Phenol → tert-Butylcatechol

関与物質

反応手順

The product of the hydrocyanation of butadiene using a nickel catalyst and a boron promoter contains 2-methylglutaronitrile, adiponitrile, phenyl t-butylcatecholboronate, and other organo boron compounds such as triphenyl boron, phenyl boronic acid, its anhydride and its phenol and cresol esters. (The t-butylcatecholboronate is formed by the reaction of t-butylcatechol with a boron compound. The t-butylcatechol is an additive used to inhibit the polymerization of butadiene.) This mixture is combined with the alcohol (e.g. ethylene glycol) in at least stoichiometric quantity relative to boron, and the mixture is distilled using a column with sufficient stages to separate out purified adiponitrile as the bottoms, and a mixture of 2-methylglutaronitrile, any excess alcohol (e.g. ethylene glycol), phenol, cresols, and the newly formed boron-complex, (e.g. phenyl ethyleneglycolboronate) as the overheads. (The adiponitrile bottoms may contain some t-butylcatechol at this point, depending on the efficiency of the column.) The overhead mixture is then further distilled in a second column to remove low boilers consisting of any excess ethylene glycol, phenol, cresols, and phenyl ethyleneglycolboronate. 2-methylglutaronitrile is removed as the bottoms, which are then sent to a third column where pure 2-methylglutaronitrile is taken overhead. The bottoms from this last column consist of t-butylcatechol and a small amount of adiponitrile.

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