1,2-Diaminocyclohexane: Difference between revisions

1,2-Diaminocyclohexane
Names
	Preferred IUPAC name Cyclohexane-1,2-diamine
Identifiers
CAS Number	694-83-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:93778;
ChEMBL	ChEMBL1356279;
ChemSpider	4449;
ECHA InfoCard	100.010.707
EC Number	211-776-7;
PubChem CID	4610;
UNII	C82TX76BHH ;
UN number	2735
CompTox Dashboard (EPA)	DTXSID0027301 ;
	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:
Pictograms
Signal word	Danger
Hazard statements	H302, H312, H314, H317, H332, H335
Precautionary 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, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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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.^[1]

Uses

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]

References

^ 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.

External links

[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). Archived (PDF) from the original on 2020-08-19.

[7] Materials, Ascend. "FlexaTram-DAM". Ascend Performance Materials. Retrieved 2020-05-21.

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@@ Line 1: / Line 1: @@
 {{Chembox
-| IUPACName = Cyclohexane-1,2-diamine
+| PIN = Cyclohexane-1,2-diamine
+| ImageFile = 1,2-Diaminocyclohexane Structural Formulae V.1.svg
 |Section1 = {{Chembox Identifiers
 | PubChem = 4610
 | CASNo = 694-83-7
+| CASNo_Ref = {{cascite|correct|CAS}}
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = C82TX76BHH
 | EC_number = 211-776-7
 | UNNumber = 2735
@@ Line 19: / Line 23: @@
 | GHSPictograms = {{GHS05}}{{GHS07}}
 | GHSSignalWord = Danger
-| HPhrases = {{H-phrases|302|312|314|317|318|332|335}}
+| HPhrases = {{H-phrases|302|312|314|317|332|335}}
 | PPhrases = {{P-phrases|260|261|264|270|271|272|280|301+312|301+330+331|302+352|303+361+353|304+312|304+340|305+351+338|310|312|321|322|330|333+313|363|403+233|405|501}}
  }}
 }}
-'''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''' ('''DACH''') is an [[organic compound]] with the formula (CH<sub>2</sub>)<sub>4</sub>(CHNH<sub>2</sub>)<sub>2</sub>. It is a mixture of three [[stereoisomers]]: ''cis''-1,2-diaminocyclohexane and both [[enantiomer]]s of [[trans-1,2-Diaminocyclohexane|''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|''o''-phenylenediamine]]. The two ''trans'' [[enantiomer]]s can be [[chiral resolution|resolved]] by conversion to [[diastereomer]]ic salts of various chiral acids.<ref>{{Cite encyclopedia|last1=Kouklovsky|first1=Cyrille|title=(1''S'',2''S'')-1,2-Diaminocyclohexane|date=2014|encyclopedia=Encyclopedia of Reagents for Organic Synthesis|pages=1–23|language=en|doi=10.1002/047084289x.rn00145.pub3|isbn=978-0-470-84289-8|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 ==
-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 poroduct 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 is particularly useful in epoxy flooring.<ref>{{Cite web|title=A New Epoxy Curing Agent with Long Pot Life and Fast Cure|url=https://www.pcimag.com/articles/96269-a-new-epoxy-curing-agent-with-long-pot-life-and-fast-cure?v=preview|access-date=2021-05-18|website=www.pcimag.com|language=en}}</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=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 |archive-date=2020-08-19 |access-date=}}</ref> It also is used in downfield oil and gas wells where there is an acidic stream to prevent corrosion to the bore piles.<ref>{{Cite web |last=Materials |first=Ascend |title=FlexaTram-DAM |url=https://www.ascendmaterials.com/specialty-chemicals/flexatram-amines/flexatram-dam/ |access-date=2020-05-21 |website=Ascend Performance Materials |language=en}}</ref>
 == See also ==
-* [[trans-1,2-Diaminocyclohexane]]
 * [[Hexamethylenediamine]]
 * [[Isophorone diamine]]
 * [[1,3-BAC]]
+* [[2,3-Butanediamine]], a vicinal diamine that also exists as three stereoisomers
 == References ==
@@ Line 45: / Line 48: @@
 == External links ==
 * [https://datasheets.globalspec.com/ds/1567/INVISTA/5D0F80C5-8C40-4033-BF35-F39A5F27E875  Engineering 360 website]
-* [https://dytek.invista.com/products/dytek-dch-99/ Invista website]
 * [https://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=132551&brand=ALDRICH&PageToGoToURL=https%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2F132551%3Flang%3Den SDS Sigma Aldrich]
-* [https://www.gracoroberts.com/home/download/invista-dytek-dch-99-amine-epoxy-coating-sds/ Safety Data Sheet]
-<!--- Categories --->
+{{DEFAULTSORT:Diaminocyclohexane, 1,2-}}
 [[Category:Diamines]]
+[[Category:Cycloalkylamines]]