1,2-Diaminocyclohexane

1,2-Diaminocyclohexane
Names
Preferred IUPAC name
Cyclohexane-1,2-diamine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.010.707
EC Number
  • 211-776-7
PubChem CID
UNII
UN number 2735
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2
    Key: SSJXIUAHEKJCMH-UHFFFAOYSA-N
SMILES
  • C1CCC(C(C1)N)N
Properties
Chemical formula
 C6H14N2
Molar mass 114.192 g·mol−1
Hazards
GHS labelling:[1]
Pictograms
 GHS05: CorrosiveGHS07: Exclamation mark
Signal word
 Danger
Hazard statements
 H302, H302+H312+H332, H312, H314, H317, H332, H335
Precautionary statements
 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.[2]

Uses

The product is an epoxy curing agent for use in Coatings, Adhesives, Sealants and Elastomers - CASE.[3] It is particularly useful in epoxy flooring.[4] It may also be reacted with diethyl maleate utilizing the Michael reaction to produce a polyaspartic compound of CAS number 481040-92-0.[5] It may also be used in lubricants.[6] The product is also advertised as being useful as a chelating agent in a variety of applications including oil production.[7] It also is used in downfield oil and gas wells where there is an acidic stream to prevent corrosion to the bore piles.[8]

See also

References

  1. ^ "1,2-Diaminocyclohexane". pubchem.ncbi.nlm.nih.gov.
  2. ^ 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.
  3. ^ "Dytek DCH-99 by INVISTA - Paint & Coatings". www.ulprospector.com. Retrieved 2020-04-13.
  4. ^ "A New Epoxy Curing Agent with Long Pot Life and Fast Cure". www.pcimag.com. Retrieved 2021-05-18.
  5. ^ "Dytek DCH-99 | 1,2-Diaminocyclohexane". Dytek. Retrieved 2020-04-13.
  6. ^ "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.
  7. ^ "Technical Data Sheet Dytek DCH 99" (PDF). Archived (PDF) from the original on 2020-08-19.
  8. ^ Materials, Ascend. "FlexaTram-DAM". Ascend Performance Materials. Retrieved 2020-05-21.
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