Synthesis, Identification and Surface Active Properties of Some Nonionic Surfactants Containing Quinazolinone Ring

Suaad M.H. Al-Majidi, Haider M.M. Al-tamimy
2017 IOSR Journal of Applied Chemistry  
This research includes synthesis of new heterocyclic derivatives of quinazolinone and studying the possibility for their application as surfactants. The preparation process started by the reaction of pentadecanoyl chloride with anthranilic acid gave 2-pentadecyl-4H-benzo[3,1]oxazin-4-one [1] which was used as starting material to synthesis some heterocyclic compounds by a reaction with nitrogen nucleophiles. Compound [1] as starting material reacted by three ways. The first way react Compound
more » ... ] with semicarbazide, thiosemicarbazide and phenylsemicarbazide in pyridine as solvent to obtained [1-(4-oxo-2pentadecylquinazolin-3(4H)-yl) urea [2], thiourea [3], phenylthiourea [4] respectively]. The second way include the reaction of Compound [1] with 99% hydrazine hydrate to produce 3-amino-2-pentadecylquinazolin-4(3H)-one [5] , then converted to amino derivatives [6-8] by the reaction of Compound [5] with different halogenated compounds such as (benzoyl chloride, acetyl chloride and chloro acetyl chloride ) in DMF and pyridine as catalyst. The third way include the reaction of compound [1] with different substituted amine and amide compounds (thiourea, hydroxylamine hydrochloride, glycine, ammonium acetate and phenyl hydrazine) respectively to obtain derivatives of quinazoline [9] [10] [11] [12] [13] [14] . The produced compounds [2,4,5,7 and 12] react with propylene oxide in different moles (n=3, 5 and7) to yield novel groups of nonionic compounds having a function as surface active agents. The surface active properties like surface tension and interfacial tension, wetting time, cloud point, emulsion stability, foam height and CMC of these compounds were measured and showed a pronounced surface activity, good emulsifying properties and highly foaming in some of these compounds. Newly synthesized compounds were identified via spectral methods; their [FTIR and some of them by 1 HNMR, 13 C-NMR] and measurements of some of its physical properties.
doi:10.9790/5736-1005013746 fatcat:baoxgnwzojbmrnm2t4o5yprc7m