Phthalic acid
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| Phthalic acid | |
|---|---|
| Image:Phthalic-acid-2D-skeletal.png | |
| Image:Phthalic acid-3d.png | |
| Other names | Benzene-1,2- dicarboxylic acid |
| Identifiers | |
| CAS number | |
| EINECS number | |
| SMILES | C1=CC=C(C(=C1) C(=O)O)C(=O)O |
| Properties | |
| Molecular formula | C6H4(COOH)2 |
| Molar mass | 166.14 g/mol |
| Appearance | white solid |
| Density | 1.593 g/cm3, solid |
| Melting point |
210 °C decomp. |
| Solubility in water | Slightly soluble |
| Hazards | |
| EU classification | not listed |
| NFPA 704 |
|
| Related Compounds | |
| Related carboxylic acids | Isophthalic acid Terephthalic acid |
| Related compounds | Phthalic anhydride Phthalimide Phthalhydrazide Phthaloyl chloride Benzene-1,2- dicarboxaldehyde |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Phthalic acid (IUPAC systematic name: benzene-1,2-dicarboxylic acid) is an aromatic dicarboxylic acid, with formula C6H4(COOH)2. It is an isomer of isophthalic acid and terephthalic acid.
Contents |
Uses
Phthalic acid is used mainly in the form of the anhydride to produce other chemicals such as dyes, perfumes, saccharin, phthalates and many others.
History
Phthalic acid was obtained by French chemist Auguste Laurent in 1836 by oxidizing naphthalene tetrachloride, and, believing the resulting substance to be a naphthalene derivative, he named it naphthalenic acid. Swiss chemist Jean Charles Galissard de Marignac determined its formula and showed Laurent’s supposition to be incorrect, upon which Laurent gave it its present name. Manufacturing methods in the nineteenth century included oxidation of naphthalene tetrachloride (prepared from naphthalene, potassium chlorate and hydrochloric acid) with nitric acid, or, better, oxidation of the hydrocarbon with fuming sulfuric acid, using mercury or mercury(II) sulfate as a catalyst.
The catalytic oxidation of naphtalene directly to phthalic anhydride and a subsequent hydrolysis of the anhydride is one of the new production methods.
Chemistry
It forms white crystals, melting at 210 °C with decomposition into water and phthalic anhydride. Heating with an excess of lime produces benzene. The acid (and anhydride) are largely used in the color industry (see phenolphthalein).
See also
References
None.
External links
This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain.de:Phthalsäurelv:Ftalskābe hu:Ftálsav nl:Ftaalzuur ja:フタル酸fi:Ftaalihappo
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
