Patent GB-966251-A (GB)
Title: Novel polycyclic nitrogen-containing compounds
IPC: A23K50/15
Filed: 1962-01-22
Abstract: A fertilizer comprises a tetra azaphenalene of the general formula <FORM:0966251/C1/1> in which the rings are saturated or unsaturated and in which the substituents R and R1 are hydrogen atoms or alkyl, cycloalkyl, aryl, aralkyl or alkaryl hydrocarbon groups, all substituent groups R being the same and all substituents R1 being the same (see Division C2).ALSO:Novel tetraazaphenalenes of the general formula: <FORM:0966251/C1/1> in which the rings are saturated or unsaturated: <FORM:0966251/C1/2> and R and R1 are hydrogen atoms, alkyl, cycloalkyl, aryl, aralkyl or alkanyl hydrocarbon groups, all R groups being the same and all R1 groups being the same are made by reacting an alpha beta-mono unsaturated alkenal with ammonia in certain defined alcohols, at above 80 DEG C. at sufficient superatmospheric pressure to maintain the reactants in the liquid phase, after which the reaction product may or may not be catalytically dehydrogenated to form ring double bonds.  Preferred operating conditions in the synthesis are 100-200 DEG C., 35-100 ats. absolute, the use of an alkanol particularly methanol as reaction mechanism, starting materials acrolein methacrolein, crotonaldehyde, and the use of a palladium catalyst at 100-350 DEG C. for the dehydrogenation. The compounds particularly claimed per se are those wherein the groups R2R1 are hydrogen, alkyl and methyl.  The examples describe the synthesis of dodecahydro-1,4,7,9b-tetraazaphenalene, 2,5,8- and 3,6,9-trimethyl, 2,5,8-triphenyl, 2,3,5,6,8,9-hexamethyl dodecahydro-1,4,7,9b-tetraazaphenalenes and the corresponding dehydrogenated tetraazaphenalenes. Raney nickel is also employed as dehydrogenation catalyst and many others suitable are listed. The colour of the reduced product may be improved by catalytic hydrogenation. For uses of the products see Divisions A2, C1, C3 and C4.ALSO:Novel tetra azaphenalenes of the general formula: <FORM:0966251/C3/1> in which the rings are saturated or unsaturated and in which the substituents R and R1 are hydrogen atoms or alkyl, cycloalkyl, aryl, aralkyl or alkaryl hydrocarbon groups, all substituent groups R being the same and all substituents R1 being the same are said to be useful as curing agents for epoxy resins.  For their preparation (see Division C2).ALSO:Novel tetra azaphenalenes of the general formula <FORM:0966251/C4-C5/1> in which the rings are saturated or unsaturated and in which the substituents R and R1 are hydrogen atoms or alkyl, cycloalkyl, aryl, aralkyl or alkaryl hydrocarbon groups, all substituent groups R being the same and all substituents R1 being the same are said to be useful as dyes, colour filter components and acid base indicators.  For their preparation (see Division C2).ALSO:Novel tetra azaphenalenes of the general formula <FORM:0966251/A1-A3/1> in which the rings are saturated or unsaturated and in which the substituents R and R1 are hydrogen atoms or alkyl, cycloalkyl, aryl, aralkyl or alkaryl hydrocarbon groups, all substituent groups R being the same and all substituents R1 being the same, are useful as cattle feed supplements.  For their preparation see Division C2.