2,2,4-Trimethyl-1,3-pentanediol diisobutyrate
[CAS# 6846-50-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Butyl ester compound
• Name: 2,2,4-Trimethyl-1,3-pentanediol diisobutyrate
• Synonyms: [2,2,4-trimethyl-3-(2-methylpropanoyloxy)pentyl] 2-methylpropanoate
• Molecular Formula: C₁₆H₃₀O₄
• Molecular Weight: 286.41
• CAS Registry Number: 6846-50-0
• EC Number: 229-934-9
• SMILES: CC(C)C(C(C)(C)COC(=O)C(C)C)OC(=O)C(C)C

Properties

• Density: 0.941 g/mL
• Melting point: -70 ºC
• Boiling point: 280 ºC
• Refractive index: 1.434
• Flash point: 113 ºC

Safety Data

• Hazard Symbols: GHS08 Warning
• Hazard Statements: H361-H412
• Precautionary Statements: P203-P273-P280-P318-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Reproductive toxicity	Repr.	2	H361
Reproductive toxicity	Repr.	2	H361d
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

2,2,4-Trimethyl-1,3-pentanediol diisobutyrate, commonly known as TMPDIB, is a chemical compound that belongs to the class of ester compounds. It is derived from 2,2,4-trimethyl-1,3-pentanediol and isobutyric acid. This ester is widely used as a plasticizer, which enhances the flexibility and workability of polymers, particularly in applications involving polyvinyl chloride (PVC) and other thermoplastic materials. TMPDIB has gained significant importance in both industrial and commercial applications due to its excellent performance properties and favorable environmental profile compared to other traditional plasticizers.

The compound was first synthesized in the mid-20th century when there was an increasing need for more efficient and safer plasticizers to replace phthalates, which were under scrutiny due to potential health risks. The development of TMPDIB was driven by the need for a non-toxic, biodegradable alternative that could offer high compatibility with a wide range of polymers. Its synthesis involves esterification reactions between 2,2,4-trimethyl-1,3-pentanediol and isobutyric acid, and the compound is typically produced in large quantities for industrial applications.

One of the primary uses of TMPDIB is as a plasticizer in the production of flexible PVC products. Plasticizers are substances that are added to polymers to increase their flexibility, durability, and processability. TMPDIB is particularly effective in enhancing the performance of PVC, making it more suitable for a variety of applications such as flooring, wall coverings, electrical cables, and artificial leather. Unlike phthalate-based plasticizers, TMPDIB is considered to have a lower environmental impact and is less likely to cause health concerns, which has made it a preferred choice in many industries.

In addition to its use in PVC, TMPDIB is also used as a plasticizer in other polymer systems, including coatings and adhesives. Its ability to improve the flexibility, adhesion, and durability of these materials makes it a valuable component in the manufacturing of paints, sealants, and coatings used in both industrial and consumer products. These applications benefit from TMPDIB's stability, low volatility, and resistance to migration, ensuring that the plasticized products maintain their desired properties over time.

TMPDIB also has applications in the production of synthetic rubber, where it is used as a processing aid to improve the flow properties and processing efficiency of the rubber. The compound can be added to rubber formulations to enhance their flexibility and mechanical properties, making them more suitable for use in a variety of automotive and industrial applications.

Furthermore, TMPDIB has been explored for use in the production of biodiesel as a potential alternative solvent for transesterification processes. The compound's low toxicity and ability to act as a solvent in the reaction make it a promising candidate for sustainable biodiesel production. Research into this application continues, as the demand for eco-friendly and efficient fuel production processes increases globally.

Due to its favorable toxicity and environmental profile, TMPDIB is often used in consumer products where human contact is likely, such as in flooring materials, toys, and medical devices. It is generally regarded as safe compared to other plasticizers, and its use in such applications aligns with the growing demand for safer, greener chemicals in consumer goods.

In conclusion, 2,2,4-Trimethyl-1,3-pentanediol diisobutyrate is an important chemical compound with wide applications in the polymer industry, especially as a plasticizer in flexible PVC and other polymer systems. Its discovery and use have contributed to the development of safer, more environmentally friendly materials that are used in a variety of industries, from construction and automotive to healthcare and consumer products.

References

2019. Quantitative Determination of 2-Ethyl-1-hexanol, Texanol and TXIB in In-door Air Using a Solid-Phase Extraction-type Collection Device Followed by Gas Chromatography-Mass Spectrometry. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry, 35(4).
DOI: 10.2116/analsci.19p033

2019. Structural characterization of potential endocrine disrupting activity of alternate plasticizers di-(2-ethylhexyl) adipate (DEHA), acetyl tributyl citrate (ATBC) and 2,2,4-trimethyl 1,3-pentanediol diisobutyrate (TPIB) with human sex hormone-binding globulin. Reproductive toxicology (Elmsford, N.Y.), 83.
DOI: 10.1016/j.reprotox.2018.11.003

1972. The toxicology and fate of 2,2,4-trimethyl-1,3-pentanediol diisobutyrate. Toxicology and Applied Pharmacology, 22(3).
DOI: 10.1016/0041-008x(72)90244-x