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'''1,2-Cyclohexanediamine''' is an organic compound with the formula (CH<sub>2</sub>)<sub>4</sub>(CHNH<sub>2</sub>)<sub>2</sub>. Described by the registry number [[CAS Registry number]] (RN) 694-83-7 is a mixture of the two [[diastereoisomer]]s, [[trans-1,2-Diaminocyclohexane|''trans''-1,2-diaminocyclohexane]] (RN 1121-22-8) and ''cis''-1,2-diaminocyclohexane (RN 1436-59-5). The mixture is a colorless, corrosive liquid.<ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/4610|title=1,2-Cyclohexanediamine|last=PubChem|website=pubchem.ncbi.nlm.nih.gov|language=en|access-date=2020-04-13}}</ref>. It is often called DCH-99 and also DACH.
'''1,2-Diaminocyclohexane''' is an [[organic compound]] with the formula (CH<sub>2</sub>)<sub>4</sub>(CHNH<sub>2</sub>)<sub>2</sub>. Described by the registry number [[CAS Registry number]] (RN) 694-83-7, it is a mixture of the two [[diastereoisomer]]s, [[trans-1,2-Diaminocyclohexane|''trans''-1,2-diaminocyclohexane]] (RN 1121-22-8) and ''cis''-1,2-diaminocyclohexane (RN 1436-59-5). The mixture is a colorless, corrosive liquid, although older samples can appear yellow. It is often called DCH-99 and also DACH.


== Manufacture ==
== Manufacture ==
⚫
The product is available commercially as Dytek DCH-99. It is manufactured by the [[hydrogenation]] of [[o-phenylenediamine]]<ref>{{Citation|last=Kouklovsky|first=Cyrille|title=(1S,2S)-1,2-Diaminocyclohexane|date=2014|url=https://onlinelibrary.wiley.com/doi/abs/10.1002/047084289X.rn00145.pub3|work=Encyclopedia of Reagents for Organic Synthesis|pages=1–23|publisher=American Cancer Society|language=en|doi=10.1002/047084289x.rn00145.pub3|isbn=978-0-470-84289-8|access-date=2020-04-13|last2=Langlois|first2=Yves|last3=Aguilar|first3=Enrique|last4=Fernández‐García|first4=Jesús M.|last5=Sikervar|first5=Vikas}}</ref>.

⚫
The product is available commercially as Dytek DCH-99. It may be manufactured by the [[hydrogenation]] of [[o-phenylenediamine]]<ref>{{Citation|last=Kouklovsky|first=Cyrille|title=(1S,2S)-1,2-Diaminocyclohexane|date=2014|url=https://onlinelibrary.wiley.com/doi/abs/10.1002/047084289X.rn00145.pub3|work=Encyclopedia of Reagents for Organic Synthesis|pages=1–23|publisher=American Cancer Society|language=en|doi=10.1002/047084289x.rn00145.pub3|isbn=978-0-470-84289-8|access-date=2020-04-13|last2=Langlois|first2=Yves|last3=Aguilar|first3=Enrique|last4=Fernández‐García|first4=Jesús M.|last5=Sikervar|first5=Vikas}}</ref>.


== Uses ==
== Uses ==
The product is used in the production of epoxy curing agents for use in [[Coatings]], [[Adhesives]], [[Sealants]] and [[Elastomers]] - CASE<ref>{{Cite web|url=https://www.ulprospector.com/en/la/Coatings/Detail/25290/557016/Dytek-DCH-99|title=Dytek® DCH-99 by INVISTA - Paint & Coatings|website=www.ulprospector.com|access-date=2020-04-13}}</ref>. It may also be reacted with diethyl maleate utilizing the [[Michael reaction]] to produce a [[polyaspartic]] compound<ref>{{Cite web|url=https://dytek.invista.com/products/dytek-dch-99/|title=Dytek® DCH-99 {{!}} 1,2-Diaminocyclohexane|website=Dytek|language=en-US|access-date=2020-04-13}}</ref> of CAS number 481040-92-0. It may also be used in lubricants<ref>{{Cite web|url=https://patents.justia.com/patent/9273266|title=US Patent for Non-aromatic based antioxidants for lubricants Patent (Patent # 9,273,266 issued March 1, 2016) - Justia Patents Search|website=patents.justia.com|access-date=2020-04-13}}</ref>. The product is also advertised as being useful as a [[chelating agent]] in a variety of applications including oil production<ref>{{Cite web|url=https://dytek.invista.com/wp-content/uploads/2018/07/Dytek%E2%94%AC%C2%AB-DCH-99-12-Diaminocyclohexane-Technical-Data-Sheet.pdf|title=Technical Data Sheet Dytek DCH 99|last=|first=|date=|website=|url-status=live|archive-url=|archive-date=|access-date=}}</ref>.
The product is an epoxy curing agent for use in [[Coatings]], [[Adhesives]], [[Sealants]] and [[Elastomers]] - CASE.<ref>{{Cite web|url=https://www.ulprospector.com/en/la/Coatings/Detail/25290/557016/Dytek-DCH-99|title=Dytek® DCH-99 by INVISTA - Paint & Coatings|website=www.ulprospector.com|access-date=2020-04-13}}</ref> It may also be reacted with diethyl maleate utilizing the [[Michael reaction]] to produce a [[polyaspartic]] compound of CAS number 481040-92-0.<ref>{{Cite web|url=https://dytek.invista.com/products/dytek-dch-99/|title=Dytek® DCH-99 {{!}} 1,2-Diaminocyclohexane|website=Dytek|language=en-US|access-date=2020-04-13}}</ref> It may also be used in lubricants<ref>{{Cite web|url=https://patents.justia.com/patent/9273266|title=US Patent for Non-aromatic based antioxidants for lubricants Patent (Patent # 9,273,266 issued March 1, 2016) - Justia Patents Search|website=patents.justia.com|access-date=2020-04-13}}</ref>. The product is also advertised as being useful as a [[chelating agent]] in a variety of applications including oil production.<ref>{{Cite web|url=https://dytek.invista.com/wp-content/uploads/2018/07/Dytek%E2%94%AC%C2%AB-DCH-99-12-Diaminocyclohexane-Technical-Data-Sheet.pdf|title=Technical Data Sheet Dytek DCH 99|last=|first=|date=|website=|url-status=live|archive-url=|archive-date=|access-date=}}</ref>


== See also ==
== See also ==

Revision as of 11:19, 13 May 2020

1,2-Diaminocyclohexane
Names
IUPAC name
Cyclohexane-1,2-diamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.010.707 Edit this at Wikidata
EC Number
  • 211-776-7
UN number 2735
  • 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:
GHS05: CorrosiveGHS07: Exclamation mark
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).

1,2-Diaminocyclohexane is an organic compound with the formula (CH2)4(CHNH2)2. Described by the registry number CAS Registry number (RN) 694-83-7, it is a mixture of the two diastereoisomers, trans-1,2-diaminocyclohexane (RN 1121-22-8) and cis-1,2-diaminocyclohexane (RN 1436-59-5). 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 as Dytek DCH-99. It is manufactured by the hydrogenation of o-phenylenediamine[1].

Uses

The product is an epoxy curing agent for use in Coatings, Adhesives, Sealants and Elastomers - CASE.[2] It may also be reacted with diethyl maleate utilizing the Michael reaction to produce a polyaspartic compound of CAS number 481040-92-0.[3] It may also be used in lubricants[4]. The product is also advertised as being useful as a chelating agent in a variety of applications including oil production.[5]

See also

References

  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, American Cancer Society, pp. 1–23, doi:10.1002/047084289x.rn00145.pub3, ISBN 978-0-470-84289-8, retrieved 2020-04-13
  2. ^ "Dytek® DCH-99 by INVISTA - Paint & Coatings". www.ulprospector.com. Retrieved 2020-04-13.
  3. ^ "Dytek® DCH-99 | 1,2-Diaminocyclohexane". Dytek. Retrieved 2020-04-13.
  4. ^ "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.
  5. ^ "Technical Data Sheet Dytek DCH 99" (PDF).{{cite web}}: CS1 maint: url-status (link)
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