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Hexamethylenediamine

August 31, 2023

Hexamethylenediamine is the organic compound with the formula H2N(CH2)6NH2. The molecule is a diamine, consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups. The colorless solid (yellowish for some commercial samples) has a strong amine odor. About 1 billion kilograms are produced annually.[4]

Hexamethylenediamine[1][2]
Names
Preferred IUPAC name
Hexane-1,6-diamine[3]
Other names
  • 1,6-Diaminohexane
  • 1,6-Hexanediamine
Identifiers
  • 124-09-4 Y
3D model (JSmol)
  • Interactive image
1098307
ChEBI
  • CHEBI:39618 N
ChEMBL
  • ChEMBL303004 N
ChemSpider
  • 13835579 N
DrugBank
  • DB03260 N
ECHA InfoCard 100.004.255
EC Number
  • 204-679-6
2578
MeSH 1,6-diaminohexane
  • 16402
RTECS number
  • MO1180000
UNII
  • ZRA5J5B2QW Y
UN number 2280
  • DTXSID5024922
  • InChI=1S/C6H16N2/c7-5-3-1-2-4-6-8/h1-8H2 N
    Key: NAQMVNRVTILPCV-UHFFFAOYSA-N N
  • NCCCCCCN
Properties
C6H16N2
Molar mass 116.208 g·mol−1
Appearance Colourless crystals
Density 0.84 g/mL
Melting point 39 to 42 °C (102 to 108 °F; 312 to 315 K)
Boiling point 204.6 °C; 400.2 °F; 477.7 K
490 g L−1
log P 0.386
Thermochemistry
−205 kJ mol−1
Hazards
GHS labelling:
Danger
H302, H312, H314, H335
P261, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
Flash point 80 °C (176 °F; 353 K)
Explosive limits 0.7–6.3%
Lethal dose or concentration (LD, LC):
  • 750 mg kg−1 (oral, rat)
  • 1.11 g kg−1 (dermal, rabbit)
Related compounds
Related alkanamines
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Synthesis Edit

Hexamethylenediamine was first reported by Theodor Curtius.[5] It is produced by the hydrogenation of adiponitrile:

NC(CH2)4CN + 4 H2 → H2N(CH2)6NH2

The hydrogenation is conducted on molten adiponitrile diluted with ammonia,[6] typical catalysts being based on cobalt and iron. The yield is good, but commercially significant side products are generated by virtue of reactivity of partially hydrogenated intermediates. These other products include 1,2-diaminocyclohexane, hexamethyleneimine, and the triamine bis(hexamethylenetriamine).

An alternative process uses Raney nickel 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.[4]

Applications Edit

Hexamethylenediamine is used almost exclusively for the production of polymers, an application that takes advantage of its structure.[7][8] 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 nylon 66 via condensation with adipic acid. Otherwise hexamethylene diisocyanate (HDI) is generated from this diamine by phosgenation as a monomer feedstock in the production of polyurethane.[9][10] The diamine also serves as a cross-linking agent in epoxy resins.[11][12][13]

Safety Edit

Hexamethylenediamine is moderately toxic, with LD50 of 792–1127 mg/kg.[4][14][15] Nonetheless, like other basic amines, it can cause serious burns and severe irritation. Such injuries were observed in the accident at the BASF site in Seal Sands, near Billingham (UK) on 4 January 2007 in which 37 persons were injured, one of them seriously.[16][17]

See also Edit

References Edit

  1. ^ Merck Index, 11th Edition, 4614.
  2. ^ MSDS
  3. ^ "1,6-diaminohexane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 29 May 2012.
  4. ^ a b c Robert A. Smiley "Hexamethylenediamine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a12_629
  5. ^ Curtius, Theodor and Clemm, Hans (1900) "Synthese des 1,3-Diaminopropans und 1,6-Diaminohexans aus Glutarsäure resp. Korksäure" (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.
  6. ^ "SRIC Report - Report 31C - Advances in Adiponitrile (ADN) and Hexamethylenediamine (HMDA) Processes | IHS Markit". ihsmarkit.com. Retrieved 2019-02-19.
  7. ^ Longseng, Rutchanon; Khaokong, Chuanpit (2020-12-01). "Hexamethylene diamine-modified epoxidized natural rubber and its effect on cure characteristics and properties of natural rubber blends". Iranian Polymer Journal. 29 (12): 1113–1121. doi:10.1007/s13726-020-00865-x. ISSN 1735-5265. S2CID 221824894.
  8. ^ Hu, Juncheng; Feng, Xia; Liu, Zhengyi; Zhao, Yiping; Chen, Li (July 2017). "Surface amine-functionalization of UHMWPE fiber by bio-inspired polydopamine and grafted hexamethylene diamine: Surface amine-functionalization of UHMWPE fiber by PDA and HMDA". Surface and Interface Analysis. 49 (7): 640–646. doi:10.1002/sia.6203. S2CID 99804759.
  9. ^ Kim, C. K.; Kim, B. K.; Jeong, H. M. (1991-09-01). "Aqueous dispersion of polyurethane ionomers from hexamethylene diisocyanate and trimellitic anhydride". Colloid and Polymer Science. 269 (9): 895–900. doi:10.1007/BF00657306. ISSN 1435-1536. S2CID 94481368.
  10. ^ Hu, Jin; Chen, Zhuo; He, Yong; Huang, Hong; Zhang, Xinya (2017-05-01). "Synthesis and structure investigation of hexamethylene diisocyanate (HDI)-based polyisocyanates". Research on Chemical Intermediates. 43 (5): 2799–2816. doi:10.1007/s11164-016-2795-1. ISSN 1568-5675. S2CID 100565578.
  11. ^ Luňák, S.; Dušek, K. (2007-03-08). "Curing of epoxy resins. II. Curing of bisphenol a diglycidyl ether with diamines". Journal of Polymer Science: Polymer Symposia. 53 (1): 45–55. doi:10.1002/polc.5070530108.
  12. ^ Dušek, K.; Pleštil, J.; Lednický, F.; Luňák, S. (1978-04-01). "Are cured epoxy resins inhomogeneous?". Polymer. 19 (4): 393–397. doi:10.1016/0032-3861(78)90243-4. ISSN 0032-3861.
  13. ^ Lainioti, Georgia Ch.; Savva, Panagiota; Druvari, Denisa; Avramidis, Pavlos; Panagiotaras, Dionisios; Karellou, Eva Iris Eleftheria; Kallitsis, Joannis K. (2021-08-01). "Cross-linking of antimicrobial polymers with hexamethylene diamine to prevent biofouling in marine applications". Progress in Organic Coatings. 157: 106336. doi:10.1016/j.porgcoat.2021.106336. ISSN 0300-9440. S2CID 236243177.
  14. ^ "MSDS - H11696". www.sigmaaldrich.com. Retrieved 2019-02-19.
  15. ^ Kennedy, Gerald L. (2005). "Toxicity of hexamethylenediamine". Drug and Chemical Toxicology. 28 (1): 15–33. doi:10.1081/dct-39681. ISSN 0148-0545. PMID 15720033. S2CID 84650430.
  16. ^ BBC News
  17. ^ BBC News

August 31, 2023
hexamethylenediamine, organic, compound, with, formula, 6nh2, molecule, diamine, consisting, hexamethylene, hydrocarbon, chain, terminated, with, amine, functional, groups, colorless, solid, yellowish, some, commercial, samples, strong, amine, odor, about, bil. Hexamethylenediamine is the organic compound with the formula H2N CH2 6NH2 The molecule is a diamine consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups The colorless solid yellowish for some commercial samples has a strong amine odor About 1 billion kilograms are produced annually 4 Hexamethylenediamine 1 2 NamesPreferred IUPAC name Hexane 1 6 diamine 3 Other names 1 6 Diaminohexane1 6 HexanediamineIdentifiersCAS Number 124 09 4 Y3D model JSmol Interactive imageBeilstein Reference 1098307ChEBI CHEBI 39618 NChEMBL ChEMBL303004 NChemSpider 13835579 NDrugBank DB03260 NECHA InfoCard 100 004 255EC Number 204 679 6Gmelin Reference 2578MeSH 1 6 diaminohexanePubChem CID 16402RTECS number MO1180000UNII ZRA5J5B2QW YUN number 2280CompTox Dashboard EPA DTXSID5024922InChI InChI 1S C6H16N2 c7 5 3 1 2 4 6 8 h1 8H2 NKey NAQMVNRVTILPCV UHFFFAOYSA N NSMILES NCCCCCCNPropertiesChemical formula C 6H 16N 2Molar mass 116 208 g mol 1Appearance Colourless crystalsDensity 0 84 g mLMelting point 39 to 42 C 102 to 108 F 312 to 315 K Boiling point 204 6 C 400 2 F 477 7 KSolubility in water 490 g L 1log P 0 386ThermochemistryStd enthalpy offormation DfH 298 205 kJ mol 1HazardsGHS labelling PictogramsSignal word DangerHazard statements H302 H312 H314 H335Precautionary statements P261 P280 P305 P351 P338 P310NFPA 704 fire diamond 320Flash point 80 C 176 F 353 K Explosive limits 0 7 6 3 Lethal dose or concentration LD LC LD50 median dose 750 mg kg 1 oral rat 1 11 g kg 1 dermal rabbit Related compoundsRelated alkanamines PentylamineCadaverineMethylhexanamineTuaminoheptaneExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Synthesis 2 Applications 3 Safety 4 See also 5 ReferencesSynthesis EditHexamethylenediamine was first reported by Theodor Curtius 5 It is produced by the hydrogenation of adiponitrile NC CH2 4CN 4 H2 H2N CH2 6NH2The hydrogenation is conducted on molten adiponitrile diluted with ammonia 6 typical catalysts being based on cobalt and iron The yield is good but commercially significant side products are generated by virtue of reactivity of partially hydrogenated intermediates These other products include 1 2 diaminocyclohexane hexamethyleneimine and the triamine bis hexamethylenetriamine An alternative process uses Raney nickel 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 4 Applications EditHexamethylenediamine is used almost exclusively for the production of polymers an application that takes advantage of its structure 7 8 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 nylon 66 via condensation with adipic acid Otherwise hexamethylene diisocyanate HDI is generated from this diamine by phosgenation as a monomer feedstock in the production of polyurethane 9 10 The diamine also serves as a cross linking agent in epoxy resins 11 12 13 Safety EditHexamethylenediamine is moderately toxic with LD50 of 792 1127 mg kg 4 14 15 Nonetheless like other basic amines it can cause serious burns and severe irritation Such injuries were observed in the accident at the BASF site in Seal Sands near Billingham UK on 4 January 2007 in which 37 persons were injured one of them seriously 16 17 See also Edit1 2 Diaminocyclohexane 2 MethylpentamethylenediamineReferences Edit Merck Index 11th Edition 4614 MSDS 1 6 diaminohexane Compound Summary PubChem Compound USA National Center for Biotechnology Information 26 March 2005 Identification and Related Records Retrieved 29 May 2012 a b c Robert A Smiley Hexamethylenediamine in Ullmann s Encyclopedia of Industrial Chemistry Wiley VCH Weinheim 2005 doi 10 1002 14356007 a12 629 Curtius Theodor and Clemm Hans 1900 Synthese des 1 3 Diaminopropans und 1 6 Diaminohexans aus Glutarsaure resp Korksaure Synthesis of 1 3 diaminopropane and 1 6 diaminohexane from glutaric acid and suberic acid respectively Journal fur praktische Chemie 2nd series 62 189 211 SRIC Report Report 31C Advances in Adiponitrile ADN and Hexamethylenediamine HMDA Processes IHS Markit ihsmarkit com Retrieved 2019 02 19 Longseng Rutchanon Khaokong Chuanpit 2020 12 01 Hexamethylene diamine modified epoxidized natural rubber and its effect on cure characteristics and properties of natural rubber blends Iranian Polymer Journal 29 12 1113 1121 doi 10 1007 s13726 020 00865 x ISSN 1735 5265 S2CID 221824894 Hu Juncheng Feng Xia Liu Zhengyi Zhao Yiping Chen Li July 2017 Surface amine functionalization of UHMWPE fiber by bio inspired polydopamine and grafted hexamethylene diamine Surface amine functionalization of UHMWPE fiber by PDA and HMDA Surface and Interface Analysis 49 7 640 646 doi 10 1002 sia 6203 S2CID 99804759 Kim C K Kim B K Jeong H M 1991 09 01 Aqueous dispersion of polyurethane ionomers from hexamethylene diisocyanate and trimellitic anhydride Colloid and Polymer Science 269 9 895 900 doi 10 1007 BF00657306 ISSN 1435 1536 S2CID 94481368 Hu Jin Chen Zhuo He Yong Huang Hong Zhang Xinya 2017 05 01 Synthesis and structure investigation of hexamethylene diisocyanate HDI based polyisocyanates Research on Chemical Intermediates 43 5 2799 2816 doi 10 1007 s11164 016 2795 1 ISSN 1568 5675 S2CID 100565578 Lunak S Dusek K 2007 03 08 Curing of epoxy resins II Curing of bisphenol a diglycidyl ether with diamines Journal of Polymer Science Polymer Symposia 53 1 45 55 doi 10 1002 polc 5070530108 Dusek K Plestil J Lednicky F Lunak S 1978 04 01 Are cured epoxy resins inhomogeneous Polymer 19 4 393 397 doi 10 1016 0032 3861 78 90243 4 ISSN 0032 3861 Lainioti Georgia Ch Savva Panagiota Druvari Denisa Avramidis Pavlos Panagiotaras Dionisios Karellou Eva Iris Eleftheria Kallitsis Joannis K 2021 08 01 Cross linking of antimicrobial polymers with hexamethylene diamine to prevent biofouling in marine applications Progress in Organic Coatings 157 106336 doi 10 1016 j porgcoat 2021 106336 ISSN 0300 9440 S2CID 236243177 MSDS H11696 www sigmaaldrich com Retrieved 2019 02 19 Kennedy Gerald L 2005 Toxicity of hexamethylenediamine Drug and Chemical Toxicology 28 1 15 33 doi 10 1081 dct 39681 ISSN 0148 0545 PMID 15720033 S2CID 84650430 BBC News BBC News Retrieved from https en wikipedia org w index php title Hexamethylenediamine amp oldid 1154507084, wikipedia, wiki, book, books, library,

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