Chemistry:Dibutyltin dilaurate
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| Names | |
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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 | |
| EC Number |
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PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 3146 |
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| Properties | |
| (CH 3(CH 2) 10CO 2) 2Sn((CH 2) 3CH 3) 2 | |
| Molar mass | 631.570 g·mol−1 |
| Appearance | Colourless oily liquid or soft waxy crystals |
| Odor | Fatty[2] |
| Density | 1.066 g/cm3 |
| 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 (less than 1 mg/mL at 68 °F (20 °C))[1] | |
| 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 160 °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 | |
| GHS pictograms |   
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| GHS Signal word | Danger |
| HH341Script error: No such module "Preview warning".Category:GHS errors, HH360FDScript error: No such module "Preview warning".Category:GHS errors, HH372Script error: No such module "Preview warning".Category:GHS errors[1] | |
| PP260Script error: No such module "Preview warning".Category:GHS errors, PP264Script error: No such module "Preview warning".Category:GHS errors, PP270Script error: No such module "Preview warning".Category:GHS errors, PP280Script error: No such module "Preview warning".Category:GHS errors, PP281Script error: No such module "Preview warning".Category:GHS errors, PP319Script error: No such module "Preview warning".Category:GHS errors, PP405Script error: No such module "Preview warning".Category:GHS errors, PP501Script error: No such module "Preview warning".Category:GHS errors[1] | |
| 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). | |
| Infobox references | |
Dibutyltin dilaurate (abbreviated DBTDL) is an organotin compound with the formula (CH
3(CH
2)
10CO
2)
2Sn((CH
2)
3CH
3)
2. It is a colorless viscous and oily liquid. It is used as a catalyst .
Description
In 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]
Decomposition
Upon heating to decomposition temperature (which is above 250 °C[2]), dibutyltin dilaurate emits acrid smoke and fumes.[1]
Uses
Dibutyltin 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,[4][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.[5]
Hazards and toxicity
Dibutyltin 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
- Dibutyltin dioctanoate: CAS#4731-77-5
- Dibutyltin diacetate: CAS #1067-33-0
References
- ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 1.12 1.13 1.14 1.15 1.16 1.17 1.18 1.19 1.20 1.21 1.22 1.23 1.24 1.25 "Dibutyltin dilaurate". https://pubchem.ncbi.nlm.nih.gov/compound/Dibutyltin-dilaurate.
- ↑ 2.0 2.1 2.2 2.3 2.4 "Dibutyltin dilaurate 95 77-58-7". https://www.sigmaaldrich.com/HR/en/product/aldrich/291234.
- ↑ 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" (in en). Journal of Organometallic Chemistry 393 (2): 201–204. doi:10.1016/0022-328X(90)80199-A. ISSN 0022-328X.
- ↑ Davies, Alwyn George (2004). Organotin chemistry (2nd ed.). Weinheim: Wiley-VCH. Applications, Environmental Issues, and Analysis. ISBN 3-527-31023-1.
- ↑ PubChem. "Butynorate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/16682738.
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