Etyleenidiamiini

Etyleenidiamiini
Tunnisteet
IUPAC-nimi Etaani-1,2-diamiini
CAS-numero 107-15-3
PubChem CID 3301
SMILES C(CN)N [1]
Ominaisuudet
Molekyylikaava C2H8N2
Moolimassa 60,104 g/mol
Sulamispiste 11,1 °C [2]
Kiehumispiste 117 °C [2]
Tiheys 0,9 g/cm3[3]
Liukoisuus veteen Sekoittuu veteen [3]

Etyleenidiamiini (C2H8N2) on kaksi aminoryhmää sisältävä amiini. Etyleenidiamiinia käytetään muun muassa liuottimina sekä lääkkeiden, fungisidien ja synteettisten vahojen valmistuksessa.[4] Lisäksi yhdiste voi toimia kelaattina kompleksiyhdisteissä.

Ominaisuudet

Etyleenidiamiini, kuten useat muutkin amiinit, on keskivahvasti emäksinen aine. Huoneenlämmössä yhdiste on ulkomuodoltaan keltaista nestettä, joka haisee pistävältä. Etyleenidiamiini reagoi helposti klooria sisältävien orgaanisten aineiden sekä hapettimien ja happojen kanssa. [3]

Valmistus

Etyleenidiamiinia valmistetaan ammoniakin ja 1,2-dikloorietaanin välisellä reaktiolla. Reaktiossa syntyy myös etyleenidiamiinin polymeerejä kuten dietyleenitriamiinia, trietyleenitetramiinia ja tetraetyleenipentamiinia. Niiden syntymistä voidaan estää käyttämällä runsaasti ammoniakkia. [5]

Käyttö

Monet biologisesti aktiiviset aineet, kuten aminofylliini ja monet histamiinit sisältävät etyleenidiamiinirakenteen. Etyleenidiamiini on myös tärkeä yhdiste monien eri orgaanisten kemikaalien valmistuksessa kemikaalien valmistuksessa.

Synteesejä

EDTA on eli etyylidiamiinitetraetikkahappo on tärkeä kelatoiva yhdiste. EDTAa valmistetaan etyleenidiamiinin, formaldehydin ja natriumsyanidin alkoholiliuoksen välisellä reaktiolla. [5]

H2NCH2CH2NH2 + 4 CH2O + 4 NaCN + H2O → (NaOOCH2)2NCH2CH2N(CH2COONa)2 + NH3

Kaksi etyleenidiamiinihydrokloridimolekyyliä voivat polymeroitua muodostaen piperatsiinin hydrokloridia, josta voidaan valmistaa piperatsiinia.[5]

2 (H2NCH2CH2NH2·2HCl)→ C4H10N2·2HCl + 2 NH4Cl

Turvallisuus

Hengitettynä etyleenidiamiini aiheuttaa yskää ja hengityksen hankaloitumista. Pitkäaikainen altistuminen aineelle voi aiheuttaa astman puhkeamisen. Yhdiste voi aiheuttaa allergiaa iholle joutuessaan.[3] Pitkäaikainen altistus voi vaurioittaa maksaa ja munuaisia. Yhdisteen ei ole todettu aiheuttavan syöpää. [4]

Lähteet

  1. ↑ Ethylenediamine – Substance summary NCBI. Viitattu 16. elokuuta 2009.
  2. ↑ a b Physical properties: Ethylenediamine NLM Viitattu 16.8.2009
  3. ↑ a b c d Etyleenidiamiinin kansainvälinen kemikaalikortti Viitattu 16.8.2009
  4. ↑ a b T. S. S. Dikshith, Prakash V. Diwan: Industrial guide to chemical and drug safety, s. 219. Wiley-IEEE, 2003. ISBN 978-0-471-23698-6 Kirja Googlen teoshaussa (viitattu 16.8.2009). (englanniksi)
  5. ↑ a b c Harold Wittcoff, B. G. Reuben, Jeffrey S. Plotkin: Industrial organic chemicals, s. 147. Wiley-IEEE, 2004. ISBN 978-0-471-44385-8 Kirja Googlen teoshaussa (viitattu 16.8.2009). (englanniksi)

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