Isopropylamine

Structural formula
General
Surname	Isopropylamine
other names	Propan-2-amine ( IUPAC ) 2-propanamine 2-aminopropane 1-methylethylamine 2-propylamine Monoisopropylamine MIPA
Molecular formula	C 3 H 9 N
Brief description	colorless liquid with an amine-like odor
External identifiers / databases
CAS number 75-31-0 EC number 200-860-9 ECHA InfoCard 100,000,783 PubChem 6363 ChemSpider 6123 Wikidata Q420554
properties
Molar mass	59.11 g mol −1
Physical state	liquid
density	0.69 g cm −3 (20 ° C)
Melting point	−101 ° C
boiling point	32 ° C
Vapor pressure	633 h Pa (20 ° C)
solubility	miscible with water good in ethanol and diethyl ether
Refractive index	1.3746
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 224-301 + 311 + 331-314-335 P: 210-280-301 + 330 + 331-303 + 361 + 353-305 + 351 + 338-310
MAK	DFG : 5 ml m −3 or 12 mg m −3 Switzerland: 5 ml m −3 or 12 mg m −3
Toxicological data	111 mg kg −1 ( LD 50 ,  rat ,  oral ) 380 mg kg −1 ( LD 50 ,  rabbit ,  transdermal ) 9.67 mg l −1 / 4h ( LC 50 ,  rat ,  inh. )
Thermodynamic properties
ΔH f 0	−112.3 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

Isopropylamine (according to IUPAC nomenclature : propan-2-amine , often also referred to as 2-aminopropane ) is an organic-chemical compound from the group of primary amines . It is a versatile intermediate product for numerous applications in both agrochemical and pharmaceutical chemistry .

Extraction and presentation

The technical production of isopropylamine takes place through the reaction of isopropanol with ammonia at temperatures of 180-220 ° C and pressures of 30-60 bar in the presence of hydrogen over copper , nickel and cobalt oxide catalysts , which are based on aluminum oxide (Al ₂ O ₃ ) are supported.

The reaction is preferably carried out in the gas phase and takes place continuously . The heterogeneous catalyst is arranged as a fixed bed in a tube or tube bundle reactor . As by-products fall in addition to water, small amounts of diisopropylamine (DIPA) to. The product mixture is worked up and purified by distillation or rectification . Both the conversion and the selectivity are over 90% based on isopropanol.

The reductive amination of acetone with ammonia also leads to isopropylamine.

properties

Physical Properties

Isopropylamine 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 1.65 (density ratio to dry air at 20 ° C and normal pressure ). The density is 0.69 g / cm ³ at 20 ° C. In addition, isopropylamine has a vapor pressure of 633 hPa at 20 ° C, 943 hPa at 30 ° C, 1.360 bar at 40 ° C and 3.580 bar at 65 ° C. The dynamic viscosity is 0.36 mPa · s at 20 ° C.

Chemical properties

Monoisopropylamine is an organic chemical compound from the group of aliphatic primary amines . Aqueous solutions have a strong alkaline reaction . Isopropylamine attracts water and carbon dioxide from the air . At 20 ° C an aqueous solution with a concentration of 700 g / l has a pH value of 13. Isopropylamine reacts strongly exothermically with strong acids . Carcinogenic N-nitrosamines can be formed with nitrosating compounds .

use

Isopropylamine is a versatile intermediate in the manufacture of dyes , rubber chemicals , pharmaceuticals such as beta blockers , antihypertensive drugs , antiasthmatics, anti-glaucoma drugs , insecticides , emulsifiers and detergents . It is also used in the manufacture of glyphosate , atrazine and other triazine herbicides . Isopropylamine is also used in the synthesis of surfactants , solvents and active pharmaceutical ingredients. The salts of isopropylamine are used as buffer substances , corrosion inhibitors as well as fuel and lubricant additives .

safety instructions

Isopropylamine is an extremely flammable and highly volatile liquid from the group of aliphatic amines . The vapors form explosive mixtures with air . Aqueous solutions have a strong alkaline reaction . Acute and chronic health risks arise from this substance. The vapors and the liquid are extremely irritating to the respiratory tract , mucous membranes and skin . Long-term exposure can cause severe burns and a deteriorated general condition, respiratory disorders , apathy and balance disorders . When inhaled , breathing disorders, tearing, nasal discharge, salivation, hyperactivity , slowing of breathing ( bradypnea ) and, after exposure , crusts around the nose and eyes are probable. There are narcotic effects and the risk of pulmonary edema . Also kidney damage are possible.

Individual evidence

1. ↑ ^{a b c d e f g h i j k l m n o} Entry on isopropylamine in the GESTIS substance database of the IFA , accessed on January 14, 2019(JavaScript required) .
2. ↑ ^{a b c d e} entry on Propylamine. In: Römpp Online . Georg Thieme Verlag, accessed on January 14, 2019.
3. ↑ Entry on Isopropylamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 14, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
4. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 75-31-0 or 2-aminopropane ), accessed on September 29, 2019.
5. ↑ 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.
6. ↑ ^{a b} Patent EP2782898B1 : Process for the production of ethylamines and mono-iso-propylamine (MIPA). Published on October 21, 2015 , applicant: BASF SE, inventors: Norbert Asprion, Manfred Julius, Oliver Bey, Stefanie Werland, Frank Stein, Matthias Kummer, Wolfgang Mägerlein, Johann-Peter Melder, Kevin Huyghe, Maarten Moors. ‌