Succinic anhydride
- BSA
- Dihydro -2 ,5- furandione
- Oxolane -2 ,5- dione ( IUPAC)
- Butandisäureanhydrid
- 2.5 Diketotetrahydrofuran
- Succinicanhydrid
- Succinyloxid
Colorless, pungent-smelling needles / crystals
Fixed
1.23 g · cm -3
119 ° C.
261 ° C
1.2 hPa (92 ° C)
- Default under hydrolysis in water ( 67 g · l-1 at 20 ° C)
- Soluble in chloroform and ethanol
Attention
1510 mg · kg -1 ( LD50, rat, oral)
-608.6 KJ / mol
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Succinic anhydride is a heterocyclic organic chemical compound and the acid anhydride of the succinic acid.
Production and representation
Succinic anhydride can be obtained by reaction of succinic acid and acetic anhydride, acetyl chloride or phosphorus oxychloride. To succinic anhydride also forms during heating of succinic acid above 200 ° C. The compound can also be obtained by the catalytic hydrogenation of maleic anhydride.
Properties
Physical Properties
Succinic anhydride is a white flammable solid which melts at 119-120 ° C. At atmospheric pressure, the compound boils at 261 ° C. In the vacuum sublimated the connection. The vapor pressure function is given by Antoine corresponding log10 (P) = A- ( B / ( T C )) ( P in bar, T in K) with A = 3.65221, B = 1433.874 and C = -144.107 in temperature range of 365 K to 534 K. The solubility in water at 20 ° C. 67 g · l - 1 where there is a slow hydrolysis. The aqueous solution is acidic. In aromatic hydrocarbons, the solubility is relatively low. They amount in toluene 10 g · l - 1, styrene 11 g · l -1, in ethylbenzene 8 g · l -1 and in cumene 5 g · l -1. The heat of formation of the solid is -608.6 kJ · mol -1. For the heat of combustion of -1537.1 kJ, a value · mol -1 was determined.
Chemical Properties
Succinic anhydride can be hydrolyzed in the presence of sodium hydroxide solution to the succinic acid. In dioxane / water reaction heat of -46.86 kJ · mol -1 was determined at 30 ° C. The reaction with alcohols gives the corresponding succinic acid half ester. The compound can be used as a reagent for Friedel- Crafts acylations. The reaction with benzene produces here the γ - oxo carboxylic acid β - benzoylpropionic. From Grignard compounds and succinic anhydride γ - oxocarboxylic acid ester can also be easily obtained. The reaction with ammonia at higher temperatures results in the succinimide. At higher temperatures, the substance is flammable, but it reacts violently with oxidizing substances. The melt forms flammable vapor - air mixtures. The flash point is 157 ° C.
Health Hazards
The consequences of contact or inhalation of succinic anhydride are irritating to the skin and respiratory tract, the mucous membranes may ignite. The compound was detected as a component in the main flow of a filterless cigarette.
Use
Succinic anhydride is used as the chemical synthesis of other chemical compounds, such as in multi-stage syntheses of tetralone, 1-naphthol, tetralin and naphthalene, and N- chloro and N -bromosuccinimide. The industrial production of citraconic ( methylmaleic ) anhydride is effected by reacting with formaldehyde. The compound is (formally ) an output connection for an alkylated succinic anhydride, which is used in the paper industry as sizing agents. The synthesis takes place, however via maleic anhydride and a long-chain alkene.