Pentaerythritol tetra(mercaptopropionate)
[CAS# 7575-23-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Thiol salt
• Name: Pentaerythritol tetra(mercaptopropionate)
• Synonyms: Pentaerythritol tetra(beta-thiopropionate); Pentaerythritol tetra-beta-mercaptopropionate; Pentaerythritol tetrakis(3-mercaptopropanoate); Pentaerythritol tetrakis(mercaptopropionate); Pentaerythritol tetrakis(beta-mercaptopropionate); Pentaerythritol tetrakis(beta-thiopropionate); Pentaerythrityl tetrakis(beta-mercaptopropionate); Q 43; Q 43 (polythiol); QX 40; Tetrakis(3-mercaptopropionate)pentaerythritol; Tetramethylolmethane tetramercaptopropionate; Thiocure PETMP; Thiocure PETMP Low Odor; beta-Mercaptopropionic acid tetraester with pentaerythritol
• Molecular Formula: C₁₇H₂₈O₈S₄
• Molecular Weight: 488.66
• CAS Registry Number: 7575-23-7
• EC Number: 231-472-8
• SMILES: C(CS)C(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS

Properties

• Solubility: Insoluble (7.8E^-3 g/L) (25 °C), Calc.^*
• Density: 1.288±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Refractive index: 1.53 (589.3 nm 25 °C)^**
• Boiling Point: 275 °C (1 mmHg)

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

^** Homberg, Otto A.

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Warning
• Risk Statements: H302-H317-H335-H371-H400-H410
• Safety Statements: P260-P261-P264-P270-P271-P272-P273-P280-P301+P317-P302+P352-P304+P340-P308+P316-P319-P321-P330-P333+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin sensitization	Skin Sens.	1A	H317
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - single exposure	STOT SE	2	H371
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

• Transport Information: UN 3334

Discovery and Applications

Pentaerythritol tetra(mercaptopropionate) is a chemical compound with the molecular formula C₁₀H₁₂O₄S₄. It is known for its unique structure and wide-ranging applications, particularly in the fields of polymer chemistry and material science. The compound, which belongs to the class of mercaptans, features a pentaerythritol core esterified with four mercaptopropionate groups.

The synthesis of pentaerythritol tetra(mercaptopropionate) typically involves the reaction of pentaerythritol with mercaptopropionic acid under acidic conditions. The resulting product is a tetraester in which each hydroxyl group of the pentaerythritol is esterified with a mercaptopropionate group. This structure endows the compound with specific chemical properties that make it valuable in various industrial applications.

One of the primary applications of pentaerythritol tetra(mercaptopropionate) is in the field of polymer chemistry. It is used as a crosslinking agent in the production of thiol-ene and thiol-yne polymers. The compound's mercapto groups participate in thiol-ene or thiol-yne click reactions, which result in highly crosslinked networks with excellent mechanical properties. These polymers are used in a variety of applications, including coatings, adhesives, and composite materials, where enhanced strength, durability, and chemical resistance are required.

In addition to its role as a crosslinking agent, pentaerythritol tetra(mercaptopropionate) is utilized in the formulation of advanced materials such as hydrogels. The compound's ability to form strong crosslinks makes it suitable for creating hydrogels with controlled swelling properties and high mechanical strength. These hydrogels have applications in biomedical fields, including drug delivery systems and tissue engineering.

The compound also finds use in the synthesis of high-performance polymers for electronics and optoelectronics. Pentaerythritol tetra(mercaptopropionate) is incorporated into formulations for electronic encapsulants and coatings, where its crosslinking properties enhance the material's ability to protect sensitive electronic components from environmental stressors.

Furthermore, pentaerythritol tetra(mercaptopropionate) is employed in the production of specialty resins and sealants. Its crosslinking capabilities contribute to the development of resins with improved adhesive properties and resistance to harsh conditions, making it valuable for industrial applications such as construction and automotive industries.

Overall, pentaerythritol tetra(mercaptopropionate) is a versatile chemical compound with significant applications across various fields. Its unique structure and reactivity enable the development of advanced materials with enhanced properties, making it an important compound in the synthesis of high-performance polymers and materials.

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.