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108-30-5

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108-30-5 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.]

Check Digit Verification of cas no

The CAS Registry Mumber 108-30-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 8 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 108-30:
(5*1)+(4*0)+(3*8)+(2*3)+(1*0)=35
35 % 10 = 5
So 108-30-5 is a valid CAS Registry Number.
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)

108-30-5 Well-known Company Product Price

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  • TCI America

  • (S0107)  Succinic Anhydride  >95.0%(T)

  • 108-30-5

  • 25g

  • 150.00CNY

  • Detail
  • TCI America

  • (S0107)  Succinic Anhydride  >95.0%(T)

  • 108-30-5

  • 500g

  • 290.00CNY

  • Detail
  • Alfa Aesar

  • (A12245)  Succinic anhydride, 99%   

  • 108-30-5

  • 250g

  • 207.0CNY

  • Detail
  • Alfa Aesar

  • (A12245)  Succinic anhydride, 99%   

  • 108-30-5

  • 500g

  • 372.0CNY

  • Detail
  • Alfa Aesar

  • (A12245)  Succinic anhydride, 99%   

  • 108-30-5

  • 1000g

  • 666.0CNY

  • Detail
  • Alfa Aesar

  • (A12245)  Succinic anhydride, 99%   

  • 108-30-5

  • 5000g

  • 2659.0CNY

  • Detail
  • Aldrich

  • (239690)  Succinicanhydride  ≥99% (GC)

  • 108-30-5

  • 239690-50G

  • 457.47CNY

  • Detail
  • Aldrich

  • (239690)  Succinicanhydride  ≥99% (GC)

  • 108-30-5

  • 239690-250G

  • 1,566.63CNY

  • Detail

108-30-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name succinic anhydride

1.2 Other means of identification

Product number -
Other names SAN

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:108-30-5 SDS

108-30-5Synthetic route

maleic anhydride
108-31-6

maleic anhydride

succinic acid anhydride
108-30-5

succinic acid anhydride

Conditions
ConditionsYield
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

succinic acid anhydride
108-30-5

succinic acid anhydride

Conditions
ConditionsYield
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

carbon monoxide

methyloxirane
75-56-9, 16033-71-9

methyloxirane

succinic acid anhydride
108-30-5

succinic acid anhydride

Conditions
ConditionsYield
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

maleic anhydride

WH2(η-cyclopentadienyl)2

WH2(η-cyclopentadienyl)2

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

(C5H5)2W(C4H2O3)

(C5H5)2W(C4H2O3)

Conditions
ConditionsYield
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

succinamic acid

ortho-bromophenylacetic acid
18698-97-0

ortho-bromophenylacetic acid

succinic acid anhydride
108-30-5

succinic acid anhydride

Conditions
ConditionsYield
With nitromethane; copper(l) chloride at 75℃; for 5h; Concentration; Temperature;91%
oxirane
75-21-8

oxirane

carbon monoxide
201230-82-2

carbon monoxide

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

β-Propiolactone
57-57-8

β-Propiolactone

Conditions
ConditionsYield
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

succinoyl dichloride

succinic acid anhydride
108-30-5

succinic acid anhydride

Conditions
ConditionsYield
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

L-proline

A

Succinimide
123-56-8

Succinimide

B

succinic acid anhydride
108-30-5

succinic acid anhydride

Conditions
ConditionsYield
With dihydrogen peroxide; sodium hydroxide In water for 50h; pH=10; Reflux;A 81%
B 19%
maleic anhydride
108-31-6

maleic anhydride

A

4-butanolide
96-48-0

4-butanolide

B

succinic acid anhydride
108-30-5

succinic acid anhydride

Conditions
ConditionsYield
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

tetrahydrofuran

A

4-butanolide
96-48-0

4-butanolide

B

5-hydroxydihydrofuran-2(3H)-one
50768-69-9

5-hydroxydihydrofuran-2(3H)-one

C

succinic acid anhydride
108-30-5

succinic acid anhydride

Conditions
ConditionsYield
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

oxirane

carbon monoxide
201230-82-2

carbon monoxide

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
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)

(1,2-bis(diphenylphosphino)ethane)Ni(C2H4CO2)

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

Ni(CO)2{1,2-bis(diphenylphosphino)ethane}
15793-01-8

Ni(CO)2{1,2-bis(diphenylphosphino)ethane}

Conditions
ConditionsYield
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

maleic anhydride

2-methoxyacetic acid
625-45-6

2-methoxyacetic acid

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

(methoxymethyl)succinic anhydride

(methoxymethyl)succinic anhydride

Conditions
ConditionsYield
With titanium(IV) oxide In acetonitrile for 18h; UV-irradiation; Inert atmosphere;A 16%
B 54%
n-butane
106-97-8

n-butane

succinic acid anhydride
108-30-5

succinic acid anhydride

Conditions
ConditionsYield
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

maleic anhydride

A

4-butanolide
96-48-0

4-butanolide

B

succinic acid anhydride
108-30-5

succinic acid anhydride

C

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
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

formaldehyd

Dimethyl succinate
106-65-0

Dimethyl succinate

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

methyl hydrogen succinate
3878-55-5

methyl hydrogen succinate

C

citraconic acid anhydride
616-02-4

citraconic acid anhydride

D

carbon dioxide
124-38-9

carbon dioxide

Conditions
ConditionsYield
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

1,3,5-Trioxan

methyl hydrogen succinate
3878-55-5

methyl hydrogen succinate

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

citraconic acid anhydride
616-02-4

citraconic acid anhydride

C

carbon dioxide
124-38-9

carbon dioxide

D

Dimethyl succinate
106-65-0

Dimethyl succinate

Conditions
ConditionsYield
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

1,3,5-Trioxan

Dimethyl succinate
106-65-0

Dimethyl succinate

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

methyl hydrogen succinate
3878-55-5

methyl hydrogen succinate

C

citraconic acid anhydride
616-02-4

citraconic acid anhydride

D

carbon dioxide
124-38-9

carbon dioxide

Conditions
ConditionsYield
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

maleic anhydride

Trimethylacetic acid
75-98-9

Trimethylacetic acid

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

2-tert-butylsuccinic anhydride
52685-36-6

2-tert-butylsuccinic anhydride

Conditions
ConditionsYield
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

2,3-bis(trimethylsilyl)-1,3-butadiene-1,4-dione

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

(Z)-2,3-bis(trimethylsilyl)succinic anhydride

(Z)-2,3-bis(trimethylsilyl)succinic anhydride

Conditions
ConditionsYield
With water In acetone at 22℃; for 0.5h;A n/a
B 15%
pyridine
110-86-1

pyridine

diethyl ether
60-29-7

diethyl ether

hydrogen cyanide
74-90-8

hydrogen cyanide

succinoyl dichloride
543-20-4

succinoyl dichloride

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

Succinyl Dicyanide
63979-84-0

Succinyl Dicyanide

maleic anhydride
108-31-6

maleic anhydride

ethyl acetate
141-78-6

ethyl acetate

succinic acid anhydride
108-30-5

succinic acid anhydride

Conditions
ConditionsYield
at 20℃; Hydrogenation;
tetrachloromethane
56-23-5

tetrachloromethane

peroxydicuccinic acid
123-23-9

peroxydicuccinic acid

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

Adipic acid
124-04-9

Adipic acid

chloroform
67-66-3

chloroform

1,2-diisopropylidene-cyclobutane
3642-16-8

1,2-diisopropylidene-cyclobutane

A

Tetramethyl-[1,2,4,5]tetroxan
1073-91-2

Tetramethyl-[1,2,4,5]tetroxan

B

succinic acid anhydride
108-30-5

succinic acid anhydride

C

acetone
67-64-1

acetone

Conditions
ConditionsYield
at -20℃; bei der Ozonisation;
(E)-1,2-dichloro-1-ethoxy-ethene
42345-82-4

(E)-1,2-dichloro-1-ethoxy-ethene

succinic acid
110-15-6

succinic acid

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

succinic acid
110-15-6

succinic acid

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

4-Ketopimelic acid
502-50-1

4-Ketopimelic acid

Conditions
ConditionsYield
5-6 h Erhitzen der Schmelze; anschliessend Eindampfen mit konz. HCl;
ethyl 3-(chloroformyl)propionate
14794-31-1

ethyl 3-(chloroformyl)propionate

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

chloroethane
75-00-3

chloroethane

Conditions
ConditionsYield
bei der Destillation unter vermindertem Druck;
L-menthylsuccinic acid
77341-67-4

L-menthylsuccinic acid

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

menthol
89-78-1

menthol

Conditions
ConditionsYield
at 300℃;
oxalic acid
144-62-7

oxalic acid

succinoyl dichloride
543-20-4

succinoyl dichloride

succinic acid anhydride
108-30-5

succinic acid anhydride

succinic acid
110-15-6

succinic acid

acetic anhydride
108-24-7

acetic anhydride

succinic acid anhydride
108-30-5

succinic acid anhydride

Conditions
ConditionsYield
beim Schuetteln der waessr. Loesung von bernsteinsaurem Natrium;
at 120 - 150℃; unter Druck;
pyrrolidine
123-75-1

pyrrolidine

succinic acid anhydride
108-30-5

succinic acid anhydride

4-oxo-4-(1-pyrrolidinyl)butanoic acid
69338-35-8

4-oxo-4-(1-pyrrolidinyl)butanoic acid

Conditions
ConditionsYield
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

succinic acid anhydride

methanol
67-56-1

methanol

methyl hydrogen succinate
3878-55-5

methyl hydrogen succinate

Conditions
ConditionsYield
at 20℃;100%
at 64 - 68℃; for 3.8h;98.5%
at 70℃; for 2h;98%
succinic acid anhydride
108-30-5

succinic acid anhydride

oleoyl alcohol
143-28-2

oleoyl alcohol

oleyl hemisuccinate
20060-41-7

oleyl hemisuccinate

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 14h; Inert atmosphere;100%
at 120℃;
In pyridine at 20℃;
succinic acid anhydride
108-30-5

succinic acid anhydride

1-Hexadecanol
36653-82-4

1-Hexadecanol

hexadecanol monosuccinate
50893-80-6

hexadecanol monosuccinate

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 14h; Inert atmosphere;100%
With dmap In toluene at 110℃; for 1.5h;79.4%
With pyridine42%
succinic acid anhydride
108-30-5

succinic acid anhydride

Cholestanol
80-97-7

Cholestanol

succinic acid mono-3β-cholestanyl ester
84597-57-9

succinic acid mono-3β-cholestanyl ester

Conditions
ConditionsYield
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

succinic acid anhydride

cyclohexylamine
108-91-8

cyclohexylamine

4-(cyclohexylamine)-4-oxobutanoic acid
21451-32-1

4-(cyclohexylamine)-4-oxobutanoic acid

Conditions
ConditionsYield
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

succinic acid anhydride

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

N-<2-(3,4-dimethoxyphenyl)ethyl>succinimide
39662-45-8

N-<2-(3,4-dimethoxyphenyl)ethyl>succinimide

Conditions
ConditionsYield
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

succinic acid anhydride

phenylhydrazine
100-63-0

phenylhydrazine

4-oxo-4-(2-phenylhydrazinyl)butanoic acid
14580-01-9

4-oxo-4-(2-phenylhydrazinyl)butanoic acid

Conditions
ConditionsYield
In acetonitrile at 20℃; for 24h;100%
With ethanol
succinic acid anhydride
108-30-5

succinic acid anhydride

erythromycin
114-07-8

erythromycin

2'-O-(3-carboxypropanoyl) erythromycin
20057-07-2

2'-O-(3-carboxypropanoyl) erythromycin

Conditions
ConditionsYield
In acetone at 50℃;100%
With acetone
With dichloromethane
succinic acid anhydride
108-30-5

succinic acid anhydride

tert-butylamine
75-64-9

tert-butylamine

4-(tert-butylamino)-4-oxobutanoic acid
6622-06-6

4-(tert-butylamino)-4-oxobutanoic acid

Conditions
ConditionsYield
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

succinic acid anhydride

allyl alcohol
107-18-6

allyl alcohol

4-(allyloxy)-4-oxobutanoic acid
3882-09-5

4-(allyloxy)-4-oxobutanoic acid

Conditions
ConditionsYield
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

succinic acid anhydride

2-(Trimethylsilyl)ethanol
2916-68-9

2-(Trimethylsilyl)ethanol

4-oxo-4-(2-(trimethylsilyl)ethoxy)butanoic acid
93790-78-4

4-oxo-4-(2-(trimethylsilyl)ethoxy)butanoic acid

Conditions
ConditionsYield
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 dichloromethane81%
succinic acid anhydride
108-30-5

succinic acid anhydride

4-amino-phenol
123-30-8

4-amino-phenol

4-(4'-hydroxy-phenylamino)-4-oxo-butanoic acid
62558-67-2

4-(4'-hydroxy-phenylamino)-4-oxo-butanoic acid

Conditions
ConditionsYield
With sodium dodecyl-sulfate In methanol; water at 20℃; for 0.583333h;100%
With sodium dodecyl-sulfate In water87%
In water at 50℃;86%

108-30-5Related news

Physicochemical properties of dodecenyl Succinic anhydride (cas 108-30-5) (DDSA) modified quinoa starch08/19/2019

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

108-30-5Relevant articles and documents

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Hoffman,Schlessinger

, p. 1245 (1971)

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Nickel promoted functionalization of CO2 to anhydrides and ketoacids

Greenburg, Zoe R.,Jin, Dong,Williard, Paul G.,Bernskoetter, Wesley H.

, p. 15990 - 15996 (2014)

The reductive functionalization of carbon dioxide into high value organics was accomplished via the coupling with carbon monoxide and ethylene/propylene at a zerovalent nickel species bearing the 2-((di-t-butylphosphino)methyl)pyridine ligand (PN). An initial oxidative coupling between carbon dioxide, olefin, and (PN)Ni(1,5-cyclooctadiene) afforded five-membered nickelacycle lactone species, which were produced with regioselective 1,2-coupling in the case of propylene. The propylene derived nickelacycle lactone was isolated and characterized by X-ray diffraction. Addition of carbon monoxide, or a combination of carbon monoxide and diethyl zinc to the nickelacycle lactone complexes afforded cyclic anhydrides and 1,4-ketoacids, respectively, in moderate to high yields. The primary organometallic product of the transformation was zerovalent (PN)Ni(CO)2. This journal is

Heterogeneous catalysts for the cyclization of dicarboxylic acids to cyclic anhydrides as monomers for bioplastic production

Rashed, Md. N.,Siddiki,Ali, Md. A.,Moromi, Sondomoyee K.,Touchy, Abeda S.,Kon, Kenichi,Toyao, Takashi,Shimizu, Ken-Ichi

, p. 3238 - 3242 (2017)

Cyclic anhydrides, key intermediates of carbon-neutral and biodegradable polyesters, are currently produced from biomass-derived dicarboxylic acids by a high-cost multistep process. We present a new high-yielding process for the direct intramolecular dehydration of dicarboxylic acids using a reusable heterogeneous Lewis acid catalyst, Nb2O5·nH2O. Various dicarboxylic acids, which can be produced by a biorefinery process, are transformed into the corresponding cyclic anhydrides as monomers for polyester production. This method is suitable for the production of renewable polyesters in a biorefinery process.

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Windholz,T.B.,Clements,J.B.

, p. 3021 - 3023 (1964)

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Clay catalysis: A convenient and rapid formation of anhydride from carboxylic acid and isopropenyl acetate under microwave irradiation

Villemin,Labiad,Loupy

, p. 419 - 424 (1993)

The Montmorillonite KSF catalyses the synthesis of anhydrides from carboxylic acids in the presence of isopropenyl acetate under microwave irradiations.

Mechanism of synthesis of maleic and succinic anhydrides by carbonylation of acetylene in solutions of palladium complexes

Bruk,Oshanina,Kozlova,Temkin,Odintsov

, p. 1071 - 1083 (1998)

The mechanism of synthesis of maleic and succinic anhydrides from acetylene and CO in the PdBr2 - LiBr - organic solvent catalytic system was studied using the procedure of advancement and discrimination of hypotheses. The hypotheses were obtained using the data bank on elementary steps and the Comb1 combinatorial program. The discrimination of the hypotheses was based on the data of NMR and IR spectroscopy, studies of isotope exchange, the role of potential organic intermediates, the kinetic isotope effect, and one-factor kinetic experiments. The most probable mechanism of synthesis of maleic anhydride includes insertion of acetylene and CO into the Pd - Pd bond of the Pd1 complex, which is formed from Pd11 at the initial step of the process. Succinic anhydride results from the intramolecular transformation of the hydride complex of palladium and maleic anhydride. The palladium hydride complexes detected in the contact solution apparently play the crucial role in the conjugation of oxidation, reduction, and addition type reactions.

Gas-phase hydrogenation of maleic anhydride to γ-butyrolactone at atmospheric pressure over Cu-CeO2-Al2O3 catalyst

Yu, Yang,Guo, Yanglong,Zhan, Wangcheng,Guo, Yun,Wang, Yanqin,Wang, Yunsong,Zhang, Zhigang,Lu, Guanzhong

, p. 77 - 81 (2011)

Cu-CeO2-Al2O3 catalyst, prepared by co-precipitation method, was investigated for the gas-phase hydrogenation of maleic anhydride (MA) to γ-butyrolactone (GBL) at atmospheric pressure and the catalyst deactivation was also studied. Effects of catalyst composition, reaction temperature, and liquid hourly space velocity (LHSV) of raw material on the catalytic performance of Cu-CeO2-Al2O3 catalyst were investigated. The catalyst (molar ratio of Cu:Ce:Al = 1:1:2) showed better catalytic performance, in which both the conversion of MA and the selectivity of GBL kept 100% within two hours under the reaction conditions of 6 mL catalyst, 0.1 MPa, 220-280 °C, 30 mL min-1 H2, 0.6 h-1 LHSV of 20 wt.% MA/GBL. As for Cu-CeO2-Al 2O3 catalyst, smaller crystallite size of Cu and higher Cu surface area are favorable to increase its catalytic performance. The deactivation of Cu-CeO2-Al2O3 catalyst is due to formation of the compact wax-like deposition on the catalyst surface, which is probably ascribed to the strong adsorption of succinic anhydride and then polymerization on the catalyst surface. The catalytic performance of the regenerated catalyst can be recovered completely by the regeneration method of N2-air-H2 stage treatment.

Ni/Al2O3 catalysts derived from spinel NiAl2O4 for low-temperature hydrogenation of maleic anhydride to succinic anhydride

Li, Jie,Ren, Yuanhang,Yue, Bin,He, Heyong

, p. 1166 - 1173 (2017)

Ni/Al2O3 catalysts were derived from spinel NiAl2O4 with different Ni content ((2.5, 5 and 7.5) wt%). The catalysts were obtained by H2 reduction and were investigated for the low-temperature hydrogenation of maleic anhydride (MA) to produce succinic anhydride (SA). The characterization results showed that Ni0 active sites were mainly derived during the H2 reduction from spinel NiAl2O4. Among the catalysts studied, employing the optimum preparation and reaction conditions with Ni(5%)/Al2O3 yielded the highest catalytic performance. A near-100% conversion of MA and ~90% selectivity to SA were achieved at 120 °C and 0.5 MPa of H2 with a weighted hourly space velocity (MA) of 2 h?1.

Active ruthenium catalysts prepared by Cacumen Platycladi leaf extract for selective hydrogenation of maleic anhydride

Huang, Yangqiang,Ma, Yao,Cheng, Youwei,Wang, Lijun,Li, Xi

, p. 124 - 130 (2015)

Ruthenium-based catalysts were prepared by a biogenic method via Cacumen Platycladi leaf extract and tested in the liquid phase hydrogenation of maleic anhydride to the corresponding succinic anhydride. The reaction conditions were optimized by varying the Ru loading, reaction temperature, hydrogen pressure, reaction time and organic solvents to achieve the superb catalytic performance. Reusability tests and comparison with commercial catalysts were also studied on the biosynthesized Ru-based catalysts. Furthermore, a variety of characterization techniques, such as TEM, HRTEM, EDS and XPS showed the effectively introduction of ruthenium nanoparticles into the carbon supports. The analyses of FTIR and TG confirmed that the plant extract served as both reducing and protecting agents.

Continuous-Flow Production of Succinic Anhydrides via Catalytic β-Lactone Carbonylation by Co(CO)4?Cr-MIL-101

Park, Hoyoung D.,Dinca, Mircea,Román-Leshkov, Yuriy

, p. 10669 - 10672 (2018)

Industrial synthesis of succinic acid relies on hydrocarbon oxidation or biomass fermentation routes that suffer from energy-costly separation processes. Here we demonstrate an alternate route to succinic anhydrides via β-lactone carbonylation by heterogeneous bimetallic ion-pair catalysis in Co(CO)4--incorporated Cr-MIL-101 (Co(CO)4Cr-MIL-101, Cr-MIL-101 = Cr3O(BDC)3F, H2BDC = 1,4-benzenedicarboxylic acid). Postsynthetically introduced Co(CO)4- facilitates CO insertion to β-lactone substrates activated by the Lewis acidic Cr(III) centers of the metal-organic framework (MOF), leading to catalytic carbonylation with activity and selectivity profiles that compare favorably to those reported for homogeneous ion-pair catalysts. Moreover, the heterogeneous nature of the MOF catalyst enables continuous production of succinic anhydride through a packed bed reactor, with room temperature β-propiolactone carbonylation activity of 1300 molAnhydride·molCo-1 over 6 h on stream. Simple evaporation of the fully converted product stream yields the desired anhydride as isolated solids, highlighting the unique processing advantages conferred by this first example of heterogeneous β-lactone carbonylation pathway.

A convenient method for synthesis of symmetrical acid anhydrides from carboxylic acids with trichloroacetonitrile and triphenylphosphine

Kim,Jang

, p. 395 - 399 (2001)

Various carboxylic acids are converted into the corresponding carboxylic acid anhydrides treated with trichloroacetonitrile and triphenylphosphine in the presence of triethylamine at room temperature.

Maleic anhydride hydrogenation to succinic anhydride over mesoporous Ni/TiO2 catalysts: Effects of Ni loading and temperature

Torres, Cecilia C.,Alderete, Joel B.,Mella, Claudio,Pawelec, Barbara

, p. 441 - 448 (2016)

Catalytic hydrogenation of maleic anhydride for the production of succinic anhydride can be a viable alternative to the higher energetic demand route based in the dehydration of succinic acid. In this sense, the metallic Ni catalysts supported on mesoporous TiO2 (anatase) substrate demonstrated to be very active and 100% selective in the liquid phase hydrogenation of maleic anhydride (MA) to succinic anhydride (SA). The catalysts, which were prepared via wet impregnation method with different Ni loading (5, 10 and 15?wt.%), were characterized by chemical analysis (ICP-AES), N2 physical adsorption-?desorption, H2-?temperature programmed reduction (H2-?TPR)?, X-ray diffraction (XRD)?, high resolution transmission electron spectroscopy (HR-TEM) and X-ray photoelectron spectroscopy (XPS). The Ni species interaction with support was investigated by TPR and by performing five catalyst recycling tests. After catalyst activation by reduction, the increase of Ni particle size with an increase of Ni loading was relatively small (from 6.9 to 8.9?nm) due to enhance of the metal-support interaction. After the first catalytic cycle, the optimized 5%Ni/TiO2 catalyst showed a small decrease in the Ni loading attributed to metal leaching during time course of reaction. Besides this, the 5%Ni/TiO2 catalyst exhibited a good stability during five continuous cycles with a very high yield of SA after 5 cycles. Finally, temperature experiments performed for the best system shown that the reaction temperature does not affect the SA selectivity in the temperature range studied (323?K–398?K).

NICKEL(0)-INDUZIERTE C-C-VERKNUEPFUNG ZWISCHEN KOHLENDIOXID UND ETHYLEN SOWIE MONO- ODER DI-SUBSTITUIERTEN ALKENEN

Hoberg, Heinz,Schaefer, Dietmar

, p. C51 - C53 (1983)

The nickel(0)-induced coupling of CO2 with ethylene or with mono- or di-substituted alkenes is described.The regioselectivity of this reaction has been determined.

New catalytic systems for oxidative carbonylation of acetylene to maleic anhydride

Bruk,Kozlova,Marshakha,Oshanina,Temkin,Kaliya

, p. 1875 - 1881 (1999)

A classification of polyfunctional catalytic systems based on discrimination of the main component (the catalyst participating in all stages of the formation of the product of catalytic reaction) and elucidating the functions of additional components of a catalytic system is suggested. The role of additional components in a number of new palladium-based catalytic systems used in the synthesis of maleic anhydride by oxidative carbonylation of acetylene was studied. It was established that the functions of Co and Fe phthalocyanine complexes (PcCo and Pc*Fe, respectively) in the mechanism of the process are different.

Selective liquid-phase hydrogenation of maleic anhydride to succinic anhydride on biosynthesized Ru-based catalysts

Ma, Yao,Huang, Yangqiang,Cheng, Youwei,Wang, Lijun,Li, Xi

, p. 40 - 44 (2014)

Ru-based catalysts, supported on activated carbon and carbon nanotubes, were synthesized by a simple and eco-friendly bioreduction method and tested in the liquid-phase hydrogenation of maleic anhydride. Over 2.0% Ru/AC, succinic anhydride was produced with a maximum yield of 99.2% without further hydrogenation to γ-butyrolactone. Well-defined spherical shapes with uniform small size of Ru nanoparticles and the residual plant biomass were responsible for the excellent catalytic activities and stabilities.

Quantitative Evaluation of the gem-Dimethyl Effect on the Succinic Acid Anhydride Equilibrium. Conformations of the Acids and Anhydrides by Empirical Force Field Calculations

Ivanov, Petko M.,Pojarlieff, Ivan G.

, p. 245 - 250 (1984)

In order to evaluate quantitatively the gem-dimethyl effect on the succinic acid anhydride equilibrium, the conformations of succinic acid and its 2-methyl-, racemic 2,3-dimethyl-, tetramethyl-, and racemic 2,3-di-t-butyl-derivatives have been calculated by means of Allinger's 1977 empirical force field.An extension of the field was developed to calculate the conformations of the respective anhydrides.The calculated preferred conformations compare well with existing experimental data.No low-energy hydrogen-bonded minima for the acids were obtained.Increased substitution in the acids caused conformational changes facilitating ring closure: smaller torsion angles of conformations with gauche carboxy groups, favourable bond length and angle deformations, and a reduced number of preferred conformations.In the anhydrides, substitution leads to a twist around the C(2)-C(3) bond of the ring.The ΔΔH values estimated for the diacid anhydride equilibria agree well with experimental data in water indicating that the main cause of the observed gem-dimethyl effect in the anhydrides is relief of intramolecular strain arising on substitution in the acids.

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Akimoto,Echigoya

, p. 278 (1973)

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Conversion of succinic acid over Ni and Co catalysts

Rojas, Mabel,Zarate, Ximena,Canales, Roberto I.,Dongil, Ana Belen,Pazo, Cesar,Saavedra-Torres, Mario,Escalona, Néstor

, p. 165 - 176 (2021)

Liquid-phase hydrogenation of succinic acid (SA) over supported Ni and Co catalysts was investigated at 200 °C and 6 MPa of H2. Reduced and passivated catalysts with the same surface metal density (2.5 atoms of metal per nm2 of support) were prepared by incipient wetness impregnation. The catalysts were characterized by X-ray diffraction (XRD), N2 adsorption, X-ray photoelectron spectroscopy (XPS), temperature-programmed reduction (TPR), CO-chemisorption, and temperature-programmed desorption of NH3 (TPD-NH3). The Ni and Co catalysts supported over SiO2 showed different product distribution, due to the adsorption of the SA over the surface of catalysts, determined by DFT calculations. The Co/SiO2, Co/SiO2-Al2O3, and Co/Al2O3 catalysts showed different product distribution, which was correlated with total acidity from TPD-NH3 results. In general, the Co catalysts promoted the hydrogenation process; however, the highest total acidity showed by Co/Al2O3 also promoted the dehydration process. Finally, the initial rate follows the trend according to the dispersion determined by CO-chemisorption.

Rhodium-catalysed, Carbon Dioxide-mediated Aerobic Oxidation of Ethers

Fazlur-Rahman, A. K.,Tsai, Jing-Cherng,Nicholas, Kenneth M.

, p. 1334 - 1335 (1992)

In the presence of carbon dioxide (NBD = 2,5-norbornadiene) 1 catalyses the aerobic oxidation of ethers to esters with coproduction of formic acid.

Synthesis of succinic anhydride from maleic anhydride on Ni/diatomite catalysts

Guo, Shaofei,Shi, Li

, p. 137 - 141 (2013)

The characteristics and catalytic properties of Ni(5 wt%)/diatomite, Ni(5 wt%)/γ-Al2O3, Ni(5% wt)/Bentonite clay and Ni(5 wt%)/attapulgite clay were investigated and compared in terms of catalytic activities for liquid-phase hydrogenation of maleic anhydride (MA). The results showed that the diatomite support exhibited the highest activity and selectivity. Using Ni(7 wt%)/diatomite catalyst, the 100% conversion of MA and 96.20% selectivity to SA were obtained for MA hydrogenation at 190 C. The X-ray diffraction (XRD) studies showed that there is only NiO on the support and no elemental nickel (Ni0) and Ni2O3 was detected in unreduced samples. XRD and H2 temperature-programmed reduction (TPR) studies also showed that NiO species were all converted to metallic nickel (Ni0) after reduction at 350 C.

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Froeschl,Maier

, p. 256,271, 272 (1932)

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Hydrogenation of maleic anhydride to succinic anhydride over nickel/clay catalysts

Guo, Shaofei,Tian, Weiping,Shi, Li

, p. 757 - 763 (2012)

Hydrogenation of maleic anhydride (MA) to succinic anhydride (SA) over Ni/clay catalysts prepared by an impregnation method has been studied at different temperatures, Ni contents, pressures and weighted hourly space velocity (WHSV). The catalytic activity was greatly influenced by the temperature, Ni content, WHSV and pressure. A 97.1 % MA conversion with 99.6 % selectivity to SA was obtained over 5 %wt catalyst at 180 °C and at a pressure of 1 MPa H2. The catalysts were characterized by an array of techniques, including X-ray diffraction (XRD), H2 temperature-programmed reduction (TPR) and thermogravimetric analysis (TGA). XRD and TPR studies showed that nickel was present as Ni2? species on the support. Increasing the calcination temperature up to 650 °C led to the destruction of the support structure, as observed by TGA, while a calcination temperature of 550 °C gave the best results. Catalyst deactivation studies showed that the catalyst has a long lifetime, the yield of SA remaining better than 90 % even after a reaction time of 60 h. Studies on the catalyst induction showed that the presence or absence of an induction period was determined by the type of hydrogenation catalyst. Springer Science+Business Media Dordrecht 2012.

Carbon Dioxide as Modulator of the Oxidative Properties of Dioxygen in the Presence of Transition Metal Systems

Aresta, Michele,Fragale, Carlo,Quaranta, Eugenio,Tommasi, Immacolata

, p. 315 - 317 (1992)

In the presence of transition metal ( Fe, Rh) catalysts, CO2 can modulate the oxidative properties of O2 towards tetrahydrofuran (THF) and styrene; the intermediate formation of metal-peroxocarbonate species, , seems to play a key role in these processes.

Photocatalytic valorization of furfural to value-added chemicals via mesoporous carbon nitride: a possibility through a metal-free pathway

Battula, Venugopala R.,Chauhan, Deepak K.,Giri, Arkaprabha,Kailasam, Kamalakannan,Patra, Abhijit

, p. 144 - 153 (2022/01/19)

Strategizing the exploitation of renewable solar light could undoubtedly provide new insight into the field of biomass valorization. Therefore, for the first time, we reported a heterogeneous photocatalytic oxidation route of renewable furfural (FUR) to produce industrial feedstocks maleic anhydride (MAN) and 5-hydroxy-2(5H)-furanone (HFO) under simulated solar light (AM 1.5G) using molecular oxygen (O2) as a terminal oxidant and mesoporous graphitic carbon nitride (SGCN) as a photocatalyst. SGCN showed an excellent photoconversion (>95%) of FUR with 42% and 33% selectivity to MAN and HFO, respectively. Moreover, an excellent selectivity towards MAN (66%) under natural sunlight indicates a pioneering route for the sustainable production of MAN. In addition, the underlying mechanistic route of the FUR photo-oxidation was investigated via various experiments including scavenger studies, substrate studies, and electron spin resonance (ESR) studies which constructively proved the pivotal role of singlet oxygen (1O2) and holes (h+) in FUR photo-oxidation.

Application of two-dimensional MoS2 catalyst in catalyzing selective hydrogenation of maleic anhydride to prepare succinic anhydride

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Paragraph 0033-0036; 0043-0060, (2021/06/21)

The invention relates to the field of catalysts, and particularly discloses application of a two-dimensional MoS2 catalyst in catalyzing selective hydrogenation of maleic anhydride to prepare succinic anhydride. A preparation method of the two-dimensional MoS2 catalyst comprises the following steps: mixing ammonium molybdate and thiourea in water, conducting reacting at 180-240 DEG C for 12-24 hours, collecting a product after the reaction is finished, conducting washing for multiple times, and conducting drying to obtain the two-dimensional MoS2 catalyst. The two-dimensional MoS2 catalyst provided by the invention has high conversion rate and high selectivity for preparing succinic anhydride by selective hydrogenation of maleic anhydride.

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