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4,4'-Diaminodicyclohexylmethane

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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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.608 Edit this at Wikidata
EC Number
  • 217-168-8 (mixture), 229-737-8 (trans-trans), 229-738-3 (trans-cis), 229-739-9 (cis-cis)
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C13H26N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h10-13H,1-9,14-15H2Key: DZIHTWJGPDVSGE-UHFFFAOYSA-N
SMILES
  • C1CC(CCC1CC2CCC(CC2)N)N
Properties
Chemical formula C13H26N2
Molar mass 210.365 g·mol
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 GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
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 , 100 kPa). Infobox references
Chemical compound

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 It finds particular use in epoxy flooring. 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. These isomers are, in decreasing order of their yield from the hydrogenation, trans-trans, cis-trans, and a small amount of cis-cis.

Uses

This diamine is mainly used to make epoxy resin curing agents for CASE (Coatings, Adhesives, Sealants, and Elastomers) applications especially flooring. 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.

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

Safety

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

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. 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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