Isophorone diisocyanate

Isophorone diisocyanate (IPDI) is an organic compound in the class known as isocyanates. More specifically, it is an aliphatic diisocyanate. It is produced in relatively small quantities, accounting for (with hexamethylene diisocyanate) only 3.4% of the global diisocyanate market in the year 2000.[2] Aliphatic diisocyanates are used, not in the production of polyurethane foam, but in special applications, such as enamel coatings which are resistant to abrasion and degradation from ultraviolet light. These properties are particularly desirable in, for instance, the exterior paint applied to aircraft.

Isophorone diisocyanate

Names
IUPAC name 5-isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane
Other names IPDI
Identifiers
CAS Number	4098-71-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:53214
ChemSpider	147926
ECHA InfoCard	100.021.692
PubChem CID	169132
UNII	43B0856528
CompTox Dashboard (EPA)	DTXSID0023826
InChI InChI=1S/C12H18N2O2/c1-11(2)4-10(14-9-16)5-12(3,6-11)7-13-8-15/h10H,4-7H2,1-3H3 Key: NIMLQBUJDJZYEJ-UHFFFAOYSA-N InChI=1/C12H18N2O2/c1-11(2)4-10(14-9-16)5-12(3,6-11)7-13-8-15/h10H,4-7H2,1-3H3 Key: NIMLQBUJDJZYEJ-UHFFFAOYAN
SMILES O=C=N\C1CC(C\N=C=O)(CC(C1)(C)C)C
Properties
Chemical formula	C12H18N2O2
Molar mass	222.3 g/mol
Appearance	Colourless to slightly yellow liquid[1]
Odor	pungent[1]
Density	1.062 g/cm^3 @ 20 °C, liquid
Melting point	−60 °C (−76 °F; 213 K)
Boiling point	158 °C (316 °F; 431 K) at 1.33 kPa
Vapor pressure	0.0003 mmHg (20°C)[1]
Hazards
Flash point	155 °C (311 °F; 428 K) (PMCC)
NIOSH (US health exposure limits):
PEL (Permissible)	none[1]
REL (Recommended)	TWA 0.005 ppm (0.045 mg/m^3) ST 0.02 ppm (0.180 mg/m^3) [skin][1]
IDLH (Immediate danger)	N.D.[1]
Related compounds
Related isocyanates	Hexamethylene diisocyanate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Synthesis

IPDI is obtained by phosgenation of isophorone diamine:[2]

Chemistry

IPDI exists in two stereoisomers, cis and trans. Their reactivities are similar. Each stereoisomer is an unsymmetrical molecule, and thus has isocyanate groups with different reactivities. The primary isocyanate group is more reactive than the secondary isocyanate group.[2]

See also

• Methylene diphenyl diisocyanate
• Toluene diisocyanate
• Hexamethylene diisocyanate
• Isophorone

References

1. NIOSH Pocket Guide to Chemical Hazards. "#0356". National Institute for Occupational Safety and Health (NIOSH).
2. Randall, David; Lee, Steve (2002). The Polyurethanes Book. New York: Wiley. ISBN 0-470-85041-8.

External links

• NIOSH Safety and Health Topic: Isocyanates, from the website of the National Institute for Occupational Safety and Health (NIOSH)
• Isophorone diisocyanate - NIOSH Pocket Guide to Chemical Hazards