The majority of adiponitrile is prepared by the nickel-catalysed hydrocyanation of butadiene, as discovered at duPont. The net reaction is:
- CH2=CHCH=CH2 + 2 HCN → NCCH2CH2CH2CH2CN
The process involves several stages, the first of which involves monohydrocyanation (addition of one molecule of HCN), affording isomers of pentenenitriles as well as 2- and 3-methylbutenenitriles. These unsaturated nitriles are subsequently isomerized to the 3-and 4-pentenenitriles. In the final stage, these pentenenitriles are subjected to a second hydrocyanation, in an anti-Markovnikov sense, to produce adiponitrile.
Research has shown that the 3-pentenenitrile, formed in the first hydrocyanation, can undergo alkene metathesis to give dicyanobutenes, which are readily hydrogenated as described above.
The other major industrial route involves electrosynthesis, starting from acrylonitrile, which is dimerized:
- 2 CH2=CHCN + 2 e- + 2 H+ → NCCH2CH2CH2CH2CN
The electrolytic coupling of acrylonitrile was discovered at Monsanto Company.
Other articles related to "modern routes, route":
... Route 206 New Jersey State Route 10 County Route 521 (New Jersey) County Route 519 (New Jersey) County Route 626 (New Jersey) ...
Famous quotes containing the words routes and/or modern:
“The myth of independence from the mother is abandoned in mid- life as women learn new routes around the motherboth the mother without and the mother within. A mid-life daughter may reengage with a mother or put new controls on care and set limits to love. But whatever she does, her childs history is never finished.”
—Terri Apter (20th century)
“O born in days when wits were fresh and clear,
And life ran gaily as the sparkling Thames;
Before this strange disease of modern life,
With its sick hurry, its divided aims,
Its head oertaxed, its palsied hearts, was rife”
—Matthew Arnold (18221888)