Conditions | Yield |
---|---|
With lithium hydroxide In tetrahydrofuran at 20℃; for 8h; Inert atmosphere; | 84% |
2-methylenesuccinic acid
A
poly(methacrylic acid)
B
citraconic acid
C
Mesaconic acid
Conditions | Yield |
---|---|
With 5% Pt/Al2O3; sodium hydroxide In water at 250℃; for 1h; Reagent/catalyst; Temperature; Inert atmosphere; | A 68% B n/a C n/a |
With sodium hydroxide In water at 180℃; under 112511 Torr; for 0.241667h; | A 27.26 %Spectr. B 36.48 %Spectr. C 16.23 %Spectr. |
With sodium hydroxide at 280℃; for 0.0583333h; | A 57.08 %Chromat. B 5.91 %Chromat. C 5.72 %Chromat. |
With sodium hydroxide at 250℃; for 0.25h; Reagent/catalyst; |
citric acid
A
poly(methacrylic acid)
B
citraconic acid
C
Mesaconic acid
D
2-methylenesuccinic acid
Conditions | Yield |
---|---|
With 4-methoxy-phenol; triphenylphosphine In water at 225℃; under 20686.5 Torr; for 1.5h; Temperature; Glovebox; Inert atmosphere; | A 24.1% B n/a C n/a D n/a |
With sodium hydroxide at 250℃; for 0.25h; Reagent/catalyst; |
LACTIC ACID
citraconic acid
Conditions | Yield |
---|---|
at 250 - 260℃; |
Conditions | Yield |
---|---|
With acetyl chloride | |
Irradiation.UV-Licht; | |
at 250℃; |
Conditions | Yield |
---|---|
at 250 - 260℃; |
Conditions | Yield |
---|---|
Citraconsaeureanhydrid entsteht bei der Destillation; | |
Multi-step reaction with 2 steps 1: water / 180 - 200 °C 2: 250 °C View Scheme | |
With sodium hydroxide In water at 190℃; under 112511 Torr; for 0.0666667h; Temperature; | 25.32 %Spectr. |
Conditions | Yield |
---|---|
With water Equilibrium constant; pH = 0.3; | |
With water Kinetik der Bildung; | |
With water |
Conditions | Yield |
---|---|
Citraconsaeureanhydrid entsteht bei der Destillation; |
Conditions | Yield |
---|---|
bei der Destillation; auch ihr Anhydrid entsteht; unter intermediaerer Bildung von Itaconsaeureanhydrid; | |
With hydrogen iodide | |
man destilliert und laesst auf das gebildete Citraconsaeureanhydrid Wasser in der Kaelte einwirken; | |
Thermolysis.und Behandlung des Anhydrids mit Wasser; |
Conditions | Yield |
---|---|
With hydrogen iodide |
Conditions | Yield |
---|---|
at 170 - 280℃; unter vermindertem Druck; | |
With water at 280 - 300℃; under 30 - 40 Torr; |
3-methyl-2,4-hexadienedioic acid
A
citraconic acid
B
2-methylbutanedioic acid
C
2-hydroxy-2-methylbutane-1,4-dioic acid
D
2-hydroxy-2-methylpropanedioic acid
Conditions | Yield |
---|---|
With sodium hydroxide; dihydrogen peroxide at 90℃; for 4h; Product distribution; var. conc. of H2O2 and NaOH, var. time; |
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate In chloroform; water Mechanism; pH 0.3; pH 10.0; |
Conditions | Yield |
---|---|
With lithium hydroxide In tetrahydrofuran at 20℃; for 8h; Inert atmosphere; | 84% |
2-methylenesuccinic acid
A
poly(methacrylic acid)
B
citraconic acid
C
Mesaconic acid
Conditions | Yield |
---|---|
With 5% Pt/Al2O3; sodium hydroxide In water at 250℃; for 1h; Reagent/catalyst; Temperature; Inert atmosphere; | A 68% B n/a C n/a |
With sodium hydroxide In water at 180℃; under 112511 Torr; for 0.241667h; | A 27.26 %Spectr. B 36.48 %Spectr. C 16.23 %Spectr. |
With sodium hydroxide at 280℃; for 0.0583333h; | A 57.08 %Chromat. B 5.91 %Chromat. C 5.72 %Chromat. |
With sodium hydroxide at 250℃; for 0.25h; Reagent/catalyst; |
citric acid
A
poly(methacrylic acid)
B
citraconic acid
C
Mesaconic acid
D
2-methylenesuccinic acid
Conditions | Yield |
---|---|
With 4-methoxy-phenol; triphenylphosphine In water at 225℃; under 20686.5 Torr; for 1.5h; Temperature; Glovebox; Inert atmosphere; | A 24.1% B n/a C n/a D n/a |
With sodium hydroxide at 250℃; for 0.25h; Reagent/catalyst; |
LACTIC ACID
citraconic acid
Conditions | Yield |
---|---|
at 250 - 260℃; |
Conditions | Yield |
---|---|
With acetyl chloride | |
Irradiation.UV-Licht; | |
at 250℃; |
Conditions | Yield |
---|---|
at 250 - 260℃; |
Conditions | Yield |
---|---|
Citraconsaeureanhydrid entsteht bei der Destillation; | |
Multi-step reaction with 2 steps 1: water / 180 - 200 °C 2: 250 °C View Scheme | |
With sodium hydroxide In water at 190℃; under 112511 Torr; for 0.0666667h; Temperature; | 25.32 %Spectr. |
Conditions | Yield |
---|---|
With water Equilibrium constant; pH = 0.3; | |
With water Kinetik der Bildung; | |
With water |
Conditions | Yield |
---|---|
Citraconsaeureanhydrid entsteht bei der Destillation; |
Conditions | Yield |
---|---|
bei der Destillation; auch ihr Anhydrid entsteht; unter intermediaerer Bildung von Itaconsaeureanhydrid; | |
With hydrogen iodide | |
man destilliert und laesst auf das gebildete Citraconsaeureanhydrid Wasser in der Kaelte einwirken; | |
Thermolysis.und Behandlung des Anhydrids mit Wasser; |
Conditions | Yield |
---|---|
With hydrogen iodide |
Conditions | Yield |
---|---|
at 170 - 280℃; unter vermindertem Druck; | |
With water at 280 - 300℃; under 30 - 40 Torr; |
3-methyl-2,4-hexadienedioic acid
A
citraconic acid
B
2-methylbutanedioic acid
C
2-hydroxy-2-methylbutane-1,4-dioic acid
D
2-hydroxy-2-methylpropanedioic acid
Conditions | Yield |
---|---|
With sodium hydroxide; dihydrogen peroxide at 90℃; for 4h; Product distribution; var. conc. of H2O2 and NaOH, var. time; |
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate In chloroform; water Mechanism; pH 0.3; pH 10.0; |
2-Methoxy-4-methylphenol
A
citraconic acid
B
2-methylbutanedioic acid
C
2-hydroxy-2-methylbutane-1,4-dioic acid
D
malonic acid
E
3-methyl-2,4-hexadienedioic acid
F
oxalic acid
Conditions | Yield |
---|---|
With sodium hydroxide; oxygen at 45℃; under 63755.1 Torr; for 1.5h; Product distribution; Mechanism; var. temp., time, O2 pressure, conc. and amount of NaOH, different amounts of creosol; |
2-methoxy-6-methyl-1,4-benzoquinone
A
citraconic acid
B
methoxy-maleic acid
C
2-methoxy-6-methylbenzene-1,4-diol
Conditions | Yield |
---|---|
With sodium hydroxide; sodium silicate; diethylenetriaminopentaacetic acid; dihydrogen peroxide In water at 25℃; for 1h; Mechanism; pH 9.0; |
4-hydroxy-2-methoxy-4-methyl-2,5-cyclohexadien-1-one
A
citraconic acid
B
2-methylbutanedioic acid
C
2-hydroxy-2-methylbutane-1,4-dioic acid
D
2-hydroxy-2-methylpropanedioic acid
Conditions | Yield |
---|---|
With sodium hydroxide; air at 90℃; for 2h; Product distribution; var. temp. and time, further reagent: 3percent H2O2; |
Conditions | Yield |
---|---|
With dihydrogen peroxide In water at 20℃; for 0.5h; Oxidation; |
Conditions | Yield |
---|---|
With sodium hydroxide; copper(II) ion; dihydrogen peroxide at 80℃; for 2h; Product distribution; Further Variations:; other metal ions; also without metal ion; Oxidation; decomposition; |
Conditions | Yield |
---|---|
With sodium hydroxide; dihydrogen peroxide; manganese(II) at 80℃; for 2h; Product distribution; Further Variations:; other metal ions; also without metal ion; Oxidation; decomposition; |
3,3'-dimethoxy-5,5'-dimethyl-[1,1'-biphenyl]-2,2'-diol
A
citraconic acid
B
2-methylbutanedioic acid
C
2-hydroxy-3-methoxy-5-methylbenzaldehyde
D
2-hydroxy-3-methoxy-5-methylbenzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide; dihydrogen peroxide; iron(III) at 80℃; for 2h; Product distribution; Further Variations:; other metal ions; also without metal ion; Oxidation; decomposition; |
(2,4'-dihydroxy-3,3'-dimethoxy-5-methyl)diphenylmethane
A
citraconic acid
B
malic acid
C
oxalic acid
D
maleic acid
Conditions | Yield |
---|---|
With sodium hydroxide; dihydrogen peroxide; iron(III) at 80℃; for 2h; Product distribution; Further Variations:; other metal ions; also without metal ion; Oxidation; decomposition; |
4-methyl-2,5-dioxo-2,5-dihydro-pyrrole-3-carboxylic acid ethyl ester
citraconic acid
5-oxo-1-phenyl-3-pyrrolidinecarboxylic acid
A
3-methyl-1-phenylpyrrole-2,5-dione
B
citraconic acid
C
2-methylenesuccinic acid
Conditions | Yield |
---|---|
at 260℃; |
Conditions | Yield |
---|---|
at 170 - 280℃; unter vermindertem Druck (auch nach Zusatz von anderen Salzen); |
Conditions | Yield |
---|---|
With boron trifluoride at 65℃; for 0.333333h; | 100% |
With Bronsted acidic, ionic liquid containing, heteropolyanion functionalized polysiloxane network POS-HPA-IL for 5h; Reflux; Green chemistry; | 90% |
With hydrogenchloride |
citraconic acid
2-methylbutanedioic acid
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In tetrahydrofuran; ethanol at 20℃; for 24h; atmospheric pressure; | 99% |
With hydrogen; palladium on activated charcoal In tetrahydrofuran; ethanol at 20℃; for 24h; atmospheric pressure; | 99% |
With 10% Pd/C; hydrogen In tetrahydrofuran; ethanol at 20℃; under 760.051 Torr; for 24h; | 99% |
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% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; lithium fluoride; Diethyl carbonate at 60℃; for 6h; | 99% |
citraconic acid
bis(tri-n-butyltin)oxide
citraconic acid tributyltin monoester
Conditions | Yield |
---|---|
In benzene byproducts: H2O, dicarboxylate; mole ratio of (C4H9)3SnOSn(C4H9)3 and carboxylic acid 1:2; at 20°C or at reflux temp. to remove of water formed by azeotropic distn.; | 95% |
In benzene byproducts: H2O, dicarboxylate; mole ratio of (C4H9)3SnOSn(C4H9)3 and carboxylic acid 1:2; at 20°C or at reflux temp. to remove of water formed by azeotropic distn.; | 95% |
Conditions | Yield |
---|---|
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 60℃; under 0.3 - 3 Torr; for 50h; | 89% |
Conditions | Yield |
---|---|
With sulfuric acid for 3h; Reflux; | 88% |
With hydrogenchloride | |
With sulfuric acid; benzene | |
With phosphorus pentoxide 1.) 0-5 deg C, 2.) reflux, 3 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With sulfuric acid for 3h; Reflux; | 81% |
citraconic acid
cobalt(II) diacetate tetrahydrate
1,4-bis-(1H-imidazol-1-yl)benzene
Conditions | Yield |
---|---|
With sodium hydroxide In water at 120℃; for 96h; Autoclave; | 79% |
citraconic acid
{1,2-diaminocyclohexanepalladium(II)(citraconate)
Conditions | Yield |
---|---|
In water stirring for 2 h;; filtered; evapd.; elem. anal.;; | 77% |
citraconic acid
Conditions | Yield |
---|---|
In acetonitrile at 20 - 60℃; for 0.0833333h; | 77% |
palladium(II) acetate trimer
citraconic acid
Conditions | Yield |
---|---|
In acetone at 20℃; for 6h; | 75% |
Conditions | Yield |
---|---|
In water at 180℃; | 72% |
citraconic acid
Conditions | Yield |
---|---|
With acetic acid; hydroquinone for 3h; Diels-Alder Cycloaddition; Reflux; diastereoselective reaction; | 72% |
citraconic acid
Conditions | Yield |
---|---|
With acetic acid; hydroquinone for 3h; Diels-Alder Cycloaddition; Reflux; diastereoselective reaction; | 72% |
Conditions | Yield |
---|---|
71% |
Product Name: Citraconic acid (CAS NO.498-23-7)
Molecular Formula: C5H6O4
Molecular Weight: 130.1g/mol
Mol File: 498-23-7.mol
Einecs: 207-858-7
Appearance: White to light beige crystalline powder
Melting Point: 88-94 °C(lit.)
Boiling point: 336.6 °C at 760 mmHg
Flash Point: 171.5 °C
Density: 1.387 g/cm3
Water Solubility: Freely soluble
Sensitive: Hygroscopic
Surface Tension: 57.4 dyne/cm
Enthalpy of Vaporization: 63.72 kJ/mol
Vapour Pressure: 2.09E-05 mmHg at 25°C
XLogP3-AA: -0.1
H-Bond Donor: 2
H-Bond Acceptor: 4
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | oral | 1350mg/kg (1350mg/kg) | GASTROINTESTINAL: GASTRITIS | Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964. |
mouse | LD50 | oral | 2260mg/kg (2260mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: OTHER CHANGES | Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964. |
rat | LD50 | oral | 1320mg/kg (1320mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH | Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964. |
Safety Information of Citraconic acid (CAS NO.498-23-7):
Hazard Codes: Xn
Risk Statements: 22-36/37/38
22: Harmful if swallowed
36: Irritating to the eyes
37: Irritating to the respiratory system
38: Irritating to the skin
Safety Statements: 36-37/39-26
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37: Wear suitable gloves
39: Wear eye/face protection
Citraconic acid ,its CAS NO. is 498-23-7,the synonyms is (z)-2-Methyl-2-butenedioic acid ; (2z)-2-Methyl-2-butenedioic acid ; Kyselina citrakonova ; Kyselinacitrakonova ; Maleic acid, methyl- ; Methyl-maleicaci ; 2-Methyl-2-butenedioic acid ; Methylmaleic acid .
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