1,2-diaminopropane

Structural formula
Simplified structural formula without stereochemistry
General
Surname	1,2-diaminopropane
other names	Propane-1,2-diamine ( IUPAC ) 1,2-propylenediamine 1,2 PDA Propylenediamine (ambiguous)
Molecular formula	C 3 H 10 N 2
Brief description	colorless liquid with an ammonia-like odor
External identifiers / databases
CAS number 78-90-0 [racemate] 10424-38-1 [ (R) -enantiomer] 15967-72-3 [ (S) -enantiomer] EC number 201-155-9 ECHA InfoCard 100.001.051 PubChem 6567 ChemSpider 13849260 Wikidata Q161461
properties
Molar mass	74.13 g mol −1
Physical state	liquid
density	0.87 g cm −3 (20 ° C)
Melting point	−12 ° C (pure substance) −37 ° C (technical product)
boiling point	119 ° C
Vapor pressure	3.6 h Pa (20 ° C)
solubility	miscible with water miscible with most organic solvents
Refractive index	1.445-1.447
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 226-302-311-314-317-334 P: 261-280-305 + 351 + 338-310
Toxicological data	2230 mg kg −1 ( LD 50 ,  rat ,  oral ) 435 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

1,2-Diaminopropane (according to IUPAC nomenclature: propane-1,2-diamine , often also referred to as 1,2-propylenediamine ) is an organic-chemical compound from the group of aliphatic amines . It is used as an intermediate for pesticides and pharmaceuticals .

Extraction and presentation

For the industrial production of 1,2-diaminopropane, isopropanolamine is used with ammonia at temperatures of 120–240 ° C and pressures of 60–170 bar in the presence of copper , nickel and cobalt oxide catalysts , which are based on aluminum oxide (Al ₂ O ₃ ) are carried to.

The complete reaction takes place in the liquid phase in a continuous tube or tube bundle reactor . The catalyst is arranged as a fixed bed and the reaction is carried out in the upflow mode. The product is purified and worked up by multi-stage distillation in rectification columns .

1,2-Diaminopropane can also be produced by amination of 1,2-propanediol . The enantiomers are obtained by resolution .

properties

Physical Properties

Propane-1,2-diamine has a relative gas density of 2.56 (density ratio to dry air at the same temperature and pressure ) and a relative density of the steam-air mixture of 1.01 (density ratio to dry air at 20 ° C and normal pressure ). In addition, propane-1,2-diamine has a vapor pressure of 3.6 hPa at 20 ° C. Furthermore, the dynamic viscosity is 1.7 mPa · s at 20 ° C.

Chemical properties

Propane-1,2-diamine is a flammable liquid belonging to the group of aliphatic amines . It is miscible with water and most organic solvents . In addition, it is difficult or very difficult to volatilize. The fabric decomposes when exposed to heat. Contact with oxidizing agents and acids can lead to dangerous chemical reactions . Furthermore, 1,2-diaminopropane forms carcinogenic nitrosamines with nitrosating agents (e.g. nitrites , nitrous acid , nitrous gases ) . It reacts as a strong base . An aqueous solution with a concentration of 100 g / l has a pH value of 12 at a temperature of 20 ° C.

use

1,2-Diaminopropane is mainly used as an intermediate in the manufacture of pesticides and pharmaceuticals . In the United States of America it is also used in the form of derivatives for additives to fuels and lubricants . It is also used as an emulsifier and in polymer modification . It is also a component of coating materials, dyes , hair dyes and textile auxiliaries and is used in electrochemical processes for metal coatings. 1,2-Diaminopropane is also a chelate ligand for the production of ( chiral ) metal complexes and of polymerization catalysts. Finally, there will also be heterocyclic compounds - synthesis used.

safety instructions

The vapors of 1,2-propylenediamine can form explosive mixtures with air when the substance is heated above the flash point. This is possible even at higher ambient temperatures. The substance is mainly absorbed through the respiratory tract . Furthermore, a very effective absorption through the skin and the digestive tract is suspected. Ingestion or exposure leads to acute irritating to corrosive effects on mucous membranes and skin. Chronic information is not available for humans. Of particular concern is the rapid formation of highly toxic and carcinogenic nitrosamines , which are formed on contact with nitrosating agents. However, a direct mutagenic effect could be ruled out. Insufficient information is available on reproductive toxicity and carcinogenicity . 1,2-Diaminopropane has a lower explosion limit (LEL) of approx. 2.2% by volume and an upper explosion limit (UEL) of approx. 11.1% by volume. The ignition temperature is 360 ° C. The substance therefore falls into temperature class T2. With a flash point of 33 ° C, 1,2-diaminopropane is considered flammable.

See also

• 1,3-diaminopropane

Web links

Commons : 1,2 Propanediamine  - Collection of pictures, videos, and audio files

Individual evidence

1. ↑ ^{a b c d e f g h i j k l m n} Entry on propane-1,2-diamine in the GESTIS substance database of the IFA , accessed on July 26, 2019(JavaScript required) .
2. ↑ ^{a b c} Entry on Propandiamine. In: Römpp Online . Georg Thieme Verlag, accessed on July 26, 2019.
3. ↑ Entry on 1,2-diaminopropane at ChemBlink , accessed on July 26, 2019.
4. ↑ Entry on Propylenediamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on July 26, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
5. ↑ ^{a b} Patent WO2019105782 : Process for the continuous production of 1,2-propylenediamine (1,2-PDA) and dimethyldiethylenetriamine (DMDETA). Published on June 6, 2019 , applicant: BASF SE, inventor: Christian Eidamshaus, Johann-Peter Melder, Joerg Pastre, Hans-Juergen Pallasch. ‌
6. ↑ Data sheet 1,2-diaminopropane (PDF) from Merck , accessed on July 26, 2019.