4,4'-Diaminodicyclohexylmethane

4,4'-Diaminodicyclohexylmethane
Names
	Preferred IUPAC name 4,4'-Methylenedi(cyclohexan-1-amine)
	Other names 4,4'-Methylenebis(cyclohexan-1-amine); 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;
ChemSpider	13868371;
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 labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H314, H317
Precautionary statements	P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P314, P320, P321, P330, P333+P313, P363, P391, P403+P233, P405, P501
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] It finds particular use in epoxy flooring.^[2] Another use is to produce diisocyanates, which are precursors to polyurethanes. 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.^[3] These isomers are, in decreasing order of their yield from the hydrogenation, trans-trans, cis-trans, and a small amount of cis-cis.^[4]

Uses

This diamine is mainly used to make epoxy resin curing agents for CASE (Coatings, Adhesives, Sealants, and Elastomers) applications especially flooring.^[5] Another application arises from its reaction with phosgene to produce a cycloaliphatic diisocyanate Hydrogenated MDI, which is used to produce light stable polyurethanes. The substance may also be used as a chemical intermediate to make other molecules.^[6]

4,4'-Diaminodicyclohexylmethane was used in producing a polyamide called Qiana, since discontinued. For this application, the condensation partner was dodecanoic acid.^[7]

Safety

It is an alkaline skin irritant. At 300 – 1000 mg/kg (oral, rats), the LD₅₀ is low. It does not exhibit mutagenic properties.^[8]

References

^ "Products & Applications: VESTAMIN® IPD, VESTAMIN® TMD, VESTAMIN® PACM" (PDF). Evonik. Retrieved January 15, 2019.
^ "A New Epoxy Curing Agent with Long Pot Life and Fast Cure". www.pcimag.com. Retrieved 2021-05-18.
^ 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. ISBN 3527306730.
^ 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 (2): 741–6. Bibcode:1951JAChS..73..741B. doi:10.1021/ja01146a071.{{cite journal}}: CS1 maint: numeric names: authors list (link)
^ Huang, Yizhou; Tian, Yazhou; Li, Yuanyuan; Tan, Xiaocun; Li, Qing; Cheng, Jue; Zhang, Junying (2017-10-16). "High mechanical properties of epoxy networks with dangling chains and tunable microphase separation structure". RSC Advances. 7 (77): 49074–49082. Bibcode:2017RSCAd...749074H. doi:10.1039/C7RA08886H. ISSN 2046-2069.
^ Gawdzik, Barbara; Kovtun, Oksana (2005-12-15). "Synthesis of glycidyl amine adducts and their copolymerization with glycidyl methacrylate". Journal of Applied Polymer Science. 98 (6): 2461–2466. doi:10.1002/app.22444. ISSN 0021-8995.
^ Estes, Leland L.; Schweizer, Michael (2011). "Fibers, 4. Polyamide Fibers". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a10_567.pub2. ISBN 978-3527306732.
^ PubChem. "4,4'-Methylenedicyclohexanamine". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-12-05.

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

[2] "A New Epoxy Curing Agent with Long Pot Life and Fast Cure". www.pcimag.com. Retrieved 2021-05-18.

[Ullmann-3] 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. ISBN 3527306730.

[4] 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 (2): 741–6. Bibcode:1951JAChS..73..741B. doi:10.1021/ja01146a071.{{cite journal}}: CS1 maint: numeric names: authors list (link)

[5] Huang, Yizhou; Tian, Yazhou; Li, Yuanyuan; Tan, Xiaocun; Li, Qing; Cheng, Jue; Zhang, Junying (2017-10-16). "High mechanical properties of epoxy networks with dangling chains and tunable microphase separation structure". RSC Advances. 7 (77): 49074–49082. Bibcode:2017RSCAd...749074H. doi:10.1039/C7RA08886H. ISSN 2046-2069.

[6] Gawdzik, Barbara; Kovtun, Oksana (2005-12-15). "Synthesis of glycidyl amine adducts and their copolymerization with glycidyl methacrylate". Journal of Applied Polymer Science. 98 (6): 2461–2466. doi:10.1002/app.22444. ISSN 0021-8995.

[7] Estes, Leland L.; Schweizer, Michael (2011). "Fibers, 4. Polyamide Fibers". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a10_567.pub2. ISBN 978-3527306732.

[8] PubChem. "4,4'-Methylenedicyclohexanamine". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-12-05.

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Uses

Safety

See also

References