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
  • 77-58-7 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 21106564
ECHA InfoCard 100.000.946 Edit this at Wikidata
EC Number
  • 201-039-8
PubChem CID
  • 16682738
RTECS number
  • WH7000000
UNII
  • L4061GMT90 checkY
UN number 3146
CompTox Dashboard (EPA)
  • DTXSID301014847 DTXSID6024961, DTXSID301014847 Edit this at Wikidata
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
  • 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]
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:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
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
Chemical compound

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

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 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 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.