Caproic acid, 1,1 ‘- [1,4-phenyldioxo (2,1-ethanediyl)] ester (CAS 145522-55-0): A comprehensive analysis of a high-purity diester compound
In the fields of fine chemicals and materials science, diester compounds are widely used in various fields such as plasticizers, lubricants, cosmetic raw materials, and pharmaceutical intermediates due to their unique molecular structure and properties. Hexanoic acid, 1,1 ‘- [1,4-phenyldioxy (2,1-ethanediyl)] ester, is one of the representative aromatic diester compounds. This article will provide a systematic introduction to this compound from its basic information, physicochemical properties, synthesis, and application prospects.
1. Basic Information and Chemical Structure
The molecular formula of this compound is C ₂₂ H ∝₄₆, the molecular weight is 394.5, and the CAS registration number is 145522-55-0. Structurally, it is a diester formed by esterification reaction between two molecules of hexanoic acid and 1,4-phenyldioxo (2,1-ethanediyl). The benzene ring in the center of the molecule is connected to two hexanoate groups through an oxygen atom and an ethylene glycol chain, forming a symmetrical chain like structure. This special chemical structure endows the compound with good flexibility and thermal stability.
2.Physical and Chemical Properties
According to existing database data, the key physical parameters of 145522-55-0 are as follows:
Nature: Parameters
Boiling point: 478.1 ± 25.0 ° C (predicted value)
Density: 1.050 ± 0.06 g/cm ³ (predicted value)
Appearance: Typically colorless to pale yellow liquid or low melting point solid
Structural formula：
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The higher boiling point (about 478 ° C) indicates that the compound has good thermal stability at room temperature and pressure, making it suitable for use in processing environments that require high temperature resistance. The predicted density is about 1.05 g/cm ³, slightly higher than common plasticizers such as dioctyl phthalate (about 0.98 g/cm ³), which may be related to the presence of benzene rings and multiple ester oxygen atoms in its molecules.
It is worth noting that hexanoic acid, 1,1 ‘- [1,4-phenyldioxo (2,1-ethanediyl)] ester, should have good solubility in conventional organic solvents such as toluene, ethyl acetate, and acetone, but lower solubility in water, which is a typical characteristic of long-chain fatty acid ester compounds.
3.Synthetic method
1)Direct esterification method: Using 1,4-phenyldioxo (2,1-ethanediyl) (i.e. p-phenylenediol (2-hydroxyethyl) ether) as raw material, esterification reaction is carried out with excess hexanoic acid under acid catalysis (such as p-toluenesulfonic acid) and dehydration conditions. The raw materials for this route are easy to obtain and operate, but the reaction requires a higher temperature (usually 150-200 ° C) to promote dehydration.
2)Ester exchange method: The ester exchange reaction between methyl or ethyl hexanoate and the above-mentioned diols can be carried out under mild conditions, and the product purity is high.
At present, domestic chemical reagent suppliers have achieved commercial production of this compound. Henan Career Chemical Co. can provide this product with a purity of 98% and support small batch packaging such as 50g, 100g, 500g, indicating that its synthesis route is relatively mature.
4.Potential application areas
1) High performance plasticizer:
Due to the presence of benzene rings and long-chain fatty acid esters in its molecules, it is expected to be used as an environmentally friendly plasticizer for polar polymer materials such as polyvinyl chloride (PVC), providing good flexibility and low-temperature performance.
2) Lubricating base oil or additive:
Long chain diesters typically have excellent lubricity and anti-wear properties, and can be used in special lubricant formulations.
3) Cosmetics and personal care products:
Ester compounds are common moisturizers and emulsifiers in cosmetics, which may be suitable for skincare and makeup products due to their good skin feel and safety.
4)Drug delivery or sustained-release materials:
Their amphiphilic molecular structure (lipophilic end+hydrophilic ether chain) makes them potential as drug excipients or microcapsule wall materials.
5.Safety and storage recommendations
At present, the specific hazard classification of 145522-55-0 has not been disclosed in detail in public databases, but as an organic ester, it is generally recommended to:
Store in a cool and ventilated warehouse, away from sources of fire and heat.
It should be stored separately from strong oxidants, strong acids, and strong bases.
It is recommended to wear protective gloves and goggles during operation to avoid direct skin contact.
If there is a leak, use inert absorbent materials to absorb and dispose of it according to local environmental regulations.
In addition, due to the high boiling point of the compound (about 478 ° C), it is not easily volatile during distillation or high-temperature processing, but its vapor or decomposition products (such as hexanoic acid) may be irritating and require good ventilation.
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