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Synthesis And Evaluation Of New Base Stock Fluids For Gas Turbine Application

Report Number: WADD TR 60-838 Part II
Author(s): Peter T. Kan, John D. Behun, Saiyid M. Naqvi, Marcia A. Jorgensen, Patricia A. Gibson
Corporate Author: Wyandotte Chemicals Corporation
Laboratory: Directorate of Materials and Processes
Date of Publication: 1962-02
Pages: 249
Contract: AF 33(616)-6749
Project: 3044
Task: 73314
AD Number: AD0274768

Progress is reported on the synthesis and evaluation of new pyrazine derivatives for high temperature stable fluid applications. A variety of candidate products which were unsymmetrical 2,3-disubstituted- and 2,3,6-trisubstitutedpyrazines were prepared from the versatile starting compounds 2-chloro-3-methylpyrazine and 2-chloro-3,6dimethylpyrazine. The substituents placed at the 2-position by nucleophilic displacement of the chlorine atom were various phenoxy, alkoxy, anilino and alkylamino radicals. Metalation of the methyl sites afforded the introduction of a number of other types of groups by arylation, aralkylation, alkylation, acylation and silylation reactions. A number of 2,6-disubstitutedpyrazines were prepared via oxidative demethylation of the corresponding intermediate 2,6-disubstituted-3-methylpyrazines. Some simple alkyl substituted pyrazines were also synthesized from the readily available starting compounds methylpyrazine, 2,5- and 2,6-dimethylpyrazines, and tetramethylpyrazine. Thus, a wide variety of pyrazine derivatives were obtained in good to excellent yields by the different synthetic routes.

The screening of pyrazine compounds prepared in this program for thermal and oxidative stability was continued. Based on these tests, classes of compounds containing undesirable linkages were bypassed and materials which showed promise were further screened under more severe conditions at higher temperatures. Correlations of the effect of variation in structure upon physical properties of the substituted pyrazines were made, based on the results of the more drastic screening. These correlations were utilized to guide the direction of the synthesis effort. As a consequence, a stepwise achievement of candidate products with further improved properties was realized.

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