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96-48-0

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96-48-0 Usage

Chemical properties

Gamma-Butyrolactone (GBL) is a colorless oily liquid. It is miscible with water and the general organic and slightly soluble in aliphatic hydrocarbons. GBL has been characterized as having an intense bitter taste with faint to pleasant odor.

Uses

Different sources of media describe the Uses of 96-48-0 differently. You can refer to the following data:
1. Gamma-Butyrolactone (GBL) has widespread industrial use. It is a common solvent found in paint strippers, nail polish removers, stain removers and circuit board cleaners. It is also a common intermediate in industrial chemistry including the manufacture of pyrrolidones and in some pharmaceuticals. Gamma-Butyrolactone is an important organic synthesis intermediate which can be used to synthesize indole butyric acid, butyric acid, succinic acid, α-pyrrolidone, N-methylpyrrolidone, vinyl pyrrolidone, acetyl-γ-butyrolactone, cyclopropylamine, ciprofloxacin, vitamin B1, chlorophyll and so on; It is a non-toxic high boiling point solvent with high solubility and safe and convenient usage and management; It is used as an extractant for butadiene, aromatic, advanced grease petroleum processing; It is used as an acrylonitrile fiber spinning solvent in the chemical fiber industry. It is a thinner and curing agent commonly used in wool, nylon, acrylonitrile and other fiber dyeing auxiliaries and other chemical industries.
2. For the introduction of 3-carboxypropyl side chain. Used as a component of electrolyte solutions in batteries and capacitors.
3. r-butyrolactone is one kind of important fine chemicalintermediate, simultaneously also is one kind of performance fine highboiling point solvent, ideal antioxidant, plasticizer,extracting agent, absorbent, dispersing agent, solid stain, Coagulation Reagent.
4. Intermediate in the synthesis of polyvinylpyrrolidone, DL-methionine, piperidine, phenylbutyric acid, thiobutyric acids. Solvent for polyacrylonitrile, cellulose acetate, methyl methacrylate polymers, polystyrene. Constituent of paint removers, textile aids, drilling oils.

Production

Maleic anhydride hydrogenation method is an advanced technology developed in 1970s. It can produce tetrahydrofuran and γ-butyrolactone in any proportion with a hydrogenation reaction, and the usual ratio is tetrachlorofuran: γ-butyrolactone = 3-4:1. There are many production enterprises, but usually in small scale. The average level is 300t/a. The production capacity account for 30% of the total domestic production capacity.? 2.1, 4-butanediol dehydrogenation reactor is a tube array reactor, filled with flake copper catalyst (with zinc oxide as the carrier). The reaction temperature is controlled at 230-240 ° C. The yield of the product is obtained by reduced pressure distillation of and the yield is above 77%.

Category

Flammable substance

Toxicity grading

Middle

Acute toxicity

oral-rat LD50: 1540 mg/kg; oral-mouse LD50: 1720 mg/kg

Hazardous characteristics of the explosive

Explosible when react with butanol, 2,4-dichlorophenol and sodium hydroxide

Flammability hazard

Flammable in case of heat, open flame; being able to react with oxidant; releasing toxic pungent smoke when in the process of pyrolysis.

Storage and transportation properties

Make sure ventilating, low temperature and drying in the warehouse; separate from the oxidant; prevent fires.

Extinguishing agent

Dry powder, carbon dioxide, foam

Description

Dihydro-2(3H)-furanone. An endogenous neuroregulator made from gamma-amino butyrate and the precursor of gamma hydroxybutyrate. It causes selective increase of brain dopamine by inhibiting its release from nerve terminals. The compound has sedative properties at low doses and produces surgical anesthesia at high doses. It is also used as an industrial solvent and precursor.

Chemical Properties

γ-Butyrolactone is oily, colorless, clear liquid. It has a faint, sweet, aromatic, slightly buttery odor. γ-Butyrolactone is a lactone. It is hydrolyzed under basic conditions, for example in a sodium hydroxide solution into sodium gamma-hydroxybutyrate, the sodium salt of gamma-hydroxybutyric acid. Under acidic conditions it forms an equilibrium mixture of both compounds. These compounds then may go on to form a polymer.

Occurrence

Reported found as a constituent in coffee aroma; a volatile flavor component in roasted filberts as well. Also reported found in tomato, potato, soybeans, beans, vinegar, mushrooms, roasted chicken, beef, cider, beer, wine, scallops and clams.

Definition

ChEBI: A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.

Preparation

γ-Butyrolactone is produced by gas phase 1,4-butanediol under the action of Cu catalyst to produce product γ-butyrolactone and by-product hydrogen. Crude γ-Butyrolactone is purified to remove light and heavy components, with a purity of more than 99.5%, as an export product. At the same time, the by-product hydrogen is sent to other hydrogenation processes for recycling after removing CO and CO2 through the methanation process.

Aroma threshold values

Detection: 20 to 50 ppm

Taste threshold values

Taste characteristic at 75 ppm: milky, creamy with fruity peach-like afternotes.

General Description

Clear colorless oily liquid with a pleasant odor.

Reactivity Profile

gamma-Butyrolactone can react with oxidizing materials, inorganic acids and bases, alcohols and amines. Rapidly hydrolyzed by bases and slowly hydrolyzed by acids. gamma-Butyrolactone is volatile with steam. . The combination of the lactone, butanol, 2,4-dichlorophenol, and sodium hydroxide in the attempted synthesis of 2,4-dichlorophenoxybutyric acid caused a thermal runaway reaction that eventually exploded, [CISHC Chem. Safety Summ., 1977, 48, 3].

Fire Hazard

gamma-Butyrolactone is combustible.

Biochem/physiol Actions

Precursor of γ-hydroxybutyric acid (GHB). It blocks dopamine release by blocking impulse flow in dopaminergic neurons. Pretreatment with γ-butyrolactone allows detection of autoreceptor-induced dopamine release.

Safety Profile

Moderately toxic by ingestion, intravenous, and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data by skin contact. Mutation data reported. Less acutely toxic than ppropiolactone. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, alcohol foam, CO2, dry chemical. Potentially explosive reaction with butanol + 2,4 dichlorophenol + sodium hydroxide. When heated to decomposition it emits acrid and irritating fumes.

Potential Exposure

Used as a chemical intermediate for making other chemicals, including pesticides, cosmetics, and pharmaceuticals; as a solvent for paint, nail polish removers, and industrial chemicals. Used in electronics, drilling and petroleum industries as a stabilizer and solvent. Used as a flavoring agent in various foods and beverages, including grains and breakfast foods, candy, and alcoholic and nonalcoholic drinks. Drug of abuse: the United States Food and Drug Administration has warned the public not to purchase or consume products, containing gamma-butyrolactone (GBL). FDA has also asked the companies that manufacture these products to voluntarily recall them. The agency has received reports of serious health problems—some that are potentially life-threatening—associated with the use of these products. Although labeled as dietary supplements and marketed under various brand names, these products are illegally marketed unapproved new drugs. False advertising claims include building muscles, improved physical performance, enhanced sex, reduced stress and induced sleep

Shipping

Listed by some sources as unregulated. UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1—Poisonous materials, Technical Name Required.

Purification Methods

Dry the lactone over anhydrous CaSO4, then fractionally distil it. Handle it in a fume cupboard due to its TOXICITY. [Beilstein 17 V 7.]

Incompatibilities

4-Butyrolactone is incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, alcohols, amines, strong and inorganic acids, strong bases. Rapidly hydrolyzed by bases and slowly hydrolyzed by acids. It is hygroscopic and volatile with steam. Combustible; vapor may form explosive mixture with air.

Waste Disposal

Use a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. It is inappropriate and possibly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator. All federal, state, and local environmental regulations must be observed.

Check Digit Verification of cas no

The CAS Registry Mumber 96-48-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 6 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 96-48:
(4*9)+(3*6)+(2*4)+(1*8)=70
70 % 10 = 0
So 96-48-0 is a valid CAS Registry Number.
InChI:InChI=1/C4H8O4/c1-2(5)3(6)4(7)8/h2-3,5-6H,1H3,(H,7,8)

96-48-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name γ-butyrolactone

1.2 Other means of identification

Product number -
Other names γ-Butyrolactone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:96-48-0 SDS

96-48-0Synthetic route

1,4-butenediol
6117-80-2

1,4-butenediol

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With 5 wt% Pd nanoparticles loaded on phosphate anion exchanged [Mg6Al2(OH)16]CO3*xH2O; air at 50℃; under 760.051 Torr; for 6h; Reagent/catalyst; Irradiation;100%
With acetone; dihydridotetrakis(triphenylphosphine)ruthenium In toluene at 180℃; for 3h;88 % Chromat.
5-ketohexanoic acid
3128-06-1

5-ketohexanoic acid

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With 5% active carbon-supported ruthenium; isopropyl alcohol at 160℃; for 0.416667h; Reagent/catalyst; Temperature; Microwave irradiation;100%
With hydrogen In 1,4-dioxane at 180℃; under 37503.8 Torr; for 3h; Reagent/catalyst; Solvent; Autoclave;
furfural
98-01-1

furfural

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

Butane-1,4-diol

A

2-methylfuran
534-22-5

2-methylfuran

B

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With hydrogen; Cu-based catalyst at 210℃; Product distribution; Further Variations:; Temperatures; reaction in vapour phase, fixed bed reactor, coupled dehydrogenation reactions of title comp. and INO 160;A 96.5%
B 99.4%
cyclobutanone
1191-95-3

cyclobutanone

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With oxone; silica gel In dichloromethane at 20℃; for 1h; Baeyer-Villiger oxidation;99%
With acyltransferase from Mycobacterium smegmatis; dihydrogen peroxide; ethyl acetate In water at 35℃; for 2h; Baeyer-Villiger Ketone Oxidation; Enzymatic reaction;99%
With 2,2,2-trifluoroethanol; dihydrogen peroxide for 24h; Ambient temperature;98%
methyl 4-hydroxybutanoate
925-57-5

methyl 4-hydroxybutanoate

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With C16H25N3O2S In n-heptane for 3h; Reflux; Molecular sieve; Inert atmosphere;99%
With C16H25N3O2S In n-heptane for 48h; Reflux; Molecular sieve;99%
In hexane at 26℃; porcine pancreatic lipase (PPL);
With porcine pancreatic lipase (E.(1)C313) In diethyl ether at 26℃; Yield given;
2-buten-4-olide
497-23-4

2-buten-4-olide

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With hydrogen In methanol under 26252.6 Torr; for 2h; Reagent/catalyst; Autoclave;99%
With 0.5% palladium on silica gel; hydrogen In methanol at 80℃; under 26252.6 Torr; Catalytic behavior; Kinetics; Reagent/catalyst; Autoclave;92.6%
With Ni#NiO; hydrogen In ethanol at 80℃; under 22502.3 Torr; for 1h; Reagent/catalyst; Autoclave;86.6%
maleic acid
110-16-7

maleic acid

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

4-butanolide
96-48-0

4-butanolide

C

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

Butane-1,4-diol

D

succinic acid
110-15-6

succinic acid

E

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With hydrogen; 0.5 percent Pd on Rutile TiO2 at 110℃; Product distribution / selectivity;A 0.37%
B 0.28%
C 0.37%
D 98.89%
E 0.08%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

A

4-butanolide
96-48-0

4-butanolide

B

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; Cu-based catalyst at 190℃; Product distribution; Further Variations:; Temperatures; reaction in vapour phase, fixed bed reactor;A 98.8%
B 0.8%
maleic acid
110-16-7

maleic acid

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

4-butanolide
96-48-0

4-butanolide

C

methanol
67-56-1

methanol

D

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

Butane-1,4-diol

E

malic acid
617-48-1

malic acid

F

succinic acid
110-15-6

succinic acid

G

acetic acid
64-19-7

acetic acid

H

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; 0.5percent Pd on Rutile TiO2 at 110℃; Product distribution / selectivity;A 0.45%
B 0.06%
C 0%
D 0.21%
E 0.36%
F 98.73%
G 0.04%
H 0.08%
maleic acid
110-16-7

maleic acid

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

4-butanolide
96-48-0

4-butanolide

C

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

Butane-1,4-diol

D

4-hydroxybutanoic acid
591-81-1

4-hydroxybutanoic acid

E

succinic acid
110-15-6

succinic acid

F

acetic acid
64-19-7

acetic acid

G

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; 0.5percent Pd on Rutile TiO2 at 110℃; Product distribution / selectivity;A 0.77%
B 0.38%
C 0.24%
D 0.05%
E 98.28%
F 0.02%
G 0.26%
tetrahydrofuran
109-99-9

tetrahydrofuran

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With trans-{dioxoruthenium(VI)(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)propylenediamine)}(perchlorate)2 In acetonitrile at 25℃; for 1h;98%
Stage #1: tetrahydrofuran With bromine In dichloromethane; water for 1h; Reflux;
Stage #2: With dihydrogen peroxide In dichloromethane; water for 1h; Reflux;
98%
With manganese (VII)-oxide In tetrachloromethane; acetone at -45℃;86%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With phosphoric acid tributyl ester at 119.84℃; under 9375.94 Torr; for 8h; Catalytic behavior; Reagent/catalyst; Autoclave;98%
With Cu-Al hydrotalcite In 1,4-dioxane at 220℃; under 12001.2 Torr; for 0.045h;98%
With Hoveyda-Grubbs catalyst second generation; potassium hydroxide; tricyclohexylphosphine In toluene at 110℃; for 24h; Reagent/catalyst; Schlenk technique; Inert atmosphere;98%
dimethyl cis-but-2-ene-1,4-dioate
624-48-6

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

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

2-methoxytetrahydrofuran
13436-45-8

2-methoxytetrahydrofuran

C

4-butanolide
96-48-0

4-butanolide

D

propan-1-ol
71-23-8

propan-1-ol

E

2-(4'-hydroxybutoxy)-tetrahydrofuran
64001-06-5

2-(4'-hydroxybutoxy)-tetrahydrofuran

F

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

Butane-1,4-diol

G

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; copper catalyst, T 4489, Sud-Chemie AG, Munich at 150 - 280℃; under 187519 Torr; Neat liquid(s) and gas(es)/vapour(s);A 1%
B n/a
C 0.4%
D n/a
E n/a
F 98%
G 0.5%
5-Chloro-dihydro-2(3H)-furanone
36603-83-5

5-Chloro-dihydro-2(3H)-furanone

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With palladium on activated carbon; hydrogen at 200℃; under 760.051 Torr; for 149h; Temperature; Reagent/catalyst;97.98%
4-(tert-butyldimethylsilyl)but-3-yn-1-ol
160194-31-0

4-(tert-butyldimethylsilyl)but-3-yn-1-ol

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With 8-isopropyl-quinoline-N-oxide; [Au(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(NTf2)] In fluorobenzene; 1,2-dichloro-ethane at 60℃; for 5h;96%
maleic anhydride
108-31-6

maleic anhydride

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With hydrogen In 1,4-dioxane at 159.84℃; under 37503.8 Torr; Reagent/catalyst; Autoclave;95.94%
at 275℃; under 51485.6 Torr; Hydrogenation.an einen Nickel-Chrom-Molybdaen-Katalysator;
With cobalt at 200℃; under 102971 Torr; Hydrogenation;
α-bromo-γ-butyrolactone
5061-21-2

α-bromo-γ-butyrolactone

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With DMBI In tetrahydrofuran for 4h; Heating;95%
With nickel In tetrahydrofuran at 20℃; for 0.75h;95%
With triethyl borane; tri-n-butyl-tin hydride In hexane; toluene at -78℃; for 0.5h;90%
succinic acid
110-15-6

succinic acid

A

4-butanolide
96-48-0

4-butanolide

B

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

Butane-1,4-diol

Conditions
ConditionsYield
With C36H54IrN2P2(1+)*C24H20B(1-); hydrogen; sodium hydride In toluene at 180℃; under 7500.75 - 45004.5 Torr; for 18h; Reagent/catalyst; Temperature; Pressure; Autoclave; Sealed tube;A 5%
B 95%
Stage #1: succinic acid In 1,4-dioxane at 500℃; for 4h;
Stage #2: With hydrogen In 1,4-dioxane at 200℃; under 60006 Torr; for 5h; Catalytic behavior; Reagent/catalyst;
A n/a
B 64.7%
With hydrogen In water at 130℃; under 37503.8 Torr; for 12h; Pressure; Reagent/catalyst; Temperature; Autoclave;A 34%
B 23%
4-Aminobutanol
13325-10-5

4-Aminobutanol

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor In water for 15h; pH=5.5; Enzymatic reaction; chemoselective reaction;95%
4-hydroxybutanoic acid hydrazide
3879-08-1

4-hydroxybutanoic acid hydrazide

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With benzeneseleninic acid In dichloromethane for 1.75h;91%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

A

(Z)-6-hydroxy-hex-2-enoic acid ethyl ester
1092929-40-2

(Z)-6-hydroxy-hex-2-enoic acid ethyl ester

B

4-butanolide
96-48-0

4-butanolide

C

octa-2,6-dienedioic acid diethyl ester
15898-58-5

octa-2,6-dienedioic acid diethyl ester

D

(E)-6-hydroxy-hex-2-enoic acid ethyl ester
13038-15-8

(E)-6-hydroxy-hex-2-enoic acid ethyl ester

Conditions
ConditionsYield
With manganese(IV) oxide In dichloromethane at 20℃; for 48h; Wittig olefination;A 5%
B n/a
C n/a
D 91%
maleic acid
110-16-7

maleic acid

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

4-butanolide
96-48-0

4-butanolide

C

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

Butane-1,4-diol

D

4-hydroxybutanoic acid
591-81-1

4-hydroxybutanoic acid

E

malic acid
617-48-1

malic acid

F

succinic acid
110-15-6

succinic acid

G

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With hydrogen; 0.5percent Pd/2.0percent Re on Rutile TiO2 at 110℃; Product distribution / selectivity;A 1.27%
B 4.78%
C 1.55%
D 1.24%
E 0.48%
F 90.6%
G 0.08%
succinic acid anhydride
108-30-5

succinic acid anhydride

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With hydrogen In 1,4-dioxane at 199.84℃; under 37503.8 Torr; for 5h; Catalytic behavior; Activation energy; Temperature;90.1%
With lithium borohydride In tetrahydrofuran for 0.25h;68%
With lithium borohydride In tetrahydrofuran at 25℃; for 0.25h; Mechanism; other cyclic anhydrides;68%
4-hydroxybutanoic acid
591-81-1

4-hydroxybutanoic acid

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With sulfuric acid In chloroform at 60℃; for 1h; pH=0.5; pH-value; Solvent; Temperature;90%
bei der Destillation;
With hydrogenchloride In ethanol at 25℃; Rate constant;
With cis-nitrous acid at 25℃; Rate constant;
With hydrogenchloride at 35℃; Equilibrium constant; Further Variations:; Temperatures;
succinic acid
110-15-6

succinic acid

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With 5% active carbon-supported ruthenium; hydrogen at 150℃; under 26252.6 Torr;90%
With butanediamide; hydrogen In Triethylene glycol dimethyl ether at 205℃; under 6750.68 Torr; for 2h; Reagent/catalyst; Autoclave;30%
With D-glucose; hydrogen In Triethylene glycol dimethyl ether at 205℃; under 6750.68 Torr; for 2h; Autoclave;27.5%
4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With [RuCl2(PPh3)2(2-PyCH21,3,5-triaza-7-phosphadamantane)].Br; potassium hydroxide In water for 48h; Reagent/catalyst; Schlenk technique; Reflux; Inert atmosphere; Green chemistry;90%
With potassium hydroxide; tricyclohexylphosphine In toluene at 110℃; for 24h; Schlenk technique;
maleic anhydride
108-31-6

maleic anhydride

A

4-butanolide
96-48-0

4-butanolide

B

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen In 1,4-dioxane at 159.84℃; under 37503.8 Torr; Reagent/catalyst; Autoclave;A 89.9%
B 6.83%
4-hydroxy-1-butanitrile
628-22-8

4-hydroxy-1-butanitrile

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With ; water In 1,2-dimethoxyethane at 140℃; for 24h;89%
succinic acid
110-15-6

succinic acid

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

4-butanolide
96-48-0

4-butanolide

C

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

Butane-1,4-diol

D

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen In 1,4-dioxane at 139.84℃; under 60006 Torr; for 96h; Catalytic behavior; Reagent/catalyst; Time; Temperature; Autoclave; Overall yield = 100 %;A 0.2%
B 3.1%
C 89%
D 7.6%
With hydrogen; 1.0percent Pd/ 3.0percent Re on Rutile TiO2 at 164 - 185℃; for 21 - 237h; Product distribution / selectivity;A 2.95%
B 0%
C 81.5%
D 3.35%
With hydrogen; 0percent Pd/5.0percent Re on Rutile TiO2 at 170 - 185℃; for 90 - 825h; Product distribution / selectivity;A 3.38%
B 0%
C 64.14%
D 2.86%
4-{[(1Z,3E)-2-(2-furylcarbonyl)-5-oxo-1,5-diphenylpenta-1,3-dienyl]amino}butanoic acid

4-{[(1Z,3E)-2-(2-furylcarbonyl)-5-oxo-1,5-diphenylpenta-1,3-dienyl]amino}butanoic acid

A

4-butanolide
96-48-0

4-butanolide

B

3-(2-furylcarbonyl)-2,6-diphenylpyridine

3-(2-furylcarbonyl)-2,6-diphenylpyridine

Conditions
ConditionsYield
In ethanol at 78℃; for 4h;A n/a
B 89%
4-butanolide
96-48-0

4-butanolide

benzylamine
100-46-9

benzylamine

N-benzyl-4-hydroxybutanamide
19340-88-6

N-benzyl-4-hydroxybutanamide

Conditions
ConditionsYield
With bis(trifluoromethane)sulfonimide lithium In chloroform at 85℃; for 40h;100%
Stage #1: benzylamine With diisobutylaluminium hydride In tetrahydrofuran; toluene
Stage #2: 4-butanolide In tetrahydrofuran at 20℃; for 0.5h;
98%
In benzene for 12h; Reflux;98%
pyrrolidine
123-75-1

pyrrolidine

4-butanolide
96-48-0

4-butanolide

4-hydroxy-1-(pyrrolidin-1-yl)butan-1-one
73200-24-5

4-hydroxy-1-(pyrrolidin-1-yl)butan-1-one

Conditions
ConditionsYield
With triethylamine Inert atmosphere; Reflux;100%
With triethylamine for 16h; Reflux;94%
In benzene for 3h; Heating;90%
piperidine
110-89-4

piperidine

4-butanolide
96-48-0

4-butanolide

4-hydroxy-1-(piperidin-1-yl)butan-1-one
86452-60-0

4-hydroxy-1-(piperidin-1-yl)butan-1-one

Conditions
ConditionsYield
With bis(trifluoromethane)sulfonimide lithium In chloroform at 85℃; for 40h;100%
In acetonitrile at 30℃; under 6750540 Torr; for 96h;99%
In acetonitrile at 30℃; under 6750540 Torr; for 168h;99%
4-butanolide
96-48-0

4-butanolide

(2S,5S)-2,5-dimethylpyrrolidine
117968-50-0

(2S,5S)-2,5-dimethylpyrrolidine

(2S,5S)-1-(4-hydroxybutanoyl)-2,5-dimethylpyrrolidine
139108-39-7

(2S,5S)-1-(4-hydroxybutanoyl)-2,5-dimethylpyrrolidine

Conditions
ConditionsYield
With triethylamine for 12h; Heating;100%
With triethylamine for 48h; Heating;96%
4-butanolide
96-48-0

4-butanolide

diethylamine
109-89-7

diethylamine

N,N-Diethyl-4-hydroxy-butyramide
86452-59-7

N,N-Diethyl-4-hydroxy-butyramide

Conditions
ConditionsYield
In acetonitrile at 30℃; under 6750540 Torr; for 96h;100%
Stage #1: diethylamine With diisobutylaluminium hydride In tetrahydrofuran; toluene
Stage #2: 4-butanolide In tetrahydrofuran at 45℃; for 2h;
72%
4-butanolide
96-48-0

4-butanolide

formic acid ethyl ester
109-94-4

formic acid ethyl ester

sodium salt of (Z)-3-(hydroxymethylene)dihydro-2(3H)-furanone
51270-64-5, 54211-97-1, 93698-26-1

sodium salt of (Z)-3-(hydroxymethylene)dihydro-2(3H)-furanone

Conditions
ConditionsYield
With sodium hydride100%
With sodium In diethyl ether at -20 - -15℃; for 5h;
4-butanolide
96-48-0

4-butanolide

formic acid ethyl ester
109-94-4

formic acid ethyl ester

sodium salt of (E)-3-(hydroxymethylene)dihydro-2(3H)-furanone
54211-97-1

sodium salt of (E)-3-(hydroxymethylene)dihydro-2(3H)-furanone

Conditions
ConditionsYield
With sodium hydride100%
With ethanol; sodium hydride In 1,2-dimethoxyethane at 40℃; for 22h; cross-Claisen acylation;97%
With sodium methylate In diethyl ether for 12h;69%
With sodium hydroxide In 1,2-dimethoxyethane at 60℃; for 16h;66%
4-butanolide
96-48-0

4-butanolide

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

Butane-1,4-diol

Conditions
ConditionsYield
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.0833333h;100%
With C31H33ClN2O3RuS; potassium tert-butylate; hydrogen In isopropyl alcohol at 60℃; under 37503.8 Torr; for 48h; Inert atmosphere;100%
With C39H39N6ORu(1+)*Br(1-); potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 37503.8 Torr; for 16h; Reagent/catalyst;100%
4-butanolide
96-48-0

4-butanolide

4-iodobutanoate de trimethylsilyle
67764-03-8

4-iodobutanoate de trimethylsilyle

Conditions
ConditionsYield
With trimethylsilyl iodide; iodine In chloroform-d1 for 1h; Ambient temperature;100%
4-butanolide
96-48-0

4-butanolide

sodium 4-hydroxybutanoate
502-85-2

sodium 4-hydroxybutanoate

Conditions
ConditionsYield
With water; sodium hydroxide at 20℃; Inert atmosphere;100%
With ethanol; sodium hydroxide at 20℃; for 2h;95%
With sodium hydroxide at 45 - 60℃; for 12h;95%
4-butanolide
96-48-0

4-butanolide

iodosilyl 4-iodobutyrate
127421-48-1

iodosilyl 4-iodobutyrate

Conditions
ConditionsYield
With diiodosilane; iodine In chloroform-d1 at 50℃; for 0.166667h;100%
4-butanolide
96-48-0

4-butanolide

ethylamine
75-04-7

ethylamine

N-ethyl-4-hydroxybutanamide
42042-64-8

N-ethyl-4-hydroxybutanamide

Conditions
ConditionsYield
In tetrahydrofuran at 50℃; for 22h;100%
In tetrahydrofuran at 20℃; Acylation;
With ammonia In methanol at 20℃;
4-butanolide
96-48-0

4-butanolide

4-Aminobutanol
13325-10-5

4-Aminobutanol

4-hydroxy-N-(4-hydroxybutyl)butanamide

4-hydroxy-N-(4-hydroxybutyl)butanamide

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene Reflux;100%
In various solvent(s) for 18h; Heating;
4-butanolide
96-48-0

4-butanolide

Lithium γ-hydroxybutyrate
63255-29-8

Lithium γ-hydroxybutyrate

Conditions
ConditionsYield
With lithium hydroxide monohydrate In methanol; water at 20℃; for 16h;100%
With lithium hydroxide In methanol; water at 20℃; for 16h;100%
With lithium hydroxide; water In methanol at 20℃;
4-butanolide
96-48-0

4-butanolide

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

1,1-diphenylbutan-1,4-diol
1023-94-5

1,1-diphenylbutan-1,4-diol

Conditions
ConditionsYield
With hydrogenchloride; ammonium chloride In tetrahydrofuran100%
Stage #1: 4-butanolide; phenylmagnesium bromide In tetrahydrofuran; diethyl ether at -78 - 20℃; Inert atmosphere;
Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether at 10℃; Cooling with ice;
In tetrahydrofuran Grignard reaction; Reflux;
4-butanolide
96-48-0

4-butanolide

3-bromoaniline
591-19-5

3-bromoaniline

1-(3-bromophenyl)-2-pyrrolidinone
38348-83-3

1-(3-bromophenyl)-2-pyrrolidinone

Conditions
ConditionsYield
With hydrogenchloride In water at 160℃; for 36h;100%
4-butanolide
96-48-0

4-butanolide

3-methoxybenzenethiol
15570-12-4

3-methoxybenzenethiol

4-((3-methoxyphenyl)thio)butanoic acid sodium salt

4-((3-methoxyphenyl)thio)butanoic acid sodium salt

Conditions
ConditionsYield
With ethanol; sodium for 24h; Inert atmosphere; Reflux;100%
With sodium In ethanol for 24h; Inert atmosphere; Reflux;100%
4-butanolide
96-48-0

4-butanolide

methylamine
74-89-5

methylamine

1-methyl-pyrrolidin-2-one
872-50-4

1-methyl-pyrrolidin-2-one

Conditions
ConditionsYield
With water; ZSM-5 at 280℃;99%
In water at 300℃; under 75007.5 Torr; Concentration;99.9%
at 255℃; under 15001.5 Torr; for 3h;98.2%
4-butanolide
96-48-0

4-butanolide

methylamine
74-89-5

methylamine

γ-hydroxybutyric acid monomethylamide
37941-69-8

γ-hydroxybutyric acid monomethylamide

Conditions
ConditionsYield
at 20℃; for 1.5h;99%
99.5%
With water at 0 - 5℃; for 2h;95.5%
4-butanolide
96-48-0

4-butanolide

dimethyl amine
124-40-3

dimethyl amine

γ-hydroxybutyric acid monomethylamide
37941-69-8

γ-hydroxybutyric acid monomethylamide

Conditions
ConditionsYield
99.5%
4-butanolide
96-48-0

4-butanolide

N-butylamine
109-73-9

N-butylamine

N-butyl-4-hydroxybutyramide
42042-67-1

N-butyl-4-hydroxybutyramide

Conditions
ConditionsYield
With bis(trifluoromethane)sulfonimide lithium In chloroform at 85℃; for 40h;99%
4-butanolide
96-48-0

4-butanolide

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

oxo-(2-oxotetrahydrofuran-3-yl)acetic acid ethyl ester
42564-36-3

oxo-(2-oxotetrahydrofuran-3-yl)acetic acid ethyl ester

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 0 - 20℃; for 6.25h;99%
With sodium ethanolate In ethanol at 0 - 20℃;96%
With sodium methylate72%
4-butanolide
96-48-0

4-butanolide

benzylamine
100-46-9

benzylamine

1-benzyl-2-pyrrolidone
5291-77-0

1-benzyl-2-pyrrolidone

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium Tetrafluoroborate In 1,4-dioxane at 220℃; for 0.583333h; Microwave irradiation;99%
for 24h; Heating;79%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate In toluene at 110℃; for 36h; Reagent/catalyst; Inert atmosphere; Glovebox; Molecular sieve; Schlenk technique;65%
4-butanolide
96-48-0

4-butanolide

1-iodoheptadecafluorooctane
507-63-1

1-iodoheptadecafluorooctane

2-Heptadecafluorooctyl-tetrahydro-furan-2-ol
112678-33-8

2-Heptadecafluorooctyl-tetrahydro-furan-2-ol

Conditions
ConditionsYield
With methyllithium; lithium bromide In diethyl ether at -78℃; for 1h;99%
With methyllithium In diethyl ether at -78℃; for 1h;99%
4-butanolide
96-48-0

4-butanolide

1-amino-2-propene
107-11-9

1-amino-2-propene

N-allyl 4-hydroxybutyramide
98435-58-6

N-allyl 4-hydroxybutyramide

Conditions
ConditionsYield
at 120 - 130℃; for 3h;99%
at 120 - 130℃; for 3h;99%
With bis(trifluoromethane)sulfonimide lithium In chloroform at 85℃; for 40h;99%
In benzene for 12h; Inert atmosphere; Reflux;

96-48-0Relevant articles and documents

Production of γ-butyrolactone from biomass-derived 1,4-butanediol over novel copper-silica nanocomposite

Hwang, Dong Won,Kashinathan, Palraj,Lee, Jong Min,Lee, Jeong Ho,Lee, U-Hwang,Hwang, Jin-Soo,Hwang, Young Kyu,Chang, Jong-San

, p. 1672 - 1675 (2011)

γ-Butyrolactone was produced highly selectively from biomass-derived 1,4-butanediol by vapor-phase dehydrocyclization over novel copper-silica nanocomposite catalyst. Compared with usual Cu(12)/SiO2, the highly Cu-loaded SiO2 nanocomposite (80 wt%) exhibited high catalyst performance with 98% yield on 400 h stream without significant deactivation even in the absence of H2.

Synthesis and metal binding properties of N-alkylcarboxyspiropyrans

Perry, Alexis,Kousseff, Christina J.

, p. 1542 - 1550 (2017)

Spiropyrans bearing an N-alkylcarboxylate tether are a common structure in dynamic, photoactive materials and serve as colourimetric/fluorimetric cation receptors. In this study, we describe an efficient synthesis of spiropyrans with 2–12 carbon atom alkylcarboxylate substituents, and a systematic analysis of their interactions with metal cations using 1H NMR and UV-visible spectroscopy. All N-alkylcarboxyspiropyrans in this study displayed a strong preference for binding divalent metal cations and a modest increase in M2+ binding affinity correlated with increased alkycarboxylate tether length.

-

Nikishin et al.

, (1973)

-

-

Nikishin et al.

, (1971)

-

Convergent Cascade Catalyzed by Monooxygenase–Alcohol Dehydrogenase Fusion Applied in Organic Media

Huang, Lei,Aalbers, Friso S.,Tang, Wei,R?llig, Robert,Fraaije, Marco W.,Kara, Selin

, p. 1653 - 1658 (2019)

With the aim of applying redox-neutral cascade reactions in organic media, fusions of a type II flavin-containing monooxygenase (FMO-E) and horse liver alcohol dehydrogenase (HLADH) were designed. The enzyme orientation and expression vector were found to influence the overall fusion enzyme activity. The resulting bifunctional enzyme retained the catalytic properties of both individual enzymes. The lyophilized cell-free extract containing the bifunctional enzyme was applied for the convergent cascade reaction consisting of cyclobutanone and butane-1,4-diol in different microaqueous media with only 5 % (v/v) aqueous buffer without any addition of external cofactor. Methyl tert-butyl ether and cyclopentyl methyl ether were found to be the best organic media for the synthesis of γ-butyrolactone, resulting in about 27 % analytical yield.

REARRANGEMENT OF 2-BUTYNE-1,4-DIOL TO BUTYROLACTONE CATALYZED BY RUTHENIUM COMPLEXES

Shvo, Youval,Blum, Yigal,Reshep, Deborah

, p. C79 - C81 (1982)

The isomerization of 2-butyne-1,4-diol to butyrolactone catalysed by ruthenium complexes is described.

Au/TiO2 as high efficient catalyst for the selective oxidative cyclization of 1,4-butanediol to γ-butyrolactone

Huang, Jie,Dai, Wei-Lin,Li, Hexing,Fan, Kangnian

, p. 69 - 76 (2007)

Au/TiO2 catalysts prepared by the deposition-precipitation method showed excellent activity and selectivity in the oxidative cyclization of 1,4-butanediol to γ-butyrolactone, with high yields (>99%) under mild conditions (413 K, 1.25 MPa air). Catalysts with 3-8% gold loading and calcined at 573-673 K were all highly active for the formation of γ-butyrolactone, as demonstrated by XRD, TEM, XPS, ICP and UV-vis DRS results. It is concluded that highly dispersed small (2-10 nm) gold particles are formed with the surface enrichment of gold. The ratio of cationic gold to metallic gold depends on the treatment temperature. These findings, combined with those of the activity tests, lead to the conclusion that the surface metallic nanosized gold particles are active sites. The catalyst can be reused with no drop in activity or selectivity.

Gas-phase hydrogenation of maleic anhydride to γ-butyrolactone over Cu-CeO2-Al2O3 catalyst at atmospheric pressure: Effects of the residual sodium and water in the catalyst precursor

Yu, Yang,Zhan, Wangcheng,Guo, Yun,Lu, Guanzhong,Adjimi, Souheila,Guo, Yanglong

, p. 392 - 397 (2014)

Cu-CeO2-Al2O3 catalysts were prepared by the co-precipitation method with different washing operations during the preparation process for the purpose of controlling the contents of the residual sodium and water in the catalyst precursors. Cu-CeO2-Al2O3 catalysts were characterized by ICP-AES, XRD, SEM, nitrogen sorption, N2O chemisorption, Raman spectroscopy and H2-TPR. Effects of the residual sodium and water in the catalyst precursor on the catalytic performance of Cu-CeO2-Al2O3 catalyst for gas-phase hydrogenation of maleic anhydride to γ-butyrolactone at atmospheric pressure, and the structure-activity relationships were investigated. The results show that the residual water and sodium in the form of Na2CO3 in the catalyst precursor lead to a decrease in Cu dispersion and Cu surface area, which is disadvantageous to the catalytic performance and stability. Washing step of the residual sodium in the catalyst precursor with the deionized water and then removing step of the residual water using azeotropy distillation shows a great improvement in the stability of Cu-CeO2-Al2O3 catalyst, in which 100% of conversion of maleic anhydride and 100% of selectivity to γ-butyrolactone were maintained for 12 h.

CATALYTIC ENANTIOTOPOS DIFFERENTIATING DEHYDROGENATION OF PROCHIRAL DIOLS USING RUTHENIUM COMPLEX WITH DIOP

Ishii, Youichi,Osakada, Kohtaro,Ikariya, Takao,Saburi, Masahiko,Yoshikawa, Sadao

, p. 1179 - 1182 (1982)

Optically active δ- and γ-lactones are obtained by the homogeneous catalytic dehydrogenation of prochiral diols using Ru2Cl4((-)-DIOP)3 in the presence of benzalacetone as a hydrogen acceptor and triethylamine.

Oxidative heterocyclization of 1,4-butanediol to 4-butanolide

Seleznev,Zorina,Trifonova,Zorin,Rakhmankulov

, p. 1064 - 1065 (2002)

-

Hydrolysis of Spiro Derivatives that Undergo No Shrinkage on Polymerization

Tagoshi, Hirotaka,Endo, Takeshi

, p. 945 - 947 (1989)

Acid catalysed hydrolyses of spiroorthoeters (1, 2a, 2b, and 2c and spirocarbonates (3 and 4) were carried out to give the corresponding ring-opening reaction products.The ring-cleavage modes of these spiro derivatives depended on the structure of intermediate cations.

A novel route for synthesis of γ-butyrolactone through the coupling of hydrogenation and dehydrogenation

Zhu, Yu-Lei,Xiang, Hong-Wei,Wu, Gui-Sheng,Bai, Liang,Li, Yong-Wang

, p. 254 - 255 (2002)

A coupling process of the hydrogenation of maleic anhydride and the dehydrogenation of 1,4-butanediol has been invented for the synthesis of γ-butyrolactone over a Cu-Zn catalyst, realizing optimal hydrogen utilization and better energy efficiency.

OXIDATION OF CYCLOBUTANONES TO γ-BUTYROLACTONES WITH HYDROGEN PEROXIDE IN 2,2,2-TRIFLUOROETHANOL

Matsumoto, Masakatsu,Kobayashi, Hisako

, p. 2443 - 2447 (1986)

Cyclobutanones were selectively oxidized to yield γ-butyrolactones with hydrogen peroxide in 2,2,2-trifluoroethanol.

Routes to Heterotrinuclear Metal Siloxide Complexes for Cooperative Activation of O2

Braun-Cula, Beatrice,Herwig, Christian,Hoof, Santina,Limberg, Christian,Wind, Marie-Louise

, (2020)

The assembly of heterometallic complexes capable of activating dioxygen is synthetically challenging. Here, we report two different approaches for the preparation of heterometallic superoxide complexes [PhL2CrIII-η1-O2][MX]2 (PhL = -OPh2SiOSiPh2O-, MX+ = [CoCl]+, [ZnBr]+, [ZnCl]+) starting from the CrII precursor complex [PhL2CrII]Li2(THF)4. The first strategy proceeds via the exchange of Li+ by [MX]+ through the addition of MX2 to [PhL2CrII]Li2(THF)4 before the reaction with dioxygen, whereas in the second approach a salt metathesis reaction is undertaken after O2 activation by adding MX2 to [PhL2CrIII-η1-O2]Li2(THF)4. The first strategy is not applicable in the case of redox-active metal ions, such as Fe2+ or Co2+, as it leads to the oxidation of the central chromium ion, as exemplified with the isolation of [PhL2CrIIICl][CoCl]2(THF)3. However, it provided access to the hetero-bimetallic complexes [PhL2CrIII-η1-O2][MX]2 ([MX]+ = [ZnBr]+, [ZnCl]+) with redox-inactive flanking metals incorporated. The second strategy can be applied not only for redox-inactive but also for redox-active metal ions and led to the formation of chromium(III) superoxide complexes [PhL2CrIII-η1-O2][MX]2 (MX+ = [ZnCl]+, [ZnBr]+, [CoCl]+). The results of stability and reactivity studies (employing TEMPO-H and phenols as substrates) as well as a comparison with the alkali metal series (M+ = Li+, Na+, K+) confirmed that although the stability is dependent on the Lewis acidity of the counterions M and the number of solvent molecules coordinated to those, the reactivity is strongly dependent on the accessibility of the superoxide moiety. Consequently, replacement of Li+ by XZn+ in the superoxides leads to more stable complexes, which at the same time behave more reactive toward O-H groups. Hence, the approaches presented here broaden the scope of accessible heterometallic O2 activating compounds and provide the basis for further tuning of the reactivity of [RL2CrIII-η1-O2]M2 complexes.

Ru/SiO2 Catalyst for Highly Selective Hydrogenation of Dimethyl Malate to 1,2,4-Butanetriol at Low Temperatures in Aqueous Solvent

Chen, Can,Jiang, Junxiang,Li, Guangci,Li, Xuebing,Wang, Da,Wang, Zhong,Yu, Pei

, (2022/01/12)

Catalytic selective hydrogenation of esterified malic acid to produce 1,2,4-butanetriol (1,2,4-BT) using H2 as the reducing reagent suffers from the low 1,2,4-BT selectivity. Here, Ru/SiO2 catalyst was employed for selective hydrogenation of dimethyl malate (DM) to produce 1,2,4-BT, which gave abnormal high DM conversion (100%) and 1,2,4-BT selectivity (92.4%) in aqueous solvent at 363?K, especially, the 1,2,4-BT yield even is higher than the optimal catalyst reported (Ru-Re, 79.8%). The reaction pathways for the DM hydrogenation on Ru/SiO2 were also proposed, suggesting that extremely high 1,2,4-BT selectivity require for the much high hydrogenation rates at low temperatures, where side-reaction transesterification rates are relatively low. The extremely high hydrogenation activity and 1,2,4-BT selectivity on Ru/SiO2 in aqueous solvent at low temperatures arise from that H2O may coordinate to Ru2+ and prevent the reduction of Ru2+ to Ru under high H2 pressure. Ru/SiO2 surface presents abundant Ru2+ in aqueous solvent, can activate H2 through heterolytic cleavage mode to form hydride, which can significantly increase hydrogenation rates of C = O groups at low temperatures. In addition, the activity and 1,2,4-BT selectivity on Ru/SiO2 catalyst only reduced by 2.3% and 2.6%, respectively over a period of 550?h. Graphical Abstract: [Figure not available: see fulltext.]

Catalytic behaviour of the Cu(I)/L/TEMPO system for aerobic oxidation of alcohols - a kinetic and predictive model

Abu-Radaha, Batool,Al-Hunaiti, Afnan,Repo, Timo,Wraith, Darren

, p. 7864 - 7871 (2022/04/09)

Here, we disclose a new copper(i)-Schiff base complex series for selective oxidation of primary alcohols to aldehydes under benign conditions. The catalytic protocol involves 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO), N-methylimidazole (NMI), ambient air, acetonitrile, and room temperature. This system provides a straightforward and rapid pathway to a series of Schiff bases, particularly, the copper(i) complexes bearing the substituted (furan-2-yl)imine bases N-(4-fluorophenyl)-1-(furan-2-yl)methanimine (L2) and N-(2-fluoro-4-nitrophenyl)-1-(furan-2-yl)methanimine (L4) have shown excellent yields. Both benzylic and aliphatic alcohols were converted to aldehydes selectively with 99% yield (in 1-2 h) and 96% yield (in 16 h). The mechanistic studies via kinetic analysis of all components demonstrate that the ligand type plays a key role in reaction rate. The basicity of the ligand increases the electron density of the metal center, which leads to higher oxidation reactivity. The Hammett plot shows that the key step does not involve H-abstraction. Additionally, a generalized additive model (GAM, including random effect) showed that it was possible to correlate reaction composition with catalytic activity, ligand structure, and substrate behavior. This can be developed in the form of a predictive model bearing in mind numerous reactions to be performed or in order to produce a massive data-set of this type of oxidation reaction. The predictive model will act as a useful tool towards understanding the key steps in catalytic oxidation through dimensional optimization while reducing the screening of statistically poor active catalysis.