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2,6-Naphthalenedicarboxylic acid, CAS 1141-38-4.It appears as a white to pale yellowish-white crystalline powder with a melting point of approximately 310–313 °C (decomposition). It is stable at room temperature, practically insoluble in water, benzene and toluene, and slightly soluble in common organic solvents. Featuring a symmetrical and rigid molecular structure, it is the most industrially valuable isomer of naphthalenedicarboxylic acid.Its primary application is as a key monomer for high-performance polyester PEN (polyethylene naphthalate).
It is also used in the synthesis of liquid crystal polymers, polyurethanes, pharmaceutical intermediates, dyes and metal-organic framework materials. It is mainly prepared by oxidation of 2,6-dialkylnaphthalene and the Henkel carboxyl transfer reaction, and was first obtained via hydrolysis of 2,6-dicyanonaphthalene in 1876.
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Chemical Formula |
C12H8O4 |
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Exact Mass |
216 |
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Molecular Weight |
216 |
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m/z |
216 (100.0%), 217 (13.0%) |
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Elemental Analysis |
C, 66.67; H, 3.73; O, 29.60 |
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2,6-Naphthalenedicarboxylic acid is also known as 2,6-Naphthalenedioic acid, is an important organic compound with a wide range of industrial applications.
Application in the field of polymer materials
It is an important raw material for manufacturing high-strength and excellent dyeing performance polyester fibers. Polyester fiber is a synthetic fiber with excellent wear resistance, wrinkle resistance, and elasticity, and is widely used in textile, clothing, home decoration, and other fields. Through the reaction of raw materials such as ethylene glycol, polyester fibers with specific properties can be synthesized to meet the needs of different fields.
Example: A textile enterprise used it as the main raw material to synthesize high-strength and high elasticity polyester fibers through polymerization reaction. This fiber is used to manufacture products such as sportswear and outdoor equipment that require high tensile strength and wear resistance, improving the comfort and durability of the products.
F-grade insulation material is a high-temperature insulation material with excellent heat resistance and electrical insulation properties, widely used in insulation components of electrical and electronic equipment. It can be used as one of the important raw materials for manufacturing F-grade insulation materials, synthesizing insulation materials with specific properties through reactions with other raw materials.
Example: A certain electrical enterprise used it as the main raw material and manufactured F-grade insulation material through specific polymerization and processing techniques. This material is used to manufacture insulation components for electrical equipment such as high-voltage motors and transformers, improving the reliability and safety of the equipment.
Liquid crystal polymer is a polymer material with special liquid crystal properties, which has excellent heat resistance, high strength, and processability, and is widely used in fields such as electronics, electrical engineering, aerospace, etc. It can be used as one of the important monomers for manufacturing liquid crystal polymers, synthesizing liquid crystal polymers with specific properties through copolymerization reactions with other monomers.
Example: An electronics company used it as one of the main monomers to synthesize liquid crystal polymers through copolymerization reaction. This polymer is used to manufacture electronic components such as flexible circuit boards and high-frequency connectors, improving the reliability and performance of the products.
Applications in the fields of pharmaceuticals and fine chemicals
It can be used as one of the important raw materials for manufacturing pharmaceutical intermediates. Pharmaceutical intermediates are key compounds in the process of synthesizing drugs, with specific chemical structures and biological activities. By reacting with other compounds, pharmaceutical intermediates with specific biological activities can be synthesized, providing key raw materials for drug synthesis.
Example: A pharmaceutical company used it as one of the main raw materials to synthesize a certain antibacterial pharmaceutical intermediate through a specific chemical reaction. This intermediate is used to synthesize drugs for the treatment of bacterial infections, providing effective drug options for the treatment of patients.
It can also be used as one of the important raw materials for manufacturing fine chemicals. Fine chemicals are chemicals with specific functions and uses, widely used in fields such as coatings, inks, dyes, fragrances, etc. By reacting with other compounds, fine chemicals with specific properties and applications can be synthesized.
Example: A certain fine chemical enterprise used it as one of the main raw materials to synthesize a high-performance coating additive through specific chemical reactions. This additive is used to improve the adhesion and weather resistance of coatings, providing critical support for enhancing the performance of coating products.
Applications in other fields
2,6-Naphthalenedicarboxylic acid and its derivatives also have a wide range of applications in the fields of dye and pigment manufacturing. Through specific chemical reactions, it can be converted into dyes or pigments with specific colors and properties, used in fields such as textiles, printing, plastics, etc.
Example: A dye company used it as one of the main raw materials to synthesize a high-performance dispersed dye through a specific chemical reaction. This dye is used to dye synthetic fibers such as polyester and nylon, improving the brightness and fastness of the dyed products.
2. Manufacturing optoelectronic materials
This product and its derivatives also have potential application value in the field of optoelectronic materials. Through specific synthesis and modification methods, it can be transformed into materials with specific optoelectronic properties, which can be used to manufacture optoelectronic devices such as organic light-emitting diodes (OLEDs) and solar cells.
Example: A certain optoelectronic material research institution is conducting research on the synthesis of high-performance optoelectronic materials using it and its derivatives. They hope to improve the optoelectronic properties and stability of materials by optimizing synthesis methods and modification techniques, providing new material choices for the manufacturing of optoelectronic devices.
3. Manufacturing other polymer materials
In addition to the above applications, it can also be used as an important raw material for manufacturing other polymer materials. For example, it can react with diols to synthesize polyether ester elastomers, which have excellent elasticity and wear resistance and are widely used in fields such as shoe soles and seals. In addition, it can also be used to synthesize other types of polymer materials, such as polyimide, polyamide, etc.
Example: A polymer material company used it as one of the main raw materials to synthesize polyether ester elastomers through specific polymerization reactions. This type of elastomer is used to manufacture products such as sports shoe soles and automotive seals, improving the comfort and durability of the products.
Application case analysis
Example 1: Manufacturing polyethylene naphthalate (PEN)
Polyethylene terephthalate (PEN) is a high-performance polyester material with excellent heat resistance, chemical corrosion resistance, and gas barrier properties. PEN can be synthesized through its condensation reaction with it. PEN is widely used in fields such as magnetic tape, advanced photo systems, packaging films, and tires.
(1) Magnetic tape: PEN, as a magnetic tape substrate, has excellent wear resistance and chemical corrosion resistance, ensuring the stability and durability of the magnetic tape.
(2) Advanced photo system: PEN, as a photo substrate, has excellent optical and gas barrier properties, which can protect photos from the effects of light and oxygen, and extend the shelf life of photos.
(3) Packaging film: PEN, as a packaging film material, has excellent heat resistance and gas barrier properties, which can protect food from the effects of oxygen, moisture, etc., and extend the shelf life of food.
(4) Tire: PEN, as a tire cord material, has excellent strength and wear resistance, which can improve the durability and safety of tires.
Example 2: Manufacturing Liquid Crystal Polymers (LCP)
Liquid crystal polymer (LCP) is a polymer material with special liquid crystal properties, excellent heat resistance, high strength, and processability. LCP can be synthesized through the copolymerization reaction of 2,6-naphthalenedicarboxylic acid with other monomers. LCP is widely used in fields such as electronics, electrical, aerospace, etc.
(1) In the field of electronics, LCP, as a flexible circuit board material, has excellent heat resistance and processability, which can meet the needs of miniaturization and lightweighting of electronic products.
(2) Electrical field: LCP, as a high-frequency connector material, has excellent electrical performance and heat resistance, which can ensure the stability and reliability of electrical connections.
(3) Aerospace field: LCP, as a material for aerospace components, has excellent strength and heat resistance, which can meet the high requirements for material performance in the aerospace field.
Example 3: Manufacturing pharmaceutical intermediates
It can be used as one of the important raw materials for manufacturing pharmaceutical intermediates. Through specific chemical reactions, it can be converted into pharmaceutical intermediates with specific biological activities, providing key raw materials for drug synthesis.
(1) Antibacterial drugs: The synthetic pharmaceutical intermediates can be used to synthesize drugs with antibacterial activity, providing effective drug options for the treatment of bacterial infections.
(2) Antitumor drugs: The synthesized pharmaceutical intermediates can also be used to synthesize drugs with anti-tumor activity, providing new hope for the treatment of cancer patients.
High-performance liquid chromatography (HPLC) is the standard method for the determination of 2,6-NDA content.Sample pretreatment: Dry the sample to constant weight at 110 °C, accurately weigh 0.001 g, dissolve it in 0.1 mol/L NaOH solution, and dilute to 100 mL.Chromatographic conditions: ACQUITY UPLC BEH C18 column (1.7 μm, 2.1 × 100 mm) at 40 °C; mobile phase of acetonitrile / 0.001% formic acid aqueous solution (53:47, V/V) with a gradient flow rate of 0.82–0.90 mL/min; fluorescence detector (excitation at 210 nm), injection volume 20 μL.Quantitation: Calculated by external standard method. The content of 2,6-NDA shall be ≥ 99.5% for superior grade and ≥ 98.0% for first grade. This method features high resolution and good repeatability with a relative standard deviation < 0.05%, enabling accurate differentiation of isomers and monocarboxylic intermediates.
Moisture: Determined by Karl Fischer method (GB/T 6283). Moisture content ≤ 0.05% for superior grade and ≤ 0.1% for first grade to avoid polymerization side reactions caused by moisture.Residue on ignition: The sample is ignited at 750 °C, and the residual inorganic matter is weighed, with the residue controlled ≤ 15 mg/kg, reflecting the level of metal salt impurities.Heavy metals: Fe, Ni, Pb, etc., are determined by atomic absorption spectrometry (AAS). Fe ≤ 5 mg/kg and Ni ≤ 2 mg/kg to prevent catalytic degradation of polymers by metal ions.Melting point: Measured by capillary method. The melting range of pure product is 310–313 °C; a widened melting range indicates reduced purity.Colority: HunterLab b-value measured by colorimeter, ≤ 5 for superior grade, indicating the content of yellowish impurities.
All tests shall be performed in duplicate, with the average value reported and relative deviation ≤ 5%. The purity of reference standards is ≥ 99.9%, and reagents are of chromatographic or guaranteed grade. Instruments are calibrated regularly (HPLC wavelength/flow rate, AAS light source, titratable concentration of Karl Fischer titrator). System suitability requirements: theoretical plate number > 5000, resolution > 2.0, tailing factor 0.95–1.05.
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