Pentaerythritol
[CAS# 115-77-5]

Identification

• Classification: Organic raw materials >> Alcohols, phenols, phenolic compounds and derivatives >> Acyclic alcohol
• Name: Pentaerythritol
• Synonyms: Tetrakis(hydroxymethyl)methane; 2,2-Bis(hydroxymethyl)-1,3-propanediol
• Molecular Formula: C₅H₁₂O₄
• Molecular Weight: 136.15
• CAS Registry Number: 115-77-5
• EC Number: 204-104-9
• SMILES: C(C(CO)(CO)CO)O

Properties

• Density: 1.396
• Melting point: 257-263 °C
• Boiling point: 276 °C (30 mmHg)
• Flash point: 240 °C
• Water solubility: 1 g/18 mL (15 °C)

Safety Data

• Safety Statements: S24/25

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Pentaerythritol, chemically known as 2,2-bis(hydroxymethyl)propane-1,3-diol, was first synthesized in 1931 from the reaction of formaldehyde with acetaldehyde in the presence of an alkaline catalyst. The synthesis produces a white crystalline solid with a tetraol structure in which four hydroxyl groups (-OH) are attached to the central carbon atom. This unique molecular structure imparts exceptional stability and reactivity, making pentaerythritol a valuable building block in chemical synthesis.

Pentaerythritol is widely used in the production of alkyd resins, which are essential binders in oil-based paints and coatings. These resins have excellent durability, adhesion, and weatherability, making them ideal for architectural, automotive, and industrial applications.

In the explosives industry, pentaerythritol is a key ingredient in the production of high-performance explosives such as PETN (pentaerythritol tetranitrate). PETN has a high energy density and stability, making it valuable in military and commercial explosives applications.

Pentaerythritol derivatives are useful in pharmaceutical formulations, particularly the synthesis of cardiovascular drugs and pharmaceutical intermediates. Its multifunctional nature allows for modification of pharmacological properties and drug delivery systems.

As a multifunctional alcohol, pentaerythritol is used as a plasticizer in polymer production to enhance the flexibility and elasticity of plastics and synthetic rubbers. It is also used as a stabilizer and antioxidant in lubricants and hydraulic fluids, improving their performance and service life.

In addition to its primary uses, pentaerythritol also aids in the production of adhesives, lubricants, textiles, and flame retardants. Its versatility in chemical synthesis supports innovations in green chemistry and sustainable manufacturing practices.

Ongoing research focuses on optimizing pentaerythritol production processes to improve efficiency and sustainability. In addition, research explores its potential applications in renewable energy technologies, biodegradable polymers, and carbon capture systems, highlighting its role in advancing environmental stewardship and industrial innovation.

Due to its wide range of industrial applications, regulatory agencies monitor the manufacture, handling, and disposal of pentaerythritol to ensure compliance with environmental and health safety standards. Comprehensive risk assessments and mitigation strategies are implemented to minimize potential hazards associated with its production and use.

References

2022. Evaluation of pentaerythritol-based and trimethylolpropane-based cationic lipidic materials for gene delivery. Bioorganic & Medicinal Chemistry Letters.
DOI: 10.1016/j.bmcl.2022.128635

2018. Pentaerythritol Tetrasalicylate in the Chemical Composition of Root Canal Sealers. Brazilian Dental Journal.
DOI: 10.1590/0103-6440201801441

2012. Efficient siRNA Delivery Using a Polyamidoamine Dendrimer with a Modified Pentaerythritol Core. Pharmaceutical Research.
DOI: 10.1007/s11095-012-0676-x