24539-60-4

Usage

Uses

Used in Film Industry:
Decyl hydrogen phthalate is used as a catalyst for the analysis of the kinetics crosslinking oligomers in a film. Its role in this application is to facilitate the crosslinking process, which is essential for the formation of a stable and durable film.
Used in Environmental Research:
As an environmental toxin, decyl hydrogen phthalate is also utilized in research studies to understand its impact on the environment and human health. This knowledge aids in the development of regulations and guidelines to minimize its harmful effects.

InChI:InChI=1/C18H26O4/c1-2-3-4-5-6-7-8-11-14-22-18(21)16-13-10-9-12-15(16)17(19)20/h9-10,12-13H,2-8,11,14H2,1H3,(H,19,20)

Upstream product

• 85-44-9 phthalic anhydride 
• 112-30-1 1-Decanol 

Relevant academic research and scientific papers

Internal Catalysis in Covalent Adaptable Networks: Phthalate Monoester Transesterification As a Versatile Dynamic Cross-Linking Chemistry

Covalent adaptable networks (CANs) often make use of highly active external catalysts to provide swift exchange of the dynamic chemical bonds. Alternatively, milder species can act as internal catalysts when covalently attached to the matrix and in close proximity to the dynamic bonds. In this context, we introduce the dynamic exchange of phthalate monoesters as a novel chemistry platform for covalent adaptable networks. A low-molecular-weight (MW) model study shows that these monoesters undergo fast transesterification via a dissociative mechanism, caused by internal catalysis of the free carboxylic acid, which reversibly forms an activated phthalic anhydride intermediate. Using this dynamic chemistry, a wide series of CANs with a broad range of properties have been prepared by simply curing a mixture of diols and triols with bifunctional phthalic anhydrides. The dynamic nature of the networks was confirmed via recycling experiments for multiple cycles and via stress relaxation using rheology. The networks proved to be resistant to deformation but showed a marked temperature response in their rheological behavior, related to the swift exchange reactions that have a high activation energy (120 kJ/mol). While densely cross-linked and hydrolytically stable polyester networks with low soluble fractions can be obtained, we found that, by swelling the networks in a hot solvent, a gel-to-sol transition happened, which resulted in the full dissolution of the network.

Ecotoxicity and biodegradation of phthalate monoesters

Little is known about the fate and the effects of phthalic acid monoesters. Various of these monoesters ranging from n-butyl to isononyl monoester have been evaluated in respect to their biodegradation behaviour and their acute aquatic toxicity. All esters are readily biodegradable, achieving degradation rates of 90% and more. The acute toxicity values strongly depend on the carbon chain length of the alcohol moiety. The short chain specimen have LC/EC 50 around and above 100 mg/l, with values levelling off to around 30 mg/l for the isononyl monoester.