Valeronitrile → Pent-2-enenitrile

HRID 2416181Notes

Reaction equation

HRID 2416181 reaction equation
[CH2:1]([CH:3]([CH:7]([CH2:11][CH3:12])[CH2:8][C:9]#[N:10])[CH2:4][C:5]#[N:6])[CH3:2].C(#N)CCCC.COC(CC)CC#N>>[C:5](#[N:6])[CH:4]=[CH:3][CH2:1][CH3:2].[CH2:11]([CH:7]([CH:3]([CH2:1][CH3:2])[CH2:4][C:5]#[N:6])[CH2:8][C:9]#[N:10])[CH3:12]

Participants

5

Reactant 3

HCID 8061ValeronitrileHCID 130509853-MethoxypentanenitrileHCID 226391723.4-Diethyladiponitrile

Product 2

HCID 25833Pent-2-enenitrileHCID 226391723.4-Diethyladiponitrile

Procedure

The electrolysis was discontinued after 10 h, when 64% of tetramethoxyethane and 76% of pentenenitrile had been converted. Trimethyl orthoformate, methyl formate and formaldehyde dimethyl acetal had formed at the anode in a ratio of 1:0.17:0.1. The main products at the cathode were 3.4-diethyladiponitrile, pentanenitrile and 3-methoxypentanenitrile in a ratio of 1:0.3:0.8. A distillative workup provided the hydrodimerization 20 product of pentenenitrile, namely 3.4-diethyladiponitrile, in 97% purity.

Sources & evidence

ORD record
ord-d85889fa3ed441eca477c98bc9dbef5c
Source dataset
uspto-grants-2004_11
Patent number
US06822124B2

Reaction notes

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