3-amino-1-propanol

Structural formula
General
Surname	3-amino-1-propanol
other names	3-aminopropan-1-ol ( IUPAC ); 1,3-propanolamine; n -propanolamine; 3-aminopropanol;
Molecular formula	C 3 H 9 NO
Brief description	colorless liquid with an amine-like odor
External identifiers / databases
EC number	205-864-4
ECHA InfoCard	100.005.333
PubChem	9086
ChemSpider	8733
Wikidata	Q223042
properties
Molar mass	75.11 g mol −1
Physical state	liquid
density	0.99 g cm −3 (20 ° C)
Melting point	11 ° C
boiling point	187-190 ° C
Vapor pressure	0.149 hPa (25 ° C); 1.6 hPa (40 ° C); 16.0 hPa (80 ° C);
solubility	soluble in water , ethanol and diethyl ether
Refractive index	1.4617 (20 ° C)
safety instructions
H and P phrases	H: 302-314-290
	P: 280-305 + 351 + 338-310
Toxicological data	2790 mg kg −1 ( LD 50 , rat , oral ) ; 1230 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	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

3-Amino-1-propanol (according to IUPAC nomenclature: 3-aminopropan-1-ol , often also referred to as n-propanolamine ) is an organochemical compound from the group of amino alcohols .

Extraction and presentation

3-Amino-1-propanol is produced on an industrial scale by the catalytic hydrogenation of ethylene cyanohydrin with hydrogen at temperatures of 50–150 ° C. and pressures of 120–250 bar in the presence of ammonia . The catalysts used are, for example, Raney nickel or Raney cobalt, as well as metal oxide and metal hydroxide catalysts.

The complete reaction is preferably carried out in fixed bed reactors operated in the trickle mode. The product is purified and worked up by multi-stage distillation in rectification columns .

3-Amino-1-propanol can also be produced by reducing β-alanine esters or 3-nitropropanol.

properties

Physical Properties

3-Amino-1-propanol has a relative gas density of 2.59 (density ratio to dry air at the same temperature and pressure ) and a relative density of the steam-air mixture of 1.00 (density ratio to dry air at 20 ° C and normal pressure ). The density is 0.99 g / cm ³ at 20 ° C. In addition, propanolamine has a vapor pressure of 0.149 hPa at 25 ° C, 1.6 hPa at 40 ° C and 16 hPa at 80 ° C. The kinematic viscosity is 29.9 mm ² s at 23 ° C.

Chemical properties

3-aminopropan-1-ol is a hardly flammable, flammable liquid from the group of amino alcohols . It is soluble in water, ethanol and diethyl ether and is difficult or very difficult to volatilize . The aqueous solutions of 3-aminopropan-1-ol have a strongly basic reaction . In addition, violent reactions occur with strong oxidizing agents and acids ; the substance decomposes when exposed to heat. An aqueous solution of concentration 10 g / l at 20 ° C has a pH of 11.6.

use

3-aminopropan-1-ol is used in the production of surfactants, dyes , synthetic resins , corrosion inhibitors and pharmaceuticals .

safety instructions

The vapors of 3-aminopropan-1-ol can form explosive mixtures with air when heated above the flash point. 3-aminopropan-1-ol is mainly absorbed through the respiratory tract . This leads to acute burns of the eyes by direct contact with the substance or their solutions. A skin-irritating effect was also found. A reproductive toxicity , mutagenicity or carcinogenicity has not yet been proven. Propanolamine has a lower explosion limit of approx. 2.50% by volume and an upper explosion limit of approx. 10.6% by volume. The ignition temperature is approx. 385 ° C. The substance therefore falls into temperature class T2. With a flash point of 101 ° C, 3-amino-1-propanol is considered very flame-retardant.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o Entry on 3-aminopropan-1-ol in the GESTIS substance database of the IFA , accessed on April 7, 2019(JavaScript required) .
↑ ^a ^b ^c Entry on aminopropanols. In: Römpp Online . Georg Thieme Verlag, accessed on April 7, 2019.
^ Entry on propanolamine in the Hazardous Substances Data Bank , accessed April 7, 2019.
^ ^A ^b Manfred Kroll, Andreas Edgar Herrmann, Dominik Herbrecht: Process for the production and purification of 3-aminopropanol. In: Google Patents. BASF SE, July 9, 2014, accessed April 7, 2019 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o Entry on 3-aminopropan-1-ol in the GESTIS substance database of the IFA , accessed on April 7, 2019(JavaScript required) .

[RÖMPP-2] Entry on aminopropanols. In: Römpp Online . Georg Thieme Verlag, accessed on April 7, 2019.

[HSDB-3] Entry on propanolamine in the Hazardous Substances Data Bank , accessed April 7, 2019.

[:0-4] A ^b Manfred Kroll, Andreas Edgar Herrmann, Dominik Herbrecht: Process for the production and purification of 3-aminopropanol. In: Google Patents. BASF SE, July 9, 2014, accessed April 7, 2019 .