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84-76-4 Dinonyl phthalate

CAS No. 84-76-4
Product Name Dinonyl phthalate
Synonyms Dinonyl Phthalate (mixture of branched chain isomers);Bisoflex 91;Bisoflex DNP;bisoflex91;bisoflexdnp;bisolflex91;Ceneg;1,2-benzenediacarboxylicaciddinonylester
InChI InChI=1/C26H42O4/c1-3-5-7-9-11-13-17-21-29-25(27)23-19-15-16-20-24(23)26(28)30-22-18-14-12-10-8-6-4-2/h15-16,19-20H,3-14,17-18,21-22H2,1-2H3
Molecular Formula C26H42O4
Molecular Weight 418.61
Density 0.98g/mLat 20°C(lit.)
Boiling point 279-287°C(lit.)
Flash point 216°C
Vapour Pressur
Refractive index n20/D 1.486
Dinonyl phthalate (DINP) is a clear, colorless liquid that is primarily used as a plasticizer in the production of polyvinyl chloride (PVC) products. It was first synthesized in the 1930s as an alternative to phthalates that were considered less toxic. DINP is a member of the phthalate family, which consists of several esters, some of which are used as plasticizers or solvents. In recent years, DINP, along with other phthalates, has come under increasing scrutiny due to concerns about its potential effects on human health and the environment.

Physical and Chemical Properties
DINP has a molecular formula of C26H42O4 and a molecular weight of 418.6 g/mol. It is a high-boiling (386°C), low-volatility liquid with a density of 0.970 g/cm3 at 20°C. Its solubility in water is very low (less than 0.1 g/L), but it is highly soluble in organic solvents such as ethanol, acetone, and chloroform. Its flash point is 201°C, and it is stable under normal conditions.

Synthesis and Characterization:
DINP is produced through a series of reactions that involve the esterification of phthalic anhydride with nonyl alcohol. The reaction is catalyzed by sulfuric acid or p-toluenesulfonic acid. The resulting product is then purified, and the DINP is obtained by distillation. DINP can be characterized using various spectroscopic and chromatographic methods, which allow for the determination of its purity and identity.

Analytical Methods:
Several analytical methods have been developed for the detection and quantification of DINP in various matrices. These include gas chromatography-mass spectrometry (GC-MS), high-performance liquid chromatography (HPLC), and liquid chromatography-mass spectrometry (LC-MS). These methods can detect DINP at very low levels, making them useful tools for monitoring its presence in the environment and in biological samples.

Biological Properties:
DINP has been shown to have endocrine-disrupting properties in both in vitro and in vivo studies. It has been shown to bind to the estrogen receptor and the androgen receptor, leading to alterations in the expression of genes involved in hormone signaling pathways. DINP has also been shown to induce oxidative stress, inflammation, and DNA damage in cells. Its effects on human health are still under investigation, but there is evidence to suggest that it may have adverse effects on reproductive and developmental outcomes.

Toxicity and Safety in Scientific Experiments:
Studies have shown that DINP can have toxic effects on various organ systems in animals, including the liver, kidneys, lungs, and reproductive organs. Exposure to high levels of DINP has also been associated with developmental defects and reduced fertility in animals. The International Agency for Research on Cancer (IARC) has classified DINP as "possibly carcinogenic to humans," based on limited evidence from animal studies. The current safety guidelines for DINP exposure vary among countries, with some countries setting more stringent limits than others.

Applications in Scientific Experiments:
DINP is widely used as a plasticizer in the production of PVC products, such as hoses, wires, and cable coatings. It is also used in the production of other materials, such as flooring, wall coverings, and synthetic leather. Its use in scientific experiments is primarily limited to toxicological studies, where it is used as a model compound for other phthalates and to test the efficacy of various detoxification pathways.

Current State of Research:
Research on DINP is ongoing, with several studies investigating its effects on human health and the environment. Some studies have focused on measuring levels of DINP in various matrices, such as food, air, and water, while others have examined its toxic effects in laboratory animals and cell cultures. There is also ongoing research into alternative plasticizers that can be used as replacements for DINP in PVC products.

Potential Implications in Various Fields of Research and Industry:
The potential implications of DINP use in various fields of research and industry are vast and complex. Its use in the production of PVC products is widespread, and there are currently no viable alternatives that can replace it entirely. Its persistence in the environment and its potential effects on human health and the environment are of particular concern. The development of alternative plasticizers and the implementation of more stringent safety regulations are potential solutions.

Limitations and Future Directions:
There are several limitations to our current understanding of DINP and its effects on human health and the environment. Many of the studies conducted to date have been limited by small sample sizes, incomplete exposure assessments, and a lack of long-term follow-up. Future research should focus on larger, more comprehensive studies that can better characterize the risks associated with DINP exposure. This research should also explore alternative plasticizers and methods for reducing exposure to phthalates in general. Ultimately, a better understanding of the risks associated with DINP exposure is needed to inform public policy and protect human health and the environment.

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