Dibutyltin dilaurate

Dibutyltin dilaurate (abbreviated DBTDL), also called dibutyltindilaurate or butynorate, is an organotin compound that is used as a catalyst. It is a colourless oily liquid. In terms of its structure, the molecule consists of two laurate groups attached to a dibutyltin(IV) center.

Dibutyltin dilaurate
Names
Other names
Dibutyltindilaurate and butynorate
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
C32H64O4Sn
Molar mass 631.56 g/mol
Appearance Colourless liquid
Density 1.066 g/mL
Melting point 22 to 24 °C (72 to 75 °F; 295 to 297 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

The molecular geometry at tin is tetrahedral. Based on the crystal structure of the related bis(bromobenzoate), the carbonyl oxygen centers are weakly bonded to tin.[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.[2] It is also added to animal feed to remove cecal worms, roundworms, and tapeworms in turkeys to prevent hexamitosis and coccidiosis.[3]

  • Dibutyltin dioctanoate: CAS#4731-77-5
  • Dibutyltin diacetate: CAS #1067-33-0

References
  1. Weng Ng, S., Das, V. G. K., Yip, W.-H., Wang, R.-J., Mak, T. C. W., "Di-n-butyltin(IV) di-o-bromobenzoate, a weakly-bridged dimer", Journal of Organometallic Chemistry 1990, volume 393, 201-204. doi:10.1016/0022-328X(90)80199-A
  2. Applications, Environmental Issues, and Analysis in Organotin Chemistry, Second Edition. Alwyn G. Davies 2004 Wiley-VCH Verlag GmbH & Co. KGaA. ISBN 3-527-31023-1
  3. PubChem. "Butynorate". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-08-23.
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