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Revision as of 06:39, 11 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').		Latest revision as of 13:48, 19 July 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits added Category:Acetyl compounds using HotCat
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	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 401621752
			| verifiedrevid = 444216370
	| Name = Terephthalic acid
			| Name = 2,6-Diacetylpyridine
	| ImageFile = Terephthalic-acid-2D-skeletal.svg
			| ImageFile1 = 2,6-Diacetylpyridine.svg
	| ImageSize = 220
			| ImageSize1 = 180
	| ImageName = Skeletal formula
			| ImageName1 = Skeletal formula
	| ImageFile2 = Terephthalic-acid-3D-balls-B.png
			| ImageFile2 = 2,6-Ac2py.jpg
	| ImageSize2 = 220
			| ImageSize2 = 230
	| ImageName2 = Ball-and-stick model
			| ImageName2 =
	| OtherNames = Benzene-1,4-dicarboxylic acid<br />''para''-Phthalic acid<br />TPA<br />PTA
			| PIN = 1,1′-(Pyridine-2,6-diyl)di(ethan-1-one)
	| Section1 = {{Chembox Identifiers
			| OtherNames = 1,1′-(Pyridine-2,6-diyl)diethanone<br />1-(6-Acetylpyridin-2-yl)ethanone<br />DAP <br />2,6-Bisacetylpyridine
	| ChEBI = 15702
			|Section1={{Chembox Identifiers
	| SMILES = c1cc(ccc1C(=O)O)C(=O)O
			| SMILES = CC(=O)c1cccc(n1)C(=O)C
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 7208
			| ChemSpiderID = 63955
	| InChI = 1/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12)
			| StdInChI = InChI=1S/C9H9NO2/c1-6(11)8-4-3-5-9(10-8)7(2)12/h3-5H,1-2H3
	| InChIKey = KKEYFWRCBNTPAC-UHFFFAOYAF
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12)
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = KKEYFWRCBNTPAC-UHFFFAOYSA-N		| StdInChIKey = BEZVGIHGZPLGBL-UHFFFAOYSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 100-21-0		| CASNo = 1129-30-2
			| UNII_Ref = {{fdacite|correct|FDA}}
	| RTECS = WZ0875000
			| UNII = P34UXL3MYV
			| PubChem = 70790
			| EC_number = 214-442-9
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=9 | H=9 | N=1 | O=2
	| Formula = C<sub>8</sub>H<sub>6</sub>O<sub>4</sub>
			| Appearance = White crystals
	| MolarMass = 166.13 g/mol
			| Density = 1.119 g/cm<sup>3</sup>
	| Appearance = white crystals or powder
			| MeltingPtC = 81
	| Density = 1.522 g/cm³
			| MeltingPt_notes = Sublimes at {{convert|110|to|130|C|F K}}
	| Solubility = 0.0017 g/100 mL at 25°C
			| BoilingPtC = 126
	| SolubleOther =polar organic solvents aqueous base
	| MeltingPt = 300°C in a sealed tube
	| Melting_notes = sublimes at 402°C (675 K) in air
	| BoilingPt = sublimes
	| TriplePoint = 427°
	| 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>
	}}		}}
	| Section3 = {{Chembox Structure		|Section3={{Chembox Structure
	| CrystalStruct =		| CrystalStruct =
	| Dipole = zero		| Dipole =
	}}		}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
			| GHSPictograms = {{GHS07}}
	| EUClass = not listed
			| GHSSignalWord = Warning
	| FlashPt =
			| HPhrases = {{H-phrases|315|319|335}}
	}}
			| 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}}
	| Section8 = {{Chembox Related
			| FlashPt =
	| Function = ]s
	| OtherFunctn = ]<br /> ]<br /> ]<br /> ]
	| OtherCpds = ]<br /> ]<br /> ]
	}}		}}
			|Section8={{Chembox Related
			| OtherFunction_label = ]s
			| OtherFunction = ]
			}}
	}}		}}
	'''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.		'''2,6-Diacetylpyridine''' is an ] with the ] C<sub>5</sub>H<sub>3</sub>N(C(O)CH<sub>3</sub>)<sub>2</sub>. It is a white solid that is soluble in organic solvents. It is a disubstituted ]. It is a precursor to ]s in ].<ref name="azamacrocycle">{{cite journal
			| title = The Advent of Macrocyclic Chemistry
			| author = Curtis, N. F.
			| journal = Supramolecular Chemistry
			| volume = 24
			| issue = 7
			| pages = 439–447
			| year = 2012
			| url =
			| doi = 10.1080/10610278.2012.688123 | s2cid = 96660708
			}}
			</ref><ref name = "DIP"/>
	==Properties==		==Synthesis==
			The synthesis of 2,6-diacetylpyridine begins with oxidation of the methyl groups in ] to form ]. This process has been well established with ] and ].<ref>
	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.
			{{ cite patent
			| country = CA
			| number = 1108617
			| status = patent
			| title = Two Stage Process for Preparing 2,6-pyridinedicarboxylic acid
			| pubdate =
			| gdate =
			| fdate =
			| pridate =
			| inventor = Agnese, G.
			| invent1 = Ghelli, G.
			| invent2 = Burshchi, E.
			| assign1 =
			| assign2 =
			| class =
			}}
			</ref> The diketone can be formed from the diester of picolinic acid groups through a ].<ref>{{cite journal | doi = 10.1021/om201212m| pmid = 22675236| pmc = 3366276| title = Electronic Effects in 4-Substituted Bis(imino)pyridines and the Corresponding Reduced Iron Compounds| journal = Organometallics| volume = 31| issue = 6| pages = 2275–2285| year = 2012| last1 = Darmon| first1 = Jonathan M.| last2 = Turner| first2 = Zoë R.| last3 = Lobkovsky| first3 = Emil| last4 = Chirik| first4 = Paul J.| last5 = Finkelstein| first5 = K. D.| last6 = Wieghardt| first6 = K.| last7 = Debeer| first7 = S.| last8 = Chirik| first8 = P. J.}}</ref> The resulting adduct can be decarboxylated to give diacetylpyridine.<ref>{{cite journal
			| title = Controlled Synthesis of 2-Acetyl-6-carbethioxypyridine and 2-6-Diacetylpyridine from 2,6-Dimethylpyridine
			|author1=Yoshiro Ogata |author2=Masaru Tsuchida |author3=Akihiko Muramoto | journal = ]
			| volume = 35
			| issue = 17
			| pages = 2317–2324
			| year = 2006
			| url =
			| doi = 10.1080/00397910500186995|s2cid=93168188 }}
			</ref>
			:]
	==Production==
	Terephthalic acid is produced by ] of ] by ] in ]:
	:]
	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.
			Treating 2,6-pyridinedicarbonitrile with ] provides an alternative synthesis for the diketone.<ref name = "DIP">{{cite journal
	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
			| title = Hydrogenized iron(II) complexes as highly active ethene polymerization catalysts
	| title = The Preparation of Terephthalic Acid from Phthalic or Benzoic Acid
			|author1=Schmidt, R. |author2=Welch, M.B. |author3=Palackal, S.J. |author4=Alt, H.G. | journal = Journal of Molecular Catalysis A: Chemical
	| author = Yoshiro Ogata, Masaru Tsuchida, Akihiko Muramoto
			| volume = 179
	| journal = ]
	| volume = 79		| issue = 1–2
	| issue = 22		| pages = 155–173
	| pages = 6005–6008		| year = 2001
	| year = 1957
	| url =		| url =
	| doi = 10.1021/ja01579a043}}		| doi = 10.1016/S1381-1169(01)00333-8}}
	</ref><ref>{{cite journal		</ref>
	| title = Further Studies on the Preparation of Terephthalic Acid from Phthalic or Benzoic Acid
	| author = Yoshiro Ogata, Masaru Hojo, Masanobu Morikawa
	| journal = ]
	| volume = 25
	| issue = 12
	| pages = 2082–2087
	| year = 1960
	| url =
	| doi = 10.1021/jo01082a003}}
	</ref> Terephthalic acid can be prepared in the laboratory by oxidizing various para-disubstituted derivatives of ] including ] or a mixture of ] and ] with ].
			:]
	==Applications==
	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.
			==Precursor to Schiff base ligands==
	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>
			Diacetylpyridine is a popular starting material for ligands in coordination chemistry, often via ]s. The ] (DIP) class of ligands can be formed from diacetylpyridine through ] condensation with substituted ]s. Diiminopyridine ligands have been the focus of much interest due to their ability to traverse a wide range of ].<ref name = "DIP"/>
			:]
	In the research laboratory, terephthalic acid has been popularized as a component for the synthesis of ]s.
			In azamacrocycle chemistry, diacetylpyridines can undergo the same Schiff base condensation with N1-(3-aminopropyl)propane-1,3-diamines. The product of the condensation can be hydrogenated to yield macrocyclic ]s. Similar penta- and ]s have been synthesized by varying the polyamine chain.<ref name = "azamacrocycle" />
	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''.
			==See also==
			*]
	==References==		==References==
	<references/>		<references/>
	* ]
	==External links and further reading==
	*''Basic Organic Chemistry: Part 5, Industrial Products'', J.M. Tedder, A. Nechvatal, A.H. Tubb (editors), John Wiley & Sons, Chichester, UK (1975).
	*
	==See Also==
	*] a thermoplastic polyester formed from terephthalic acid
	]
	]
	]
			{{DEFAULTSORT:Diacetylpyridine, 2,6-}}
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