Isophoronediamine

Structural formula
Structural formula without stereochemistry
General
Surname	Isophoronediamine
other names	3-aminomethyl-3,5,5-trimethylcyclohexylamine IPDA 3-aminomethyl-3,5,5-trimethylcyclohexaline
Molecular formula	C 10 H 22 N 2
Brief description	colorless liquid with a faint amine odor
External identifiers / databases
CAS number 2855-13-2 (mixture of isomers) EC number 220-666-8 ECHA InfoCard 100,018,788 PubChem 17857 Wikidata Q1674522
properties
Molar mass	170.30 g mol −1
Physical state	liquid
density	0.92 g cm −3
Melting point	10 ° C
boiling point	247 ° C
Vapor pressure	0.02 hPa (20 ° C) 1 hPa (70 ° C)
solubility	miscible with water miscible with many organic solvents
Refractive index	1.488 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 314-302 + 312-317-412 P: 273-280-305 + 351 + 338-310
Toxicological data	1030 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

Isophoronediamine is a mixture of four stereoisomeric chemical compounds from the group of aliphatic amines .

Extraction and presentation

Isophoronediamine can be produced in a two-step process. For this purpose, isophorone and hydrogen cyanide are converted into isophoronenitrile , which then reacts further with ammonia and hydrogen to form isophoronediamine.

Around 35,000 tons were produced worldwide in 2002 (mainly in Germany at Degussa (now: Evonik Industries ), BASF and in the USA). This makes it one of the chemical substances that are produced in large quantities (" High Production Volume Chemical ", HPVC) and for which the Organization for Economic Cooperation and Development (OECD) collects data on possible dangers (" Screening Information Dataset ", SIDS).

properties

Isophoronediamine is a colorless, hygroscopic liquid with a faint amine odor. It is chiral and contains two stereocenters , hence there are four stereoisomers. A mixture of the respective racemic cis - and trans - diastereomers is sold commercially, the predominantly cis isomer present being more reactive. It is miscible with water and its aqueous solution has a strong alkaline reaction. The racemic cis form has a viscosity of 18 mPas at 20 ° C and decomposes at temperatures above 260 ° C.

Isophoronediamine forms flammable vapor-air mixtures at higher temperatures. The compound has a flash point of 112 ° C. The lower explosion limit is 1.2% by volume. The ignition temperature is 380 ° C. The substance therefore falls into temperature class T2.

use

Isophoronediamine serves as an intermediate product in the production of isophorone diisocyanate , which is used for the production of polyurethanes and here especially for polyurethane-based paints and adhesives . It is also used directly as a hardener for epoxy resins . Further applications are coatings with excellent corrosion protection properties for metals and adhesive bonds. It is also used in the manufacture of non-crystalline specialty polyamides , as a chain extender in polyurethanes and as an intermediate in the manufacture of dyes .

Web links

• Patent US7060857 : Method for the production of isophorondiamine (ipda, 3-aminomethyl-3,5,5-trimethyl-cyclohexylamine) having a high cis / tran-isomer ratio. Filed on Aug. 28, 2002 , published on June 13, 2006 , Applicant: BASF, inventor Frank Funke et al ..

Individual evidence

1. ↑ ^{a b} entry on isophoronediamine. In: Römpp Online . Georg Thieme Verlag, accessed on May 25, 2014.
2. ↑ ^{a b c d e f g h i j k l} Entry on isophoronediamine in the GESTIS substance database of the IFA , accessed on March 19, 2019(JavaScript required) .
3. ↑ Data sheet isophoronediamine (PDF; 191 kB) from Gischem, accessed on May 29, 2016.
4. ↑ Data sheet 5-Amino-1,3,3-trimethylcyclohexanemethylamine, mixture of cis and trans from Sigma-Aldrich , accessed on April 6, 2011 ( PDF ).
5. ↑ Entry on 3-aminomethyl-3,5,5-trimethylcyclohexylamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
6. ↑ ^{a b c d e} OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for Cyclohexylamine, 3-aminomethyl-3,5,5-trimethyl- , accessed on October 3, 2014.
7. ↑ Isophoronediamine data sheet (PDF) from Merck , accessed on February 23, 2010.
8. ↑ Horst Stepanski: Polyurethane adhesives. Springer-Verlag, 2016, ISBN 978-3-658-12270-6 , p. 18 ( limited preview in Google book search).
9. ↑ Entry on polyurethane adhesives. In: Römpp Online . Georg Thieme Verlag, accessed on February 26, 2016.