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110-94-1

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110-94-1 Usage

Description

Glutaric acid, an alpha,omega-dicarboxylic acid, is a linear five-carbon dicarboxylic acid that appears as colorless crystals or a white solid. It is soluble in water, alcohol, ether, and chloroform, and slightly soluble in petroleum ether. Glutaric acid has a role as a human metabolite and a Daphnia magna metabolite, and it is found in washings from fleece and in the juice of unripened sugar beet.

Uses

Used in Organic Synthesis:
Glutaric acid is used as a raw material for organic synthesis, serving as a precursor in the production of various compounds.
Used in Pharmaceutical Industry:
Glutaric acid is used as a pharmaceutical intermediate, contributing to the development of new drugs and medications.
Used in Synthetic Resin Industry:
Glutaric acid is utilized in the production of synthetic resins, which are essential in the manufacturing of plastics and other materials.
Used in Polyester Polyols Production:
Glutaric acid acts as a precursor in the production of polyester polyols, which are important components in the creation of polyurethane plastics and elastomers.
Used in Polyamides Synthesis:
Glutaric acid is used in the synthesis of polyamides, which are essential materials in the textile and automotive industries.
Used in Ester Plasticizers Production:
Glutaric acid serves as a starting material for the production of ester plasticizers, which are additives that increase the flexibility and workability of plastics.
Used in Corrosion Inhibitors:
Glutaric acid is used in the formulation of corrosion inhibitors, which protect metals from degradation and corrosion.
Used in Surfactants Synthesis:
Glutaric acid is employed in the synthesis of surfactants, which are compounds that reduce the surface tension of liquids and are used in various industries, including cosmetics and cleaning products.
Used in Metal Finishing Compounds:
Glutaric acid is used in the production of metal finishing compounds, which are essential for improving the appearance and durability of metal surfaces.
Used in Decreasing Polymer Elasticity:
Glutaric acid is useful in decreasing the elasticity of polymers, which can be beneficial in specific applications where a more rigid material is desired.
Used in Catabolism of Lysine in Mammals:
Glutaric acid acts as an intermediate during the catabolism of lysine, an essential amino acid, in mammals.
Used in Environmentally Friendly Solvents:
Glutaric acid is converted into dibasic esters and sold as environmentally friendly solvents, which are used in various industries due to their reduced environmental impact.

Preparation

glutaric acid is produced as a by-product of the production process of adipic acid (about 2% of the output of an adipic acid plant is glutaric); Glutaric acid can be produced through various chemical routes, for example, from cyclopentane by oxidation with molecular oxygen and cobalt (III) catalysts or by ozonolysis; and from cyclopentanol–cyclopentanone by oxidation with oxygen and Co(CH3CO2)2, with potassium peroxide in benzene, or with N2O4 or nitric acid. Together with succinic acid, glutaric acid is formed as a by-product during oxidation of cyclohexanol–cyclohexanone in the adipic acid production process.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 2489, 1956 DOI: 10.1021/ja01592a042Organic Syntheses, Coll. Vol. 1, p. 290, 1941Synthetic Communications, 10, p. 205, 1980 DOI: 10.1080/00397918008064223

Air & Water Reactions

Water soluble.

Reactivity Profile

1,5-Pentanedioic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in 1,5-Pentanedioic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions 1,5-Pentanedioic acid reacts with bases, oxidizing agents and reducing agents.

Fire Hazard

Flash point data for 1,5-Pentanedioic acid are not available; however, 1,5-Pentanedioic acid is probably combustible.

Flammability and Explosibility

Notclassified

Purification Methods

Crystallise the acid from *benzene, CHCl3, distilled water or *benzene containing 10% (w/w) of diethyl ether. Dry it under vacuum. [Beilstein 2 IV 1934.]

Check Digit Verification of cas no

The CAS Registry Mumber 110-94-1 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, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 110-94:
(5*1)+(4*1)+(3*0)+(2*9)+(1*4)=31
31 % 10 = 1
So 110-94-1 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9)/p-2

110-94-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A14595)  Glutaric acid, 99%   

  • 110-94-1

  • 25g

  • 223.0CNY

  • Detail
  • Alfa Aesar

  • (A14595)  Glutaric acid, 99%   

  • 110-94-1

  • 100g

  • 484.0CNY

  • Detail
  • Alfa Aesar

  • (A14595)  Glutaric acid, 99%   

  • 110-94-1

  • 500g

  • 1463.0CNY

  • Detail
  • Sigma-Aldrich

  • (89147)  Glutaricacid  certified reference material, TraceCERT®

  • 110-94-1

  • 89147-100MG

  • 1,117.35CNY

  • Detail

110-94-1SDS

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 glutaric acid

1.2 Other means of identification

Product number -
Other names 1,5-Pentanedioic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:110-94-1 SDS

110-94-1Synthetic route

(+-)-1-(trimethylsilyl)ethanol
13246-39-4

(+-)-1-(trimethylsilyl)ethanol

5,5'-oxybis(5-oxopentanoic acid)
53715-97-2

5,5'-oxybis(5-oxopentanoic acid)

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane100%
1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With C24H33IrN4O3; water; sodium hydroxide for 18h; Catalytic behavior; Reagent/catalyst; Reflux;98%
In water for 48h; Ambient temperature; Gluconobacter roseus IAM 1841;97%
With sodium hydroxide In water at 20℃; Temperature; Concentration; Electrochemical reaction;91%
cis-1,2-cyclopentanediol
5057-98-7

cis-1,2-cyclopentanediol

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With dihydrogen peroxide; Na12[WZn3(H2O)2(ZnW9O34)2] at 75℃; for 7h;98%
cyclohexane-1,2-dione
765-87-7

cyclohexane-1,2-dione

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With ozone In tetrachloromethane; water at 20℃; for 1h; UV-irradiation;97%
With water; ozone at 25℃; under 760.051 Torr; for 1h; Irradiation;95%
With oxygen; sodium hydroxide In water at 90℃; under 3000.3 Torr; for 3h; pH=7;21%
trans-cyclopentane-1,2-diol
5057-99-8

trans-cyclopentane-1,2-diol

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium tungstate; phosphoric acid; dihydrogen peroxide at 90℃; for 5h;96%
Cyclopentanol
96-41-3

Cyclopentanol

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
Stage #1: Cyclopentanol With Oxone; ruthenium(III) chloride monohydrate In water at 70℃; for 8h;
Stage #2: In ethanol Cooling;
95%
With nitric acid at 70 - 100℃;
With nitric acid; vanadia at 70 - 100℃;
cyclopentanone
120-92-3

cyclopentanone

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With oxygen; trifluoroacetic acid; sodium nitrite at 0 - 20℃; for 5.25h; Product distribution / selectivity;95%
Stage #1: cyclopentanone With Oxone; ruthenium(III) chloride monohydrate In water at 20℃; for 5h;
Stage #2: In ethanol Cooling;
90%
With oxygen; copper dichloride In acetic acid at 80℃; for 6h; Oxidation;84%
cyclopentene
142-29-0

cyclopentene

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With potassium metaperiodate; potassium aquapentachlororuthenate(III) In dichloromethane; water; acetonitrile at 20℃; for 2h; Catalytic behavior; Sonication;94%
With potassium permanganate; H-montmorillonite In water; benzene at 25 - 30℃; for 1h;90%
With periodic acid; cis-[RuCl2(bipy)2]*2H2O In tetrachloromethane; water; acetonitrile at 20℃; for 2h;85%
1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With triethylmethylammonium iodide; water; dihydrogen peroxide In acetonitrile at 55℃; for 23h;94%
With potassium carbonate In water at 25℃; Electrochemical reaction;81%
With iodine; oxygen In ethyl acetate for 10h; Mercury lamp irradiation;40%
cyclohexenone
930-68-7

cyclohexenone

oxone

oxone

Os(VIII)

Os(VIII)

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium sulfate; OsO4 In ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol92%
Glutaraldehyde
111-30-8

Glutaraldehyde

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide In water at 70℃; for 3.5h; Green chemistry;91%
With tert.-butylhydroperoxide; copper(l) chloride In acetonitrile at 20℃; for 3.5h;78%
With bis(acetylacetonate)oxovanadium; dihydrogen peroxide In acetonitrile at 60℃; for 8h; Reagent/catalyst; Time;42%
Glutaraminsaeureethylester
56703-79-8

Glutaraminsaeureethylester

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With titanium tetrachloride In 1,4-dioxane; water for 20h; Heating;90%
Dimethyl glutarate
1119-40-0

Dimethyl glutarate

A

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

B

Pentanedioic acid, monomethyl ester
1501-27-5

Pentanedioic acid, monomethyl ester

Conditions
ConditionsYield
Stage #1: Dimethyl glutarate With potassium hydroxide In tetrahydrofuran; water at 0℃; for 0.166667h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0℃;
A 13.2%
B 86.8%
Stage #1: Dimethyl glutarate With lithium hydroxide; water In tetrahydrofuran at 0℃; for 0.333333 - 0.583333h;
Stage #2: With water Product distribution / selectivity; Acidic conditions;
Stage #1: Dimethyl glutarate With potassium hydroxide; water In tetrahydrofuran at 0℃; for 0.166667 - 0.416667h;
Stage #2: With water Product distribution / selectivity; Acidic conditions;
Stage #1: Dimethyl glutarate With cesium hydroxide; water In tetrahydrofuran at 0℃; for 0.166667 - 0.416667h;
Stage #2: With water Product distribution / selectivity; Acidic conditions;
Stage #1: Dimethyl glutarate With sodium hydroxide; water In tetrahydrofuran at 0℃; for 0.333333 - 0.583333h;
Stage #2: With water Product distribution / selectivity; Acidic conditions;
4-(1,1-dimethylethyl)-cyclohexanol
98-52-2

4-(1,1-dimethylethyl)-cyclohexanol

A

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

B

Adipic acid
124-04-9

Adipic acid

C

succinic acid
110-15-6

succinic acid

D

2-tert-butyl-1,4-butanedicarboxylic acid
10347-88-3

2-tert-butyl-1,4-butanedicarboxylic acid

Conditions
ConditionsYield
With ammonium vanadate; nitric acid at 95 - 100℃; for 1h;A n/a
B n/a
C n/a
D 85%
Cyclopentanol
96-41-3

Cyclopentanol

A

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

B

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With oxygen; trifluoroacetic acid; sodium nitrite at 0 - 20℃; for 12.25h; Product distribution / selectivity;A 85%
B 10%
N,N,N',N'-tetraethyl glutaramide
17642-87-4

N,N,N',N'-tetraethyl glutaramide

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
Stage #1: N,N,N',N'-tetraethyl glutaramide With sodium hydroxide In water at 110℃; for 12h;
Stage #2: With hydrogenchloride; magnesium oxide In water; ethyl acetate pH=Ca. 4;
Stage #3: With sulfuric acid In water; ethyl acetate pH=Ca. 4;
85%
L-glutamic acid
56-86-0

L-glutamic acid

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With sulfuric acid; hypophosphorous acid; sodium nitrite In water at -5 - 0℃; for 10 - 12h; Reagent/catalyst;80%
cyclohexene
110-83-8

cyclohexene

A

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

B

Adipic acid
124-04-9

Adipic acid

C

hexanedial
1072-21-5

hexanedial

D

succinic acid
110-15-6

succinic acid

E

1-cyclopentene-1-carboxaldehyde
6140-65-4

1-cyclopentene-1-carboxaldehyde

F

1,2-Cyclohexanediol
931-17-9

1,2-Cyclohexanediol

G

cyclohexanone-2-ol
533-60-8

cyclohexanone-2-ol

Conditions
ConditionsYield
With dihydrogen peroxide; ortho-tungstic acid In water at 140℃; for 0.333333h; Mechanism; Flow reactor; Microwave irradiation; Sealed tube; Green chemistry; chemoselective reaction;A n/a
B 74%
C n/a
D n/a
E n/a
F n/a
G n/a
cyclohexanone-2-ol
533-60-8

cyclohexanone-2-ol

A

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

B

Adipic acid
124-04-9

Adipic acid

Conditions
ConditionsYield
With oxygen; sodium hydroxide In water at 90℃; for 3h; pH=> 13;A 7%
B 73%
With oxygen; H5PV2Mo10O40(1,11) In acetic acid at 60℃; under 750.06 Torr; for 10h; Yield given. Yields of byproduct given;
With oxygen; H7*10H2O In acetic acid at 60℃; under 750.06 Torr; for 10h; Yield given. Yields of byproduct given;
carbon monoxide
201230-82-2

carbon monoxide

allyl alcohol
107-18-6

allyl alcohol

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With HeMaRaphos; water; toluene-4-sulfonic acid; palladium dichloride In tetrahydrofuran at 125℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; regioselective reaction;73%
1-(trimethylsilyloxy)cyclopentene
19980-43-9

1-(trimethylsilyloxy)cyclopentene

A

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

B

2-hydroxycyclopentanone
99440-98-9

2-hydroxycyclopentanone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; titanium silicate for 24h; Heating;A 72%
B 6%
Glutaronitrile
544-13-8

Glutaronitrile

A

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

B

4-cyanobutyric acid
39201-33-7

4-cyanobutyric acid

Conditions
ConditionsYield
With water; nitrile hydratase SP361 at 30℃; for 40h; in potassium phosphate buffer (pH = 7);A 9%
B 70%
With water Product distribution; bacterial hydrolysis of aliphatic dinitriles with cells of Rhodococcus rhodochrous NCIB 11,216; 0.25 M phosphate buffer, pH 7;
TETRAHYDROPYRANE
142-68-7

TETRAHYDROPYRANE

A

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

B

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With sodium bromate; potassium hydrogensulfate In water at 25 - 30℃; for 20h; Oxidation;A 69%
B 16%
With 2,6-dichloropyridine N-oxide; dichloro(5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)ruthenium(IV) In 1,2-dichloro-ethane at 40℃; for 20h; Reagent/catalyst; Inert atmosphere;A 56%
B 16%
TETRAHYDROPYRANE
142-68-7

TETRAHYDROPYRANE

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With ruthenium tetroxide In tetrachloromethane; water for 95h;68%
With lithium nitrate In water; acetonitrile at 25℃; anodic oxidation;66%
With hydrogenchloride
With nitric acid at 25 - 35℃;
2-acetylcyclopentanaone
1670-46-8

2-acetylcyclopentanaone

A

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

B

2-methylhexane-1,6-dioic acid
626-70-0

2-methylhexane-1,6-dioic acid

C

2-acetyl-2-hydroxycyclopentanone
1262892-77-2

2-acetyl-2-hydroxycyclopentanone

Conditions
ConditionsYield
With dihydrogen peroxide In acetic acid at 20℃; for 240h;A 67%
B 30%
C 0.5%
cyclohexane
110-82-7

cyclohexane

A

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

B

Adipic acid
124-04-9

Adipic acid

Conditions
ConditionsYield
With N-hydroxyphthalimide; nitric acid; trifluoroacetic acid at 20℃; under 760.051 Torr; for 18h; Catalytic behavior; Reagent/catalyst;A 5 %Spectr.
B 66%
With N-hydroxyphthalimide; bis(acetylacetonato)manganese(II); oxygen; acetic acid; cobalt acetylacetonate at 80℃; under 760.051 Torr; for 24h;
Multi-step reaction with 2 steps
1: N-hydroxyphthalimide; oxygen; acetic acid; bis(acetylacetonato)manganese(II) / 6 h / 100 °C / 760.05 Torr
2: oxygen; acetic acid; bis(acetylacetonato)manganese(II) / 6 h / 100 °C / 760.05 Torr
View Scheme
cyclohexanol
108-93-0

cyclohexanol

A

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

B

Adipic acid
124-04-9

Adipic acid

C

monocyclohexyl adipate
54812-72-5

monocyclohexyl adipate

D

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With oxygen at 120℃; for 4.33333h; Further byproducts given;A 3.1%
B 12.4%
C 8.9%
D 65%
With oxygen at 120℃; for 4.33333h; Further byproducts given;A 3.1%
B 12.4%
C 8.9%
D 65%
cyclohexane
110-82-7

cyclohexane

A

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

B

Adipic acid
124-04-9

Adipic acid

C

succinic acid
110-15-6

succinic acid

D

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With N-hydroxyphthalimide; bis(acetylacetonato)manganese(II); oxygen; acetic acid at 80℃; under 760.051 Torr; for 14h; Time;A 9%
B 65%
C 6%
D 19%
glutaric anhydride,
108-55-4

glutaric anhydride,

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With potassium superoxide; tetraethylammonium bromide In N,N-dimethyl-formamide at 25℃; for 12h; Ring cleavage;64%
Multi-step reaction with 2 steps
1: sodium; alcohol
2: chromic acid
View Scheme
methanol
67-56-1

methanol

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Dimethyl glutarate
1119-40-0

Dimethyl glutarate

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
With phosphorus trichloride Cooling;92%
With hydrogenchloride
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

2-(vinyloxy)ethyl isothiocyanate
59565-09-2

2-(vinyloxy)ethyl isothiocyanate

pentanedioic acid bis-[1-(2-isothiocyanato-ethoxy)-ethyl] ester

pentanedioic acid bis-[1-(2-isothiocyanato-ethoxy)-ethyl] ester

Conditions
ConditionsYield
trifluoroacetic acid at 55 - 60℃;100%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

zinc(II) oxide

zinc(II) oxide

zinc glutarate
331968-18-4

zinc glutarate

Conditions
ConditionsYield
In toluene (Ar) suspn. ZnO and glutaric acid in toiluene was heated at 80°C for 1 day; react. mixt. was cooled, ppt. was filtered, washed with acetone and dried in vacuo at 130°C; powder X-ray diffraction;100%
In ethanol; toluene at 60℃; for 10h; Solvent;97%
In toluene at 60℃;85%
In toluene byproducts: H2O; powdered ZnO added to soln. of org. compd., slurry stirred vigorously at55°C for 2 h then refluxed until no more H2O in trap; cooled to room temp., filtered, washed with acetone, powdered product dried in vac. at 100°C for 5 d; detn. FTIR, XANES EXAFS, (13)C NMR;
In toluene heating (3 h, 45°C); filtration, drying (overnight, vac., 90°C);
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine
151433-25-9

(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine

[(1-RR)-(Glutaric acid)]

[(1-RR)-(Glutaric acid)]

Conditions
ConditionsYield
Stage #1: cobalt(II) acetate; (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine In ethanol for 5h; Heating / reflux;
Stage #2: 1,5-pentanedioic acid With oxygen In dichloromethane; acetone at 20℃; for 3h;
100%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

meloxicam
71125-38-7

meloxicam

meloxicam glutaric acid
1246227-11-1

meloxicam glutaric acid

Conditions
ConditionsYield
In chloroform for 0.5h;100%
In tetrahydrofuran Product distribution / selectivity;
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Dimethyl glutarate
1119-40-0

Dimethyl glutarate

Conditions
ConditionsYield
With triethylamine at 160℃; for 5h; Autoclave; Green chemistry;99%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

2,2'-(1,3-propanediyl)bis(1H-benzimidazole)
7147-66-2

2,2'-(1,3-propanediyl)bis(1H-benzimidazole)

Conditions
ConditionsYield
With tetrafluoroboric acid In water at 150℃; for 2h;98%
With polyphosphoric acid at 120℃;79%
With polyphosphoric acid at 180℃;65%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

4-nitro-2-trifluoromethyl-aniline
121-01-7

4-nitro-2-trifluoromethyl-aniline

1-(4-nitro-2-trifluoromethyl-phenyl)-piperidine-2,6-dione

1-(4-nitro-2-trifluoromethyl-phenyl)-piperidine-2,6-dione

Conditions
ConditionsYield
With PPA at 80℃; for 12h;98%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

2-methyl-4-nitro-benzenamine
99-52-5

2-methyl-4-nitro-benzenamine

1-(2-methyl-4-nitro-phenyl)-piperidine-2,6-dione

1-(2-methyl-4-nitro-phenyl)-piperidine-2,6-dione

Conditions
ConditionsYield
With PPA at 80℃; for 12h;98%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

(3R,4R)-3,4-bis(diphenylphosphanyl)pyrrolidine
99135-90-7

(3R,4R)-3,4-bis(diphenylphosphanyl)pyrrolidine

δ-<(3R,4R)-3,4-Bis(diphenylphophino)pyrrolidino>-δ-oxopentansaeure
104351-44-2

δ-<(3R,4R)-3,4-Bis(diphenylphophino)pyrrolidino>-δ-oxopentansaeure

Conditions
ConditionsYield
In diethyl ether; dichloromethane98%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

camostat
59721-28-7

camostat

N,N-dimethyl-carbamoylmethyl p-(p-guanidinobenzoyloxy)phenylacetate glutarate

N,N-dimethyl-carbamoylmethyl p-(p-guanidinobenzoyloxy)phenylacetate glutarate

Conditions
ConditionsYield
In ethanol at 20 - 65℃;98%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

4,5-dimethyl-1,2-phenylenediamine
3171-45-7

4,5-dimethyl-1,2-phenylenediamine

5,6,5',6'-tetramethyl-2,2'-(1,3-propanediyl) bis-(1H-benzimidazole)
1171054-64-0

5,6,5',6'-tetramethyl-2,2'-(1,3-propanediyl) bis-(1H-benzimidazole)

Conditions
ConditionsYield
With tetrafluoroboric acid In water at 150℃; for 2h;98%
4,4'-bipyridine
553-26-4

4,4'-bipyridine

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

copper nitrate hemi(pentahydrate)

copper nitrate hemi(pentahydrate)

Cu2(glutarate)2(4,4'-bipyridine)

Cu2(glutarate)2(4,4'-bipyridine)

Conditions
ConditionsYield
With sodium hydroxide In water at 70℃; for 1h;98%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

4-nitro-aniline
100-01-6

4-nitro-aniline

1-(4-nitro-phenyl)-piperidine-2,6-dione
139776-02-6

1-(4-nitro-phenyl)-piperidine-2,6-dione

Conditions
ConditionsYield
With PPA at 80℃; for 12h;97%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

2-methoxy-4-nitrophenylamine
97-52-9

2-methoxy-4-nitrophenylamine

1-(2-methoxy-4-nitro-phenyl)-piperidine-2,6-dione

1-(2-methoxy-4-nitro-phenyl)-piperidine-2,6-dione

Conditions
ConditionsYield
With PPA at 80℃; for 12h;97%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

(S)-2,2'-dihydroxy-1,1'-binaphthyl-3-carbaldehyde

(S)-2,2'-dihydroxy-1,1'-binaphthyl-3-carbaldehyde

(C20H11CHO(OH)OCO)2C3H6
1002101-64-5

(C20H11CHO(OH)OCO)2C3H6

Conditions
ConditionsYield
Stage #1: 1,5-pentanedioic acid; (S)-2,2'-dihydroxy-1,1'-binaphthyl-3-carbaldehyde With dmap In dichloromethane at 20℃; for 0.25h;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;
97%
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane for 3h;96%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

N,0-dimethylhydroxylamine
1117-97-1

N,0-dimethylhydroxylamine

N1,N5-dimethoxy-N1,N5-dimethylglutaramide
259236-21-0

N1,N5-dimethoxy-N1,N5-dimethylglutaramide

Conditions
ConditionsYield
Stage #1: 1,5-pentanedioic acid; N,0-dimethylhydroxylamine In toluene at 0℃; for 0.166667h;
Stage #2: With phosphorus trichloride In toluene at 20 - 60℃; for 0.5h;
97%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

metformin hydrochloride
1115-70-4

metformin hydrochloride

metformin glutarate (2:1)

metformin glutarate (2:1)

Conditions
ConditionsYield
Stage #1: metformin hydrochloride With sodium hydroxide In methanol; chloroform; water at 20℃;
Stage #2: 1,5-pentanedioic acid In methanol; chloroform at 20℃; Product distribution / selectivity;
96.9%
Stage #1: metformin hydrochloride With sodium hydroxide In tetrahydrofuran; water at 20℃;
Stage #2: 1,5-pentanedioic acid In tetrahydrofuran; water at 10℃; Product distribution / selectivity;
96.7%
Stage #1: metformin hydrochloride With sodium hydroxide In methanol; chloroform; water at 20℃;
Stage #2: 1,5-pentanedioic acid In methanol; chloroform; water at 20℃; Product distribution / selectivity;
96.9%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

dimethylbiguanide
657-24-9

dimethylbiguanide

metformin glutarate (2:1)

metformin glutarate (2:1)

Conditions
ConditionsYield
Stage #1: dimethylbiguanide In water; acetone at 40℃;
Stage #2: 1,5-pentanedioic acid In water; acetone at 10℃; Product distribution / selectivity;
95.3%
In water; acetone at 10 - 40℃; Product distribution / selectivity;95.3%
In ethanol at 10 - 20℃; Product distribution / selectivity;62.8%
With sodium hydroxide In ethanol at 70℃; Product distribution / selectivity;57.7%
In methanol at 40℃; Product distribution / selectivity;43.8%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

glutaric acid bis-(2-ethyl-hexyl ester)
21302-20-5

glutaric acid bis-(2-ethyl-hexyl ester)

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; for 2h;95%
With Candida antarctica lipase B In cyclohexane at 45℃; for 24h;68%
With sulfuric acid; toluene
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

glutaric anhydride,
108-55-4

glutaric anhydride,

Conditions
ConditionsYield
With Isopropenyl acetate; Montmorillonite KSF for 0.0666667h; Irradiation;95%
With PEG-1000; sulfated zirconia at 40℃; for 1.5h; neat (no solvent);95%
With niobium(V) oxide hydrate In 1,3,5-trimethyl-benzene at 200℃; for 60h; Inert atmosphere; Molecular sieve;92%

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Study on the adsorption behavior of Glutaric acid (cas 110-94-1) modified Pb(II) imprinted chitosan-based composite membrane to Pb(II) in aqueous solution08/23/2019

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The influence of impurities on the solubility and metastable zone width (MSZW) of glutaric acid in acetic acid solution was studied. At T = (300.15–340.15) K, the presence of impurity succinic acid or adipic acid increases the solubility of glutaric acid in acetic acid solution, and the solubil...detailed

110-94-1Relevant articles and documents

Visible photorelease of liquid biopsy markers following microfluidic affinity-enrichment

Brown, Virginia,Digamber, Rane,Givens, Richard S.,Jackson, J. Matt,Pahattuge, Thilanga N.,Perera, Chamani,Peterson, Blake R.,Soper, Steven A.,Wijerathne, Harshani,Witek, Malgorzata A.

, p. 4098 - 4101 (2020)

We detail a heterobifunctional, 7-aminocoumarin photocleavable (PC) linker with unique properties to covalently attach Abs to surfaces and subsequently release them with visible light (400-450 nm). The PC linker allowed rapid (2 min) and efficient (>90%) release of CTCs and EVs without damaging their molecular cargo.

Cason et al.

, p. 289,290,297 (1959)

-

Dox,Yoder

, p. 649 (1922)

-

Tungsten doped mesoporous SBA-16 as novel heterogeneous catalysts for oxidation of cyclopentene to glutaric acid

Jin, Manman,Zhang, Guodi,Guo, Zhenmei,Lv, Zhiguo

, (2018)

Novel heterogeneous tungsten species in mesoporous silica SBA-16 catalysts based on ship-in-a-bottle methodology are originally reported for oxidizing cyclopentene (CPE) to glutaric acid (GAC) using hydrogen peroxide (H2O2). For all W-SBA-16 catalysts, isolated tungsten species and octahedrally coordinated tungsten oxide species are observed while WO3 crystallites are detected for the W-SBA-16 catalysts with Si/ W = 5, 10, and 20. The specific surface areas and the corresponding total pore volumes decrease significantly as increasing amounts of tungsten incorporated into the pores of SBA-16. Using tungsten-substituted mesoporous SBA-16 heterogeneous catalysts, high yield of GAC (55%) is achieved with low tungsten loading (for Si/W = 30, ~13?wt%) for oxidation of CPE. The W-SBA-16 catalysts with Si/W = 30 can be reused five times without dramatic deactivation. In fact, low catalytic activity provided by bulk WO3 implies that the highly distributed tungsten species in SBA-16 and the steric confinement effect of SBA-16 are key elements for the outstanding catalytic performance.

Enantiotopically Selective Oxidation of α,ω-Diols with the Enzyme Systems of Microorganisms

Ohta, Hiromichi,Tetsukawa, Hatsuki,Noto, Naoko

, p. 2400 - 2404 (1982)

Gluconobacter were found to be capable of oxidizing prochiral diols such as 2-substituted propane-1,3-diols 1 and 3-substituted pentane-1,5-diols 4 with distinction of pro-R and pro-S sites of the molecules, in that (-)-(R)-α-substituted β-hydroxypropionic acids 2 and (+)-(3S)-3-substituted δ-valerolactones 5 were obtained, respectively.Oxidation of 3-methylpentane-1,3,5-triol 11 afforded unnatural (+)-(S)-mevalonolactone 12.The steric bulkiness of the substituents on the prochiral center and the distance from the hydroxy group greatly affected the rate and the enantioselectivity of the reaction.

MIL-101 metal-organic framework: A highly efficient heterogeneous catalyst for oxidative cleavage of alkenes with H2O2

Saedi, Zahra,Tangestaninejad, Shahram,Moghadam, Majid,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj

, p. 18 - 22 (2012)

In the present work, a new and efficient method for direct oxidation of alkenes to carboxylic acids with H2O2 catalyzed by metal-organic framework MIL-101 is reported. In this transformation, the MIL-101 catalyzes the oxidation reactions by framework nodes and acts as a heterogeneous and reusable catalyst. The structure of MIL-101 was stable after three catalytic cycles.

Efficient synthesis of glutaric acid from L-glutamic acid via diazoniation/hydrogenation sequence

Zhang, Wei,Rao, Meng-Yun,Cheng, Zhong-Jun,Zhu, Xiao-Yan,Gao, Kai,Yang, Jian,Yang, Bo,Liao, Xia-Li

, p. 716 - 721 (2015)

The practical synthetic preparation of glutaric acid has remained a major challenge to date. In the present study, glutaric acid was synthesised by way of one-pot diazoniation/hydrogenation of the readily available L-glutamic acid under aqueous conditions on a gram-scale with good yields. This is the first example of the deamination of the aliphatic primary amine via diazoniation and could afford a practical approach to the production of glutaric acid.

Oxidation of Cyclopentene by RuCl3-NaOCl Catalyst

Orita, Hideo,Hayakawa, Takashi,Takehira, Katsuomi

, p. 2637 - 2638 (1986)

Oxidation of cyclopentene by RuCl3-NaOCl catalyst in an aqueous-organic two phase system was investigated by changing compositions of solvent system and additives to the aqueous solution.Use of acetonitrile as a cosolvent enhanced the reaction rate greatly, and addition of NaOH improved the yield of glutaric acid up to 80percent.

Novel photochemical reactions of carbocyclic diazodiketones without elimination of nitrogen – a suitable way to N-hydrazonation of C–H-bonds

Rodina, Liudmila L.,Azarova, Xenia V.,Medvedev, Jury J.,Semenok, Dmitrij V.,Nikolaev, Valerij A.

, p. 2250 - 2258 (2018)

The sensitized photoexcitation of 2-diazocyclopentane-1,3-diones in the presence of THF leads to the insertion of the terminal N-atom of the diazo group into the α-С–Н bond of THF, producing the associated N-alkylhydrazones in yields of up to 63–71%. Further irradiation of hydrazones derived from furan-fused tricyclic diazocyclopentanediones culminates in the cycloelimination of furans to yield 2-N-(alkyl)hydrazone of cyclopentene-1,2,3-trione. By contrast, the direct photolysis of carbocyclic diazodiketones gives only Wolff rearrangement products with up to 90–97% yield.

Oxidative cleavage of 1,3-dicarbonyls to carboxylic acids with oxone

Ashford,Grega

, p. 1523 - 1524 (2001)

-

-

Farrar

, p. 1708 (1957)

-

Osmium tetroxide-promoted catalytic oxidative cleavage of olefins: An organometallic ozonolysis

Travis, Benjamin R.,Narayan, Radha S.,Borhan, Babak

, p. 3824 - 3825 (2002)

A mild, organometallic alternative to ozonolysis utilizing oxone and OsO4 is presented. This is a direct oxidation of olefins via the carbon-carbon cleavage of an osmate ester by the action of oxone. Twenty-four different olefins were converted to their corresponding ketones or carboxylic acids in high yields (> 80%). Free alcohols, acetate- and benzyl-protected alcohols, and 1,2-diols were stable under these conditions. This method should be applicable for traditional organic synthesis. Copyright

Alkene and alkyne oxidative cleavage catalyzed by RuO4 in environmentally acceptable solvents

Griffith, William P.,Kwong, Eugene

, p. 2945 - 2951 (2003)

The application of CCl4, C6Hl2, EtOAc, and Me2CO as solvents for biphasic systems has been compared for oxidative cleavage of alkenes and alkynes by RuO4 to carboxylic acids, using the RuCl3·nH2O-IO(OH)5 reagent for which an improved procedure is described. Cyclohexane is an effective and economic replacement for the environmentally unfriendly CCl 4; acetone and ethyl acetate are less effective.

Role of added chloride ions in alteration of reaction pathway in the oxidation of cyclic ketones by dichloroisocyanuric acid - A kinetic study

Lakshman Kumar,Venkata Nadh,Radhakrishnamurti

, p. 376 - 383 (2015)

Effect of added chloride ions on kinetics and pathway of reaction between cyclic ketones (five to eight membered rings) and dichloroisocyanuric acid (DCICA) was studied in aqueous acetic acid - perchloric acid medium. Formation of aliphatic dicarboxylic acids as the end products demonstrates the ring cleavage oxidation. Positive effect of acid and negative effect of dielectric constant on the reaction rate reveals a interaction between positive ion (oxidant in the form of H2OCl+) and dipolar substrate molecule. Zero and first orders by oxidant in absence and presence of added chloride ions illustrates the participation of substrate as enolic form of ketone and protonated ketone, respectively, in the rate determining steps. The observed order of reactivity of cyclic ketones (cyclohexanone > cyclooctanone > cyclopentanone > cycloheptanone) was explained on the bases of ring strain, change of hybridization and conformational considerations. The envisaged plausible mechanism based on order of reactants in presence and absence of added chloride ions was substantiated by the order of Arrhenius parameters.

Effects of counter cations in selective monohydrolyses of symmetric diesters

Niwayama, Satomi,Rimkus, Audrius

, p. 498 - 500 (2005)

Monohydrolyses of symmetric diesters were carried out using several aqueous inorganic bases, LiOH, NaOH, KOH, and CsOH. The more reactive bases showed higher selectivities in the monohydrolyses of acyclic symmetric diesters.

Kinetics of Electron Transfer from Cyclic Ketones to Ni(IV) Periodate Complex in Aqueous Alkaline Medium

Khan, Jaffar Ali,Chandraiah, U.,Kumar, B. Kishore,Kandlikar, Sushama

, p. 1300 - 1303 (1989)

The kinetics of electron transfer from cyclic ketones (represented by (S)) to Ni(IV) periodate complexes has been studied in aqueous alkaline medium.The kinetics exhibit a pseudo-first-order disappearance of Ni(IV) periodate complexes when the is present in excess.The pseudo-first-order rate constants kobs, were linearly dependent on and the order is were found to be unity.The rate of the reaction increased with the increase in ->, however the rates were retarded with the increase in .Salt and solvent effect studies indicate that the reaction is of ion-dipole type.A suitable mechanism involving slow adduct formation between anol and oxidant, and its decomposition in a fast step have been suggested.A rate law consistent with the proposed mechanism has also been derived.The products of oxidation were identified as corresponding decarboxylic acids.

Efficient oxidative cleavage of 1,3-dicarbonyl derivatives with hydrogen peroxide catalyzed by quaternary ammonium iodide

Yuan, Yu,Ji, Xiang,Zhao, Dongbo

, p. 5274 - 5278 (2010)

Quaternary ammonium iodide, a metal-free and mild catalyst, was proven to be a successful catalyst in the oxidative cleavage of 1,3-dicarbonyl derivatives with H2O2 as terminal oxidant. The mechanistic aspects of these "multistep" catalytic oxidations were discussed in terms of the catalytic cycle of the iodine species and the oxidative cleavage of the α carbon from the dicarbonyl compounds to generate the corresponding carboxylic acids.

A Convenient Synthesis of Cyclobutanone

Seetz, J. W. F. L.,Tol, R.,Akkerman, O. S.,Bickelhaupt, F.

, p. 721 (1983)

-

Automated on-line monitoring of the TiO2-based photocatalytic degradation of dimethyl phthalate and diethyl phthalate

Salazar-Beltrán, Daniel,Hinojosa-Reyes, Laura,Maya-Alejandro, Fernando,Turnes-Palomino, Gemma,Palomino-Cabello, Carlos,Hernández-Ramírez, Aracely,Guzmán-Mar, Jorge Luis

, p. 863 - 870 (2019)

A fully automated on-line system for monitoring the TiO2-based photocatalytic degradation of dimethyl phthalate (DMP) and diethyl phthalate (DEP) using sequential injection analysis (SIA) coupled to liquid chromatography (LC) with UV detection was proposed. The effects of the type of catalyst (sol-gel, Degussa P25 and Hombikat), the amount of catalyst (0.5, 1.0 and 1.5 g L-1), and the solution pH (4, 7 and 10) were evaluated through a three-level fractional factorial design (FFD) to verify the influence of the factors on the response variable (degradation efficiency, %). As a result of FFD evaluation, the main factor that influences the process is the type of catalyst. Degradation percentages close to 100% under UV-vis radiation were reached using the two commercial TiO2 materials, which present mixed phases (anatase/rutile), Degussa P25 (82%/18%) and Hombikat (76%/24%). 60% degradation was obtained using the laboratory-made pure anatase crystalline TiO2 phase. The pH and amount of catalyst showed minimum significant effect on the degradation efficiencies of DMP and DEP. Greater degradation efficiency was achieved using Degussa P25 at pH 10 with 1.5 g L-1 catalyst dosage. Under these conditions, complete degradation and 92% mineralization were achieved after 300 min of reaction. Additionally, a drastic decrease in the concentration of BOD5 and COD was observed, which results in significant enhancement of their biodegradability obtaining a BOD5/COD index of 0.66 after the photocatalytic treatment. The main intermediate products found were dimethyl 4-hydroxyphthalate, 4-hydroxy-diethyl phthalate, phthalic acid and phthalic anhydride indicating that the photocatalytic degradation pathway involved the hydrolysis reaction of the aliphatic chain and hydroxylation of the aromatic ring, obtaining products with lower toxicity than the initial molecules.

Palladium Complexes with Bulky Diphosphine Ligands as Highly Selective Catalysts for the Synthesis of (Bio-) Adipic Acid from Pentenoic Acid Mixtures.

Low, Choon Heng,Nobbs, James D.,Van Meurs, Martin,Stubbs, Ludger P.,Drent, Eite,Aitipamula, Srinivasulu,Pung, Michelle H. L.

, p. 4281 - 4292 (2015)

A series of sterically bulky diphosphines have been prepared, including P2 = trans-1,2-bis[(di-tert-butylphosphino)methyl]cyclohexane (4), (2-methylenepropane-1,3-diyl)bis(di-tert-butylphosphine) (5), bis[(di-tert-butylphosphino)methyl]dimethylsilane (6), and cis- and trans-11,12-bis[(di-tert-butylphosphino)methyl]-9,10-dihydro-9,10-ethanoanthracene (10 and 11). The corresponding palladium complexes of these ligands, P2Pd(CF3CO2)2, have been synthesized and characterized. The solid-state structures of [Pd(4)(CF3CO2)2], [Pd(5)(CF3CO2)2], [Pd(6)(CF3CO2)2], and [Pd(11)(CF3CO2)2] were obtained by single-crystal X-ray diffraction and confirm the bidentate binding mode of the ligand and a square-planar coordination geometry with a minor distortion from the ideal. The diphosphines in combination with Pd(OAc)2 have been applied in the hydroxycarbonylation of a mixture of pentenoic acid isomers to produce adipic acid with high selectivity (in several cases >95%). The (regio)selectivity of the hydroxycarbonylation reaction is highly dependent on the P2 diphosphine ligand structure, particularly the steric bulk of the substituents on the diphosphine donor and the P-Pd-P bite angle in the complexes, with respectively tertiary alkyl phosphine substituents (tert-butyl, adamantyl) and a C4 backbone P-Pd-P bite angle >100° being the common features of highly adipic acid selective systems. It is suggested that the regioselectivity of hydroxycarbonylation becomes largely driven by the chelation of the carboxylic acid functionality of pentenoic acid substrates, when smaller size P substituents and/or when P2 ligands with smaller bite angles (100°) are applied.

An efficient method for the catalytic aerobic oxidation of cycloalkanes using 3,4,5,6-Tetrafluoro-N-Hydroxyphthalimide (F4-NHPI)

Guha, Samar K.,Ishii, Yasutaka

, p. 327 - 335 (2021/12/13)

N-Hydroxyphthalimide (NHPI) is known to be an effective catalyst for the oxidation of hydrocarbons. The catalytic activity of NHPI derivatives is generally increased by introducing an electron-withdrawing group on the benzene ring. In a previous report, two NHPI derivatives containing fluorinated alkyl chain were prepared and their catalytic activity was investigated in the oxidation of cycloalkanes. It was found that the fluorinated NHPI derivatives showed better yields for the oxidation reaction. As a continuation of our work with fluorinated NHPI derivatives, our next aim was to investigate the catalytic activity of the NHPI derivatives by introducing fluorine atoms in the benzene ring of NHPI. In the present research, 3,4,5,6-Tetrafluoro-N-Hydroxyphthalimide (F4-NHPI) is prepared and its catalytic activity has been investigated in the oxidation of two different cycloalkanes for the first time. It has been found that F4-NHPI showed higher catalytic efficiency compared with that of the parent NHPI catalyst in the present reactions. The presence of a fluorinated solvent and an additive was also found to accelerate the oxidation.

Visible Light-Driven, Copper-Catalyzed Aerobic Oxidative Cleavage of Cycloalkanones

Xin, Hong,Duan, Xin-Hua,Yang, Mingyu,Zhang, Yiwen,Guo, Li-Na

, p. 8263 - 8273 (2021/06/30)

A visible light-driven, copper-catalyzed aerobic oxidative cleavage of cycloalkanones has been presented. A variety of cycloalkanones with varying ring sizes and various α-substituents reacted well to give the distal keto acids or dicarboxylic acids with moderate to good yields.

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