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| CAS No.: | 616-02-4 |
|---|---|
| Name: | Citraconic anhydride |
| Article Data: | 60 |
| Molecular Structure: | |
|
|
|
| Formula: | C5H4O3 |
| Molecular Weight: | 112.085 |
| Synonyms: | Citraconicanhydride (6CI,8CI);2-Methyl-2-butenedioic anhydride;2-Methylmaleicanhydride;3-Methyl-2,5-furandione;3-Methylmaleic anhydride;Citraconic acidanhydride;Methylmaleic anhydride;Monomethylmaleic anhydride;NSC 6182;a-Methylmaleic anhydride; |
| EINECS: | 210-459-0 |
| Density: | 1.334 g/cm3 |
| Melting Point: | 6-10 °C(lit.) |
| Boiling Point: | 211.467 °C at 760 mmHg |
| Flash Point: | 96.766 °C |
| Solubility: | Decomposes in water |
| Appearance: | clear colorless to very slightly yellow liquid |
| Hazard Symbols: |
 T
|
| Risk Codes: | 24-34-42/43 |
| Safety: | 26-28A-36/37/39-45 |
| Transport Information: | UN 2810 |
| PSA: | 43.37000 |
| LogP: | 0.01610 |
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| Conditions | Yield |
|---|---|
| With calcium In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; under 750.075 Torr; for 1.5h; Reagent/catalyst; | 99.3% |
| Stage #1: 2-methylenesuccinic acid With acetic anhydride at 80℃; Stage #2: at 230℃; under 262.526 Torr; for 4h; | 94% |
| 4Cs(1+)*SiW12O40(4-) = Cs4{SiW12O40} at 170 - 200℃; under 50 - 100 Torr; for 5.5h; Product distribution / selectivity; | 92.5% |
| Conditions | Yield |
|---|---|
| With trifluoroacetic anhydride at 20℃; Inert atmosphere; | 99% |
| With niobium(V) oxide hydrate In o-xylene at 160℃; for 72h; Inert atmosphere; Molecular sieve; | 94% |
| With phosphorus pentoxide In chloroform for 48h; Reflux; | 80% |
- 110-88-3
1,3,5-Trioxan
- 108-30-5
succinic acid anhydride
A
- 3878-55-5
methyl hydrogen succinate
B
- 616-02-4
citraconic acid anhydride
C
- 124-38-9
carbon dioxide
| Conditions | Yield |
|---|---|
| With gamma-alumina at 380℃; under 3750.38 Torr; Stobbe Condensation; Autoclave; Flow reactor; | A 7% B 43% C 16% |
- 50-00-0
formaldehyd
- 106-65-0
Dimethyl succinate
A
- 108-30-5
succinic acid anhydride
B
- 3878-55-5
methyl hydrogen succinate
C
- 616-02-4
citraconic acid anhydride
D
- 124-38-9
carbon dioxide
| 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% |
- 110-88-3
1,3,5-Trioxan
- 3878-55-5
methyl hydrogen succinate
A
- 108-30-5
succinic acid anhydride
B
- 616-02-4
citraconic acid anhydride
C
- 124-38-9
carbon dioxide
D
- 106-65-0
Dimethyl succinate
| Conditions | Yield |
|---|---|
| With gamma-alumina at 380℃; under 3750.38 Torr; Stobbe Condensation; Autoclave; Flow reactor; | A 9% B 23% C 15% D 30% |
- 110-88-3
1,3,5-Trioxan
- 106-65-0
Dimethyl succinate
A
- 108-30-5
succinic acid anhydride
B
- 3878-55-5
methyl hydrogen succinate
C
- 616-02-4
citraconic acid anhydride
D
- 124-38-9
carbon dioxide
| 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% |
- 80818-24-2
(Z)-(2-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid
A
- 616-02-4
citraconic acid anhydride
B
- 80818-11-7
(Z)-(3-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid
C
- 100-01-6
4-nitro-aniline
| Conditions | Yield |
|---|---|
| In tetrahydrofuran for 24h; Reflux; | A 9% B n/a C 22% |
| Conditions | Yield |
|---|---|
| bei der Destillation; |
- 14556-16-2
2,6-dioxo-3,6-dihydro-2H-pyran-4-carboxylic acid
- 616-02-4
citraconic acid anhydride
| Conditions | Yield |
|---|---|
| beim Destillieren; |
| Conditions | Yield |
|---|---|
| at 210℃; |
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Chemistry
IUPAC Name: 3-Methylfuran-2,5-dione(616-02-4)
Synonyms: 2,5-Furanedione, 3-methyl ; 3-Methyl-2,5-furandione ; 3-Methyl-5-furandione ; 3-methyl-furan-2,5-dione ; 3-Methylmaleic anhydride ; 3-Methylmaleicanhydride ; Alpha-Methylmaleic anhydride ; Alpha-methylmaleicanhydride
CAS: 616-02-4
MF: C5H4O3
MW: 112.08
MS: .gif)
EINECS: 210-459-0
Product Categories: Rubber & Plastic Auxiliary Agent ; Anhydride Monomers ; Monomers ; Polymer Science ; Carbonyl Compounds ; Carboxylic Acid Anhydrides ; Organic Building Blocks
Mol File: 616-02-4.mol
MP:6-10 °C(lit.)
Surface Tension: 42.9 dyne/cm
Density: 1.333 g/cm3
Flash Point: 96.8 °C
Enthalpy of Vaporization: 44.78 kJ/mol
Boiling Point: 211.5 °C at 760 mmHg
Vapour Pressure: 0.182 mmHg at 25°C
Refractive index n20/D 1.471(lit.)
storage temp: Store at RT.
Water Solubility: decomposes
Sensitive: Moisture Sensitive
BRN : 1835
Uses
Citraconic anhydride (616-02-4) used as raw materials in the production of organic synthesis (preparation clothing Ping acid, clothing Ping acid amide).
Production
Citraconic anhydride (616-02-4) is also known as butyrolactone - β - carboxylic acid, tetrahydrofuran oxo-3-carboxylic acid. Gain Citraconic anhydride (Citraconic anhydride) by the way of distillation .React with alkali to get itamalic acid,and then with hydrobromic acid to produce methyl bromide succinic acid,which heated with Ammonia of methanol ,producing HOOCCH(CH2OH) CH2CONH2 ,then treat with Silver oxide Ag2O for the product of succinic acid methyl bromide .
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| guinea pig | LD50 | skin | 1mL/kg (1mL/kg) | Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 269, 1944. | |
| rabbit | LD50 | skin | 218mg/kg (218mg/kg) | Shell Chemical Company. | |
| rat | LD50 | oral | 2600mg/kg (2600mg/kg) | Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 269, 1944. |
Safety Profile
Hazard Codes: T .gif){kind=small}
Risk Statements: 23/24/25-36/37/38-42/43-34
23/24/25: Toxic by inhalation, in contact with skin and if swallowed
36/37/38: Citraconic anhydride (616-02-4) is irritating to eyes, respiratory system and skin
42/43: May cause sensitization by inhalation and skin contact
34: Causes burns
Safety Statements: 26-36/37/39-45-28
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
28: After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
RIDADR: UN 2810 6.1/PG 3
WGK Germany: 3
RTECS: GE6825000
F: 10-21
HazardClass: 6.1
PackingGroup: III
HS Code: 29171990
Specification
Citraconic anhydride (616-02-4) is crystallization.