4-Pentenenitrile → Hydrogen Cyanide

HRID 1621063

Reaction equation

HRID 1621063 reaction equation
[C:1](#[N:6])C/C=C/C.[C:7](#[N:12])[CH2:8]/[CH:9]=[CH:10]\[CH3:11].[C:13](#[N:18])CCC=C>>[CH:1]#[N:6].[C:13](#[N:18])[CH2:11][CH2:10][CH2:9][CH2:8][C:7]#[N:12]

Participants

5

Reactant 3

HCID 116044-PentenenitrileHCID 5324707trans-3-PentenenitrileHCID 124683003-Pentenenitrile, (3Z)-

Product 2

HCID 768Hydrogen CyanideHCID 8128Adiponitrile

Procedure

The isomerization of cis-2-pentenenitrile (boiling point 127° C./1013 mbar) gives rise to the target products trans-3-pentenenitrile (boiling point 143° C./1013 mbar) and cis-3-pentenenitrile (boiling point 146° C./1013 mbar), and also small amounts of 4-pentenenitrile (boiling point 146° C./1013 mbar) and trans-2-pentenenitrile (boiling point 144° C./1013 mbar). Trans-3-pentenenitrile, cis-3-pentenenitrile and 4-pentenenitrile can be used, after distillative removal, for the hydrocyanation with hydrogen cyanide to give adiponitrile. cis- and trans-2-pentenenitrile can be recycled into the isomerization stage after distillative removal.

Workup

  1. customafter distillative removal

Sources & evidence

ORD record
ord-17c6923e53e44a41b2c1e095dc419e4d
Source dataset
uspto-grants-2014_07
Patent number
US08772527B2

Linked notes

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