関: phthalate

WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/06/04 17:09:45」(JST)

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Phthalic 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.^[5]

Production[edit]

Phthalic acid is produced by the catalytic oxidation of naphthalene directly to phthalic anhydride and a subsequent hydrolysis of the anhydride.^[5]

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".^[6] After the Swiss chemist Jean Charles Galissard de Marignac determined its correct formula,^[7] Laurent gave it its present name.^[8] 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.

Reactions and uses[edit]

Phthalic acid crystals

It is a dibasic acid, with pK_a's of 2.89 and 5.51. The monopotassium 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.^[9]

Isomers[edit]

Phthalic acid is one of three isomers of benzenedicarboxylic acid, the others being isophthalic 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	isophthalic acid	terephthalic acid
(ortho-phthalic acid)	(meta-phthalic acid)	(para-phthalic acid)

Safety[edit]

The toxicity of phthalic acid is low with LD₅₀ (mouse) of 550 mg/kg. However, many phthalate esters have been implicated as endocrine disruptors.

References[edit]

^ Several melting points are reported, for example: (i) 210−211 °C with decomposition (Sigma-Aldrich on-line), (ii) 191 °C in a sealed tube (Ullmann's Encyclopedia of Industrial Chemistry), (iii) 230 °C with conversion to phthalic anhydride and water (J.T.Baker MSDS).
^ http://hazard.com/msds/mf/baker/baker/files/p4270.htm
^ http://actrav.itcilo.org/actrav-english/telearn/osh/ic/88993.htm
^ Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., Determination of Organic Structures by Physical Methods, Academic Press, New York, 1955.
^ ^a ^b Peter M. Lorz, Friedrich K. Towae, Walter Enke, Rudolf Jäckh, Naresh Bhargava, Wolfgang Hillesheim “Phthalic Acid and Derivatives” in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a20_181.pub2
^ See:
- Auguste Laurent (1836) "Sur l'acide naphtalique et ses combinaisons" (On naphthalic acid and its compounds), Annales de Chimie et de Physique, 61 : 113-125. (Note: The empirical formulae of the compounds that were analyzed in this article are incorrect, in part because, during this period, chemists used incorrect atomic masses for carbon (6 instead of 12) and other elements.)
- Reprinted in German as: Auguste Laurent (1836) "Ueber Naphthalinsäure und ihre Verbindungen" (On naphthalenic acid and its compounds), Annalen der Pharmacie, 19 (1) : 38-50; for the preparation of phthalic acid, see page 41.
^ C. de Marignac (1841) "Ueber die Naphtalinsäure und ein bei ihrer Darstellung entstehendes flüchtiges Produkt" (On naphthalinic acid and a volitile product that arises during its preparation), Annalen der Chemie und Pharmacie, 38 (1) : 13-20. (Note: Again, Marignac's empirical formulae are wrong because chemists at this time used incorrect atomic masses.)
^ See:
- Auguste Laurent (1841) "Sur de nouvelles combinaisons nitrogénées de la naphtaline et sur les acides phtalique et nitrophtalique" (On new nitrogenous compounds of naphthalene, and on phthalic acid and nitrophthalic acid), Revue Scientifique et Industrielle, 6 : 76-99; on page 92, Laurent coins the name "acide phtalique" (phthalic acid) and admits that his earlier empirical formula for phthalic acid was wrong.
- Reprinted in German as: Auguste Laurent (1842) "Ueber neue stickstoffhaltige Verbindungen des Naphtalins, über Phtalinsäure und Nitrophtalinsäure" (On new nitrogenous compounds of naphthalene, on phthalic acid and nitrophthalic acid), Annalen der Chemie und Pharmacie, 41 (1) : 98-114; on page 108, Laurent coins the name "Phtalinsäure" (phthalic acid).
^ Richard N. McDonald and Charles E. Reineke (1988), "trans-1,2-Dihydrophthalic Acid", Org. Synth. ; Coll. Vol. 6: 461

Merck Index, 9th ed, #7178

External links[edit]

International Chemical Safety Card 0768

This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press.

UpToDate Contents

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English Journal

Biotin-streptavidin-amplified real-time immune-PCR assay for detecting dimethyl phthalate in beverage and drinking water samples.

Sun R1, Zhuang H.
Analytical and bioanalytical chemistry.Anal Bioanal Chem.2015 Feb;407(4):1261-5. doi: 10.1007/s00216-014-8329-z. Epub 2014 Nov 23.
Dimethyl phthalate (DMP), one family of the phthalic acid diesters (PAEs), is an increasing widely used plasticizer. A sensitive and high-throughput direct competitive biotin-streptavidin-amplified system based on real-time immune-PCR (BA-rt-IPCR) techniques was developed for detecting DMP in bevera
PMID 25417132

Magnetic solid-phase extraction based on modified magnetic nanoparticles for the determination of phthalate diesters in water samples.

Zare Jeddi M1, Ahmadkhaniha R2, Yunesian M3, Rastkari N4.
Journal of chromatographic science.J Chromatogr Sci.2015 Feb;53(2):385-91. doi: 10.1093/chromsci/bmu058. Epub 2014 Jun 25.
A method was developed for the extraction of phthalic acid esters (PAEs) from bottled water. Surface-functionalized magnetic particles (MPs) were used as adsorbent of magnetic solid-phase extraction (MSPE). The MPs were prepared by using both polydimethylsiloxane and multiwalled carbon nanotubes. By
PMID 24965039

Adsorption and removal of phthalic acid and diethyl phthalate from water with zeolitic imidazolate and metal-organic frameworks.

Khan NA1, Jung BK1, Hasan Z1, Jhung SH2.
Journal of hazardous materials.J Hazard Mater.2015 Jan 23;282:194-200. doi: 10.1016/j.jhazmat.2014.03.047. Epub 2014 Mar 31.
ZIF-8 (zinc-methylimidazolate framework-8), one of the zeolitic imidazolate frameworks (ZIFs), has been used for the removal of phthalic acid (H2-PA) and diethyl phthalate (DEP) from aqueous solutions via adsorption. The adsorption capacity of the ZIF-8 for H2-PA was much higher than that of a comme
PMID 24726184

Japanese Journal

VOCデニューダーによる室内空気中フタル酸エステル類のガス・粒子態の分離測定に関する検討

アブラトメリキザット,藤井修二,鍵直樹
室内環境 16(1), 3-13, 2013
フタル酸エステル（PAE）は準揮発性有機化合物（SVOC）の代表的な物質であり，蒸気圧が低いため空気中ではガス相と粒子相の両相に存在する可能性が指摘されている。そこで本研究では，室内空気中においてSVOCのガス・粒子態を分離するために，VOCデニューダーを上流に，石英ガラス繊維フィルター1枚を下流に用いたデニューダーフィルター捕集法（D-F捕集法）の適用性について検討した。まず，ガス・粒子態のVO …
NAID 130003376497

Seasonal variations of water-soluble organic carbon, dicarboxylic acids, ketocarboxylic acids, and α-dicarbonyls in Central Himalayan aerosols

Hegde P.,Kawamura K.
Atmospheric Chemistry and Physics 12(14), 6645-6665, 2012-07-26
… Molecular distributions of diacids revealed that oxalic (C2) acid was the most abundant species followed by succinic (C4) and malonic (C3) acids. … Phthalic acid, which originates from oxidation of polycyclic aromatic hydrocarbons such as naphthalene, was found to be 7 times higher in summer than winter. …
NAID 120004689047

Stable carbon isotopic compositions of total carbon, dicarboxylic acids and glyoxylic acid in the tropical Indian aerosols : Implications for sources and photochemical processing of organic aerosols

Pavuluri Chandra Mouli,Kawamura Kimitaka,Swaminathan T.,Tachibana Eri
Journal of Geophysical Research, Atmospheres 116, D18307, 2011-09-29
… 80.17°E) were studied for stable carbon isotopic compositions (δ13C) of total carbon (TC), individual dicarboxylic acids (C2-C9) and glyoxylic acid (ωC2). … Oxalic (C2) (-17.1 ± 2.5‰), malonic (C3) (-20.8 ± 1.8‰), succinic (C4) (-22.5 ± 1.5‰) and adipic (C6) (-20.6 ± 4.1‰) acids and ωC2 acid (-22.4 ± 5.5‰) were found to be more enriched with 13C compared to TC. …
NAID 120003918920

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★リンクテーブル★

リンク元	「phthalate」「フタル酸」
拡張検索	「terephthalic acid」「isophthalic acid」

「phthalate」

Phthalic acid
	IUPAC name benzene-1,2-dicarboxylic acid
	Other names benzene-1,2-dioic acid, phthalic acid, ortho-phthalic acid
Identifiers
CAS number	88-99-3
PubChem	1017
EC number	201-873-2
Jmol-3D images	Image 1
	SMILES C1=CC=C(C(=C1); C(=O)O)C(=O)O ;
Properties
Molecular formula	C8H6O4
Molar mass	166.14 g/mol
Appearance	white solid
Density	1.593 g/cm3, solid
Melting point	191−230 °C
Solubility in water	0.6 g / 100 mL
Acidity (pKa)	2.98, 5.28
Hazards
NFPA 704	0 2 0
Related compounds
Related carboxylic acids	Isophthalic acid; Terephthalic acid
Related compounds	Phthalic anhydride; Phthalimide; Phthalhydrazide; Phthaloyl chloride; Benzene-1,2-; dicarboxaldehyde
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references