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1,2-Diaminocyclohexane

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.

1,2-Diaminocyclohexane
Names
Preferred IUPAC name
Cyclohexane-1,2-diamine
Identifiers
  • 694-83-7 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:93778
ChEMBL
  • ChEMBL1356279
ChemSpider
  • 4449
ECHA InfoCard 100.010.707
EC Number
  • 211-776-7
  • 4610
UNII
  • C82TX76BHH Y
UN number 2735
  • DTXSID0027301
  • InChI=1S/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2
    Key: SSJXIUAHEKJCMH-UHFFFAOYSA-N
  • C1CCC(C(C1)N)N
Properties
C6H14N2
Molar mass 114.192 g·mol−1
Hazards
GHS labelling:
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).

Manufacture Edit

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.[1]

Uses Edit

The 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

References Edit

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

External links Edit

  • Engineering 360 website
  • SDS Sigma Aldrich

diaminocyclohexane, dach, organic, compound, with, formula, chnh2, mixture, three, stereoisomers, diaminocyclohexane, both, enantiomers, trans, diaminocyclohexane, mixture, colorless, corrosive, liquid, although, older, samples, appear, yellow, often, called, . 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 1 2 Diaminocyclohexane NamesPreferred IUPAC name Cyclohexane 1 2 diamineIdentifiersCAS Number 694 83 7 Y3D model JSmol Interactive imageChEBI CHEBI 93778ChEMBL ChEMBL1356279ChemSpider 4449ECHA InfoCard 100 010 707EC Number 211 776 7PubChem CID 4610UNII C82TX76BHH YUN number 2735CompTox Dashboard EPA DTXSID0027301InChI InChI 1S C6H14N2 c7 5 3 1 2 4 6 5 8 h5 6H 1 4 7 8H2Key SSJXIUAHEKJCMH UHFFFAOYSA NSMILES C1CCC C C1 N NPropertiesChemical formula C 6H 14N 2Molar mass 114 192 g mol 1HazardsGHS labelling PictogramsSignal word DangerHazard statements H302 H312 H314 H317 H332 H335Precautionary statements 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 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Manufacture 2 Uses 3 See also 4 References 5 External linksManufacture 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 EditHexamethylenediamine Isophorone diamine 1 3 BAC PACMReferences Edit Kouklovsky Cyrille Langlois Yves Aguilar Enrique Fernandez Garcia Jesus 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 amp 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 External links EditEngineering 360 website SDS Sigma Aldrich Retrieved from https en wikipedia org w index php title 1 2 Diaminocyclohexane amp oldid 1172312705, wikipedia, wiki, book, books, library,

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