Propylamine

Structural formula
General
Surname	Propylamine
other names	Propan-1-amine ( IUPAC ); 1-aminopropane; 1-propylamine; n -propylamine; Monopropylamine (MPA);
Molecular formula	C 3 H 9 N
Brief description	colorless liquid with an amine-like odor
External identifiers / databases
EC number	203-462-3
ECHA InfoCard	100.003.149
PubChem	7852
ChemSpider	7564
Wikidata	Q417852
properties
Molar mass	59.11 g mol −1
Physical state	liquid
density	0.72 g cm −3 (20 ° C)
Melting point	−83 ° C
boiling point	49 ° C
Vapor pressure	339 h Pa (20 ° C); 511 hPa (30 ° C); 748 hPa (40 ° C); 1060 hPa (50 ° C);
solubility	completely miscible with water; easily soluble in ethanol and diethyl ether ;
Refractive index	1.389 (20 ° C)
safety instructions
H and P phrases	H: 225-290-302-311-331-314-335
	P: 210-280-305 + 351 + 338-310-301 + 330 + 331-303 + 361 + 353
Toxicological data	370 mg kg −1 ( LD 50 , rat , oral ) ; 400 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
Thermodynamic properties
ΔH f 0	−101.5 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

Propylamine (according to IUPAC nomenclature: propan-1-amine , often also referred to as n- propylamine ) is an organic-chemical compound from the group of aliphatic primary amines .

Extraction and presentation

N- Propylamine is produced on an industrial scale by amination of 1-propanol with ammonia at temperatures of 170-230 ° C. and pressures of 1-30 bar in the presence of catalysts containing copper and aluminum oxide . Arise in addition to n-propylamine as by-products, even di- n -propylamine and tri- n -propylamine .

The entire reaction takes place in tube bundle reactors , in which molten salts keep the reaction at an almost constant temperature. The reactors are preferably operated in the gas cycle mode. An excess of ammonia can greatly increase the proportion of n-propylamine formed.

Another possibility for the preparation of propylamine consists of the complete catalytic hydrogenation of acrylonitrile .

properties

Physical Properties

Propylamine has a relative gas density of 2.04 (density ratio to dry air at the same temperature and pressure ) and a relative density of the vapor-air mixture of 1.35 (density ratio to dry air at 20 ° C and normal pressure ). The density is 0.72 g / cm ³ at 20 ° C. In addition, n-propylamine has a vapor pressure of 339 hPa at 20 ° C, 511 hPa at 30 ° C, 748 hPa at 40 ° C and 1060 hPa at 50 ° C. Propanamine has a dynamic viscosity of 0.39 mPa · s at 20 ° C.

Chemical properties

n- Propylamine is a highly flammable liquid from the group of aliphatic primary amines . It is completely miscible with water and easily miscible with ethanol and ether. The liquid is highly volatile. In addition, 1-propylamine reacts violently with strong oxidizing agents and mercury and air (explosive propylamine vapors). An aqueous solution of concentration 100 g / l at 20 ° C has a pH of 12.6. As a result, solutions of propylamine have a strongly alkaline reaction .

use

Monopropylamine is used as a solvent in numerous applications and is a precursor to the production of local anesthetics , herbicides , fungicides (e.g. prochloraz ) and insecticides . It is also used as a reagent for polymer modification. In complex chemistry , it is used as a ligand in metal complexes and for the production of intercalation compounds . In organic chemistry , n- propylamine is used for imine formation , N -alkylation , N -acylation , in reductive aminations and in heterocycle chemistry.

safety instructions

Propylamine is a highly flammable liquid . The vapors can form explosive mixtures with air when the substance is heated above its flash point. The substance is mainly absorbed through the respiratory tract and skin . This can range from slight irritation to severe burns of the mucous membranes and skin. Propylamine has a lower explosion limit (LEL) of 2.0% by volume (49 g / cm ³ ) and an upper explosion limit (UEL) of 10.4% by volume (256 g / cm ³ ). The ignition temperature is 320 ° C. The substance therefore falls into temperature class T2 and explosion group IIA. The limit gap width was determined to be 1.13 mm. With a flash point of −30 ° C, n- propylamine is considered highly flammable.

Web links

National Institute of Standards and Technology : physical data (English)

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p Entry on propylamine in the GESTIS substance database of the IFA , accessed on March 29, 2019(JavaScript required) .
↑ ^a ^b ^c Entry on Propylamine. In: Römpp Online . Georg Thieme Verlag, accessed on March 29, 2019.
^ Entry on Propylamine in the Hazardous Substances Data Bank , accessed March 29, 2019.
↑ 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.
↑ ^a ^b Martin Ernst, Bernd Stein, Steffen Maas, Jörg Pastre, Thorsten Johann, Johann-Peter Melder: Process for the continuous production of an amine using an aluminum-copper catalyst. In: Google Patents. BASF SE, March 19, 2014, accessed on March 29, 2019 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p Entry on propylamine in the GESTIS substance database of the IFA , accessed on March 29, 2019(JavaScript required) .

[RÖMPP-2] Entry on Propylamine. In: Römpp Online . Georg Thieme Verlag, accessed on March 29, 2019.

[HSDB-3] Entry on Propylamine in the Hazardous Substances Data Bank , accessed March 29, 2019.

[CRC90_5_25-4] 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.

[:0-5] Martin Ernst, Bernd Stein, Steffen Maas, Jörg Pastre, Thorsten Johann, Johann-Peter Melder: Process for the continuous production of an amine using an aluminum-copper catalyst. In: Google Patents. BASF SE, March 19, 2014, accessed on March 29, 2019 .