| Revision as of 16:10, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 468941548 of page Isophthalic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 23:25, 10 January 2024 edit Brinerustle (talk | contribs)Extended confirmed users1,083 editsNo edit summary |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 446280581 |
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| verifiedrevid = 470454686 |
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| Name = Isophthalic acid |
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| ImageFile = Isophthalic-acid-2D-skeletal.png |
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| Name = Isophthalic acid |
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| ImageFile = Isophthalic-acid-2D-skeletal.png |
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| ImageName = Skeletal formula |
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| ImageName = Skeletal formula |
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| ImageFile1 = Isophthalic-acid-3D-balls.png |
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| ImageFile1 = Isophthalic acid 3D ball.png |
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| ImageName1 = Ball-and-stick model |
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| ImageAlt1 = Ball-and-stick model of the isophthalic acid molecule |
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| OtherNames = Benzene-1,3-dicarboxylic acid<br />''meta''-Phthalic acid |
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| PIN = Benzene-1,3-dicarboxylic acid <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) --> |
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| OtherNames = Isophthalic acid<br />''meta''-Phthalic acid |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 30802 |
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| ChEBI = 30802 |
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| SMILES = O=C(O)c1cccc(C(=O)O)c1 |
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| SMILES = O=C(O)c1cccc(C(=O)O)c1 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8182 |
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| ChemSpiderID = 8182 |
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| PubChem = 8496 |
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| PubChem = 8496 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 121-91-5 |
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| CASNo = 121-91-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = X35216H9FJ |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=8 |
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| Formula = C<sub>6</sub>H<sub>4</sub>(COOH)<sub>2</sub> |
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| H=6 |
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| MolarMass = 166.14 g/mol |
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| O=4 |
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| Appearance = White crystalline solid |
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| Appearance = White crystalline solid |
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| Density = 1.526 g/cm<sup>3</sup>, Solid |
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| Density = 1.526 g/cm<sup>3</sup>, Solid |
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| Solubility = Insoluble in water |
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| Solubility = Insoluble |
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| pKa=3.46, 4.46<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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| pKa=3.46, 4.46<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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| BoilingPt = |
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| BoilingPt = |
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| MagSus = -84.64·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Section3 = {{Chembox Structure |
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|Section3={{Chembox Structure |
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| CrystalStruct = |
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| Dipole = |
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| Dipole = |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| EUClass = not listed |
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| FlashPt = |
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| HPhrases = {{HPhrases|}} |
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| PPhrases = {{PPhrases|}} |
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| GHS_ref = <ref>GHS: </ref> |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| Function = ]s |
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| OtherFunction_label = ]s |
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| OtherFunctn = ]<br />] (''ortho'') <br />] (''para'') <br /> ] (benzene-1,3,5-tricarboxyllic acid) |
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| OtherFunction = ]<br />] (''ortho'') <br />] (''para'') <br /> ] |
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| OtherCompounds = |
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'''Isophthalic acid''' is an ] with the ] C<sub>6</sub>H<sub>4</sub>(CO<sub>2</sub>H)<sub>2</sub>. This colorless solid is an isomer of ] and ]. The main industrial uses of purified isophthalic acid (PIA) are for the production of ] (PET) resin and for the production of ] (UPR) and other types of coating resins. |
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Isophthalic acid is one of three ] of ], the others being ] and ]. |
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Crystalline isophthalic acid is built up from molecules connected by hydrogen bonds, forming infinite chains.<ref>{{cite journal |last1=Derissen |first1=JL |date=1974 |title=The crystal structure of isophthalic acid |journal=Acta Crystallogr. |volume=B30 |issue=6 |pages=764–2765 |doi=10.1107/S0567740872004844 }}</ref> |
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==Preparation== |
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Isophthalic acid is produced on the billion kilogram per year scale by oxidizing ] using oxygen.<ref name=Ullmann/> The process employs a ]-] ]. The world's largest producer of isophthalic acid is ].<ref>{{Cite web|url=http://pulsenews.co.kr/view.php?year=2017&no=315343|title=Lotte Chemical to invest $3.2mn to beef up meta-xylene and polycarbonate production|website=Pulse}}</ref> |
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In the laboratory, ] can be used as the oxidant. It also arises by fusing potassium meta-sulfobenzoate, or meta-bromobenzoate with ] (terephthalic acid is also formed in the last case). |
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The barium ], as its ], is very soluble in water (a distinction between phthalic and terephthalic acids). ], 5-methylisophthalic acid, is obtained by oxidizing ] or by condensing ] with baryta water. |
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==Applications== |
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] ]s are used as precursors (in the form of ]s) to commercially important polymers, e.g. the fire-resistant material ]. Mixed with terephthalic acid, isophthalic acid is used in the production of PET resins for drink ]s and food packaging. The high-performance polymer ] is produced from isophthalic acid.<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}}</ref> Also, the acid is used as an important input to produce insulation materials. |
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==References== |
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<references/> |
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{{Note}}Note: reference 2 refers to the ortho isomer. Accurate cites for the meta isomer not available. |
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==External links== |
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{{Authority control}} |
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