminum oxide (Al 2 O 3 ) or diatomaceous are supported manufactured.

Catalytic hydrogenation of propionaldehyde to form n-propanol in the presence of a copper-nickel catalyst supported on aluminum oxide

The reaction is carried out in the gas phase . The hydrogen is used in up to a 20-fold molar excess. In this process, 1-propanol yields of more than 99% are achieved with a conversion (propionaldehyde) of 99.9%.

properties

Physical Properties

At room temperature, 1-propanol is a thin, clear liquid that smells like ethanol. The flash point is 22 ° C, the ignition temperature 385 ° C. The lower explosion limit is 2.1% by volume, the upper 19.2% by volume. The refractive index at 20 ° C is 1.385.

The compound forms azeotropically boiling mixtures with a number of solvents . The azeotropic compositions and boiling points can be found in the following table. No azeotropes are formed with methanol , ethanol , 2-propanol , n- butanol , iso- butanol , sec- butanol , ethanediol , n- pentane , chloroform , acetone , methyl ethyl ketone , diethyl ether , diisopropyl ether , tetrahydrofuran , methyl acetate , ethyl acetate and pyridine .

Azeotropes with various solvents
solvent water n-hexane n-heptane n-octane n-nonane Cyclohexane benzene toluene
Content of n-propanol in% 71 4th 36 70 98 20th 17th 49
boiling point in ° C 87 66 88 94 97 74 77 93
solvent MIBK 1,4-dioxane n-butyl acetate Carbon disulfide Acetonitrile Trichlorethylene Carbon tetrachloride Chlorobenzene
Content of n-propanol in% 34 55 40 5 28 17th 8th 80
boiling point in ° C 94 95 94 46 81 82 73 97

Chemical properties

Due to the longer hydrophobic residue, 1-propanol has a significantly less tendency to absorb water than the lower alcohols. Propanolates can be produced by reacting with alkali metals .

use

1-Propanol is often used as a solvent , for example in paint production. It can also be used in detergents and disinfectants (has a bactericidal , tuberculocidal , fungicidal and limited virucidal effect)be included. It is used as a raw material for the manufacture of insecticides , herbicides and medicines .

In some applications it replaces the toxic methanol .

toxicology

1-Propanol vapors irritate eyes, skin and mucous membranes . Direct contact of the liquid with the eyes can cause serious eye damage. When ingested, the liquid has a narcotic effect similar to that of ethanol and, in higher concentrations, leads to dizziness, drowsiness and, in high concentrations, to intoxication or even unconsciousness. Due to the possibility of serious eye damage, 1-propanol should not be used for manual use, for example when used as a cleaning agent , and the less dangerous 2-propanol (isopropanol) should be used. If this is not possible, protective goggles should be worn when working with 1-propanol.

Web links

Commons : Propan-1-ol  - Collection of pictures, videos, and audio files

Individual evidence

  1. Entry on PROPYL ALCOHOL in the CosIng database of the EU Commission, accessed on July 6, 2020.
  2. a b c d e f g h Entry for CAS no. 71-23-8 in the GESTIS substance database of the IFA , accessed on July 9, 2016(JavaScript required) .
  3. Data sheet 1-propanol (PDF) from Carl Roth , accessed on December 14, 2010.
  4. a b c Entry on propanols. In: Römpp Online . Georg Thieme Verlag, accessed on December 25, 2014.
  5. chemischemlexikon.de: Specification 1-Propanol - Art.-No .: 10-0486 ( Memento of October 9, 2009 in the Internet Archive )
  6. Entry on propan-1-ol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  7. Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 71-23-8 or n-propanol ), accessed on September 14, 2019.
  8. David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-25.
  9. a b Jens Klabunde, Chris Bischoff, Anthony J. Papa: Propanols. In: Ullmann's Encyclopedia of Industrial Chemistry . Wiley ‐ VCH Verlag GmbH & Co. KGaA., May 25, 2018, p. 5, doi : 10.1002 / 14356007.a22_173.pub3 .
  10. a b I.M. Smallwood: Handbook of organic solvent properties , Arnold London 1996, ISBN 0-340-64578-4 , pp. 70-72.