Dibutyltin dilaurate

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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.946
EC Number
  • 201-039-8
PubChem CID
RTECS number
  • WH7000000
UNII
UN number 3146
CompTox Dashboard (EPA)
InChI
  • 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
SMILES
  • CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC
Properties
Chemical formula
 (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]
Solubility in water
 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)
 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:
Pictograms
 GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word
 Danger
Hazard statements
 H317, H319, H341, H360, H360FD, H370, H372, H410[1][2]
Precautionary statements
 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)
  • 175 mg/kg (oral, rat)
  • 33 mg/kg (intravenous, rat)
  • 210 mg/kg (oral, mouse)
  • 100 mg/kg (oral, rabbit)
[1]
LC50 (median concentration)
 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 (CH3(CH2)10CO2)2Sn(CH2CH2CH2CH3)2. It is a colorless viscous and oily liquid. It is used as a catalyst.

Description

Dibutyltin dilaurate consists of two laurate groups and two butyl groups coordinated to a tin(IV) atom. The coordination geometry at the tin center 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] The 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 very reactive with acids and oxidizers, and it is combustible.[1] It emits irritating and toxic fumes and smoke when burned, which contain tin, tin oxides and carbon oxides.[2] Moreover, its vapor is much denser than air (21.8 times so[1]), so it can spread on floors, resulting in explosive conditions or asphyxiation hazards.

References

  1. ^ 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 "Dibutyltin dilaurate". pubchem.ncbi.nlm.nih.gov.
  2. ^ a b c d e f g h i "SAFETY DATA SHEET - Dibutyltin dilaurate". Sigma Aldrich. November 6, 2025. Archived from the original on May 2, 2024. Retrieved December 9, 2025.
  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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