4,4'-Diaminodicyclohexylmethane

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]

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
3D model (JSmol)
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)
UNII
  • 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
  • C1CC(CCC1CC2CCC(CC2)N)N
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:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
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).
Infobox references

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]

See also

References
  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.
  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. doi:10.1021/ja01146a071.
  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. 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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