Dibutyltin dilaurate

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 .

Dibutyltin dilaurate
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
ECHA InfoCard 100.000.946
EC Number
  • 201-039-8
RTECS number
  • WH7000000
UNII
UN number 3146
  • InChI=1S/2C12H24O2.2C4H9.Sn/c2*1-2-3-4-5-6-7-8-9-10-11-12(13)14;2*1-3-4-2;/h2*2-11H2,1H3,(H,13,14);2*1,3-4H2,2H3;/q;;;;+2/p-2
    Key: UKLDJPRMSDWDSL-UHFFFAOYSA-L
  • InChI=1/2C12H24O2.2C4H9.Sn/c2*1-2-3-4-5-6-7-8-9-10-11-12(13)14;2*1-3-4-2;/h2*2-11H2,1H3,(H,13,14);2*1,3-4H2,2H3;/q;;;;+2/p-2/rC32H64O4Sn/c1-5-9-13-15-17-19-21-23-25-27-31(33)35-37(29-11-7-3,30-12-8-4)36-32(34)28-26-24-22-20-18-16-14-10-6-2/h5-30H2,1-4H3
    Key: UKLDJPRMSDWDSL-PFKFAYPQAT
  • CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC
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]
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
 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):
  • 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

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] According to some authors, this compound is a dibutyltin(IV) ester of lauric acid.[1][4]

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,[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

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]

References
  1. "Dibutyltin dilaurate". pubchem.ncbi.nlm.nih.gov.
  2. https://www.sigmaaldrich.com/US/en/sds/aldrich/291234?userType=anonymous
  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". Journal of Organometallic Chemistry. 393 (2): 201–204. doi:10.1016/0022-328X(90)80199-A. ISSN 0022-328X.
  4. "Trimethyltin acetate | C5H12O2Sn | ChemSpider".
  5. Davies, Alwyn George (2004). Organotin chemistry (2nd ed.). Weinheim: Wiley-VCH. Applications, Environmental Issues, and Analysis. ISBN 3-527-31023-1.
  6. PubChem. "Butynorate". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-08-23.
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