ChemicalBook > Product Catalog > Chemical Reagents > Organic reagents > Aromatic acids > Phthalic acid
Phthalic acid Chemical Properties
- Melting point:210-211 °C (dec.)(lit.)
- Boiling point:214.32°C (rough estimate)
- Density 1.593
- vapor pressure 7.8 hPa (191 °C)
- refractive index 1.5100 (estimate)
- Flash point:168 °C
- storage temp. Store below +30°C.
- solubility methanol: 0.1 g/mL, clear
- pka2.89(at 25℃)
- form Powder
- color White
- PH2 (5g/l, H2O, 20℃)
- Water Solubility 7 g/L (25 ºC)
- Merck 14,7371
- BRN 608199
- Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
- CAS DataBase Reference88-99-3(CAS DataBase Reference)
- NIST Chemistry Reference1,2-Benzenedicarboxylic acid(88-99-3)
- EPA Substance Registry SystemPhthalic acid (88-99-3)
Phthalic acid Usage And Synthesis
- DescriptionPhthalic acid is an aromatic dicarboxylic acid, with formula C6H4(CO2H)2. It is an isomer of isophthalic acid and terephthalic acid. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale.
- Chemical PropertiesPHTHALIC ACID,C6H4(COOH)2, mp 208 °C (ortho), 330 °C (meta and iso), the ortho form sublimes and the meta and iso forms decompose with heat, sp gr 1.593 (ortho). Phthalic acid is very slightly soluble in H2O, soluble in alcohol, and slightly soluble in ether. The solid form is colorless, crystalline
- UsesIt is a dibasic acid, with pKa's of 2.89 and 5.51. The mono potassium salt, potassium hydrogen phthalate is a standard acid in analytical chemistry. Typically phthalate esters are prepared from the widely available phthalic anhydride. Reduction of phthalic acid with sodium amalgam in the presence of water gives the 1,3- cyclohexadiene derivative.
- UsesOrganic reagent used to synthesize phthalates.
- DefinitionChEBI: A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions.
- Definitionphthalic acid: colourlesscrystalline dicarboxylic acid,C6H4(COOH)2; r.d. 1.6; m.p. 207°C.The two –COOH groups are substitutedon adjacent carbon atoms ofthe ring, the technical name beingbenzene-1,2-dicarboxylic acid. Theacid is made from phthalic anhydride(benzene-1,2-dicarboxylic anhydride,C8H4O3), which is made by the catalyticoxidation of naphthalene. Theanhydride is used in making plasticizersand polyester resins.
- Production MethodsPhthalic acid is produced by the catalytic oxidation of naphthalene directly to phthalic anhydride and a subsequent hydrolysis of the anhydride.
Phthalic acid was first obtained by French chemist Auguste Laurent in 1836 by oxidizing naphthalene tetrachloride. Believing the resulting substance to be a naphthalene derivative, he named it "naphthalic acid". After the Swiss chemist Jean Charles Galissard de Marignac determined its correct formula, Laurent gave it its present name. Manufacturing methods in the nineteenth century included oxidation of naphthalene tetrachloride with nitric acid, or, better, oxidation of the hydrocarbon with fuming sulfuric acid, using mercury or mercury(II) sulfate as a catalyst.
- Synthesis Reference(s)The Journal of Organic Chemistry, 30, p. 2414, 1965 DOI: 10.1021/jo01018a074
- General DescriptionWhite crystals or fine white powder.
- Air & Water ReactionsInsoluble in water.
- Reactivity ProfilePhthalic acid is a carboxylic acid. Phthalic acid is sensitive to exposure to extreme heat. Phthalic acid reacts violently with nitric acid. Phthalic acid is incompatible with sodium nitrite. Phthalic acid is also incompatible with oxidizers. .
- Fire HazardPhthalic acid is combustible.
- Safety ProfileModerately toxic by ingestion and intraperitoneal routes. A skin and mucous membrane irritant. Combustible when heated. In the form of dust (anhydride) it can explode. Mixtures with sodmm nitrite explode when heated. Violent reaction with HNO3. When heated to decomposition it emits acrid smoke and irritating fumes. Used in synthesis of dyes and dyestuffs, in medcines and perfumes.
- SafetyThe toxicity of phthalic acid is low with LD50 (mouse) of 550 mg/kg. However, many phthalate esters have been implicated as endocrine disruptors.
- Purification MethodsCrystallise phthalic acid from water. [Beilstein 9 IV 3167.]
- IsomersPhthalic acid is one of three isomers of benzene dicarboxylic acid, the others being iso phthalic acid and terephthalic acid. Sometimes the term "phthalic acids" is used to refer to this family of isomers, but in the singular, "phthalic acid", refers exclusively to the ortho- isomer.
Phthalic acid Preparation Products And Raw materials
- Preparation ProductsBenzoic acidBis(2-ethylhexyl) phthalateTetramethrin4-AminopyridineOxendolone(4S)-HYDROXY-3-METHYL-2-(2-PROPENYL)-2-CYCLOPENTENE-1-ONEPhosmetDimethyl phthalatecomplex polystyrene high efficiency anticorrosion paintDI-N-OCTYL PHTHALATEPhthalonitrilecis-1,2-DiaminocyclohexaneMERBROMIN
- Raw materialsNitric acidAmmonium hydroxidePhthalic anhydride
- Maleic acid Acrylic acid Phthalic acid methyl ester Benzyl butyl phthalate Diallyl ester of phthalic acid,Diallyl ester o-phthalic acid,Diallylester phthalic acid Diethyl phthalate Bis(2-methoxyethyl) phthalate DI-N-HEXYL PHTHALATE DIPHENYL PHTHALATE DI-N-PENTYL PHTHALATE-D4 Dinonyl phthalate Dicyclohexyl phthalate BIS(2-ETHOXYETHYL)PHTHALATE BIS(2-N-BUTOXYETHYL)PHTHALATE BIS(4-METHYL-2-PENTYL)PHTHALATE Phthalic acid, 3-nitro- 4-[(phenylsulphonyl)oxy]phthalic acid Phthalic acid
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