Dibutylzinndilaurat

Dibutyltin dilaurate

HCID 16682738

Grundinformationen

CAS
77-58-7
Standard-SMILES
CCCCCCCCCCCC(=O)[O][Sn]([CH2]CCC)([CH2]CCC)[O]C(=O)CCCCCCCCCCC
InChIKey
UKLDJPRMSDWDSL-UHFFFAOYSA-L
Summenformel
C32H64O4Sn
Durchschnittliche Molmasse
631,6 g/mol
Monoisotopische Masse
632,38265523

Überblick

Dibutyltin dilaurate is a clear yellow viscous liquid. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
Dibutyltin dilaurate
IUPAC
[dibutyl(dodecanoyloxy)stannyl] dodecanoate
Lokaler Name
Dibutylzinndilaurat
Englischer Name
Dibutyltin dilaurate
Summenformel
C32H64O4Sn
Molmasse
631.56

Namen und Synonyme

Dibutyltin dilaurate77-58-7ButynorateDavainexTinostatDi-n-butyltin dilaurateStanclere DBTLDibutyltin laurateStabilizer D-22Dibutylbis(lauroyloxy)tinTVS Tin LauDBTL
Weitere Namen anzeigen
DBTDLt12tn12Dibutyltin dillaurateDI-N-BUTYLDILAURYLTIN
T 12 (catalyst)Dibutylbis(laurato)tinOngrostab BLTMDibutyltin didodecanoateStavinor 1200 SNDibutyltin n-dodecanoateThermolite T 12Dibutylstannylene dilaurate

Datenbank-Bezeichner

CAS
77-58-7
PubChem CID
16682738
DTXSID
DTXSID6024961
EC Number
201-039-8

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
52,6 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
30
Schwere Atome
37

Experimentelle und physikochemische Eigenschaften

Chemical ClassesMetals -> Tin Compounds, Organic
Polymers · 2 Einträge

Plastics -> Heat stabilisers

Plastics -> Polyolefin-I; PVC (soft); PVC (rigid)

LogP · 2 Einträge

log Kow= 3.12

4.44

Density · 4 Einträge

1.066 at 68 °F (NTP, 1992) - Denser than water; will sink

1.05 g/cu cm @ 20 °C

Density (at 20 °C): 1.05 g/cm³

1.06 @ 20°C

Viscosity42 cP at 25 °C
Color/Form · 2 Einträge

Soft crystals or yellow liquid

Oily liquid

Physikochemische Eigenschaften

Schmelzpunkt
22 · 22-24°C
Siedepunkt
204 °C/12mm · >204°C/12mm
Dichte
1.066 g/mL · 1.066 g/mL at 25 °C(lit.)
Dampfdruck
0.2 mm · 0.2 mm Hg ( 160 °C)
Brechungsindex
20 · n20/D 1.471(lit.)
Flammpunkt
230 °F · >230 °F

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]

P203, P260, P264, P270, P280, P318, P319, P405, and P501 (click each P-code to see the statement)

Warning

H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: Stannane, dibutylbis[(1-oxododecyl)oxy]-

Hazard Traits - Reproductive Toxicity

Dodecanoic acid, 1,1'-(dibutylstannylene) ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Dodecanoic acid, 1,1'-(dibutylstannylene) ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 28-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14904

Dibutyltin dilaurate: HSNO Approval: HSR003610 Approved with controls

Other Safety InformationIMAP assessments - Stannane, dibutylbis[(1-oxododecyl)oxy]-: Human health tier II assessment
DOT LabelPoison
Fire Hazards · 2 Einträge

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialCombustible when exposed to heat or flame; reacts with oxidizers.
Health HazardsSYMPTOMS: Symptoms associated with this compound include primary skin irritation, nausea, headache, muscular weakness and paralysis.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fires involving this compound should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4 Einträge

Fresh air, rest.

Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse and then wash skin with water and soap.

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

Rinse mouth.

First Aid · 1 Eintrag

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 StorageStore in an area without drain or sewer access.
Exposure Control and Personal Protection0.02 [mg/m3], inhalable fraction, as Sn[German Research Foundation (DFG)]
Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Toxikologische Informationen

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)
Environmental Fate · 4 Einträge

The final degradation products of organotins are believed to consist of inorganic salts. /Organotin compounds/

TERRESTRIAL FATE: Dibutyltin dilaurate is expected to dissociate in soil forming the cation, dibutyltin(SRC). Dibutyltin is expected to adsorb to organic carbon and clay(SRC). Volatilization from moist soil surfaces is not expected to be an important fate process because the cation is not expected to volatilize(SRC). Dibutyltin dilaurate may also biodegrade in soil, since tributyltins are converted to dibutyltin and monobutyltin(1).

AQUATIC FATE: Dibutyltin dilaurate is expected to dissociate in water forming the cation, dibutyltin(SRC). Cations generally adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected to be an important fate process because the cation is not expected to volatilize(SRC). Dibutyltin dilaurate may also biodegrade in soil(1). According to a classification scheme(2), a BCF value of 31(3) suggests the potential for bioconcentration in aquatic organisms is low(SRC). Tributyltin species in water are sequentially degraded to dibutyltin, monobutyltin, and finally to inorganic tin in water/sediment mixtures or water alone from Toronto Harbor, Canada(4). Small quantities of dimethyldibutyltin were occasionally detected in these experiments in water/sediment and water alone, but not in the sterile controls, which indicates the possibility of biomethylation of dibutyltin compounds(4).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dibutyltin dilaurate, which has an estimated vapor pressure of 4.5X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase dibutyltin dilaurate may be removed from the air by wet and dry deposition(SRC).

Food Survey ValuesIn a survey of Canadian wines from 3 provinces, dibutyltin was the predominant butyltin present, with 23.2% of samples tested containing 1.1-138.1 ng/ml. The source of butyltin was not reported(1).
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure Routes · 2 Einträge

The substance can be absorbed into the body by ingestion and through the skin.

Oral (L308) ; inhalation (L308) ; dermal (L308)

Toxicity Summary · 1 Eintrag

Organotin compounds produce neurotoxic and immunotoxic effects. Organotins may directly activate glial cells contributing to neuronal cell degeneration by local release of pro-inflammatory cytokines, tumor necrosis factor-_, and/or interleukins. They may also induce apoptosis by direct action on neuronal cells. Organotin compounds stimulate the neuronal release of and/or decrease of neuronal cell uptake of neurotransmitters in brain tissue, including aspartate, GABA, glutamate, norepinephrine, and serotonin. This may be either a contributing factor to or result of the neuronal cell loss. The immunotoxic effects of organotins are characterized by thymic atrophy caused by the suppression of proliferation of immature thymocytes and apoptosis of mature thymocytes. Organotin compounds are believed to exert these effects by suppressing DNA and protein synthesis, inducing the expression of genes involved in apoptosis (such as nur77), and disrupting the regulation of intracellular calcium levels, giving rise to the uncontrolled production of reactive oxygen species, release of cytochrome c to the cytosol, and the proteolytic and nucleolytic cascade of apoptosis. The suppression of proliferation of immature thymocytes further results in the suppression of T-cell-mediated immune responses. Organotins are also endocrine disruptors and are believed to contribute to obesity by inappropriate receptor activation, leading to adipocyte differentiation. Inorganic tin triggers eryptosis, contributing to tin-induced anemia. (L308, A182, A184)

Regulatorische Informationen

FDA RequirementsDibutyltin dilaurate is an indirect food additive for use only as a catalyst for polyurethane resins as a component of adhesives.
TSCA Requirements · 1 Eintrag

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Dibutyltin dilaurate is included on this list.

FIFRA Requirements · 1 Eintrag

Dibutyltin dilaurate is exempted from the requirement of a tolerance when used as a component of plastic slow release tag in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals.

State Drinking Water Guidelines(MN) MINNESOTA 4000 ug/l /Tin/

Sicherheitsdaten

F
10-21
wgk
3
tsca
TSCA listed
ridadr
UN 2922 8/PG 3
hs_code
29319090
RTECS-Nr.
WH7000000

Chemie und Industrie

Pharmakologische Informationen

ATC CodeQP - Antiparasitic products, insecticides and repellents
Mechanism of Action · 1 Eintrag

... Rats fed dibutyltin dilaurate at a dose of 17.5 mg/kg per day for 15 days by oral intubation exhibited a 15% stimulation of heme oxygenase activity and a decreased hepatocellular cytochrome p450 content. These effects were accompanied by a decrease in the specific activities of several microsomal enzymes. In addition, pentobarbital-induced sleeping time was increased in proportion to the duration of the dibutyltin exposure, demonstrating the impairment of barbiturate metabolism in the dibutyltin-treated animals.

Metabolism/Metabolites · 1 Eintrag

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)

Verwendung und Herstellung

Uses · 6 Einträge

Used as a stabilizer (polyvinyl chloride resins, vinyl resins, lacquers, and elastomers), a catalyst for urethane and silicones, and a drug (anthelmintic and coccidiostat); [HSDB]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

Stabilizer for polyvinyl chloride resins. Catalyst for curing certain silicones.

Stabilizer for vinyl resins, lacquers, elastomers; catalyst for urethane and silicones.

In the United States, dibutyltin compounds are used mostly in the catalysis of rigid foams and the laurate has been the catalyst of choice.

Catalyst for the curing of room-temperature-vulcanized (RTV) silicone elastomers to produce flexible silicone rubbers used as sealing compounds, insulators, and in a wide variety of other applications.

U.S. Production2023: 1,000,000 - <2,500,000 lb
Consumer UsesStabilizing agent
Industry UsesFoamant
Methods of ManufacturingPrepn: Shervedina et al. Khim. Prom. 1962 (10), 107, Chemical Abstracts 59, 8776f (1963), Fr. pat. 1,320,473 (1963 to Noury and van der Lande)
Household ProductsInformation on 2 consumer products that contain Dibutyltin dilaurate in the following categories is provided:
Anwendungen · 1 Eintrag

VerwendenDibutyltin dilaurate has been used as a catalyst in a protocol for the covalent attachment of poly(ethylene glycol) (PEG) to silicon oxide to form a hydrophilic non-fouling surface. It can also be used as a catalyst in the preparation of polymers by reacting hydroxyl-terminated macromonomers and aliphatic diisocyanates.

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