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]
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| Names | |
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| 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 | |
3D model (JSmol)
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| ECHA InfoCard | 100.015.608 |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| 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: | |
    
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| Danger | |
| H302, H314, H317 | |
| 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).
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Uses
editThis 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
editIt is an alkaline skin irritant. At 300 – 1000 mg/kg (oral, rats), the LD50 is low. It does not exhibit mutagenic properties.[8]
See also
editReferences
edit- ^ "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. 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. 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.