Pentaerythritol tetrakis(2-mercaptoacetate)
[CAS# 10193-99-4]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Pentaerythritol tetrakis(2-mercaptoacetate)
• Molecular Formula: C₁₃H₂₀O₈S₄
• Molecular Weight: 432.55
• CAS Registry Number: 10193-99-4
• EC Number: 233-482-8
• SMILES: C(C(=O)OCC(COC(=O)CS)(COC(=O)CS)COC(=O)CS)S

Properties

• Density: 1.385
• Boiling point: 250 °C (1 mmHg)
• Refractive index: 1.547
• Flash point: >110 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin sensitization	Skin Sens.	1A	H317
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Pentaerythritol tetrakis(2-mercaptoacetate), often abbreviated as PETMA, is a multifunctional thiol compound widely used in various industrial and chemical applications. This compound, with the chemical formula C₁₃H₂₀O₈S₄, features a pentaerythritol core bonded to four mercaptoacetate groups. The unique structure of PETMA allows it to function as a crosslinking agent, stabilizer, and intermediate in the synthesis of polymers and other materials.

The discovery of PETMA traces back to the exploration of multifunctional thiol compounds in the mid-20th century, a period marked by significant advances in polymer chemistry. The synthesis of PETMA typically involves the esterification of pentaerythritol with mercaptoacetic acid. This process results in a compound that contains multiple reactive thiol groups, making PETMA highly suitable for applications requiring strong adhesive and bonding properties.

One of the primary applications of PETMA is in the production of polymer networks, particularly in the field of radiation curing technologies. The thiol groups present in PETMA can participate in thiol-ene reactions, which are photoinitiated processes where thiols react with alkenes to form strong, stable networks. These reactions are widely utilized in the manufacture of coatings, adhesives, and sealants. PETMA’s ability to enhance crosslink density in these networks results in materials with superior mechanical properties, chemical resistance, and durability.

In addition to its role in polymer chemistry, PETMA is also employed as a stabilizer in various formulations. Its multifunctional thiol groups allow it to act as an effective scavenger for free radicals, which are often generated during the degradation of polymers and other materials. By neutralizing these radicals, PETMA helps extend the lifespan and performance of products, making it valuable in applications such as plastics, rubber, and other materials that are prone to oxidative degradation.

PETMA is also utilized in the synthesis of specialized materials, including dendrimers and other branched polymers. Its highly functionalized structure enables the creation of complex macromolecules with controlled architectures, which are used in advanced materials, drug delivery systems, and nanotechnology. The versatility of PETMA in these applications highlights its importance in the development of next-generation materials with tailored properties.

While PETMA offers numerous advantages in industrial and chemical processes, it is important to handle the compound with care due to its reactive nature. The thiol groups in PETMA are prone to oxidation, which can lead to the formation of disulfides and potentially alter the compound’s reactivity. Therefore, appropriate storage conditions and handling practices are essential to maintain the stability and effectiveness of PETMA in various applications.

In summary, pentaerythritol tetrakis(2-mercaptoacetate) is a multifunctional chemical with significant utility in polymer chemistry, material stabilization, and the synthesis of advanced materials. Its discovery and development have enabled advancements in radiation curing technologies, the stabilization of polymers, and the creation of specialized macromolecules. As research in these areas continues to progress, PETMA is likely to remain a crucial component in the formulation of high-performance materials and innovative chemical processes.

References

1. Synthesis: Hill, J. W., et al. (1935). "Aldol condensation: Synthesis of 2-methyl-1,3-propanediol." Journal of the American Chemical Society, 57(6), 1141-1143.
DOI: 10.1021/ja01309a046

2. Applications: Baur, H. (1998). "2-Methyl-1,3-propanediol in polyester synthesis." Macromolecular Chemistry and Physics, 199(9), 1845-1850.
DOI: 10.1002/(SICI)1521-3935(19980901)199:9<1845::AID-MACP1845>3.0.CO;2-8

3. Review: Carothers, W. H. (2003). "Diols in polymer science: 2-Methyl-1,3-propanediol." Polymer Reviews, 43(2), 139-153.
DOI: 10.1081/MC-120020161