Bis(2-butyloctyl) 10-oxononadecanedioate
[CAS# 2036272-58-7]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Bis(2-butyloctyl) 10-oxononadecanedioate
• Molecular Formula: C₄₃H₈₂O₅
• Molecular Weight: 679.11
• CAS Registry Number: 2036272-58-7
• SMILES: CCCCC(COC(=O)CCCCCCCCC(=O)CCCCCCCCC(=O)OCC(CCCCCC)CCCC)CCCCCC

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.463, Calc.^*
• Boiling Point: 700.6±45.0 ºC (760 mmHg), Calc.^*
• Flash Point: 272.8±28.8 ºC, Calc.^*

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

Discovory and Applicatios

Bis(2-butyloctyl) 10-oxononadecanedioate is a chemical compound that has gained prominence in the fields of materials science and industrial chemistry due to its unique structure and versatile applications. This compound is characterized by the presence of two 2-butyloctyl groups and a nonadecanedioate backbone with an oxo functionality at the 10-position, contributing to its distinct physicochemical properties.

The discovery of Bis(2-butyloctyl) 10-oxononadecanedioate is linked to the ongoing exploration of ester-based compounds, particularly those with long alkyl chains, for their potential use in various industrial applications. The compound's structure, which includes two branched 2-butyloctyl groups attached to the nonadecanedioate core, imparts significant hydrophobicity and lipophilicity. This makes it highly suitable for applications where these properties are advantageous, such as in the formulation of high-performance lubricants and plasticizers.

One of the primary applications of Bis(2-butyloctyl) 10-oxononadecanedioate is as a plasticizer in the production of flexible polymers. Plasticizers are essential additives that increase the flexibility, durability, and workability of polymeric materials by reducing the intermolecular forces between polymer chains. The branched structure of the 2-butyloctyl groups in this compound contributes to its efficiency as a plasticizer, as it helps to lower the glass transition temperature of polymers, making them more pliable at lower temperatures. This property is particularly valuable in the manufacturing of flexible PVC, elastomers, and other polymer-based products used in various industries, including construction, automotive, and consumer goods.

In addition to its role as a plasticizer, Bis(2-butyloctyl) 10-oxononadecanedioate is also utilized as a lubricant in industrial applications. The compound's long alkyl chains and ester groups provide excellent lubricity and thermal stability, which are critical for reducing friction and wear in mechanical systems operating under extreme conditions. Its ability to form a stable, adherent film on metal surfaces enhances its effectiveness as a lubricant, making it particularly useful in high-performance engines, machinery, and other mechanical systems where reliable lubrication is essential.

The synthesis of Bis(2-butyloctyl) 10-oxononadecanedioate typically involves the esterification of 10-oxononadecanedioic acid with 2-butyloctanol. This process is carried out under controlled conditions to ensure the selective formation of the desired ester bonds while minimizing side reactions. The choice of 2-butyloctanol as the alcohol component is significant, as the branched alkyl structure enhances the compound's solubility in non-polar solvents and contributes to its overall stability under various environmental conditions.

Beyond its industrial applications, Bis(2-butyloctyl) 10-oxononadecanedioate has potential uses in the formulation of personal care products, particularly as an emollient in skin care formulations. The compound's ability to provide a smooth, non-greasy feel on the skin, coupled with its moisturizing properties, makes it an attractive ingredient in lotions, creams, and other cosmetic products. Its compatibility with other ingredients and its low irritation potential further enhance its suitability for use in formulations designed for sensitive skin.

As research into ester-based compounds continues, the applications of Bis(2-butyloctyl) 10-oxononadecanedioate are expected to expand. Its unique structural features, including the branched 2-butyloctyl groups and the oxononadecanedioate backbone, ensure that it remains a compound of interest in the development of advanced materials and formulations across a variety of industries.