2-Ethylhexyl 3-mercaptopropanoate
[CAS# 50448-95-8]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Cyclic carboxylic acid
• Name: 2-Ethylhexyl 3-mercaptopropanoate
• Synonyms: beta-Mercaptopropionic acid 2-ethylhexyl ester
• Molecular Formula: C₁₁H₂₂O₂S
• Molecular Weight: 218.36
• CAS Registry Number: 50448-95-8
• EC Number: 256-589-1
• SMILES: CCCCC(CC)COC(=O)CCS

Properties

• Solubility: Practically insoluble (0.076 g/L) (25 °C), Calc.^*
• Density: 0.957±0.06 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2017 ACD/Labs)

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS09 Danger
• Risk Statements: H302-H317-H319-H331-H400-H410
• Safety Statements: P261-P264-P264+P265-P270-P271-P272-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P316-P321-P330-P333+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1B	H317
Acute toxicity	Acute Tox.	3	H331
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

2-Ethylhexyl 3-mercaptopropanoate, with the chemical formula C11H20O2S, is a notable compound used in various applications across chemical and industrial sectors. This substance, a derivative of mercaptopropanoic acid, has garnered attention for its unique chemical properties and practical uses.

The compound was first synthesized and characterized in the mid-20th century as part of research into the chemistry of mercaptans and their esters. Its synthesis involves the esterification of 3-mercaptopropanoic acid with 2-ethylhexanol, resulting in a compound that combines the reactivity of thiols with the stability of ester groups. This chemical structure provides 2-ethylhexyl 3-mercaptopropanoate with its distinctive characteristics and versatility.

In the field of polymer chemistry, 2-ethylhexyl 3-mercaptopropanoate is utilized as a chain transfer agent in free radical polymerization. Its thiol group can effectively terminate the growth of polymer chains, allowing for control over the molecular weight and distribution of the resulting polymers. This application is particularly important in the production of high-performance polymers and copolymers, where precise control over molecular weight and polymer structure is essential. The compound's ability to modulate polymer properties makes it valuable in the development of materials with tailored characteristics for specific applications.

Another significant application of 2-ethylhexyl 3-mercaptopropanoate is in the formulation of adhesives and sealants. The presence of the thiol group imparts strong adhesive properties and enhances the bonding strength of these materials. The compound’s ester functionality contributes to the flexibility and durability of the adhesive formulations, making them suitable for use in a variety of industrial and consumer applications. The enhanced adhesion and performance of these products are crucial for applications ranging from construction to automotive industries.

Additionally, 2-ethylhexyl 3-mercaptopropanoate is used in the production of metalworking fluids and corrosion inhibitors. Its thiol group provides excellent compatibility with metal surfaces and helps to form protective films that prevent oxidation and corrosion. This application is particularly valuable in industries where metal components are subjected to harsh environments and require protection against degradation. The compound's ability to improve the longevity and performance of metal parts makes it an important component in industrial maintenance and manufacturing processes.

In the field of environmental science, 2-ethylhexyl 3-mercaptopropanoate has been investigated for its potential use in the remediation of heavy metal contaminants. The thiol group has the ability to chelate metal ions, facilitating their removal from contaminated soil and water. This application is important for addressing environmental pollution and ensuring the safe disposal of hazardous materials.

Overall, 2-ethylhexyl 3-mercaptopropanoate is a versatile chemical with a range of applications in polymer chemistry, adhesives, metalworking, and environmental remediation. Its unique chemical properties and practical benefits make it a valuable compound in various industrial processes and scientific research.

References

2001. Modification of gold surface by grafting of poly(ethylene glycol) for reduction in protein adsorption and platelet adhesion. Journal of Biomaterials Science, Polymer Edition, 12(6).
DOI: 10.1163/156856201300194252