2088-87-1

Usage

Uses

Used in Chemical Industry:
Naphthalene-1,2-dicarboxylic acid is used as a precursor for the production of phthalic anhydride, which is essential in the manufacturing of plasticizers for PVC. These plasticizers enhance the flexibility and durability of PVC materials, making them suitable for a wide range of applications, including pipes, films, and medical devices.
Used in Dye and Perfume Production:
Naphthalene-1,2-dicarboxylic acid is utilized as a key intermediate in the synthesis of various dyes and perfumes. Its unique chemical structure allows for the creation of a diverse range of colorants and fragrances, contributing to the vibrancy and variety of products in these industries.
Used in Pharmaceutical Synthesis:
As a versatile chemical intermediate, naphthalene-1,2-dicarboxylic acid is employed in the synthesis of various pharmaceutical compounds. Its ability to form stable derivatives and participate in complex chemical reactions makes it a valuable component in the development of new drugs and medications.
Used in Environmental and Health Regulations:
Due to its potential carcinogenic properties and the risk of environmental persistence and bioaccumulation, naphthalene-1,2-dicboxylic acid is subject to strict regulations and guidelines for its production, use, and disposal. These regulations aim to minimize the exposure of humans and the environment to this chemical, ensuring the safety and well-being of both.

InChI:InChI=1/C12H8O4/c13-11(14)9-6-5-7-3-1-2-4-8(7)10(9)12(15)16/h1-6H,(H,13,14)(H,15,16)

Upstream product

• 56-23-5 tetrachloromethane 
• 38512-20-8 2-naphthoic peroxyanhydride 
• 825-44-5 benzothiophene-1,1-dioxide 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 19291-76-0 1,2-dicyanonaphthalene 
• 573-22-8 3,4-dihydro-2H-phenanthren-1-one 
• 85-01-8 phenanthrene 
• 108-31-6 maleic anhydride 
• 100-42-5 styrene 
• 7553-56-2 iodine 
• 123-31-9 hydroquinone 
• 100538-41-8 (1-acetyl-[2]naphthyl)-glyoxylic acid 
• 7722-84-1 dihydrogen peroxide 
• 859072-08-5 (2-acetyl-[1]naphthyl)-glyoxylic acid 

Downstream Products

• 10060-32-9 dimethyl 1,2-naphthalenedicarboxylate 
• 130728-71-1 2-phenyl-1H-benzo[e]isoindole-1,3(2H)-dione 

Relevant academic research and scientific papers

Photochemical oxidation of phenanthrene sorbed on silica gel

There have been relatively few detailed studies of PAH photochemical degradation mechanisms and products at solid/air interfaces under controlled conditions. Results from mechanistic studies on particulate simulants are important in understanding the fates of PAH sorbed on similar materials in natural settings. In this study, the photolysis of phenanthrene (PH) on silica gel, in the presence of air, has been carefully examined. Once sorbed onto the silica surface, PH is not observed to repartition into the gas phase, even under vacuum, and dark reactions of PH are not observed at the silica/air interface. Photolysis (254 nm) of PH leads to the formation of 2,2'-biformylbiphenyl (1), 9,10-phenanthrenequinone (2), cis-9,10-dihydrodihydroxyphenanthrene (3), benzocoumarin (4), 2,2'-biphenyldicarboxylic acid (5), 2-formyl-2'-biphenylcarboxylic acid (5), 2-formylbiphenyl (7),1,2-naphthalenedicarboxylic acid (8), and phthalic acid (9). These products account for 85-90% of the reacted PH. The photoproducts are independent of excitation wavelength (254 and 350 nm), and the reaction proceeds entirely through an initial step involving the addition of singlet molecular oxygen to the ground state of phenanthrene with subsequent thermal and/or photochemical reactions of the initially formed product. Singlet molecular oxygen is produced through quenching of the lowest triplet state of PH at the silica gel/air interface. The high material balance and detailed mechanistic information provided by this study serve as a standard for comparisons with the products and mechanism of PH photochemical oxidation on environmentally derived inorganic oxide particulates.

Selective deprotection of phthalyl protected amines

Phthalyl amidase selectively deprotects phthalimido groups under very mild aqueous conditions in a one-pot reaction to produce phthalic acid and the free amine. The enzyme has been shown to deprotect several primary amines of distinctly different structure, and exhibits chiral selectivity when the substrate contains extensive β-branching. The enzyme has a definite requirement for ortho positioning of the functional groups on a fixed axis of rotation.

Superoxide Oxidation: A Novel Route to Aromatic 1,2-Dicarboxylic Acids

Potassium superoxide in aprotic media, in the presence of 18-crown-6 ether, effects a novel and mild oxidative cleavage of quinones, cyclic alcohols, and ketones fused to various aromatic hydrocarbons.Aromatic 1,2-dicarboxylic acids are obtained as major products, with highest yields in dimethylformamide, under oxygen or air.For example, the yield of pyrene-1,2-dicarboxylic acid is 82percent from 9,10-dihydrobenzopyren-7(8H)-one and 88percent from benzopyrene-7,8-dione.Minor side products include aromatic tetrones and 3-(2-carboxyaryl)propionic or 3-(2-carboxyaryl)propenoic acid, which provide mechanistic insights.

The Zinc(II)-Catalyzed Henkel Reaction of Dipotassium 1,8-Naphthalenedicarboxylate in a Dispersion Medium

The Henkel reaction of dipotassium 1,8-naphthalenedicarboxylate in naphthalene as a dispersion medium gave dipotassium 2,6-naphthalenedicarboxylate (1) in a higher yield and with a better reproducibility than the reaction without a dispersion medium.Catalysts, particularly zinc catalysts, were examined in detail.The anion moiety of zinc catalysts affected the reaction, and the halide anion was effective for the selective formation of 1.The addition of potassium halide to the zinc catalysts also increased the yield of 1.The catalytic activity of the halide anion increased in the order: Cl---.The activity of the zinc catalysts was also compared with that of cadmium catalysts.

Method for the preparation of 2,6-naphthalene dicarboxylic acid

Disclosed is a method for the preparation of 2,6-naphthalene dicarboxylic acid from 2-acyl-6-alkyl naphthalene, especially 2-acetyl-6-methylnaphthalene, by oxidation in two steps with oxygen or air. The catalyst in the first oxidation is based on manganese. The catalyst in the second oxidation is based on cobalt with bromine added. The addition of 6-alkyl-2-naphthoic acid to the reaction in the second oxidation, in portions or in a continuous manner, results in very good yields having high purities.