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 ; 6693-31-8 cis-cis isomer ;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.015.608
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	0NW77H1O03 ; AR21XLU05L ; B16001JGEW ; H8V09V2RM3 ;
CompTox Dashboard (EPA)	DTXSID0024921 ;
	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	210.365 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 a diamine. In the epoxy industry it is often referred to as PACM, short for para-diaminodicyclohexylmethane. It is used as a curing agent for epoxy resins[1] and 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.[2] These isomers are, in decreasing order of their yield from the hydrogenation, trans-trans, cis-trans, and a small amount of cis-cis.[3]

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

"Products & Applications: VESTAMIN® IPD, VESTAMIN® TMD, VESTAMIN® PACM" (PDF). Evonik. Retrieved January 15, 2019.
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.

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[1] "Products & Applications: VESTAMIN® IPD, VESTAMIN® TMD, VESTAMIN® PACM" (PDF). Evonik. Retrieved January 15, 2019.

[Ullmann-2] 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.

[3] 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.