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120-92-3

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120-92-3 Usage

Physical and Chemical Properties

Cyclopentanone is also known Adipic Ketono. It is transparent colorless oily liquid. It has smell of special ether and also slightly mint-smell. It has a relative molecular mass being 84.12. It also has a relative density being 0.9487, melting point being-51.3 ℃, boiling point being 130.6 ℃, 23~24 ℃ (1.333 X 103Pa), the refractive index being 1.4366, and the flash point being 30 ℃. It is insoluble in water, soluble in alcohol, ether and acetone. It is narcotic at high concentrations. It can be obtained through oxidation of cyclopentanol. It can also be obtained through the heating of Adipic acid in the presence of Barium hydroxide. Cyclopentanone is also easily subject to polymerization especially in the presence of an acid. In the case of heating, it can participate in the following dehydration reactions, respectively producing 2-cyclopentylene cyclopentanone and 2'-cyclopentylene-2-cyclopentylene cyclopentanone: Hydrogenation can produce double-cyclopentanol with further dehydration producing 2, 2-tetramethylene cyclopentanone. Cyclopentanone is mainly used for the manufacturing of drugs, biological agents, pesticides and rubber additives. Aldehydes, ketones can react with diazoalkane and have the nitrogen atoms lost, generating two carbonyl compounds and epoxy compounds. When the aldehydes, ketones molecules contain electron-withdrawing groups, the reactivity is increased will boost the generation of the epoxy compound. The ketone molecule, with the increase of the hydrocarbon group, also mainly generates epoxy compound. Cyclic ketones, instead, will have ring expansion reactions. The bigger the hydrocarbyl group of the diazoalkane is, the more carbonyl compounds can be obtained. The order of the ketone reactivity is consistent with its nucleophilic substitution order: Cl3CCOCH3> ClCH2COCH3> CH3COCH3> CH3COC6H5> cyclohexanone> cyclopentanone> cycloheptanone> cyclooctanone.

The main purpose

1, Take the n-valeraldehyde and cyclopentanone as raw material, and first go through aldol condensation reaction and further dehydration reaction to obtain pentylene cyclopentanone, then followed by selective catalytic hydrogenation to obtain pentyl cyclopentanone. Pentyl cyclopentanone has strong floral and fruity aroma as well as nuances of jasmine. It can be used in the formulation of daily chemical flavor with the usage amount being less than 20%. IFRA has no restrictions. 2, Take n-hexanal and cyclopentanone as the raw material, first have condensation, and then perform selective hydrogenation reaction to obtain hexyl cyclopentanone. Hexyl cyclopentanone has strong jasmine smell accompanied by fruit nuances and can be used in perfume fragrance as well as the formulation of other kinds of fragrance with the usage amount being less than 5%. IFRA has no restrictions. 3, Take the 1-pentene or 1-heptene obtained by the cracking of paraffin or dehydration of the corresponding alcohol as the raw material, in the presence of t-butyl peroxide as the initiator, have addition reaction of the free radical group with cyclopentanone, generating 2-pentyl cyclopentanone (or 2-heptyl-cyclopentanone) with oxidation and ring expansion reaction to become δ-lactone (or δ-Dodecalactone). 4 Synthesis route with cyclopentanone being the starting material is of the greatest industrial production value. Cyclopentanone is first had aldol condensation reaction with n-valeraldehyde with the dehydration products further undergoing condensation and the selective hydrogenation to generate 2-pentyl cyclopentanone. It finally undergoes oxidation and ring expansion to become δ-decalactone. 5, δ-decalactone is mainly used in the formulation of edible food flavor. It is considered with the characteristic flavor of the natural cream. Before its emergence, perfumers had long been limited to application of monomer spices such as butanedione and vanillin monomers to be as the major raw material for the deployment of butter flavor. But it is generally recognized that the formulated butter flavor is worse than natural products in the respects of both taste or flavor respects. Only after the use of δ-decalactone can it have realistic cream flavor, especially in the case of using δ-Dodecalactone and δ-decalactone in combination for being as the main flavor raw material which can further improve the flavor and effect of the formulated cream spice. 6, Take cyclopentanone and pentanal as raw materials, have condensation to produce 2-(1-hydroxy) pentyl cyclopentanone which is then reacted with dimethyl malonate and hydrolyzed at 160~180 ℃, go through decarboxylation, esterification to obtain methyl dihydrojasmonate. Methyl dihydrojasmonate is the edible flavor provided by the GB2760-1996 of China for temporary application. Its aroma is better than the natural methyl jasmonate. Its property is also relatively stable. The above information is edited by the lookchem of Dai Xiongfeng.

Chemical Properties

Different sources of media describe the Chemical Properties of 120-92-3 differently. You can refer to the following data:
1. It is colorless, oily liquid with a pleasant mint smell. It has a melting point of-58.2 ℃, boiling point of 130.6 ℃, the relative density of 0.9509 (20 ℃), the refractive index of 1.4366 and the flash point of 29.82 ℃. It is miscible with ethanol, ethyl ether and slightly soluble in water. It is easy to undergo polymerization, especially in the case of trace amount of acid.
2. colourless liquid
3. Cyclopentanone has an agreeable, peppermint-like odor. It tends to polymerize in the presence of acids.

Production method

It can be obtained through the heating of Adipic acid in the presence of barium hydroxide. Mix the barium hydroxide and adipic acid uniformly and heat to 285-295 °C, further distill out the generated cyclopentanone at this temperature. The distilled calcium chloride is salted out for separating the cyclopentanone; add appropriate amount of alkaline solution to remove the adipic acid wash, then wash with water; dry with anhydrous calcium chloride; have distillation; collect the fraction in the 128-131 ℃ to obtain the finished product with the yield being 75-80%.

Category

Flammable liquid

Toxicity grading

poisoning

Acute toxicity

Intraperitoneal-mouse LD50: 1950 mg/kg; subcutaneous-Mouse LD50: 2600 mg/kg.

Data irritation

Skin-rabbit 500 mg Mild; Eyes-rabbit 100 mg severe.

Flammability and hazard characteristics

It is flammable in case of fire, high temperature and with burning producing irritated smoke.

Storage characteristics

Treasury: ventilation, low-temperature and dry; store it separately from oxidants and acids.

Occurrence

Reported found in roasted onion, baked potato, tomato, gruyere cheese, butter, heated chicken, boiled beef, heated pork, roasted pecan, yellow passion fruit juice.

Uses

Cyclopentanone is used as an intermediate in the synthesis of rubber adhesives, synthetic resins, pharmaceuticals and biologically active compounds. It acts as precursor for the preparation of cyclopentamine and also pentethylcyclanone, cyclopentobarbital. It is a useful laboratory reagent and is used as thinner for epoxies. It can also be used as a solvent in paint and varnish removers and for electronic applications. As a dry cleaning agent, it is used for oil extraction. It is also involved in the preparation of cyclopentanone derivatives like cyclopenylamine and cyclopentanol which find application in the perfume industry.

Preparation

Prepared by heating adipic acid (285 to 295°C) in the presence of barium hydroxide, distilling, ether extraction and then fractionation.

Definition

ChEBI: A cyclic ketone that consists of cyclopentane bearing a single oxo substituent.

Aroma threshold values

Aroma characteristics at 2.0%: musty, slightly toasted bitter almondlike nutty, solventlike with a powdery nuance.

Taste threshold values

Taste characteristics at 20 ppm: musty, toasted nutty with a slight meaty nuance.

General Description

A clear colorless liquid with a petroleum-like odor. Flash point 87°F. Less dense than water and insoluble in water. Vapors heavier than air.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Cyclopentanone polymerizes easily, especially in the presence of acids. Can react with oxidizing materials, i.e. hydrogen peroxide.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Safety Profile

Moderately toxic by intraperitoneal and subcutaneous routes. A skin and severe eye irritant. Dangerous fire hazard when exposed to heat or flame; can react with oxidizers. To fight fire, use alcohol foam, foam, CO2, dry chemical. Potentially explosive reaction with hydrogen peroxide + nitric acid. When heated to decomposition it emits acrid smoke and fumes. See also KETONES.

Purification Methods

Shake it with aqueous KMnO4 to remove materials absorbing around 230 to 240nm. Dry it with Linde-type 13X molecular sieves and fractionally distil it. It has also been purified by conversion to the NaHSO3 adduct which, after crystallising four times from EtOH/water (4:1), is decomposed by adding to an equal weight of Na2CO3 in hot H2O. The free cyclopentanone is steam distilled from the solution. The distillate is saturated with NaCl and extracted with *benzene which is then dried (anhydrous K2CO3) and evaporated. The residue is then distilled [Allen, et al. J Chem Soc 1909 1960]. [Beilstein 7 IV 5.]

Check Digit Verification of cas no

The CAS Registry Mumber 120-92-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 0 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 120-92:
(5*1)+(4*2)+(3*0)+(2*9)+(1*2)=33
33 % 10 = 3
So 120-92-3 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O/c6-5-3-1-2-4-5/h1-4H2

120-92-3 Well-known Company Product Price

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  • Alfa Aesar

  • (A14222)  Cyclopentanone, 99%   

  • 120-92-3

  • 250ml

  • 251.0CNY

  • Detail
  • Alfa Aesar

  • (A14222)  Cyclopentanone, 99%   

  • 120-92-3

  • 500ml

  • 474.0CNY

  • Detail
  • Alfa Aesar

  • (A14222)  Cyclopentanone, 99%   

  • 120-92-3

  • 2500ml

  • 1883.0CNY

  • Detail

120-92-3SDS

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 cyclopentanone

1.2 Other means of identification

Product number -
Other names Adipic keyone

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:120-92-3 SDS

120-92-3Synthetic route

Cyclopentanol
96-41-3

Cyclopentanol

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With water; nickel dibromide; dibenzoyl peroxide In N,N-dimethyl acetamide at 60℃; for 3h;100%
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O) In hexane for 20h; Solvent; Reflux;100%
With allyl methyl carbonate; dihydridotetrakis(triphenylphosphine)ruthenium In toluene at 100℃; for 13h;99%
cyclopentene
142-29-0

cyclopentene

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With oxygen; palladium(II) sulfate; PdSO4-H3PMo6W6O40 In cyclohexane; water at 30℃; for 6h;100%
With oxygen; H3PMo6W6O40 In cyclohexane; water at 29.9℃; under 760 Torr; for 6h;100%
With palladium(II) sulfate; oxygen; H3PMo6W6O40 In cyclohexane; water at 29.9℃; under 760 Torr; for 6h; Product distribution; Rate constant; other time, other Pd(II) salt, other concentration of catalyst;100%
cyclopent-2-enone
930-30-3

cyclopent-2-enone

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With limonene.; palladium on activated charcoal for 0.5h; Heating;100%
With hydrogen; SC-1 Ni2B In methanol at 25℃; under 760 Torr; for 24h;100%
With diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) In chloroform for 0.5h; Ambient temperature;99%
Cyclopentanone oxime
1192-28-5

Cyclopentanone oxime

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With bis(1-CH2Ph-3,5,7-3N-1-N(1+)tricyclo[3.3.1.13,7]decaneS2O8 In acetonitrile for 0.0583333h; Oxidation; Heating;100%
With potassium permanganate In water; acetonitrile at 25℃; for 1h;96%
With dihydrogen peroxide; tripropylammonium fluorochromate (VI) In acetone at 0 - 10℃; for 2.5h;96%
Sodium; 6-cyclopentylideneamino-hexanoate

Sodium; 6-cyclopentylideneamino-hexanoate

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With hydrogenchloride for 0.0416667h; Product distribution; Ambient temperature; pH = 4-6, regeneration of aldehyde;100%
Cyclopentyl bromide
137-43-9

Cyclopentyl bromide

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With oxygen; kieselguhr; copper(l) chloride In hexane for 2.5h; Oxidation; Heating;99%
1,1-Bis(phenylthio)cyclopentane
85895-34-7

1,1-Bis(phenylthio)cyclopentane

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20 - 25℃; for 2h; Irradiation;98%
furfural
98-01-1

furfural

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With hydrogen In water at 160℃; under 30003 Torr; for 7h; Automated synthesizer;98%
With hydrogen In water at 160℃; under 30003 Torr; for 2.5h; Reagent/catalyst; Temperature; Pressure; Autoclave;96%
With hydrogen In water at 150℃; under 30003 Torr; for 6h; Reagent/catalyst; Autoclave;95%
Cyclopentane
287-92-3

Cyclopentane

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With hydrogenchloride; FeH6Mo6O24(3-)*3H3N*3H(1+)*7H2O; tetrabutylammomium bromide; dihydrogen peroxide In 1,4-dioxane; water at 85℃; for 24h;96%
With [Fe4III(μ-O)2(μ-acetate)6(2,2'-bipyridine)2(H2O)2](NO3-)(OH-); dihydrogen peroxide; acetic acid In water; acetonitrile at 32℃; for 3h; Catalytic behavior;60%
With dihydrogen peroxide; vanadium phosphorus oxide In acetonitrile at 50℃; for 20h;48%
nitrocyclopentane
2562-38-1

nitrocyclopentane

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With sodium perborate at 70℃; for 3h; Ionic liquid;95%
With bis-trimethylsilanyl peroxide; sodium hydride In tetrahydrofuran at 20℃; for 24h; Hydrolysis;65%
1-Methanesulfonyl-1-methylsulfanyl-cyclopentane
78795-44-5

1-Methanesulfonyl-1-methylsulfanyl-cyclopentane

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With hydrogenchloride In methanol for 3h; Heating;94%
1-oxa-4-thia-spiro[4.4]nonane
176-38-5

1-oxa-4-thia-spiro[4.4]nonane

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With Glyoxilic acid; Amberlyst 15 for 0.05h; microwave irradiation;94%
With potassium superoxide; tetraethylammonium bromide In N,N-dimethyl-formamide at 20℃; for 3h;88%
Adipic acid
124-04-9

Adipic acid

6-Hydroxyhexanoic acid
1191-25-9

6-Hydroxyhexanoic acid

A

hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

B

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
at 280 - 300℃; Product distribution / selectivity;A 7%
B 94%
sodium phosphate at 290℃; Product distribution / selectivity;A 0.3%
B 77%
tin(IV) oxide at 270℃; Product distribution / selectivity;A 1%
B 73%
sodium hydroxide at 270 - 290℃; Product distribution / selectivity;A 25%
B 58%
sodium borate at 290℃; Product distribution / selectivity;A 0.3%
B 39%
hexanedioic acid dimethyl ester
627-93-0

hexanedioic acid dimethyl ester

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
Al2O3#dotK2O In water at 360℃; under 0.750075 Torr; for 500h;93%
Cyclopentanol
96-41-3

Cyclopentanol

acetic acid
64-19-7

acetic acid

A

cyclopentyl acetate
933-05-1

cyclopentyl acetate

B

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII); sodium bromide for 10h; Ambient temperature;A 8%
B 92%
menthyl alcohol

menthyl alcohol

1-acetoxycyclopentene
933-06-2

1-acetoxycyclopentene

acetic acid mentyl ester

acetic acid mentyl ester

B

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With tetrabutylammonium tricarbonylnitrosylferrate In hexane at 20 - 80℃; Molecular sieve; Inert atmosphere;A 92%
B n/a
4-(1-cyclopenten-1-yl)phenol
877-46-3

4-(1-cyclopenten-1-yl)phenol

A

cyclopentanone
120-92-3

cyclopentanone

B

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With hydrogenchloride; dihydrogen peroxide In acetonitrile at 50℃; for 3h; the excess of H2O2 was removed by catalytic hydrogenation using 10percent Pd-C;A n/a
B 91.6%
1-(trimethylsilyloxy)cyclopentene
19980-43-9

1-(trimethylsilyloxy)cyclopentene

A

cyclopent-2-enone
930-30-3

cyclopent-2-enone

B

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With oxygen; palladium matal-containing silica-supported catalyst In various solvent(s) at 59.9℃; for 24h; Product distribution; Mechanism; Pd(0) supported on various zeolites , influence of calcination and reaction temperature and of the solvent;A 90.1%
B n/a
With oxygen; silica gel; palladium In various solvent(s) at 59.9℃; for 24h; Product distribution; solvent;A 90.1%
B 0.8%
With oxygen; silica gel; palladium In various solvent(s) at 59.9℃; for 24h; Yields of byproduct given;A 90.1%
B n/a
With oxygen; silica gel; palladium In various solvent(s) at 59.9℃; for 24h;A 90.1%
B 0.8%
1,4-dioxaspiro[4.4]nonane
176-32-9

1,4-dioxaspiro[4.4]nonane

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With formaldehyd; silica gel; iron(III) chloride at 20℃; for 0.0833333h;90%
With chloral hydrate In hexane at 25℃; for 0.5h; Solvent; Temperature; Inert atmosphere;83%
With boron trifluoride diethyl etherate; sodium iodide In acetonitrile for 2h; Heating;82%
With water; β‐cyclodextrin at 20℃; for 16h;98 % Chromat.
2-cyclopentylidene-1,1-dimethylhydrazine
14090-60-9

2-cyclopentylidene-1,1-dimethylhydrazine

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With cerium(III) chloride; silica gel for 0.0666667h; Microwave irradiation;90%
With sodium perborate; sodium hydroxide; potassium dihydrogenphosphate; water In tert-butyl alcohol at 60℃; for 24h;70%
With ferric nitrate In dichloromethane 30 min., r.t., then reflux;69%
With silica gel In tetrahydrofuran; water at 25℃; for 10h;20%
1-methoxycyclopentene
1072-59-9

1-methoxycyclopentene

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With silica gel; iron(III) chloride at 20℃; for 0.333333h;90%
With sulfuric acid In water at 25℃; Rate constant;
cyclopentanone phenylhydrazone
1132-58-7

cyclopentanone phenylhydrazone

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With zirconium hydrogen sulfate; silica gel In hexane for 1.5h; Heating;90%
bis(η5-cyclopentadienyl)molybdenacyclopentane

bis(η5-cyclopentadienyl)molybdenacyclopentane

A

cyclopentadienylmolybdenum tricarbonyl dimer

cyclopentadienylmolybdenum tricarbonyl dimer

B

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With CO In toluene toluene soln. of Mo complex placed in autoclave under 50 atm CO pressure, stirred at 90°C for 12 h; distn., trapping at -78°C;A 83%
B 90%
(C4H9)3SnOC5H8Br

(C4H9)3SnOC5H8Br

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
decompn. at 150°C for 0.5 h;88%
decompn. at 150°C for 0.5 h;88%
1-(Trimethylsilyloxy)cyclohexene
6651-36-1

1-(Trimethylsilyloxy)cyclohexene

A

cyclohexenone
930-68-7

cyclohexenone

B

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With oxygen; silica gel; palladium In various solvent(s) at 59.9℃; for 24h;A 87.4%
B 0.8%
1-pyrrolidinocyclopent-1-ene
7148-07-4

1-pyrrolidinocyclopent-1-ene

2-((trifluoromethyl)thio)isoindoline-1,3-dione
719-98-2

2-((trifluoromethyl)thio)isoindoline-1,3-dione

A

cyclopentanone
120-92-3

cyclopentanone

B

2-((trifluoromethyl)thio)cyclopentanone

2-((trifluoromethyl)thio)cyclopentanone

Conditions
ConditionsYield
In acetonitrile at 25℃; for 48h; Hydrolysis; trifluoromethylthiolation;A 12.9%
B 87.1%
cyclopentene
142-29-0

cyclopentene

trans-1,2-dibromocyclopentane
10230-26-9

trans-1,2-dibromocyclopentane

B

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With water; oxygen; lithium bromide; copper(ll) bromide In tetrahydrofuran at 25℃; under 760.051 Torr;A 87%
B n/a
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

A

benzene-1,2-diol
120-80-9

benzene-1,2-diol

B

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With iodo trichloro silane for 1h; Ambient temperature;A 86%
B 39%
Adipic acid
124-04-9

Adipic acid

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With pyrographite at 450℃; for 0.5h;85%
With calcium hydroxide at 350℃; Product distribution; Further Variations:; Reagents;84.2%
at 290℃;
Cyclopentamine
1003-03-8

Cyclopentamine

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere; Green chemistry;85%
With oxygen; potassium iodide; sodium nitrite In water; acetonitrile for 8h; Reflux;75%
With potassium hydroxide In ethyl acetate at -78℃; Product distribution;18%
2-aminoacetophenone
551-93-9

2-aminoacetophenone

cyclopentanone
120-92-3

cyclopentanone

9-methyl-2,3-dihydro-1H-cyclopenta[b]quinoline
6829-07-8

9-methyl-2,3-dihydro-1H-cyclopenta[b]quinoline

Conditions
ConditionsYield
With 3-methyl-1-sulfoimidazolium trichloroacetate; trichloroacetic acid In neat (no solvent) at 100℃; Friedlaender Quinoline Synthesis;100%
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate; N,N-dimethyl-formamide at 90℃; Friedlaender reaction;98%
With ammonium cerium (IV) nitrate In ethanol for 16h; Friedlaender synthesis; Reflux;97%
benzaldehyde
100-52-7

benzaldehyde

cyclopentanone
120-92-3

cyclopentanone

2,5-dibenzylidenecyclopentanone
895-80-7

2,5-dibenzylidenecyclopentanone

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 20℃; Aldol Condensation;100%
With molybdenum(V) chloride In neat (no solvent) for 0.0416667h; Claisen-Schmidt Condensation; Microwave irradiation; Green chemistry;99%
With potassium hydroxide In ethanol at 40℃; for 0.00138889h;98%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

cyclopentanone
120-92-3

cyclopentanone

(2E,5E)-2,5-bis(4-methoxybenzylidene)cyclopentanone
5447-53-0, 106115-46-2

(2E,5E)-2,5-bis(4-methoxybenzylidene)cyclopentanone

Conditions
ConditionsYield
With lithium perchlorate; triethylamine at 20℃; for 0.0166667h;100%
With trichloro(trifluoromethanesulfonato)titanium(IV) at 20℃; for 2h; aldol condensation;97%
With animal bone meal catalyst modified with Na In water for 0.25h; Reflux;97%
cyclopentanone
120-92-3

cyclopentanone

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2-cyano-2-cyclopentylideneacetate
5407-83-0

ethyl 2-cyano-2-cyclopentylideneacetate

Conditions
ConditionsYield
piperidine at 23℃; under 750.06 Torr; for 2h; Knoevenagel condensation;100%
With morpholine; bis(acetylacetonate)oxovanadium at 40℃; for 1h; Reagent/catalyst; Temperature; Time; Knoevenagel Condensation;99%
With ammonium acetate; acetic acid In toluene Knoevenagel Condensation; Reflux;93%
cyclopentanone
120-92-3

cyclopentanone

2-chlorocyclopentanone
694-28-0

2-chlorocyclopentanone

Conditions
ConditionsYield
With iodine; mercury dichloride In dichloromethane for 1h; Ambient temperature;100%
With N-chloro-succinimide In various solvent(s) at 20℃; for 0.5h;91%
With N-chloro-succinimide In dimethyl sulfoxide at 20℃; for 0.25h;87%
cyclopentanone
120-92-3

cyclopentanone

Cyclopentanone oxime
1192-28-5

Cyclopentanone oxime

Conditions
ConditionsYield
With N,O-bis(trimethylsilyl)hydroxylamine; potassium hydride In tetrahydrofuran for 1.5h; Ambient temperature; - 78 deg C to room temp.;100%
With sodium hydroxide; hydroxylamine hydrochloride at 20℃; for 0.5h; grinding;100%
With hydroxylamine hydrochloride; sodium acetate In methanol Heating;100%
cyclopentanone
120-92-3

cyclopentanone

Cyclopentanol
96-41-3

Cyclopentanol

Conditions
ConditionsYield
With zirconium dioxide hydrate; isopropyl alcohol at 130℃; for 0.666667h; Meerwein-Ponndorf-Verley Reduction;100%
Stage #1: cyclopentanone With tetrabutylammonium tricarbonylnitrosylferrate; tricyclohexylphosphine In 1,4-dioxane at 50℃; Inert atmosphere;
Stage #2: With water; sodium hydroxide In 1,4-dioxane; methanol at 20℃; for 1.5h; Inert atmosphere; chemoselective reaction;
99%
With C15H18BF3; hydrogen; tert-butylimino-tri(pyrrolidino)phosphorane In tetrahydrofuran at 75℃; under 75007.5 Torr; for 20h; Glovebox;99%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

cyclopentanone
120-92-3

cyclopentanone

1-(trimethylsilyloxy)cyclopentene
19980-43-9

1-(trimethylsilyloxy)cyclopentene

Conditions
ConditionsYield
With triethylamine; sodium iodide In acetonitrile at 23℃; for 1.5h; Inert atmosphere;100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 40℃; for 0.5h;98%
With magnesium In N,N-dimethyl-formamide at 15 - 25℃;94%
4-penten-1-ylmagnesium bromide
34164-50-6

4-penten-1-ylmagnesium bromide

cyclopentanone
120-92-3

cyclopentanone

1-(pent-4'-enyl)cyclopentan-1-ol
16133-77-0

1-(pent-4'-enyl)cyclopentan-1-ol

Conditions
ConditionsYield
100%
at 0℃;90%
In diethyl ether for 2h; Ambient temperature;72%
nitromethane
75-52-5

nitromethane

cyclopentanone
120-92-3

cyclopentanone

phenylmethanethiol
100-53-8

phenylmethanethiol

1-benzylthio-1-nitromethylcyclopentane
335458-23-6

1-benzylthio-1-nitromethylcyclopentane

Conditions
ConditionsYield
With piperidine In benzene100%
With piperidine In acetonitrile for 4h; Heating;94%
With piperidine In benzene Heating;
benzoic acid hydrazide
613-94-5

benzoic acid hydrazide

cyclopentanone
120-92-3

cyclopentanone

N'-cyclopentylidene benzohydrazide
24214-78-6

N'-cyclopentylidene benzohydrazide

Conditions
ConditionsYield
at 143℃; under 2100.21 Torr; for 0.05h; Microwave irradiation; neat (no solvent);100%
for 0.05h; Microwave irradiation;100%
at 20℃; for 0.05h; Microwave irradiation;100%
3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

cyclopentanone
120-92-3

cyclopentanone

2,5-Bis<(3,4-dimethoxyphenyl)methylen>cyclopentanon
106115-49-5

2,5-Bis<(3,4-dimethoxyphenyl)methylen>cyclopentanon

Conditions
ConditionsYield
With lithium perchlorate; triethylamine at 20℃; for 96h;100%
With hydrogenchloride; acetic acid at 25 - 30℃; for 2h;85%
With hydrogenchloride In acetic acid at 25 - 30℃; for 2h;85%
allyl bromide
106-95-6

allyl bromide

cyclopentanone
120-92-3

cyclopentanone

1-allylcyclopentan-1-ol
36399-21-0

1-allylcyclopentan-1-ol

Conditions
ConditionsYield
With ammonium acetate; zinc In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;100%
With zinc; bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran for 0.0833333h; Ambient temperature;98%
With ammonium chloride; zinc In tetrahydrofuran; water at 20℃; for 10h;90%
methanol
67-56-1

methanol

cyclopentanone
120-92-3

cyclopentanone

1,1-dimethoxycyclopentane
931-94-2

1,1-dimethoxycyclopentane

Conditions
ConditionsYield
With trimethyl orthoformate at 40℃; under 6000480 Torr; for 8h;100%
Irradiation;25%
Ce(3+)-mont at 25℃; for 0.5h; Yield given;
t-butoxycarbonylhydrazine
870-46-2

t-butoxycarbonylhydrazine

cyclopentanone
120-92-3

cyclopentanone

tert-butyl 2-cyclopentylidenehydrazine carboxylate
79201-39-1

tert-butyl 2-cyclopentylidenehydrazine carboxylate

Conditions
ConditionsYield
In methanol at 20℃; for 2h;100%
In methanol at 20℃; for 3h; Inert atmosphere;98%
In hexane for 0.333333h; Heating;96%
1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

cyclopentanone
120-92-3

cyclopentanone

1-Naphthylcyclopentanol
74709-98-1

1-Naphthylcyclopentanol

Conditions
ConditionsYield
With iodine; magnesium In diethyl ether for 3h; Grignard reaction; Heating;100%
With iodine; magnesium 1.) ether, reflux, 2.) ether, benzene, RT, 2 h; Yield given. Multistep reaction;
Stage #1: 1-Bromonaphthalene With magnesium In diethyl ether
Stage #2: cyclopentanone In diethyl ether for 3h; Grignard reaction;
Stage #1: 1-Bromonaphthalene With magnesium In diethyl ether for 0.5h; Reflux;
Stage #2: cyclopentanone In diethyl ether at 0℃; for 1h;
2,4,6-trimethylbenzenesulfonohydrazide
16182-15-3

2,4,6-trimethylbenzenesulfonohydrazide

cyclopentanone
120-92-3

cyclopentanone

N'-cyclopentylidene-2,4,6-trimethylbenzenesulfonohydrazide
83477-71-8

N'-cyclopentylidene-2,4,6-trimethylbenzenesulfonohydrazide

Conditions
ConditionsYield
In methanol at 20℃;100%
In methanol 1.) 50 deg, 2.) room temperature;88%
t-butyldimethylsiyl triflate
69739-34-0

t-butyldimethylsiyl triflate

cyclopentanone
120-92-3

cyclopentanone

1-tert-butyldimethylsilyloxycyclopentene
68081-15-2

1-tert-butyldimethylsilyloxycyclopentene

Conditions
ConditionsYield
With triethylamine In dichloromethane for 0.0833333h;100%
With 2,6-dimethylpyridine In tetrahydrofuran at 0℃; for 1h;71%
With triethylamine In dichloromethane at 0℃;
ethyl hydrogen (5,6-dihydro-p-dioxin-2-yl)ethylphosphonite
78396-88-0

ethyl hydrogen (5,6-dihydro-p-dioxin-2-yl)ethylphosphonite

cyclopentanone
120-92-3

cyclopentanone

ethyl (5,6-dihydro-p-dioxin-2-yl)(1-hydroxycyclopentyl)phosphinate

ethyl (5,6-dihydro-p-dioxin-2-yl)(1-hydroxycyclopentyl)phosphinate

Conditions
ConditionsYield
for 600h; Ambient temperature;100%
cyclopentanone
120-92-3

cyclopentanone

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

1,2-diamino-benzene

2,3-cyclopentano-3,4-dihydro-5H-4-spirocyclopentano-1,5-benzodiazepine
41526-78-7

2,3-cyclopentano-3,4-dihydro-5H-4-spirocyclopentano-1,5-benzodiazepine

Conditions
ConditionsYield
With mesoporous aluminosilicate MCM-41(14) at 100℃; for 1h;100%
With ytterbium(III) triflate at 20℃; for 4h;99%
With octadecafluorodecahydronaphthalene (cis+trans) at 60℃; for 2h;99%
cyclopentanone
120-92-3

cyclopentanone

toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

cyclopentanone p-tolylsulfonylhydrazone
17529-98-5

cyclopentanone p-tolylsulfonylhydrazone

Conditions
ConditionsYield
In ethanol at 100℃; for 1h;100%
In ethanol at 100℃; for 1.66667h; Inert atmosphere;100%
In methanol at 20℃; Inert atmosphere;99.5%
cyclopentanone
120-92-3

cyclopentanone

2-amino-1-benzylamine
4403-69-4

2-amino-1-benzylamine

3',4'-dihydro-1'H-spiro[cyclopentane-1,2'-quinazoline]
84571-63-1

3',4'-dihydro-1'H-spiro[cyclopentane-1,2'-quinazoline]

Conditions
ConditionsYield
In chloroform at 60℃; for 24h;100%
With acetic acid In ethanol for 3h; Heating;82%
cyclopentanone
120-92-3

cyclopentanone

4-flourophenylmagnesium bromide
352-13-6

4-flourophenylmagnesium bromide

1-cyclopent-1-enyl 4-fluorobenzene
827-57-6

1-cyclopent-1-enyl 4-fluorobenzene

Conditions
ConditionsYield
Stage #1: cyclopentanone; 4-flourophenylmagnesium bromide In tetrahydrofuran at 0℃; Reflux;
Stage #2: With hydrogenchloride In tetrahydrofuran; water
100%
In tetrahydrofuran; diethyl ether at 0℃; for 2h; Reflux;100%
Stage #1: cyclopentanone; 4-flourophenylmagnesium bromide In tetrahydrofuran at 0℃; for 2h; Reflux;
Stage #2: With hydrogenchloride; water In tetrahydrofuran Cooling with ice;
100%
In diethyl ether Grignard reaction; Reflux;61%
(i), (ii) KHSO4; Multistep reaction;
furfural
98-01-1

furfural

cyclopentanone
120-92-3

cyclopentanone

α,α'-bis(2-furylmethylidene)cyclopentanone

α,α'-bis(2-furylmethylidene)cyclopentanone

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 0.0166667h; microwave irradiation;100%
With aluminum oxide; potassium fluoride In methanol at 35 - 40℃; for 0.5h; Claisen-Schmidt condensation; ultrasound irradiation;96%
With sodium-modified hydroxyapatite In water for 0.5h; Aldol condensation; Reflux;96%
nitromethane
75-52-5

nitromethane

thiophenol
108-98-5

thiophenol

cyclopentanone
120-92-3

cyclopentanone

1-nitromethyl-1-phenylthiocyclopentane
109585-27-5

1-nitromethyl-1-phenylthiocyclopentane

Conditions
ConditionsYield
With piperidine In benzene for 61h; Heating;100%

120-92-3Related news

Improving stability of Cyclopentanone (cas 120-92-3) aldol condensation MgO-based catalysts by surface hydrophobization with organosilanes09/06/2019

Cyclopentanone is a promising building block in the conversion of biomass to fuels. It can be readily obtained from furanics derived from biomass and can be converted to intermediate products in the molecular weight range compatible with fuels via CC bond forming reactions. Among them, aldol con...detailed

Highly efficient hydrogenative ring-rearrangement of furanic aldehydes to Cyclopentanone (cas 120-92-3) compounds catalyzed by noble metals/MIL-MOFs09/05/2019

Hydrogenative ring-rearrangement reaction of biomass-derived furanic aldehydes to cyclopentanone compounds catalyzed by metal/support bifunctional catalysts suffers a low selectivity of target product and serious carbon loss because of the Brønsted acid catalysis. Herein, a series of pure Lewis ...detailed

Laminar flame characteristics of Cyclopentanone (cas 120-92-3) at elevated temperatures09/02/2019

Cyclopentanone, a product of biomass pyrolysis of agricultural waste, has certain advantages as a biofuel candidate but so far little is known about its combustion characteristics. In this paper, the laminar flame characteristics of cyclopentanone, including stretched flame propagation speed, un...detailed

Short communicationPd/Cu-MOF as a highly efficient catalyst for synthesis of Cyclopentanone (cas 120-92-3) compounds from biomass-derived furanic aldehydes08/31/2019

Herein, a series of Pd nanoparticles supported on Cu-MOFs (Cu3(BTC)2, FeCu-DMC) with pure Lewis acidity are synthesized for hydrogenative ring-rearrangement reaction of furanic aldehydes (furfural, 5-hydroxymethyl furfural) to cyclopentanone compounds (cyclopentanone, 3-hydroxymethyl cyclopentan...detailed

Role of water in Cyclopentanone (cas 120-92-3) self-condensation reaction catalyzed by MCM-41 functionalized with sulfonic acid groups08/30/2019

Water is ubiquitous in many catalytic reactions used in the upgrading of biomass. Therefore, quantifying and controlling the influence of water in activity, selectivity, and catalyst deactivation is essential for advancing this technology. Here, we report a kinetic study of the cyclopentanone se...detailed

120-92-3Relevant articles and documents

Efficient conversion of furfural into cyclopentanone over high performing and stable Cu/ZrO2 catalysts

Zhang, Yifeng,Fan, Guoli,Yang, Lan,Li, Feng

, p. 117 - 126 (2018)

Currently, biomass transformation to produce high value-added chemicals and liquid biofuels is attracting more and more interest by the virtue of its importance in the sustainable development of human society. Herein, we reported the conversion of furfural (FFA) into cyclopentanone (CPO) in water over high performing and stable Cu/ZrO2 catalysts prepared by our developed one-pot reduction-oxidation method. It was demonstrated that surface structures and catalytic performances of catalysts could be delicately adjusted by varying the calcination temperatures for catalyst precursors. Especially, an appropriate calcination temperature of 500 °C could significantly enhance the interactions between surface Cu species and the ZrO2 support, thus greatly facilitating the formation of Cu+-O-Zr-like structure at the metal-support interface, and the resulting Cu/ZrO2 catalyst showed a superior catalytic performance with a high CPO yield of 91.3% under mild reaction conditions (i.e. a low hydrogen pressure of 1.5 MPa and 150 °C) to other metal oxides supported copper catalysts prepared by the conventional impregnation. It was revealed that in addition to surface acidic sites, surface Cu+/(Cu°+Cu+) ratio also played a key role in promoting the formation of CPO in the present Cu/ZrO2 catalytic system.

-

Brooks

, p. 3693,3695 (1958)

-

PREPARATION OF KETONES BY A NOVEL DECARBALKOXYLATION OF β-KETO ESTERS: STEREOELECTRONIC ASSISTANCE TO C-C BOND FISSION

Aneja, R.,Hollis, W. M.,Davies A. P.,Eaton, G.

, p. 4641 - 4644 (1983)

Reaction of β-keto esters with the sodium derivative of propane-1,2-diol in an excess of anhydrous propane-1,2-diol causes facile decarboxylation to ketones in excellent yields.

Synthesis of Unsaturated Spiroacetals, Cyclopentanone Derivatives, in the Presence of Natural Aluminosilicate Modified with Zirconium Cations

Abbasov,Alimardanov, Kh. M.,Abbaszade,Guseinova,Azimli

, p. 603 - 607 (2019)

Abstract: Conditions for the condensation of cyclopentanone and n-valeric aldehyde to 2-pentylidenecyclopentanone in the presence of an alcoholic solution of piperidine have been developed. The isomerization of the latter in a continuous-flow system over γ-Al2O3 yields 2-pentylcyclopent-2-en-1-one. The condensation of the obtained unsaturated ketones with ethane-1,2-diol in the presence of a heterogeneous catalyst, a natural aluminosilicate (perlite) modified with zirconyl sulfate, has been studied. The optimum conditions for the preparation of the corresponding unsaturated spiroacetals have been found. The synthesized compounds can be used as synthetic fragrances for different purposes.

Regeneration of aldehydes and ketones from oximes using bis(trimethylsilyl)chromate

Lee,Kwak,Hwang

, p. 2425 - 2429 (1992)

Bis(trimethylsilyl) chromate transforms oximes of not only ketones but also aldehydes and 1,2-diketones to the corresponding carbonyl compounds, in high yields.

Mild homogeneous oxidation and hydrocarboxylation of cycloalkanes catalyzed by novel dicopper(II) aminoalcohol-driven cores

Fernandes, Tiago A.,André, Vania,Kirillov, Alexander M.,Kirillova, Marina V.

, p. 357 - 367 (2017)

N-benzylethanolamine (Hbea) and triisopropanolamine (H3tipa) were applied as unexplored aminoalcohol N,O-building blocks for the self-assembly generation of two novel dicopper(II) compounds, [Cu2(μ-bea)2(Hbea)2](NO3)2 (1) and [Cu2(H3tipa)2(μ-pma)]·7H2O (2) {H4pma = pyromellitic acid}. These were isolated as stable and aqua-soluble microcrystalline products and were fully characterized by IR spectroscopy, ESI–MS(±), and single-crystal X-ray diffraction, the latter revealing distinct Cu2 cores containing the five-coordinate copper(II) centers with the {CuN2O3} or {CuNO4} environments. Compounds 1 and 2 were used as homogeneous catalysts for the mild oxidation of C5–C8 cycloalkanes to give the corresponding cyclic alcohols and ketones in up to 23% overall yields based on cycloalkane. The reactions proceed in aqueous acetonitrile medium at 50 °C using H2O2 as an oxidant. The effects of different reaction conditions were studied, including the type and loading of catalyst, amount and kind of acid promoter, and water concentration. Despite the fact that different acids (HNO3, H2SO4, HCl, or CF3COOH) promote the oxidation of alkanes, the reaction is exceptionally fast in the presence of a catalytic amount of HCl, resulting in the TOF values of up to 430 h?1. Although water typically strongly inhibits alkane oxidations due to the reduction of H2O2 concentration and lowering of the alkane solubility, in the systems comprising 1 and 2 we observed a significant growth (up to 5-fold) of an initial reaction rate in the cyclohexane oxidation on increasing the amount of H2O in the reaction mixture. The bond-, regio- and stereo-selectivity parameters were investigated in oxidation of different linear, branched, and cyclic alkane substrates. Both compounds 1 and 2 also catalyze the hydrocarboxylation of C5–C8 cycloalkanes, by CO, K2S2O8, and H2O in a water/acetonitrile medium at 60 °C, to give the corresponding cycloalkanecarboxylic acids in up to 38% yields based on cycloalkanes.

Solvent and substituent effects on the thermolysis of antimalarial fluorophenyl substituted 1,2.4-trioxanes

Cafferata, Lazaro F. R.,Rimada, Ruben S.

, p. 655 - 662 (2003)

The kinetics and mechanism of the thermal decomposition reaction of cis-6-(4-fluoropheny1)-5,6-[2-(4-fluorophenyl)-propylidene]-3, 3-tetramethylene-1,2,4-trioxacyclo-hexane (I) were investigated separately in n-hexane and in methanol solutions over the te

Hydrogenolysis of Furfuryl Alcohol to 1,2-Pentanediol Over Supported Ruthenium Catalysts

Yamaguchi, Aritomo,Murakami, Yuka,Imura, Tomohiro,Wakita, Kazuaki

, p. 731 - 736 (2021)

Hydrogenolysis of the furan rings of furfural and furfuryl alcohol, which can be obtained from biomass, has attracted attention as a method for obtaining valuable chemicals such as 1,2-pentanediol. In this study, we examined the hydrogenolysis of furfuryl alcohol to 1,2-pentanediol over Pd/C, Pt/C, Rh/C, and various supported Ru catalysts in several solvents. In particular, we investigated the effects of combinations of solvents and supports on the reaction outcome. Of all the tested combinations, Ru/MgO in water gave the best selectivity for 1,2-pentanediol: with this catalyst, 42 % selectivity for 1,2-pentanediol was achieved upon hydrogenolysis of furfuryl alcohol for 1 h at 463 K. In contrast, reaction in water in the presence of Ru/Al2O3 afforded cyclopentanone and cyclopentanol by means of hydrogenation and rearrangement reactions.

Highly selective hydrogenation of furfural to tetrahydrofurfuryl alcohol over MIL-101(Cr)-NH2 supported Pd catalyst at low temperature

Yin, Dongdong,Ren, Hangxing,Li, Chuang,Liu, Jinxuan,Liang, Changhai

, p. 319 - 326 (2018)

An efficient heterogeneous catalyst, Pd@MIL-101(Cr)-NH2, is prepared through a direct pathway of anionic exchange followed by hydrogen reduction with amino-containing MIL-101 as the host matrix. The composite is thermally stable up to 350 °C and the Pd nanoparticles uniformly disperse on the matal organic framework (MOF) support, which are attributed to the presence of the amino groups in the frameworks of MIL-101(Cr)-NH2. The selective hydrogenation of biomass-based furfural to tetrahydrofurfuryl alcohol is investigated by using this multifunctional catalyst Pd@MIL-101(Cr)-NH2 in water media. A complete hydrogenation of furfural is achieved at a low temperature of 40 °C with the selectivity of tetrahydrofurfuryl alcohol close to 100%. The amine-functionalized MOF improves the hydrogen bonding interactions between the intermediate furfuryl alcohol and the support, which is conducive for the further hydrogenation of furfuryl alcohol to tetrahydrofurfuryl alcohol in good coordination with the metal sites.

Catalytic hydrogenation of furfural to tetrahydrofurfuryl alcohol using competitive nickel catalysts supported on mesoporous clays

Sunyol,English Owen,González,Salagre,Cesteros

, (2021)

Nickel catalysts supported on mesoporous clays with different acid properties, such as montmorillonite MK-10, Al-pillared montmorillonite, mesoporous Na-saponite and mesoporous H-saponite, were prepared, characterized and tested for the hydrogenation of furfural to tetrahydrofurfuryl alcohol (THFA). Clays were also modified introducing basicity through magnesium oxide in different amounts. Catalysts with higher acidity or low amounts of metallic centres favoured deactivation and/or selectivity to the non-desired products. Interestingly, the addition of MgO both neutralized the acidity of the montmorillonite supports and improved the hydrogenation of the furanic ring, resulting in higher selectivity to THFA. The best catalyst was the one prepared with montmorillonite MK-10 covered by 30 wt% of magnesium oxide and with 8.8 % of the Ni metal phase achieving total conversion and total selectivity to THFA. The activity of this catalyst was maintained after several reuses.

Ruthenium Trichloride Catalyst in Water: Ru Colloids versus Ru Dimer Characterization Investigations

Lebedeva, Anastasia,Albuquerque, Brunno L.,Domingos, Josiel B.,Lamonier, Jean-Fran?ois,Giraudon, Jean-Marc,Lecante, Pierre,Denicourt-Nowicki, Audrey,Roucoux, Alain

, p. 4141 - 4151 (2019)

An easy-to-prepare ruthenium catalyst obtained from ruthenium(III) trichloride in water demonstrates efficient performances in the oxidation of several cycloalkanes with high selectivity toward the ketone. In this work, several physicochemical techniques were used to demonstrate the real nature of the ruthenium salt still unknown in water and to define the active species for this Csp3-H bond functionalization. From transmission electron microscopy analyses corroborated by SAXS analyses, spherical nanoobjects were observed with an average diameter of 1.75 nm, thus being in favor of the formation of reduced species. However, further investigations, based on X-ray scattering and absorption analyses, showed no evidence of the presence of a metallic Ru-Ru bond, proof of zerovalent nanoparticles, but the existence of Ru-O and Ru-Cl bonds, and thus the formation of a water-soluble complex. The EXAFS (extended X-ray absorption fine structure) spectra revealed the presence of an oxygen-bridged diruthenium complex [Ru(OH)xCl3-x]2(μ-O) with a high oxidation state in agreement with catalytic results. This study constitutes a significant advance to determine the true nature of the RuCl3·3H2O salt in water and proves once again the invasive nature of the electron beam in microscopy experiments, routinely used in nanochemistry.

Simultaneous Upgrading of Furanics and Phenolics through Hydroxyalkylation/Aldol Condensation Reactions

Bui, Tuong V.,Sooknoi, Tawan,Resasco, Daniel E.

, p. 1631 - 1639 (2017)

The simultaneous conversion of cyclopentanone and m-cresol has been investigated on a series of solid-acid catalysts. Both compounds are representative of biomass-derived streams. Cyclopentanone can be readily obtained from sugar-derived furfurals through Piancatelli rearrangement under reducing conditions. Cresol represents a family of phenolic compounds, typically obtained from the depolymerization of lignin. In the first biomass conversion strategy proposed here, furfural is converted in high yields and selectivity to cyclopentanone (CPO) over metal catalysts such as Pd-Fe/SiO2 at 600 psi (~4.14 MPa) H2 and 150 °C. Subsequently, CPO and cresol are further converted through acid-catalyzed hydroxyalkylation. This C?C coupling reaction may be used to generate products in the molecular weight range that is appropriate for transportation fuels. As molecules beyond this range may be undesirable for fuel production, a catalyst with a suitable porous structure may be advantageous for controlling the product distribution in the desirable range. If Amberlyst resins were used as a catalyst, C12–C24 products were obtained whereas when zeolites with smaller pore sizes were used, they selectively produced C10 products. Alternatively, CPO can undergo the acid-catalyzed self-aldol condensation to form C10 bicyclic adducts. As an illustration of the potential for practical implementation of this strategy for biofuel production, the long-chain oxygenates obtained from hydroxyalkylation/aldol condensation were successfully upgraded through hydrodeoxygenation to a mixture of linear alkanes and saturated cyclic hydrocarbons, which in practice would be direct drop-in components for transportation fuels. Aqueous acidic environments, which are typically encountered during the liquid-phase upgrading of bio-oils, would inhibit the efficiency of base-catalyzed processes. Therefore, the proposed acid-catalyzed upgrading strategy is advantageous for biomass conversion in terms of process simplicity.

Effect of Ni Metal Content on Emulsifying Properties of Ni/CNTox Catalysts for Catalytic Conversion of Furfural in Pickering Emulsions

Herrera,Pinto-Neira,Fuentealba,Sepúlveda,Rosenkranz,García-Fierro,González,Escalona

, p. 682 - 694 (2021)

Ni/CNTox catalysts with variable metal content have been prepared to investigate their emulsifying and catalytic properties for the liquid-phase conversion of furfural. The solid catalysts and emulsions were analyzed by several characterization techniques. The catalytic activity linearly increased with increasing Ni content (up to 10 wt.%) before dropping down again for a Ni content of 15 wt.%. The loss of catalytic activity was attributed to larger emulsion droplets formed by the inhibition of hydrophilic sites. All Ni/CNTox catalysts were highly selective to cyclopentanone as a main product, while several changes regarding secondary products were observed. Ni/CNTox catalysts with a Ni content up to 10 wt.% favor the formation of levulinic acid, while catalysts with a Ni content of 15 wt.% were selective to tetrahydrofurfuryl alcohol. This was attributed to an inhibition of the acid sites thus favoring the catalyst's hydrogenation capacity.

Wacker-type oxidation of cyclopentene under dioxygen atmosphere catalyzed by Pd(OAc)2/NPMoV on activated carbon

Kishi, Arata,Higashino, Takashi,Sakaguchi, Satoshi,Ishii, Yasutaka

, p. 99 - 102 (2000)

Wacker-type oxidation of cyclopentene to cyclopentanone under dioxygen atmosphere was successfully achieved by the use of Pd(OAc)2 and molybdovanadophosphate supported on activated carbon, [Pd(OAc)2-NPMoV/C], catalyst. Thus, the reaction of cyclopentene under O2 (1 atm) in aqueous acetonitrile acidified by CH3SO3H in the presence of [Pd(OAc)2-NPMoV/C] at 50°C produced cyclopentanone in 85% yield along with a small amount of cyclopentenone (1%).

Characterization and reactivity of γ-Al2O3 supported Pd-Cu bimetallic nanocatalysts for the selective oxygenization of cyclopentene

Liu, Wei-Wei,Feng, Yi-Si,Wang, Guang-Yu,Jiang, Wei-Wei,Xu, Hua-Jian

, p. 905 - 909 (2016)

In this work, Pd-Cu/γ-Al2O3 is prepared by the impregnation method and investigated for selective oxygenization of cyclopentene to cyclopentanone. A series of bimetallic Pd-Cu/γ-Al2O3 nanocatalysts were prepared and the structures characterized by XRD, XPS and TEM. We determined that the obtained Pd-Cu/γ-Al2O3 (molar ratio Pd:Cu = 5:1) was an efficient catalyst for the oxygenization of cyclopentene to cyclopentanone with >95% selectivity and >85% conversion (100 °C, 1 MPa initial O2 pressure, 7 h).

Influence of furanic polymers on selectivity of furfural rearrangement to cyclopentanone

Hronec, Milan,Fulajtárova, Katarina,Mi?u?ik, Matej

, p. 426 - 431 (2013)

The influence of furanic polymers upon the activity and selectivity of Ni, Pd, Pt catalysts in rearrangement of furfural to cyclopentanone, and its consecutive hydrogenation to cyclopentanol in an aqueous phase has been studied. The coverage of surface of

Novel Technique for the Generation of Bis(polyfluoroalkyl) and Polyfluoroalkyl Nitroalkyl Nitroxides. ESR Verification of Mechanistic Propositions for the Reactions between Polyfluorodiacyl Peroxides and Carbanions Derived from Secondary Nitroalkanes

Zhao, Cheng-Xue,Jiang, Xi-Kui,Chen, Guo-Fei,Qu, Yan-Ling,Wang, Xian-Shan,Lu, Jian-Ying

, p. 3132 - 3133 (1986)

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Liberman et al.

, (1971)

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A one-pot synthesis of 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane by hydrodeoxygenation of xylose using a palladium catalyst

Jackson, Michael A.,Blackburn, Judith A.,Price, Neil P.J.,Vermillion, Karl E.,Peterson, Steven C.,Ferrence, Gregory M.

, p. 9 - 16 (2016)

In an effort to expand the number of biobased chemicals available from sugars, xylose has been converted to 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane in a one-pot reaction using palladium supported on silica-alumina as the catalyst. The title compound is produced in 35-40% yield under 7 MPa H2 pressure at 733 K using 3-10 wt%Pd on silica-alumina catalyst. It is isolated using a combination of liquid-liquid extractions and flash chromatography. This dimer can be converted to its monomer, 2-hydroxy-(2-hydroxymethyl)tetrahydrofuran, which ring opens under acid conditions to 1,5-dihydroxy-2-pentanone. This diol can then be esterified with vinylacetate in phosphate buffer to produce 1,5-bis(acetyloxy)-2-pentanone which is an inhibitor of mammalian 11β-hydroxysteroid dehydrogenase 1. 1H and 13C nmr spectra of each of these species are reported. The single crystal X-ray structure of the title compound is also reported. These data were collected in a temperature range of 100 K-273 K and show a solid state phase change from triclinic to monoclinic between 175 K and 220 K without a conformational change.

Aqueous phase hydrogenation of furfural to tetrahydrofurfuryl alcohol on alkaline earth metal modified Ni/Al2O3

Yang, Yanliang,Ma, Jiping,Jia, Xiuquan,Du, Zhongtian,Duan, Ying,Xu, Jie

, p. 51221 - 51228 (2016)

Al2O3 modified by alkaline earth metals M-Al2O3 (M = Mg, Ca, Sr, Ba) was synthesised by coprecipitation method. The nickel-based catalysts supported by M-Al2O3 were prepared by impregnation method. The catalysts were characterized by TEM, N2 adsorption/desorption, XRD, H2-TPR, NH3-TPD and XPS, and used for the direct hydrogenation of furfural to tetrahydrofurfuryl alcohol (THFA) in water. The reaction was demonstrated to proceed through furfuryl alcohol as an intermediate. The modification of Al2O3 by alkaline earth metals has a significant effect on the activity and selectivity of THFA. A high yield of THFA was obtained over Ni/Ba-Al2O3 under optimized conditions. Moreover, the catalyst is recyclable and reusable at least four times without significant loss of the conversion of furfural and selectivity of THFA.

Synthesis of azasilacyclopentenes and silanols: Via Huisgen cycloaddition-initiated C-H bond insertion cascades

Shih, Jiun-Le,Jansone-Popova, Santa,Huynh, Christopher,May, Jeremy A.

, p. 7132 - 7137 (2017)

An unusual transition metal-free cascade reaction of alkynyl carbonazidates was discovered to form azasilacyclopentenes. Mild thermolysis afforded the products via a series of cyclizations, rearrangements, and an α-silyl C-H bond insertion (rather than the more common Wolff rearrangement, 1,2-shift, or β-silyl C-H insertion) to form silacyclopropanes. A mechanistic proposal for the sequence was informed by control experiments and the characterization of reaction intermediates. The substrate scope and post-cascade transformations were also explored.

Selective reduction of α,β-unsaturated aldehydes and ketones to allylic alcohols with diisobutylalkoxyalanes

Cha, Jin Soon,Kwon, Oh Oun,Kwon, Sang Yong

, p. 355 - 360 (1996)

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Hydrogenative Ring-Rearrangement of Biobased Furanic Aldehydes to Cyclopentanone Compounds over Pd/Pyrochlore by Introducing Oxygen Vacancies

Deng, Qiang,Deng, Shuguang,Gao, Rui,Li, Xiang,Wang, Jun,Zeng, Zheling,Zou, Ji-Jun

, p. 7355 - 7366 (2020)

Upgrading furanic aldehydes (such as furfural or 5-hydroxymethyl furfural) to cyclopentanone compounds (such as cyclopentanone or 3-hydroxymethyl cyclopentanone) is of great significance for the synthesis of high-value chemicals and biomass utilization. Developing an efficient reduced metal/acidic support with Lewis acidity is the key to facilitating the carbonyl hydrogenation and hydrolysis steps in the hydrogenative ring-rearrangement reaction. Herein, three pure Lewis acidic pyrochlore supports of the form A2B2O7 (La2Sn2O7, Y2Sn2O7, and Y2(Sn0.7Ce0.3)2O7-δ) with the same crystal structures and different metals are synthesized. The Lewis acidity and the surface properties of the pyrochlore can be tuned by inserting different kinds of A and B site metals. After impregnation, Pd nanoparticles with appropriate particle sizes are uniformly loaded on the surface of pyrochlore. For the reaction of the furanic aldehydes, all of these pyrochlore-based catalysts exhibit hydrogenation and hydrolysis rates that are both faster than those of traditional support-based catalysts due to the oxygen vacancy and pure Lewis acidity of the support. Among these pyrochlore-based catalysts, Pd/Y2Sn2O7 exhibits activity and selectivity that are higher than those of Pd/La2Sn2O7. Moreover, the Y2Sn2O7-based catalyst partially substituted by Ce3+ ions at the B site is more efficient, with the highest cyclopentanone yield and 3-hydroxymethyl cyclopentanone yield of 95.0percent and 92.5percent, respectively. Furthermore, the catalyst can still maintain an effective activity and stability after 4 runs. This study not only presents an efficient biobased route for the production of cyclopentanone compounds but also focuses on the acid catalytic performance of pyrochlore based on its pure Lewis acidity.

Production of cyclopentanone from furfural over Ru/C with Al11.6PO23.7 and application in the synthesis of diesel range alkanes

Shen, Tao,Hu, Ruijia,Zhu, Chenjie,Li, Ming,Zhuang, Wei,Tang, Chenglun,Ying, Hanjie

, p. 37993 - 38001 (2018)

The bio-based platform molecule furfural was converted to the high value chemical cyclopentanone over Ru/C (0.5?wt%) and Al11.6PO23.7 catalysts in good yield (84%) with water as the medium. After screening the reaction conditions, the selectivity for cyclopentanone and cyclopentanol could be controlled by adjusting the hydrogen pressure at the temperature of 433 K. Herein, we propose a new mechanism for the synergistic catalysis of a Bronsted acid and Lewis acid for the conversion of furfural to cyclopentanone through the cyclopentenone route, which is catalyzed by Ru/C and Al11.6PO23.7. In addition, based on cyclopentanone, higher octane number cyclic alkanes (>85% selectivity), which are used as hydrocarbon fuels, were synthesized via a C-C coupling reaction followed by hydrodeoxygenation.

Photoinduced reversible structural transformation and selective oxidation catalysis of unsaturated ruthenium complexes supported on SiO2

Tada, Mizuki,Akatsuka, Yusaku,Yang, Yong,Sasaki, Takehiko,Kinoshita, Mutsuo,Motokura, Ken,Iwasawa, Yasuhiro

, p. 9252 - 9255 (2008)

(Chemical Equation Presented) Ru experienced? Two novel coordinatively unsaturated SiO2-supported Ru complexes were prepared by photoinduced ligand elimination, accompanied by dissociative coordination of a surface OH group to the unsaturated Ru center by photoirradiation. Wavelength- and atmosphere-dependent photoinduced reversible interconversion occurs between the two Ru complexes. One of the complexes is catalytically active for the photooxidation of cycloalkanes with O2.

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.

Application of imidazole carbonate in preparation of chemical intermediate

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Paragraph 0036-0049, (2021/03/13)

The invention provides an application of an imidazole carbonate in preparation of a chemical intermediate cyclopentanone, which is characterized by comprising the following steps: placing cyclopentenein a reaction vessel, adding ionic liquid imidazole carbonate and a Wacker catalyst, introducing an oxygen source, stirring and heating to react at normal pressure, and carrying out after-treatment to obtain cyclopentanone. The ionic liquid imidazole carbonate is used as a solvent, the system can fully react without a high-pressure condition, the reaction time is greatly shortened, the high yieldand purity of the product can be ensured, the method is particularly suitable for industrial production, and an unexpected technical effect is achieved.

Chemoselective Hydrogenation of Olefins Using a Nanostructured Nickel Catalyst

Klarner, Mara,Bieger, Sandra,Drechsler, Markus,Kempe, Rhett

supporting information, p. 2157 - 2161 (2021/05/21)

The selective hydrogenation of functionalized olefins is of great importance in the chemical and pharmaceutical industry. Here, we report on a nanostructured nickel catalyst that enables the selective hydrogenation of purely aliphatic and functionalized olefins under mild conditions. The earth-abundant metal catalyst allows the selective hydrogenation of sterically protected olefins and further tolerates functional groups such as carbonyls, esters, ethers and nitriles. The characterization of our catalyst revealed the formation of surface oxidized metallic nickel nanoparticles stabilized by a N-doped carbon layer on the active carbon support.

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