Dibutyltin maleate
[CAS# 78-04-6]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organotin
• Name: Dibutyltin maleate
• Synonyms: 2,2-Dibutyl-1,3,2-dioxastannepin-4,7-dione
• Molecular Formula: C₁₂H₂₀O₄Sn
• Molecular Weight: 346.98
• CAS Registry Number: 78-04-6
• EC Number: 201-077-5
• SMILES: CCC[Sn]1(OC(=O)C=CC(=O)O1)CCCC

Properties

• Melting point: 135-140 °C
• Boiling Point: 324.1±25.0 °C (760 mmHg), Calc.^*
• Flash Point: 149.8±23.2 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS08;GHS09 Danger
• Risk Statements: H302-H314-H317-H318-H330-H341-H360-H370-H372-H410-H411
• Safety Statements: P203-P260-P261-P264-P264+P265-P270-P271-P272-P273-P280-P284-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P308+P316-P316-P317-P318-P319-P320-P321-P330-P333+P317-P362+P364-P363-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	2	H330
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Germ cell mutagenicity	Muta.	2	H341
Skin sensitization	Skin Sens.	1	H317
Reproductive toxicity	Repr.	1B	H360
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Skin corrosion	Skin Corr.	1C	H314
Specific target organ toxicity - single exposure	STOT SE	1	H370
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin corrosion	Skin Corr.	1B	H314
Skin irritation	Skin Irrit.	2	H315
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H311
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	2	H310

• Transport Information: UN 3146

Discovery and Applications

Dibutyltin maleate is an organotin compound with the chemical formula C₁₄H₂₄O₄Sn. It is derived from the reaction of dibutyltin oxide and maleic acid. This compound was first synthesized in the mid-20th century, coinciding with the growing interest in organotin chemistry, which gained prominence due to the diverse applications of organotin compounds in various fields.

The primary applications of dibutyltin maleate are in the fields of polymer chemistry and materials science. It is commonly used as a stabilizer and catalyst in the production of polyvinyl chloride (PVC) and other thermoplastic materials. In PVC formulations, dibutyltin maleate acts as a heat stabilizer, enhancing the thermal stability of the polymer during processing and prolonging its lifespan. This is particularly important as PVC is widely used in construction, electrical insulation, and consumer products.

In addition to its role as a stabilizer, dibutyltin maleate serves as a curing agent in the production of polyurethane foams and elastomers. The compound helps facilitate the crosslinking of polymer chains, resulting in materials with desirable mechanical properties and resistance to degradation. This application is significant in various industries, including automotive, construction, and consumer goods, where durable and flexible materials are required.

Dibutyltin maleate is also investigated for its potential as a biocide in agricultural applications. Its effectiveness against certain pests and fungi makes it a candidate for use in agricultural formulations aimed at protecting crops. However, the use of organotin compounds in agriculture has raised environmental concerns due to their toxicity and persistence in the environment. As a result, regulatory measures have been implemented to limit their use and promote safer alternatives.

Despite these concerns, dibutyltin maleate remains a valuable compound in the chemical industry. Its unique properties make it suitable for various applications, particularly in the production of high-performance polymers. Ongoing research continues to explore new applications and formulations involving dibutyltin maleate, aiming to enhance its utility while minimizing environmental impact.

In summary, dibutyltin maleate is an organotin compound that plays a crucial role as a stabilizer and catalyst in polymer production, particularly in PVC and polyurethane applications. While its utility is significant, awareness of its environmental implications has led to a push for responsible use and the development of safer alternatives in the industry.

References

2020. Organotin Compounds in Industrial Catalysis, Part 2: Processes of Polyurethane Formation. Catalysis in Industry, 12(4).
DOI: 10.1134/s207005042004008x

2020. Preparation and characterization of some new antimicrobial thermally stable PVC formulations. Polymer Bulletin, 77(5).
DOI: 10.1007/s00289-020-03433-8

2021. Factors Affecting the Properties of Polyvinylchloride (PVC) Nano-, Micro- and Macro-Blends. Springer Series on Polymer and Composite Materials, Not applicable.
DOI: 10.1007/978-3-030-78455-3_5