Hexaméthylènediamine

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Hexaméthylènediamine
Image illustrative de l’article Hexaméthylènediamine
Image illustrative de l’article Hexaméthylènediamine
Identification
Nom UICPA Hexane-1,6-diamine
Synonymes

1,6-diaminohexane, 1,6-hexanediamine

No CAS 124-09-4
No ECHA 100.004.255
PubChem 16402
SMILES
Apparence solide blanc
Propriétés chimiques
Formule C6H16N2  [Isomères]
Masse molaire[1] 116,204 6 ± 0,006 3 g/mol
C 62,02 %, H 13,88 %, N 24,11 %,
Propriétés physiques
T° fusion 42 à 45 °C[2]
T° ébullition 204 à 205 °C[2]
Solubilité 490 g l−1 à 20 °C (eau)[2]
Masse volumique 0,89 g cm−3 à 25 °C[2]
T° d'auto-inflammation 305 °C[réf. souhaitée]
Point d’éclair 94 °C[2]
Limites d’explosivité dans l’air 0,7 - 6,3 %[réf. souhaitée]
Pression de vapeur saturante 25 Pa à 20 °C[3]
Thermochimie
ΔfH0solide −205 kJ mol−1[réf. souhaitée]
Propriétés optiques
Indice de réfraction  1,439[2]
Précautions
SGH
SGH05 : CorrosifSGH07 : Toxique, irritant, sensibilisant, narcotique
H302, H312, H314, H335, P261, P280, P310 et P305+P351+P338
NFPA 704

Symbole NFPA 704.

 
Directive 67/548/EEC
Écotoxicologie
DL50 750 mg kg−1 (rats, oral)[4]
LogP 0,386[réf. souhaitée]
Composés apparentés
Autres composés

Cadavérine (pentyl-1,5-diamine)

Unités du SI et CNTP, sauf indication contraire.
modifier 

L’hexaméthylènediamine (HMD) est un composé organique de formule semi-développée H2N(CH2)6NH2.

Ce solide blanc hygroscopique a une forte odeur d’amine, semblable à celle de la pipéridine.

Synthèse

Cette diamine aliphatique est préparée par hydrogénation de l’adiponitrile de formule NC(CH2)4CN :

NC(CH2)4CN + 4 H2 → H2N(CH2)6NH2

Les premières synthèses industrielles étaient réalisées en présence d'ammoniac et avec l'aide d'un catalyseur. On utilisait en général du cobalt, du fer ou du nickel de Raney. La formation de produits secondaires tels que le 1,2-diaminocyclohexane ou l'hexaméthylèneimine était observée.

Rhône-Poulenc a développé un procédé utilisant comme catalyseur du nickel en suspension dans de la soude. La réaction est réalisée à 75 °C et 20 bar et une sélectivité satisfaisante est observée[5].

Environ un million de tonnes sont produites annuellement.

Utilisations

Sa bifonctionnalité lui permet de servir de monomère pour la synthèse de polymères. Elle est surtout utilisée pour fabriquer plusieurs polyamides, en particulier le Nylon 6-6 via la polycondensation avec l’acide adipique[6].

Comme toutes les diamines primaires, elle est bivalente dans les polyamidifications et tétravalente quand elle intervient comme agent de réticulation avec les résines diépoxyde.

Toxicité

L’hexaméthylènediamine est modérément toxique.

Stabilité

Comme tous les composés organiques, elle est incompatible avec les oxydants forts.

Notes et références

  1. ↑ Masse molaire calculée d’après « Atomic weights of the elements 2007 », sur www.chem.qmul.ac.uk.
  2. ↑ a b c d e et f 1,6-hexanediamine, sur chemicalbook.com.
  3. ↑ Entrée du numéro CAS « 124-09-4 » dans la base de données de produits chimiques GESTIS de la IFA (organisme allemand responsable de la sécurité et de la santé au travail) (allemand, anglais) (JavaScript nécessaire).
  4. ↑ Roempp Online - Version 3.5, 2009, Georg Thieme Verlag, Stuttgart.
  5. ↑ Gilles Lefebvre et Alain Chauvel, « Hexaméthylènediamine », Techniques de l'ingénieur,‎ (lire en ligne).
  6. ↑ Georges Mollard, « Polyamide 6-6 », Techniques de l'ingénieur,‎ (lire en ligne Accès limité).

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