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{{chembox |
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{{chembox |
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|Verifiedfields = changed |
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| verifiedrevid = 401621752 |
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|Watchedfields = changed |
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| Name = Terephthalic acid |
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|verifiedrevid = 444216370 |
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| ImageFile = Terephthalic-acid-2D-skeletal.svg |
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|Name = Terephthalic acid |
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| ImageSize = 220 |
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|ImageFile = Terephthalic-acid-2D-skeletal.svg |
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| ImageName = Skeletal formula |
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|ImageSize = 220 |
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| ImageFile2 = Terephthalic-acid-3D-balls-B.png |
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|ImageName = Skeletal formula |
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| ImageSize2 = 220 |
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|ImageFile2 = Terephthalic acid 3D ball.png |
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| ImageName2 = Ball-and-stick model |
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|ImageSize2 = 220 |
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| OtherNames = Benzene-1,4-dicarboxylic acid<br />''para''-Phthalic acid<br />TPA<br />PTA |
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|ImageName2 = Ball-and-stick model of the terephthalic acid molecule |
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| Section1 = {{Chembox Identifiers |
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|PIN = Benzene-1,4-dicarboxylic acid <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) --> |
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| ChEBI = 15702 |
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|OtherNames = Terephthalic acid<br />''para''-Phthalic acid<br />TPA<br />PTA<br /> BDC |
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| SMILES = c1cc(ccc1C(=O)O)C(=O)O |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChemSpiderID = 7208 |
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|ChEBI = 15702 |
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| InChI = 1/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12) |
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|SMILES = O=C(O)c1ccc(C(O)=O)cc1 |
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| InChIKey = KKEYFWRCBNTPAC-UHFFFAOYAF |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID = 7208 |
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| StdInChI = 1S/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12) |
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|InChI = 1/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = KKEYFWRCBNTPAC-UHFFFAOYSA-N |
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|InChIKey = KKEYFWRCBNTPAC-UHFFFAOYAF |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI = 1S/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12) |
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| CASNo = 100-21-0 |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| RTECS = WZ0875000 |
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|StdInChIKey = KKEYFWRCBNTPAC-UHFFFAOYSA-N |
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}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| Section2 = {{Chembox Properties |
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|CASNo = 100-21-0 |
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| Formula = C<sub>8</sub>H<sub>6</sub>O<sub>4</sub> |
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|UNII_Ref = {{fdacite|changed|FDA}} |
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| MolarMass = 166.13 g/mol |
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|UNII = 6S7NKZ40BQ |
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| Appearance = white crystals or powder |
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|RTECS = WZ0875000 |
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| Density = 1.522 g/cm³ |
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|PubChem = 7489 |
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| Solubility = 0.0017 g/100 mL at 25°C |
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|EC_number = 202-830-0 |
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| SolubleOther =polar organic solvents aqueous base |
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|ChEMBL = 1374420 |
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| MeltingPt = 300°C in a sealed tube |
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|KEGG = C06337 |
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| Melting_notes = sublimes at 402°C (675 K) in air |
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|3DMet = B00943 |
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| BoilingPt = sublimes |
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|Beilstein = 1909333 |
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| TriplePoint = 427° |
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|Gmelin = 50561 |
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| pKa=3.51, 4.82<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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| Section3 = {{Chembox Structure |
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|Section2={{Chembox Properties |
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|C=8|H=6|O=4 |
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| CrystalStruct = |
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|Appearance = White crystals or powder |
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| Dipole = zero |
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|Density = 1.519 g/cm<sup>3</sup><ref name=crc>Haynes, p. 3.492</ref> |
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}} |
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|Solubility = 0.065 g/L at 25 °C<ref>Haynes, p. 5.163</ref> |
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| Section7 = {{Chembox Hazards |
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|SolubleOther =polar organic solvents aqueous base |
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| ExternalMSDS = |
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|MeltingPtC = 300 |
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| EUClass = not listed |
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|MeltingPt_notes = Sublimes<ref name=crc/> |
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| FlashPt = |
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|BoilingPt =Decomposes |
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}} |
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|pKa=3.54, 4.34<ref>Haynes, p. 5.96</ref> |
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| Section8 = {{Chembox Related |
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|MagSus = {{val|-83.5|e=-6|u=cm<sup>3</sup>/mol}}<ref>Haynes, p. 3.579</ref> |
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| Function = ]s |
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}} |
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| OtherFunctn = ]<br /> ]<br /> ]<br /> ] |
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|Section3={{Chembox Structure |
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| OtherCpds = ]<br /> ]<br /> ] |
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|Dipole = 2.6D <ref>{{cite journal | title = Electronic and vibrational investigation and NMR–mass spectroscopic analysis of terephthalic acid using quantum Gaussian calculations | journal = ] | volume = 139 | pages = 229–242 | year = 2015 | doi = 10.1016/j.saa.2014.11.112|pmid= 25561302|bibcode= 2015AcSpA.139..229K| last1 = Karthikeyan | first1 = N. | last2 = Joseph Prince | first2 = J. | last3 = Ramalingam | first3 = S. | last4 = Periandy | first4 = S. }}</ref> |
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}} |
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|Section4={{Chembox Thermochemistry |
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|Thermochemistry_ref=<ref>Haynes, p. 5.37</ref> |
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|DeltaHf= −816.1 kJ/mol |
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}} |
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|Section5={{Chembox Hazards |
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|ExternalSDS = |
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|GHSPictograms = {{GHS07}} |
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|GHSSignalWord = Warning |
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|HPhrases = {{H-phrases|315|319|335}} |
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|PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}} |
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| FlashPtC =260 |
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| FlashPt_ref =<ref name=crc2>Haynes, p. 16.29</ref> |
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| AutoignitionPtC =496 |
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| AutoignitionPt_ref=<ref name=crc2/> |
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| TLV-STEL = 10 mg/m<sup>3</sup><ref>Haynes, p. 16.42</ref> |
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| LD50 = >1 g/kg (oral, mouse)<ref name=Ullmann/> |
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}} |
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|Section6={{Chembox Related |
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|OtherFunction_label = ]s |
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|OtherFunction = ]<br /> ]<br /> ]<br /> ] |
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|OtherCompounds = ]<br /> ]<br /> ] |
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'''Terephthalic acid''' is the ] with ] C<sub>6</sub>H<sub>4</sub>(COOH)<sub>2</sub>. This colourless solid is a ] ], used principally as a precursor to the ] ], used to make clothing and plastic bottles. Several billion kilograms are produced annually. It is one of three ]ic ]s. |
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'''Terephthalic acid''' is an ] with ] C<sub>6</sub>H<sub>4</sub>(CO<sub>2</sub>H)<sub>2</sub>. This white solid is a ] ], used principally as a precursor to the ] ], used to make clothing and ]s. Several million tons are produced annually.<ref name=Ullmann/> The common name is derived from the ]-producing tree '']'' and ]. |
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Terephthalic acid is also used in the production of ].<ref>{{Cite web |title=Polybutylene Terephthalate (PBT) Material Guide & Properties Info |url=https://omnexus.specialchem.com/selection-guide/polybutylene-terephthalate-pbt-plastic |access-date=2023-11-24 |website=omnexus.specialchem.com |language=en|archive-url=https://web.archive.org/web/20231124155646/https://omnexus.specialchem.com/selection-guide/polybutylene-terephthalate-pbt-plastic|archive-date=2023-11-24}}</ref> |
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==Properties== |
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Terephthalic acid is poorly soluble in water and alcohols, consequently up until around 1970 most crude terephthalic acid was converted to the dimethyl ] for purification. It sublimes when heated. |
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==Production== |
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==History== |
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Terephthalic acid was first isolated (from turpentine) by the French chemist Amédée Cailliot (1805–1884) in 1846.<ref>{{cite journal|first=Amédée|last=Cailliot|date=1847|url=https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dxz;view=1up;seq=31|title=Études sur l'essence de térébenthine|trans-title=Studies of the essence of turpentine|journal=Annales de Chimie et de Physique |series=Série 3|volume=21|pages=27–40}} Terephthalic acid is named on p. 29: "Je désignerai le premier de ces acides, celui qui est insoluble, sous le nom d<nowiki>'</nowiki>''acide téréphtalique''." (I will designate the first of these acids, which is insoluble, by the name of ''terephthalic acid''.)</ref> Terephthalic acid became industrially important after ]. Terephthalic acid was produced by oxidation of ] with 30-40% ]. Air oxidation of ''p''-xylene gives ], which resists further air-oxidation. Esterification of ''p''-toluic acid to ] (CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>CO<sub>2</sub>CH<sub>3</sub>) opens the way for further oxidation to monomethyl terephthalate. In the Dynamit−Nobel process these two oxidations and the esterification were performed in a single reactor. The reaction conditions also lead to a second esterification, producing ], which could be hydrolysed to terepthalic acid. In 1955, Mid-Century Corporation and ICI announced the bromide-] oxidation of ''p''-toluic acid directly to terephthalic acid, without the need to isolate intermediates and still using air as the oxidant. Amoco (as Standard Oil of Indiana) purchased the Mid-Century/ICI technology, and the process is now known by their name.<ref name=CR/> |
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Terephthalic acid is produced by ] of ] by ] in ]: |
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The oxidation is conducted using ] as ] and a ] composed of ] and ] salts, using a ] promoter. The yield is nearly quantitative. The most problematic impurity is 4-formylbenzoic acid, which is removed by ] of a hot aqueous solution. The solution is then cooled in a stepwise manner to ] highly pure terephthalic acid. |
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==Synthesis== |
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Alternatively, but not commercially significant, is the so-called "] process" or "Raecke process," named after the company and patent holder, respectively. This process involves the rearrangement of ] to terephthalic acid via the corresponding potassium ]s.<ref>{{cite journal |
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===Amoco Process=== |
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| title = The Preparation of Terephthalic Acid from Phthalic or Benzoic Acid |
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In the Amoco process, which is widely adopted worldwide, terephthalic acid is produced by catalytic ] of ]:<ref name=CR>{{cite journal|title=p-Xylene Oxidation to Terephthalic Acid: A Literature Review Oriented toward Process Optimization and Development|journal=Chemical Reviews|year=2013|volume=113|issue=10|pages=7421–69|doi=10.1021/cr300298j|pmid=23767849|last1=Tomás |first1=Rogério A. F. |last2=Bordado |first2=João C. M. |last3=Gomes |first3=João F. P. }}</ref> |
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| author = Yoshiro Ogata, Masaru Tsuchida, Akihiko Muramoto |
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:] |
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| journal = ] |
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The process uses a ]–]–] ]. The bromide source can be ], ] or ]. Bromine functions as a regenerative source of ]s. ] is the solvent and ] serves as the oxidant. The combination of bromine and acetic acid is highly ], requiring specialized reactors, such as those lined with ]. A mixture of ], ], the ] system, and compressed air is fed to a reactor. |
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| volume = 79 |
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| issue = 22 |
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====Mechanism==== |
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| pages = 6005–6008 |
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The oxidation of ''p''-xylene proceeds by a free radical process. Bromine radicals decompose cobalt and manganese hydroperoxides. The resulting oxygen-based radicals abstract hydrogen from a methyl group, which have weaker C–H bonds than does the aromatic ring. Many intermediates have been isolated. ''p''-xylene is converted to ], which is less reactive than the p-xylene owing to the influence of the ] ] group. Incomplete oxidation produces ] (4-CBA), which is often a problematic impurity.<ref name=CR/><ref>{{cite journal | title = Semicontinuous Studies on the Reaction Mechanism and Kinetics for the Liquid-Phase Oxidation of ''p''-Xylene to Terephthalic Acid | last1= Wang|first1=Qinbo|first2= Youwei |last2=Cheng |first3=Lijun |last3=Wang|first4= Xi |last4=Li | journal = ] | volume = 46 | issue = 26 | pages = 8980–8992 | year = 2007 | doi = 10.1021/ie0615584}}</ref> |
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| year = 1957 |
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<ref name="Xiao2010">{{cite journal | title = Aerobic Oxidation of ''p''-Toluic Acid to Terephthalic Acid over T(''p''-Cl)PPMnCl/Co(OAc)<sub>2</sub> Under Moderate Conditions | first1 = Y. | last1= Xiao |first2= W.-P.|last2= Luo|first3= X.-Y.|last3= Zhang |first4=C.-C.|last4= Guo|first5= Q.|last5= Liu|first6= G.-F.|last6= Jiang |first7=Q.-H.|last7= Li|display-authors=3 | journal = ] | volume = 134 | issue = 1–2 | pages = 155–161 | year = 2010 | doi = 10.1007/s10562-009-0227-1| s2cid = 95855968 }}</ref> |
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| url = |
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| doi = 10.1021/ja01579a043}} |
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</ref><ref>{{cite journal |
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| title = Further Studies on the Preparation of Terephthalic Acid from Phthalic or Benzoic Acid |
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====Challenges==== |
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| author = Yoshiro Ogata, Masaru Hojo, Masanobu Morikawa |
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Approximately 5% of the acetic acid solvent is lost by decomposition or "burning". Product loss by ] to ] is common. The high temperature diminishes oxygen solubility in an already oxygen-starved system. Pure oxygen cannot be used in the traditional system due to hazards of flammable organic–O<sub>2</sub> mixtures. Atmospheric air can be used in its place, but once reacted needs to be purified of ]s and ]s such as ] before being released. Additionally, the corrosive nature of bromides at high temperatures requires the reaction be run in expensive titanium reactors.<ref name="Zuo2008">{{cite journal | title = Liquid-Phase Oxidation of Toluene and ''p''-Toluic Acid under Mild Conditions: Synergistic Effects of Cobalt, Zirconium, Ketones, and Carbon Dioxide | last1= Zuo|first1= Xiaobin|first2= Bala |last2=Subramaniam |first3= Daryle H. |last3=Busch | journal = ] | volume = 47 | issue = 3 | pages = 546–552 | year = 2008 | doi = 10.1021/ie070896h}}</ref><ref name="Zuo2010">{{cite journal | title = Liquid Phase Oxidation of ''p''-Xylene to Terephthalic Acid at Medium-high Temperatures: Multiple Benefits of CO<sub>2</sub>-expanded Liquids | last1= Zuo|first1= Xiaobin|first2= Fenghui|last2= Niu|first3= Kirk|last3= Snavely|first4= Bala |last4=Subramaniam |first5=Daryle H.|last5= Busch|display-authors=3 | journal = ] | volume = 12 | issue = 2 | pages = 260–267 | year = 2010 | doi = 10.1039/B920262E| hdl= 1808/18532|hdl-access= free}}</ref> |
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| journal = ] |
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| volume = 25 |
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====Alternative reaction media==== |
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| issue = 12 |
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The use of ] overcomes many of the problems with the original industrial process. Because CO<sub>2</sub> is a better flame inhibitor than ], a CO<sub>2</sub> environment allows for the use of pure oxygen directly, instead of air, with reduced flammability hazards. The solubility of molecular oxygen in solution is also enhanced in the CO<sub>2</sub> environment. Because more oxygen is available to the system, ] (''T''<sub>c</sub> = 31 °C) has more complete oxidation with fewer byproducts, lower ] production, less decarboxylation and higher purity than the commercial process.<ref name="Zuo2008"/><ref name="Zuo2010"/> |
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| pages = 2082–2087 |
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| year = 1960 |
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In ] medium, the oxidation can be effectively catalyzed by MnBr<sub>2</sub> with pure O<sub>2</sub> in a medium-high temperature. Use of supercritical water instead of acetic acid as a solvent diminishes environmental impact and offers a cost advantage. However, the scope of such reaction systems is limited by the even more demanding conditions than the industrial process (300–400 °C, >200 bar).<ref>{{cite journal | title = Selective Aerobic Oxidation of ''para''-Xylene in Sub- and Supercritical Water. Part 1. Comparison with Ortho-xylene and the Role of the Catalyst | last1= Pérez|first1= Eduardo|first2= Joan |last2=Fraga Dubreuil |first3=Eduardo |last3=García Verdugo |first4=Paul A.|last4= Hamley |first5=W. Barry |last5=Thomas|first6= Duncan |last6=Housley|first7= Wait |last7=Partenheimer|first8=Martyn|last8= Poliakoff|display-authors=3 |journal = ] | volume = 13 | issue = 12 | pages = 2389–2396 | year = 2011 | doi = 10.1039/C1GC15137A}}</ref> |
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| url = |
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| doi = 10.1021/jo01082a003}} |
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===Promotors and additives=== |
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</ref> Terephthalic acid can be prepared in the laboratory by oxidizing various para-disubstituted derivatives of ] including ] or a mixture of ] and ] with ]. |
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As with any large-scale process, many additives have been investigated for potential beneficial effects. Promising results have been reported with the following.<ref name=CR/> |
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*Ketones act as promoters for formation of the active cobalt(III) catalyst. In particular, ketones with α-methylene groups oxidize to hydroperoxides that are known to oxidize cobalt(II). 2-] is often used. |
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*] salts enhance the activity of Co-Mn-Br catalysts. Selectivity is also improved.<ref name=CR/> |
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*] is a potential replacement for bromide, which is highly corrosive. The phthalimide functions by formation of the oxyl radical. |
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*Guanidine inhibits the oxidation of the first methyl but enhances the usually slow oxidation of the toluic acid. |
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===Alternative routes=== |
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Terephthalic acid can also be made from ] by the ], which gives ]. Oxidation of the latter gives terephthalic acid.<ref>{{cite book |doi=10.1002/14356007.a03_463.pub2 |chapter=Benzaldehyde |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2011 |last1=Brühne |first1=Friedrich |last2=Wright |first2=Elaine |isbn=978-3-527-30385-4 }}</ref> |
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Terephthalic acid can be prepared in the laboratory by oxidizing many ''para''-disubstituted derivatives of ], including ] or a mixture of ] and ] with ]. |
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Although not commercially significant, there is also the so-called "] process" or "Raecke process", named after the company and patent holder, respectively. This route involves the transfer of carboxylate groups. Either ] disproportionates to potassium terephthalate and ] or ] rearranges to the terephthalate.<ref>{{cite journal | title = The Preparation of Terephthalic Acid from Phthalic or Benzoic Acid |first1=Yoshiro|last1= Ogata |first2=Masaru |last2=Tsuchida |first3=Akihiko|last3= Muramoto | journal = ] | volume = 79 | issue = 22 | pages = 6005–6008 | year = 1957 | doi = 10.1021/ja01579a043}}</ref><ref>{{cite journal | title = Further Studies on the Preparation of Terephthalic Acid from Phthalic or Benzoic Acid |first1=Yoshiro|last1= Ogata |first2=Masaru |last2=Hojo |first3=Masanobu |last3=Morikawa | journal = ] | volume = 25 | issue = 12 | pages = 2082–2087 | year = 1960 | doi = 10.1021/jo01082a003}}</ref> ] can be used as a raw material and then potassium can be recycled.<ref>{{Cite journal |last=Terashi |first=Michio |last2=Hasegawa |first2=Toshio |last3=Kikuchi |first3=Shoji |last4=Kasahara |first4=Toshiji |date=1962 |title=The Synthesis of Terephthalic Acid from Phthalic Anhydride |url=https://www.jstage.jst.go.jp/article/yukigoseikyokaishi1943/20/1/20_1_40/_article |journal=Journal of Synthetic Organic Chemistry, Japan |volume=20 |issue=1 |pages=40–55 |doi=10.5059/yukigoseikyokaishi.20.40}}</ref> |
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Lummus (now a subsidiary of ]) has reported a route from the dinitrile, which can be obtained by ] of ''p''-xylene. |
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==Applications== |
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==Applications== |
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Virtually the entire world's supply of terephthalic acid and ] are consumed as precursors to ] (PET). World production in 1970 was around 1.75 million tonnes.<ref>Richard J. Sheehan, "Terephthalic Acid, Dimethyl Terephthalate, and Isophthalic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. {{DOI|10.1002/14356007.a26_193}} Article Online Posting Date: June 15, 2000.</ref> By 2006, global purified terephthalic acid (TPA) demand had exceeded 30 million tonnes. |
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Virtually the entire world's supply of terephthalic acid and ] are consumed as precursors to ] (PET). World production in 1970 was around 1.75 million tonnes.<ref name=Ullmann>{{Ullmann|first1=Richard J.|last1=Sheehan|title=Terephthalic Acid, Dimethyl Terephthalate, and Isophthalic Acid|doi=10.1002/14356007.a26_193|date=June 15, 2000}}</ref> By 2006, global purified terephthalic acid (PTA) demand had exceeded 30 million tonnes. A smaller, but nevertheless significant, demand for terephthalic acid exists in the production of ] and several other engineering ].<ref>{{cite book|title=Ashford's Dictionary of Industrial Chemicals|edition=3rd|date=2011|page=8805|isbn=978-0952267430|publisher=Wavelength|place=Saltash, UK}}</ref> |
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===Other uses=== |
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There is a smaller, but nevertheless significant, demand for terephthalic acid in the production of ] and several other engineering ].<ref> Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 8805</ref> |
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*Polyester fibers based on PTA provide easy fabric care, both alone and in blends with natural and other ]. Polyester films are used widely in audio and video recording tapes, data storage tapes, photographic films, labels and other sheet material requiring both dimensional stability and toughness. |
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*Terephthalic acid is used in paint as a carrier. |
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*Terephthalic acid is used as a raw material to make terephthalate plasticizers such as ] and dibutyl terephthalate. |
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*It is used in the pharmaceutical industry as a raw material for certain drugs. |
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*In addition to these end uses, Terephthalic acid based ] and ] are also used in hot melt adhesives. |
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*PTA is an important raw material for lower ] saturated polyesters for powder and water-soluble ]. |
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*In the research laboratory, terephthalic acid has been popularized as a component for the synthesis of ]s. |
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*The ] drug ] occasionally comes as a terephthalate salt; however, the more usual salt of oxycodone is the ]. Pharmacologically, one milligram of ''hydrochloridum oxycodonae'' is equivalent to 1.13 mg of ''terephthalas oxycodonae''. |
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*Terephthalic acid is used as a filler in some military ]s, most notably the American M83 smoke grenade and M90 vehicle-employed smoke grenade, producing a thick white smoke that acts as an obscurant in the visual and ] spectrum when burned. |
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==Solubility== |
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In the research laboratory, terephthalic acid has been popularized as a component for the synthesis of ]s. |
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Terephthalic acid is poorly soluble in water and alcohols; consequently, until about 1970 terephthalic acid was purified as its dimethyl ]. It sublimes when heated. |
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{| |
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{| class="wikitable" |
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|+Solubility (g/100 g solvent) |
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|- |
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! Solvent !! 25 °C !! 120 °C !! 160 °C !! 200 °C !! 240 °C |
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|- |
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| ] || 0.1 || — || 2.9 || 15 || — |
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|- |
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| ] || 0.0019 || 0.08 || 0.38 || 1.7 || 9.0 |
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|- |
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| ] || 0.035 || 0.3 || 0.75 ||1.8 || 4.5 |
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|- |
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| ] || 0.5 || — || — || — || — |
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|- |
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| ] || 2 || — || — || — || — |
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|- |
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| ] || 6.7 || — || — || — || — |
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| ] || 20 || — || — || — || — |
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:{| class="wikitable" |
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|+Vapor pressure |
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! Temperature<br>(°C) !! Pressure<br>(kPa) |
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| 303 || 1.3 |
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| 353 || 13.3 |
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| 370 || 26.7 |
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| 387 || 53.3 |
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| 404 || 101.3 |
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|} |
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==Toxicity== |
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The ], ], and ] ] occasionally comes as a terephthalate salt; however, the more usual salt of oxycodone is the ]. Pharmacologically, one milligramme of ''terephthalas oxycodonae'' is equivalent to 1.13 mgm of ''hydrochloridum oxycodonae''. |
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Terephthalic acid and its dimethyl ester have very low ], with {{LD50}} >1 g/kg (oral, mouse).<ref name=Ullmann/> |
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==Biodegradation== |
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In '']'' strain E6,<ref>{{cite web |title=GTDB – Genome GCF_001010305.1 |url=https://gtdb.ecogenomic.org/genome?gid=GCF_001010305.1 |website=gtdb.ecogenomic.org}}</ref> terephthalic acid is biodegraded to ], a common natural product, via a reaction pathway initiated by ]. Combined with the previously known ] and ], a full pathway for ] degradation can be engineered.<ref>{{cite journal |last1=Kincannon |first1=William M. |last2=Zahn |first2=Michael |last3=Clare |first3=Rita |last4=Lusty Beech |first4=Jessica |last5=Romberg |first5=Ari |last6=Larson |first6=James |last7=Bothner |first7=Brian |last8=Beckham |first8=Gregg T. |last9=McGeehan |first9=John E. |last10=DuBois |first10=Jennifer L.|display-authors=3 |title=Biochemical and structural characterization of an aromatic ring–hydroxylating dioxygenase for terephthalic acid catabolism |journal=Proceedings of the National Academy of Sciences |date=29 March 2022 |volume=119 |issue=13 |pages=e2121426119 |doi=10.1073/pnas.2121426119|doi-access=free |pmid=35312352|pmc=9060491 |bibcode=2022PNAS..11921426K}}</ref> |
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==See also== |
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*] a thermoplastic polyester formed from terephthalic acid |
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==References== |
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==References== |
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{{reflist|}} |
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<references/> |
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* ] |
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==Cited sources== |
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*{{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = ] | edition = 97th | publisher = ] | isbn = 9781498754293}} |
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==External links and further reading== |
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==External links and further reading== |
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*''Basic Organic Chemistry: Part 5, Industrial Products'', J.M. Tedder, A. Nechvatal, A.H. Tubb (editors), John Wiley & Sons, Chichester, UK (1975). |
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*{{cite book|title=Basic Organic Chemistry: Part 5, Industrial Products|url=https://archive.org/details/trent_0116401244110|url-access=registration|editor1-first=J. M.|editor1-last=Tedder|editor2-first=A.|editor2-last=Nechvatal|editor3-first=A. H.|editor3-last=Tubb|publisher=John Wiley & Sons|location=Chichester, UK|date=1975|isbn=9780471850144}} |
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{{Authority control}} |
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==See Also== |
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*] a thermoplastic polyester formed from terephthalic acid |
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