P-Terphenyl CAS 92-94-4

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P-terphenyl, white crystal, molecular formula C18H14. Soluble in hot benzene, slightly soluble in ether and carbon disulfide, extremely insoluble in ethanol and acetic acid. Insoluble in water. For organic synthesis; As an organic scintillation reagent, it is a luminescent substance of scintillation counter; Mixed with biphenyl can be used as a heat carrier for nuclear power plants.

1. P-Terphenyl is used for organic synthesis, as organic scintillation reagent, and is the luminescent material of scintillation counter;

2. Mixed with biphenyl can be used as heat carrier of nuclear power plant;

3. Liquid crystal, pharmaceutical intermediate, scintillation reagent.

4. It is mainly used as a scintillator for the production of plastic particles and thin plastic sheets.

5. It is also one of the basic intermediates for the preparation of biphenyl liquid crystal materials and the basic raw material for the synthesis of antibacterial cyclic peptides (4-carboxyl-p-triphenyl, CTP).

6. It can also prepare 4,4-dicarboxy-p-triphenyl (DCTP), which is the main raw material for preparing biphenyl polyamide materials.

► Organic Scintillators

P-terphenyl is a key component in organic scintillation detectors, which convert ionizing radiation into visible light for measurement. When doped with fluorescent agents like 1,4-bis(5-phenyloxazol-2-yl)benzene (POPOP), p-terphenyl exhibits high scintillation efficiency and fast decay times (~2.8 ns), making it ideal for detecting alpha, beta, and gamma particles in nuclear physics and medical imaging. Its radiation resistance and compatibility with plastic matrices further enhance its utility in portable detectors and radiation shielding.

► Heat Transfer Fluids

The compound's high boiling point and thermal stability have led to its use as a heat transfer fluid in nuclear power plants, where it operates safely at temperatures exceeding 300°C. Mixed with biphenyl, p-terphenyl forms eutectic blends that optimize heat transfer efficiency while minimizing corrosion risks. Recent studies suggest that doped p-terphenyl variants may exhibit superconductivity at temperatures up to 123 K, opening doors to advanced energy storage systems.

► Pharmaceutical Intermediates

P-terphenyl and its derivatives serve as precursors in synthesizing bioactive molecules. For example, 4,4′-diaminoterphenyl, a p-terphenyl derivative, is used to produce dyes, polymers, and pharmaceuticals. Natural p-terphenyls isolated from fungi and marine organisms demonstrate cytotoxic, antimicrobial, and antioxidant properties, with potential applications in cancer therapy and antibiotic development. Notably, p-terphenyl derivatives from Aspergillus species show significant anti-tumor effects in gastric and pancreatic cancer models, inhibiting metastasis and inducing apoptosis in vitro.

► Liquid Crystals and OLED Materials

The planar structure of p-terphenyl makes it a valuable building block for liquid crystal displays (LCDs) and organic light-emitting diodes (OLEDs). Its derivatives, such as alkyl-substituted p-terphenyls, exhibit nematic or smectic phases, enabling their use in LCD alignment layers and electro-optical switches. In OLEDs, p-terphenyl-based hole transport layers enhance device efficiency and lifespan by facilitating charge carrier mobility.

► Analytical Chemistry

P-terphenyl's stable fluorescence emission at 276 nm (in cyclohexane) makes it a reference standard in UV-Vis spectroscopy and chromatographic detection. It is also employed as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for analyzing large biomolecules like proteins and polymers.

There are three methods for preparing p-terphenyl.

The first is to obtain the target product, from the distillation residue produced by the production of biphenyl by high-temperature synthesis and distillation of biphenyl as raw material through secondary dissolution, filtration and secondary distillation; The specific steps are as follows:

(1) Melting and filtration: heat the distillate residue, control the temperature to 150-200 ℃, melt it, and then filter for 1-2h to remove mechanical impurities;

(2) Dissolution: dissolve the above residual solution with organic solvent at 30-60 ℃;

(3) Purification and separation: the product of the previous step is centrifuged and then distilled, and the solid obtained is repeated in step (2), and the target product is obtained by secondary distillation after centrifugation.

Compared with the prior art, the process design of this method is more reasonable, the preparation conditions are simple and safe, and the preparation method of p-terphenyl with high purity can be obtained.

The second is the nitridation, reduction and acetylation of biphenyl, which is used to produce p-acetylaminobiphenyl, and then react with nitrogen trioxide to obtain N-nitrite. Acetaminobiphenyl, then with benzene. This method has long process route, complicated operation, low yield (only 8%), high cost, low product quality and serious equipment corrosion.

The third kind: separation from biphenyl. The by-products of biphenyl production include p-diphenyl benzene, o-diphenyl benzene, m-diphenyl benzene, m-triphenyl benzene and some other biphenyls. According to their different melting points, boiling points and solubility, they can be prepared by sublimation and washing.

► Environmental Impact

While p-terphenyl has numerous beneficial applications, its release into the environment can pose potential risks. As an aromatic hydrocarbon, p-terphenyl is relatively persistent and can accumulate in soil and water bodies. Studies have shown that p-terphenyl can exhibit toxic effects on aquatic organisms, including fish and invertebrates, at high concentrations.

To mitigate the environmental impact of p-terphenyl, it is essential to implement proper waste management practices and minimize its release into the environment. This includes the use of containment systems in industrial processes, the treatment of wastewater before discharge, and the safe disposal of p-terphenyl-containing materials.

► Safety Precautions

P-terphenyl is classified as a combustible solid and can pose fire hazards if not handled properly. It is also an irritant to the eyes, skin, and respiratory system, and prolonged exposure can cause adverse health effects. Therefore, it is crucial to follow safety precautions when working with p-terphenyl, including the use of personal protective equipment (PPE) such as gloves, goggles, and respirators.

In addition, p-terphenyl should be stored in a cool, dry, and well-ventilated area away from sources of heat and ignition. It should also be kept separate from oxidizing agents and other incompatible materials to prevent hazardous reactions. In the event of a spill or release, appropriate cleanup procedures should be followed to minimize exposure and environmental contamination.

● Advancements in Superconductivity Research

The discovery of high-temperature superconductivity in potassium-doped p-terphenyl has opened up new avenues for research in this field. Future studies will focus on elucidating the underlying superconducting mechanism, optimizing the doping process, and exploring the effects of different dopants on the superconducting properties of p-terphenyl-based materials. Additionally, researchers will investigate the potential for achieving room-temperature superconductivity by modifying the chemical structure of p-terphenyl or developing new doping strategies.

● Development of Novel Pharmaceuticals

The biological activities of p-terphenyl and its derivatives offer exciting opportunities for drug development. Future research will aim to identify and synthesize new p-terphenyl analogs with enhanced anticancer, antimicrobial, and anti-inflammatory properties. This will involve the use of advanced synthetic techniques, such as combinatorial chemistry and high-throughput screening, to rapidly generate and evaluate large libraries of compounds. Furthermore, studies will focus on understanding the molecular mechanisms underlying the biological activities of p-terphenyl derivatives to guide the rational design of more effective drugs.

● Sustainable Production and Applications

As environmental concerns continue to grow, there is a pressing need to develop sustainable methods for producing and using p-terphenyl. This includes the exploration of renewable feedstocks for p-terphenyl synthesis, the optimization of industrial processes to reduce energy consumption and waste generation, and the development of eco-friendly applications for p-terphenyl and its derivatives. By adopting a sustainable approach, the scientific and industrial communities can ensure the long-term viability of p-terphenyl-based technologies while minimizing their environmental impact.

P-terphenyl is a remarkable aromatic compound with a wide range of applications across multiple scientific and technological domains. From its role as a high-temperature organic superconductor to its uses in medical research and industrial processes, p-terphenyl continues to demonstrate its versatility and potential. As research in this field progresses, we can expect to see new breakthroughs and innovations that will further expand the applications of p-terphenyl and contribute to the advancement of science and technology. However, it is essential to address the environmental and safety concerns associated with p-terphenyl to ensure its sustainable and responsible use in the future.

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