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498-24-8 Usage

Uses

Different sources of media describe the Uses of 498-24-8 differently. You can refer to the following data:
1. Mesaconic acid is used in electropolishing stainless steel and as a laminant for polyethylene.
2. Mesaconic Acid activates dopamine β-mono-oxygenase.

Definition

ChEBI: A dicarboxylic acid consisting of fumaric acid having a methyl substituent at the 2-position.

Purification Methods

Crystallise it from H2O or EtOH [Katakis et al. J Chem Soc, Dalton Trans 1491 1986]. [Beilstein 2 IV 2231.]

Check Digit Verification of cas no

The CAS Registry Mumber 498-24-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 8 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 498-24:
(5*4)+(4*9)+(3*8)+(2*2)+(1*4)=88
88 % 10 = 8
So 498-24-8 is a valid CAS Registry Number.
InChI:InChI=1/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+

498-24-8 Well-known Company Product Price

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  • Aldrich

  • (131040)  Mesaconicacid  99%

  • 498-24-8

  • 131040-10G

  • 742.95CNY

  • Detail
  • Aldrich

  • (131040)  Mesaconicacid  99%

  • 498-24-8

  • 131040-50G

  • 3,540.42CNY

  • Detail

498-24-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name mesaconic acid

1.2 Other means of identification

Product number -
Other names 2-Butenedioic acid, 2-methyl-, (E)-

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:498-24-8 SDS

498-24-8Synthetic route

diethylitaconate
2409-52-1

diethylitaconate

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
Stage #1: diethylitaconate With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating;
Stage #2: With hydrogenchloride for 3h; Heating;
80%
2-methylenesuccinic acid
97-65-4

2-methylenesuccinic acid

A

poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

B

citraconic acid
498-23-7

citraconic acid

C

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
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
77-92-9

citric acid

A

poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

B

citraconic acid
498-23-7

citraconic acid

C

Mesaconic acid
498-24-8

Mesaconic acid

D

2-methylenesuccinic acid
97-65-4

2-methylenesuccinic acid

Conditions
ConditionsYield
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;
3-bromo-4-methyl-2,5-furandione
59107-74-3

3-bromo-4-methyl-2,5-furandione

A

Mesaconic acid
498-24-8

Mesaconic acid

B

2-methylbutanedioic acid
498-21-5, 636-60-2

2-methylbutanedioic acid

Conditions
ConditionsYield
With water; zinc
ethanol
64-17-5

ethanol

citraconic acid
498-23-7

citraconic acid

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
Rate constant;
2-methyl-fumaramide
41138-18-5

2-methyl-fumaramide

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
With hydrogenchloride
citraconic acid
498-23-7

citraconic acid

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
beim Kochem die entstehende Itaconsaeure;
citraconic acid
498-23-7

citraconic acid

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
at 180 - 200℃;
Quantum yield; Irradiation;
With diethyl ether; chloroform; bromine an der Sonne;
citraconic acid
498-23-7

citraconic acid

A

Mesaconic acid
498-24-8

Mesaconic acid

B

2-methylenesuccinic acid
97-65-4

2-methylenesuccinic acid

Conditions
ConditionsYield
With sodium hydroxide
citraconic acid
498-23-7

citraconic acid

A

Mesaconic acid
498-24-8

Mesaconic acid

B

acrylic acid
79-10-7

acrylic acid

C

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
bei der Elektrolyse von citraconsaeurem Kalium.Electrolysis;
2-methylbutanedioic acid
498-21-5, 636-60-2

2-methylbutanedioic acid

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
nach Verfuetterung im Hundeorganismus;
diethyl citraconate
691-83-8

diethyl citraconate

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
With potassium hydroxide
(RS,SR)-2,3-dibromo-2-methyl-succinic acid
5469-23-8, 19371-95-0, 20515-34-8, 20515-35-9, 37951-41-0

(RS,SR)-2,3-dibromo-2-methyl-succinic acid

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
With potassium iodide und (Kupfer);
2-methylenesuccinic acid
97-65-4

2-methylenesuccinic acid

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

Mesaconic acid
498-24-8

Mesaconic acid

2-methylenesuccinic acid
97-65-4

2-methylenesuccinic acid

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
With water at 180 - 200℃;
With sodium hydroxide
Multi-step reaction with 2 steps
1: sodium hydroxide / 0.06 h / 280 °C
2: sodium hydroxide / 0.02 h / 270 °C
View Scheme
bromomethyl-succinic acid
20469-57-2

bromomethyl-succinic acid

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
With potassium hydroxide
citraconic acid anhydride
616-02-4

citraconic acid anhydride

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
With water; nitric acid beim Eindampfen bis zum Beginn der Entwicklung roter Daempfe;
With nitric acid durch Eindampfen bis zum Beginn der Entwicklung roter Daempfe;
Multi-step reaction with 2 steps
1: H2SO4
2: alcoholic KOH-solution
View Scheme
Multi-step reaction with 2 steps
1: bromine / 150 °C / beim Erhitzen im geschlossenen Rohr
2: zinc; water
View Scheme
o-toluenesulfonic acid
88-20-0

o-toluenesulfonic acid

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
With water; platinum Electrolysis.bei der Elektrolytischen Oxydation an Platin-Anoden;
With water; lead dioxide Electrolysis.bei der Elektrolytischen Oxydation an Blei(IV)-oxyd-Anoden;
2-Methyl-1,4-benzoquinone
553-97-9

2-Methyl-1,4-benzoquinone

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
With sulfuric acid at 10 - 12℃; bei der elektrolytischen Oxydation an einer PbO2-Anode;
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
at 70 - 75℃;
α-methyl-DL-aspartic acid
2792-66-7

α-methyl-DL-aspartic acid

1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

dimethyl sulfate
77-78-1

dimethyl sulfate

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
(+-)-2-amino-2-methyl-succinic acid;
citric acid
77-92-9

citric acid

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
Kochen des Destillationsprodukts (welches Citraconsaeure und Itaconsaeure bezw. deren Anhydride enthaelt) mit 10prozentiger Natronlauge;
3-methyl-1-phenylpyrrole-2,5-dione
3120-04-5

3-methyl-1-phenylpyrrole-2,5-dione

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
With hydrogenchloride
(2S,3S)-3-methylaspartic acid
6061-13-8

(2S,3S)-3-methylaspartic acid

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
With L-threo-3-methylaspartate ammonia-lyase In various solvent(s) Mechanism; enzymic ammonia elimination, different pH, labeled comp.;
In water at 20℃; Michaelis and catalytic center activity constants for deamination reaction by 3-methylaspartase from Morganella morganii strain YG-0601; pH 9.7; effect of various organic or inorganic compounds;
In water at 20℃; Michaelis and catalytic center activity constants for deamination reaction by 3-methylaspartase from Citrobacter sp. strain YG-0504; pH 9.7; effects of various organic or inorganic compounds;
With 3-methylaspartase; magnesium chloride In water Mechanism; Kinetics; various pL; also in D2O; primary deuterium and solvent isotope effects;
With 3-methylaspartase; potassium chloride; 2-amino-2-hydroxymethyl-1,3-propanediol; magnesium chloride In water at 30℃; Mechanism; Kinetics; various pL; also in D2O; isotope effects;
erythro-β-methyl-L-aspartate
7298-96-6

erythro-β-methyl-L-aspartate

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
With L-threo-3-methylapartase; magnesium(II); potassium ion In water at 30℃; for 24h; Rate constant; Product distribution; Mechanism; pH 9.0; Km, deuterium isotope effects;
With 3-methylaspartase deamination reaction, different enzyme concentrations, kinetic parameters: KM, Vmax;
2-methoxy-1,4-benzoquinone
2880-58-2

2-methoxy-1,4-benzoquinone

A

Mesaconic acid
498-24-8

Mesaconic acid

B

malonic acid
141-82-2

malonic acid

C

succinic acid
110-15-6

succinic acid

D

oxalic acid
144-62-7

oxalic acid

Conditions
ConditionsYield
With sodium hydroxide; oxygen at 90℃; under 7500.6 Torr; for 3h; Product distribution;
(2S,3S)-<3-2H>-3-methylaspartic acid
112365-92-1

(2S,3S)-<3-2H>-3-methylaspartic acid

Mesaconic acid
498-24-8

Mesaconic acid

Conditions
ConditionsYield
With 3-methylaspartase deamination reaction, different enzyme concentrations, kinetic parameters: KM, Vmax;
With 3-methylaspartase; magnesium chloride In water Mechanism; Kinetics; various pL; also in D2O; primary deuterium and solvent isotope effects;
With 3-methylaspartase; potassium chloride; 2-amino-2-hydroxymethyl-1,3-propanediol; magnesium chloride In water at 30℃; Mechanism; Kinetics; various pL; also in D2O; isotope effects;
citric acid
77-92-9

citric acid

A

diethyl 3-hydroxypentanedioate
638-18-6

diethyl 3-hydroxypentanedioate

B

Mesaconic acid
498-24-8

Mesaconic acid

C

1 propene 1,2,3 tricarboxylic acid
499-12-7

1 propene 1,2,3 tricarboxylic acid

D

2-methylenesuccinic acid
97-65-4

2-methylenesuccinic acid

E

citraconic acid anhydride
616-02-4

citraconic acid anhydride

F

itaconic acid anhydride
2170-03-8

itaconic acid anhydride

Conditions
ConditionsYield
With Sn/Pb solder at 150 - 210℃;
3-bromo-4-methyl-2,5-furandione
59107-74-3

3-bromo-4-methyl-2,5-furandione

water
7732-18-5

water

zinc turnings

zinc turnings

A

Mesaconic acid
498-24-8

Mesaconic acid

B

2-methylbutanedioic acid
498-21-5, 636-60-2

2-methylbutanedioic acid

Mesaconic acid
498-24-8

Mesaconic acid

2-methylbutanedioic acid
498-21-5, 636-60-2

2-methylbutanedioic acid

Conditions
ConditionsYield
With formic acid; (bppm)Rh(1,1,1,5,5,5,-hexafluoroacetylacetonate); triethylamine In dimethylsulfoxide-d6 at 30℃; for 8h;100%
With samarium diiodide In tetrahydrofuran for 0.0833333h; Ambient temperature;88%
With phenylsilane; C12H23N2O2P In tetrahydrofuran at 23℃; for 2h;86%
Mesaconic acid
498-24-8

Mesaconic acid

L-malic acid
2174-58-5

L-malic acid

Conditions
ConditionsYield
With formic acid; TETRACYCLINE; paraquat dichloride In water at 45℃; for 30h; Clostridium formicoaceticum;99%
ethanol
64-17-5

ethanol

Mesaconic acid
498-24-8

Mesaconic acid

(E)-2-methyl-but-2-enedioic acid diethyl ester
2418-31-7

(E)-2-methyl-but-2-enedioic acid diethyl ester

Conditions
ConditionsYield
With sulfuric acid for 3h; Reflux;90%
With sulfuric acid for 16h; Heating;81%
With sulfuric acid at 20℃; Reflux;68%
With hydrogenchloride
With sulfuric acid; benzene
Mesaconic acid
498-24-8

Mesaconic acid

(2S,3S)-3-methylaspartic acid
6061-13-8

(2S,3S)-3-methylaspartic acid

Conditions
ConditionsYield
With β-methyl aspartase; potassium chloride; ammonium chloride; magnesium chloride In water at 32℃; pH=9;90%
With ammonium hydroxide; 3-methylaspartate ammonia-lyase; sodium chloride; magnesium chloride at 30℃; for 50h;69%
With β-methylaspartase; ammonium chloride; ammonia; sodium chloride; magnesium chloride In water at 30℃; for 18h;66%
methanol
67-56-1

methanol

Mesaconic acid
498-24-8

Mesaconic acid

mesaconic acid dimethyl ester
617-53-8

mesaconic acid dimethyl ester

Conditions
ConditionsYield
With sulfuric acid for 5h; Reflux; Inert atmosphere;87%
With thionyl chloride at 0℃; for 2h; Reflux;76%
With sulfuric acid for 12h; Heating;75%
Mesaconic acid
498-24-8

Mesaconic acid

(2S,3RS)-3-methylaspartic acid
31571-69-4

(2S,3RS)-3-methylaspartic acid

Conditions
ConditionsYield
In water at 30℃; 0.2 M NH4Cl, 0.02 M MgCl2, 0.01 M KCl, methylaspartase, pH 9.0, several days;86%
Mesaconic acid
498-24-8

Mesaconic acid

C5H8(2)HNO4

C5H8(2)HNO4

Conditions
ConditionsYield
at 30℃; D2O, 0.2 M NH4Cl, 0.02 M MgCl2, 0.01 M KCl, methylaspartase, pD 8.6, several days;86%
Mesaconic acid
498-24-8

Mesaconic acid

chloroamine-T
127-65-1

chloroamine-T

C12H15NO7S

C12H15NO7S

Conditions
ConditionsYield
81%
methanol
67-56-1

methanol

Mesaconic acid
498-24-8

Mesaconic acid

citraconic acid dimethyl ester
84569-14-2

citraconic acid dimethyl ester

Conditions
ConditionsYield
With sulfuric acid Heating;80%
Mesaconic acid
498-24-8

Mesaconic acid

butan-1-ol
71-36-3

butan-1-ol

(E)-2-methylbut-2-enedicarboxylic acid dibutyl ester
22644-91-3

(E)-2-methylbut-2-enedicarboxylic acid dibutyl ester

Conditions
ConditionsYield
With sulfuric acid for 3h; Reflux;75%
Mesaconic acid
498-24-8

Mesaconic acid

C72H122N16O22

C72H122N16O22

C149H246N32O46

C149H246N32O46

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 2.5h;70%
zinc(II) nitrate hexahydrate

zinc(II) nitrate hexahydrate

Mesaconic acid
498-24-8

Mesaconic acid

water
7732-18-5

water

4-[2-(1-naphtalenyl)ethenyl]-pyridine
16375-56-7

4-[2-(1-naphtalenyl)ethenyl]-pyridine

2C17H13N*H2O*Zn(2+)*C5H4O4(2-)

2C17H13N*H2O*Zn(2+)*C5H4O4(2-)

Conditions
ConditionsYield
With triethylamine In methanol; ethanol70%
Mesaconic acid
498-24-8

Mesaconic acid

(S)-citramalic acid
6236-09-5

(S)-citramalic acid

Conditions
ConditionsYield
With formaldehyd; TETRACYCLINE; paraquat dichloride In water at 37℃; for 24h; Clostridium formicoaceticum, phosphate buffer;69.8%
mit Hilfe eines Mesaconase-Praeparats;
p-phenylpyridine
939-23-1

p-phenylpyridine

cadmium(II) nitrate tetrhydrate

cadmium(II) nitrate tetrhydrate

Mesaconic acid
498-24-8

Mesaconic acid

bis{(mesaconato)bis(4-phenylpyridyl)cadmium(II)}

bis{(mesaconato)bis(4-phenylpyridyl)cadmium(II)}

Conditions
ConditionsYield
With triethylamine In methanol; ethanol; water for 168h;65%
Mesaconic acid
498-24-8

Mesaconic acid

erythro-β-methyl-L-aspartate
7298-96-6

erythro-β-methyl-L-aspartate

Conditions
ConditionsYield
With 3-methylaspartase enzymic amination in protium oxide;61%
Multi-step reaction with 4 steps
1: 86 percent / H2O / 30 °C / 0.2 M NH4Cl, 0.02 M MgCl2, 0.01 M KCl, methylaspartase, pH 9.0, several days
2: 99 percent / aq. K2CO3
3: diethyl ether
4: 55 percent / HCl, AcOH / Heating
View Scheme
Mesaconic acid
498-24-8

Mesaconic acid

(2S,3S)-2-Hydrazino-3-methylsuccinic acid

(2S,3S)-2-Hydrazino-3-methylsuccinic acid

Conditions
ConditionsYield
With potassium chloride; hydrazine hydrate; magnesium chloride at 30℃; for 72h; 3-methylaspartase (EC 4.3.1.2);61%
With potassium and magnesium ions; hydrazine In water for 72h; 3-methylaspartase;41%
Mesaconic acid
498-24-8

Mesaconic acid

(2S,3S)-<3-2H>-3-methylaspartic acid
112365-92-1

(2S,3S)-<3-2H>-3-methylaspartic acid

Conditions
ConditionsYield
With ammonium hydroxide; potassium chloride; water-d2; magnesium chloride In water at 30℃; for 48h; with 3-methylaspartase;60%
With 3-methylaspartase; water-d2 enzymic amination;60%
aluminum(III) nitrate nonahydrate

aluminum(III) nitrate nonahydrate

Mesaconic acid
498-24-8

Mesaconic acid

C5H4O4(2-)*Al(3+)*HO(1-)*3H2O

C5H4O4(2-)*Al(3+)*HO(1-)*3H2O

Conditions
ConditionsYield
With urea In water at 150℃; for 3h; Autoclave;60%
Mesaconic acid
498-24-8

Mesaconic acid

(2R)-bornane-10,2-sultam
94594-90-8

(2R)-bornane-10,2-sultam

(E)-1,4-Bis-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-methyl-but-2-ene-1,4-dione
827628-67-1

(E)-1,4-Bis-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-methyl-but-2-ene-1,4-dione

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;50%
Mesaconic acid
498-24-8

Mesaconic acid

methylamine
74-89-5

methylamine

(2S,3S)-N,3-Dimethylaspartic acid

(2S,3S)-N,3-Dimethylaspartic acid

Conditions
ConditionsYield
With potassium chloride; magnesium chloride at 30℃; for 168h; 3-methylaspartase (EC 4.3.1.2);40%
With potassium and magnesium ions In water for 72h; 3-methylaspartase;35%
Mesaconic acid
498-24-8

Mesaconic acid

methylamine
74-89-5

methylamine

(2S,3S)-N,3-Dimethyl(3-(2)H)aspartic acid

(2S,3S)-N,3-Dimethyl(3-(2)H)aspartic acid

Conditions
ConditionsYield
With potassium chloride; water-d2; magnesium chloride at 30℃; for 168h; 3-methylaspartase (EC 4.3.1.2);40%
ziconium(IV) oxychloride octahydrate
13520-92-8

ziconium(IV) oxychloride octahydrate

Mesaconic acid
498-24-8

Mesaconic acid

zirconium mesaconate

zirconium mesaconate

Conditions
ConditionsYield
With acetic acid In water at 95℃; for 5h; Microwave irradiation; Green chemistry;40%
O-Methylhydroxylamin
67-62-9

O-Methylhydroxylamin

Mesaconic acid
498-24-8

Mesaconic acid

(2S,3S)-N-Methoxy-3-methylaspartic acid

(2S,3S)-N-Methoxy-3-methylaspartic acid

Conditions
ConditionsYield
With potassium chloride; hydroxylamine; ethylamine; magnesium chloride at 30℃; for 72h; 3-methylaspartase (EC 4.3.1.2);34%
With potassium and magnesium ions In water for 72h; 3-methylaspartase;
Mesaconic acid
498-24-8

Mesaconic acid

(2S,3S)-N-Hydroxy-3-methylaspartic acid

(2S,3S)-N-Hydroxy-3-methylaspartic acid

Conditions
ConditionsYield
With potassium chloride; hydroxylamine; ethylamine; magnesium chloride at 30℃; for 72h; 3-methylaspartase (EC 4.3.1.2);19%
Mesaconic acid
498-24-8

Mesaconic acid

(1,3,5-triaza-7-phosphaadamantane)
53597-69-6

(1,3,5-triaza-7-phosphaadamantane)

3-carboxy-2-methyl-2-(1,3,5-triaza-7-phosphoniatricyclo[3.3.1.13,7]dec-7-yl)propanoate

3-carboxy-2-methyl-2-(1,3,5-triaza-7-phosphoniatricyclo[3.3.1.13,7]dec-7-yl)propanoate

Conditions
ConditionsYield
In water at 20℃; for 6574.5h; Solvent; Schlenk technique;8.5%
7-methoxy-4-vinyl-1,2-dihydronaphthalene
2811-50-9

7-methoxy-4-vinyl-1,2-dihydronaphthalene

Mesaconic acid
498-24-8

Mesaconic acid

(+/-)-7-methoxy-2-methyl-1,2,3,4,9,10-hexahydro-phenanthrene-1r,2t-dicarboxylic acid

(+/-)-7-methoxy-2-methyl-1,2,3,4,9,10-hexahydro-phenanthrene-1r,2t-dicarboxylic acid

(+/-)-7-methoxy-1-methyl-1,2,3,4,9,10-hexahydro-phenanthrene-1r,2t-dicarboxylic acid
109252-62-2

(+/-)-7-methoxy-1-methyl-1,2,3,4,9,10-hexahydro-phenanthrene-1r,2t-dicarboxylic acid

Conditions
ConditionsYield
With propionic acid
methanol
67-56-1

methanol

Mesaconic acid
498-24-8

Mesaconic acid

A

(E)-4-methoxy-3-methyl-4-oxobut-2-enoic acid
39529-95-8

(E)-4-methoxy-3-methyl-4-oxobut-2-enoic acid

B

(E)-4-methoxy-2-methyl-4-oxobut-2-enoic acid
77044-59-8

(E)-4-methoxy-2-methyl-4-oxobut-2-enoic acid

Conditions
ConditionsYield
With hydrogenchloride

498-24-8Relevant articles and documents

-

Yokoyama

, p. 1257,1258-1262 (1930)

-

Synthesis of bio-based methacrylic acid from biomass-derived itaconic acid over barium hexa-aluminate catalyst by selective decarboxylation reaction

Bohre, Ashish,Novak, Uro?,Grilc, Miha,Likozar, Bla?

, (2019/07/31)

An environmentally-benign, efficient and inexpensive high-surface-area barium hexa-aluminate (BaAl12O19, BHA) was developed as a catalyst for the decarboxylation of the biomass-derived itaconic acid (IA) to bio-based methacrylic acid (MAA). A maximal 50% final yield of MAA with a high product selectivity was obtained under relatively mild synthesis reaction conditions (250 °C; 20 bar N2). The reported selective MAA production was elevated, operating process characteristics were significantly less harsh, and no depleting critical raw materials were utilized when paralleled to the procedures with alkaline mineral bases, noble metal-containing heterogeneous catalysis systems and unrenewable feed resources (e.g. isobutene), applied previously. It was found that the doping of palladium on BHA support (Pd@BHA) did not improve MAA productivity. The effect of the time (25–300 min), temperature (175–275 °C), pressure (10–40 bar), reacting substrate concentration (0.10–0.19 mol L–1), metallic oxide mass (0.5–3.0 g) and type on IA conversion, MAA content MAA content and rates was determined, examining also recyclability. BHA catalyst was characterized with various structural techniques, such as energy-dispersive X-ray spectroscopy (EDS), X-ray powder diffraction (XRD), CO2 temperature-programmed desorption (TPD), scanning electron microscopy (SEM) and N2 physisorption.

METHOD FOR THE PRODUCTION OF METHYLSUCCINIC ACID AND THE ANHYDRIDE THEREOF FROM CITRIC ACID

-

Page/Page column 15, (2018/04/21)

A process for the preparation of methylsuccinic acid in any form, including its salts, its mono- and diester derivatives and the anhydride thereof, which comprises reacting citric acid or a derivative thereof in decarboxylation conditions, said process comprising (i) reacting citric acid or mono- and diester derivatives thereof in a non- aqueous solvent, specifically excluding alcohols, on a metallic catalyst at a temperature between 50 to 400°C and under a partial hydrogen pressure from 0.1 to 50 bar or (ii) reacting citric acid or any salt thereof or mono-, di- and triester derivatives thereof on a metallic catalyst in solvents comprising at least 5% water, at a temperature of from 50 to 400°C under a hydrogen partial pressure from 0.1 to 400 bar

Synthesis of Bio-Based Methacrylic Acid by Decarboxylation of Itaconic Acid and Citric Acid Catalyzed by Solid Transition-Metal Catalysts

Le N?tre, Jér?me,Witte-van Dijk, Susan C. M.,van Haveren, Jacco,Scott, Elinor L.,Sanders, Johan P. M.

, p. 2712 - 2720 (2016/12/23)

Methacrylic acid, an important monomer for the plastics industry, was obtained in high selectivity (up to 84 %) by the decarboxylation of itaconic acid using heterogeneous catalysts based on Pd, Pt and Ru. The reaction takes place in water at 200–250 °C without any external added pressure, conditions significantly milder than those described previously for the same conversion with better yield and selectivity. A comprehensive study of the reaction parameters has been performed, and the isolation of methacrylic acid was achieved in 50 % yield. The decarboxylation procedure is also applicable to citric acid, a more widely available bio-based feedstock, and leads to the production of methacrylic acid in one pot in 41 % selectivity. Aconitic acid, the intermediate compound in the pathway from citric acid to itaconic acid was also used successfully as a substrate.

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