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110-16-7

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110-16-7 Usage

Description

Maleic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. Its chemical formula is HO2CCHCHCO2H. Maleic acid is the cis-isomer of butenedioic acid, where as fumaric acid is the trans-isomer. It is mainly used as a precursor to fumaric acid, and relative to its parent maleic anhydride, maleic acid has few applications.

Chemical Properties

Maleic acid, also known as maleinic acid and toxilic acid, is a white crystalline (monoclinic) powder and possesses a faint acidulous odor and an astringent taste. It is soluble in water and alcohol. Maleic acid and fumaric acid are the simplest unsaturated carboxylic diacids. These acids experience two-step dissociation in aqueous solutions.They have the same structural formula but different spatial configurations. Fumaric acid is the trans and maleic acid the cis isomer. The physical properties of maleic acid and fumaric acid are very different. The cis isomer is less stable. Maleic acid is used in the preparation of fumaric acid by catalytic isomerization.

Physical properties

Maleic acid is a less stable molecule than fumaric acid. The difference in heat of combustion is 22.7 kJ·mol?1. The heat of combustion is -1355 kJ / mole. Maleic acid is more soluble in water than fumaric acid. The melting point of maleic acid (135 °C) is also much lower than that of fumaric acid (287 °C). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding that takes place in maleic acid at the expense of intermolecular interactions, and that are not possible in fumaric acid for geometric reasons.

Uses

Maleic acid is used as a precursor to fumaric acid, dimethyl maleate and glyoxalic acid. It is an electrophile and acts as dienophine in Diels-Alder reactions. It reacts with drugs to form more stable addition salts like indacaterol maleate, carfenazine, chlorpheniramine, pyrilamine, methylergonovine and thiethylperazine. Its maleate ion is useful in biochemistry as an inhibitor of transaminase reactions.

Application

Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis. It may be used to form acid addition salts with drugs to make them more stable, such as indacaterol maleate. Maleic acid is also used in manufacturing synthetic resins; in textile processing; in preserving oils and fats; to retard rancidity of fats and oils in 1:10,000 (these are said to keep 3 times longer than those without the acid); dyeing and finishing wool, cotton, and silk; preparing the maleate salts of antihistamines and similar drugs.

Production Methods

Maleic anhydride is the main source of maleic acid produced by hydration. Maleic anhydride is prepared commercially by the oxidation of benzene or by the reaction of butane with oxygen in the presence of a vanadium catalyst.

Definition

ChEBI: Maleic acid is a butenedioic acid in which the double bond has cis- (Z)-configuration. It has a role as a plant metabolite, an algal metabolite and a mouse metabolite. It is a conjugate acid of a maleate(1-) and a maleate.

Reactions

Although not practised commercially, maleic acid can be converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation (ethanol / palladium on carbon). It reacts with thionyl chloride or phosphorus pentachloride to give the maleic acid chloride (it is not possible to isolate the mono acid chloride). Maleic acid, being electrophilic, participates as a dienophile in many Diels - Alder reactions.

Synthesis Reference(s)

Journal of the American Chemical Society, 86, p. 4603, 1964 DOI: 10.1021/ja01075a017The Journal of Organic Chemistry, 60, p. 6676, 1995 DOI: 10.1021/jo00126a013Organic Syntheses, Coll. Vol. 2, p. 302, 1943

General Description

Maleic acid is a colorless crystalline solid having a faint odor. Maleic acid is combustible though Maleic acid may take some effort to ignite. Maleic acid is soluble in water. Maleic acid is used to make other chemicals and for dyeing and finishing naturally occurring fibers.

Air & Water Reactions

Soluble in water.

Reactivity Profile

Maleic acid is a colorless to white crystalline solid. Moderately toxic. When heated to decomposition Maleic acid emits irritating fumes and acrid smoke [Lewis, 3rd ed., 1993, p. 790].

Hazard

Toxic by ingestion.

Health Hazard

Inhalation causes irritation of nose and throat. Contact with eyes or skin causes irritation.

Fire Hazard

Special Hazards of Combustion Products: Irritating smoke containing maleic anhydride may form in fire.

Flammability and Explosibility

Nonflammable

Pharmaceutical Applications

Maleic acid is used in the pharmaceutical industry as a pH modifier and a buffering agent.It is also used to prevent rancidity of oils and fats; a ratio of 1 : 10 000 is usually sufficient to retard rancidity. Maleic acid is commonly used as a pharmaceutical intermediate to form the maleate salts of several categories of therapeutic agents, such as salts of antihistamines and other drug substances.

Safety Profile

Moderately toxic by ingestion and skin contact. Passes through intact skin. A skin and severe eye irritant and a corrosive. Believed to be more toxic than its isomer, fumeric acid. Combustible when exposed to heat or flame. When heated to decomposition it emits acrid smoke and irritating fumes.

Safety

Maleic acid is generally regarded as a nontoxic and nonirritant material when used at low levels as an excipient. Maleic acid is used in oral, topical, and parenteral pharmaceutical formulations in addition to food products. LD50 (mouse, oral): 2.40g/kg(7) LD50 (rabbit, skin): 1.56g/kg LD50 (rat, oral): 0.708g/kg

Potential Exposure

Maleic acid is used to make artificial resins, antihistamines, and to preserve (retard rancidity) of fats and oils

Carcinogenicity

In chronic feeding studies, 12 Osborne–Mendel rats per group were fed 0.5, 1.0, or 1.5% maleic acid in their diets for 2 years. Concentrations of 1.0 and 1.5% maleic acid retarded the growth rate of rats, and all concentrations of maleic acid increased mortality rate; no tumorigenesis was reported. Toxicological differences from controls were not marked, and the pathology was nonspecific.

storage

Maleic acid converts into the much higher-melting fumaric acid (mp: 287°C) when heated to a temperature slightly above its melting point. Maleic acid is combustible when exposed to heat or flame. The bulk material should be stored in airtight glass containers and protected from light. It is recommended not to store it above 25°C.

Shipping

UN2215 Maleic acid, Hazard class: 8; Labels: 8-Corrosive material.

Purification Methods

Crystallise the acid from acetone/pet ether (b 60-80o) or hot water. Dry it at 100o. [Beilstein 2 H 748, 2 I 303, 2 II 641, 2 III 1911, 2 IV 2199.]

Incompatibilities

Different sources of media describe the Incompatibilities of 110-16-7 differently. You can refer to the following data:
1. Dust may form explosive mixture with air, Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, amines, reducing agents; alkali metals
2. Maleic acid can react with oxidizing materials. Aqueous solutions are corrosive to carbon steels.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed. Liquid: incinerate after mixing with a flammable solvent. Use afterburner for complete combustion. Solid: dissolve in a flammable solvent or package in paper and burn. See above

Regulatory Status

Included in the FDA Inactive Ingredients Database (IM and IV injections; oral tablets and capsules; topical applications). Included in nonparenteral and parenteral medicines licensed in the UK.

Check Digit Verification of cas no

The CAS Registry Mumber 110-16-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 110-16:
(5*1)+(4*1)+(3*0)+(2*1)+(1*6)=17
17 % 10 = 7
So 110-16-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+

110-16-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Packaging
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  • Detail
  • Alfa Aesar

  • (A14596)  Maleic acid, 98+%   

  • 110-16-7

  • 250g

  • 209.0CNY

  • Detail
  • Alfa Aesar

  • (A14596)  Maleic acid, 98+%   

  • 110-16-7

  • 1000g

  • 558.0CNY

  • Detail
  • Alfa Aesar

  • (A14596)  Maleic acid, 98+%   

  • 110-16-7

  • 5000g

  • 2228.0CNY

  • Detail
  • Sigma-Aldrich

  • (92816)  Maleicacid  Standard for quantitative NMR, TraceCERT®

  • 110-16-7

  • 92816-1G

  • 1,731.60CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1272)  Maleicacid  pharmaceutical secondary standard; traceability to USP

  • 110-16-7

  • PHR1272-500MG

  • 732.19CNY

  • Detail
  • Sigma-Aldrich

  • (M0100000)  Maleicacid  European Pharmacopoeia (EP) Reference Standard

  • 110-16-7

  • M0100000

  • 1,880.19CNY

  • Detail
  • USP

  • (1374500)  Maleicacid  United States Pharmacopeia (USP) Reference Standard

  • 110-16-7

  • 1374500-300MG

  • 14,578.20CNY

  • Detail
  • Vetec

  • (V900246)  Maleicacid  Vetec reagent grade, 98%

  • 110-16-7

  • V900246-500G

  • 183.69CNY

  • Detail
  • Sigma

  • (63189)  Maleicacid  tested according to Ph.Eur.

  • 110-16-7

  • 63189-1KG

  • 2,486.25CNY

  • Detail
  • Sigma-Aldrich

  • (M0375)  Maleicacid  ReagentPlus®, ≥99.0% (HPLC)

  • 110-16-7

  • M0375-100G

  • 310.05CNY

  • Detail
  • Sigma-Aldrich

  • (M0375)  Maleicacid  ReagentPlus®, ≥99.0% (HPLC)

  • 110-16-7

  • M0375-500G

  • 552.24CNY

  • Detail
  • Sigma-Aldrich

  • (M0375)  Maleicacid  ReagentPlus®, ≥99.0% (HPLC)

  • 110-16-7

  • M0375-1KG

  • 766.35CNY

  • Detail

110-16-7SDS

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 maleic acid

1.2 Other means of identification

Product number -
Other names cis-2-Butenedioic Acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Corrosion inhibitors and anti-scaling agents,Intermediates
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:110-16-7 SDS

110-16-7Synthetic route

furan
110-00-9

furan

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With formic acid; dihydrogen peroxide at 100℃; for 1h;99%
With air; vanadia at 320℃;
With air; Bismuth vanadate at 320℃;
2-furanoic acid
88-14-2

2-furanoic acid

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With potassium hydrogencarbonate In water at 20℃; for 6h; Electrolysis;95.2%
With dihydrogen peroxide; potassium bromide; potassium hydroxide In water at 100℃; for 3h; Reagent/catalyst;87.1%
With formic acid; dihydrogen peroxide In water at 79.84℃; under 760.051 Torr; for 24h;22.4%
Acetylenedicarboxylic acid
142-45-0

Acetylenedicarboxylic acid

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With hydrogen In methanol at 20℃; under 760.051 Torr; for 5.5h; Green chemistry;94%
With hydrogen In methanol under 760.051 Torr; for 6h;92%
With water; palladium Hydrogenation;
furan-2,5-dicarboxylic acid
3238-40-2

furan-2,5-dicarboxylic acid

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With potassium hydrogencarbonate In water at 20℃; for 6h; Electrolysis;90.7%
With formic acid; dihydrogen peroxide at 100℃; for 1h;6%
With dihydrogen peroxide In water at 80℃; for 5h;40 %Chromat.
furfural
98-01-1

furfural

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With formic acid; dihydrogen peroxide at 100℃; for 0.666667h; Mechanism; Kinetics; Reagent/catalyst; Temperature; Time; Sealed tube; Green chemistry;90%
With hierarchical cobalt substituted aluminophosphate molecular sieves synthesized using 0.45 % CTAB as template at 60℃; for 3h; Reagent/catalyst;86.9%
With dihydrogen peroxide; acetic acid; methyltrioxorhenium(VII) In water at 20℃;81%
furfural
98-01-1

furfural

A

succinic acid
110-15-6

succinic acid

B

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With tetrafluoroboric acid; dihydrogen peroxide; 5 weight percent methyltrioxorhenium on polystyrene In water at 20℃; for 24h; Product distribution / selectivity;A 10%
B 90%
With dihydrogen peroxide In water at 79.84℃; under 760.051 Torr; for 24h;A 72.1%
B 13.8%
With dihydrogen peroxide In water at 79.84℃; under 760.051 Torr; for 24h; Reagent/catalyst; Schlenk technique; Green chemistry;A 74 %Chromat.
B 11 %Chromat.
With hydrogenchloride In water at 80℃; for 5h; Reagent/catalyst;A 22 %Chromat.
B 34 %Chromat.
With zinc(II) nitrate hexahydrate; dihydrogen peroxide In water at 80℃; for 5h; Reagent/catalyst;A 18 %Chromat.
B 13 %Chromat.
5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With formic acid; dihydrogen peroxide at 100℃; for 1h;89%
With potassium hydrogencarbonate In water at 20℃; for 6h; Electrolysis;49.3%
With sulfuric acid In water at 60℃; pH=1; Electrochemical reaction;35.5%
With dihydrogen peroxide In water at 80℃; for 5h;28 %Chromat.
furfural
98-01-1

furfural

A

2-furanoic acid
88-14-2

2-furanoic acid

B

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With dihydrogen peroxide; 5 weight percent methyltrioxorhenium on polystyrene In water at 20℃; Product distribution / selectivity;A 87%
B 1%
With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide In water; acetonitrile at 10℃; for 1h;A 82%
B 15%
With dihydrogen peroxide; 5 weight percent methyltrioxorhenium on polystyrene In water at 20℃; for 24h; Product distribution / selectivity;A 18%
B 82%
With water; dihydrogen peroxide at 60℃; for 4h; pH=7.5;A 45 %Spectr.
B n/a
furfural
98-01-1

furfural

A

malic acid
617-48-1

malic acid

B

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid; 5 weight percent methyltrioxorhenium on polystyrene In water at 20℃; Product distribution / selectivity;A 9%
B 84%
exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride
6118-51-0

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

A

maleic anhydride
108-31-6

maleic anhydride

B

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With formic acid In water; acetonitrile at 90℃; for 5h; Reagent/catalyst;A 82%
B 7%
furfural
98-01-1

furfural

A

2-furanoic acid
88-14-2

2-furanoic acid

B

succinic acid
110-15-6

succinic acid

C

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With tetrafluoroboric acid; dihydrogen peroxide; 5 weight percent methyltrioxorhenium on polystyrene In water at 20℃; for 24h; Product distribution / selectivity;A 9%
B 10%
C 81%
With dihydrogen peroxide; acetic acid; 5 weight percent methyltrioxorhenium on poly(4-vinylpyridine) In water at 20℃;A 41%
B 6%
C 40%
With water; dihydrogen peroxide at 60℃; for 4h; pH=6; pH-value;A 50 %Spectr.
B n/a
C n/a
2,5-diformylfurane
823-82-5

2,5-diformylfurane

A

phthalic anhydride
85-44-9

phthalic anhydride

B

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With dipotassium peroxodisulfate; water In acetonitrile at 90℃; for 5h;A 77.2%
B 14.4%
2,5-diformylfurane
823-82-5

2,5-diformylfurane

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With formic acid; dihydrogen peroxide at 100℃; for 1h;77%
With potassium hydrogencarbonate In water at 20℃; for 6h; Electrolysis;42.1%
5-hydroxy-2-(5H)-furanone
14032-66-7

5-hydroxy-2-(5H)-furanone

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With dihydrogen peroxide In water at 49.84℃; for 24h;76%
With laccase; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In acetone at 25℃; for 24h; pH=4.5; Solvent; Reagent/catalyst; pH-value; Temperature; Enzymatic reaction;
furfural
98-01-1

furfural

A

2-buten-4-olide
497-23-4

2-buten-4-olide

B

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid In water at 60℃; for 24h; Green chemistry;A 71%
B 11%
With dihydrogen peroxide; potassium bromide; potassium hydroxide In water at 100℃; for 3h; Concentration;A 7.1%
B 51.9%
5-hydroxymethyl-furan-2-carboxylic acid
6338-41-6

5-hydroxymethyl-furan-2-carboxylic acid

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With potassium hydrogencarbonate In water at 20℃; for 6h; Electrolysis;67.8%
(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With triethanolamine; C33H21IrN3O9S3(3-) In water for 20h; Alkaline conditions; Inert atmosphere; Irradiation;66%
With ethanol Irradiation.UV-Licht;
entsteht das Anhydrid;
furfural
98-01-1

furfural

A

2-furanoic acid
88-14-2

2-furanoic acid

B

succinic acid
110-15-6

succinic acid

C

maleic acid
110-16-7

maleic acid

D

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

Conditions
ConditionsYield
With dihydrogen peroxide; 1-butyl-3-methylimidazolium Tetrafluoroborate; methyltrioxorhenium(VII) In water at 20℃;A 7%
B 12%
C 66%
D 13%
furfural
98-01-1

furfural

A

2-furanoic acid
88-14-2

2-furanoic acid

B

malic acid
617-48-1

malic acid

C

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane; water; acetonitrile at 20℃;A 10%
B 8%
C 66%
furfural
98-01-1

furfural

A

succinic acid
110-15-6

succinic acid

B

2-buten-4-olide
497-23-4

2-buten-4-olide

C

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With formic acid; dihydrogen peroxide; sodium sulfate In water; ethyl acetate at 59.84℃; for 3h; Kinetics; Solvent; Reagent/catalyst; Temperature; Concentration;A 8.5%
B 61.5%
C 6.7%
With potassium chloride; dihydrogen peroxide; potassium hydroxide In water at 100℃; for 3h; Reagent/catalyst;A 24.2%
B 10.4%
C 41.2%
With formic acid; dihydrogen peroxide; sodium sulfate In water at 59.84℃; for 3h; Kinetics; Solvent; Reagent/catalyst;A 38.3%
B 12.8%
C 17.3%
furfural
98-01-1

furfural

A

maleic acid
110-16-7

maleic acid

B

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

Conditions
ConditionsYield
With dihydrogen peroxide; acidine In water at 100℃; for 0.5h; Temperature;A 61%
B 31%
With dihydrogen peroxide; acidine In water at 100℃; for 2h; Time;A 10%
B 48%
With sodium chlorate; vanadium pentoxide In water at 85 - 95℃; for 19h;A n/a
B 47%
With sodium chlorate; vanadia In water at 80 - 90℃; for 13h; Overall yield = 58 %; Overall yield = 42.3 g;A n/a
B n/a
With choline chloride; dihydrogen peroxide; oxalic acid In water at 50℃; for 24h; Reagent/catalyst; Green chemistry; Overall yield = 95.7 %Chromat.;
malic acid
617-48-1

malic acid

A

maleic acid
110-16-7

maleic acid

B

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

C

acrylic acid
79-10-7

acrylic acid

Conditions
ConditionsYield
sodium hydroxide In water at 340℃; under 129290 Torr; pH=3.17; Product distribution / selectivity;A 10.52%
B 6.88%
C 59.23%
furfural
98-01-1

furfural

A

5-hydroxy-2-(5H)-furanone
14032-66-7

5-hydroxy-2-(5H)-furanone

B

formic acid
64-18-6

formic acid

C

malic acid
617-48-1

malic acid

D

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With dihydrogen peroxide In water at 49.84℃; for 24h; Catalytic behavior; Temperature; Concentration;A n/a
B n/a
C n/a
D 57%
5-Formyl-2-furancarboxylic acid
13529-17-4

5-Formyl-2-furancarboxylic acid

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With potassium hydrogencarbonate In water at 20℃; for 6h; Electrolysis;56.9%
With formic acid; dihydrogen peroxide at 100℃; for 1h;33%
malic acid
617-48-1

malic acid

A

maleic acid
110-16-7

maleic acid

B

acrylic acid
79-10-7

acrylic acid

Conditions
ConditionsYield
sodium hydroxide In water at 345℃; under 181007 Torr; pH=3.31; Product distribution / selectivity;A 5.22%
B 56.18%
Conditions
ConditionsYield
With silver nitrate at 100℃; Product distribution; Rate constant; Thermodynamic data; study of the oxidation reaction of D-lyxose by silver ion, kinetic mesurements, ΔS(excit.),;A 10%
B 8%
C 55%
D 6%
5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

A

glycolic Acid
79-14-1

glycolic Acid

B

malic acid
617-48-1

malic acid

C

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII) In water; acetic acid at 20℃;A 55%
B 29%
C 14%
5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

A

furan-2,5-dicarboxylic acid
3238-40-2

furan-2,5-dicarboxylic acid

B

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With sulfuric acid In water at 60℃; pH=1; Electrochemical reaction;A 54%
B n/a
methanol
67-56-1

methanol

maleic acid
110-16-7

maleic acid

dimethyl cis-but-2-ene-1,4-dioate
624-48-6

dimethyl cis-but-2-ene-1,4-dioate

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
With sulfuric acid at 75℃; for 16h;97%
With sulfuric acid at 75℃; for 16h; Reflux;97%
maleic acid
110-16-7

maleic acid

succinic acid
110-15-6

succinic acid

Conditions
ConditionsYield
With palladium/alumina; hydrogen In water at 80℃; for 6.5h;100%
With samarium diiodide In tetrahydrofuran for 0.0833333h; Ambient temperature;99%
With hydrogen; NPF-1 (palladium 0.2 wt percent, nickel 0.2 wt percent, iron 0.07 wt percent on carbon) modified with maleic acid In water at 90 - 100℃; under 15201 Torr; Product distribution / selectivity; Autoclave; Inert atmosphere;99.5%
maleic acid
110-16-7

maleic acid

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

Conditions
ConditionsYield
With (E)-4-(2-chlorostyryl)pyridine In methanol at 20℃; for 720h;100%
With maleic anhydride In water at 190℃; for 6h; Reagent/catalyst; Inert atmosphere; Autoclave; Green chemistry;99.5%
With N-Bromosuccinimide; dibenzoyl peroxide; acetic acid for 6h; Heating;90%
S,S-Di(n-propyl) dithiocarbonate
10596-56-2

S,S-Di(n-propyl) dithiocarbonate

maleic acid
110-16-7

maleic acid

(+/-)-propylsulfanyl-succinic acid
45015-91-6

(+/-)-propylsulfanyl-succinic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol; water for 8h; Heating;100%
2-(vinyloxy)ethyl isothiocyanate
59565-09-2

2-(vinyloxy)ethyl isothiocyanate

maleic acid
110-16-7

maleic acid

(Z)-But-2-enedioic acid bis-[1-(2-isothiocyanato-ethoxy)-ethyl] ester

(Z)-But-2-enedioic acid bis-[1-(2-isothiocyanato-ethoxy)-ethyl] ester

Conditions
ConditionsYield
at 90 - 100℃; for 1h;100%
3-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)propan-1-amine
2095-14-9

3-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)propan-1-amine

maleic acid
110-16-7

maleic acid

10-(3-aminopropyl)-2-trifluoromethyl-10H-phenothiazine maleate

10-(3-aminopropyl)-2-trifluoromethyl-10H-phenothiazine maleate

Conditions
ConditionsYield
In ethanol100%
maleic acid
110-16-7

maleic acid

1,2-cis-2,3-trans-3,4-cis-cyclobutane-1,2,3,4-tetracarboxylic acid
38841-00-8

1,2-cis-2,3-trans-3,4-cis-cyclobutane-1,2,3,4-tetracarboxylic acid

Conditions
ConditionsYield
at 20℃; for 100h; Photolysis;100%
maleic acid
110-16-7

maleic acid

dihydro-2(3H)furanone-[3,4,5,5-D4]

dihydro-2(3H)furanone-[3,4,5,5-D4]

Conditions
ConditionsYield
With deuterium; Ru4H4(CO)8(PBu3)4 In tetrahydrofuran at 180℃; for 48h;100%
maleic acid
110-16-7

maleic acid

disodium cis-epoxysuccinate

disodium cis-epoxysuccinate

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide; sodium tungstate In water at 65 - 70℃; for 1.75h; pH=2 - 5.5;100%
maleic acid
110-16-7

maleic acid

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
With hydrogen In water100%
With hydrogen In water100%
With hydrogen In water100%
6-((1SR,3RS)-3-{2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethylamino}cyclopentylmethylamino)nicotinonitrile

6-((1SR,3RS)-3-{2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethylamino}cyclopentylmethylamino)nicotinonitrile

maleic acid
110-16-7

maleic acid

6-((1SR,3RS)-3-{2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethylamino}cyclopentylmethylamino)nicotinonitrile maleate

6-((1SR,3RS)-3-{2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethylamino}cyclopentylmethylamino)nicotinonitrile maleate

Conditions
ConditionsYield
In acetone at 20℃; for 0.333333h;100%
(+/-)-4-(3-chloro-1H-indol-6-yl)-2-methyl-1,2,3,4-tetrahydroisoquinoline

(+/-)-4-(3-chloro-1H-indol-6-yl)-2-methyl-1,2,3,4-tetrahydroisoquinoline

maleic acid
110-16-7

maleic acid

(+/-)-4-(3-chloro-1H-indol-6-yl)-2-methyl-1,2,3,4-tetrahydroisoquinoline maleate

(+/-)-4-(3-chloro-1H-indol-6-yl)-2-methyl-1,2,3,4-tetrahydroisoquinoline maleate

Conditions
ConditionsYield
In methanol; dichloromethane for 1h;100%
endo-N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-2-(2-morpholinophenyl)benzoxazole-4-carboxamide

endo-N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-2-(2-morpholinophenyl)benzoxazole-4-carboxamide

maleic acid
110-16-7

maleic acid

endo-N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-2-(2-morpholinophenyl)benzoxazole-4-carboxamide maleate

endo-N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-2-(2-morpholinophenyl)benzoxazole-4-carboxamide maleate

Conditions
ConditionsYield
In methanol; acetonitrile100%
endo-N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-2-[2-(4-methylpiperazin-1-yl)phenyl]benzoxazole-4-carboxamide

endo-N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-2-[2-(4-methylpiperazin-1-yl)phenyl]benzoxazole-4-carboxamide

maleic acid
110-16-7

maleic acid

endo-N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-2-[2-(4-methylpiperazin-1-yl)phenyl]benzoxazole-4-carboxamide maleate

endo-N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-2-[2-(4-methylpiperazin-1-yl)phenyl]benzoxazole-4-carboxamide maleate

Conditions
ConditionsYield
In methanol; acetonitrile100%
sodium tungstate

sodium tungstate

concentrated sodium hydroxide

concentrated sodium hydroxide

maleic acid
110-16-7

maleic acid

disodium cis-oxirane-1,2-dicarboxylate

disodium cis-oxirane-1,2-dicarboxylate

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide In water; acetone100%
2-[((2S)-1'-{2-[(2R)-4-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dichlorophenyl)morpholin-2-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl)oxy]-N-(4-hydroxybutyl)-N-methylacetamide
863613-79-0

2-[((2S)-1'-{2-[(2R)-4-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dichlorophenyl)morpholin-2-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl)oxy]-N-(4-hydroxybutyl)-N-methylacetamide

maleic acid
110-16-7

maleic acid

2-[((2S)-1'-{2-[(2R)-4-[3,5-bis(Trifluoromethyl)benzoyl]-2-(3,4-dichlorophenyl)morpholin-2-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl)oxy]-N-(4-hydroxybutyl)-N-methylacetamide maleate

2-[((2S)-1'-{2-[(2R)-4-[3,5-bis(Trifluoromethyl)benzoyl]-2-(3,4-dichlorophenyl)morpholin-2-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl)oxy]-N-(4-hydroxybutyl)-N-methylacetamide maleate

Conditions
ConditionsYield
In ethanol100%
6-(5-(4-chlorophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yl)pyridazin-3-amine

6-(5-(4-chlorophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yl)pyridazin-3-amine

maleic acid
110-16-7

maleic acid

(+/-)-6-(5-(4-chlorophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yl)pyridazin-3-amine maleate

(+/-)-6-(5-(4-chlorophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yl)pyridazin-3-amine maleate

Conditions
ConditionsYield
In methanol; water100%
meloxicam
71125-38-7

meloxicam

maleic acid
110-16-7

maleic acid

4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide maleic acid (1:1)
1174325-93-9

4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide maleic acid (1:1)

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h;100%
In tetrahydrofuran Product distribution / selectivity;
In ethyl acetate for 19h; Solvent;
In tetrahydrofuran at 20℃; for 24h;
N-butylamine
109-73-9

N-butylamine

maleic acid
110-16-7

maleic acid

N1, N4-dibutylmaleamide
94267-98-8

N1, N4-dibutylmaleamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0 - 20℃; for 18h;100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran for 18h; Cooling with ice;
agomelatine
138112-76-2

agomelatine

maleic acid
110-16-7

maleic acid

agomelatine maleic acid
1403960-82-6

agomelatine maleic acid

Conditions
ConditionsYield
In ethanol for 0.75h;100%
In methanol; ethyl acetate at 20℃; for 168h; Product distribution / selectivity;
for 1h;
maleic acid
110-16-7

maleic acid

pregabilin
148553-50-8

pregabilin

(S)-3-(aminomethyl)-5-methylhexanoic acid maleate
1414928-41-8

(S)-3-(aminomethyl)-5-methylhexanoic acid maleate

Conditions
ConditionsYield
In 2-methylpropyl acetate for 0.75h; Product distribution / selectivity;100%
(E)-N-[4-[[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolinyl]-3-[(2R)-1-methylpyrrolidin-2-yl]propan-2-enoylamine
1269662-73-8

(E)-N-[4-[[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolinyl]-3-[(2R)-1-methylpyrrolidin-2-yl]propan-2-enoylamine

maleic acid
110-16-7

maleic acid

(E)-N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]-3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enamide maleate

(E)-N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]-3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enamide maleate

Conditions
ConditionsYield
In dichloromethane at 20 - 30℃; for 1h; Inert atmosphere;100%
In dichloromethane at 20 - 30℃; for 1h;100%
N,N-bis-(phenylcarbamoylmethyl)dimethylammonium hydroxide
1577003-07-6

N,N-bis-(phenylcarbamoylmethyl)dimethylammonium hydroxide

maleic acid
110-16-7

maleic acid

N,N-bis-(phenylcarbamoylmethyl)dimethylammonium maleate
1577003-12-3

N,N-bis-(phenylcarbamoylmethyl)dimethylammonium maleate

Conditions
ConditionsYield
In isopropyl alcohol at 25 - 40℃; for 6h;100%
methyldiallylamine
2424-01-3

methyldiallylamine

maleic acid
110-16-7

maleic acid

C7H13N*C4H4O4

C7H13N*C4H4O4

Conditions
ConditionsYield
In water at 25℃; for 0.5h;100%
tandospirone
87760-53-0

tandospirone

maleic acid
110-16-7

maleic acid

tandospirone maleic acid

tandospirone maleic acid

Conditions
ConditionsYield
In ethanol; water at 70℃; Temperature; Solvent; Large scale;99.9%
5-(4-cyclopropyl-1H-imidazol-1-yl)-N-(6-(6,7-dihydro-5H-pyrrolo-[2,1-c][1,2,4 ]triazol-3-yl)pyridin-2-yl)-2-fluoro-4-methylbenzamide

5-(4-cyclopropyl-1H-imidazol-1-yl)-N-(6-(6,7-dihydro-5H-pyrrolo-[2,1-c][1,2,4 ]triazol-3-yl)pyridin-2-yl)-2-fluoro-4-methylbenzamide

maleic acid
110-16-7

maleic acid

C24H22FN7O*C4H4O4

C24H22FN7O*C4H4O4

Conditions
ConditionsYield
In tetrahydrofuran for 8h; Solvent;99.7%
4-methyl-6-[1'-(5-methylpyrazin-2-yl)-4,4'-bipiperidin-1-yl]pyrimidine-2-carbonitrile
1039743-15-1

4-methyl-6-[1'-(5-methylpyrazin-2-yl)-4,4'-bipiperidin-1-yl]pyrimidine-2-carbonitrile

maleic acid
110-16-7

maleic acid

C4H4O4*C21H27N7

C4H4O4*C21H27N7

Conditions
ConditionsYield
In tetrahydrofuran at 35℃;99.4%
maleic acid
110-16-7

maleic acid

1,2-dimethyl-5-vinylpyridinium methyl sulfate

1,2-dimethyl-5-vinylpyridinium methyl sulfate

polymer, 98.6 mol percent of 1,2-dimethyl-5-vinylpyridinium methyl sulfate, [η] = 2.05 dl/g; monomer(s): 1,2-dimethyl-5-vinylpyridinium methyl sulfate; maleic acid

polymer, 98.6 mol percent of 1,2-dimethyl-5-vinylpyridinium methyl sulfate, [η] = 2.05 dl/g; monomer(s): 1,2-dimethyl-5-vinylpyridinium methyl sulfate; maleic acid

Conditions
ConditionsYield
With 1-tert-butylperoxy-propan-2-ol In water at 20℃;99%
maleic acid
110-16-7

maleic acid

1,2-dimethyl-5-vinylpyridinium methyl sulfate

1,2-dimethyl-5-vinylpyridinium methyl sulfate

polymer, 97.0 mol percent of 1,2-dimethyl-5-vinylpyridinium methyl sulfate, [η] = 1.71 dl/g; monomer(s): 1,2-dimethyl-5-vinylpyridinium methyl sulfate; maleic acid

polymer, 97.0 mol percent of 1,2-dimethyl-5-vinylpyridinium methyl sulfate, [η] = 1.71 dl/g; monomer(s): 1,2-dimethyl-5-vinylpyridinium methyl sulfate; maleic acid

Conditions
ConditionsYield
With 1-tert-butylperoxy-propan-2-ol In water at 20℃;99%

110-16-7Related news

Nanocellulose production from recycled paper mill sludge using ozonation pretreatment followed by recyclable Maleic acid (cas 110-16-7) hydrolysis08/24/2019

Nanocellulose (NC) have garnered much interest worldwide due to its physical and chemical properties. Nanocellulose is produced from biomass materials by bleaching pretreatment, followed by acid hydrolysis. This work demonstrated the production of NC from recycled paper sludge (RPS), a crystalli...detailed

110-16-7Relevant articles and documents

-

Yokoyama,Yamamoto

, p. 121,123 (1943)

-

-

Yokoyama,Ishikawa

, p. 275,281 (1931)

-

Fabrication of a stable Ti/Pb-TiOxNWs/PbO2 anode and its application in benzoquinone degradation

Guo, Yingjuan,Tang, Changbin,Xue, Juanqin,Yu, Lihua,Zhang, Lihua

, (2021)

To delay passivation of a titanium (Ti) substrate as well as enhance adhesion between an electrodeposited PbO2 coating and the Ti substrate, a titanium-lead composite oxide nanowire (Pb-TiOxNWs) intermediate layer was formed in situ on the surface of porous Ti by alkali etching, ion substitution, and high-temperature calcination. At the same time, Ti/PbO2 and Ti/TiO2NWs/PbO2 electrodes with porous Ti as a matrix were prepared for comparison. The surface structure and morphology of the prepared intermediate layer and the PbO2 coating were characterized by scanning electron microscopy (SEM), X-ray diffraction (XRD), and X-ray photoelectron spectroscopy (XPS). The influences of the composite oxide intermediate layer on the electrochemical performance of the PbO2 electrode were analyzed by cyclic voltammetry (CV), linear sweep voltammetry (LSV), and AC impedance spectroscopy (EIS). Accelerated lifetime tests were performed for electrodes with and without different intermediate layers. The results showed that PbOx was incorporated into the titanium dioxide three-dimensional network structure, resulting in formation of Pb-TiOxNWs. The surface of the Ti/Pb-TiOxNWs/PbO2 electrode was denser due to the smaller particle size of PbO2. The preferred crystal orientation of β(110) was observed for PbO2 deposited on Ti/Pb-TiOxNWs. The oxygen evolution potential reached a maximum of 2.19 V for Ti/Pb-TiOxNWs/PbO2. Accelerated life tests showed that compared with Ti/PbO2 and Ti/TiO2NWs/PbO2, the electrode life of Ti/Pb-TiOxNWs/PbO2 was increased by 91.7% and 35.3%, respectively. Therefore, it can be concluded that significantly improved morphology and electrochemical performance were achieved for titanium-based PbO2 electrodes by the addition of a Pb-TiOxNWs intermediate layer. In particular, the electrochemical stability of the PbO2 coating electrodes was improved markedly by the Pb-TiOxNWs intermediate layer. The electrodes were used for electrochemical oxidation of benzoquinone in wastewater (100 mg/L). It was found that chloride ions played a critical role in improving the current efficiency of electro-oxidative degradation. Under the same conditions, the COD removal rate in the presence of NaCl was 45% higher than in the presence of sulfate. The results of HPLC analysis of the intermediate products indicated that the oxidants electro-generated by chloride ions had stronger ring-opening and mineralization capabilities than those electro-generated by sulfate ions.

Reactions of Ozone with 1-(m-Substituted phenylazo)-2-naphthol-6-sulfonic Acids in Aqueous Solutions

Onari, Yasuo

, p. 2526 - 2530 (1985)

The substituent effect on the ozone decoloration of 1-(m-substituted phenylazo)-2-naphthol-6-sulfonic acids (PANSA) in aqueous solutions was investigated.Both the acidities of PANSA and the variation of the ozone decoloration rates of them increased compared to those of the corresponding 1-(m-substituted phenylazo)-2-naphthol-3,6-disulfonic acids (PANDSA).The relationships between the decoloration rates and the indexes (pKOH and ?m values) of the basicities of the dyes, however, indicated nearly the same characteristics between the data of these two series of dyes, and the ozone decoloration reactions of PANSA appeared to proceed by nearly the same mechanism as those of PANDSA.The changes of the keto-enol ratios of the dyes with their ozone decolorations suggested that the decoloration rates might rise as the reduction rates of their keto-enol ratios increased.It seems likely that the chief organic product that was finally produced in these resctions is oxalic acid.

-

Parks,Yula

, p. 891,896 (1941)

-

Degradation of the Cellulosic Key Chromophore 5,8-Dihydroxy-[1,4]-naphthoquinone by Hydrogen Peroxide under Alkaline Conditions

Zwirchmayr, Nele Sophie,Hosoya, Takashi,Henniges, Ute,Gille, Lars,Bacher, Markus,Furtmüller, Paul,Rosenau, Thomas

, p. 11558 - 11565 (2017)

5,8-Dihydroxy-[1,4]-naphthoquinone (DHNQ) is one of the key chromophores in cellulosic materials. Its almost ubiquitous presence in cellulosic materials makes it a target molecule of the pulp and paper industry's bleaching efforts. In the presented study, DHNQ was treated with hydrogen peroxide under alkaline conditions at pH 10, resembling the conditions of industrial hydrogen peroxide bleaching (P stage). The reaction mechanism, reaction intermediates, and final degradation products were analyzed by UV/vis, NMR, GC-MS, and EPR. The degradation reaction yielded C1-C4 carboxylic acids as the final products. Highly relevant for pulp bleaching are the findings on intermediates of the reaction, as two of them, 2,5-dihydroxy-[1,4]-benzoquinone (DHBQ) and 1,4,5,8-naphthalenetetrone, are potent chromophores themselves. While DHBQ is one of the three key cellulosic chromophores and its degradation by H2O2 is well-established, the second intermediate, 1,4,5,8-naphthalenetetrone, is reported for the first time in the context of cellulose discoloration.

Synthesis of maleic acid from renewable resources: Catalytic oxidation of furfural in liquid media with dioxygen

Shi, Song,Guo, Huajun,Yin, Guochuan

, p. 731 - 733 (2011)

Developing novel technologies to obtain fuel and organic chemicals from renewable resources has been the immediate issue in academic and industrial communities. The present work introduces a new route to synthesize maleic acid from the renewable furfural. The current data reveal that, using dioxygen as oxidant, the simple copper salts can catalyze oxidation of furfural to maleic acid in aqueous solution. The combination of copper nitrate with phosphomolybdic acid could achieve a 49.2% yield of maleic acid with selectivity of 51.7%. The major challenge for this route is how to avoid the polymerization of furfural to resins under oxidative conditions.

An electrocatalytic route for transformation of biomass-derived furfural into 5-hydroxy-2(5H)-furanone

Wu, Haoran,Song, Jinliang,Liu, Huizhen,Xie, Zhenbing,Xie, Chao,Hu, Yue,Huang, Xin,Hua, Manli,Han, Buxing

, p. 4692 - 4698 (2019)

Development of efficient strategies for biomass valorization is a highly attractive topic. Herein, we conducted the first work on electrocatalytic oxidation of renewable furfural to produce the key bioactive intermediate 5-hydroxy-2(5H)-furanone (HFO). It was demonstrated that using H2O as the oxygen source and metal chalcogenides (CuS, ZnS, PbS, etc.) as electrocatalysts, the reaction could proceed efficiently, and the CuS nanosheets prepared in this work showed the best performance and provided high HFO selectivity (83.6%) and high conversion (70.2%) of furfural. In addition, the CuS electrocatalyst showed long-term stability. Mechanism investigation showed that furfural was oxidized to HFO via multistep reactions, including C-C cleavage, subsequent ring opening and oxidation, and intramolecular isomerization.

Active sites in vanadia/titania catalysts for selective aerial oxidation of β-picoline to nicotinic acid

Srinivas, Darbha,Hoelderich, Wolfgang F.,Kujath, Steffen,Valkenberg, Michael H.,Raja, Thirumalaiswamy,Saikia, Lakshi,Hinze, Ramona,Ramaswamy, Veda

, p. 165 - 173 (2008)

Vanadia/titania catalysts with varying vanadium content were prepared by impregnation using three different titania carrier materials of varying surface area. The structure of active vanadium species for β-picoline oxidation was investigated. Vanadium is mainly in the +5 oxidation state as revealed by electron paramagnetic resonance (EPR) and 51V magic-angle spinning nuclear magnetic resonance (51V MAS NMR) spectroscopy techniques. Diffuse reflectance UV-visible (DRUV-vis) spectroscopy and spectral deconvolution enabled identification of at least five different types of vanadium oxide species in these catalysts: monomeric tetrahedral VO3-4, polymeric distorted tetrahedral VO-3, square pyramidal V2O5, octahedral V2O2-6 and V4+ oxide species. While both VO3-4 and VO-3 species are active in β-picoline oxidation, the latter having a distorted tetrahedral geometry yielded the desired products-picolinaldehyde and nicotinic acid. High surface area, anatase structure for the support and dispersed, distorted tetrahedral vanadium oxide species are the key parameters determining the activity and selectivity of these oxidation catalysts.

Robust selenium-doped carbon nitride nanotubes for selective electrocatalytic oxidation of furan compounds to maleic acid

Huang, Xin,Song, Jinliang,Hua, Manli,Chen, Bingfeng,Xie, Zhenbing,Liu, Huizhen,Zhang, Zhanrong,Meng, Qinglei,Han, Buxing

, p. 6342 - 6349 (2021)

Selective oxidation of biomass-derived furan compounds to maleic acid (MA), an important bulk chemical, is a very attractive strategy for biomass transformation. However, achieving a high MA selectivity remains a great challenge. Herein, we for the first time successfully designed and fabricated Se-doped graphitic carbon nitride nanotubes with a chemical formula of C3.0N-Se0.03. The prepared C3.0N-Se0.03 was highly efficient for electrocatalytic oxidation of various biomass-derived furan compounds to generate MA. At ambient conditions, the MA yield could reach 84.2% from the electro-oxidation of furfural. Notably, the substituents on the furan ring significantly affected the selectivity to MA, following the order: carboxyl group > aldehyde group > hydroxyl group. Detailed investigation revealed that Se doping could tune the chemical structure of the materials (e.g., C3.0N-Se0.03 and g-C3N4), thus resulting in the change in catalytic mechanism. The excellent performance of C3.0N-Se0.03 originated from the suitable amount of graphitic N and its better electrochemical properties, which significantly boosted the oxidation pathway to MA. This work provides a robust and selective metal-free electrocatalyst for the sustainable synthesis of MA from oxidation of biomass-derived furan compounds. This journal is

Synthesis, analysis and possibility application of cyclic and linear forms of poly(aspartic acid) synthesized under microwave irradiation

Pielichowski,Polaczek,Hebda

, p. 120 - 127 (2010)

In this paper a new original method of synthesis of poly(aspartic acid) (PAA) from aspartic acid (AA) or maleic anhydride under microwave irradiation is presented. The syntheses carried out mainly without the catalyst, received higher yield in comparison for conventional method. PAA has been characterized by nuclear magnetic resonance (1H NMR, 13C NMR), infrared spectroscopy (FT-IR) and termogravimetric analysis (Tg). Obtained polymer we used for several diversified applications, such as, medicine, agriculture and catalyst for oxidation reactions. Taylor & Francis Group, LLC.

-

Faith,Yantzi

, p. 1988 (1938)

-

Hetero-mixed TiO2-SnO2 interfaced nano-oxide catalyst with enhanced activity for selective oxidation of furfural to maleic acid

Malibo, Petrus M.,Makgwane, Peter R.,Baker, Priscilla G.L.

, (2021)

Herein we report on the catalytic activity of hetero-mixed TiO2-SnO2 nano-oxide catalyst for the selective liquid-phase oxidation of furfural to maleic acid using H2O2 oxidant. The high surface area and strong interaction of the two oxides with modified electronic structure manifested enhanced effective oxygen vacancies, and redox activity performance of the TiO2-SnO2 catalyst for furfural oxidation reaction. The structure of the catalyst was investigated by the powder X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), high-resolution transition electron microscopy (HRTEM), electron paramagnetic resonance (EPR) and Brunauer-Emmett-Teller (BET) surface area analyser techniques. The interfaced TiO2-SnO2 oxide catalyst was more catalytically active than its single counterpart SnO2 and TiO2 oxides to give a furfural conversion of 96.2% at up to 63.8% yield of maleic acid. The catalytic performance shown by TiO2-SnO2 present encouraging prospects for an economical solid metal oxide catalyst to access biobased maleic acid from renewable biomass-derived furfural.

In-situ fabrication of 0D/2D NiO/Bi12O17Cl2 heterojunction towards high-efficiency degrading 2, 4-dichlorophenol and mechanism insight

Song, Ning,Li, Jiaming,Li, Chunmei,Zhou, Pengjie,Jiang, Enhui,Zhang, Xiaoxu,Liu, Chunbo,Wu, Zhichen,Zheng, Hang,Che, Guangbo,Dong, Hongjun

, (2020)

2, 4-dichlorophenol (2, 4-DCP) as a persistent pollutant is frequently detected in water environments, complete eradication of trace which in water is an important task. Hence, a 0D/2D NiO/Bi12O17Cl2 heterojunction was achieved by in-situ fabrication of NiO nanodots on Bi12O17Cl2 nanosheets, which obviously improved the physical, optical and photoelectrochemical properties. The photocatalytic degradation activity of 0D/2D NiO/Bi12O17Cl2 heterojunction was boosted dramatically, which originated from the improved transfer and separation efficiency of charge carriers owing to the formation of Z-scheme heterostructure between NiO and Bi12O17Cl2. The possible photocatalytic reaction mechanism including migration behaviors of charge carriers, generation of reactive species and degradation intermediate products were revealed in depth. This work provides the valuable experiences for designing and fabricating otherwise 0D/2D heterojunction photocatalysts in the application of environmental treating fields.

Highly efficient formic acid-mediated oxidation of renewable furfural to maleic acid with H2O2

Li, Xiukai,Ho, Ben,Lim, Diane S. W.,Zhang, Yugen

, p. 914 - 918 (2017)

Maleic acid and its anhydride are important intermediates in the chemical industry produced on a multimillion tonne-scale annually. The synthesis of maleic acid/anhydride from renewable biomass resources such as furfural and 5-hydroxymethylfurfural is highly desirable for the sustainability of human society. Most of the previously reported processes for maleic acid/anhydride synthesis from biomass suffer from low efficiency, complicated conditions and poor catalyst recyclability. Herein, we demonstrate a highly efficient and simple system for the synthesis of maleic acid from furfural. An excellent yield (95%) of maleic acid was achieved under mild conditions in this very simple system which requires only H2O2 as an oxidant in formic acid solvent. Under similar conditions, an 89% yield of maleic acid was achieved from biomass-derived 5-hydroxymethylfurfural. This study presents a novel synthetic method and a promising process for maleic acid production from renewable biomass resources.

Degradation of chlorinated phenols in water in the presence of H 2O2 and water-soluble μ-nitrido diiron phthalocyanine

Colomban, Cédric,Kudrik, Evgeny V.,Afanasiev, Pavel,Sorokin, Alexander B.

, p. 14 - 19 (2014)

Efficient disposal of pollutants is a key problem in the environmental context. In particular, chlorinated aromatic compounds are recalcitrant to biodegradation and conventional treatment methods. Iron phthalocyanines were previously shown to be efficient catalysts for the oxidative degradation of chlorinated phenols considered as priority pollutants. We have recently discovered μ-nitrido diiron phthalocyanines as powerful oxidation catalysts. Herein, we evaluate these emerging catalysts in the oxidation of chlorinated phenols in comparison with conventional mononuclear complex. Catalytic performance of iron tetrasulfophthalocyanine (FePcS) and corresponding μ-nitrido dimer [(FePcS)2N] have been compared in the oxidation of chlorinated phenols by hydrogen peroxide in water. The oxidative degradation of 2,6-dichlorophenol (DCP) and 2,4,6-trichlorophenol (TCP) has been studied. The (FePcS)2N exhibited better catalytic properties than mononuclear FePcS in terms of conversion and mineralization (transformation of organic chlorine to Cl- and decrease of total organic carbon due to the formation of CO2). Kinetics of the DCP oxidation indicated that different reaction mechanisms are involved in the presence of FePcS and (FePcS)2N. The high catalytic activity of (FePcS)2N in the degradation and mineralization of chlorinated phenols make μ-nitrido diiron phthalocyanines promising catalyst to apply also in environmental remediation.

Remarkable Reactivity of Boron-Substituted Furans in the Diels-Alder Reactions with Maleic Anhydride

Medrán, Noelia S.,Dezotti, Federico,Pellegrinet, Silvina C.

, p. 5068 - 5072 (2019)

The reactivity of boron-substituted furans as dienes in the Diels-Alder reaction with maleic anhydride has been investigated. Gratifyingly, the furans with boryl substituents at C-3 gave the exo cycloadduct exclusively with excellent yields. In particular, the potassium trifluoroborate exhibited outstanding reactivity at room temperature. Theoretical calculations suggested that the trifluoroborate group is highly activating and also that the thermodynamics is the main factor that determines whether the products can be obtained efficiently or not.

Synthesis of maleic and fumaric acids from furfural in the presence of betaine hydrochloride and hydrogen peroxide

Araji,Madjinza,Chatel,Moores,Jér?me,De Oliveira Vigier

, p. 98 - 101 (2017)

Here we report the successful valorisation of furfural into maleic acid (MA) and fumaric acid (FA) with a total yield above 90% using an aqueous solution of betaine hydrochloride (BHC) in the presence of hydrogen peroxide. BHC can be recycled for at least 4 cycles and it can be used to directly convert xylose to MA and FA.

Effect of Al and Ce on Zr-pillared bentonite and their performance in catalytic oxidation of phenol

Mnasri-Ghnimi, Saida,Frini-Srasra, Najoua

, p. 1766 - 1773 (2016)

Catalysts based on pillared clays with Zr and/or Al and Ce–Zr and/or Al polycations have been synthesized from a Tunisian bentonite and tested in catalytic oxidation of phenol at 298 K. The Zr-pillared clay showed higher activity than the Al-one in phenol oxidation. Mixed Zr–Al pillars lead to an enhancement of the catalytic activity due to the modification of the zirconium properties. The clays modified with Ce showed high conversions of phenol and TOC thus showing to be very selective towards the formation of CO2 and H2O.

Facile preparation of a Ti/α-PbO2/β-PbO2 electrode for the electrochemical degradation of 2-chlorophenol

Zhang, Qianli,Guo, Xinyan,Cao, Xiaodan,Wang, Dongtian,Wei, Jie

, p. 975 - 981 (2015)

A Ti/α-PbO2/β-PbO2 electrode with high stability was prepared and examined toward the electrochemical degradation of 2-chlorophenol. Scanning electron microscopy analysis revealed that Ti/α-PbO2/β-PbO2 had a cauliflower morphology comprising small β-PbO2 crystals. The 2-chlorophenol removal rate using the Ti/α-PbO2/β-PbO2 electrode was 100% after 180 min of electrolysis under optimal conditions, which were selected based on the orthogonal test method, i.e., initial concentration of 2-cholorophenol = 50 mg/L, concentration of Na2SO4 = 0.1 mol/L, temperature = 35°C, and anode current density = 20 mA/cm2. Kinetic analyses demonstrated that the electrochemical oxidation of 2-chlorophenol on the Ti/α-PbO2/β-PbO2 electrode followed pseudo-first order kinetics.

Key role of the phosphate buffer in the H2O2 oxidation of aromatic pollutants catalyzed by iron tetrasulfophthalocyanine

Sanchez, Muriel,Hadasch, Anke,Fell, Rainer T.,Meunier, Bernard

, p. 177 - 186 (2001)

The non-innocent role of the phosphate buffer has been established in the H2O2 oxidative decomposition of 2,4,6-trichlorophenol (TCP), a benchmark pollutant, catalyzed by iron(III) tetrasulfophthalocyanine (FePcS). The catalytic oxidation of several other substrates (3,5-dichloroaniline, tetrachlorocatechol, di-tert-butylcatechol and catechol itself) has been carried out, also demonstrating a crucial influence of the phosphate buffer in the decomposition of the chlorinated substrates. Three hypotheses have been studied: modification of the ionic strength, formation of a peroxyphosphate species, or catalysis by a peroxyphosphate-FePcS complex. Supports for the latter proposal have been obtained from several experimental results and attempts have been made to characterize this putative catalytic intermediate. This intermediate derivative has also been generated from the reaction of FePcS with peroxymonophosphoric acid (PMPA) and its catalytic activity has been checked on the decomposition of TCP in different reaction mixture. A short mechanistic study has allowed different reaction pathways to be proposed, dependent on the active species implicated.

Catalyst for catalytic oxidation of furfural to prepare maleic acid and application thereof

-

Page/Page column 10-12, (2022/02/10)

A catalyst for catalytic oxidation of furfural to prepare maleic acid, relating to the technical field of renewable energy. The catalyst is a mixture of a bromide and a base. A method for preparing the catalyst in catalytic oxidation of furfural to prepare maleic acid. The method includes: mixing the furfural, the bromide-base, an oxidant and a solvent to carry out a reaction to obtain the maleic acid. The present invention has the advantages that the method has a relatively high conversion rate of furfural and a relatively high yield of maleic acid, the conversion rate of furfural is up to 99%, the yield of maleic acid is up to 68.04%; and the catalyst has a high catalytic selectivity and reusability.

Electrochemical Strategy for the Simultaneous Production of Cyclohexanone and Benzoquinone by the Reaction of Phenol and Water

Wu, Ruizhi,Meng, Qinglei,Yan, Jiang,Liu, Huizhen,Zhu, Qinggong,Zheng, Lirong,Zhang, Jing,Han, Buxing

, p. 1556 - 1571 (2022/02/01)

Cyclohexanone and benzoquinone are important chemicals in chemical and manufacturing industries. The simultaneous production of cyclohexanone and benzoquinone by the reaction of phenol and water is an ideal route for the economical production of the two c

Biosynthesis ofl-alanine fromcis-butenedioic anhydride catalyzed by a triple-enzyme cascadeviaa genetically modified strain

Cui, Ruizhi,Liu, Zhongmei,Yu, Puyi,Zhou, Li,Zhou, Zhemin

, p. 7290 - 7298 (2021/09/28)

In industry,l-alanine is biosynthesized using fermentation methods or catalyzed froml-aspartic acid by aspartate β-decarboxylase (ASD). In this study, a triple-enzyme system was developed to biosynthesizel-alanine fromcis-butenedioic anhydride, which was cost-efficient and could overcome the shortcomings of fermentation. Maleic acid formed bycis-butenedioic anhydride dissolving in water was transformed tol-alanineviafumaric acid andl-asparagic acid catalyzed by maleate isomerase (MaiA), aspartase (AspA) and ASD, respectively. The enzymatic properties of ASD from different origins were investigated and compared, as ASD was the key enzyme of the triple-enzyme cascade. Based on cofactor dependence and cooperation with the other two enzymes, a suitable ASD was chosen. Two of the three enzymes, MaiA and ASD, were recombinant enzymes cloned into a dual-promoter plasmid for overexpression; another enzyme, AspA, was the genomic enzyme of the host cell, in which AspA was enhanced by a T7promoter. Two fumarases in the host cell genome were deleted to improve the utilization of the intermediate fumaric acid. The conversion of whole-cell catalysis achieved 94.9% in 6 h, and the productivity given in our system was 28.2 g (L h)?1, which was higher than the productivity that had been reported. A catalysis-extraction circulation process for the synthesis ofl-alanine was established based on high-density fermentation, and the wastewater generated by this process was less than 34% of that by the fermentation process. Our results not only established a new green manufacturing process forl-alanine production fromcis-butenedioic anhydride but also provided a promising strategy that could consider both catalytic ability and cell growth burden for multi-enzyme cascade catalysis.

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