Succinic anhydride

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Succinic anhydride
Dihydrofuran-2,5-dione 200.svg
Succinic-anhydride-from-xtal-3D-bs-17.png
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.246 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C4H4O3/c5-3-1-2-4(6)7-3/h1-2H2 Yes check.svgY
    Key: RINCXYDBBGOEEQ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H4O3/c5-3-1-2-4(6)7-3/h1-2H2
    Key: RINCXYDBBGOEEQ-UHFFFAOYAN
  • O=C1OC(=O)CC1
Properties
C4H4O3
Molar mass 100.073 g·mol−1
AppearanceColorless 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]
Decomposes
-47.5·10−6 cm3/mol
Hazards
Flash point 147 °C (297 °F; 420 K) [4]
Lethal dose or concentration (LD, LC):
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).
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Succinic anhydride, is an organic compound with the molecular formula (CH2CO)2O. This colorless solid is the acid anhydride of succinic acid.

Contents

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, [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

Succinic anhydride is used in acylations under Friedel-Crafts conditions, as illustrated by the industrial route to the drug Fenbufen. [7]

Chemical structure of an alkylsuccinic anhydride derived from octadecene AlkylsuccinicAnhydrideC18again.png
Chemical structure of an alkylsuccinic anhydride derived from octadecene

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. [8] 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:

  1. Haloperidol
  2. Oxaprozin
  3. Procodazole
  4. Endixaprine
  5. Clofilium phosphate
  6. Indolidan
  7. Lometraline
  8. McN 4612-z
  9. Fenbufen
  10. Furobufen
  11. NNC 38-1049
  12. Piretanide
  13. Pirisudanol
  14. Cinazepam
  15. Bucloxic acid
  16. Exatecan
  17. Blarcamesine
  18. Ibutilide
  19. Diclomezine
  20. Domipizone
  21. Daminozide
  22. Trepibutone
  23. Benfurodil hemisuccinate
  24. Tepoxalin
  25. Menbutone
  26. Florantyrone
  27. Artesunate
  28. Suxibuzone
  29. Sunepitron
  30. Prizidilol
  31. Xemilofiban
  32. Sulfasuccinamide
  33. Succisulfone

See also

Related Research Articles

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<span class="mw-page-title-main">Ester</span> Compound derived from an acid

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<span class="mw-page-title-main">Ketene</span> Organic compound of the form >C=C=O

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<span class="mw-page-title-main">Phthalic anhydride</span> Chemical compound

Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. 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 plasticizers for plastics. In 2000, the worldwide production volume was estimated to be about 3 million tonnes per year.

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In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group. The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH3CH2C≡N is called "propionitrile". The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.

<span class="mw-page-title-main">Acyl halide</span> Oxoacid compound with an –OH group replaced by a halogen

In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

<span class="mw-page-title-main">Imide</span> Class of chemical compounds

In organic chemistry, an imide is a functional group consisting of two acyl groups bound to nitrogen. The compounds are structurally related to acid anhydrides, although imides are more resistant to hydrolysis. In terms of commercial applications, imides are best known as components of high-strength polymers, called polyimides. Inorganic imides are also known as solid state or gaseous compounds, and the imido group (=NH) can also act as a ligand.

<span class="mw-page-title-main">Acetic anhydride</span> Organic compound with formula (CH₃CO)₂O

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<span class="mw-page-title-main">Acetyl chloride</span> Organic compound (CH₃COCl)

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Thionyl chloride is an inorganic compound with the chemical formula SOCl2. It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons.

<span class="mw-page-title-main">Organic acid anhydride</span> Any chemical compound having two acyl groups bonded to the same oxygen atom

An organic acid anhydride is an acid anhydride that is also an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O))2O. Symmetrical acid anhydrides of this type are named by replacing the word acid in the name of the parent carboxylic acid by the word anhydride. Thus, (CH3CO)2O is called acetic anhydride.Mixed (or unsymmetrical) acid anhydrides, such as acetic formic anhydride (see below), are known, whereby reaction occurs between two different carboxylic acids. Nomenclature of unsymmetrical acid anhydrides list the names of both of the reacted carboxylic acids before the word "anhydride" (for example, the dehydration reaction between benzoic acid and propanoic acid would yield "benzoic propanoic anhydride").

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Maleic acid or cis-butenedioic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. Its chemical formula is HO2CCH=CHCO2H. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. Maleic acid is mainly used as a precursor to fumaric acid, and relative to its parent maleic anhydride, which has many applications.

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Diketene is an organic compound with the molecular formula C4H4O2, and which is sometimes written as (CH2CO)2. It is formed by dimerization of ketene, H2C=C=O. Diketene is a member of the oxetane family. It is used as a reagent in organic chemistry. It is a colorless liquid.

<span class="mw-page-title-main">Trifluoroacetic anhydride</span> Chemical compound

Trifluoroacetic anhydride (TFAA) is the acid anhydride of trifluoroacetic acid. It is the perfluorinated derivative of acetic anhydride.

References

  1. 1 2 "Front Matter". 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.
  2. 1 2 3 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. 1 2 Chemical data
  5. Louis F. Fieser, E. L. Martin, R. L. Shriner, and H. C. Struck (1932). "Succinic Anhydride". Organic Syntheses . 12: 66{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 2, p. 560.
  6. 1 2 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. 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.
  8. Gess, Jerome; Rend, Dominic (2005). "Alkenyl Succinic Anhydride (ASA)". TAPPI Journal. 4: 25–30.