1-propantiolo

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1-propantiolo
Nome IUPAC
1-propantiolo
Abbreviazioni
1-PrSH
Nomi alternativi
propantiolo
n-propantiolo
1-propilmercaptano
Caratteristiche generali
Formula bruta o molecolareC3H8S
Massa molecolare (u)76,16
Aspettoliquido incolore
Numero CAS107-03-9
Numero EINECS203-455-5
PubChem7848
SMILES
CCCS
Proprietà chimico-fisiche
Densità (g/cm3, in c.s.)0,843 a 20 °C
Indice di rifrazione1,4380 a 20 °C
Solubilità in acqua1,90 g/L a 25 °C
Coefficiente di ripartizione 1-ottanolo/acqua1,81
Temperatura di fusione−113,3 °C
ΔfusH0 (kJ·mol−1)5,48
ΔfusS0 (J·K−1mol−1)34,23
Temperatura di ebollizione67,8 °C
ΔebH0 (kJ·mol−1)32,05
Punto triplo−113,17 °C
Punto critico257 °C
45,3 atm
Tensione di vapore (Pa) a 293,15 K1,63×104
Proprietà termochimiche
ΔcombH0 (kJ·mol−1)−372×105 J/kg
Proprietà tossicologiche
DL50 (mg/kg)1790 mg/kg , ratto, o.s.
Indicazioni di sicurezza
Punto di fiamma−20 °C (vaso chiuso)
Simboli di rischio chimico
infiammabile corrosivo irritante
Frasi H225 - 302 - 315 - 318 - 335
Consigli P210 - 261 - 280 - 305+351+338 [1]
Modifica dati su Wikidata · Manuale

L'1-propantiolo, o 1-propilmercaptano è un composto organico di formula CH3CH2CH2SH appartenente alla categoria dei tioli. In condizioni standard appare come un liquido incolore facilmente infiammabile, dal forte odore caratterisstico che può ricordare quello del cavolo, poco solubile in acqua ma ben miscibile in etanolo, dietiletere, acetone, glicole propilenico e benzene. Trova impiego come erbicida e fungicida e come reagente nelle sintesi industriali[2].

È un liquido incolore con un odore forte e sgradevole. È moderatamente tossico ed è meno denso dell'acqua e leggermente solubile in acqua. È usato come materia prima per insetticidi. È altamente infiammabile ed emette fumi (o gas) irritanti o tossici in caso di incendio. Il riscaldamento provocherà un aumento della pressione con rischio di scoppio.

Sintesi

Il propantiolo può essere sintetizzato in diversi modi, tendenzialmente per reazione del n-propanolo o di un suo derivato con un composto inorganico contenente zolfo. Di seguito i metodi più comuni:[2]

Può anche essere preparato mediante reazione di idrosolfuro di sodio con 1-cloropropano.

Reattività

L'1-propantiolo ha carattere debolmente acido e può quindi dare reazioni acido-base:

L'1-propantiolo può dare inoltre reazioni di ossidazione con la formazione di un legame disolfuro tra due molecole di propantiolo:[3]

Applicazioni

L'1-propantiolo viene utilizzato come erbicida, fungicida e come reagente di sintesi. Trova altresì impiego come agente aromatizzante sintetico, perlopiù in miscela con gas tossici per facilitarne l'identificazione tramite olfatto.[2]

Note

  1. ^ 1-Propantiolo - scheda di dati di sicurezza (PDF), su sigma-aldrich.com, Sigma-Aldrich. URL consultato il 17 luglio 2018.
  2. ^ a b c (EN) Propyl mercaptan, su Hazardous Substances Data Bank, National Institutes of Health. URL consultato il 16 luglio 2018.
  3. ^ (EN) Propyl mercaptan, su NIST Chemistry WebBook, NIST. URL consultato il 17 luglio 2018.

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