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	{{chembox		{{Chembox
			|Verifiedfields = changed
	| verifiedrevid = 390297245
			|Watchedfields = changed
	| Reference = <ref>''Merck Index'', 11th Edition, '''4614'''.</ref><ref></ref>
			|verifiedrevid = 397772053
	| ImageFile = 1,6-diaminohexane-2D-skeletal.svg
			|Reference = <ref>''Merck Index'', 11th Edition, '''4614'''.</ref><ref></ref>
	| ImageSize = 200px
	| ImageFile1 = 1,6-diaminohexane-3D-balls.png		|ImageFile = 1,6-diaminohexane-2D-skeletal.svg
			|ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageSize1 = 200px
			|ImageName = Skeletal formula of hexamethylenediamine
	| IUPACName = Hexane-1,6-diamine
	| OtherNames = 1,6-diaminohexane, 1,6-hexanediamine		|ImageFile1 = 1,6-diaminohexane-3D-balls.png
			|ImageFile1_Ref = {{chemboximage|correct|??}}
	| Section1 = {{Chembox Identifiers
			|ImageName1 = Ball and stick model of hexamethylenediamine
	| Abbreviations =
			|ImageFile2 = 1,6-diaminohexane-3D-vdW.png
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			|ImageFile2_Ref = {{chemboximage|correct|??}}
	| ChemSpiderID = 15555
			|ImageName2 = Spacefill model of hexamethylenediamine
	| CASNo_Ref = {{cascite|correct|CAS}}
			|PIN = Hexane-1,6-diamine<ref>{{Cite web|title=1,6-diaminohexane - Compound Summary |url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16402&loc=ec_rcs#x291|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=29 May 2012|location=USA|date=26 March 2005|at=Identification and Related Records}}</ref>
	| CASNo = 124-09-4
			|OtherNames = {{Unbulleted list|1,6-Diaminohexane|1,6-Hexanediamine
	| EINECS =
	| UNNumber = 1783 (solution), 2280 (solid)
	| PubChem = 16402
	| SMILES = NCCCCCCN
	| InChI =
	| RTECS =
	| MeSHName =
	| ChEBI =
	| KEGG =
	| ATCCode_prefix =
	| ATCCode_suffix =
	| ATC_Supplemental =}}
	| Section2 = {{Chembox Properties
	| Formula = C<sub>6</sub>H<sub>16</sub>N<sub>2</sub>
	| MolarMass = 116.21 g/mol
	| Appearance = White crystals or powder
	| Density = 0.84 g/cm<sup>3</sup>
	| MeltingPtC = 42
	| Melting_notes =
	| BoilingPtC = 205
	| Boiling_notes =
	| Solubility = 960 g/100 mL
	| SolubleOther =
	| Solvent =
	| pKa = 10.0, 11.1
	| pKb = }}
	| Section7 = {{Chembox Hazards
	| EUClass =
	| EUIndex =
	| MainHazards = Toxic, Corrosive
	| NFPA-H = 3
	| NFPA-F = 2
	| NFPA-R = 0
	| NFPA-O =
	| RPhrases = {{R20}} {{R22}} {{R34}} {{R36}} {{R37}} {{R38}}
	| SPhrases =
	| RSPhrases =
	| FlashPt = 93 °C (102 °C for 90% aq. soln)
	| Autoignition =
	| ExploLimits = 0.7 - 6.3 %
	| PEL = }}
	}}		}}
			|Section1={{Chembox Identifiers
	'''Hexamethylenediamine''' is the ] with the formula H<sub>2</sub>N(CH<sub>2</sub>)<sub>6</sub>NH<sub>2</sub>. The molecule is a ], consisting of a ] ] chain terminated with ] ]s. The colorless solid (yellowish for some commercial samples) has a strong amine odor, similar to ]. About 1 billion kilograms are produced annually.<ref name=Ullmann>Robert A. Smiley "Hexamethylenediamine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. {{DOI|10.1002/14356007.a12 629}}</ref>
			|CASNo = 124-09-4
			|CASNo_Ref = {{cascite|correct|CAS}}
			|UNII_Ref = {{fdacite|correct|FDA}}
			|UNII = ZRA5J5B2QW
			|PubChem = 16402
			|ChemSpiderID = 13835579
			|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			|EINECS = 204-679-6
			|UNNumber = 2280
			|DrugBank = DB03260
			|DrugBank_Ref = {{drugbankcite|changed|drugbank}}
			|MeSHName = 1,6-diaminohexane
			|ChEBI = 39618
			|ChEBI_Ref = {{ebicite|changed|EBI}}
			|ChEMBL = 303004
			|ChEMBL_Ref = {{ebicite|changed|EBI}}
			|RTECS = MO1180000
			|Beilstein = 1098307
			|Gmelin = 2578
			|SMILES = NCCCCCCN
			|StdInChI = 1S/C6H16N2/c7-5-3-1-2-4-6-8/h1-8H2
			|StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			|StdInChIKey = NAQMVNRVTILPCV-UHFFFAOYSA-N
			|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			}}
			|Section2={{Chembox Properties
			|C=6 | H=16 | N=2
			|Appearance = Colourless crystals
			|Density = 0.84 g/mL
			|MeltingPtC = 39 to 42
			|BoilingPtK = 477.7
			|Solubility = 490 g L<sup>−1</sup>
			|LogP = 0.386
			}}
			|Section3={{Chembox Thermochemistry
			|DeltaHf = −205 kJ mol<sup>−1</sup>
			}}
			|Section4={{Chembox Hazards
			|GHSPictograms = {{GHS corrosion}} {{GHS exclamation mark}}
			|GHSSignalWord = '''DANGER'''
			|HPhrases = {{H-phrases|302|312|314|335}}
			|PPhrases = {{P-phrases|261|280|305+351+338|310}}
			|NFPA-H = 3
			|NFPA-F = 2
			|NFPA-R = 0
			|FlashPtC = 80
			|ExploLimits = 0.7–6.3%
			|LD50 = {{Unbulleted list|750 mg kg<sup>−1</sup> <small>(oral, rat)</small>|1.11 g kg<sup>−1</sup> <small>(dermal, rabbit)</small>}}
			}}
			|Section5={{Chembox Related
			|OtherFunction_label = alkanamines
			|OtherFunction = {{Unbulleted list|]|]|]|]}}
			}}
			}}
			'''Hexamethylenediamine''' or '''hexane-1,6-diamine''', is the ] with the formula H<sub>2</sub>N(CH<sub>2</sub>)<sub>6</sub>NH<sub>2</sub>. The molecule is a ], consisting of a ] ] chain terminated with ] ]s. The colorless solid (yellowish for some commercial samples) has a strong amine odor. About 1 billion kilograms are produced annually.<ref name=Ullmann>Robert A. Smiley "Hexamethylenediamine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. {{doi|10.1002/14356007.a12_629}}</ref>
	==Synthesis==		==Synthesis==
	Hexamethylenediamine was first reported by ].<ref>T. Curtius et al. J. Prakt. Chem., 1900, volume 62, p. 189.</ref> It is presently produced by the hydrogenation of ]:		Hexamethylenediamine was first reported by ].<ref>Curtius, Theodor and Clemm, Hans (1900) (Synthesis of 1,3-diaminopropane and 1,6-diaminohexane from glutaric acid and suberic acid, respectively), ''Journal für praktische Chemie'', 2nd series, '''62''' : 189–211.</ref> It is produced by the hydrogenation of ]:
	:NC(CH<sub>2</sub>)<sub>4</sub>CN + 4 H<sub>2</sub> → H<sub>2</sub>N(CH<sub>2</sub>)<sub>6</sub>NH<sub>2</sub>		:NC(CH<sub>2</sub>)<sub>4</sub>CN + 4 H<sub>2</sub> → H<sub>2</sub>N(CH<sub>2</sub>)<sub>6</sub>NH<sub>2</sub>
	The hydrogenation is conducted molten ] diluted with ], typical catalysts being based on ] and ]. The yield is good, but commercially significant side products are generated by virtue of reactivity of partially hydrogenated intermediates. These other products include ], hexamethyleneimine, and the triamine bis(hexamethylenetriamine).<ref name=Ullmann/>		The hydrogenation is conducted on molten ] diluted with ],<ref>{{Cite web|url=https://ihsmarkit.com/products/SRICReport-Report31C-AdvancesinAdiponitrileADNandHexamethylenediamineHMDAProcesses.html|title=SRIC Report - Report 31C - Advances in Adiponitrile (ADN) and Hexamethylenediamine (HMDA) Processes {{!}} IHS Markit|website=ihsmarkit.com|access-date=2019-02-19}}</ref> typical catalysts being based on ] and ]. The yield is good, but commercially significant side products are generated by virtue of reactivity of partially hydrogenated intermediates. These other products include ], ], and the triamine bis(hexamethylenetriamine).
			An alternative process uses ] as the catalyst and adiponitrile that is diluted with hexamethylenediamine itself (as the solvent). This process operates without ammonia and at lower pressure and temperature.<ref name=Ullmann/>
	==Applications==		==Applications==
			Hexamethylenediamine is used almost exclusively for the production of ]s, an application that takes advantage of its structure.<ref>{{Cite journal |last1=Longseng |first1=Rutchanon |last2=Khaokong |first2=Chuanpit |date=2020-12-01 |title=Hexamethylene diamine-modified epoxidized natural rubber and its effect on cure characteristics and properties of natural rubber blends |url=https://doi.org/10.1007/s13726-020-00865-x |journal=Iranian Polymer Journal |language=en |volume=29 |issue=12 |pages=1113–1121 |doi=10.1007/s13726-020-00865-x |s2cid=221824894 |issn=1735-5265}}</ref><ref>{{Cite journal |last1=Hu |first1=Juncheng |last2=Feng |first2=Xia |last3=Liu |first3=Zhengyi |last4=Zhao |first4=Yiping |last5=Chen |first5=Li |date=July 2017 |title=Surface amine-functionalization of UHMWPE fiber by bio-inspired polydopamine and grafted hexamethylene diamine: Surface amine-functionalization of UHMWPE fiber by PDA and HMDA |url=https://onlinelibrary.wiley.com/doi/10.1002/sia.6203 |journal=Surface and Interface Analysis |language=en |volume=49 |issue=7 |pages=640–646 |doi=10.1002/sia.6203|s2cid=99804759 }}</ref> It is difunctional in terms of the amine groups and tetra functional with respect to the amine hydrogens. The great majority of the diamine is consumed by the production of ] via condensation with ]. Otherwise ] (HDI) is generated from this diamine by ] as a monomer feedstock in the production of ].<ref>{{Cite journal |last1=Kim |first1=C. K. |last2=Kim |first2=B. K. |last3=Jeong |first3=H. M. |date=1991-09-01 |title=Aqueous dispersion of polyurethane ionomers from hexamethylene diisocyanate and trimellitic anhydride |url=https://doi.org/10.1007/BF00657306 |journal=Colloid and Polymer Science |language=en |volume=269 |issue=9 |pages=895–900 |doi=10.1007/BF00657306 |s2cid=94481368 |issn=1435-1536}}</ref><ref>{{Cite journal |last1=Hu |first1=Jin |last2=Chen |first2=Zhuo |last3=He |first3=Yong |last4=Huang |first4=Hong |last5=Zhang |first5=Xinya |date=2017-05-01 |title=Synthesis and structure investigation of hexamethylene diisocyanate (HDI)-based polyisocyanates |url=https://doi.org/10.1007/s11164-016-2795-1 |journal=Research on Chemical Intermediates |language=en |volume=43 |issue=5 |pages=2799–2816 |doi=10.1007/s11164-016-2795-1 |s2cid=100565578 |issn=1568-5675}}</ref> The diamine also serves as a ]ing agent in ]s.<ref>{{Cite journal |last1=Luňák |first1=S. |last2=Dušek |first2=K. |date=2007-03-08 |title=Curing of epoxy resins. II. Curing of bisphenol a diglycidyl ether with diamines |url=https://onlinelibrary.wiley.com/doi/10.1002/polc.5070530108 |journal=Journal of Polymer Science: Polymer Symposia |language=en |volume=53 |issue=1 |pages=45–55 |doi=10.1002/polc.5070530108}}</ref><ref>{{Cite journal |last1=Dušek |first1=K. |last2=Pleštil |first2=J. |last3=Lednický |first3=F. |last4=Luňák |first4=S. |date=1978-04-01 |title=Are cured epoxy resins inhomogeneous? |url=https://dx.doi.org/10.1016/0032-3861%2878%2990243-4 |journal=Polymer |language=en |volume=19 |issue=4 |pages=393–397 |doi=10.1016/0032-3861(78)90243-4 |issn=0032-3861}}</ref><ref>{{Cite journal |last1=Lainioti |first1=Georgia Ch. |last2=Savva |first2=Panagiota |last3=Druvari |first3=Denisa |last4=Avramidis |first4=Pavlos |last5=Panagiotaras |first5=Dionisios |last6=Karellou |first6=Eva Iris Eleftheria |last7=Kallitsis |first7=Joannis K. |date=2021-08-01 |title=Cross-linking of antimicrobial polymers with hexamethylene diamine to prevent biofouling in marine applications |url=https://www.sciencedirect.com/science/article/pii/S0300944021002071 |journal=Progress in Organic Coatings |language=en |volume=157 |pages=106336 |doi=10.1016/j.porgcoat.2021.106336 |s2cid=236243177 |issn=0300-9440}}</ref>
	Hexamethylenediamine is used almost exclusively for the production of ]s, an application that takes advantage of its bifunctional structure. The great majority of the diamine is consumed by the production of ] via condensation with ]. Otherwise ] (HDI) is generated from this diamine as a monomer feedstock in the production of ]. The diamine also serves as a ]ing agent in ]s.
	==Safety==		==Safety==
	Hexamethylenediamine is moderately toxic, with {{LD50}} of 792-1127 mg/kg.<ref name=Ullmann/> Nonetheless, like other basic amines, it can cause serious burns and severe irritation. Such injuries were observed in the accident at the ] site in ], near ] (UK) on 4 January, 2007. 37 injured and 16 seriously injured.<ref></ref><ref></ref>		Hexamethylenediamine is moderately toxic, with {{LD50}} of 792–1127&nbsp;mg/kg.<ref name=Ullmann/><ref>{{Cite web|url=https://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=H11696&brand=ALDRICH&PageToGoToURL=https://www.sigmaaldrich.com/catalog/product/aldrich/h11696?lang=en|title=MSDS - H11696|website=www.sigmaaldrich.com|access-date=2019-02-19}}</ref><ref>{{Cite journal |last=Kennedy |first=Gerald L. |date=2005 |title=Toxicity of hexamethylenediamine |url=https://pubmed.ncbi.nlm.nih.gov/15720033/ |journal=Drug and Chemical Toxicology |volume=28 |issue=1 |pages=15–33 |doi=10.1081/dct-39681 |issn=0148-0545 |pmid=15720033|s2cid=84650430 }}</ref> Nonetheless, like other basic amines, it can cause serious burns and severe irritation. Such injuries were observed in the accident at the ] site in ], near ] (UK) on 4 January 2007 in which 37 persons were injured, one of them seriously.<ref></ref><ref></ref>
	==Stability==		== See also ==
			* ]
	Hexamethylenediamine is stable in air but combustible. Like all organic compounds, it is incompatible with strong ]s.
			* ]
	== References ==		==References==
	{{Reflist}}		{{Reflist}}
	]		]
	]		]
	]
	]
	]
	]
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	]
	]