Decalina

Decalina
formula di struttura
formula di struttura
Nome IUPAC
biciclo[4.4.0]decano
Caratteristiche generali
Formula bruta o molecolareC10H18
Massa molecolare (u)138.25 g mol−1
Aspettoliquido incolore
Numero CAS91-17-8
Numero EINECS202-046-9
PubChem7044
SMILES
C1CCC2CCCCC2C1
Proprietà chimico-fisiche
Solubilità in acqua0,00089 g/L
Temperatura di fusioneracemo: −40 °C (233,15 K)
trans: −31 (242,15 K) °C
cis: −43 °C (230,15 K)
Temperatura di ebollizionetrans: 187 °C (460,15 K)
cis: 196 °C(469,15 K)
Tensione di vapore (Pa) a 293,15 K106,4
Proprietà tossicologiche
DL50 (mg/kg)4.170 mg/kg
Indicazioni di sicurezza
Punto di fiamma−57 °C (330,15 K)
Limiti di esplosione0,7 - 4,9 % vol.
Temperatura di autoignizione255 °C (528,15 K)
Simboli di rischio chimico
infiammabile tossicità acuta tossico a lungo termine corrosivo pericoloso per l'ambiente
Frasi H226 - 304 - 314 - 331 - 410
Consigli P210 - 280 - 301+330+331 - 303+361+353 - 304+340+310 - 305+351+338 [1]
Modifica dati su Wikidata · Manuale

La decalina (decaidronaftalene, conosciuta anche come biciclo[4.4.0]decano) è un composto organico. A temperatura ambiente si presenta come un liquido incolore dall'odore aromatico. È l'analogo idrogenato del naftalene, dal quale si ottiene per idrogenazione catalitica. Viene usata come solvente industriale per resine e carburanti.

Isomeri

La decalina può essere trovata in forma cis o in forma trans. La forma trans è energeticamente più stabile a causa delle minori interazioni di carattere sterico. La reazione di isomerizzazione cis-trans può essere considerata irreversibile a causa della grande differenza in ordine di grandezza delle due costanti cinetiche dell'equilibrio[2]. La cis-decalina è una molecola chirale pur non possedendo atomi di carbonio asimmetrici, ma possiede un asse di simmetria passante per il punto di mezzo del legame covalente 9-10 e ortogonale a esso. Ad ogni modo tale chiralità è rimossa dalla presenza di un processo di inversione della sedia che forma l'immagine speculare della molecola stessa.

[3]

Note

  1. ^ Decaidronaftalene, miscela di cis + trans, scheda di dati di sicurezza, su sigmaaldrich.com. URL consultato il 10-12-2024.
  2. ^ http://amsdottorato.cib.unibo.it/1353/1/Gambatesa_Antonio_tesi.pdf
  3. ^ ISFuel.com Animation, su isfuel.com.

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