Acido ammidosolfonico

Acido ammidosolfonico
Nomi alternativi
acido amminosolfonico
acido ammidosolforico
acido solfammico
acido solfammidico
Caratteristiche generali
Formula bruta o molecolareH2NSO3H
Massa molecolare (u)97,09 g/mol
Aspettosolido bianco
Numero CAS5329-14-6
Numero EINECS226-218-8
PubChem5987, 19366655 e 134939864
SMILES
NS(=O)(=O)O
Proprietà chimico-fisiche
Densità (g/cm3, in c.s.)2,13 (25 °C)
Costante di dissociazione acida a 25 °C K1,01 x 10-1
Solubilità in acqua213 g/L (20 °C)
Temperatura di fusione205 °C (478 K) (decomposizione)
Indicazioni di sicurezza
Simboli di rischio chimico
irritante
attenzione
Frasi H319 - 315 - 412
Consigli P273 - 305+351+338 - 302+352 [1]
Modifica dati su Wikidata · Manuale

L'acido ammidosolfonico o acido solfammico è un acido monoprotico con formula H2NSO3H che rappresenta formalmente la monoammide dell'acido solforico. Una volta deprotonato forma l'anione solfammato H2NSO3-.

A temperatura ambiente si presenta come un solido bianco inodore. È un composto irritante, pericoloso per l'ambiente.

Allo stato solido il composto esiste in forma stabile zwitterionica, in soluzione acquosa subisce lentamente idrolisi formando bisolfato d'ammonio (NH4)HSO4.

Sintesi

A livello industriale, l'acido ammidosolfonico viene prodotto facendo reagire l'urea con l'oleum (miscela di triossido di zolfo e acido solforico).[2] La sintesi avviene nei seguenti due stadi:

OC(NH2)2 + SO3 → OC(NH2)(NHSO3H)
OC(NH2)(NHSO3H) + H2SO4 → CO2 + 2 H2NSO3H

Usi

L'acido ammidosolfonico viene impiegato come standard primario (previo riscaldamento in stufa) per standardizzare soluzioni di composti basici quali l'idrossido di sodio da utilizzare poi in titolazioni acidimetriche.

Questo composto è anche il precursore dei dolcificanti ciclamato e acesulfame K; inoltre è pure un importante precursore di una serie di farmaci tra cui una classe di antibiotici, antivirali usati nella terapia dell'HIV, antineoplastici, antiepilettici e farmaci utilizzati per il dimagrimento.[3]

Tra gli altri suoi utilizzi figurano quelli come agente pulente per metalli e ceramiche, come catalizzatore per l'esterificazione, ed è usato anche per la produzione di vernici e pigmenti, erbicidi, resine urea-formaldeide, e di solfammato d'ammonio impiegato come ritardante di fiamma. Facendo reagire l'acido ammidosolfonico con acido nitrico è possibile sintetizzare il protossido d'azoto (N2O).

Note

  1. ^ scheda dell'acido amminosolfonico su IFA-GESTIS (archiviato dall'url originale il 16 ottobre 2019).
  2. ^ A. Metzger, Sulfamic Acid in Ullmann's Encyclopedia of Industrial Chemistry, 2012, Wily-VCH, Weinheim. DOI: 10.1002/14356007.a25_439
  3. ^ J.Y. Winum, A. Scozzafava; J.L. Montero; C.T. Supuran, Sulfamates and their therapeutic potential, in Medicinal Research Reviews, vol. 25, n. 2, pp. 186–228, DOI:10.1002/med.20021, PMID 15478125.

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Controllo di autoritàThesaurus BNCF 18054
  Portale Chimica: il portale della scienza della composizione, delle proprietà e delle trasformazioni della materia

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