1,3-diaminopropane

Structural formula
General
Surname	1,3-diaminopropane
other names	1,3-propylenediamine; Propane-1,3-diamine; Trimethylenediamine; Propane-1,3-diylenediamine;
Molecular formula	C 3 H 10 N 2
Brief description	colorless, flammable liquid with an amine-like odor
External identifiers / databases
EC number	203-702-7
ECHA InfoCard	100.003.367
PubChem	428
Wikidata	Q161498
properties
Molar mass	74.13 g mol −1
Physical state	liquid
density	0.89 g cm −3
Melting point	−12 ° C
boiling point	139.3 ° C
Vapor pressure	4.1 h Pa (20 ° C); 5.8 hPa (25 ° C);
solubility	completely miscible with water
Refractive index	1.4565-1.4585
safety instructions
H and P phrases	H: 226-290-302-310-314-317-334
	P: 210-280-280-301 + 330 + 331-302 + 352-304 + 340-305 + 351 + 338-308 + 310
Toxicological data	311 mg kg −1 ( LD 50 , rat , oral )
	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

1,3-Diaminopropane is an organic chemical compound from the group of aliphatic amines . Along with 1,2-diaminopropane, it is one of the two structural isomers of propanediamines.

Occurrence

The compound occurs in plants such as vines , tomatoes or aquatic plants as well as in microorganisms such as amoebas , where it acts as a growth regulator. Increased concentrations are formed in the event of an attack by parasites or other plant diseases .

Extraction and presentation

1,3-Diaminopropane is produced by reacting 1,3-propanediol with ammonia or by adding ammonia to acrylonitrile and then hydrogenating it.

properties

Physical Properties

1,3-Diaminopropane is a colorless to yellowish liquid with an amine- like odor. The boiling point under normal pressure is 139.7 ° C, the heat of vaporization at the boiling point is 50.18 kJ · mol ⁻¹ . A thermoanalytical measurement showed a melting point of −11 ° C and a heat of fusion of 12.19 kJ mol ⁻¹ .

Chemical properties

1,3-Diaminopropane form with metal ions z. B. Copper and nickel ions stable chelate complexes . A reductive amination with formaldehyde leads to N , N , N ', N ' -tetramethyl-1,3-propylenediamine .

Safety-related parameters

1,3-Diaminopropane forms flammable vapor-air mixtures at high temperatures. The compound has a flash point of 48 ° C. The explosion range is between 2.8 vol.% As the lower explosion limit (LEL) and 15.2 vol.% As the upper explosion limit (UEL). The ignition temperature is 350 ° C. The substance therefore falls into temperature class T2.

use

1,3-Diaminopropane is used to manufacture u. a. of textile finishing agents, photo chemicals, hardeners for epoxy resins , wood preservatives , pharmaceuticals and pesticides . The compound is a component of detergents , hair dyes and lubricants . It can be used as a building block for polymers and dendrimers , as well as a reagent for polymer modification

toxicology

Contact with the liquid or the vapors can cause irritation and even burns to the eyes, skin and mucous membranes. The inhalation of vapors may cause probably a burning sensation, coughing, wheezing, shortness of breath, headache, nausea and vomiting.

literature

Emil Fischer , H. Koch: About trimethylenediamine . In: Reports of the German Chemical Society , 1884, doi : 10.1002 / cber.18840170250
Alexandre O. Legendre, Fabiana C. Andrade et al. a .: 3D hydrogen-bonded network built from copper (II) complexes of 1,3-propanediamine. In: Journal of the Brazilian Chemical Society. 17, 2006, p. 1683, doi : 10.1590 / S0103-50532006000800029 .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m Entry on trimethylenediamine in the GESTIS substance database of the IFA , accessed on April 15, 2018(JavaScript required) .
↑ Entry on 1,3-diaminopropane at ChemBlink , accessed on February 25, 2011.
↑ Data sheet 1,3-diaminopropane (PDF) from Merck , accessed on April 21, 2016.
↑ ^a ^b ^c ^d ^e ^f Entry on Propandiamine. In: Römpp Online . Georg Thieme Verlag, accessed on April 15, 2018.
^ V. Majer, V. Svoboda: Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation. Blackwell Scientific Publications, Oxford 1985, p. 300.
↑ Dall'Acqua, L .; Della Gatta, G .; Nowicka, B .; Ferloni, P .: Enthalpies and entropies of fusion of ten alkane-α ω-diamines H ₂ N- (CH ₂ ) _n -NH ₂ where 3≤n≤12 in J. Chem. Thermodyn. 34 (2002) 1-12, doi : 10.1006 / jcht.2001.0950 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m Entry on trimethylenediamine in the GESTIS substance database of the IFA , accessed on April 15, 2018(JavaScript required) .

[2] Entry on 1,3-diaminopropane at ChemBlink , accessed on February 25, 2011.

[Merck-3] Data sheet 1,3-diaminopropane (PDF) from Merck , accessed on April 21, 2016.

[Römpp-4] ↑ ^a ^b ^c ^d ^e ^f Entry on Propandiamine. In: Römpp Online . Georg Thieme Verlag, accessed on April 15, 2018.

[Majer_Svoboda-5] V. Majer, V. Svoboda: Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation. Blackwell Scientific Publications, Oxford 1985, p. 300.

[Gatta-6] Dall'Acqua, L .; Della Gatta, G .; Nowicka, B .; Ferloni, P .: Enthalpies and entropies of fusion of ten alkane-α ω-diamines H ₂ N- (CH ₂ ) _n -NH ₂ where 3≤n≤12 in J. Chem. Thermodyn. 34 (2002) 1-12, doi : 10.1006 / jcht.2001.0950 .