2,2,4-Trimethyl-1,3-pentanediolmono(2-methylpropanoate)
[CAS# 25265-77-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Acid ester compound
• Name: 2,2,4-Trimethyl-1,3-pentanediolmono(2-methylpropanoate)
• Synonyms: Texanol ester alcohol; 2,2,4-Trimethyl-1,3-pentanediol monoisobutyrate
• Molecular Formula: C₁₂H₂₄O₃
• Molecular Weight: 216.32
• CAS Registry Number: 25265-77-4
• EC Number: 246-771-9
• SMILES: CC(C)C(C(C)(C)COC(=O)C(C)C)O

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*, 0.95 g/mL (Expl.)
• Melting point: -50 ºC (Expl.)
• Index of Refraction: 1.444, Calc.^*, 1.441 (Expl.)
• Boiling Point: 249.0±13.0 ºC (760 mmHg), Calc.^*, 254-261 ºC (Expl.)
• Flash Point: 85.1±12.6 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335-H412
• Precautionary Statements: P261-P273-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

2,2,4-Trimethyl-1,3-pentanediol mono(2-methylpropionate), commonly referred to as TMPDMP, is an ester compound that has attracted much attention for its useful properties in a variety of industrial applications. The compound belongs to the class of alkyl esters, specifically pentanediol esters, which are known for their unique combination of solubility, stability, and high-performance properties. TMPDMP is most commonly used as a plasticizer, solvent, and intermediate in the synthesis of more complex chemicals.

The discovery of TMPDMP dates back to the mid-20th century, when the synthesis of functional esters with specific properties suitable for industrial and commercial applications was under intensive investigation. Researchers at the time were looking for compounds that could improve the properties of materials such as plastics, coatings, and adhesives. 2,2,4-Trimethyl-1,3-pentanediol was esterified with 2-methylpropionate to produce TMPDMP, whose properties made it a valuable addition to the chemical industry.

One of the main applications of TMPDMP is as a plasticizer in the production of flexible polyvinyl chloride (PVC) and other thermoplastic materials. As a plasticizer, TMPDMP enhances the flexibility, processability and durability of PVC, making it an important ingredient in products ranging from flooring and wall coverings to cables and automotive parts. The presence of the 2,2,4-trimethyl group in TMPDMP adds steric hindrance, which helps reduce its volatility and improves thermal stability. These properties are particularly important in applications that require long-term durability and resistance to environmental stresses.

In addition to its role as a plasticizer, TMPDMP is used as a solvent in coatings and paints. The ester has good solubility for a wide range of resins, including those used in lacquers and varnishes. TMPDMP helps improve the flow, drying time and appearance of these coatings, making it a solvent of choice for high-quality finishes. Its relatively low odor and low toxicity compared to other solvents further enhance its appeal in consumer-facing products such as paints and coatings for furniture, automobiles and home furnishings.

The chemical's excellent solubility and compatibility with a wide range of formulations also make it useful in the formulation of adhesives and sealants. TMPDMP helps improve the bonding properties of these materials while also helping to increase their flexibility and crack resistance. This makes it valuable in industries such as construction, automotive, and electronics that require durable, flexible bonds.

Another area of ??application for TMPDMP is in the synthesis of specialty chemicals. It can be used as a starting material or intermediate in the production of high-value chemicals for the manufacture of fragrances, surfactants, and other high-performance chemicals. Its ability to undergo further chemical transformations makes it a versatile building block for a variety of synthetic pathways.

Additionally, TMPDMP has a relatively low environmental impact compared to some other plasticizers and solvents, so it can be used in formulations that comply with stricter environmental and health regulations. As the industry continues to move toward more environmentally friendly alternatives, TMPDMP is viewed as a more sustainable option in certain applications, especially in terms of reduced toxicity and environmental persistence.

In summary, 2,2,4-trimethylpentanediol mono(2-methylpropionate) is a versatile and valuable compound with important applications in the chemical industry. Its properties as an intermediate in the production of plasticizers, solvents and other chemicals make it indispensable in a wide range of industrial applications, especially in the manufacture of plastics, coatings, adhesives and specialty chemicals.

References

2022. Absolute Stereochemistry of TXIB, a Bioactive Plasticizer That Inhibits Oviposition of the Peach Fruit Moth. Journal of Chemical Ecology, 48(6).
DOI: 10.1007/s10886-022-01372-4

2012. Ambient measurements of 2,2,4-trimethyl, 1,3-pentanediol monoisobutyrate in Southern California. Journal of the Air & Waste Management Association, 62(8).
DOI: 10.1080/10962247.2012.666223

2010. Common Household Chemicals and the Allergy Risks in Pre-School Age Children. PLoS ONE, 5(10).
DOI: 10.1371/journal.pone.0013423