Acido emimellitico

Acido emimellitico
Formula di struttura dell'acido emimellitico
Formula di struttura dell'acido emimellitico
Nome IUPAC
acido 1,2,3-benzentricarbossilico
Caratteristiche generali
Formula bruta o molecolareC9H6O6
Massa molecolare (u)210,140
Aspettosolido biancastro[1]
Numero CAS569-51-7
Numero EINECS209-317-0
PubChem11288
SMILES
C1=CC(=C(C(=C1)C(=O)O)C(=O)O)C(=O)O
Proprietà chimico-fisiche
Solubilità in acquamolto solubile[2]
Temperatura di fusione197 °C (470 K)[2]
Proprietà termochimiche
ΔfH0 (kJ·mol−1)-1160[2]
Indicazioni di sicurezza
Simboli di rischio chimico
irritante
attenzione
Frasi H315 - 319 - 335 [1]
Consigli P261 - 305+351+338 [1]
Modifica dati su Wikidata · Manuale

L'acido emimellitico o acido 1,2,3-benzentricarbossilico è un composto organico con formula C9H6O6. È uno dei tre possibili isomeri derivati del benzene con tre gruppi carbossilici; gli altri due isomeri sono l'acido trimesico (acido 1,3,5-benzentricarbossilico) e l'acido trimellitico (acido 1,2,4-benzentricarbossilico). Il composto è presente in natura in ligniti e carboni bituminosi, assieme a numerosi altri acidi organici aromatici.[3] L'acido emimellitico non è di interesse industriale e non ha applicazioni pratiche.[2][4] È disponibile in commercio per usi di laboratorio in forma idrata, C9H6O6⋅xH2O, che si presenta come solido biancastro.[1]

Struttura

La molecola dell'acido emimellitico non è planare: i gruppi carbossilici in 1 e 3 giacciono nel piano dell'anello benzenico, mentre il carbossile in 2 è perpendicolare a questo piano.[5] Allo stato solido si conosce la struttura del composto diidrato, che cristallizza in forma triclina, gruppo spaziale P1, con costanti di reticolo a = 872,8 pm, b = 911,8 pm, c = 708,6 pm, β = 88,1°, γ = 106,46, con 2 unità di formula per cella elementare.[6]

Sintesi

L'acido emimellitico fu descritto per la prima volta nel 1869 da Adolf von Baeyer, che lo ottenne a partire dall'acido mellitico.[7] L'acido trimellitico si può ottenere per ossidazione di emimellitene (1,2,3-trimetilbenzene) o di 2,3,4-trimetilfenolo.[2]

Tossicità / Indicazioni di sicurezza

L'acido emimellitico è disponibile in commercio in forma idrata. È considerato irritante per la pelle, per gli occhi e per il sistema respiratorio. Non risultano rischi di cancerogenicità.[1]

Note

  1. ^ a b c d e Merck 2018
  2. ^ a b c d e Park e Sheehan 1998
  3. ^ Hayatsu et al. 1978
  4. ^ Rohrscheid 2002
  5. ^ Marković et al. 2004
  6. ^ Mo e Adman 1975
  7. ^ Baeyer 1869

Bibliografia

Altri progetti

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