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Product Details
Description |
Succinic anhydride, also called di hydro - 2,5- furandione , is an organic compound with the molecular formula C4H4O3.This colorless solid is the acid anhydride of succinic acid. |
Chemical Properties |
fine white crystalline solid |
Uses |
Succinic anhydride is a cyclic anhydride of succinic acid with a five-membered ring. It is widely used in the manufacture of polymeric materials, pharmaceuticals, agrochemicals, dyes, surface-active agents, and organic flame-retardant materials. It also finds application as a cross-linking agent in ion-exchange membranes and a curing agent for epoxy resins. |
Application |
Alkyl succinic anhydride (ASA) is used as a sizing agent or wet strength additive in paper production. |
Production Methods |
The compound is produced from succinic anhydride and hydrogen peroxide . This material must be stabilized by using a dehydrating agent such as disodium sulfate or magnesium sulfate. |
Preparation |
A solution of succinic acid (500 mg, 42 mmol) and triethylamine (1.23 mL, 42 mmol) in anhydrous THF (120 mL) was allowed to react with triphosgene (42 mg, 7.0 mmol) at ice-water temperature for 10 min. The reaction mixture was subsequently stirred for a further 15 min at room temperature. The solution was then filtered, and the filtrate was concentrated to dryness. The residue was crystallized from ethyl acetate to afford the desired product as white crystals (370 mg, 85%). |
Synthesis Reference(s) |
Synthetic Communications, 23, p. 419, 1993 DOI: 10.1080/00397919308009796 |
General Description |
Colorless needles or white crystalline solid. Melting point 237°F. Sublimes at 239°F at 5 mm Hg pressure; and at 198°F and 1 mm Hg pressure. Moderately toxic and an irritant. |
Air & Water Reactions |
Reacts slowly with water. Insoluble in water. |
Reactivity Profile |
Succinic anhydride reacts exothermically with water. Reactions are usually slow, but might become violent if local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases. |
Fire Hazard |
Flash point data for Succinic anhydride are not available, however, Succinic anhydride is probably combustible. |
Flammability and Explosibility |
Notclassified |
Canonical SMILES | C1CC(=O)OC1=O |
XLogP3-AA | -0.5 |
Exact Mass | 100.016043985 g/mol |
Monoisotopic Mass | 100.016043985 g/mol |
Complexity | 102 |
Safety Profile |
Experimental teratogenic effects. Moderately toxic by ingestion. A severe eye irritant. Mutation data reported. Questionable carcinogen with experimental neoplastigenic data. When heated to decomposition it emits acrid smoke and irritating fumes. See also ANHYDRIDES. It's safe for all skin types, including sensitive skin, says Frieling. |
Purification Methods |
Succinic anhydride is manufactured by liquid-phase catalytic hydrogenation of maleic anhydride; succinic acid by hydration of the anhydride. Crystallise the anhydride from redistilled acetic anhydride or CHCl3, then filter, wash with diethyl ether and dry it in a vacuum. [Beilstein 17 H 606, 17 V 6.] |
InChI:InChI=1/C8H10O7/c9-5(10)1-3-7(13)15-8(14)4-2-6(11)12/h1-4H2,(H,9,10)(H,11,12)
In the last decades, a noticeable interest has emerged toward the use of octenyl succinic anhydride (OSA)‐starch to improve the long‐term stability in such systems. In this review, …
Octenyl succinic anhydride is an unsaturated cyclic anhydride that undergoes esterification with hydroxyl containing species under basic conditions.
2-bromomalonic acid
thiophenol
succinic acid anhydride
hydrogen bromide
diphenyldisulfane
Conditions | Yield |
---|---|
|
2-bromomalonic acid
thiophenol
benzene
succinic acid anhydride
hydrogen bromide
diphenyldisulfane
Conditions | Yield |
---|---|
|
pyridine
diethyl ether
hydrogen cyanide
succinoyl dichloride
4-oxo-4-(1-pyrrolidinyl)butanoic acid
Dimethyl succinate
butane-4'-carboxy-(1'-piperidinyl)-carboxamide
4-oxo-4-thiophen-2-yl-butyric acid
CAS:120-74-1
Molecular Formula:C<sub>8</sub>H<sub>10</sub>O<sub>2</sub>
Molecular Weight:138.16
CAS:716-39-2