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1,4-Benzoquinone, also known as p-benzoquinone or quinone, is a yellowish-colored crystalline solid with a pungent, irritating odor. It is a chemical intermediate that is widely distributed in the natural world, being found in bacteria, plants, and arthropods, and plays a pivotal role in biological functions such as oxidative phosphorylation and electron transfer. It is poisonous by ingestion or inhalation of vapors and may severely damage skin, eyes, and mucous membranes.

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  • 106-51-4 Structure
  • Basic information

    1. Product Name: 1,4-Benzoquinone
    2. Synonyms: p-Benzoquinone(8CI);1,4-Cyclohexadienedione;Chinone;NSC 36324;PBQ 2;Stearer PBQ;p-Quinone;Quinone;
    3. CAS NO:106-51-4
    4. Molecular Formula: C6H4O2
    5. Molecular Weight: 108.0948
    6. EINECS: 203-405-2
    7. Product Categories: Intermediates of Dyes and Pigments;Benzoquinones, etc. (Charge Transfer Complexes);Charge Transfer Complexes for Organic Metals;Benzoquinones;Functional Materials;fine chemicals
    8. Mol File: 106-51-4.mol
  • Chemical Properties

    1. Melting Point: 112-116℃
    2. Boiling Point: 174 ºC at 760 mmHg
    3. Flash Point: 59.3 ºC
    4. Appearance: gold powder
    5. Density: 1.256 g/cm3
    6. Vapor Density: 3.73 (vs air)
    7. Vapor Pressure: 0.166mmHg at 25°C
    8. Refractive Index: 1.543
    9. Storage Temp.: 2-8°C
    10. Solubility: 10g/l
    11. PKA: 7.7
    12. Water Solubility: 10 g/L (25℃)
    13. Stability: Stable, but light sensitive. Incompatible with strong oxidizing agents. Flammable.
    14. Merck: 14,8074
    15. BRN: 773967
    16. CAS DataBase Reference: 1,4-Benzoquinone(CAS DataBase Reference)
    17. NIST Chemistry Reference: 1,4-Benzoquinone(106-51-4)
    18. EPA Substance Registry System: 1,4-Benzoquinone(106-51-4)
  • Safety Data

    1. Hazard Codes:  T:Toxic;
    2. Statements: R23/25:; R36/37/38:; R50:;
    3. Safety Statements: S26:; S28A:; S45:; S61:;
    4. RIDADR: UN 2587 6.1/PG 2
    5. WGK Germany: 3
    6. RTECS: DK2625000
    7. F: 8
    8. TSCA: Yes
    9. HazardClass: 6.1
    10. PackingGroup: II
    11. Hazardous Substances Data: 106-51-4(Hazardous Substances Data)

106-51-4 Usage

Uses

1,4-Benzoquinone is used as a chemical intermediate for the production of various substances, including dyes, fungicides, hydroquinone, rubber accelerators, and oxidizing agents. It is also used in the dye, textile, chemical, tanning, and cosmetic industries. Additionally, it serves as an oxidizing agent, a tanning agent, a photographic chemical, and a reagent.
Used in Chemical Synthesis:
1,4-Benzoquinone is used as a dienophile in Diels-Alder cycloadditions to prepare naphthoquinones and 1,4-phenanthrenediones. It acts as a dehydrogenation reagent and an oxidizer in synthetic organic chemistry. In the Thiele-Winter reaction, it is involved in the preparation of triacetate of hydroxyquinol by reacting with acetic anhydride and sulfuric acid. It is also used in the synthesis of bromadol and to suppress double-bond migration during olefin metathesis reactions.
Used in Photography:
1,4-Benzoquinone is used as a precursor to hydroquinone, which finds application in photography as a reducing agent and an antioxidant in rubber production.
Used in Tanning Industry:
1,4-Benzoquinone is used for tanning hides, making gelatin insoluble, and strengthening animal fibers.
Occupational exposure to 1,4-Benzoquinone may occur in the dye, textile, chemical, tanning, and cosmetic industries. Inhalation exposure to 1,4-Benzoquinone may occur from tobacco smoke.

Preparation

Preparation of Quinone (p-Benzoquinone) from Hydroquinone. Principle: Hydroquinone can be readily oxidized to quinone by using oxidizing agent like potassium dichromate and conc. H2SO4 or KBrO3. Reaction: Procedure: Take 0.5 g hydroquinone and 5 ml distilled water in a beaker (25 ml). Heat on a wire gauze to obtain a clear solution. Take 1 g potassium dichromate (K2Cr2O7) in a conical flask and dissolve in 10 ml water and add 1 ml conc. H2SO4. Shake and cool the conical flask in ice water. To this ice cold solution add hydroquinone solution (prepared above) dropwise over a period of 30 minutes with constant shaking. Do not allow the temperature to rise above 20oC. After complete addition, continue shaking for further 10 minutes. Yellow crystals of quinone separate out. Filter on a Buchner funnel and dry it well. (Note: Do not wash with water as the product is water soluble). Record the practical yield and re-crystallize from ethyl alcohol. Re-crystallization: Dissolve the crude product in minimum amount of ethyl alcohol in a beaker by heating on a water bath. Filter the hot solution and cool the filtrate. The yellow needles of quinone separate out. Filter, dry and record the melting point and TLC (using toluene as a solvent).

Production Methods

Quinone was produced as early as 1838 by oxidation of quinic acid with manganese dioxide. Quinone can be prepared by oxidation starting with aniline or by the oxidation of hydroquinone with bromic acid. More recently, quinone has been made biosynthetically from D-glucose.

Reactions

1,4-Benzoquinone and its derivatives are extensively used in Diels-Alder reactions. A facile tautomerization of alkyl substituted 1,4-benzoquinone to o-quinone methide is the highlight of this cycloaddition.Diels-Alder reaction of 1,4-benzoquinone with thiophene dioxide by Kang et al.

Synthesis Reference(s)

Chemistry Letters, 14, p. 603, 1985The Journal of Organic Chemistry, 48, p. 5160, 1983 DOI: 10.1021/jo00174a003Tetrahedron Letters, 29, p. 677, 1988 DOI: 10.1016/S0040-4039(00)80182-3

Air & Water Reactions

Soluble in water and denser than water. If moist 1,4-Benzoquinone may decompose spontaneously above 140°F. This has occurred in drums, causing over-pressurization.

Reactivity Profile

1,4-Benzoquinone acts as an oxidizing agent .

Hazard

Toxic by inhalation, strong irritant to skin, eyes and mucous membranes. Skin damage. Ques- tionable carcinogen.

Health Hazard

1,4-Benzoquinone is moderately toxic viaingestion and skin contact. It is a mutagen andmay cause cancer. Because of its low vaporpressure, 0.1 torr (at 25°C 77°F), the healthhazard due to inhalation of its vapor is low.However, prolonged exposure may produceeye irritation, and its contact with the eyes can injure the cornea. Contact with the skincan lead to irritation, ulceration, and necrosis.The toxicity of benzoquinone is similarto that of hydroquinone and benzenetriol.Repeated intraperitoneal administration of2 mg/kg/day to rats for 6 weeks produced significantdecreases in red blood cell, bone marrowcounts, and hemoglobin content (Raoet al. 1988). In addition, relative changes inorgan weights and injuries to the liver, thymus,kidney, and spleen were observed. Lauet al. (1988) investigated the correlation oftoxicity with increased glutathione substitutionin 1,4-benzoquinone. With the exceptionof the fully substituted isomer, increased substitutionresulted in enhanced nephrotoxicity.Although the conjugates were more stable tooxidation, the toxicity increased. The oral andintravenous toxicities of this compound in ratsare as follow: LD50 value, oral (rats): 130 mg/kgLD50 value, intravenous (rats): 25 mg/kgThe carcinogenicity of 1,4-benzoquinone inhumans is not reported. However, it is amutagen. It produced tumors in the lungs andskin of mice.

Fire Hazard

Noncombustible solid; ignition can occur after only moderate heating, autoignition temperature 560°C (1040°F); fire-extinguishing agent: water spray. 1,4-Benzoquinone may react violently with strong oxidizers, especially at elevated temperatures.

Safety Profile

Poison by ingestion, subcutaneous, intraperitoneal, and intravenous routes. Questionable carcinogen with experimental tumorigenic data by skin contact. Human mutation data reported. Quinone has a characteristic, irritating odor. Causes severe damage to the skin and mucous membranes by contact with it in the solid state, in solution, or in the form of condensed vapors. Locally, it causes dlscoloration, severe irritation, erythema, swehng, and the formation of papules and vesicles, whereas prolonged contact may lead to necrosis. When the eyes become involved, it causes dangerous disturbances of vision. The moist material self-heats and decomposes exothermically above 60℃. When heated to decomposition it emits acrid smoke and fumes.

Potential Exposure

Due to this compound’s ability to react with certain nitrogen compounds to form colored sub- stances, quinone is widely used in the dye, textile, chemi- cal, tanning, and cosmetic industries. It is used as an industrial chemical; laboratory reagent; and as an interme- diate in chemical synthesis for hydroquinone and other chemicals.

Carcinogenicity

Quinone has been tested for carcinogenicity in mice by skin application or inhalation and in rats by subcutaneous injection. None of these studies were considered sufficient to evaluate carcinogenicity (335, 336). A cancer bioassay of Tribolium-infested flour has been conducted but lack of quantification of quinone and methodological issues make the data difficult to interpret. Quinone has produced negative results in studies designed to examine its ability to promote carcinogenicity. In a liver bioassay, quinone did not increase the formation of GGTpositive foci in the liver. Quinone did not promote induction of stomach or skin tumors in mice dosed with 7,12- dimethylbenzanthracene.

Environmental Fate

Quinone exists in the atmosphere in the gas phase. The dominant atmospheric loss process for quinone is expected to be by reaction with the hydroxyl (OH) radical (reaction with ozone is expected to be slow because of the >C(O) substituent groups). The estimated half-life and lifetime of quinone in the atmosphere due to reaction with the OH radical are w3 and 4 h, respectively. Release of 1,4-benzoquinone to the environment occurs via its effluents during its commercial production and use and in wastewaters from the coal industry. If released to soil, it is likely to leach (estimated Koc of 30) and may volatilize and photodegrade on soil surfaces. The ambient atmospheric concentration of 1,4-benzoquinone has been reported to be less than 15–80 ng m-3, and benzoquinone has been detected in tobacco smoke.

Shipping

UN2587 Benzoquinone, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Purify p-benzoquinone in one or more of the following ways: steam distillation followed by filtration and drying (e.g. in a desiccator over CaCl2), crystallisation from pet ether (b 80-100o), *benzene (with, then without, charcoal), water or 95% EtOH, sublimation under vacuum (e.g. from room temperature to liquid N2). It slowly decomposes and should be stored, refrigerated, in an evacuated or sealed glass vessel in the dark. It should be resublimed before use. [Wolfenden et al. J Am Chem Soc 109 463 1987, Beilstein 7 IV 2065.]

Toxicity evaluation

The acute narcotic effects are due to the physical interaction of quinone itself on the cells of the central nervous system (CNS). The long-term effects are most likely due to the production of an unstable reactive intermediate during biotransformation or redox cycling. Cytochrome P450–mediated xenobiotic metabolism often leads to biological intermediates with attributes identical to quinones.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explo- sions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, some combustible substances; reducing agents. Decomposes exothermically on warming above 60 ? C, when moist, producing carbon monoxide.

Waste Disposal

Controlled incineration (982℃, 2.0 seconds minimum).

Check Digit Verification of cas no

The CAS Registry Mumber 106-51-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 6 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 106-51:
(5*1)+(4*0)+(3*6)+(2*5)+(1*1)=34
34 % 10 = 4
So 106-51-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4H

106-51-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (B0089)  1,4-Benzoquinone  >98.0%(T)

  • 106-51-4

  • 25g

  • 185.00CNY

  • Detail
  • TCI America

  • (B0089)  1,4-Benzoquinone  >98.0%(T)

  • 106-51-4

  • 100g

  • 510.00CNY

  • Detail
  • TCI America

  • (B0089)  1,4-Benzoquinone  >98.0%(T)

  • 106-51-4

  • 500g

  • 1,590.00CNY

  • Detail
  • TCI America

  • (B0887)  1,4-Benzoquinone  >97.0%(T)

  • 106-51-4

  • 25g

  • 130.00CNY

  • Detail
  • TCI America

  • (B0887)  1,4-Benzoquinone  >97.0%(T)

  • 106-51-4

  • 500g

  • 770.00CNY

  • Detail
  • Alfa Aesar

  • (A13162)  p-Benzoquinone, 98+%   

  • 106-51-4

  • 100g

  • 223.0CNY

  • Detail
  • Alfa Aesar

  • (A13162)  p-Benzoquinone, 98+%   

  • 106-51-4

  • 250g

  • 547.0CNY

  • Detail
  • Alfa Aesar

  • (A13162)  p-Benzoquinone, 98+%   

  • 106-51-4

  • 1000g

  • 986.0CNY

  • Detail
  • Alfa Aesar

  • (A13162)  p-Benzoquinone, 98+%   

  • 106-51-4

  • 5000g

  • 4269.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1028)  1,4-Benzoquinone  pharmaceutical secondary standard; traceable to USP

  • 106-51-4

  • PHR1028-1G

  • 732.19CNY

  • Detail
  • Sigma-Aldrich

  • (12309)  p-Benzoquinone  for spectrophotometric det. of amines, ≥99.5% (HPLC)

  • 106-51-4

  • 12309-25G

  • 862.29CNY

  • Detail
  • Sigma-Aldrich

  • (12309)  p-Benzoquinone  for spectrophotometric det. of amines, ≥99.5% (HPLC)

  • 106-51-4

  • 12309-100G

  • 2,818.53CNY

  • Detail

106-51-4SDS

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 1,4-benzoquinone

1.2 Other means of identification

Product number -
Other names 2,5-Cyclohexadiene-1,4-dione

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Quinone is used as a chemical intermediate, a polymerization inhibitor, an oxidizing agent, a photographic chemical, a tanning agent, and a chemical reagent.
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:106-51-4 SDS

106-51-4Synthetic route

4-methoxy-phenol
150-76-5

4-methoxy-phenol

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With bis-[(trifluoroacetoxy)iodo]benzene In water; acetonitrile for 0.166667h; Ambient temperature;100%
With copper(II) nitrate/zeolite H-Y Product distribution; Further Variations:; heating mode; times; microwave irradiation;100%
With manganese dioxide impregnated with nitric acid In dichloromethane for 0.5h; Ambient temperature;96%
hydroquinone
123-31-9

hydroquinone

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With barium ferrate(VI) In benzene for 0.25h; Product distribution; Heating;100%
With benzyltrimethylammonium tribromide; sodium acetate In dichloromethane; water for 2h; Ambient temperature;100%
With bis(2,2'-bipyridyl) copper(II) permanganate In dichloromethane for 0.25h; Ambient temperature;100%
phenol
108-95-2

phenol

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With CuCl2 In acetonitrile100%
With [CuII2(μ-OH)(1,2-bis(2-(bis(2-pyridylmethyl)aminomethyl)-6-pyridyl)ethane)](ClO4)3 ; dihydrogen peroxide; triethylamine In water; acetonitrile at 50℃; for 10h; Catalytic behavior; Inert atmosphere;99%
With manganese(IV) oxide; sulfuric acid; aniline at 10℃; for 1.5h;95%
hydroquinone
123-31-9

hydroquinone

A

diphenyl-2,5 furannedicarbaldehyde 3,4
36831-87-5

diphenyl-2,5 furannedicarbaldehyde 3,4

B

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With barium ferrate(VI) In benzene for 0.3h; Heating;A 70%
B 100%
1,4-dimethoxybezene
150-78-7

1,4-dimethoxybezene

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With bis-[(trifluoroacetoxy)iodo]benzene In methanol; water at 20℃; for 4h;100%
With manganese dioxide impregnated with nitric acid In dichloromethane for 1.5h; Ambient temperature;93%
With Oxone; 4-iodophenoxyacetic acid In 2,2,2-trifluoroethanol; water at 20℃; for 1h;86%
1,4-bis(trimethylsilyloxy)benzene
2117-24-0

1,4-bis(trimethylsilyloxy)benzene

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane at 25℃; for 2h; Mechanism; relative reaction rate;99%
With quinolinium monofluorochromate(VI) In dichloromethane for 1h; Ambient temperature;98%
With dioxochloro(trimethylsiloxy)chromate(VI) In dichloromethane for 0.333333h; Ambient temperature;97%
4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In acetonitrile at 80℃; for 0.75h; Baeyer-Villiger Ketone Oxidation; regioselective reaction;99%
1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With sodium periodate In water at 20℃; for 0.166667h;98%
With [bis(acetoxy)iodo]benzene In acetone at 20℃; for 0.166667h;90%
With sulfuric acid; manganese triacetate In water at 35℃; Rate constant; Mechanism;
With dichromate anion
With manganese(IV) oxide; sulfuric acid
benzamide
55-21-0

benzamide

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With iodobenzene; oxone; water In acetonitrile at 20℃;98%
With sodium hydrogen sulfate; [bis(acetoxy)iodo]benzene In water; acetonitrile at 20℃; for 0.5h; Time; Solvent;80%
4-Ethoxyphenol
622-62-8

4-Ethoxyphenol

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With Oxone; 4-iodophenoxyacetic acid In 2,2,2-trifluoroethanol; water at 20℃; for 0.5h;97%
With bis-[(trifluoroacetoxy)iodo]benzene In water; acetonitrile for 0.166667h; Ambient temperature;93%
With oxone; tetrabutylammomium bromide In water; acetonitrile at 20℃; for 1h;92%
With Oxone In water; acetonitrile at 20℃; for 17h;79%
4-methoxyacetanilide
51-66-1

4-methoxyacetanilide

A

4-methoxy-2-nitroacetanilide
119-81-3

4-methoxy-2-nitroacetanilide

B

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With nitric acid; silica gel In dichloromethane for 0.166667h; Product distribution; Ambient temperature;A 97%
B 2%
1,4-dimethoxybezene
150-78-7

1,4-dimethoxybezene

A

1,4-dimethoxy-2-nitrobenzene
89-39-4

1,4-dimethoxy-2-nitrobenzene

B

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With nitric acid; silica gel In dichloromethane for 0.0833333h; Product distribution; Ambient temperature;A 97%
B 2%
phenol
108-95-2

phenol

A

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

B

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With NO+*18-crown-6*H(NO3)2- In various solvent(s) for 2h; Nitration; Heating;A 94%
B 5%
With Zn(NO3)2*2N2O4 In ethyl acetate at 20℃; for 0.25h;A 86%
B 8%
1,4-diethoxybenzene
122-95-2

1,4-diethoxybenzene

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With Oxone; 4-iodophenoxyacetic acid In 2,2,2-trifluoroethanol; water at 20℃; for 1h;94%
With oxone; 4-iodophenoxyacetic acid In 2,2,2-trifluoroethanol; water at 20℃; for 1h;94%
With ammonium cerium(IV) nitrate In water; acetonitrile at 20℃;66%
C24H23NO5

C24H23NO5

A

C17H17NO4

C17H17NO4

B

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With cerium(IV) ammonium nitrate; silica gel In water; acetonitrile at 20℃;A 94%
B n/a
4-(tert-butyldimethylsilyloxy)anisole
62790-87-8

4-(tert-butyldimethylsilyloxy)anisole

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With oxone; 4-iodophenoxyacetic acid In 2,2,2-trifluoroethanol; water at 20℃; for 1.5h;94%
With Oxone; 4-iodophenoxyacetic acid In 2,2,2-trifluoroethanol; water at 20℃; for 1.5h;79%
4-methoxyphenylacetamide
3424-93-9

4-methoxyphenylacetamide

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With iodobenzene; oxone; water In acetonitrile at 20℃;94%
With sodium hydrogen sulfate; [bis(acetoxy)iodo]benzene In water; acetonitrile at 20℃; for 0.666667h;75%
benzene
71-43-2

benzene

A

p-benzoquinone
106-51-4

p-benzoquinone

B

phenol
108-95-2

phenol

Conditions
ConditionsYield
With [CuII2(μ-OH)(1,2-bis(2-(bis(2-pyridylmethyl)aminomethyl)-6-pyridyl)ethane)](ClO4)3 ; dihydrogen peroxide; triethylamine In water; acetonitrile at 50℃; for 40h; Catalytic behavior; Inert atmosphere;A 6.8%
B 93.2%
With dihydrogen peroxide In water for 0.25h; Reagent/catalyst; Irradiation;A n/a
B 81.5%
With tetrakis(acetonitrile)copper(I) perchlorate; dihydrogen peroxide In water; acetonitrile at 25℃; for 4h; Catalytic behavior; Reagent/catalyst;A 60%
B n/a
4-amino-phenol
123-30-8

4-amino-phenol

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With K10 montmorillonite; iodic acid for 0.00833333h; microwave irradiation;93%
With Montmorillonite K10; iodic acid at 68℃; for 0.00555556h; microwave irradiation;85%
With pyridine hydrogenfluoride; sodium nitrite Product distribution; Mechanism; other substrates, various temp.;80%
C25H23NO3

C25H23NO3

A

C17H15NO2

C17H15NO2

B

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With cerium(IV) ammonium nitrate; silica gel In water; acetonitrile at 20℃;A 93%
B n/a
N-phenylsulphonyl-Se,Se-diphenylselenimide
52867-18-2

N-phenylsulphonyl-Se,Se-diphenylselenimide

hydroquinone
123-31-9

hydroquinone

A

benzenesulfonamide
98-10-2

benzenesulfonamide

B

diphenylselenide
1132-39-4

diphenylselenide

C

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
In toluene for 25h; Product distribution; Heating; other N-sulfonylchalcogenimides, other quinones, var. solvent and time;A 92%
B 87%
C 89%
4-n-butoxyphenol
122-94-1

4-n-butoxyphenol

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With oxone; tetrabutylammomium bromide In water; acetonitrile at 20℃; for 1h;92%
With Oxone; 4-iodophenoxyacetic acid In 2,2,2-trifluoroethanol; water at 20℃; for 0.5h;88%
With Oxone In water; acetonitrile at 20℃; for 17h;77%
C28H23NO4

C28H23NO4

A

C20H15NO3

C20H15NO3

B

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With cerium(IV) ammonium nitrate; silica gel In water; acetonitrile at 20℃;A 91%
B n/a
C23H18Cl2N2O5

C23H18Cl2N2O5

A

3-(2,4-dichlorophenoxy)-4-(4-nitrophenyl)azetidin-2-one

3-(2,4-dichlorophenoxy)-4-(4-nitrophenyl)azetidin-2-one

B

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With cerium(IV) ammonium nitrate; silica gel In water; acetonitrile at 20℃;A 91%
B n/a
C27H22N2O8

C27H22N2O8

A

C20H16N2O7

C20H16N2O7

B

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With cerium(IV) ammonium nitrate; silica gel In dichloromethane at 20℃;A 90%
B n/a
1-(4-(benzyloxy)phenyl)-3-hydroxy-2-phenoxypropan-1-one

1-(4-(benzyloxy)phenyl)-3-hydroxy-2-phenoxypropan-1-one

A

4-Benzyloxyphenol
103-16-2

4-Benzyloxyphenol

B

4-(benzyloxy)phenyl 3-hydroxy-2-phenoxypropanoate

4-(benzyloxy)phenyl 3-hydroxy-2-phenoxypropanoate

C

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With methanesulfonic acid; dihydrogen peroxide In water; acetonitrile at 50℃; for 6h; Flow reactor; Green chemistry;A 1%
B 8%
C 90%
C23H19NO5

C23H19NO5

4-(benzo[d][1,3]dioxol-5-yl)-3-phenoxyazetidin-2-one

4-(benzo[d][1,3]dioxol-5-yl)-3-phenoxyazetidin-2-one

B

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With ceric(IV) tetra-n-butylammonium nitrate; water In dichloromethane at 20℃; for 0.333333h; Reagent/catalyst; Solvent; Temperature;A 89%
B n/a
1-(4-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one
92409-23-9

1-(4-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one

A

4-methoxyphenyl 3-hydroxy-2-(2-methoxyphenoxy)propanoate

4-methoxyphenyl 3-hydroxy-2-(2-methoxyphenoxy)propanoate

B

4-methoxy-phenol
150-76-5

4-methoxy-phenol

C

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With methanesulfonic acid; dihydrogen peroxide In water; acetonitrile at 50℃; for 6h; Flow reactor; Green chemistry;A 9%
B 2%
C 89%
acetic anhydride
108-24-7

acetic anhydride

p-benzoquinone
106-51-4

p-benzoquinone

1,2,4-triacetoxybenzene
613-03-6

1,2,4-triacetoxybenzene

Conditions
ConditionsYield
With sulfuric acid at 40 - 50℃;100%
With sulfuric acid at 10 - 45℃; for 1h;97.4%
With sulfuric acid at 25 - 50℃; for 0.5h; Reagent/catalyst; Temperature;96%
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

p-benzoquinone
106-51-4

p-benzoquinone

norbornenoquinone
51175-59-8

norbornenoquinone

Conditions
ConditionsYield
In hexane; ethyl acetate at 0℃; for 3.5h; Diels-Alder Cycloaddition;100%
In methanol at -78 - 0℃; Inert atmosphere; optical yield given as %de;98%
In hexane; ethyl acetate at 0℃; for 4h; Diels-Alder reaction;97%
p-benzoquinone
106-51-4

p-benzoquinone

5,6-dichlorocyclohex-2-ene-1,4-dione
5273-62-1

5,6-dichlorocyclohex-2-ene-1,4-dione

Conditions
ConditionsYield
With sulfuryl dichloride; triethylamine In diethyl ether for 0.5h;100%
With chloroform; chlorine
With sulfuryl dichloride
p-benzoquinone
106-51-4

p-benzoquinone

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With nickel In tetrahydrofuran at 20℃; for 0.166667h; Reduction;100%
With boron trifluoride diethyl etherate; sodium iodide In acetonitrile at 0℃; for 0.0833333h;99%
With hydrazine hydrate In acetonitrile at 20℃; for 18h; Irradiation;99%
sulfure de pentamethylene
1613-51-0

sulfure de pentamethylene

p-benzoquinone
106-51-4

p-benzoquinone

2,5-dihydroxyphenylthianium perchlorate

2,5-dihydroxyphenylthianium perchlorate

Conditions
ConditionsYield
With perchloric acid In acetone at 0℃;100%
sulfure de pentamethylene
1613-51-0

sulfure de pentamethylene

p-benzoquinone
106-51-4

p-benzoquinone

1-(2,5-dihydroxyphenyl)thianium bromide
89706-15-0

1-(2,5-dihydroxyphenyl)thianium bromide

Conditions
ConditionsYield
With hydrogen bromide In acetone at 0℃;100%
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

p-benzoquinone
106-51-4

p-benzoquinone

1α,4α,4aβ,10aα,5β,8β,8aα,9aβ-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione
78548-82-0

1α,4α,4aβ,10aα,5β,8β,8aα,9aβ-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione

Conditions
ConditionsYield
In benzene at 40℃; for 20h;100%
In dichloromethane at 20℃; for 24h; Diels-Alder reaction;100%
In ethanol at 0℃; for 0.5h; Diels-Alder Cycloaddition;98%
thiophenol
108-98-5

thiophenol

p-benzoquinone
106-51-4

p-benzoquinone

2-(phenylthio)benzene-1,4-diol
18231-96-4

2-(phenylthio)benzene-1,4-diol

Conditions
ConditionsYield
In methanol100%
With methanol at 20℃; for 6h;99%
In methanol for 0.166667h; Ambient temperature;95%
Diphenylphosphine oxide
4559-70-0

Diphenylphosphine oxide

p-benzoquinone
106-51-4

p-benzoquinone

(2,5-dihydroxyphenyl)diphenylphosphine oxide
13291-46-8

(2,5-dihydroxyphenyl)diphenylphosphine oxide

Conditions
ConditionsYield
In toluene for 1.66667h;100%
With water In toluene at 80℃; for 12h; Inert atmosphere; Schlenk technique;98%
In toluene for 20h; Inert atmosphere; Reflux;88.1%
In toluene at 75 - 110℃; for 1h; Michael Addition; Inert atmosphere;86%
In toluene
9,10-dimethylanthracene
781-43-1

9,10-dimethylanthracene

p-benzoquinone
106-51-4

p-benzoquinone

9,10-Dimethyl-12,15-dioxo-11,12,15,16-tetrahydro-triptycen
115163-71-8

9,10-Dimethyl-12,15-dioxo-11,12,15,16-tetrahydro-triptycen

Conditions
ConditionsYield
With magnesium(II) perchlorate In acetonitrile at 24.9℃; dependence of kobs on ;100%
With magnesium(II) perchlorate In acetonitrile100%
In chloroform-d1 at 24.85℃; Quantum yield;65%
With p-benzoquinone*2thymol eutectic for 0.5h; Diels-Alder reaction;95 % Spectr.
With magnesium(II) perchlorate In [D3]acetonitrile at 24.84℃; Kinetics; Further Variations:; Reagents; Diels-Alder reaction;
diphenyl phosphorohydrazidate
33862-44-1

diphenyl phosphorohydrazidate

p-benzoquinone
106-51-4

p-benzoquinone

C18H15N2O4P

C18H15N2O4P

Conditions
ConditionsYield
In benzene at 25℃;100%
cis-3-thiabicyclo<3.3.1>nonane
20742-48-7

cis-3-thiabicyclo<3.3.1>nonane

p-benzoquinone
106-51-4

p-benzoquinone

(1R,5S)-3-(2,5-Dihydroxy-phenyl)-3-thionia-bicyclo[3.3.1]nonane; hydrogen sulfate

(1R,5S)-3-(2,5-Dihydroxy-phenyl)-3-thionia-bicyclo[3.3.1]nonane; hydrogen sulfate

Conditions
ConditionsYield
With sulfuric acid In acetone at 0℃;100%
(E)-8-Nitro-octa-1,3-diene
88888-43-1

(E)-8-Nitro-octa-1,3-diene

p-benzoquinone
106-51-4

p-benzoquinone

(4aR,5R,8aS)-5-(4-Nitro-butyl)-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone

(4aR,5R,8aS)-5-(4-Nitro-butyl)-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone

Conditions
ConditionsYield
In toluene at 110℃; for 15h;100%
p-benzoquinone
106-51-4

p-benzoquinone

1,4-Cyclohexanedione
637-88-7

1,4-Cyclohexanedione

Conditions
ConditionsYield
With aluminium trichloride; zinc In tetrahydrofuran for 0.4h; Ambient temperature;100%
With formic acid In toluene at 120℃; for 10h; Inert atmosphere; chemoselective reaction;57%
With hydrogen; tetra-(n-butyl)ammonium iodide In water at 110℃; under 15001.5 Torr; for 24h; chemoselective reaction;57%
With ruthenium; hydrogen at 80℃; under 37503.8 Torr; for 1h; Reagent/catalyst; Ionic liquid; chemoselective reaction;
phenyltellurotrimethylsilane
73296-31-8

phenyltellurotrimethylsilane

p-benzoquinone
106-51-4

p-benzoquinone

1,4-bis(trimethylsilyloxy)benzene
2117-24-0

1,4-bis(trimethylsilyloxy)benzene

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.5h; reductive silylation;100%
p-benzoquinone
106-51-4

p-benzoquinone

(E,E)-2-pyridyldimethyl(buta-1,3-dienyl)silane
270589-03-2

(E,E)-2-pyridyldimethyl(buta-1,3-dienyl)silane

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃; for 38h;100%
With hydrogenchloride In water at 20℃; for 38h; Product distribution; Further Variations:; Reagents; Solvents; Diels-Alder reaction;100%
p-benzoquinone
106-51-4

p-benzoquinone

(E,E)-2-pyridyldimethyl(3-methylbuta-1,3-dienyl)silane
270589-04-3

(E,E)-2-pyridyldimethyl(3-methylbuta-1,3-dienyl)silane

6-methyl-1,4-naphthoquinone
605-93-6

6-methyl-1,4-naphthoquinone

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃; for 38h;100%
With hydrogenchloride In water at 20℃; for 38h; Diels-Alder reaction;100%
tetrafluoroboric acid

tetrafluoroboric acid

1,1'-diacetylferrocene
1273-94-5

1,1'-diacetylferrocene

p-benzoquinone
106-51-4

p-benzoquinone

1,1'-diacetylferriceniumtetra-fluoroborate

1,1'-diacetylferriceniumtetra-fluoroborate

Conditions
ConditionsYield
In diethyl ether; chloroform Dropwise addn. (Ar) of ferrocene complex in dry chloroform to org. compd. in the presence of HBF4 (Et2O) at -10°C, and stirring (1 h, room temp.) of resulting soln.; Isolation of resulting compd. by filtn. and silica gel chromy.;100%
1,3-bis(trimethylsilyl)-1,3-diaza-2-germa(II)indane
117226-57-0

1,3-bis(trimethylsilyl)-1,3-diaza-2-germa(II)indane

p-benzoquinone
106-51-4

p-benzoquinone

2C6H4(N(Si(CH3)3))2(2-)*2Ge(3+)*(OC6H4O)(2-)

2C6H4(N(Si(CH3)3))2(2-)*2Ge(3+)*(OC6H4O)(2-)

Conditions
ConditionsYield
In toluene monomer feed ratio germylene : p-benzoquinone = 4.0 : 1.0, at -78°C under Ar for 1 h; elem. anal.;100%
In tetrahydrofuran monomer feed ratio germylene : p-benzoquinone = 2.0 : 1.0, at -78°C under Ar for 1 h; elem. anal.;96%
In toluene monomer feed ratio germylene : p-benzoquinone = 2.0 : 1.0, at -78°C under Ar for 1 h; elem. anal.;91%
In toluene monomer feed ratio germylene : p-benzoquinone = 1.0 : 1.0, at -78°C under Ar for 1 h; elem. anal.;86%
bis(β-dimethylaminoethoxy)tin

bis(β-dimethylaminoethoxy)tin

p-benzoquinone
106-51-4

p-benzoquinone

Sn(OCH2CH2N(CH3)2)2(OC6H4O)

Sn(OCH2CH2N(CH3)2)2(OC6H4O)

Conditions
ConditionsYield
In benzene under N2, soln. of C6H4O2 in benzene added to Sn compd. in benzene at 22-24°C, refluxed with stirring for 2 h; ppt. filtered off, washed with benzene, dried; elem. anal.;100%
bis[bis(trimethylsilyl)amino]germanium(II)
59863-12-6

bis[bis(trimethylsilyl)amino]germanium(II)

p-benzoquinone
106-51-4

p-benzoquinone

Ge(N(Si(CH3)3)2)2OC6H4O

Ge(N(Si(CH3)3)2)2OC6H4O

Conditions
ConditionsYield
In benzene (Ar); stirring (1 h, 25°C); soln. filtn. off, drying (vac.);100%
In toluene (Ar); stirring (1 h, -78, 0 or 50°C); soln. filtn. off, drying (vac.); elem. anal.;100%
In diethyl ether (Ar); stirring (1 h, 0°C); soln. filtn. off, drying (vac.);99%
tetrakis(triphenylphosphine) palladium(0)
14221-01-3

tetrakis(triphenylphosphine) palladium(0)

p-benzoquinone
106-51-4

p-benzoquinone

[palladium(0)(triphenylphosphine)2(p-benzoquinone)]
490039-51-5, 57036-58-5

[palladium(0)(triphenylphosphine)2(p-benzoquinone)]

Conditions
ConditionsYield
In benzene under N2 atm. to suspn. Pd(PPh3)4 in benzene was added soln. benzoquinone in benzene and stirred for 30 min; soln. was concd., ether-hexane was added;100%
pine pitch

pine pitch

p-benzoquinone
106-51-4

p-benzoquinone

(4aR,4bS,7R,10aR,10bS,12R,12aR)-13-isopropyl-7,10a-dimethyl-1,4-dioxo-4,4a,5,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-4b,12-ethenochrysene-7-carboxylic acid

(4aR,4bS,7R,10aR,10bS,12R,12aR)-13-isopropyl-7,10a-dimethyl-1,4-dioxo-4,4a,5,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-4b,12-ethenochrysene-7-carboxylic acid

Conditions
ConditionsYield
With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In hexane; benzene at 20℃; for 1h; Reactivity; Reagent/catalyst; Solvent; Darkness;100%
3,4-di-tert-butyl-2,5-dimethylthiophene 1-oxide
1243058-70-9

3,4-di-tert-butyl-2,5-dimethylthiophene 1-oxide

p-benzoquinone
106-51-4

p-benzoquinone

C20H28O3S

C20H28O3S

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.0833333h; Diels-Alder reaction;100%
2-bromothiophenol
6320-02-1

2-bromothiophenol

p-benzoquinone
106-51-4

p-benzoquinone

2-((2-bromophenyl)thio)benzene-1,4-diol
1310712-82-3

2-((2-bromophenyl)thio)benzene-1,4-diol

Conditions
ConditionsYield
In methanol100%
With methanol at 20℃; for 6h;93%

106-51-4Related news

Synthesis of 2-substituted hydroquinone derivatives from 1,4-Benzoquinone (cas 106-51-4) and allyl ethers08/21/2019

B-Alkylpinacolboranes, derived from rhodium-catalyzed hydroboration of allyl ethers with pinacolborane, react with 1,4-benzoquinone under acidic, oxidizing conditions, to afford, after subsequent hydrogenation, 2-substituted hydroquinones in isolated, purified yields of about 50% based on 1,4-be...detailed

106-51-4Relevant articles and documents

Effect of calcination temperature on the structure and catalytic performance of copper-ceria mixed oxide catalysts in phenol hydroxylation

Amadine, Othmane,Essamlali, Younes,Fihri, Aziz,Larzek, Mohamed,Zahouily, Mohamed

, p. 12586 - 12597 (2017)

We report on highly active CuO@CeO2 catalysts prepared by the surfactant-template method and calcined at different temperatures. Then the obtained catalysts were characterized by means of various analytical techniques. Our findings show that the BET surface area and pore volume of the CuO@CeO2 catalyst measured by N2 adsorption-desorption are decreasing with the elevation of calcination temperature. From the results of XRD and XPS, we determined the oxidation state of copper in the copper-ceria mixed oxide catalysts. The CuO@CeO2 catalysts displayed good catalytic activity for the phenol hydroxylation using H2O2 as an oxidant. Moreover, we found that the catalytic activity is improved for high calcining temperature and the optimum conditions were obtained when the catalyst CuO@CeO2 is calcined at 800 °C, which lead to higher phenol conversion of 54.62% with 92.87% of selectivity for catechol and hydroquinone. More importantly, the catalyst seems to be easily recovered by simple centrifugation. The results of catalyst recycling illustrated that the catalytic activity remained high even after five cycles with slight Cu leaching and slight loss of activity. Finally, a possible mechanism in phenol hydroxylation by H2O2 over CuO@CeO2 catalyst was also proposed.

Oxidation of Electron-Rich Arenes Using HFIP-UHP System

Llopis, Natalia,Baeza, Alejandro

, p. 6159 - 6164 (2020)

The straightforward oxidation of electron-rich arenes, namely, phenols, naphthols, and anisole derivatives, under mild reaction conditions, is described by means of the use of an environmentally benign HFIP-UHP system. The corresponding quinones or hydroxylated arenes were obtained in moderate to good yields.

Nitrogen Dioxide and Related Free Radicals: Electron-transfer Reactions with Organic Compounds in Solutions containing Nitrite or Nitrate

Forni, Luigi G.,Mora-Arellano, Victor O.,Packer, John E.,Willson, Robin L.

, p. 1 - 6 (1986)

The absolute rate constants for the reaction of NO32-. (formed by one-electron reduction of nitrate) with oxygen, benzoquinone, and methyl viologen have been determined by pulse radiolysis.Experiments have shown that such reactions can occur in competition with the hydrolysis reaction leading to NO2. and that the formation of the latter can be catalysed by the presence of hydrogen or ammonium ions.Absolute rate constants for the oxidation of the phenothiazine derivative metiazinic acid, of 2,2'-azinobis-(3-ethyl-2,3-dihydrobenzothiazole-6-sulphonate), of ascorbate, and of dihydroxyfumarate by NO2. have also been measured.

Improving removal of 4-chlorophenol using a TiO2 photocatalytic system with microwave and ultraviolet radiation

Ki, Seo Jin,Jeon, Ki-Joon,Park, Young-Kwon,Jeong, Sangmin,Lee, Heon,Jung, Sang-Chul

, p. 15 - 22 (2017)

A conventional photocatalytic system is a viable tool to purify wastewaters, whereas poor degradation performance due to diverse pollutants under various conditions still leaves it behind commercial markets. This study aimed to determine the degradation e

Synthesis of Cu2 (OH)PO4 crystals with various morphologies and their catalytic activity in hydroxylation of phenol

Fu, Weiwei,Wang, Runwei,Wu, Lele,Wang, Hongbin,Wang, Xu,Wang, Aijing,Zhang, Zongtao,Qiu, Shilun

, p. 772 - 774 (2013)

Copper hydroxyphosphate (Cu2(OH)PO4) crystals with various morphologies have been successfully synthesized by a simple hydrothermal method, using different organic amines as the morphology-controlling agents. These Cu2(OH)PO4 crystals were used as catalysts for phenol hydroxylation by H2O2, and they showed distinct activities. The sheet morphology of Cu2(OH)PO4 crystals with a large percentage of reactive facets ({011} facets) exhibited enhanced catalytic activity in hydroxylation of phenol.

Preparation and photocatalytic performance of silver-modified and nitrogen-doped TiO2nanomaterials with oxygen vacancies

Zhang, Hong,Jiang, Yingyu,Zhou, Baiqin,Wei, Zhuo,Zhu, Zhenya,Han, Lijuan,Zhang, Ping,Hu, Yingying

, p. 4694 - 4704 (2021)

The photocatalysis of titanium dioxide (TiO2) exerts excellent degradation performance against contaminants in the environment. However, it prefers to absorb ultraviolet light rather than visible light, which significantly constrains its widespread use under visible light. Here, we prepared oxygen vacancy-containing TiO2viaAg-modification and N-doping. The utilization of visible light for phenol degradation was significantly enhanced by Ag/N co-doping. The characterization results showed a shuttle-like material coupled with multiple oxygen vacancies, and a well-designed experiment demonstrated that the Ti?:?N?:?Ag ratio of 1?:?0.45?:?0.32 presented optimal performance for phenol degradation. The batch experiment results also proved the modified TiO2as a potent photocatalyst against phenol degradation with an 80.8% degradation efficiency within 5 hours under visible light and with a 99.3% degradation efficiency within 2 hours under ultraviolet light. What is more, we also demonstrated that hydroxyl radical was the mainly effective radical in the mineralization of phenol and put forward a possible degradation pathway based on the observed intermediates. Lastly, the cycling tests indicated that the proposed photocatalyst is durable with a fair phenol degradation ability after recycling 5 times.

The photochemistry of 4-chlorophenol in water revisited: The effect of cyclodextrins on cation and carbene reactions

Manet, Ilse,Monti, Sandra,Bortolus, Pietro,Fagnoni, Maurizio,Albini, Angelo

, p. 4274 - 4282 (2005)

The photochemistry of 4-chlorophenol (1) in water and in the presence of cyclodextrins has been studied by means of steady-state and time-resolved experiments. These have shown that 1 undergoes photoheterolysis of the C-Cl bond in the triplet state to yield the 4-hydroxyphenyl cation 32 in equilibrium with 4-oxocyclohexa-2,5-dienylidene, 33. These triplet intermediates scarcely react with a n nucleophile, such as water, nor abstract hydrogen from this solvent, thus they are long-lived (≈1 μs). Specific trapping of both intermediates has been achieved. The cation adds to 2-propenol, kadd~1.3× 108 M-1 s-1, to form the long-lived phenonium ion 11 (with λmax = 290 nm), which then converts to 3-(4-hydroxyphenyl)propane-1,2-diol (10). Carbene 33 is trapped by oxygen to give benzoquinone and is reduced by D-glucose (kq = 8.5 × 10-1 s-1) to give the phenoxyl radical (8) and phenol (9). Cyclodextrins have been found to trap the intermediates much more efficiently (kq = 9.4×10 8M-1s-1 with β-CD), which indicates that inclusion is involved. Ground state 1 forms inclusion complexes with 1:1 stoichiometry and association constants of 140 and 300 M-1 with α- and β-CD, respectively. Complexation does not change the efficiency or the mode of photofragmentation of 1; however, it does influence the course of the reaction because the major portion of the intermediates are reduced to phenol within the cavity (k′red ≥ 5 × 107 s-1) either via a radical 8 or via a radical cation 9+. Under these conditions, neither 2-propenol nor oxygen trap the intermediates to a significant extent.

Effective photodegradation of organic pollutantsin the presence of mono and bi-metallic complexes under visible-light irradiation

Chetti, Prabhakar,Gade, Ramesh,Guguloth, Venkanna,Pola, Someshwar,Ravulapelly, Koteshwar Rao,Subburu, Mahesh

, (2021)

The synthesis of new mono and bi-metallic complexes such as Zn (II) and Ag-Zn (II) complexes with organic functional group-based ligand (OFL) presented in the current work along with the exploration of their applicability in the photocatalytic degradation

Peroxomonophosphoric Acid Oxidation. 7. Studies of the Kinetics and Substituent Effect in the Oxidation of Aniline

Panda, Abhina K.,Mahapatro, Surendra N.,Panigrahi, Ganesh P.

, p. 4000 - 4004 (1981)

The kinetics of the oxidation of aniline and 12 substituted anilines by peroxomonophosphoric acid (PMPA) have been measured.The reactions are first order in PMPA and first order in amine.The rate laws are given in eq 10 and 13.The unprotonated amine is the reactive species.Correlation of log rates with ?, ?+, ?-, and ΔpKa yielded values of ρ (-1.37), ρ+ (-1.31); ρ- (-1.38), and β (0.58), respectively.The values suggest an electron-deficient reaction center, and the Bronsted coefficient, β, indicates considerable bond formation in the transition state.All the ortho substituents provide steric retardation for the formation of the transition state.Oxidation of aniline gives azobenzene, azoxybenzene, p-aminophenol, and p-benzoquinone routed through the reactive intermediate phenylhydroxylamine.The individual reactivities of various ionized PMPA species with the amine have been estimated.

Two-Dimensional Layered Zinc Silicate Nanosheets with Excellent Photocatalytic Performance for Organic Pollutant Degradation and CO2 Conversion

Wang, Lan,Bahnemann, Detlef W.,Bian, Liang,Dong, Guohui,Zhao, Jie,Wang, Chuanyi

, p. 8103 - 8108 (2019)

Two-dimensional (2D) photocatalysts are highly attractive for their great potential in environmental remediation and energy conversion. Herein, we report a novel layered zinc silicate (LZS) photocatalyst synthesized by a liquid-phase epitaxial growth route using silica derived from vermiculite, a layered silicate clay mineral, as both the lattice-matched substrate and Si source. The epitaxial growth of LZS is limited in the 2D directions, thus generating the vermiculite-type crystal structure and ultrathin nanosheet morphology with thicknesses of 8–15 nm and a lateral size of about 200 nm. Experimental observations and DFT calculations indicated that LZS has a superior band alignment for the degradation of organic pollutants and reduction of CO2 to CO. The material exhibited efficient photocatalytic performance for 4-chlorophenol (4-CP) degradation and CO2 conversion into CO and is the first example of a claylike 2D photocatalyst with strong photooxidation and photoreduction capabilities.

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