The methylol reactions of phenylacetoguanamine, isobutyloguanamine and ω-cyanovaleloguanamine with formaldehyde were studied in dioxane-water mixture (1 : 1 by volume).
The functionalities of these compounds against formaldehyde were found to be 3. 6, 3. 6 and 3. 5, respectively. The rate constants and equilibrium constants were determined under the conditions of formaldehyde/guanamine mol ratio 4. 0 and pH 9.2-9.5, and the following results were obtained.
Guanamine Derivative Reaction Temperature (°C) Rate Constant (mole
-1. min
-1) Equilibrium Constant
Phenylaceto guanamine 30 2.2 X 10
-2 6.67 40 4.4 X 10
-2 5.87 50 9.3 X 10
-2 5.05 60 27.6 X 10
-2 4.31
iso-Butylo guanamine 30 1.1 X 10
-2 7.31 40 2.6 X 10
-2 6.46 50 6.0 X 10
-2 5.21 60 14.1 X 10
-2 4.46
w-Cyanovalelo guanamine 30 1.6 X 10
-2 7.23 40 3.7 X 10
-2 6.38 50 8.6 X 10
-2 5.12 60 31.6 X 10
-2 4.38
The activation energies were 16. 9, 17.0 and 18.5 kcal/mol, the heats of reaction were 3.1, 3.3 and 3.3 kcal/mol, respectively. It is suggested that the reaction mechanisms for these reactions were essentially the same
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