Succinic anhydride









































Succinic anhydride

Skeletal formula of succinic anhydride
Names

Preferred IUPAC name
Oxolane-2,5-dione[1]

Other names
3,4-Dihydrofuran-2,5-dione, Butanedioic anhydride[1]
Dihydrofuran-2,5-dione
Succinic acid anhydride
Succinyl oxide
Dihydro-2,5-furandione

Identifiers

CAS Number



  • 108-30-5 ☑Y


3D model (JSmol)


  • Interactive image


ChEBI


  • CHEBI:36595 ☑Y


ChemSpider


  • 7634 ☑Y


ECHA InfoCard

100.003.246

KEGG


  • C19524 ☒N



PubChem CID


  • 7922


UNII


  • 6RF4O17Z8J ☒N





Properties

Chemical formula


C4H4O3

Molar mass
100.07 g·mol−1
Appearance
Colorless crystalline needles[2]

Density
1.23 g/cm3[2]

Melting point
 119 to 120 °C (246 to 248 °F; 392 to 393 K)[3]

Boiling point
 261 °C (502 °F; 534 K)[2]

Solubility in water

Decomposes


Magnetic susceptibility (χ)

-47.5·10−6 cm3/mol
Hazards

Flash point
 147 °C (297 °F; 420 K)[4]
Lethal dose or concentration (LD, LC):


LD50 (median dose)

1510 mg/kg (oral, rat)[4]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).


☒N verify (what is ☑Y☒N ?)

Infobox references


Succinic anhydride, is an organic compound with the molecular formula (CH2CO)2O. This colorless solid is the acid anhydride of succinic acid.




Contents





  • 1 Preparation


  • 2 Reactions


  • 3 Related compounds


  • 4 See also


  • 5 References




Preparation


In the laboratory, this material can be prepared by dehydration of succinic acid. Such dehydration can occur with the aid of acetyl chloride or phosphoryl chloride,[5] or thermally.[6]


Industrially, succinic anhydride is prepared by catalytic hydrogenation of maleic anhydride.[6]



Reactions


Succinic anhydride hydrolyzes readily to give succinic acid:


(CH2CO)2O + H2O → (CH2CO2H)2

With alcohols (ROH), a similar reaction occurs, delivering the monoester:


(CH2CO)2O + ROH → RO2CCH2CH2CO2H


Related compounds




Chemical structure of an alkylsuccinic anhydride derived from octadecene.


Maleic anhydride undergoes the Alder-ene reaction with olefins to give alkenylsuccinic anhydrides. Such compounds are sizing agents in the paper industry. In this role, the anhydride is proposed to form an ester with the hydroxyl groups on the cellulose fibers.[7] Maleic anhydride undergoes a similar reaction with polyisobutylene to give polyisobutylenylsuccinic anhydride, a common building block chemical in the petroleum additives industry.



See also


  • Maleic anhydride


References




  1. ^ ab Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 835. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4..mw-parser-output cite.citationfont-style:inherit.mw-parser-output .citation qquotes:"""""""'""'".mw-parser-output .citation .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-ws-icon abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center.mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-maintdisplay:none;color:#33aa33;margin-left:0.3em.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em


  2. ^ abc Record of CAS RN 108-30-5 in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 27 April 2010.


  3. ^ McLean, Andrew; Adams, Roger (1936). "Succinic-α-d2,α'-d2 Acid and its Derivatives". J. Am. Chem. Soc. 58 (5): 804. doi:10.1021/ja01296a038.


  4. ^ ab Chemical data


  5. ^ Louis F. Fieser, E. L. Martin, R. L. Shriner, and H. C. Struck (1932). "Succinic Anhydride". Organic Syntheses. 12: 66.CS1 maint: Multiple names: authors list (link); Collective Volume, 2, p. 560


  6. ^ ab Carlo Fumagalli. (2006), "Succinic Acid and Succinic Anhydride", Kirk-Othmer Encyclopedia of Chemical Technology, New York: John Wiley, doi:10.1002/0471238961.1921030306211301.a01.pub2, ISBN 9780471238966


  7. ^ Gess, Jerome; Rend, Dominic (2005). "Alkenyl Succinic Anhydride (ASA)". Tappi Journal. 4: 25–30.









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