1,2-Diaminocyclohexane (DACH) is an organic compound with the formula (CH2)4(CHNH2)2. It is a mixture of three stereoisomers: cis-1,2-diaminocyclohexane and both enantiomers of trans-1,2-diaminocyclohexane. The mixture is a colorless, corrosive liquid, although older samples can appear yellow. It is often called DCH-99 and also DACH.
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| Names | |
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| Preferred IUPAC name
Cyclohexane-1,2-diamine | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.010.707 |
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PubChem CID
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| UNII | |
| UN number | 2735 |
CompTox Dashboard (EPA)
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| Properties | |
| C6H14N2 | |
| Molar mass | 114.192 g·mol−1 |
| Hazards | |
| GHS labelling: | |
 
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| Danger | |
| H302, H312, H314, H317, H332, H335 | |
| P260, P261, P264, P270, P271, P272, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P333+P313, P363, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Manufacture
editThe product is available commercially, manufactured by the hydrogenation of o-phenylenediamine. The two trans enantiomers can be resolved by conversion to diastereomeric salts of various chiral acids.[1]
Uses
editThe product is an epoxy curing agent for use in Coatings, Adhesives, Sealants and Elastomers - CASE.[2] It is particularly useful in epoxy flooring.[3] It may also be reacted with diethyl maleate utilizing the Michael reaction to produce a polyaspartic compound of CAS number 481040-92-0.[4] It may also be used in lubricants.[5] The product is also advertised as being useful as a chelating agent in a variety of applications including oil production.[6] It also is used in downfield oil and gas wells where there is an acidic stream to prevent corrosion to the bore piles.[7]
See also
edit- Hexamethylenediamine
- Isophorone diamine
- 1,3-BAC
- 2,3-Butanediamine, a vicinal diamine that also exists as three stereoisomers
References
edit- ^ Kouklovsky, Cyrille; Langlois, Yves; Aguilar, Enrique; Fernández-García, Jesús M.; Sikervar, Vikas (2014). "(1S,2S)-1,2-Diaminocyclohexane". Encyclopedia of Reagents for Organic Synthesis. pp. 1–23. doi:10.1002/047084289x.rn00145.pub3. ISBN 978-0-470-84289-8.
- ^ "Dytek DCH-99 by INVISTA - Paint & Coatings". www.ulprospector.com. Retrieved 2020-04-13.
- ^ "A New Epoxy Curing Agent with Long Pot Life and Fast Cure". www.pcimag.com. Retrieved 2021-05-18.
- ^ "Dytek DCH-99 | 1,2-Diaminocyclohexane". Dytek. Retrieved 2020-04-13.
- ^ "US Patent for Non-aromatic based antioxidants for lubricants Patent (Patent # 9,273,266 issued March 1, 2016) - Justia Patents Search". patents.justia.com. Retrieved 2020-04-13.
- ^ "Technical Data Sheet Dytek DCH 99" (PDF). Archived (PDF) from the original on 2020-08-19.
- ^ Materials, Ascend. "FlexaTram-DAM". Ascend Performance Materials. Retrieved 2020-05-21.