Dibutyltin dilaurate
[CAS# 77-58-7]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organotin
• Name: Dibutyltin dilaurate
• Synonyms: Bis(lauroyloxy)di(n-butyl)stannane
• Molecular Formula: C₃₂H₆₄O₄Sn
• Molecular Weight: 631.55
• CAS Registry Number: 77-58-7
• EC Number: 201-039-8
• SMILES: CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC

Properties

• Melting point: 22-24 °C
• Index of Refraction: 1.471
• Flash point: 113 °C
• Solubility: <0.1 g/100 mL (water, 20 °C), soluble (benzene, ether)

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS08 Danger
• Risk Statements: H314-H330-H341-H360FD-H372
• Safety Statements: P203-P260-P264-P270-P271-P280-P284-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P318-P319-P320-P321-P363-P403+P233-P405-P501
• Transport Information: UN 2922

Discovery and Applications

Dibutyltin dilaurate (DBTL) is an organotin compound widely recognized for its catalytic properties, particularly in the field of polymer chemistry. Its molecular formula is C22H44O4Sn, and it consists of a dibutyltin moiety combined with two laurate groups derived from lauric acid. The discovery of dibutyltin dilaurate can be traced back to the study of organotin compounds in the mid-20th century. Researchers were exploring the properties and applications of organotin compounds, leading to the synthesis of various derivatives. DBTL gained attention for its efficiency as a catalyst, particularly in the polymerization of polyurethanes and silicones.

One of the primary applications of dibutyltin dilaurate is as a catalyst in the production of polyurethanes. In the polyurethane industry, DBTL facilitates the reaction between polyols and isocyanates, promoting the formation of urethane linkages. Its effectiveness as a catalyst is attributed to its ability to accelerate the reaction rates, resulting in shorter processing times and improved product quality. This application has made dibutyltin dilaurate a critical component in the manufacture of flexible and rigid polyurethane foams, coatings, adhesives, and elastomers.

In addition to its use in polyurethane synthesis, dibutyltin dilaurate is also employed in the production of silicone materials. It acts as a catalyst in the curing of silicone rubbers, enhancing the cross-linking process and ultimately improving the mechanical properties of the final product. The versatility of DBTL in catalyzing various polymerization reactions has established it as a valuable additive in the polymer industry.

Dibutyltin dilaurate has found applications in other areas, including the formulation of antifouling paints and coatings. Its biocidal properties make it effective in preventing the growth of marine organisms on ship hulls and underwater structures. This application is particularly important in maritime industries, where the fouling of surfaces can lead to reduced efficiency and increased fuel consumption.

Despite its widespread utility, safety concerns regarding dibutyltin dilaurate must be considered. Organotin compounds, including DBTL, have been scrutinized for their potential toxicity and environmental impact. Studies have indicated that exposure to dibutyltin compounds can pose health risks, including reproductive and developmental effects. Therefore, proper handling and safety measures should be observed when working with dibutyltin dilaurate in industrial settings.

In summary, dibutyltin dilaurate is a significant organotin compound with a rich history of discovery and diverse applications in the polymer industry. Its catalytic properties facilitate the production of polyurethanes and silicones, while its biocidal effects make it useful in antifouling coatings. As industries continue to utilize this compound, ongoing research into its safety and environmental impact will be essential to ensure responsible use.

References

2003. In vitro trypanocidal activity of dibutyltin dichloride and its fatty acid derivatives. Parasitology Research, 91(3).
DOI: 10.1007/s00436-003-0861-2

2020. Characterization of antimicrobial effect of organotin-based catalysts on diesel-biodiesel deteriogenic microorganisms. Environmental Monitoring and Assessment, 192(12).
DOI: 10.1007/s10661-020-08744-x

2008. Sustained release of antibiotic from polyurethane coated implant materials. Journal of Materials Science: Materials in Medicine, 19(10).
DOI: 10.1007/s10856-008-3521-3