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Revision as of 10:41, 10 April 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,044 edits Saving copy of the {{chembox}} taken from revid 485907856 of page Phthalic_anhydride for the Chem/Drugbox validation project (updated: 'ChemSpiderID', 'ChEBI', 'StdInChI', 'StdInChIKey').  Latest revision as of 00:00, 17 December 2024 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,520 edits Fixes images on dark mode 
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{{use dmy dates |date=December 2021}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 447872519
| Watchedfields = changed
| Name = Phthalic anhydride
| verifiedrevid = 486601904
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| Name = Phthalic anhydride
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1 = Phthalic anhydride-2D-Skeletal.png | ImageFileL1 = Phthalic anhydride-2D-Skeletal.png
| ImageNameL1 = Skeletal formula of phthalic anhydride
| ImageSizeL1 = 110px
| ImageClassL1 = skin-invert
| ImageNameL1 = Skeletal formula of phthalic anhydride
| ImageFileR1 = Phthalic-anhydride-3D-spacefill.png | ImageFileR1 = Phthalic-anhydride-3D-spacefill.png
| ImageNameR1 = Space-filing model
| ImageSizeR1 = 130px
| ImageFile2 = Sample of phthalic anhydride.jpg
| ImageNameR1 = Space-filing model
| PIN = 2-Benzofuran-1,3-dione<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 835 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref>
| IUPACName = 2-benzofuran-1,3-dione
| OtherNames = Isobenzofuran-1,3-dione | OtherNames = Isobenzofuran-1,3-dione<ref name=iupac2013 /><br />Phthalic anhydride<ref name=iupac2013 />
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| ChEBI = 36605
| CASNo = 85-44-9
| Beilstein = 118515
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 36605
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6552
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1371297
| EC_number = 201-607-5
| Gmelin = 27200
| PubChem = 6811
| RTECS = TI3150000
| UNNumber = 2214
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = UVL263I5BJ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H4O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4H | StdInChI = 1S/C8H4O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LGRFSURHDFAFJT-UHFFFAOYSA-N | StdInChIKey = LGRFSURHDFAFJT-UHFFFAOYSA-N
| SMILES = O=C1OC(=O)c2ccccc12
| ChemSpiderID = 6552
| SMILES = O=c1oc(=O)c2ccccc12
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 85-44-9
| RTECS = TI3150000
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>8</sub>H<sub>4</sub>O<sub>3</sub> | Formula = C<sub>8</sub>H<sub>4</sub>O<sub>3</sub>
| MolarMass = 148.1 g/mol | MolarMass = 148.1 g/mol
| Appearance = white Flakes | Appearance = white flakes
| Odor = characteristic, acrid<ref name=PGCH/>
| Density = 1.53 g/cm<sup>3</sup>, solid
| Density = 1.53 g/cm<sup>3</sup>, solid; 1.20 g/mL, molten<ref name=PGCH/>
| Solubility = 0.62 g/100g (20—25 °C); <br /> 19.0 g/100g (100 °C); <br /> reacts slowly
| Solubility = 0.62 g/100g (20—25&nbsp;°C); <br /> 19.0 g/100g (100&nbsp;°C); <br /> reacts slowly
| MeltingPt = 131 °C
| MeltingPtC = 131.6
| BoilingPt = 295 °C ''subl.''
| BoilingPtC = 295
| BoilingPt_notes = sublimates
| VaporPressure = 0.0015 mmHg (20&nbsp;°C)<ref name=PGCH/>
| MagSus = {{val|-67.31e-6|u=cm<sup>3</sup>/mol}}
}} }}
| Section3 = {{Chembox Structure |Section3={{Chembox Structure
| CrystalStruct = | CrystalStruct =
| Dipole = | Dipole =
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| EUClass =
| NFPA-H = 3 | NFPA-H = 3
| NFPA-F = 1 | NFPA-F = 1
| NFPA-R = 0 | NFPA-R = 0
| NFPA-O = | NFPA-S =
| RPhrases = {{R22}}, {{R37/38}}, {{R41}}, {{R42/43}} | GHSPictograms = {{GHS05}}{{GHS07}}{{GHS08}}
| GHSSignalWord = Danger
| SPhrases = {{S2}}, {{S23}}, {{S24/25}}, {{S26}}, {{S37/39}}, {{S46}}
| HPhrases = {{H-phrases|302|315|317|318|334|335}}
| FlashPt = 152 °C
| PPhrases = {{P-phrases|261|264|270|271|272|280|285|301+312|302+352|304+340|304+341|305+351+338|310|312|321|330|332+313|333+313|342+311|362|363|403+233|405|501}}
| FlashPtC = 152
| PEL = TWA 12 mg/m<sup>3</sup> (2 ppm)<ref name=PGCH>{{PGCH|0512}}</ref>
| ExploLimits = 1.7%–10.5%
| IDLH = 60 mg/m<sup>3</sup><ref name=PGCH/>
| LD50 = 4020 mg/kg (oral, rat)<br/>1520 mg/kg (oral, mouse)<br/>800 mg/kg (oral, cat)<br/>800–1600 mg/kg (oral, rat)<br/>2210 mg/kg (oral, mouse)<ref>{{IDLH|85449|Phthalic anhydride}}</ref>
| REL = TWA 6 mg/m<sup>3</sup> (1 ppm)<ref name=PGCH/>
}} }}
| Section8 = {{Chembox Related |Section8={{Chembox Related
| OtherCpds = ]<br />]<br>] | OtherCompounds = ]<br />]<br>]
}} }}
}} }}

'''Phthalic anhydride''' is the ] with the ] C<sub>6</sub>H<sub>4</sub>(CO)<sub>2</sub>O. It is the ] of ]. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commercially. This white solid is an important industrial chemical, especially for the large-scale production of ]s for plastics. In 2000, the worldwide production volume was estimated to be about 3&nbsp;million tonnes per year.<ref name=Ullmann/>

==Synthesis and production==
Phthalic anhydride was first reported in 1836 by ]. Early procedures involved liquid-phase ]-catalyzed ] of ].<ref>{{cite journal |last1=Laurent |first1=Aug. |title=Sur l'acide naphtalique et ses combinaisons |journal=Annales de Chimie et de Physique |date=1836 |volume=61 |pages=113–125 |url=https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dwy&view=1up&seq=119 |series=2nd series |trans-title=On naphthalic acid and its compounds |language=French}}</ref> The modern industrial variant process instead uses ] (V<sub>2</sub>O<sub>5</sub>) as the catalyst in a ]-phase reaction with naphthalene using ].<ref name=Ullmann/> The overall process involves oxidative cleavage of one of the rings and loss of two of the carbon atoms as ].

An alternative process involves oxidation of the two ]s of ], a more ] process. This reaction is run at about 320–400&nbsp;°C and has the following stoichiometry:
:C<sub>6</sub>H<sub>4</sub>(CH<sub>3</sub>)<sub>2</sub> + 3&nbsp;O<sub>2</sub> → C<sub>6</sub>H<sub>4</sub>(CO)<sub>2</sub>O + 3&nbsp;H<sub>2</sub>O
The reaction proceeds with about 70% selectivity. About 10% of ] is also produced:
:C<sub>6</sub>H<sub>4</sub>(CH<sub>3</sub>)<sub>2</sub> + {{sfrac|7|1|2}}&nbsp;O<sub>2</sub> → C<sub>4</sub>H<sub>2</sub>O<sub>3</sub> + 4&nbsp;H<sub>2</sub>O + 4&nbsp;CO<sub>2</sub>
Phthalic anhydride and maleic anhydride are recovered by distillation by a series of ]s.

The naphthalene route (the '''Gibbs phthalic anhydride process''' or the '''Gibbs–Wohl naphthalene oxidation''' reaction) has declined relative to the ''o''-xylene route.
]-catalyzed oxidation of ] to phthalic anhydride, with ] represented as a molecule versus its true extended structure.<ref>{{cite book|doi=10.1002/9780470638859.conrr270|chapter=Gibbs-Wohl Naphthalene Oxidation|title=Comprehensive Organic Name Reactions and Reagents|year=2010|isbn=9780470638859}}</ref>]]
Phthalic anhydride can also be prepared from ] by simple thermal dehydration above 210°C.<ref name=Ullmann>{{Ullmann|first1=Peter M.|last1=Lorz|first2=Friedrich K. |last2=Towae|first3= Walter|last3=Enke|first4=Rudolf|last4=Jäckh|first5=Naresh|last5= Bhargava|first6=Wolfgang|last6=Hillesheim|display-authors=3|year=2007|doi=10.1002/14356007.a20_181.pub2|isbn=978-3527306732|title=Phthalic Acid and Derivatives}}</ref>

==Uses==
===Phthalate esters plasticizers===
The primary use of phthalic anhydride is a precursor to ]s, used as plasticizers in vinyl chloride. Phthalate esters are derived from phthalic anhydride by the ] reaction.<ref name=Ullmann/> In the 1980s, approximately 6.5&nbsp;million tonnes of these esters were produced annually, and the scale of production was increasing each year, all from phthalic anhydride. The process begins with the reaction of phthalic anhydride with alcohols, giving the monoesters:
:C<sub>6</sub>H<sub>4</sub>(CO)<sub>2</sub>O + ROH → C<sub>6</sub>H<sub>4</sub>(CO<sub>2</sub>H)CO<sub>2</sub>R
The second esterification is more difficult and requires removal of water:
:C<sub>6</sub>H<sub>4</sub>(CO<sub>2</sub>H)CO<sub>2</sub>R + ROH {{eqm}} C<sub>6</sub>H<sub>4</sub>(CO<sub>2</sub>R)<sub>2</sub> + H<sub>2</sub>O
The most important diester is ] ("DEHP"), used in the manufacture of ] compounds.

===Precursor to dyestuffs===
] is a popular dye derived from the condensation of phthalic anhydride and ].]]
Phthalic anhydride is widely used in industry for the production of certain ]. A well-known application of this reactivity is the preparation of the ] dye ] by reaction with ] followed by hydrolysis of the chloride.<ref>{{OrgSynth | author = L. A. Bigelow and H. H. Reynolds | title = Quinizarin | collvol = 1 | collvolpages = 476| year = 1941 | prep = CV1P0476}}</ref> ] can be synthesized by the condensation of phthalic anhydride with two equivalents of ] under acidic conditions (hence the name). It was discovered in 1871 by ].<ref>{{cite journal | author = Baeyer, A. | date = 1871 | title = Ueber eine neue Klasse von Farbstoffen | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 4 | issue = 2 | pages = 555–558 | doi = 10.1002/cber.18710040209 | url = https://zenodo.org/record/1425008 }}</ref><ref>{{cite journal | author = Baeyer, A. | date = 1871 | title = Ueber die Phenolfarbstoffe | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 4 | issue = 2 | pages = 658–665 | doi = 10.1002/cber.18710040247 | url = https://zenodo.org/record/1425010 }}</ref><ref>{{cite journal | author = Baeyer, A. | date = 1871 | title = Ueber die Phenolfarbstoffe | journal = Polytechnisches Journal | volume = 201 | issue = 89 | pages = 358–362 | url = http://dingler.culture.hu-berlin.de/article/pj201/ar201089 }}</ref>
]<ref>Max Hubacher, {{US patent|2192485}} (1940 to Ex Lax Inc)</ref>]]

===Pharmaceuticals===
Phthalic anhydride treated with ] gives ] (CAP), a common ] ] that has also been shown to have antiviral activity.<ref>{{Cite journal| vauthors=Neurath AR |title=Microbicide for prevention of sexually transmitted diseases using a pharmaceutical excipient. |journal= AIDS Patient Care STDs |volume=14 |issue= 4 |pages= 215–9 |year= 2000 |pmid= 10806641 |doi= 10.1089/108729100317830}}</ref> Phthalic anhydride is a degradation product of CAP.<ref>{{Cite journal|vauthors=Mayhew JW, Gideon LT, Ericksen B, Hlavaty JJ, Yeh SM, Chavdarian CG, Strick N, Neurath AR |display-authors=3|title=Development of a gel permeation chromatographic assay to achieve mass balance in cellulose acetate phthalate stability studies. |journal= J Pharm Biomed Anal |volume=49 |issue= 2 |pages= 240–6 |year= 2009 |pmid=19070984 |pmc= 2859192 |doi= 10.1016/j.jpba.2008.10.039}}</ref>

==Reactions==
Phthalic anhydride is a versatile intermediate in ], in part because it is bifunctional and cheaply available.

===Hydrolysis, alcoholysis, ammonolysis===
] by hot water forms ]:<ref>{{cite book | last = Noller | first = Carl R. | title = Chemistry of Organic Compounds |edition=3rd | publisher = W. B. Saunders | year = 1965 | location = Philadelphia | pages = 602 }}</ref>
:C<sub>6</sub>H<sub>4</sub>(CO)<sub>2</sub>O + H<sub>2</sub>O → C<sub>6</sub>H<sub>4</sub>(CO<sub>2</sub>H)<sub>2</sub>
Hydrolysis of anhydrides is not typically a reversible process. Phthalic acid is however easily dehydrated to form phthalic anhydride. Above 180&nbsp;°C, phthalic anhydride re-forms.

] alcohols form half-esters (see above), and these derivatives are often resolvable because they form diastereomeric salts with chiral amines such as ].<ref>{{OrgSynth | author = Joseph Kenyon | title = ''d''- and ''l''-Octanol-2| collvol = 1 | collvolpages = 418| year = 1941 | prep = CV1P0418}}</ref> A related ring-opening reaction involves ]s to give the useful ]:<ref>{{OrgSynth | author = George B. Payne | title = Monoperphthalic acid| collvol = 5 | collvolpages = 805| year = 1973 | prep = CV5P0805}}</ref>
:C<sub>6</sub>H<sub>4</sub>(CO)<sub>2</sub>O + H<sub>2</sub>O<sub>2</sub> → C<sub>6</sub>H<sub>4</sub>(CO<sub>3</sub>H)CO<sub>2</sub>H
] can be prepared by heating phthalic anhydride with aqueous ] giving a 95–97% yield. Alternatively, it may be prepared by treating the anhydride with ] or ]. It can also be produced by ] of ].<ref name=Ullmann/> ] is commercially available and is the potassium salt of phthalimide. It may be prepared by adding a hot solution of phthalimide to a solution of ]; the desired product precipitates.<ref>{{OrgSynth | title = β-Bromoethylphthalimide | collvol = 1 | collvolpages = 119 | prep = cv1p0119 | year = 1941 | author = P. L. Salzberg and J. V. Supniewski}}</ref>

===Preparation of aliphatic nitroalkenes===
Phthalic anhydride is used to dehydrate short-chain ]-]s to yield ]s, compounds with a high tendency to ].<ref>{{cite journal|author1=Ranganathan, Darshan |author2=Rao, Bhushan |author3=Ranganathan, Subramania |author4=Mehrotra, Ashok |author5=Iyengar, Radha |display-authors=3|name-list-style=amp |title=Nitroethylene: a stable, clean, and reactive agent for organic synthesis|journal=The Journal of Organic Chemistry|year=1980|volume=45|issue=7|pages=1185–1189|doi=10.1021/jo01295a003}}</ref>

==Safety==
The most probable human exposure to phthalic anhydride is through skin contact or inhalation during manufacture or use. Studies show that exposure to phthalic anhydride can cause ], chronic ], and ]. Phthalic anhydride's reaction on human health is generally an asthma–rhinitis–] syndrome or a delayed reaction and ]-like symptoms and with increased ] (] and ]) levels in the blood.

==References==
{{reflist}}

==External links==
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{{Authority control}}

{{DEFAULTSORT:Phthalic Anhydride}}
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