비스(트리노르말부틸틴)옥사이드

Bis(tributyltin) oxide

HCID 16682746

기본 정보

CAS
56-35-9
표준 SMILES
CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[O][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC
InChIKey
APQHKWPGGHMYKJ-UHFFFAOYSA-N
분자식
C24H54OSn2
평균 분자량
596.1 g/mol
단동위원소 질량
598.22185575

개요

Bis(tributyltin) oxide appears as clear pale yellow liquid. Toxic by skin absorption or inhalation of vapors. Used as a bactericide, fungicide and chemical intermediate.

이름 및 식별자

우선 이름
Bis(tributyltin) oxide
IUPAC
tributyl(tributylstannyloxy)stannane
현지명
비스(트리노르말부틸틴)옥사이드
영어명
Bis(tributyltin) oxide
분자식
C24H54OSn2
분자량
596.1

이름 및 동의어

Tributyltin oxide56-35-9BIS(TRIBUTYLTIN) OXIDEBis(tributyltin)oxideHexabutyldistannoxaneButinoxDistannoxane, hexabutyl-Bis(tri-n-butyltin) oxideStannicide ALastanox QLastanox TBiomet TBTO
이름 더 보기
비스(트리노르말부틸틴)옥사이드비스-트라이-n-뷰틸주석산화물트라이부틸틴옥사이드비스(트라이부틸틴)옥사이드비스(트라이뷰틸주석) 옥사이드1,1,1,3,3,3-헥사뷰틸다이스탄녹세인5,5,7,7-테트라뷰틸-6-옥사-5,7-다이스탄나운데케인산화 비스(트라이뷰틸)주석산화 비스(트라이뷰틸주석)산화 비스-n-트라이뷰틸주석산화 트라이-n-뷰틸주석산화 트라이뷰틸주석옥시비스트라이뷰틸스탄네인트리부틸주석산화물헥사뷰틸다이스탄녹세인TBOTTBTOHBDBTO1,1,1,3,3,3-HexabutyldistannoxaneBis(tributyloxide) of tinOTBEdrall
Mykolastanox FBiomet 66Lastanox FBis(tri-n-butyltin)oxideBioMeT SRMOxybis(tributylstannane)Bis(tributylstannyl)oxideLastanox T 20

데이터베이스 식별자

CAS
56-35-9、813-19-4
PubChem CID
16682746
DTXSID
DTXSID9020166
ChEBI
CHEBI:81543
UNII
3353Q84MKM
EC Number
200-268-0
Nikkaji
J4.568C

물성

구조 계산 물성

극성 표면적
9.2 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
1
회전 가능 결합 수
20
무거운 원자 수
27

실험 및 물리화학적 성질

Chemical Classes · 2건

Metals -> Tin Compounds, Organic

Teratogens

Pesticides · 3건

Pesticide -> EPA IRIS

Fungicides

Active substance -> EU Pesticides database: Not approved

LogP · 2건

log Kow= 3.84

3.84

OdorWeak odor
Density · 3건

1.17 at 77 °F (NTP, 1992) - Denser than water; will sink

1.17 g/cu cm @ 25 °C

Relative density (water = 1): 1.17 (20 °C)

Viscosity4.8 Centistokes at 25 °C

물리화학적 성질

녹는점
-45 °C · -45°C
끓는 점
180 °C2 · 180 °C2 mm Hg(lit.)
밀도
1.17 g/mL · 1.17 g/mL at 25 °C(lit.)
증기압
0.01 mm · <0.01 mm Hg ( 25 °C)
굴절률
20 · n20/D 1.486(lit.)
인화점
230 °F · >230 °F

화학적 성질

Clear colorless liquid

안전 및 규제

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 1.1% (5 of 451) of reports.

Danger

H301 (98.9%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 451 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

유해성 정보

Regulatory Information · 6건

Chemical: Distannoxane, 1,1,1,3,3,3-hexabutyl-

Hazard Traits - Bioaccumulation; Environmental Persistence; Environmental tox

Council Regulation (EEC) No 315/1993

2002/2076

Status: Active Update: 03-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/12201

Substance: Bis(tributyltin) oxide (TBTO)

DOT LabelPoison
Fire Hazards · 2건

This chemical is probably combustible. (NTP, 1992)

Combustible.

Fire PotentialCombustible.
Health HazardsACUTE/CHRONIC HAZARDS: This material is toxic by ingestion and inhalation and is a skin and eye irritant. (NTP, 1992)
Hazards Summary · 1건

Classified as moderately toxic, some formulations are for Restricted Use. [EXTOXNET] Occupational asthma reported in venipuncture technician (phlebotomist) using needles treated with bis(tri-n-butyltin)oxide; [Malo] Tributyltin oxide is a strong skin irritant. [Kanerva, p. 1841] Skin contact may cause redness and delayed burns; Inhalation of aerosol may cause pneumonitis and pulmonary edema; [ICSC] Low acute toxicity by skin absorption with an LD50 of >9000 mg/kg for the rabbit; Causes heptocellular necrosis in rats fed 25 mg/kg for 4 weeks; Causes adverse effects to the thymus, impairing cell mediated immunity at doses as low as 5 mg/kg in rats; No convincing evidence that TBTO is mutagenic; No teratogenic effects at doses below those that cause maternal toxicity; Tumors have been seen in animal studies, but their significance is questionable; [Reference #1] Skin, eye, and respiratory tract irritation, dermatitis, headache, nausea, and vomiting have been reported in occupationally exposed individuals; [HSDB] See Tin, organic compounds.

안전 및 보호

Fire Fighting · 2건

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

In case of fire in the surroundings, use appropriate extinguishing media.

First Aid Measures · 4건

Fresh air, rest. Half-upright position. Refer for medical attention.

Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Give one or two glasses of water to drink. Refer for medical attention .

First Aid · 1건

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageWell closed. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access.
Exposure Control and Personal Protection0.02 [mg/m3], inhalable fraction, as Sn[German Research Foundation (DFG)]
Fire Fighting Procedures · 2건

Provision to contain effluent from fire extinguishing.

In case of fire in the surroundings: all extinguishing agents allowed.

독성 정보

Target OrgansImmune
Health EffectsBreathing or swallowing, or skin contact with organotins, can interfere with the way the brain and nervous system work, causing death in severe cases. Organic tin compounds may also damage the immune and reproductive system. (L307, L308)
Ecotoxicity Values · 1건

LC50 Pimephales promelas (fathead minnow) 2.7 ug/l/96 hr (confidence limit 2.4 - 3.0 mg/l), flow-through bioassay with measured concentrations, 24.0 °C, dissolved oxygen 7.5 mg/l, hardness 51.5 mg/l calcium carbonate, alkalinity 41.1 mg/l calcium carbonate, and pH 7.5.

Environmental Fate · 4건

TERRESTRIAL FATE: Bis(tributyltin) oxide will bind strongly to soil(1) and thus is expected to have low mobility in soil(SRC). Bis(tributyltin) oxide is susceptible to biodegradation in soil and has a half-life of 15-20 weeks(2). Bis(tributyltin) oxide may slowly photodegrade on the soil surface(3) but would not be expected to volatilize from near-surface soil(4,5).

AQUATIC FATE: If bis(tributyltin) oxide is released to water, it will be expected to exist mainly as the tributyltin cation(1). It may react with sulfides present in sediment, which would lead to the formation of bis(tributyltin) sulfide(2). Analysis of extracts of tributyltin cations in dissolved in seawater showed that the equilibrium mixture of speciation products is composed of tributyltin chloride, tributyltin hydroxide, the aquo complex (TBTOH2+), and a tributyltincarbonato species(3). The equilibrium distribution is a function of chloride concn, dissolved CO2, and pH(3). Tributyltin cation 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(4). No degradation of tributyltin was observed in 11 months in KCN-poisoned water sediment mixtures from an area of Toronto Harbor(5). 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(5,6). Results from experiments in water and water sediment mixtures indicate that abiotic degradation of tributyltin species will be limited to direct photolysis in surface water(4,5,7). The half-life for sunlight photolysis of tributyltin cation was determined to be >89 days both in distilled water and water from Hamilton Harbor (Toronto, Canada)(4). Based on a classification scheme(8), a Koc value of 90,800(7,9,10), indicates that bis(tributyltin) oxide is expected to adsorb to suspended solids and sediment(SRC). Based upon a BCF of >6,000(3), tributyltin can bioconcentrate strongly in various aquatic organisms(SRC). Based upon laboratory observations(4) and the fact that tributyltin cations are the dominant species in water, volatilization from water is not expected to be important(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 initially decreased in the water column at a rate of 0.20/day (half-life 3.5 days) for 15 days and then slowed to 0.10/day (half-life 6.9 days)(1). The change in removal rate corresponded to a roughly 50% decrease in chlorophyll concn(1). Most of the tributyltin was lost from the water column due to biodegradation which occurred at a rate of 0.08/day(1). A third of the tributyltin degraded directly to monobutyltin and the other two-third degraded first to dibutyltin and then to monobutyltin (about 0.04/day). There was no evidence that monobutyltin degraded in the water column(1). Some tributyltin sorbed to the sediment in which it did not measurably degrade(1). Some of the tributyltin was lost into the air(1). Of the activity added to the mesocosm, 60% had left the water column after 50 days(1). After the first two weeks about 30% of the activity was found in the sediment, after which there did not appear to be any remobilization back into the water column(1). Also after the first two weeks, the activity in the water column did not change except for the loss of CO2 to the atmosphere(1). Tributyltin incorporated into the sediment degraded very slowly or not at all; degradation rates were <0.0001/day(1). About 30% of the activity left the water column within 7 days(1). Only 0.9% of the activity loss could be accounted for by adsorption to the walls(1). The loss of tributyltin from the water column to the air is much more rapid than can be ascribed to normal volatilization(1). In this case it was noted that there was a rapid transfer into the surface microlayer, from which loss occurred either by direct volatilization through prior photodegradation(1). Tributyltin compounds in seawater are degraded in summer to give dibutyltins, hydroxylated tributyltins, hydroxylated dibutyltins, carboxylated derivatives and monobutyltin(2). These compounds were formed, if at all, in limited quantities in the other seasons(2). The ratio of these organotins in oysters collected in the same area showed similar values indicating that microbial degradation may be an important degradation pathway for tributyltins(2). Monitoring studies indicate that tributyltin is very persistent in anoxic sediment from the marine environment(3). The same is true, although to a lesser extent for triphenyl tin. 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). Desorption from sediment is low(3).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bis(tributyltin) oxide, which has an estimated vapor pressure of 7.8X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase bis(tributyltin) oxide 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 1.5 hours(SRC), calculated from its rate constant of 85X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Particulate-phase bis(tributyltin) oxide may be removed from the air by wet and dry deposition(SRC). There are no experimental studies relating to bis(tributyltin) oxide's photodegradation in air(SRC). However, tributyltin species present in water solutions has been observed to slowly photodegrade in sunlight(4).

Food Survey Values · 1건

In a survey of Canadian wines from 3 provinces, tributyltin levels were much lower than either mono or dibutyltin with levels of <0.1-1.9 ng/ml. The sources of butyltin residues appeared to be the use of non-food grade PVC as liners in transport tanks(1).

Adverse EffectsNeurotoxin - Other CNS neurotoxin

규제 정보

FDA RequirementsBis(tri-n-butyltin) oxide is an indirect food additive for use as a preservative only as a component of adhesives.
FIFRA Requirements · 1건

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Bis(tributyltin) oxide is found on List B. Case No: 2620; Pesticide type: Fungicide, biocide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Bis(tributyltin) oxide; Data Call-in (DCI) Date(s): 03/30/91, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

State Drinking Water Guidelines(FL) FLORIDA 4.4 ug/L

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
JN8750000
ridadr
UN 2788 6.1/PG 2
독성
LD50 oral in rat: 87mg/kg
HS 번호
29310095

화학 및 산업

약리 정보

Biological Half-LifeThe calculated half-time for elimination of TBTO residues in mice is 29 days.
Metabolism/Metabolites · 4건

The GI tract is a major route by which humans are exposed to environmental chemicals. We have examined in these studies the effects of oral admin of organotin cmpds in the small intestinal epithelium, an organ which exhibits highly active drug & other chemical metab. A series of n-butyltin cmpds was admin by gavage to male Sprague-Dawley rats (225-275g) in single doses up to to 250 umol/kg bw. Bis(tri-n-butyltin)oxide produced dose & time dependent decr in the content & functional activity of intestinal cytochrome p450, together with an elevation (3-fold) in the activity of microsomal heme oxygenase. The effects of di-n-butyltin dichloride on heme oxygenase & cytochrome p450 were pronounced in the small intestine & extended to the liver & kidneys within 21hr after oral exposure, whereas bis(tri-n-butyltin)oxide did not affect the liver until much later (6 days), when cytochrome p450 content was reduced markedly (30%). Furthermore, the effects produced by tetra-n-butyltin on cytochrome p450 at 24hr were localized in the intestinal epithelium. These studies indicate important pharmacological effects of organotin cmpd in the gut, & raise the possibility that concurrent oral ingestion of organotins with other environmental pollutants may alter the cytochrome p450 dependent metab of xenobiotics & natural substrates of this monooxygenase system in the small intestine.

Metab in mammals is rapid; metabolites are detectable in the blood within 3hr of TBTO admin. The principal metabolite appears to be the hydroxybutyl cmpd, which is unstable & rapidly splits to form the dibutyl derivative & butanol. In in vitro studies, it has been shown that TBTO is a substrate for mixed-function oxidases, but these enzymes are inhibited by very high concn of TBTO.

Tributyltin metab also occurs in lower organisms, but it is slower, particularly in mollusks, than in mammals. The capacity for bioaccumulation is, therefore, much greater in lower organisms than in mammals. /Tributyl tin/

Though tin metal is very poorly absorbed, tin compounds may be absorbed via oral, inhalation, or dermal routes, with organotin compounds being much more readily absorbed than inorganic tin compounds. Tin may enter the bloodstream and bind to hemoglobin, where it is distributed and accumulates mainly in the kidney, liver, lung, and bone. Organotin compounds may undergo dealkylation, hydroxylation, dearylation, and oxidation catalyzed by cytochrome P-450 enzymes in the liver. The alkyl products of dealkylation are conjugated with glutathione and further metabolized to mercapturic acid derivatives. Tin and its metabolites are excreted mainly in the urine and feces. (L308)

MeSH Pharmacological Classification · 3건

Substances used on inanimate objects that destroy harmful microorganisms or inhibit their activity. Disinfectants are classed as complete, destroying SPORES as well as vegetative forms of microorganisms, or incomplete, destroying only vegetative forms of the organisms. They are distinguished from ANTISEPTICS, which are local anti-infective agents used on humans and other animals. (From Hawley&apos;s Condensed Chemical Dictionary, 11th ed)

Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.

Absorption, Distribution and Excretion · 2건

The calculated half-time for elimination of TBTO residues in mice is 29 days.

TBTO is absorbed from the gut (20-50%, depending on the vehicle) & via the skin of mammals (approx 10%). Other data suggest absorption in the 1-5% range via the skin. TBTO can be transferred across the blood-brain barrier & from the placenta to the fetus. ... Absorbed material is rapidly & widely distributed among tissues (principally the liver and kidney). ... The rate of TBTO loss differs with different tissues. TBTO & its metabolites are eliminated principally via the bile.

용도 및 제조

Uses · 6건

Used as antimicrobial and slimicide for cooling-water treatment, disinfectant for hard-surface, sanitizer for laundry, mildewcides in water-based emulsion paints, preservative for timber, millwork, wood, textiles, paper, leather, and glass, and as fungicide and bactericide in underwater and antifouling paints; Also used as pesticide, molluscicide, rodent repellant, and insecticide; [HSDB] Used as a bactericide, fungicide, and chemical intermediate; [CAMEO] Used as fungicide, disinfectant, algicide, microbiocide, and microbiostat for cooling tower water, wood preservation (paints, stains, and waterproofing formulations), hard surfaces (livestock, veterinary, and other animal facilities), building materials (drywall, joint compound MDF board, and particulate board), building material adhesives, and adhesives for other manufacturing applications; Also used to treat textile fabrics (except laundry and clothing), paper, fiberfill, foam, rope, sponges, and other materials; Tributyltin products are also used in petrochemical injection fluids, metal working fluids, irrigation tubing for non-agricultural uses, rubber for sonar domes, and instruments for oceanographic observations; [EPA RED]

Tributyltin compounds are regulated by the EPA under the Organotin Antifouling Paint Control Act of 1988; Registration cancelled in 2005 for tributyltin ship hull coatings; International ban effective as of September 2008; [Reference #2]

Pulp and Paper Processing [Category: Industry]

For Bis(tributyltin) oxide (USEPA/OPP Pesticide Code: 083001) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Antimicrobials and slimicides for cooling-water treatment and as hard-surface disinfectants. Also laundry sanitizers and mildewcides to prevent mildew formation in the dried film of water-based emulsion paints.

Widely used in Europe for the preservation of timber, millwork, and wood joinery, e.g., window sashes and door frames.

Methods of ManufacturingHydrolysis of tributyl tin chloride.
Formulations/PreparationsUSEPA/OPP Pesticide Code 083001; Trade Names: Self polishing copolymer, TBTO, Biomet, Biomet 75, AW 75-D, Butinox, Bio-met TBTO, Bis(tri-N-butyltin)oxide, BTO, SN-9, ENT 24,979, L.S. 3394.
Household ProductsInformation on 14 consumer products that contain bis(Tributyltin) oxide in the following categories is provided:
General Manufacturing Information · 3건

Distannoxane, 1,1,1,3,3,3-hexabutyl-: ACTIVE

Tributyltin antifouling paint can be classified into three chemical groups based on the way the tributyltin is incorporated into the paint coating and subsequently released. The first group includes paints in which the tributyltin active ingredient is mixed into the paint matrix and the tributyltin ion is released from the paint by diffusion. These are called free association paints. The second group has the tributyltin moiety chemically bound to the paint matrix. These paints are called copolymer paints and under slightly alkaline conditions (such as sea water), the tributyltin ion is released by chemical hydrolysis. Because the paint surface is softened by the loss of the tributyltin moiety, the outer layer is exposed. A third category, tributyltin ablative paints, have characteristics of both groups. The tributyltin active ingredient is mixed into the paint matrix, but because these are relatively soft paints, the surface ablates or sloughs off as the painted vessel moves through the water.

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.

응용 분야 · 3건

개요TBTO (bis(tri-n-butyltin)oxide) appears as thin, colourless to pale yellow, flammable and combustible liquid. It is soluble in organic solvents. TBTO, or bis(tri-n-butyltin)oxide, is an organotin compound used as a biocide, fungicide, and molluscicide. Uses of tributyltin also include as an anti-fouling chemical in marine paints for boats, anti-fungal agent in textiles and industrial water systems, in cooling tower and refrigeration water systems, wood pulp preservative in paints and paper mill systems, inner surfaces of cardboard, and in the manufacturing processes of leather goods, textiles, wood, plastics, and mothproof stored garments. In fact, TBT compounds are considered the most hazardous of all tin compounds.

용도Bis(tributyltin) Oxide is an organotin compound used as a fungicide and molluscicide, particularly in wood preservation. Bis(tributyltin) Oxide was used as an active component in marine antifouling paints but is not longer used due to its toxicity and is considered a severe marine pollutant.

일반 설명Clear pale yellow liquid. Toxic by skin absorption or inhalation of vapors. Used as a bactericide, fungicide and chemical intermediate.

공급사103 곳

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