108-30-5

Basic information

• Product Name: Succinic anhydride
• Synonyms: 2,5(3H,4H)-Furandione;5-Furandione,dihydro-2;bernsteinsaureanhydrid;Bernsteinsaure-anhydrid;dihydro-5-furandione;Dihydro-furan-2,5-dione;NCI-C55696;Oxolan-2,5-dione
• CAS NO: 108-30-5
• Molecular Formula: C₄H₄O₃
• Molecular Weight: 100.07
• EINECS: 203-570-0
• Product Categories: SuccinicSeries;Heterocycles;Isotope Labelled Compounds;Building Blocks;Carbonyl Compounds;Carboxylic Acid Anhydrides;Chemical Synthesis;Organic Building Blocks;Fine chemicals
• Mol File: 108-30-5.mol
• Article Data: 196

Chemical Properties

• Melting Point: 118-120 °C(lit.)
• Boiling Point: 261 °C(lit.)
• Flash Point: 157°C
• Appearance: fine white crystalline solid
• Density: 1,572 g/cm3
• Vapor Density: 3.5 (vs air)
• Vapor Pressure: 1 mm Hg ( 92 °C)
• Refractive Index: 1.4688 (estimate)
• Storage Temp.: Store at 0-5°C
• Solubility: 62.9g/l Hydrolysis
• PKA: 4.67[at 20 ℃]
• Water Solubility: <0.1 g/100 mL at 21℃ (decomposes)
• Sensitive: Moisture Sensitive
• Stability: Stable. Incompatible with oxidising agents, strong acids, strong bases, alcohols, amines. Avoid exposure to water or moisture.
• Merck: 14,8870
• BRN: 108441
• CAS DataBase Reference: Succinic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: Succinic anhydride(108-30-5)
• EPA Substance Registry System: Succinic anhydride(108-30-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37-22
• Safety Statements: 25-46
• RIDADR: UN 3261 8 / PGII
• WGK Germany: 1
• RTECS: WN0875000
• F: 21
• TSCA: Yes
• Hazardous Substances Data: 108-30-5(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 108-30-5 differently. You can refer to the following data:
1. It was used in the preparation of covalently cross-linked oxidized-alginate/N-succinyl-chitosan hydrogels, as injectable systems towards tissue engineering.It was also used in preparing functionalized oxide surfaces on a chip.
2. Succinic Anhydride is an acidulant that hydrolyzes very slowly to succinic acid in water. it has thermal stability and a low melting point of 118°c which permits it to be used in products at compara- tively low temperatures. it is used as a leavening acidulant for bak- ing powder.
3. Succinic Anhydride is a useful compound in the paper manufacturing process.

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

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.

Purification Methods

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)

Synthetic route

maleic anhydride (108-31-6) → succinic acid anhydride (108-30-5)

Conditions	Yield
With acetic anhydride; zinc In toluene at 40 - 86℃; for 48h; Reagent/catalyst; Inert atmosphere; chemoselective reaction;	100%
With fac-[Mn(1,2-bis(di-isopropylphosphino)ethane)(CO)3(CH2CH2CH3)]; hydrogen In tetrahydrofuran; dichloromethane at 60℃; under 37503.8 Torr; for 24h;	99%
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide In tetrahydrofuran for 0.0833333h; Ambient temperature;	96%

succinic acid (110-15-6) → succinic acid anhydride (108-30-5)

Conditions	Yield
With acetic anhydride at 80℃; for 2h;	100%
at 240℃; under 180 Torr; Rate constant; Equilibrium constant; var. temperature, var. pressure;	97%
2,6-bis[(2,2,6,6-tetramethylpiperidin-1-yl)methyl]phenylboronic acid In butryonitrile for 12h; Reflux;	96%

carbon monoxide (201230-82-2) + methyloxirane (75-56-9, 16033-71-9) → succinic acid anhydride (108-30-5)

Conditions	Yield
With [(tetra(4-chlorophenyl)porphyrinato)aluminium(III)bis(tetrahydrofuran)][tetracarbonylcobaltate] In 1,4-dioxane at 90℃; under 43958.7 Torr; for 3h;	98%

maleic anhydride (108-31-6) + WH2(η-cyclopentadienyl)2 → succinic acid anhydride (108-30-5) + (C5H5)2W(C4H2O3)

Conditions	Yield
In toluene Irradiation (UV/VIS); (Ar); addn. of maleic anhydride to soln. of W-compd. in toluene portionwise, irradn. (500 W Hg-lamp, 550 nm, 58 h); removal of solid product by centrifugation, recrystn. (CH3CN); elem. anal.;	A 95% B 22%

succinamic acid (638-32-4) + ortho-bromophenylacetic acid (18698-97-0) → succinic acid anhydride (108-30-5)

Conditions	Yield
With nitromethane; copper(l) chloride at 75℃; for 5h; Concentration; Temperature;	91%

oxirane (75-21-8) + carbon monoxide (201230-82-2) → succinic acid anhydride (108-30-5) + β-Propiolactone (57-57-8)

Conditions	Yield
Hexamethylbenzene; [(C1TPP)Al][Co(CO)4] In tetrahydrofuran at -78 - 60℃; under 31029.7 Torr; for 3h; Product distribution / selectivity; Molecular sieve; Inert atmosphere;	A 8% B 88%
Hexamethylbenzene; [(C1TPP)Al][Co(CO)4] In tetrahydrofuran at -78 - 60℃; under 31029.7 Torr; for 3h; Product distribution / selectivity; Molecular sieve; Inert atmosphere;	A 13% B 81%
With Hexamethylbenzene; [(tetra(4-chlorophenyl)porphyrinato)aluminium(III)][tetracarbonylcobaltate] In tetrahydrofuran at 60℃; under 31029.7 Torr; for 3h; Glovebox; Inert atmosphere;	A 8 %Spectr. B 88 %Spectr.

succinoyl dichloride (543-20-4) → succinic acid anhydride (108-30-5)

Conditions	Yield
With pyridine; 1,1,1-trichloro-3,3,3-trifluoro-propan-2-one; water In toluene for 0.5h; Ambient temperature;	85%
With diethyl ether; sodium acetate
With oxalic acid

L-proline (147-85-3) → Succinimide (123-56-8) + succinic acid anhydride (108-30-5)

Conditions	Yield
With dihydrogen peroxide; sodium hydroxide In water for 50h; pH=10; Reflux;	A 81% B 19%

maleic anhydride (108-31-6) → 4-butanolide (96-48-0) + succinic acid anhydride (108-30-5)

Conditions	Yield
With hydrogen at 180℃; under 7500.75 Torr; for 2h; Pressure; Temperature;	A n/a B 79.87%
With hydrogen at 150℃; under 7500.75 Torr;	A n/a B 78.36%
With hydrogen at 250℃; Conversion of starting material;

tetrahydrofuran (109-99-9) → 4-butanolide (96-48-0) + 5-hydroxydihydrofuran-2(3H)-one (50768-69-9) + succinic acid anhydride (108-30-5)

Conditions	Yield
With 2,6-dichloropyridine N-oxide; dichloro(5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)ruthenium(IV) In 1,2-dichloro-ethane at 40℃; for 20h; Inert atmosphere;	A 69% B 22% C 5%

oxirane (75-21-8) + carbon monoxide (201230-82-2) → succinic acid anhydride (108-30-5) + acetaldehyde (75-07-0)

Conditions	Yield
In 1,4-di-tert-butylbenzene at 20 - 80℃; under 10343.2 - 31029.7 Torr; for 0.666667h;	A 62.7% B 7.9%
With [(tetra(4-chlorophenyl)porphyrinato)aluminium(III)bis(tetrahydrofuran)][tetracarbonylcobaltate] at 80℃; under 31029.7 Torr; for 2h; Catalytic behavior; Pressure; Reagent/catalyst; Glovebox; Inert atmosphere;	A 68.8 %Spectr. B 5.4 %Spectr.

(1,2-bis(diphenylphosphino)ethane)Ni(C2H4CO2) → succinic acid anhydride (108-30-5) + Ni(CO)2{1,2-bis(diphenylphosphino)ethane} (15793-01-8)

Conditions	Yield
With carbon monoxide In dichloromethane Schlenk tube contg. CH2Cl2 soln. of educt evacuated and 1 atm of CO introduced; analyzed by GLC, GC-mass, and IR;	A 55% B n/a

maleic anhydride (108-31-6) + 2-methoxyacetic acid (625-45-6) → succinic acid anhydride (108-30-5) + (methoxymethyl)succinic anhydride

Conditions	Yield
With titanium(IV) oxide In acetonitrile for 18h; UV-irradiation; Inert atmosphere;	A 16% B 54%

n-butane (106-97-8) → succinic acid anhydride (108-30-5)

Conditions	Yield
With triethyl phosphate; water; vanadium-containing catalyst at 393 - 455℃; Gas phase;	51.5%
With vanadium phosphorus oxide supported on TiO2 or SiO2; oxygen at 450℃;
With V-P-Co-O at 450℃; for 8.33333E-05h; Product distribution; Rate constant; various catalysts under different conditions;

maleic anhydride (108-31-6) → 4-butanolide (96-48-0) + succinic acid anhydride (108-30-5) + butan-1-ol (71-36-3)

Conditions	Yield
With hydrogen In 1,4-dioxane at 159.84℃; under 37503.8 Torr; Autoclave;	A 49.73% B 35.07% C 12.66%

formaldehyd (50-00-0) + Dimethyl succinate (106-65-0) → succinic acid anhydride (108-30-5) + methyl hydrogen succinate (3878-55-5) + citraconic acid anhydride (616-02-4) + carbon dioxide (124-38-9)

Conditions	Yield
With gamma-alumina In methanol; water at 380℃; under 3750.38 Torr; Kinetics; Concentration; Temperature; Stobbe Condensation; Autoclave; Flow reactor;	A 8% B 18% C 30% D 10%

1,3,5-Trioxan (110-88-3) + methyl hydrogen succinate (3878-55-5) → succinic acid anhydride (108-30-5) + citraconic acid anhydride (616-02-4) + carbon dioxide (124-38-9) + Dimethyl succinate (106-65-0)

Conditions	Yield
With gamma-alumina at 380℃; under 3750.38 Torr; Stobbe Condensation; Autoclave; Flow reactor;	A 9% B 23% C 15% D 30%

1,3,5-Trioxan (110-88-3) + Dimethyl succinate (106-65-0) → succinic acid anhydride (108-30-5) + methyl hydrogen succinate (3878-55-5) + citraconic acid anhydride (616-02-4) + carbon dioxide (124-38-9)

Conditions	Yield
With gamma-alumina at 380℃; under 3750.38 Torr; Temperature; Pressure; Stobbe Condensation; Autoclave; Flow reactor;	A 8% B 19% C 26% D 18%

maleic anhydride (108-31-6) + Trimethylacetic acid (75-98-9) → succinic acid anhydride (108-30-5) + 2-tert-butylsuccinic anhydride (52685-36-6)

Conditions	Yield
With titanium(IV) oxide In acetonitrile for 26h; UV-irradiation; Inert atmosphere;	A 20% B 16%

2,3-bis(trimethylsilyl)-1,3-butadiene-1,4-dione (145178-53-6) → succinic acid anhydride (108-30-5) + (Z)-2,3-bis(trimethylsilyl)succinic anhydride

Conditions	Yield
With water In acetone at 22℃; for 0.5h;	A n/a B 15%

pyridine (110-86-1) + diethyl ether (60-29-7) + hydrogen cyanide (74-90-8) + succinoyl dichloride (543-20-4) → succinic acid anhydride (108-30-5) + Succinyl Dicyanide (63979-84-0)

maleic anhydride (108-31-6) + ethyl acetate (141-78-6) → succinic acid anhydride (108-30-5)

Conditions	Yield
at 20℃; Hydrogenation;

tetrachloromethane (56-23-5) + peroxydicuccinic acid (123-23-9) → succinic acid anhydride (108-30-5) + Adipic acid (124-04-9)

chloroform (67-66-3) + 1,2-diisopropylidene-cyclobutane (3642-16-8) → Tetramethyl-[1,2,4,5]tetroxan (1073-91-2) + succinic acid anhydride (108-30-5) + acetone (67-64-1)

Conditions	Yield
at -20℃; bei der Ozonisation;

(E)-1,2-dichloro-1-ethoxy-ethene (42345-82-4) + succinic acid (110-15-6) → succinic acid anhydride (108-30-5) + chloroacetic acid ethyl ester (105-39-5)

succinic acid (110-15-6) → succinic acid anhydride (108-30-5) + 4-Ketopimelic acid (502-50-1)

Conditions	Yield
5-6 h Erhitzen der Schmelze; anschliessend Eindampfen mit konz. HCl;

ethyl 3-(chloroformyl)propionate (14794-31-1) → succinic acid anhydride (108-30-5) + chloroethane (75-00-3)

Conditions	Yield
bei der Destillation unter vermindertem Druck;

L-menthylsuccinic acid (77341-67-4) → succinic acid anhydride (108-30-5) + menthol (89-78-1)

Conditions	Yield
at 300℃;

oxalic acid (144-62-7) + succinoyl dichloride (543-20-4) → succinic acid anhydride (108-30-5)

succinic acid (110-15-6) + acetic anhydride (108-24-7) → succinic acid anhydride (108-30-5)

Conditions	Yield
beim Schuetteln der waessr. Loesung von bernsteinsaurem Natrium;
at 120 - 150℃; unter Druck;

pyrrolidine (123-75-1) + succinic acid anhydride (108-30-5) → 4-oxo-4-(1-pyrrolidinyl)butanoic acid (69338-35-8)

Conditions	Yield
In acetonitrile at 20℃;	100%
In chloroform for 1h; Heating;	83%
With diethyl ether
Reflux;
In toluene for 2.5h; Reflux;

succinic acid anhydride (108-30-5) + methanol (67-56-1) → methyl hydrogen succinate (3878-55-5)

Conditions	Yield
at 20℃;	100%
at 64 - 68℃; for 3.8h;	98.5%
at 70℃; for 2h;	98%

succinic acid anhydride (108-30-5) + oleoyl alcohol (143-28-2) → oleyl hemisuccinate (20060-41-7)

Conditions	Yield
With dmap In dichloromethane at 20℃; for 14h; Inert atmosphere;	100%
at 120℃;
In pyridine at 20℃;

succinic acid anhydride (108-30-5) + 1-Hexadecanol (36653-82-4) → hexadecanol monosuccinate (50893-80-6)

Conditions	Yield
With dmap In dichloromethane at 20℃; for 14h; Inert atmosphere;	100%
With dmap In toluene at 110℃; for 1.5h;	79.4%
With pyridine	42%

succinic acid anhydride (108-30-5) + Cholestanol (80-97-7) → succinic acid mono-3β-cholestanyl ester (84597-57-9)

Conditions	Yield
With triethylamine In pyridine; dichloromethane for 144h;	100%
With dmap; triethylamine In ethyl acetate at 95℃; for 5h;	47.8%
With pyridine

succinic acid anhydride (108-30-5) + cyclohexylamine (108-91-8) → 4-(cyclohexylamine)-4-oxobutanoic acid (21451-32-1)

Conditions	Yield
Stage #1: succinic acid anhydride; cyclohexylamine In N,N-dimethyl acetamide at 20℃; for 24h; Stage #2: In N,N-dimethyl acetamide; xylene at 140℃; for 48h;	100%
In 1,4-dioxane at 80℃; for 0.5h;	90%
In dichloromethane at 20℃; for 0.333333h;	89%

succinic acid anhydride (108-30-5) + 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → N-<2-(3,4-dimethoxyphenyl)ethyl>succinimide (39662-45-8)

Conditions	Yield
With acetic acid for 24h; Reflux;	100%
Stage #1: succinic acid anhydride; 2-(3,4-dimethoxyphenyl)-ethylamine In ethyl acetate at 20℃; for 0.5h; Stage #2: With acetyl chloride In toluene for 1h; Reflux;	84%
With benzene und Erhitzen des Reaktionsprodukts mit Acetanhydrid unter Zusatz von wenig Pyridin;

succinic acid anhydride (108-30-5) + phenylhydrazine (100-63-0) → 4-oxo-4-(2-phenylhydrazinyl)butanoic acid (14580-01-9)

Conditions	Yield
In acetonitrile at 20℃; for 24h;	100%
With ethanol

succinic acid anhydride (108-30-5) + erythromycin (114-07-8) → 2'-O-(3-carboxypropanoyl) erythromycin (20057-07-2)

Conditions	Yield
In acetone at 50℃;	100%
With acetone
With dichloromethane

succinic acid anhydride (108-30-5) + tert-butylamine (75-64-9) → 4-(tert-butylamino)-4-oxobutanoic acid (6622-06-6)

Conditions	Yield
Stage #1: succinic acid anhydride; tert-butylamine In N,N-dimethyl acetamide at 20℃; for 24h; Stage #2: In N,N-dimethyl acetamide; xylene at 140℃; for 48h;	100%
In dichloromethane at 20℃; for 1h;	52%
Stage #1: succinic acid anhydride; tert-butylamine In dichloromethane at 20℃; for 1h; Stage #2: With sodium hydroxide In water at 20℃; for 2h; Stage #3: With hydrogenchloride In water at 0℃;	52%

succinic acid anhydride (108-30-5) + allyl alcohol (107-18-6) → 4-(allyloxy)-4-oxobutanoic acid (3882-09-5)

Conditions	Yield
With dmap In toluene for 5h; Heating;	100%
With dmap In toluene for 4h; Heating;	90%
With dmap In toluene for 4h; Reflux;	89%

succinic acid anhydride (108-30-5) + 2-(Trimethylsilyl)ethanol (2916-68-9) → 4-oxo-4-(2-(trimethylsilyl)ethoxy)butanoic acid (93790-78-4)

Conditions	Yield
With dmap; 1-hydroxy-pyrrolidine-2,5-dione; triethylamine In toluene for 1.5h; Heating;	100%
With dmap In toluene for 14h; Reflux;	99%
With pyridine In dichloromethane	81%

succinic acid anhydride (108-30-5) + 4-amino-phenol (123-30-8) → 4-(4'-hydroxy-phenylamino)-4-oxo-butanoic acid (62558-67-2)

Conditions	Yield
With sodium dodecyl-sulfate In methanol; water at 20℃; for 0.583333h;	100%
With sodium dodecyl-sulfate In water	87%
In water at 50℃;	86%

Upstream product

• 108-31-6 Maleic anhydride 
• 123-91-1 1,4-Dioxane 
• 119-64-2 1,2,3,4-Tetrahydronaphthalene 
• 10025-87-3 Phosphorus oxychloride 
• 1333-74-0 Hydrogen 

Downstream Products

• 3878-55-5 MONO-METHYL SUCCINATE 
• 130198-76-4 METHYL 4-(4-(BIS(2-HYDROXYETHYL)AMINO)PHENYL)BUTYRATE 
• 3984-34-7 3-(4-Chlorobenzoyl)propionic acid 
• 88495-63-0 Artesunate 
• 366-77-8 3-(4-FLUOROBENZOYL)PROPIONIC ACID 
• 15118-60-2 4-(4-Aminophenyl)butyric acid 
• 3153-44-4 3-(4-METHOXYBENZOYL)PROPIONIC ACID 
• 22373-75-7 (4S)-HYDROXY-3-METHYL-2-(2-PROPENYL)-2-CYCLOPENTENE-1-ONE 
• 110-40-7 Diethyl sebacate 
• 36330-85-5 Fenbufen 
• 14794-31-1 Ethyl Succinyl Chloride 
• 1264-62-6 Erythromycin ethylsuccinate 
• 1596-84-5 Daminozide 
• 84243-58-3 IMAZODAN 
• 5473-15-4 3-(4-ACETYLAMINOBENZOYL)PROPANOIC ACID 
• 62865-36-5 DICLOMEZINE 
• 4653-11-6 4-(2-THIENYL)BUTYRIC ACID 
• 79481-83-7 METHYL 4-(4-(BIS(2-CHLOROETHYL)AMINO)PHENYL)BUTYRATE 
• 4521-28-2 4-(4-Methoxyphenyl)butyric acid 
• 41826-92-0 Trepibutone 
• 4653-08-1 4-OXO-4-(2-THIENYL)BUTYRIC ACID 
• 3443-45-6 1-PYRENEBUTYRIC ACID 
• 2051-95-8 3-BENZOYLPROPIONIC ACID 
• 939-52-6 GAMMA-CHLOROBUTYROPHENONE 
• 638-32-4 SUCCINAMIC ACID 
• 6066-82-6 N-Hydroxysuccinimide 
• 96-48-0 gamma-Butyrolactone 

Recommend Products

• 69338-35-8  4-oxo-4-(1-pyrrolidinyl)butanoic acid 
• 123-75-1  pyrrolidine 
• 106-65-0  Dimethyl succinate 
• 186581-53-3  diazomethane 
• 60-29-7  diethyl ether 
• 4672-17-7  butane-4'-carboxy-(1'-piperidinyl)-carboxamide 
• 110-89-4  piperidine 
• 4653-08-1  4-oxo-4-thiophen-2-yl-butyric acid 
• 188290-36-0  thiophene 
• 63979-84-0  Succinyl Dicyanide 
• 110-86-1  pyridine 
• 74-90-8  hydrogen cyanide 
• 543-20-4  succinoyl dichloride 
• 22988-52-9  4-(5-methylthiophen-2-yl)-4-oxobutanoic acid 

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Quinoa starch granules were esterified with dodecenyl succinic anhydride (DDSA) to various degrees of substitution (DS) (0.0023 to 0.0095). Physicochemical properties and emulsification capacity of the modified starch were studied. Increasing DS increased the particle size, water solubility, and...detailed