Tributyltin chloride

325.508

325.51

215-958-7

CA82T4QR5F

22323

DTXSID3027403

Liquid|Colorless liquid

29310095

0

4.76

Clear, colorless liquid.

1.20 g/cm³ @ Temp: 20 °C

-19 °C

171-173 °C @ Press: 25 Torr

>230 °F

n 20/D 1.492(lit.)

Insoluble in cold water but hydrolyzes in hot water

2-8ºC

<0.01 mm Hg ( 20 °C)

The utility of triorganotin halides and their application as starting materials for most other triorganotin compounds results from the ease of nucleophic displacement. /Triorganotin halides/|Triorganic tin compounds of strong acids are genrally quite stable to hydrolysis under neutral conditions. Under basic conditions, the hydroxide or bisoxide forms. Strong acids, halogens, and other electrophiles can cause cleavage of the tin-carbon bondds with the formation of diorganotins. /Triorganotins/

II

6.1

UN 2788 6.1/PG 3

3

R21; R25; R36/38; R48/23/25; R50/53

35-36/37/39-45-60-61-26

WH6820000

T,N

Stable at room temperature in closed containers under normal storage and handling conditions.

P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P312, P314, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501

H301

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P272, P273, P280, P281, P301+P310, P302+P352, P305+P351+P338, P308+P313, P312, P314, P321, P322, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, P405, and P501|Aggregated GHS information provided by 58 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P312, P314, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|P260, P264, P270, P280, P301+P310, P302+P352, P305+P351+P338, P309+P311, P321, P330, P332+P313, P337+P313, P362, P405, and P501

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

A severe eye irritant.

SEDIMENT: The concn of tributyltin species in sediment (upper 2 cm) from Toronto Harbor (6 sites) was 0.08-1.28 mg Sn/kg dry weight(1). The concn of tributyltin in sediment from two harbors along the Rhine River in Germany were 13 and 182 ng Sn/g dry wt; the high level is from a small harbor that is crowded with pleasure crafts that are believed to be responsible for large releases of tributyltin(2). The concns of tributyltin in harbor sediment in Lake Lucerne, Switzerland was high, up to 2800 ug/g(3). High concns were restricted to the upper 7 cm and decreased significantly below. The dating of cores suggest that tributyltin may persist for more than a decade in sediment. Small amounts of the mono- and di-butyltin were also found in the upper layers of sediment(3).|MARINE SEDIMENT: While concns of tributyltin in surface water in San Diego Bay declined after restrictions on the use of antifouling paint containing tributyltin in California were enacted. Tributyltin levels in sediment were variable and did not reflect the decreases in levels in the water column. Mean tributyltin levels at 14 sites ranged from 7 to 430 ng/g dry wt between Jan 1989 and July 1990 with the higher values being at yacht basins and naval yards(1). Intertidal sediments at a restricted site downstream from the shipyards in the Sado estuary, Portugal reached levels of 520 ng/g dry wt for tributyltin, over an order of a magnitude higher than samples taken in March(2). This has been ascribed to the cleaning of ships in spring and points up the large seasonal variability in anthropogenic organotin levels. Intertidal and marine levels of tributyltin at other sites in the Sado Estuary were 12-21 and 21 ng/g, respectively. Sediment tributyltin concns from Chesapeake Bay include: 141-1390 ug/kg dry wt at six stations in or near marinas on a northern tributary; 23-290 ug/kg dry wt in Sarah and Kings Creek in Virginia and 920-1300 ug/kg dry wt in the Sarah Creek area(3).

LD50 Rat oral 129 mg/kg|LD50 Mouse oral 60 mg/kg

Tributylchlorostannane's production and use as an intermediate(1) may result in its release to the environment through various waste streams(SRC). Tributylchlorostannane's production and former use as an rodenticide(1) may have resulted in its direct release to the environment(SRC). Potential sources of organotin compounds in the Rhine River in Germany are the manufacture and industrial use of organotin compounds and the effluents of municipal sewage treatment plants(2). Municipal wastewater has been shown to contain considerable quantities of tributyltin that may be released in surface water(3).

TERRESTRIAL FATE: If tributylchlorostannane is released to soil, it will dissociate and form tributyltin(SRC). Tributyltin will be expected to strongly bind to soil(1). Tributyltin is susceptible to biodegradation and is reported to have a half-life in soil of 15-20 weeks(2). Tributyltin may slowly photodegrade on the soil surface(3) but would not be expected to volatilize from near-surface soil(4,5).|AQUATIC FATE: If tributylchlorostannane is released to water, it is expected to dissociate to form tributyltin cations(1). Tributyltin is stable (as defined by lack of debutylation) in distilled, deionized water kept in the dark at 20 °C for over 63 days at pH between 2.9 and 10.3(2) and no degradation of tributyltin was observed in 11 months in KCN-poisoned water sediment mixtures(3). Tributyltin is susceptible to biodegradation in water with half-lives of between 6 days and 35 weeks reported in water and water-sediment mixtures, many of which had been previously contaminated with tributyltin species(3,4). Results from experiments in water and water sediment mixtures have indicated that abiotic degradation of tributyltin species will be limited to direct photolysis in surface water(2,3,5). The half-life for sunlight photolysis of tributyltin was determined to be >89 days both in distilled water and lake water(2). Based upon Kocs of up to 90,800, tributyltin may strongly bind to sediment(3,6,7). Based upon BCFs of >6,000(8), tributyltin cation can strongly bioconcentrate in various aquatic organisms(SRC). Based upon laboratory observations(2) and the fact that tributyltin cationis the dominant species in water, volatilization from water is not expected to be an important environmental pathway for tributylchlorostannane(SRC).|AQUATIC FATE: Radiolabeled tributyltin was added to a 13 cu m marine mesocosm with near natural water column and benthos in summer and monitored for 278 days to study the behavior of tributyltin and its degradation products(1). The removal of tributyltin from the water column was the result of biological degradation, scavenging to the sediment and presumed loss to the atmosphere with an overall removal half-life of 6-12 days(1). Tributyltin compounds in seawater are degraded in summer to give dibutyltins, hydroxylated tributyltins, hydroxylated dibutyltins, carboxylated derivatives and monobutyltin(2). Laboratory studies show that the half-life of tributyltin in sediment is in the range of years(3). Degradation is slower under anaerobic conditions than under aerobic conditions; half-lives in anaerobic sediment is in the range of 2-3 years(3).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tributylchlorostannane, which has an estimated vapor pressure of 0.013 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase tributylchlorostannane is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 9.0 hours(SRC), calculated from its rate constant of 43X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). There are no experimental studies relating to tributylchlorostannane's photodegradation in air. However, tributyltin species present in water solutions have been observed to slowly photodegrade in sunlight(4).

The rate constant for the vapor-phase reaction of tributylchlorostannane with photochemically-produced hydroxyl radicals has been estimated as 43X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 9.0 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Tributylchlorostannane may be susceptible to photooxidation by hydroxyl and peroxyl radicals in water via abstraction of hydrogen from the butyl groups(SRC). Abstraction of a hydrogen atom from the hydride part of the compound by these oxidants to form the tributyltin radical may occur since the first step in the accepted mechanism for the reduction of alkylhalides by trialkytin hydrides is the formation of the trialkyltin radicals via reaction with a radical initiator(2). Tributylchlorostannane may be susceptible to direct photolysis based upon the absorption of UV light >290 nm by tri-, di-, and monobutyltin compounds(3).

The BCFs in crucian carp (Carassius carassius grandoculis) obtained in a 7-day experiment were 589 (muscle), 457 (vertebra); 5012(liver); and 3162 (kidney)(1). BCFs for tributyltin in oysters ranged from 1000 (water concn 0.15 ug/l) and 5000 (water concn 1.25 ug/l)(2). In studies in which the bioaccumulation and elimination of tributyltin in Red Sea bream (Pagrus major) was by direct uptake from water, from diet, and from both simultaneously, about a quarter of the bioaccumulation was due to dietary uptake(3). The accumulation factor for dietary uptake was 0.26-0.38 on a dry wt basis. The elimination rate was 0.031-0.037/day and was independent of the source of uptake, water or diet. Bioaccumulation was also independent of the form of tributyltin in the diet. Marine mussels (Mytilus graynus) collected in a lightly contaminated area and transplanted to a highly contaminated area had a BCF of 10,500 for tributyltin; the half-life was 4.68 days(3). Blue mussels (Mytilus edulis) collected from a highly contaminated area and transplanted to a lightly contaminated area had a BCF of 10,400 for tributyltin; the half-life was 4.82 days(4). Oligochaetes accumulate sediment-associated tributyltin, thus making it available to bottom feeding fish(2). According to a classification scheme(5), BCF values of >6,000(6) suggest bioconcentration of tributylchlorostannane (as tributyltin) in aquatic organisms is very high(SRC).

If tributylchlorostannane is released to soil, it will dissociate to form tributyltin(SRC). Tributyltin will be expected to strongly bind to soil; tributyltin should not leach through soil(2). No leaching of tributyltin was observed in several soils (clay, sand, topsoil and silt) during periods as long as 16 weeks(2). Tributyltin binds strongly to sediment with the distribution constant for Toronto Harbor sediment and water as 2180 at 20 °C(3). Very little tributyltin or inorganic tin was released from unshaken sediment in 10 months. However, other studies have shown that tributyltin does not adsorb appreciably to suspended particulate matter and that it is primarily associated with the dissolved fraction of estuarine water(1,4). This is in line with the observation that addition of humic acids or kaolin clay material does not significantly affect the tributyltin BCF in mussels(5), suggesting that tributyltin species are only weakly bound to these materials(5). Studies on the adsorption of tributyltin to a wide variety of sorbents yield sorption coefficients ranging from 110 to 350,000 l/kg, but the majority of sorption coefficients are about 1,000 L/kg(6). Adsorption is relatively fast (hours) and reversible. In a 278-day marine mesocosm experiment, the transport rate from the water column to sediment was 0.045/day(7). The distribution coefficient between dissolved state and particulate matter calculated from data between days 2-19 was 60,000 (standard deviation 30,000). Other investigators obtained distribution constants for adsorption of tributyltin to particulate matter and sediment of 3400-9300 L/kg and 200-55,000 L/kg, respectively; values were a function of sediment type and location(7). The Freundlich parameters, log k and 1/n, for tributyltin to sediment were 1.07 and 0.359, respectively(8).

The volatilization of tributylchlorostannane from natural waters is not expected to be a significant process based upon its hydrolysis to tributyltin(SRC). Volatilization of tributyltin species from water is negligible over a period of at least 2 months(1). In a 278-day marine mesocosm experiment, loss of tributyltin from the water interface to the atmosphere occurred at a rate of 0.075/day(2). It was found that loss was preceded by rapid transport to the surface microlayer followed by volatilization, or photodegradation and volatilization.

SURFACE WATER: The concn of tributyltin species in unfiltered subsurface water from Toronto Harbor (7 sites) was 0.01-0.20 ug Sn/l(1). Tributyl tin was found in unfiltered subsurface water and unfiltered surface microlayers of various lakes, rivers, and harbors in Ontario at levels ranging from 0.01-2.91 and 0.15-60.7 ug/l, respectively(2). Water samples taken over several months in the Rhine River at Mainz in 1989 did not contain detectable levels of tributyltin(3). In 3 harbors at Mainz and Wiesbaden, tributyltin levels were 10, 21, and 73 ng Sn/l. The highest concn was in a small harbor crowded with pleasure crafts. It was been reported that most tributyltin is released by pleasure crafts(3).|SEAWATER: Various investigators reported tributyltin concns in the water column of various southern and northern areas of Chesapeake Bay; twenty week average tributyltin concns ranged from 16 to 121 ng/l but individual values as high as 1800 ng/l were found in a marina(2). Higher levels were found in marina areas and peak levels occurred during the early part of boating season when freshly painted boats entered the water. Another investigator obtained tributyltin concns ranging from 1.9 to 26 ng Sn/l and <1 to 66 on the Elizabeth River (10 locations) and Sarah Creek (n=8), both rivers feeding into the lower Chesapeake Bay(3). Concentrations of tributyltin in surface water in San Diego Bay declined after restrictions on the use of antifouling paint containing tributyltin in California were enacted. Mean tributyltin levels between October 1986 and February 1988 ranged from 100-110 ng/l in the yacht region and 5 to 14 ng/l in the naval, North Bay and South Bay regions(1). Between April 1989 and July 1990, these levels declined to 18-28 ng/l and 1.5-5 ng/l, respectively.

Occupational exposure to tributylchlorostannane may occur through dermal contact with this compound at workplaces where tributylchlorostannane is produced or used. The general population will be exposed to tributylchlorostannane (as tributyltin) via the ingestion of contaminated fish and other seafood. (SRC)

10 organotins including di-n-butyltin dichloride, mono-n-butyltin trichloride, tetrabutyltin, di-n-butyl(2-ethylhexyl)tin chloride, di-n-butylisobutyl tin chloride, di-n-butylsecbutyl tin chloride and others.

TBTC chloride

Technical grade (96.0% tri-n-butyl chloride)

All other chemical product and preparation manufacturing|Stannane, tributylchloro-: ACTIVE|The use of tributyltin compounds in antifoulants are restricted because of their toxicity to aquatic organisms and EPA is cooperating in international efforts for a global phase-out.|The stoichiometric reaction of Grignard or alkylaluminum reagents with stannic chloride to give trialkyltin chloride usually gives a mixture of products. Only in a few cases is it possible to alkylate tin tetrachloride directly to the triorganotin in good yield with few by-products using a Grignard reagent.

NIOSH Method 5504. Organotin Compounds. HPLC. Detection limit = 0.002 mg/cu m.