Synthesis and identification of meta-(4-bromobenzyloxy) benzaldehyde thiosemicarbazone (MBBOTSC) as novel ligand for cadmium extraction by ultrasound assisted-dispersive-ionic liquid-liquid micro extraction method

Abdolreza Hassanzadeh,Ahmad Salarifar,Ali Asadipour,Bagher Amirheidari,Yaghoub Pourshojaei

doi:10.24200/amecj.v4.i04.161

Abstract

In this research, meta-(4-bromobenzyloxy) benzaldehyde thiosemicarbazone (MBBOTSC) as a novel ligand was synthesized from the reaction between meta-(4-bromobenzyloxy) benzaldehyde and thiosemicarbazide under basic condition in water and ethanol as solvents. Ligand has the ability to chelate ions and therefore, it was used to form a complex and extract ions. Then, the cadmium ions in water and wastewater samples were separated based on MBBOTSC by ultrasound assisted-dispersive-ionic liquid-liquid microextraction method (USA-D-ILLME) before determination by AT-F-AAS. The MBBOTSC ligand was added to the mixture of the ionic liquid/acetone (IL/AC, [OMIM][PF6]) and then injected by syringe to 50 mL of water samples at pH 6-7. The sample was put into the ultrasonic accessory for 5 minutes, after complexation (Ligand-Cd; RS…Cd….RS), the water sample was centrifuged for 3 min for phase separation. Due to complexation and back-extraction of Cd in liquid phase, the amount of Cd ions in the water samples was determined by AT-F-AAS . In optimized conditions, the Linear ranges and LOD for 50 mL of water samples were obtained 1-36 μg L-1 and 0.3 μg L-1, respectively (Mean RSD= 1.26%). The validation results were successfully achieved by spiking real samples and using ET-AAS.

Highlights

Thiosemicarbazones (TSCs) are an important class of organic compounds containing N and S elements that have various uses and properties [1]
Synthesis of TSC is performed in different ways: a) it is a two-step pathway in which hydrazine reacts with isothiocyanate and the product with aldehyde or ketone, which leads to TSCs [9], b) it is the opposite of pathway a, ie hydrazine first reacts with aldehydes or ketones and the resulting compound reacts with isothiocyanate [10], c) it is a 4-step process, in which hydrazine first reacts with carbon disulfide and the resulting intermediate reacts with methyl iodide to form methylhydrazine thiocarbamate, eventually nucleophilic substitution with amines and a condensation reaction with an aldehyde or ketone produces TSC [11]
In continuation of our research on the synthesis of various compounds [12,13,14,15] and recent report introducing penicillamine as a metal chelator [16], meta-(4-bromobenzyloxy) benzaldehyde thiosemicarbazone (MBBOTSC) as ligand containing sulfur and nitrogen has proposed as cadmium chelator

Summary

Introduction

Thiosemicarbazones (TSCs) are an important class of organic compounds containing N and S elements that have various uses and properties [1]. These compounds as Schiff base ligands have been widely used to form complexes and to separate metals [2]. In continuation of our research on the synthesis of various compounds [12,13,14,15] and recent report introducing penicillamine as a metal chelator [16], MBBOTSC as ligand containing sulfur and nitrogen has proposed as cadmium chelator. For healthy peoplee,, the mean caaddmmiiuumm concentration iinnhhuummaannsesreurmumsamsapmlepsleis ilseslsestshtahnan0.02.2μgμgLL-1-[12[255].].SSoo,,tthhee ddeetteermination of caaddmmiiuumm iinn waterr sampleess is an important concern foorr controllliinngg toxicciittyy [26,2277]]. Solid-phase exxttrraaccttiioonn ((SSPPEE)) and liquid-liquuiidd micro extraction (LLLLMMEE)) aree preferrrreedd to other techniquueess for ultratrace cadmium determination and separation in water samples [ 32,33]

H HN NN S O

Findings

Mechanism of cobalt extraction cadmium with MBBOTSC ligand was studied