RESEARCH IN NITROMONOMERS AND THEIR APPLICATION TO SOLID SMOKELESS PROPELLANTS.
Abstract
The mono-nitration of cyclic ketones with alkyl nitrates in the presence of potassium t-butoxide affords two products, alpha-mononitroketones and omega-nitro carboxylic esters. The infrared, NMR and ultraviolet spectra of cyclic alpha-nitroketones and of their potassium salts are reported. The reaction of alpha-nitroketones in acidic media was investigated. The major product with the five membered cyclic ketone, 2-nitro-3,5,5trimethylcyclopentanone is a six membered cyclic N-hydroxyimide, 2,6-dioxo-3,3,5-trimethyl-l-hydroxy-laza-cyclohexane. A study of the ring opening reaction of salts of cyclic alpha, alpha'-dinitroketones to alpha, omega-dinitroalkanes was continued. In the case of alpha, alpha'-dinitrocyclopentanone, dipotassium 2-keto1,3-cyclopentanedinitronate and potassium 2-keto-3nitrocyclopentanenitronate are converted to 1,4dinitrobutane in yields of 71% and 84%, respectively, on treatment with formic acid at pH4. In the case of alpha, alpha'-dinitrocyclohexanone, ring cleavage of dipotassium 2-keto-1,3-cyclohexanedinitronate (I) already occurs with carbon dioxide at about pH6 to give 1,5dinitropentane (II) in 82% yield; with aqueous acetic acid at pH5 the yield of V amounts to 88%. 2,6-Dinitrocyclohexanone, a surprisingly stable compund is obtained when pure compound I is treated with hydrogen chloride in anhydrous ether (93.5% yield) or in anhydrous methanol (76% yield).
Document Details
- Document Type
- Technical Report
- Publication Date
- Dec 15, 1964
- Accession Number
- AD0609852
Entities
People
- Henry Feuer
Organizations
- Purdue University