Of phenyltin compounds

Langner, M., Gabrielska, J., Kleszcynska, H. and Pruchnik, H. (1998). Effect of phenyltin compounds on lipid bilayer organization, Appl. Organomet. Chem., 12, 99-107. 

In spite of the excellent yields this process is extremely labour-consuming and dangerous especially in large scale. It is used mainly for the preparation of phenyltin compounds. The alkylaluminium treatment is also an industrial process ... 

Soderguist and Crosby, 353, point out that the chemistry of phenyltin compounds is dominated by the lability of the bond associated with the accompanying anionic group as compared to the relative stability of the carbon-tin bond. For example, both Ph3SnCl and (Ph3Sn)20 exist in water as Ph3Sn0H, which, in the presence of excess acetate, partitions into dichloromethane as... 

Butyl- and phenyltin compounds, particularly the trialkylated forms are very toxic to marine life. The antifouling paints, mainly tributyltin (TBT) but also triphenyltin (TPhT) caused and continue to cause substantial damage because of their slow biodegradation and their accumulation in the biota, notwithstanding a substantial reduction in application through multi-national regulation). 

The analytical response of inorganic and organic tin compounds of formula R SnX 4 was studied for direct hydride generation and measurement with a non-dispersive AFD (atomic fluorescense detector). Tributyltin and phenyltin compounds gave unsatisfactory results. This was corrected by warming the sample with a dilute Br2-HN03 solution37. 

Butyltin and phenyltin compounds in samples of environmental, industrial and biological origin can be determined by the following general scheme42-48 ... 

A considerable number of organometallic species of germanium, tin and lead have been detected in the natural environment. A number of these are nonmethyl compounds which have entered the environment after manufacture and use (e.g. butyltin and phenyltin compounds by diffusion from antifouling paints on boats, and ethylleads from leaded gasoline). Only a few methyl compounds are now manufactured and used (e.g. some methyltin compounds are used as oxide film precursors on glass)1. 

Phenyltin compounds significantly inhibit natural killer cell function and possible natural killer cell-mediated immunotoxic potential of these compounds in humans (Whalen et al. 1999). The toxic potential followed the order of triphenyltin > diphenyltin > monophenyltin however, phe-nyltins were less toxic than butyltins to human natural killer cells (Whalen et al. 1999). 

Whalen, M.M., S. Hariharan, and B.G. Loganathan. 1999. Inhibition of human natural killer (NK) cell function in vitro by phenyltin compounds. Book of Abstracts, Part 1, ENVR 113. 218th American Chemical Society National Meeting, New Orleans, August 22-26, 1999. 

Rozycka-Roszak, B., Pruchnik, H. and Kaminski, E. (2000). The effect of some phenyltin compounds on the thermotropic phase behaviour and the structure of model membranes, Appl. Organomet. Chem., 14, 465 -72. 

In situ derivativization and supercritical fluid extraction has been used for the simultaneous extraction and determination of butyl tin and phenyltin compounds in soils and sediments [73]. 

Cal et al. [85] carried in situ derivativisation and supercritical fluid extraction for the simultaneous determination of butyltin and phenyltin compounds in sediments. 

For the determination of organotin compounds (tributyltin, triphenyltin, triethyltin, and tetra-ethyltin) a MAE is proposed before the normal phase (NP) HPLC/UV analysis [35], In organotin and arsenic speciation studies, hydride generation is the most popular derivatization method, combined with atomic absorption and fluorescence spectroscopy or ICP techniques [25,36], Both atmospheric pressure chemical ionization (APCI)-MS and electrospray ionization ESI-MS are employed in the determination of butyltin, phenyltin, triphenyltin, and tributyltin in waters and sediments [37], A micro LC/ESI-ion trap MS method has been recently chosen as the official EPA (Environmental Protection Agency) method (8323) [38] it permits the determination of mono-, di-, and tri- butyltin, and mono-, di-, and tri-phenyltin at concentration levels of a subnanogram per liter and has been successfully applied in the analysis of freshwaters and fish [39], Tributyltin in waters has been also quantified through an automated sensitive SPME LC/ESI-MS method [40],... 

In situ derivatisation and supercritical fluid extraction have been applied to the determination of butyl and phenyltin compounds in soils [43]. 

Harino, H., Fukushima, M., Yamamoto, Y., Kawai, S., Miyazaki, N., 1998a. Contamination of butyltin and phenyltin compounds in the marine environment of Otsuchi Bay, Japan. Environ. Pollut. 101, 209-214. 

A rapid method of analysis of organo-tin compounds in sediment and biological CRMs was developed (Pereiro et al., 1997). Ethylated butyltin compounds were separated isothermally on a multicapillary (MC) gas chromatographic column in less than 30 s as compared with 5-10 min on a regular capillary column. The MC column consisted of a bundle of about 900 1 m-long, 40 mm i.d. coated capillaries. The column was connected to a microwave-induced plasma atomic emission spectrometer. Phenyltin compounds were also included in the procedure. Detection limits of MBT, DBT and TBT were about 0.2ngml 1 (as tin). 

This example illustrates a range of problems that are symptomatic in quantitation and standardisation which appear in speciation analysis and in determination of organic compounds in solids. Organotin compounds (e.g. methyltin, butyltin, phenyltin) comprise one of the most thoroughly studied groups of organometallic compounds found in environmental samples. 

Pellegrino, C., P. Massanisso, and R. Morabito. 2000. Comparison of twelve selected extraction methods for the determination of butyl- and phenyltin compounds in mussel samples. Trends Anal. Chem. 19 97-106. 

The structures of both the phenyl and 2,5-dimethylphenyl tin clusters were established by single-crystal X-ray diffraction. Under similar conditions, toluene was stannylated to produce a mixture of organotin compounds. Bromination of this mixture yielded 3-bromotoluene and 4-bromotoluene in a 2 1 ratio, with trace amounts of 2-bromotoluene. Similarly, PhBr was produced upon treatment of the phenyltin product with aqueous Br2. No applications of the stannylation reactions have yet been reported. 

---