Preparation of muconic acid mononitriles and copper(II)-ammonia reagent therefor
AssigneeAllied Corporation
InventorsTimothy R. Demmin, Milorad M. Rogic
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Abstract
Substituted and unsubstituted phenols, catechols and orthobenzoquinones are converted to muconic acid mononitriles by reaction with copper(II)-ammonia reagents. The copper(II)-ammonia reagents can be prepared by the reaction of cuprous chloride with oxygen or air in liquid ammonia or in ammonium hydroxide or in pyridine followed by addition of ammonia or ammonium hydroxide. The muconic acid mononitriles are useful as monomers or comonomers and as intermediates in the manufacture of substituted and unsubstituted 6-aminocaproic acids, caprolactams and polyamides.
Claims13
A method of forming a copper(II)-ammonia reagent which comprises oxidizing a soluble cuprous salt with oxygen in an organic solvent containing a nitrogen with an unshared electron pair and reacting the product with ammonia or ammonium hydroxide.
A copper(II)-ammonia reagent active for the conversion of catechols to muconic acid mononitriles being suspendable in at least one organic solvent containing a nitrogen with an unshared electron pair and having an empirical formula when isolated from such an organic solvent of
- (CuO)(CuX.sub.2).sub.y (NH.sub.3).sub.z
- where X is a monovalent anion, y is between about 0.2 and about 1 and z is between about 2 and about 4.
Dependencies are inferred from the claim text.