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Properties of substance:

aniline



skc-file

Group of substances:

organic

Physical appearance:

colorless oily liquid

Empirical formula (Hill's system for organic substances):

C6H7N

Structural formula as text:

C6H5NH2

Molar/atomic mass: 93.1265

Melting point (°C):

-5.89

Boiling point (°C):

184.4

Solubility (g/100 g of solvent):

1,1,2-trichloro-1,2,2-trifluoroethane: insoluble [Ref.]
acetone: miscible [Ref.]
ammonia liquid : miscible [Ref.]
benzene: miscible [Ref.]
carbon tetrachloride: miscible [Ref.]
cyclohexane: 66.7 (30.8°C) [Ref.]
diethyl ether: miscible [Ref.]
ethanol: miscible [Ref.]
hexane: 69.5 (69.2°C) [Ref.]
hydrogen fluoride : very soluble [Ref.]
ligroin: soluble [Ref.]
sulfolane: miscible [Ref.]
water: 3.4 (20°C) [Ref.]
water: 4.031 (50°C) [Ref.]
water: 4.671 (60°C) [Ref.]
water: 6.4 (90°C) [Ref.]

Multicomponent solubility (in wt%):

(layer 1): water 96.9%, aniline 3.1%, (layer 2): water 5.%, aniline 95.%, 20 °C [Ref.]
(layer 1): water 96.7%, aniline 3.3%, (layer 2): water 5.3%, aniline 94.7%, 40 °C [Ref.]
(layer 1): water 96.2%, aniline 3.8%, (layer 2): water 5.8%, aniline 94.2%, 60 °C [Ref.]
(layer 1): water 94.5%, aniline 5.5%, (layer 2): water 6.5%, aniline 93.5%, 80 °C [Ref.]
(layer 1): water 92.8%, aniline 7.2%, (layer 2): water 8.4%, aniline 91.6%, 100 °C [Ref.]

Numerical data:

Year of discovery: 1826

Density:

1.03 (-183°C, g/cm3)
1.02173 (20°C, g/cm3)

Synthesis 1:

Reference: Гитис С.С., Глаз А.И., Иванов А.В. Практикум по органической химии: Органический синтез. - М.: Высшая школа, 1991 pp. 205-206



In a round-bottom flask with air reflux condenser 10 ml of nitrobenzene is mixed with 19 gr of iron filings. Then in small portions 56 ml of concentrated hydrochloric is added, the contents of the flasks is shaked all the time. If the reaction is too violent, the reaction mixture is cooled on a water bath. After the addition of all hydrochloric acid the flask is heated on a boiling water bath for 0,5 h with regular shaking. The reduction reaction is considered completed when there is no odor of nitrobenzene (odor of bitter almond). The hot mixture is neutralised with caution by 40% solution of sodium hydroxide until the alkaline reaction and aniline is distilled from this flask with water steam. The distillation is continued until the distillate doesn't become absolutely clear.

From the obtained mixture aniline is separated by saturation of the mixture by sodium chloride (20 gr of salt per 100 ml of the mixture is added). Aniline is separated in a separation funnel, aniline remaining in the solution is extracted with ether. The ether extraction is added to aniline and dried by pieces of solid sodium hydroxide. After this the ether is distilled, a small amount of zinc powder is added to the flask and aniline is distilled with air condenser, the fraction with boiling point at 182-184 C is collected.

The yield is 9 gr (99% from theory).

Reactions of synthesis:

  1. Yeild 77%. [Ref.1]
    C6H5N3 + 2CH3OH + 2Na → C6H5NH2 + N2 + 2CH3ONa

Reactions:

  1. Yeild 50-62%. [Ref.1aster]
    C6H5NH2 + NaNO2 + 2HCl → C6H5N2Cl + NaCl + 2H2O
    C6H5N2Cl + NaH2AsO3 → C6H5As(O)(OH)2 + NaCl + N2
  2. Yeild 75-84%. [Ref.1]
    C6H5NH2 + I2 + NaHCO3 → IC6H4NH2 + NaI + CO2 + H2O
  3. Yeild 81%. [Ref.1]
    C6H5Cl + C6H5NH2 → C6H5NHC6H5 + HCl
  4. Yeild 78%. [Ref.1]
    2C6H5Cl + C6H5NH2 → (C6H5)3N + 2HCl
  5. Yeild 71%. [Ref.1aster]
    C6H5NH2 + (CH3)3CONO + CH2=CHCN + CuCl2 → C6H5CH2CHClCN + N2 + Cu(OH)Cl + (CH3)3COH
  6. [Ref.1]
    2C6H5NH2 + 2K → 2C6H5NHK + H2

Refractive index (nD):

1.5863 (20°C)

Vapour pressure (Torr):

10 (68.3°C)
33 (92°C)
50 (102°C)

Dissociation:

pKBH+ (1) = 4.58 (25°C, water)
pKBH+ (1) = 4.1 (20°C, formamide)
pKa (1) = 27 (25°C, water)
pKa (1) = 30.7 (20°C, dimethylsulfoxide)

Permittivity (dielectric constant):

6.89 (20°C)
5.93 (70°C)

Dipole moment (D):

1.53 (20°C)

Viscosity (mPa·s):

3.77 (25°C)
0.825 (100°C)

Surface tension (mN/m):

43.3 (20°C)

Speed sound (m/s):

1659 (20°C, aggregative state - liquid)

Standard molar enthalpy (heat) of formation ΔfH0 (298.15 K, kJ/mol):

29.7 (l)

Standard molar entropy S0 (298.15 K, J/(mol·K)):

192 (l)

Molar heat capacity at constant pressure Cp (298.15 K, J/(mol·K)):

191 (l)

Molar enthalpy (heat) of fusion ΔfusH (kJ/mol):

10.56

Enthalpy (heat) of vaporization ΔvapH (kJ/mol):

55.83

Flash point (°C):

79

Autoignition temperature (°C):

562

Heat of combustion (kJ/mol):

3410

LD50 (mg/kg):

250 (cats, oral)
460 (mice, oral)

Critical temperature (°C):

425.65

Critical pressure (MPa):

5.134

Critical density (g/cm3):

0.314

References:

  1. CRC Handbook of Chemistry and Physics. - 90ed. - CRC Press, 2010. - pp. 3-26
  2. Lewis R.J. Sax's Dangerous Properties of Industrial Materials. - 11ed. - Wiley-interscience, 2004. - pp. 260-261
  3. Seidell A. Solubilities of organic compounds. - 3ed., vol.2. - New York: D. Van Nostrand Company, 1941. - pp. 406-419
  4. Yalkowsky S.H., Yan H. Handbook of aqueous solubility data. - CRC Press, 2003. - pp. 262
  5. Вредные вещества в промышленности: Справочник для химиков, инженеров и врачей. - 7-е изд., Т.2. - Л.: Химия, 1976. - pp. 281-283 [Russian]
  6. Корольченко А.Я., Корольченко Д.А. Пожаровзрывоопасность веществ и материалов и средства их тушения. - 2 изд, Ч.1. - М.: Ассоциация Пожнаука, 2004. - pp. 182 [Russian]
  7. Некрасов Б.В. Основы общей химии. - Т.1. - М.: Химия, 1973. - pp. 555-556 [Russian]
  8. Рабинович В.А., Хавин З.Я. Краткий химический справочник. - Л.: Химия, 1977. - pp. 124 [Russian]
  9. Справочник по растворимости. - Т.1, Кн.1. - М.-Л.: ИАН СССР, 1961. - pp. 442-443 [Russian]
  10. Справочник по растворимости. - Т.1, Кн.2. - М.-Л.: ИАН СССР, 1962. - pp. 1459-1463 [Russian]
  11. Справочник химика. - Т. 3. - М.-Л.: Химия, 1965. - pp. 85 [Russian]
  12. Химическая энциклопедия. - Т. 1. - М.: Советская энциклопедия, 1988. - pp. 165 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru