Tributyltin

Chembox new
Name = Tributyltin hydride
ImageFile = Tributyltin hydride.svg
ImageName = Tributyltin hydride
ImageFile1 = Tributyltin-hydride-3D-balls.png ImageName1 = Tributyltin hydride
IUPACName = Tributylstannane
Section1 = Chembox Identifiers
CASNo = 688-73-3
SMILES = CCCC [Sn] (CCCC)CCCC
Section2 = Chembox Properties
Formula = C₁₂H₂₈Sn
MolarMass = 291.06 g/mol
Density =
MeltingPt =
BoilingPt =

"TBT" redirects here. For the high school located in Tampa, Florida, see Tampa Bay Technical High School."

Tributyltin (TBT, Bu₃SnH) is a trialkyl organotin compound. Tributyltin compounds are a subgroup of the trialkyl organotin family of compounds. They are the main active ingredients in certain biocides used to control a broad spectrum of organisms, and these compounds are being considered for inclusion in the Rotterdam Convention.cite news|url=http://www.pic.int/incs/crc3/n14)/English/K0654009%20CRC3-14.pdf|title=Draft Decision Guidance Document for Tributyltin Compounds|last=Secretariat for the Rotterdam Convention on the Prior Informed Consent Procedure for Certain Hazardous Chemicals and Pesticides in International Trade|date=26 November 2006|publisher=United Nations Environment Programme|accessdate=2008-10-06]

Uses

Uses include wood preservation and preservation, antifouling pesticide in marine paints, antifungal action in textiles and industrial water systems, such as cooling tower and refrigeration water systems, wood pulp and paper mill systems, and breweries. Tributyltin oxide is the widely used compound in TBT–containing commercial products.

Use in organic synthesis

Tributyltin is a useful reagent in organic synthesis. Combined with azobisisobutylonitrile, tributyltin generates radicals by removing a hydrogen atom from the molecule of interest.Fact|date=December 2007

Toxicity

TBT compounds are considered as toxic chemicals which have negative effects on human and environment. Tributyltin compounds are moderately to highly persistent organic pollutants that bioconcentrate up the marine predators' food chain. One common example is leaching of TBT from marine paints into the aquatic environment, causing irreversible damage to the aquatic life.

TBT is harmful to some marine organisms, including the dog whelk. TBT causes dog whelks to suffer from imposex: females develop male sexual characteristics such as a penis. [cite journal | doi = 10.1016/0025-326X(95)00120-C | author = Dan Minchin, Eberhard Stroben, Jörg Oehlmann, Barbara Bauer, Colm B. Duggan and Michael Keatinge | title = Biological indicators used to map organotin contamination in Cork Harbour, Ireland | year = 1996 | journal = Marine Pollution Bulletin | volume = 32 | pages = 188] This causes them to become infertile or even die. In severe cases males can develop egg sacs.

Tributyltin, dibutyltin and toxicity to marine mammals

Studies have shown that wild, dead sea otters (Enhydra lutra) and stranded bottlenose dolphins can have extremely high levels of tributyltin in their livers.cite journal |author=Murata S, Takahashi S, Agusa T, Thomas NJ, Kannan K, Tanabe S |title=Contamination status and accumulation profiles of organotins in sea otters (Enhydra lutris) found dead along the coasts of California, Washington, Alaska (USA), and Kamchatka (Russia) |journal=Marine pollution bulletin |volume=56 |issue=4 |pages=641–9 |year=2008 |month=April |pmid=18304586 |doi=10.1016/j.marpolbul.2008.01.019 |url=http://linkinghub.elsevier.com/retrieve/pii/S0025-326X(08)00025-8] Both tributyltin and dibutyltin, a metabolite byproduct, cause immunosuppresion, leading to secondary infections.Fact|date=December 2007 This was supported by the finding that otters dying of infectious causes tend to have higher levels of tissue butyltins than those dying of trauma or other causes. [Kannan et al. 1998. Butyltin residues in Southern sea otters (Enhydra lutris nereis) found dead along California coastal waters. Environ. Sci. Technol. 32:1169-1175]

TBT has also been blamed by hearing experts for causing hearing loss in mammalian top predators such as toothed whales. [cite news
author=Matt Apuzzo
url=http://www.cbsnews.com/stories/2005/01/28/tech/main670083.shtml
title=Whale Deafness Linked To Chemical
publisher=Associated Press via CBS News
date=2005-01-28
accessdate=2008-07-30] [cite journal
title=Control of Mammalian Cochlear Amplification by Chloride Anions
author=Santos-Sacchi Joseph, Song Lei, Zheng Jiefu, Nuttall Alfred L
url=http://www.jneurosci.org/cgi/content/full/26/15/3992
date=2006-04-12
journal=Journal of Neuroscience
volume=26
issue=15
pages=3992–3998
doi=10.1523/JNEUROSCI.4548-05.2006
pmid=16611815 ]

Tributyltin toxicity to marine invertebrates

TBT is extremely toxic to molluscs. In the case of bivalve larvae, the effective concentration (EC50) of TBT is 1000 times lower than that of any other toxic compound introduced into the marine environment. [see Fig.15 on p. 134 in: cite journal
author=His E, Beiras R, Seaman MNL
year=1999
title=The assessment of marine pollution: bioassays with marine embryos and larvae
journal=Advances in marine biology
issn=0065-2881
volume=37
pages=1–178
doi=10.1016/S0065-2881(08)60428-9] TBT also causes imposex in marine gastropods and is probably responsible for reductions in their populations in zones with important ship traffic.Fact|date=December 2007

References

External links

* [http://www.ncl.ac.uk/barnacles] Newcastle University Biofouling Group
* [http://www.epa.gov/waterscience/criteria/tributyltin/tbt-final.pdf "Ambient Aquatic Life Water Quality Criteria for Tributyltin (TBT)"] US Environmental Protection Agency, December 2003