Trimethylolpropane tris(3-mercaptopropionate)
[CAS# 33007-83-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Thiol salt
• Name: Trimethylolpropane tris(3-mercaptopropionate)
• Synonyms: 3TP6; Epicure QX 30; Epikure QX 30; JER Cure QX 30; Mercaptate P 33; P 33; P 33 (ester); PEMP 2; QX 30; TMMP; TMPMP; TMTP; Thiocure TMPMP; Trimethylolpropane tris(beta-mercaptopropionate)
• Molecular Formula: C₁₅H₂₆O₆S₃
• Molecular Weight: 398.56
• CAS Registry Number: 33007-83-9
• EC Number: 251-336-1
• SMILES: CCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS

Properties

• Solubility: Practically insoluble (0.02 g/L) (25 ºC), Calc.^*
• Density: 1.212±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Boiling Point: 220 ºC (0.3 mmHg)
• Refractive index: 1.518

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Hazard Statements: H302-H315-H317-H319-H335-H400-H410
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P272-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Skin sensitization	Skin Sens.	1B	H317
Skin sensitization	Skin Sens.	1A	H317

• Transport Information: UN 3334

Discovory and Applicatios

Trimethylolpropane tris(3-mercaptopropionate) is a specialized chemical compound known for its role in polymer chemistry, particularly in the synthesis of high-performance materials. This compound is a derivative of trimethylolpropane, where three mercaptopropionate groups are esterified to the hydroxyl groups of the central trimethylolpropane molecule. Its unique structure imparts distinctive properties that make it valuable in various industrial applications.

The discovery of trimethylolpropane tris(3-mercaptopropionate) stems from the need for multifunctional monomers that can enhance the properties of polymeric materials. Its synthesis involves the reaction of trimethylolpropane with 3-mercaptopropionic acid, resulting in a tri-functional thiol ester. This compound was identified for its potential to improve the performance characteristics of polymers through the introduction of multiple thiol groups, which can participate in cross-linking reactions.

One of the primary applications of trimethylolpropane tris(3-mercaptopropionate) is in the field of coatings and adhesives. The compound serves as a cross-linking agent that enhances the chemical resistance, mechanical strength, and adhesion properties of these materials. Its thiol groups can react with other polymerizable components, creating a network structure that imparts durability and stability to the final product. This makes it particularly useful in formulating high-performance coatings that are resistant to environmental degradation.

In the realm of polymer chemistry, trimethylolpropane tris(3-mercaptopropionate) is employed as a key component in the production of high-performance resins and composites. The compound's ability to cross-link with other polymerizable monomers results in materials with superior mechanical properties, such as increased tensile strength and impact resistance. These enhanced properties are crucial for applications in industries such as automotive, aerospace, and construction, where material performance and reliability are essential.

The compound is also used in the development of specialty polymers with tailored properties. For example, in the production of elastomers, trimethylolpropane tris(3-mercaptopropionate) contributes to the formation of cross-linked networks that provide flexibility and resilience. Its inclusion in polymer formulations allows for the customization of material properties to meet specific performance requirements.

Another notable application of trimethylolpropane tris(3-mercaptopropionate) is in the field of adhesives and sealants. The compound's ability to form strong, cross-linked bonds enhances the adhesive strength and longevity of these products. This makes it valuable in various industrial and consumer applications where reliable bonding and sealing are required.

Research into the use of trimethylolpropane tris(3-mercaptopropionate) continues to explore its potential in emerging fields such as biomaterials and environmental technologies. Its unique chemical properties and reactivity make it a candidate for applications requiring specialized material characteristics, such as controlled release systems or environmental remediation.

Overall, trimethylolpropane tris(3-mercaptopropionate) is a significant compound in polymer science due to its multifunctional nature and ability to improve material properties through cross-linking. Its diverse applications in coatings, adhesives, resins, and specialty polymers underscore its importance in advancing material technology and performance.

References

Charles E. Hoyle, Andrew B. Lowe and Christopher N. Bowman. Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis, Chem. Soc. Rev., 2010, 39, 1355.