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{{short description|Aromatic organic compound with formula C6H4(COOH)2}} |
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{{chembox |
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|Watchedfields = changed |
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| verifiedrevid = 414049492 |
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|verifiedrevid = 446532204 |
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| Name = Phthalic acid |
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| ImageFile = Phthalic-acid-2D-skeletal.png |
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|Name = Phthalic acid |
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|ImageFile = Phthalic-acid-2D-skeletal.png |
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| ImageSize = 150px |
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|ImageSize = 150px |
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| ImageName = Phthalic acid |
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|ImageName = Phthalic acids |
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|ImageClass = skin-invert |
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| ImageFile1 = Phthalic-acid-3D-balls.png |
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|ImageFile1 = Phthalic acid 3D ball.png |
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| ImageSize1 = 170px |
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|ImageSize1 = 170px |
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| IUPACName = phthalic acid |
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| OtherNames = benzene-1,2-dicarboxylic acid, ortho-phthalic acid |
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|ImageAlt1 = Ball-and-stick model of the phthalic acid molecule |
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|PIN = Benzene-1,2-dicarboxylic acid <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) --> |
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| Section1 = {{Chembox Identifiers |
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|OtherNames = 1,2-Benzenedioic acid<br>Phthalic acid<br>Benzene-1,2-dioic acid<br>''ortho''-Phthalic acid |
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| SMILES = C1=CC=C(C(=C1)<br />C(=O)O)C(=O)O |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| CASNo = 88-99-3 |
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|ChemSpiderID = 992 |
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| EINECS = 201-873-2 |
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|SMILES = OC(=O)c1ccccc1C(=O)O |
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| PubChem = 1017 |
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|InChI = 1/C8H6O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)(H,11,12) |
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}} |
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|InChIKey = XNGIFLGASWRNHJ-UHFFFAOYAX |
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| Section2 = {{Chembox Properties |
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|StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| Formula = C<sub>8</sub>H<sub>6</sub>O<sub>4</sub> |
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|StdInChI = 1S/C8H6O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)(H,11,12) |
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| MolarMass = 166.14 g/mol |
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|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| Appearance = white solid |
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|StdInChIKey = XNGIFLGASWRNHJ-UHFFFAOYSA-N |
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| Density = 1.593 g/cm<sup>3</sup>, solid |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| Solubility = 0.6 g / 100 mL <ref>http://hazard.com/msds/mf/baker/baker/files/p4270.htm</ref><ref>http://actrav.itcilo.org/actrav-english/telearn/osh/ic/88993.htm</ref> |
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|CASNo = 88-99-3 |
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| pKa=2.98, 5.28<ref>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.</ref> |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| MeltingPt = 191 - 230 °C<ref>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).</ref> |
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|UNII = 6O7F7IX66E |
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}} |
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|EINECS = 201-873-2 |
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| Section4 = {{Chembox Thermochemistry |
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|PubChem = 1017 |
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}} |
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|ChEBI_Ref = {{ebicite|changed|EBI}} |
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| Section7 = {{Chembox Hazards |
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| EUClass = |
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|ChEBI = 29069 |
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}} |
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| NFPA-H = 2 |
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|Section2={{Chembox Properties |
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| NFPA-F = 0 |
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|Formula = {{chem2|C8H6O4}} |
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| NFPA-R = 0 |
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|MolarMass = 166.132 g/mol |
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}} |
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|Appearance = white solid |
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| Section8 = {{Chembox Related |
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|Density = 1.593 g/cm<sup>3</sup>, solid |
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| Function = ]s |
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|Solubility = 0.6 g / 100 mL <ref>{{cite web|url=http://hazard.com/msds/mf/baker/baker/files/p4270.htm|title=PHTHALIC ACID|website=hazard.com}}</ref> |
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| OtherFunctn = ]<br />] |
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|pKa = 2.89, 5.51<ref>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.</ref> |
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| OtherCpds = ]<br />]<br />]<br />]<br />] |
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|MeltingPtC = 207 |
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}} |
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|MeltingPt_ref = <ref>Several melting points are reported, for example: (i) 480. K (NIST website), (ii) 210−211 °C with decomposition (Sigma-Aldrich on-line), (iii) 191 °C in a sealed tube (Ullmann's Encyclopedia of Industrial Chemistry), (iv) 230 °C with conversion to phthalic anhydride and water (J.T.Baker MSDS).</ref> |
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|MagSus = -83.61·10<sup>−6</sup> cm<sup>3</sup>/mol |
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|Section3={{Chembox Thermochemistry |
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|Section4={{Chembox Hazards |
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|NFPA-H = 2 |
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|NFPA-F = 0 |
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|NFPA-R = 0 |
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}} |
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|Section5={{Chembox Related |
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|OtherFunction_label = ]s |
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|OtherFunction = ]<br />] |
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|OtherCompounds = ]<br />]<br />]<br />]<br />] |
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'''Phthalic acid''' is an ] ], with formula C<sub>6</sub>H<sub>4</sub>(CO<sub>2</sub>H)<sub>2</sub>. It is an isomer of ] and ]. Although phthalic acid is of modest commercial importance, the closely related derivative ] is a commodity chemical produced on a large scale.<ref name=Ullmann>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}}</ref> |
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In ], '''phthalic acid''' is an ] ], with ] {{chem2|C6H4(CO2H)2}} and ] {{chem2|HO(O)C\s]\s]}}. Although phthalic acid is of modest commercial importance, the closely related derivative ] is a commodity chemical produced on a large scale.<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a20_181.pub2|title=Phthalic Acid and Derivatives|year=2007|last1=Lorz|first1=Peter M.|last2=Towae|first2=Friedrich K.|last3=Enke|first3=Walter|last4=Jäckh|first4=Rudolf|last5=Bhargava|first5=Naresh|last6=Hillesheim|first6=Wolfgang|display-authors=3}}</ref> Phthalic acid is one of three ] of ], the others being ] and ]. |
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==Production== |
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==Production== |
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Phthalic acid is produced by the catalytic oxidation of ] directly to ] and a subsequent hydrolysis of the anhydride.<ref name=Ullmann/> |
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Phthalic acid is produced by the catalytic oxidation of ] or ] directly to ] and a subsequent hydrolysis of the anhydride.<ref name=Ullmann/> |
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Phthalic acid was first obtained by ] ] ] in 1836 by ] naphthalene tetrachloride. Believing the resulting substance to be a naphthalene derivative, he named it naphthalenic acid. After the ] chemist ] 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. |
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Phthalic acid was first obtained by ] ] ] in 1836 by ] naphthalene tetrachloride.<ref name=EB1911>{{cite EB1911 |wstitle=Phthalic Acids |volume=21 |pages=545–546}}</ref> Believing the resulting substance to be a naphthalene derivative, he named it "naphthalic acid".<ref name=EB1911/><ref>Auguste Laurent (1836) (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.)</ref><ref>Reprinted in German as: Auguste Laurent (1836) (On naphthalenic acid and its compounds), ''Annalen der Pharmacie'', '''19''' (1) : 38-50; for the preparation of phthalic acid, see page 41.</ref> After the ] chemist ] determined its correct formula,<ref>C. de Marignac (1841) ("On naphthalinic acid and a volatile 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.)</ref> Laurent gave it its present name.<ref name=EB1911/><ref>Auguste Laurent (1841) (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.</ref><ref>Reprinted in German as: Auguste Laurent (1842) (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).</ref> 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.<ref name=EB1911/> |
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==Synthesis== |
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==Reactions and uses== |
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Naphthalene, on oxidation with ] or ], gives Phthalic anhydride,<ref>{{Cite web |title=Oxidation of Naphthalene to Phthalic Anhydride |url=https://public.websites.umich.edu/~elements/08chap/html/runaway/example3.htm |access-date=2024-04-06 |website=public.websites.umich.edu}}</ref> which, through hydrolysis with hot water, gives Phthalic acid.<ref>{{Cite book |last=Noller |first=Carl R. |title=Chemistry of Organic Compounds |date=1965 |publisher=Philadelphia: W. B. Saunders |edition=3rd |pages=602}}</ref> |
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It is a dibasic acid, with p''K''<sub>a</sub>'s of 2.89 and 5.51. The monopotassium salt, ] is a standard acid in ]. Typically phthalate esters are prepared from the widely available ]. Reduction of phthalic acid with ] in the presence of water gives the ] derivative.<ref>{{OrgSynth | author = Richard N. McDonald and Charles E. Reineke | title = trans-1,2-Dihydrophthalic Acid | collvol = 6 | collvolpages = 461 | prep = cv6p0461 | year = 1988}}</ref> |
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==Isomers== |
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==Uses== |
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Phthalic acid in the form of ] is an important industrial chemical, used for making ] (]s of phthalic acid) that are used as ]s. However, phthalic anhydride is usually not made by dehydration of phthalic acid but from ] or ]. |
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Phthalic acid is one of three ] of benzenedicarboxylic acid, the others being ] and ]. 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. |
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==Reactions== |
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{| |
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It is a dibasic acid, with p''K''<sub>a</sub>s of 2.89 and 5.51. The monopotassium salt, ] is a standard acid in ]. Typically phthalate esters are prepared from the widely available ]. Reduction of phthalic acid with ] in the presence of water gives the ] derivative.<ref>{{OrgSynth | author = Richard N. McDonald and Charles E. Reineke | title = trans-1,2-Dihydrophthalic Acid | collvol = 6 | collvolpages = 461 | prep = cv6p0461 | year = 1988}}</ref> |
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|] |
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| phthalic acid |
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| isophthalic acid |
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| terephthalic acid |
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| (''ortho''-phthalic acid) |
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| (''meta''-phthalic acid) |
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| (''para''-phthalic acid) |
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==Safety== |
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==Safety== |
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The toxicity of phthalic acid is low with LD<sub>50</sub> (mouse) of 550 mg/kg. However, many ] have been implicated as ]. |
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The toxicity of phthalic acid is moderate with {{LD50}} (mouse) of 550 mg/kg. |
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==Biodegradation== |
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The bacteria ''Pseudomonas'' sp. P1 degrades phthalic acid.<ref>{{cite thesis|type=Ph.D.|url=http://prr.hec.gov.pk/Thesis/3362H.pdf|first=Muhammad |last=Ishtiaq Ali|title=Microbial degradation of polyvinyl chloride plastics|publisher=Quaid-i-Azam University|year=2011|pages=47}}</ref> |
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==See also== |
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==See also== |
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* ], a ] for ]s |
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* ], a ] for ]s |
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==References== |
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==References== |
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{{reflist|30em}} |
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<references/> |
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* Merck Index, 9th ed, #7178 |
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* Merck Index, 9th ed, #7178 |
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{{DEFAULTSORT:Phthalic Acid}} |
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