Dibutyltin dilaurate (abbreviated DBTDL) is an organotin compound with the formula (CH3(CH2)10CO2)2Sn(CH2CH2CH2CH3)2. It is a colorless viscous and oily liquid. It is used as a catalyst .
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IUPAC name
[Dibutyl(dodecanoyloxy)stannyl] dodecanoate
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Other names | |
Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.000.946 |
EC Number |
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PubChem CID
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RTECS number |
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UNII | |
UN number | 3146 |
CompTox Dashboard (EPA)
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Properties | |
(CH3(CH2)10CO2)2Sn((CH2)3CH3)2 | |
Molar mass | 631.570 g·mol−1 |
Appearance | Colourless oily liquid or soft waxy crystals |
Odor | Fatty[2] |
Density | 1.066 g/cm3[2] |
Melting point | 22 to 24 °C (72 to 75 °F; 295 to 297 K) [1] |
Boiling point | 205 °C at 1.3 kPa[1][2] |
Practically insoluble (0.00143 g/l at 68 °F (20 °C))[1][2] | |
Solubility | Practically insoluble in methanol Soluble in petroleum ether, benzene, acetone, ether, carbon tetrachloride, organic esters |
Vapor pressure | <0.01 hPa (0.2 mmHg at 25 °C)[2] |
Refractive index (nD)
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1.4683 at 20 °C (for light at wavelength of 589.29 nm)[1] |
Viscosity | 42 cP[1] |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Very toxic, very flammable, causes serious injuries to skin, eyes, thymus, lungs and other organs. Can cause paralysis. |
GHS labelling: | |
Danger | |
H317, H319, H341, H360, H360FD, H370, H372, H410[1][2] | |
P201, P202, P260, P264, P270, P272, P273, P280, P281, P302+P352, P305+P351+P338, P307+P311, P319, P333+P313, P337+P313, P363, P391, P405, P501[1][2] | |
Flash point | 191 °C[1] |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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LC50 (median concentration)
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150 mg/m3 (inhalation, mouse, 2 hours)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Description
editIn terms of its structure, the molecule of dibutyltin dilaurate consists of two laurate groups and two butyl groups attached to a tin(IV) atom. The molecular geometry at tin is tetrahedral. Based on the crystal structure of the related bis(bromobenzoate), the oxygen atoms of the carbonyl groups are weakly bonded to tin atom.[3] According to some authors, this compound is a dibutyltin(IV) ester of lauric acid.[1][4]
Decomposition
editUpon heating to decomposition temperature (which is above 250 °C[2]), dibutyltin dilaurate emits acrid smoke and fumes.[1]
Uses
editDibutyltin dilaurate is used as a paint additive.[1] Together with dibutyltin dioctanoate, dibutyltin dilaurate is used as a catalyst for polyurethane production from isocyanates and diols. It is also useful as a catalyst for transesterification and for the room temperature vulcanization of silicones. It is also used as a stabilizer in polyvinyl chloride,[5][1] vinyl ester resins, lacquers, and elastomers.[1] It is also added to animal feed to remove cecal worms, roundworms, and tapeworms in chickens and turkeys and to prevent or provide treatment against hexamitosis and coccidiosis.[6]
Hazards and toxicity
editDibutyltin dilaurate can be absorbed through the skin. It irritates skin and eyes (causes redness of skin and eyes). It is a neurotoxin. It can cause injuries to the liver, kidneys, and gastrointestinal tract. The symptoms of poisoning with dibutyltin dilaurate include nausea, headache, muscular weakness and even paralysis. Dibutyltin dilaurate is combustible.[1] Its vapor is denser than air (21.8 times denser than air[1]), so it can spread on the floors, forming explosive mixtures with air. On fire, it emits irritating and toxic fumes and smoke which contain tin, tin oxides and carbon oxides.[2] Dibutyltin dilaurate is very reactive with acids and oxidizers.[1]
Related compounds
edit- Dibutyltin dioctanoate (CH3(CH2)6CO2)2Sn(CH2CH2CH2CH3)2: CAS#4731-77-5
- Dibutyltin diacetate (CH3CO2)2Sn(CH2CH2CH2CH3)2: CAS #1067-33-0
References
edit- ^ a b c d e f g h i j k l m n o p q r s t u v w x y z aa "Dibutyltin dilaurate". pubchem.ncbi.nlm.nih.gov.
- ^ a b c d e f g h i https://www.sigmaaldrich.com/US/en/sds/aldrich/291234?userType=anonymous
- ^ Weng Ng, Seik; Das, V. G. Kumar; Yip, Wai-Hing; Wang, Ru-Ji; Mak, Thomas C. W. (1990-08-28). "Di-n-butyltin(IV) di-o-bromobenzoate, a weakly-bridged dimer". Journal of Organometallic Chemistry. 393 (2): 201–204. doi:10.1016/0022-328X(90)80199-A. ISSN 0022-328X.
- ^ "Trimethyltin acetate | C5H12O2Sn | ChemSpider".
- ^ Davies, Alwyn George (2004). Organotin chemistry (2nd ed.). Weinheim: Wiley-VCH. Applications, Environmental Issues, and Analysis. ISBN 3-527-31023-1.
- ^ PubChem. "Butynorate". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-08-23.