2088-87-1

Basic information

• Product Name: naphthalene-1,2-dicarboxylic acid
• Synonyms: 1,2-naphthalenedicarboxylic acid;Naphthalene-1,2-dicarboxylic acid dimethyl ester
• CAS NO: 2088-87-1
• Molecular Formula: C₁₂H₈O₄
• Molecular Weight: 216.1895
• EINECS: 218-233-3
• Mol File: 2088-87-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 177 °C
• Boiling Point: 441.6°Cat760mmHg
• Flash Point: 235°C
• Appearance: /
• Density: 1.454g/cm³
• Vapor Pressure: 1.41E-08mmHg at 25°C
• Refractive Index: 1.708
• PKA: 3.11±0.10(Predicted)
• CAS DataBase Reference: naphthalene-1,2-dicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: naphthalene-1,2-dicarboxylic acid(2088-87-1)
• EPA Substance Registry System: naphthalene-1,2-dicarboxylic acid(2088-87-1)

Safety Data

• Hazardous Substances Data: 2088-87-1(Hazardous Substances Data)

Usage

General Description

Naphthalene-1,2-dicarboxylic acid, also known as phthalic acid, is a white crystalline solid that is used as a precursor in the production of phthalic anhydride, which is a key ingredient in the production of plasticizers for PVC. It is also used in the synthesis of dyes, perfumes, and pharmaceuticals. Phthalic acid has a wide range of applications in the chemical industry, and its production and use are tightly regulated due to health and environmental concerns. It is considered a potential human carcinogen and may cause irritation to the skin, eyes, and respiratory tract. Additionally, phthalic acid can persist in the environment and has the potential to bioaccumulate in organisms. Therefore, proper handling and disposal of this chemical is crucial to prevent negative impacts on human health and the environment.

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 
• 573-22-8 3,4-dihydro-2H-phenanthren-1-one 
• 100538-41-8 (1-acetyl-[2]naphthyl)-glyoxylic acid 
• 7722-84-1 dihydrogen peroxide 
• 859072-08-5 (2-acetyl-[1]naphthyl)-glyoxylic acid 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 108-31-6 maleic anhydride 
• 100-42-5 styrene 
• 7553-56-2 iodine 
• 123-31-9 hydroquinone 
• 85-01-8 phenanthrene 
• 573-98-8 dimethyl-1,2 naphtalene 

Downstream Products

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

Relevant articles and documents

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.

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.

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.