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1,2-Diaminocyclohexane
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Cyclohexane-1,2-diamine 1,2-Diaminocyclohexane Structural Formulae V.1.svg 4610 694-83-7 correct CAS correct FDA C82TX76BHH 211-776-7 2735 1356279 93778 4449 1S/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2 SSJXIUAHEKJCMH-UHFFFAOYSA-N C1CCC(C(C1)N)N
6 14 2
1,2-Diaminocyclohexane https://pubchem.ncbi.nlm.nih.gov/compound/4610#section=Safety-and-Hazards pubchem.ncbi.nlm.nih.gov 05 07 Danger H302+H312+H332 H302 H312 H314 H317 H332 H335 P260 P264 P264+P265 P270 P271 P272 P280 P301+P317 P301+P330+P331 P302+P352 P302+P361+P354 P304+P340 P305+P354+P338 P316 P317 P319 P321 P330 P333+P317 P362+P364 P363 P403+P233 P405 P501
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.
Manufacture
The 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.Kouklovsky Cyrille (1S,2S)-1,2-Diaminocyclohexane 2014 Encyclopedia of Reagents for Organic Synthesis 1–23 en 10.1002/047084289x.rn00145.pub3 978-0-470-84289-8 Langlois Yves Aguilar Enrique Fernández-García Jesús M. Sikervar Vikas
Uses
The product is an epoxy curing agent for use in Coatings, Adhesives, Sealants and Elastomers - CASE.https://www.ulprospector.com/en/la/Coatings/Detail/25290/557016/Dytek-DCH-99 Dytek DCH-99 by INVISTA - Paint & Coatings www.ulprospector.com 2020-04-13 It is particularly useful in epoxy flooring.A New Epoxy Curing Agent with Long Pot Life and Fast Cure https://www.pcimag.com/articles/96269-a-new-epoxy-curing-agent-with-long-pot-life-and-fast-cure?v=preview 2021-05-18 www.pcimag.com en It may also be reacted with diethyl maleate utilizing the Michael reaction to produce a polyaspartic compound of CAS number 481040-92-0.https://dytek.invista.com/products/dytek-dch-99/ Dytek DCH-99 1,2-Diaminocyclohexane Dytek en-US 2020-04-13 It may also be used in lubricants.https://patents.justia.com/patent/9273266 US Patent for Non-aromatic based antioxidants for lubricants Patent (Patent # 9,273,266 issued March 1, 2016) - Justia Patents Search patents.justia.com 2020-04-13 The product is also advertised as being useful as a chelating agent in a variety of applications including oil production.https://dytek.invista.com/wp-content/uploads/2018/07/Dytek%E2%94%AC%C2%AB-DCH-99-12-Diaminocyclohexane-Technical-Data-Sheet.pdf Technical Data Sheet Dytek DCH 99 live https://web.archive.org/web/20200819211521/https://dytek.invista.com/wp-content/uploads/2018/07/Dytek%E2%94%AC%C2%AB-DCH-99-12-Diaminocyclohexane-Technical-Data-Sheet.pdf 2020-08-19 It also is used in downfield oil and gas wells where there is an acidic stream to prevent corrosion to the bore piles.Materials Ascend FlexaTram-DAM https://www.ascendmaterials.com/specialty-chemicals/flexatram-amines/flexatram-dam/ 2020-05-21 Ascend Performance Materials en
See also
Hexamethylenediamine
Isophorone diamine
1,3-BAC
2,3-Butanediamine, a vicinal diamine that also exists as three stereoisomers
References
External links
Engineering 360 website
SDS Sigma Aldrich
Category:Diamines
Category:Cycloalkylamines