4,4-Diaminodicyclohexylmethane

4,4-Diaminodicyclohexylmethane
Names
	Other names 4,4'-methylenebiscyclohexanamine, methylene bis(4,4'-cyclohexylamine), bis(4-aminocyclohexyl)methane
Identifiers
CAS Number	1761-71-3 mixture of isomers; 6693-29-4 trans-trans isomer; 6693-30-7 trans-cis isomer; 1896-62-4 cis-cis isomer;
3D model (JSmol)	Interactive image;
EC Number	217-168-8 (mixture), 229-737-8 (trans-trans), 229-738-3 (trans-cis), 229-739-9 (cis-cis)
PubChem CID	15660;
UNII	AR21XLU05L; B16001JGEW; H8V09V2RM3;
	InChI InChI=1S/C13H26N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h10-13H,1-9,14-15H2 Key: DZIHTWJGPDVSGE-UHFFFAOYSA-N;
	SMILES C1CC(CCC1CC2CCC(CC2)N)N;
Properties
Chemical formula	C13H26N2
Molar mass	210.37 g·mol−1
Appearance	colorless solid
Melting point	60–65 °C (140–149 °F; 333–338 K)
Boiling point	330–331 °C (626–628 °F; 603–604 K)
Hazards
GHS pictograms
GHS signal word	Danger
GHS hazard statements	H302, H314, H317
GHS precautionary statements	P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+312, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P314, P320, P321, P330, P333+313, P363, P391, P403+233
Flash point	153.5 °C (308.3 °F; 426.6 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

4,4-Diaminodicyclohexylmethane is the name for organic compounds with the formula CH₂(C₆H₁₀NH₂)₂. It is classified as an diamine. In the epoxy industry it is often refereed to as PACM or Para Amino diCyclohexyl Methane hence the PACM name. It is used to produce diisocyanates, which are precursors to polyurethane. The mixture is a colorless solid, but typical samples are yellowish and oily. The compound is produced as a mixture of three isomers by the hydrogenation of methylenedianiline.^[1] These isomers are, in decreasing order of their yield from the hydrogenation, trans-trans, cis-trans, and a small amount of cis-cis.^[2]

Uses

PACM is used in epoxy curing agent chemistry and other applications including construction, laminates and composites. PACM is cycloaliphatic and thus tends to have better anti yellowing and UV stability than many other amines.

Safety

It is an alkaline skin irritant. At 300 – 1000 mg/kg (oral, rats), the LD₅₀ is low. It does not exhibit mutagenic properties.

References

↑ Karsten Eller; Erhard Henkes; Roland Rossbacher; Hartmut Höke (2005). "Amines, Aliphatic". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001.
↑ Barkdoll, A. E.; Gray, H. W.; Kirk, W., Jr. (1951). "Alicyclic diamines: the geometric isomers of bis(4-aminocyclohexyl)methane". Journal of the American Chemical Society. 73: 741–6. doi:10.1021/ja01146a071.

External links[edit]

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[Ullmann-1] Karsten Eller; Erhard Henkes; Roland Rossbacher; Hartmut Höke (2005). "Amines, Aliphatic". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001.

[2] Barkdoll, A. E.; Gray, H. W.; Kirk, W., Jr. (1951). "Alicyclic diamines: the geometric isomers of bis(4-aminocyclohexyl)methane". Journal of the American Chemical Society. 73: 741–6. doi:10.1021/ja01146a071.