Succinic anhydride
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470483208
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile1 = Dihydrofuran-2,5-dione 200.svg
| ImageClass1 = skin-invert-image
| ImageSize1 = 130
| ImageAlt1 = Skeletal formula of succinic anhydride
| ImageFile2 = Succinic-anhydride-from-xtal-3D-bs-17.png
| ImageClass2 = bg-transparent
| ImageSize2 = 130
| PIN = Oxolane-2,5-dione{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 835 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}
| OtherNames = 3,4-Dihydrofuran-2,5-dione, Butanedioic anhydride
Dihydrofuran-2,5-dione
Succinic acid anhydride
Succinyl oxide
Dihydro-2,5-furandione
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7634
| InChI = 1/C4H4O3/c5-3-1-2-4(6)7-3/h1-2H2
| InChIKey = RINCXYDBBGOEEQ-UHFFFAOYAN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H4O3/c5-3-1-2-4(6)7-3/h1-2H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RINCXYDBBGOEEQ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 108-30-5
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 6RF4O17Z8J
| PubChem = 7922
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C19524
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 36595
| SMILES = O=C1OC(=O)CC1
}}
|Section2={{Chembox Properties
| C=4 | H=4 | O=3
| Appearance = Colorless crystalline needles
| MeltingPtC = 119 to 120
| BoilingPtC = 261
| BoilingPt_ref = {{GESTIS|Name= |ZVG=33430|CAS=108-30-5|Date=27 April 2010}}
| Solubility = Decomposes
| MagSus = −47.5·10−6 cm3/mol
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPtC = 147
| FlashPt_ref = [http://www.chemicalland21.com/specialtychem/perchem/SUCCINIC%20ANHYDRIDE.htm Chemical data]
| AutoignitionPt =
| LD50 = 1510 mg/kg (oral, rat)
}}
}}
Succinic anhydride, is an organic compound with the molecular formula (CH2CO)2O. This colorless solid is the acid anhydride of succinic acid.
Preparation
In the laboratory, this material can be prepared by dehydration of succinic acid. Such dehydration can occur with the help of acetyl chloride or phosphoryl chloride,{{OrgSynth|author=Louis F. Fieser, E. L. Martin, R. L. Shriner, and H. C. Struck |year=1932 |title=Succinic Anhydride |volume=12 |pages=66 |collvol=2 |collvolpages=560 |prep=CV2P0560}} or thermally.
Industrially, succinic anhydride is prepared by catalytic hydrogenation of maleic anhydride.{{Kirk-Othmer | title = Succinic Acid and Succinic Anhydride | author = Carlo Fumagalli | doi = 10.1002/0471238961.1921030306211301.a01.pub2 | year = 2006 | mode = cs1}}
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
Succinic anhydride is used in acylations under Friedel-Crafts conditions, as illustrated by the industrial route to the drug Fenbufen.Castillo, Rafael; Suárez-Herrera, Margarita; Aparicio, Mayra; Hernández-Lui, Francisco; Hernández, Alicia (1995). "An Improved Synthesis of Fenbulen". Organic Preparations and Procedures International. 27 (5): 550–552. doi:10.1080/00304949509458497.
Related compounds
File:AlkylsuccinicAnhydrideC18again.png
Maleic anhydride undergoes the Alder-ene reaction with alkenes 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.{{cite journal|journal=TAPPI Journal|volume=4|year=2005|pages=25–30|author1=Gess, Jerome|author2= Rend, Dominic|title=Alkenyl Succinic Anhydride (ASA)}} Maleic anhydride undergoes a similar reaction with polyisobutylene to give polyisobutylenylsuccinic anhydride, a common building block chemical in the petroleum additives industry.
Drugs List
Succinic anhydride is used in the synthesis of the following list of agents:
- Haloperidol
- Oxaprozin
- Procodazole
- Endixaprine
- Clofilium phosphate
- Indolidan
- Lometraline
- McN 4612-z
- Fenbufen
- Furobufen
- NNC 38-1049
- Piretanide
- Pirisudanol
- Cinazepam
- Bucloxic acid
- Exatecan
- Blarcamesine
- Ibutilide
- Diclomezine
- Domipizone
- Daminozide
- Trepibutone
- Benfurodil hemisuccinate
- Tepoxalin
- Menbutone
- Florantyrone
- Artesunate
- Suxibuzone
- Sunepitron
- Prizidilol
- Xemilofiban
- Sulfasuccinamide
- Succisulfone