Photodegradation of antibiotic 5-sulfaminouracil in the presence of vitamin B2: a kinetic study.

OBJECTIVE: This paper studies the kinetics and mechanism of the sensitized photodegradation of 5-sulfaminouracil (SFU). This compound is a synthetic bacteriostatic belonging to the sulfa drugs, usually detected in surface water and effluent wastewater.
METHODS: SFU interacts with electronically excited singlet and triplet states of riboflavin (Rf), (1)Rf* and (3)Rf*, respectively. The rate constants for these processes were determined in MeOH-H2O by stationary fluorescence spectroscopy (for kQ(1)) and by laser flash photolysis (for kQ(3)).
RESULTS: SFU is photodegraded by visible light irradiation in the presence of the natural sensitizer (Rf). In competitive processes, (3)Rf* generates the reactive oxygen species superoxide radical anion (O2(•-)) and singlet molecular oxygen [O2((1)Δg)], which are involved in SFU photodegradation. In aqueous solutions, where SFU adopts different forms depending on the pH of the medium, the participation of O2((1)Δg) is predominant. Therefore, the O2((1)Δg)-mediated mechanism was evaluated at pHs 7 and 12, employing perinaphthenone as a synthetic photosensitizer. DISCUSSION: The results indicate that SFU is photodegraded through a relatively efficient process in a neutral environment, whereas it is quickly degraded in alkaline media. This is attributed to the ionization of the sulfamino- group, a substituent in the uracil molecule that exerts an activating power on the molecule. Thus, sensitized photodegradation may be an important tool to reduce the environmental impact of SFU.