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Dibutyltin diacetate
[CAS# 1067-33-0]

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Identification
ClassificationOrganic raw materials >> Organometallic salt
NameDibutyltin diacetate
Synonyms[acetyloxy(dibutyl)stannyl] acetate
Molecular StructureCAS # 1067-33-0, Dibutyltin diacetate
Molecular FormulaC12H24O4Sn
Molecular Weight351.02
CAS Registry Number1067-33-0
EC Number213-928-8
SMILESCCCC[Sn](CCCC)(OC(=O)C)OC(=O)C
Properties
Density1.31
Melting point7-10 °C
Index of Refraction1.471
Boiling point139 °C (5 mmHg)
Flash point143 °C
Water solubilityinsoluble
Safety Data
Hazard Symbolssymbol symbol symbol symbol   GHS05;GHS07;GHS08;GHS09 Danger  Details
Risk StatementsH314-H317-H318-H341-H360-H360FD-H370-H372-H400-H410  Details
Safety StatementsP203-P260-P261-P264-P264+P265-P270-P272-P273-P280-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P308+P316-P316-P317-P318-P319-P321-P333+P317-P362+P364-P363-P391-P405-P501  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Skin corrosionSkin Corr.1BH314
Specific target organ toxicity - repeated exposureSTOT RE1H372
Chronic hazardous to the aquatic environmentAquatic Chronic1H410
Germ cell mutagenicityMuta.2H341
Specific target organ toxicity - single exposureSTOT SE1H370
Serious eye damageEye Dam.1H318
Skin sensitizationSkin Sens.1BH317
Reproductive toxicityRepr.1BH360
Acute hazardous to the aquatic environmentAquatic Acute1H400
Reproductive toxicityRepr.1BH360FD
Skin sensitizationSkin Sens.1H317
Acute toxicityAcute Tox.4H302
Acute toxicityAcute Tox.2H300
Acute toxicityAcute Tox.3H301
Eye irritationEye Irrit.2H319
Specific target organ toxicity - single exposureSTOT SE2H371
Skin irritationSkin Irrit.2H315
Specific target organ toxicity - repeated exposureSTOT RE2H373
Reproductive toxicityRepr.1AH360
Acute toxicityAcute Tox.2H310
Chronic hazardous to the aquatic environmentAquatic Chronic2H411
Reproductive toxicityRepr.1AH360FD
Skin corrosionSkin Corr.1H314
Reproductive toxicityRepr.1BH360FD
SDSAvailable
up Discovery and Applications
Dibutyltin diacetate is an organotin compound with the molecular formula C12H22O4Sn. It features a dibutyltin group where two butyl groups are attached to a tin atom, with two acetate groups coordinating to the tin. The compound typically appears as a colorless to pale yellow liquid and has a faint, sweet odor. Dibutyltin diacetate has gained significant importance in various industrial applications, particularly in the fields of polymers, coatings, and pharmaceuticals.

The discovery of dibutyltin diacetate can be traced back to the mid-20th century when organotin compounds began to be extensively studied for their unique chemical properties and biological activities. The synthesis of dibutyltin diacetate is typically achieved by the reaction of dibutyltin oxide with acetic acid, which results in the formation of this versatile compound. Its development marked a significant advancement in organotin chemistry, allowing for a range of applications in different industries.

One of the primary applications of dibutyltin diacetate is as a catalyst in the production of polyurethane and silicone polymers. In these processes, it facilitates the reaction between polyols and isocyanates, improving the efficiency and rate of polymerization. The use of dibutyltin diacetate as a catalyst enhances the mechanical properties and durability of the resulting polymers, making it a valuable additive in the manufacturing of flexible foams, elastomers, and coatings. Its ability to promote the crosslinking of polymer chains contributes to the development of high-performance materials used in various applications, including automotive and construction industries.

In addition to its role in polymer synthesis, dibutyltin diacetate is utilized in the formulation of paints and coatings. It acts as a drying agent, promoting the curing process of alkyd paints and varnishes. This property enhances the hardness and adhesion of the coatings, resulting in improved performance and longevity. The use of dibutyltin diacetate in coating formulations is particularly important in the production of high-quality finishes for furniture, automotive, and industrial applications.

Moreover, dibutyltin diacetate has shown potential in pharmaceutical applications. Its ability to act as a stabilizing agent for certain drugs has garnered interest in drug formulation research. The compound has been investigated for its biocompatibility and its role in enhancing the solubility and stability of active pharmaceutical ingredients. These characteristics make dibutyltin diacetate a subject of ongoing research in the field of medicinal chemistry.

Despite its beneficial applications, dibutyltin diacetate is associated with environmental and health concerns. Organotin compounds, including dibutyltin diacetate, have been scrutinized due to their potential toxicity and bioaccumulation in aquatic environments. Exposure to organotin compounds may lead to various health issues, including endocrine disruption. Consequently, regulatory agencies have implemented measures to control the use of dibutyltin diacetate and other organotin compounds, emphasizing the importance of safety protocols in industrial settings.

In conclusion, dibutyltin diacetate is a significant organotin compound with diverse applications in polymer production, coatings, and pharmaceuticals. Its role as a catalyst and drying agent highlights its importance in enhancing the performance of various materials and formulations. As research continues to explore its potential uses and address environmental concerns, dibutyltin diacetate is expected to remain relevant in the fields of chemistry and industry.

References

2018. Insight into the mechanism of the catalysis of urethane formation by organotin(IV) dicarboxylate. Reaction Kinetics, Mechanisms and Catalysis.
DOI: 10.1007/s11144-018-1366-4

2020. Organotin Compounds in Industrial Catalysis, Part 2: Processes of Polyurethane Formation. Catalysis in Industry.
DOI: 10.1134/s207005042004008x

2014. Simulation of Catalyzed Urethane Polymerization: An Approach to Expedite Commercialization of Bio-based Materials. Catalysis Surveys from Asia.
DOI: 10.1007/s10563-014-9168-9
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