Chemistry:Dibutyltin dilaurate

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Dibutyltin dilaurate
Dibutyltin dilaurate molecule structure
Names
IUPAC name
[Dibutyl(dodecanoyloxy)stannyl] dodecanoate
Other names
  • Butynorate
  • Davainex[1]
  • DBTDL
  • DBTL[1]
  • Dibutylbis(lauroyloxy)tin[1]
  • Dibutylstannylene dilaurate[1]
  • Dibutyltin didodecanoate[1]
  • Dibutyltindilaurate
  • Lauric acid, 1,1'-(dibutylstannylene) ester[1]
  • Stabilizer D-22[1]
  • T 12 (catalyst)[1]
  • Tinostat[1]
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 201-039-8
RTECS number
  • WH7000000
UNII
UN number 3146
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]
1.4683 at 20 °C (for light at wavelength of 589.29 nm)[1]
Viscosity 42 cP[1]
Hazards
GHS pictograms GHS07: HarmfulGHS08: Health hazardGHS09: Environmental hazard
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):
  • 175 mg/kg (oral, rat)
  • 33 mg/kg (intravenous, rat)
  • 210 mg/kg (oral, mouse)
  • 100 mg/kg (oral, rabbit)
[1]
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. ↑ 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. ↑ 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. 
  3. ↑ 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. 
  4. ↑ Davies, Alwyn George (2004). Organotin chemistry (2nd ed.). Weinheim: Wiley-VCH. Applications, Environmental Issues, and Analysis. ISBN 3-527-31023-1. 
  5. ↑ PubChem. "Butynorate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/16682738. 



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