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1016-05-3 Usage

Chemical Properties

white to yellow crystalline powder

Definition

ChEBI: A sulfone resulting from the oxidation of the sulfur atom of dibenzothiophene.

Synthesis Reference(s)

Tetrahedron Letters, 17, p. 785, 1976 DOI: 10.1016/S0040-4039(00)77951-2

Check Digit Verification of cas no

The CAS Registry Mumber 1016-05-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,1 and 6 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1016-05:
(6*1)+(5*0)+(4*1)+(3*6)+(2*0)+(1*5)=33
33 % 10 = 3
So 1016-05-3 is a valid CAS Registry Number.
InChI:InChI=1/C12H8O2S/c13-15(14)11-7-3-1-5-9(11)10-6-2-4-8-12(10)15/h1-8H

1016-05-3 Well-known Company Product Price

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  • Detail
  • TCI America

  • (D4153)  Dibenzothiophene 5,5-Dioxide  >98.0%(GC)

  • 1016-05-3

  • 5g

  • 440.00CNY

  • Detail
  • TCI America

  • (D4153)  Dibenzothiophene 5,5-Dioxide  >98.0%(GC)

  • 1016-05-3

  • 25g

  • 1,540.00CNY

  • Detail
  • Aldrich

  • (D32407)  Dibenzothiophenesulfone  97%

  • 1016-05-3

  • D32407-5G

  • 668.07CNY

  • Detail
  • Aldrich

  • (D32407)  Dibenzothiophenesulfone  97%

  • 1016-05-3

  • D32407-25G

  • 2,230.02CNY

  • Detail

1016-05-3SDS

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 Dibenzothiophene 5,5-Dioxide

1.2 Other means of identification

Product number -
Other names Dibenzo[b,d]thiophene 5,5-dioxide

1.3 Recommended use of the chemical and restrictions on use

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

1.4 Supplier's details

1.5 Emergency phone number

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

More Details:1016-05-3 SDS

1016-05-3Synthetic route

dibenzothiophene
132-65-0

dibenzothiophene

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
With potassium peroxomonosulfate; cobalt-sulfophtalocyanine In water; acetonitrile at 20℃; for 3h; Product distribution; Further Variations:; Catalysts; reaction time;100%
With sodium periodate In water; acetonitrile for 0.25h; Sonication;100%
With 12-tungstophosphoric acid; hexakis(benzylamino)cyclotriphosphazene; dihydrogen peroxide In water; toluene at 25℃; for 0.5h; Catalytic behavior; Kinetics; Reagent/catalyst; Temperature; Concentration; Green chemistry;100%
butyl sulfoxide
2168-93-6

butyl sulfoxide

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
With iodosylbenzene In ethanol at 20℃; Inert atmosphere;100%
[1,1′-biphenyl]-2-sulfonyl azide
40182-14-7

[1,1′-biphenyl]-2-sulfonyl azide

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane at 25℃; for 3h; regiospecific reaction;99%
dibenzothiophene
132-65-0

dibenzothiophene

A

Dibenzothiophene sulfoxide
1013-23-6

Dibenzothiophene sulfoxide

B

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
With sodium hypochlorite pentahydrate; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water; acetonitrile at 20℃; for 0.4h; Green chemistry;A 86%
B 6%
With peroxygenase; dihydrogen peroxide In acetonitrile at 20℃; for 0.416667h; pH=5; Concentration; Enzymatic reaction;A 86%
B 7.2%
With tert.-butylhydroperoxide In octane at 59.84℃; for 0.5h; Catalytic behavior; Reagent/catalyst;A 18.8%
B 81.2%
[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate
189999-35-7

[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
With sodium metabisulfite; potassium phosphate; 1,10-Phenanthroline; tetrabutylammomium bromide; copper(II) bis(trifluoromethanesulfonate) In dimethyl sulfoxide at 120℃; for 10h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique;82%
1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate
189999-35-7

[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate

A

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

B

2-(2,2-diphenylvinyl)-2'-iodo-1,1'-biphenyl

2-(2,2-diphenylvinyl)-2'-iodo-1,1'-biphenyl

Conditions
ConditionsYield
With sodium metabisulfite; potassium phosphate; 1,10-Phenanthroline; tetrabutylammomium bromide; copper(II) bis(trifluoromethanesulfonate) In dimethyl sulfoxide at 120℃; for 10h; Inert atmosphere; Schlenk technique;A 68%
B 13%
dibenz<1,2>oxathiin 6-oxide
77123-91-2

dibenz<1,2>oxathiin 6-oxide

A

dibenzofuran
132-64-9

dibenzofuran

B

dibenzothiophene
132-65-0

dibenzothiophene

C

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
at 900℃; for 2.77778E-07h; Product distribution; other temp. (700 deg C);A 63%
B 8%
C n/a
dibenzothiophene
132-65-0

dibenzothiophene

A

dibenz<1,2>oxathiin 6,6-dioxide
4371-25-9

dibenz<1,2>oxathiin 6,6-dioxide

B

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

C

2-(2'-hydroxybiphenyl)sulfonate

2-(2'-hydroxybiphenyl)sulfonate

Conditions
ConditionsYield
With dihydrogen peroxide; Fe-sulfophtalocyanine In water; acetonitrile at 20℃; for 6h; Product distribution; Further Variations:; Catalysts; reaction time;A 2%
B 62%
C 36%
1-aminomorpholine
4319-49-7

1-aminomorpholine

[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate
189999-35-7

[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate

A

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

B

2'-iodo-N-morpholino-[1,1'-biphenyl]-2-sulfonamide

2'-iodo-N-morpholino-[1,1'-biphenyl]-2-sulfonamide

Conditions
ConditionsYield
With sodium metabisulfite; potassium phosphate; 1,10-Phenanthroline; 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate; tetrabutylammomium bromide; copper(II) bis(trifluoromethanesulfonate) In dimethyl sulfoxide at 80℃; for 4h; Inert atmosphere;A 18%
B 46%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

diethyl ether
60-29-7

diethyl ether

thianthrene-5,5,10-trioxide
2362-54-1

thianthrene-5,5,10-trioxide

A

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

B

2,2'-sulfinatodibenzoate
22219-00-7

2,2'-sulfinatodibenzoate

Conditions
ConditionsYield
at -70℃; Anschliessend mit festem Kohlendioxid behandeln;
2-phenylbenzenesulfonyl chloride
2688-90-6

2-phenylbenzenesulfonyl chloride

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
With carbon disulfide; aluminium trichloride
With aluminium trichloride; 1,1,2,2-tetrachloroethane
3,7-dibenzothiophenediamine, 5,5-dioxide
6259-19-4

3,7-dibenzothiophenediamine, 5,5-dioxide

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
With hydrogenchloride; ethanol; sodium nitrite
thianthrene-5,5,10,10-tetraoxide
2362-55-2

thianthrene-5,5,10,10-tetraoxide

A

Dibenzotellurophen
244-98-4

Dibenzotellurophen

B

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
With hydrogen telluride; carbon dioxide at 450℃;
2-aminophenyl phenyl sulfone
4273-98-7

2-aminophenyl phenyl sulfone

urea
57-13-6

urea

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
With hydrogenchloride; acetic acid; sodium nitrite anschliessend mit Kupfer behandeln;
dibenzothiophene
132-65-0

dibenzothiophene

trifluoroacetyl peroxide
359-48-8

trifluoroacetyl peroxide

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
100 % Chromat.
Dibenzothiophene sulfoxide
1013-23-6

Dibenzothiophene sulfoxide

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
With water; chlorine In acetic acid at 25℃; Mechanism; Rate constant;
With [bis(acetoxy)iodo]benzene; water; perchloric acid In acetic acid at 49.9℃; Thermodynamic data; Mechanism; Rate constant; ΔH(excit.), ΔS(excit.);
With molybdenum peroxide hexamethylphosphorylamide In 1,2-dichloro-ethane at 40℃; Rate constant;
1,2-bis(phenylsulphonyl)benzene
102059-02-9

1,2-bis(phenylsulphonyl)benzene

A

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

B

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
With tetrabutylammonium acetate In dimethyl sulfoxide controlled-potential electrolysis; 0.1M tetrabutylammonium tetrafluoroborate, platinum bead electrode; Yield given. Yields of byproduct given;
In dimethyl sulfoxide controlled-potential electrolysis; 0.1M tetrabutylammonium tetrafluoroborate, platinum bead electrode; Yield given. Yields of byproduct given;
With tetrabutylammonium acetate In dimethyl sulfoxide Product distribution; controlled-potential electrolysis, mercury pool cathode, 0.1M tetrabutylammonium tetrafluoroborate; reaction without base, other base;
diphenylene sulfide

diphenylene sulfide

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
With chromic acid
With dihydrogen peroxide; acetic acid
thianthrene-5,5,10,10-tetraoxide
2362-55-2

thianthrene-5,5,10,10-tetraoxide

tellurium-powder

tellurium-powder

A

Dibenzotellurophen
244-98-4

Dibenzotellurophen

B

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

C

thianthrene 5,5-dioxide
2362-53-0

thianthrene 5,5-dioxide

Conditions
ConditionsYield
at 450℃;
1,2-bis(phenylthio)benzene
3379-36-0

1,2-bis(phenylthio)benzene

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 34percent hydrogen peroxide, glacial acetic acid / 100 °C
2: tetrabutylammonium acetate / dimethylsulfoxide / controlled-potential electrolysis, mercury pool cathode, 0.1M tetrabutylammonium tetrafluoroborate; reaction without base, other base
View Scheme
sodium thiophenolate
930-69-8

sodium thiophenolate

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 50 percent / dimethylsulfoxide / 2.5 h / 45 °C / Irradiation
2: 34percent hydrogen peroxide, glacial acetic acid / 100 °C
3: tetrabutylammonium acetate / dimethylsulfoxide / controlled-potential electrolysis, mercury pool cathode, 0.1M tetrabutylammonium tetrafluoroborate; reaction without base, other base
View Scheme
p,p'-diaminobiphenyl
92-87-5

p,p'-diaminobiphenyl

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfur trioxide; sulfuric acid
2: ethanol; NaNO2; HCl
View Scheme
1-nitro-2-(phenylsulfonyl)benzene
31515-43-2

1-nitro-2-(phenylsulfonyl)benzene

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iron; aq.-ethanolic HCl
2: acetic acid; aqueous hydrochloric acid; sodium nitrite / anschliessend mit Kupfer behandeln
View Scheme
dibenzothiophene
132-65-0

dibenzothiophene

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
With bis(acetylacetonate)oxovanadium; 1,3-dibutylimidazolium bis(trifluoromethylsulfonyl)imide In octane for 0.5 - 2h; Schlenk technique;
With bis(acetylacetonate)oxovanadium; C9H18N(1+)*C2F6NO4S2(1-) In octane for 0.25 - 2h; Schlenk technique;
With bis(acetylacetonate)oxovanadium; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In octane for 0.5 - 2h; Schlenk technique;
(CH3CH2)3SiC6H5CH3(1+)*B(C6F5)4(1-)=(CH3CH2)3SiC6H5CH3B(C6F5)4

(CH3CH2)3SiC6H5CH3(1+)*B(C6F5)4(1-)=(CH3CH2)3SiC6H5CH3B(C6F5)4

C12H8F2OS

C12H8F2OS

A

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

B

C12H8FOS(1+)*C24BF20(1-)

C12H8FOS(1+)*C24BF20(1-)

Conditions
ConditionsYield
In toluene at -35℃; for 0.166667h; Inert atmosphere; Overall yield = 258 mg;
2-iodophenylamine
615-43-0

2-iodophenylamine

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / ethanol / 100 °C
2.1: sodium nitrite; hydrogenchloride / tetrahydrofuran; water / 1 h / 0 - 5 °C
2.2: 20 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 °C
4.1: tetrabutylammomium bromide; sodium metabisulfite; copper(II) bis(trifluoromethanesulfonate); 1,10-Phenanthroline; potassium phosphate / dimethyl sulfoxide / 10 h / 120 °C / Inert atmosphere; Schlenk technique
View Scheme
2-iodophenylamine
615-43-0

2-iodophenylamine

A

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

B

2'-iodo-N-morpholino-[1,1'-biphenyl]-2-sulfonamide

2'-iodo-N-morpholino-[1,1'-biphenyl]-2-sulfonamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / ethanol / 100 °C
2.1: sodium nitrite; hydrogenchloride / tetrahydrofuran; water / 1 h / 0 - 5 °C
2.2: 20 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 °C
4.1: 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate; tetrabutylammomium bromide; sodium metabisulfite; copper(II) bis(trifluoromethanesulfonate); 1,10-Phenanthroline; potassium phosphate / dimethyl sulfoxide / 4 h / 80 °C / Inert atmosphere
View Scheme
phenylboronic acid
98-80-6

phenylboronic acid

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / ethanol / 100 °C
2.1: sodium nitrite; hydrogenchloride / tetrahydrofuran; water / 1 h / 0 - 5 °C
2.2: 20 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 °C
4.1: tetrabutylammomium bromide; sodium metabisulfite; copper(II) bis(trifluoromethanesulfonate); 1,10-Phenanthroline; potassium phosphate / dimethyl sulfoxide / 10 h / 120 °C / Inert atmosphere; Schlenk technique
View Scheme
phenylboronic acid
98-80-6

phenylboronic acid

A

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

B

2'-iodo-N-morpholino-[1,1'-biphenyl]-2-sulfonamide

2'-iodo-N-morpholino-[1,1'-biphenyl]-2-sulfonamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / ethanol / 100 °C
2.1: sodium nitrite; hydrogenchloride / tetrahydrofuran; water / 1 h / 0 - 5 °C
2.2: 20 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 °C
4.1: 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate; tetrabutylammomium bromide; sodium metabisulfite; copper(II) bis(trifluoromethanesulfonate); 1,10-Phenanthroline; potassium phosphate / dimethyl sulfoxide / 4 h / 80 °C / Inert atmosphere
View Scheme
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

Dibenzothiophene sulfoxide
1013-23-6

Dibenzothiophene sulfoxide

Conditions
ConditionsYield
With iodosylbenzene In ethanol at 20℃; Inert atmosphere;100%
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

biphenyl
92-52-4

biphenyl

Conditions
ConditionsYield
With 3-Hydroxy-1-methylpiperidine; nickel diacetate; sodium hydride In tetrahydrofuran at 65℃; for 2h;98%
With sodium; lithium In 1,4-dioxane; mineral oil for 24h; Reflux;96%
In isopropyl alcohol for 5.83333h; Mechanism; Quantum yield; Irradiation; various solvents, deutero-isopropanol;
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

3,5-di-tert-butylaniline
2380-36-1

3,5-di-tert-butylaniline

9-(3,5-di-tert-butylphenyl)-9H-carbazole

9-(3,5-di-tert-butylphenyl)-9H-carbazole

Conditions
ConditionsYield
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 17h; Inert atmosphere;98%
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

2,4-diethyl-9H-thioxanthene

2,4-diethyl-9H-thioxanthene

2',4'-diethylspiro[fluorene-9,9'-thioxanthene]

2',4'-diethylspiro[fluorene-9,9'-thioxanthene]

Conditions
ConditionsYield
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 16h; Inert atmosphere;98%
2-(trifluoromethyl)-9H-thioxanthene
729-10-2

2-(trifluoromethyl)-9H-thioxanthene

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

2'-(trifluoromethyl)spiro[fluorene-9,9'-thioxanthene]

2'-(trifluoromethyl)spiro[fluorene-9,9'-thioxanthene]

Conditions
ConditionsYield
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 16h; Inert atmosphere;98%
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

9H-thioxanthen-2-ol

9H-thioxanthen-2-ol

spiro[fluorene-9,9'-thioxanthen]-2'-ol

spiro[fluorene-9,9'-thioxanthen]-2'-ol

Conditions
ConditionsYield
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 16h; Inert atmosphere;98%
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

7H-benzo[4,5]thieno[3,2-c]xanthene

7H-benzo[4,5]thieno[3,2-c]xanthene

spiro[benzo[4.5]thieno[3,2-c]xanthene-7,9'-fluorene]

spiro[benzo[4.5]thieno[3,2-c]xanthene-7,9'-fluorene]

Conditions
ConditionsYield
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 16h; Inert atmosphere;98%
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

2-phenyl-9H-thioxanthene

2-phenyl-9H-thioxanthene

2'-phenylspiro[fluorene-9,9'-thioxanthene]

2'-phenylspiro[fluorene-9,9'-thioxanthene]

Conditions
ConditionsYield
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 16h; Inert atmosphere;97%
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

3,7-dinitrodibenzothiophene sulfone
58920-49-3

3,7-dinitrodibenzothiophene sulfone

Conditions
ConditionsYield
With sulfuric acid; nitric acid for 1h; 98 deg C, 15 min;;96%
With sulfuric acid; nitric acid at 10 - 20℃; for 13h;55%
With sulfuric acid; nitric acid
Multi-step reaction with 2 steps
1: acetic acid; sulfuric acid; nitric acid
2: sulfuric acid; nitric acid
View Scheme
thioxanthene
261-31-4

thioxanthene

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

spiro[fluorene-9,9’-thioxanthene]

spiro[fluorene-9,9’-thioxanthene]

Conditions
ConditionsYield
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 16h; Inert atmosphere;95%
With potassium hexamethylsilazane In 1,4-dioxane at 80℃; for 24h;76%
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

p-toluidine
106-49-0

p-toluidine

9-(4-methylphenyl)-9H-carbazole
19264-73-4

9-(4-methylphenyl)-9H-carbazole

Conditions
ConditionsYield
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 16h; Reagent/catalyst; Inert atmosphere;94%
Multi-step reaction with 2 steps
1: potassium hexamethylsilazane / 1,4-dioxane; toluene / 16 h / 20 °C / Inert atmosphere
2: potassium hexamethylsilazane / 1,4-dioxane; toluene / 16 h / 80 °C / Inert atmosphere
View Scheme
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

4-methoxy-aniline
104-94-9

4-methoxy-aniline

9-(4-methoxyphenyl)-9H-carbazole
19264-74-5

9-(4-methoxyphenyl)-9H-carbazole

Conditions
ConditionsYield
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 16h; Inert atmosphere;94%
9,10-dihydroanthracene
613-31-0

9,10-dihydroanthracene

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

bi-spirofluorene
159-56-8

bi-spirofluorene

Conditions
ConditionsYield
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 100℃; for 72h; Inert atmosphere;94%
xanthene
92-83-1

xanthene

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

spiro(fluorene-9,9′-xanthene)
159-62-6

spiro(fluorene-9,9′-xanthene)

Conditions
ConditionsYield
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 16h; Inert atmosphere;93%
Multi-step reaction with 2 steps
1: potassium hexamethylsilazane / 1,4-dioxane; toluene / 1.5 h / 80 °C / Inert atmosphere
2: potassium hexamethylsilazane / 1,4-dioxane; toluene / 16 h / 80 °C / Inert atmosphere
View Scheme
(4-methylphenyl)acetonitrile
2947-61-7

(4-methylphenyl)acetonitrile

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

9-(4-methylphenyl)fluorene
18153-43-0

9-(4-methylphenyl)fluorene

Conditions
ConditionsYield
With potassium hexamethylsilazane In toluene; Petroleum ether at 100℃; for 24h; Inert atmosphere;93%
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

4-tert-Butylaniline
769-92-6

4-tert-Butylaniline

9-(4-(tert-butyl)phenyl)-9H-carbazole
57103-13-6

9-(4-(tert-butyl)phenyl)-9H-carbazole

Conditions
ConditionsYield
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 16h; Inert atmosphere;92%
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

2-methoxy-9H-thioxanthene
57274-96-1

2-methoxy-9H-thioxanthene

2'-methoxyspiro[fluorene-9,9'-thioxanthene]

2'-methoxyspiro[fluorene-9,9'-thioxanthene]

Conditions
ConditionsYield
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 16h; Inert atmosphere;92%
3-methylbenzyl cyanide
2947-60-6

3-methylbenzyl cyanide

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

9-(3-methylphenyl)-9H-fluorene
18153-42-9

9-(3-methylphenyl)-9H-fluorene

Conditions
ConditionsYield
With potassium hexamethylsilazane In toluene; Petroleum ether at 100℃; for 24h; Inert atmosphere;92%
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

4-amino-N,N-dimethylaniline
99-98-9

4-amino-N,N-dimethylaniline

4-(9H-carbazol-9-yl)-N,N-dimethylaniline
53167-75-2

4-(9H-carbazol-9-yl)-N,N-dimethylaniline

Conditions
ConditionsYield
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 17h; Inert atmosphere;91%
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

C16H15Br

C16H15Br

C28H21Br

C28H21Br

Conditions
ConditionsYield
In 1,4-dioxane at 80℃; for 16h; Inert atmosphere;90.5%
9,10-dihydroanthracene
613-31-0

9,10-dihydroanthracene

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

spiro(fluorene-9,9′-anthracene)
159-61-5

spiro(fluorene-9,9′-anthracene)

Conditions
ConditionsYield
With potassium hexamethylsilazane In 1,4-dioxane90%
Dibenzothiophene sulfoxide
1013-23-6

Dibenzothiophene sulfoxide

dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

2,2'-Bithiophene
492-97-7

2,2'-Bithiophene

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

C20H13S3(1+)*C2F3O2(1-)

C20H13S3(1+)*C2F3O2(1-)

Conditions
ConditionsYield
In acetonitrile at -78 - 25℃; for 1.33333h;88%
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

3,7-dibromo-dibenzothiophene-5,5-dioxide
83834-12-2

3,7-dibromo-dibenzothiophene-5,5-dioxide

Conditions
ConditionsYield
With N-Bromosuccinimide; sulfuric acid at 0℃; for 10h; Inert atmosphere;87%
With N-Bromosuccinimide; sulfuric acid at 20℃; for 7h;87%
With N-Bromosuccinimide; sulfuric acid at 0 - 20℃; for 10h;78%
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

2-Phenylphenol
90-43-7

2-Phenylphenol

Conditions
ConditionsYield
Stage #1: dibenzothiophene sulfone With sodium hydroxide In water at 300℃; for 1.5h; Autoclave;
Stage #2: With hydrogenchloride In water pH=7; Product distribution / selectivity;
86.5%
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

hexan-1-amine
111-26-2

hexan-1-amine

N-hexylcarbazole
4041-21-8

N-hexylcarbazole

Conditions
ConditionsYield
Stage #1: dibenzothiophene sulfone; hexan-1-amine With lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 3h; Schlenk technique; Inert atmosphere;
Stage #2: With potassium hexamethylsilazane In 1,4-dioxane at 100℃; for 2h; Reagent/catalyst; Schlenk technique; Inert atmosphere;
86%
Multi-step reaction with 2 steps
1: lithium hexamethyldisilazane / 1,4-dioxane / 3 h / 100 °C / Schlenk technique; Inert atmosphere
2: potassium hexamethylsilazane / 1,4-dioxane / 2 h / 100 °C / Schlenk technique; Inert atmosphere
View Scheme
dibenzothiophene sulfone
1016-05-3

dibenzothiophene sulfone

3-nitrodibenzo[b,d]thiophene 5,5-dioxide
51762-59-5

3-nitrodibenzo[b,d]thiophene 5,5-dioxide

Conditions
ConditionsYield
With sulfuric acid; nitric acid; acetic acid at 0 - 4℃; for 2h;85%
With sulfuric acid; nitric acid; acetic acid at -5 - 5℃; for 2h;72%
With sulfuric acid; nitric acid; acetic acid for 2h;72%
With sulfuric acid; nitric acid; acetic acid
With nitric acid In sulfuric acid

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The reactivity of dibenzothiophene (DBT) or dibenzothiophene sulfone (DBTO2) with a variety of phenylboronic acids was mediated by the nickel precursor [Ni(dippe)Cl2] in the presence of a base. The reaction was performed under relatively mild conditions (70–100 °C), in aqueous media. The study...detailed

1016-05-3Relevant articles and documents

Non-hydrolytic synthesis of mesoporous silica-titania catalysts for the mild oxidation of sulfur compounds with hydrogen peroxide

Cojocariu, Ana Mihaela,Mutin, P. Hubert,Dumitriu, Emil,Fajula, Francois,Vioux, Andre,Hulea, Vasile

, p. 5357 - 5359 (2008)

A SiO2-TiO2 mesoporous xerogel prepared in one-step by a non-hydrolytic route shows excellent performance in the mild oxidation of sulfides, sulfoxides and thiophenes with aqueous solutions of H 2O2. The Royal Society of Chemistry.

Oxidation of dibenzothiophene by hydrogen peroxide catalyzed by solid bases

Figueras,Palomeque,Clacens

, p. 103 - 108 (2002)

The removal of sulfur compounds from hydrocarbon-based distillate fuels is essential due to environmental concerns (i.e., acid rain and airborne particulate material production), and because a few parts per million of sulfur are enough to poison the catalysts used for the purification of the exhaust gases of diesel cars. The oxidation of dibenzothiophene (DBT) by H2O2 at 333 K was investigated using the catalysts (hydrotalcite (HT) and MgLa mixed oxide) and solvents (methanol, acetonitrile, benzonitrile, acrylonitrile, and 3-methoxypropionitrile). High activity was found only after calcinations followed by rehydration of HT. Acetonitrile was the best solvent, while much lower reaction rates were observed in methanol. The decomposition of H2O2 into oxygen was observed for HT, and was the major reaction at > 353 K. This reaction did not occur in the absence of nitrile, and was faster over MgLa mixed oxide of higher basic strength. The activity increased with increasing Mg/Al ratio due to a lower rate of H2O2 decomposition attributed to a lower basicity of the solid.

Synergy between bis(dimethyldioctylammonium) molybdate and tetraethylene glycol monooctyl ether: A winning combination for interfacial catalysis in thermo-controlled and switchable microemulsions

Hong, Bing,Leclercq, Lo?c,Collinet-Fressancourt, Marion,Lai, Jonathan,Bauduin, Pierre,Aubry, Jean-Marie,Nardello-Rataj, Véronique

, p. 142 - 149 (2015)

A simple thermo-responsive one-phase microemulsion (μem) is designed to enable the dark singlet oxidation of organic substrates while allowing a straightforward separation of the catalytic surfactant and products in two distinct phases by cooling down the reaction medium. This latter is prepared by combining a small amount (1%) of the catalytic surfactant bis(dimethyldioctylammonium) molybdate, [DiC8]2[MoO4], with the nonionic amphiphile tetraethylene glycol monooctyl ether, C8E4. Tensiometry and dynamic light scattering are used to rationalize the synergy between the two surfactants which strongly interact. The oxidation takes place in the effective one-phase Winsor IV system which separates into two phases (μem + oil, i.e. Winsor I) just by temperature change thanks to the presence of the thermosensitive C8E4. The thermal-controlled nanostructured reaction medium is applied to the ene reaction, [4+2] cycloaddition and sulfide oxidation.

One-pot extractive and oxidative desulfurization of liquid fuels with molecular oxygen in ionic liquids

Wang, Jianlong,Guo, Qingping,Zhang, Changming,Li, Kaixi

, p. 59885 - 59889 (2014)

Benzothiophene (BT), dibenzothiophene (DBT) and 4,6-dimethlydibenzothiophene (4,6-DMDBT) were extracted from an oil phase to ionic liquid phase, and then oxidized to the corresponding sulfone by the cheap catalyst, N-hydroxyphthalimide (NHPI), using molecular oxygen as the oxidant in one-pot. The system can be recycled 5 times without a significant decrease in desulfurization.

Efficient molybdenum catalyzed chemoselective, solvent-free oxidation of sulfides to sulfones at room temperature

Hadigavabar, Ali Dadashi,Tabatabaeian, Khalil,Zanjanchi, Mohammad Ali,Mamaghani, Manouchehr

, p. 3829 - 3833 (2018)

An effcient and reusable molybdenum-based catalyst has been prepared by tethering dioxomolybdenumacetylacetonate complex, MoO2(acac)2, via postsynthesis modifcation of zeolite beta. The catalyst has been characterized by Fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), scanning electron microscopy-energy dispersive X-ray analysis (SEM-EDX) and inductively coupled plasma (ICP). The catalyst exhibited very high activity for the selective oxidation of sulfdes to sulfones at room temperature. The catalyst can be recycled and reused four times without signifcant loss of activity.

Tungstophosphoric Acid-catalyzed Oxidative Desulfurization of Light Oil with Hydrogen Peroxide in a Light Oil/Acetic Acid Biphasic System

Yazu, Kazumasa,Furuya, Takeshi,Miki, Keiji,Ukegawa, Koji

, p. 920 - 921 (2003)

Dibenzothiophenes were oxidized effectively with H2O 2 in the presence of 12-tungstophosphoric acid in the tetradecane/ AcOH biphasic system to give their corresponding sulfones as the major products. The oxidation proceeded in the AcOH phase and most of the sulfones distributed there, resulting in the successive removal of the sulfur compounds from the tetradecane phase. This biphasic oxidation system can effectively reduce the sulfur content in light oil.

Polyoxometalate [γ-SiW10O34(H 2O)2]4- on MCM-41 as catalysts for sulfide oxygenation with hydrogen peroxide

Thompson, Dylan J.,Zhang, Yang,Ren, Tong

, p. 188 - 193 (2014)

The polyoxometalate (POM) catalyst, [γ-SiW10O 34(H2O)2]4-, was introduced into the pores of both as-synthesized (I) and amine functionalized MCM-41 (II). The resultant catalysts were characterized with powder X-ray diffraction, nitrogen sorption, and diffuse-reflectance UV-vis spectroscopy. Both catalysts were tested for reusability through repeated catalytic conversions of methyl phenyl sulfide to methyl phenyl sulfone with hydrogen peroxide. While the physisorbed catalyst (I) exhibits steadily decreasing turnover frequency (TOF), the POM catalyst supported on MCM-41 functionalized with a protonated amine (II) exhibits markedly improved reusability. This chemisorbed catalyst effectively showed no change in TOF between the second (21) and the sixth reactions (22). Additionally, sulfoxidations with catalyst II were investigated with a small set of substrates focusing on compounds including dibenzothiophene, which serves as a model refractory sulfide.

Extraction and oxidative desulfurization of diesel fuel catalyzed by a Bronsted acidic ionic liquid at room temperature

Gao, Hongshuai,Guo, Chen,Xing, Jianmin,Zhao, Junmei,Liu, Huizhou

, p. 1220 - 1224 (2010)

The Bronsted acidic ionic liquids 1-butyl-3-methylimidazolium hydrogen sulfate ([BMIM][HSO4]) and N-butylpyridinium hydrogen sulfate ([C4Py][HSO4]) were used as extractant and catalyst for desulfurization of diesel. The results show that [BMIM][HSO 4] is better as extractant and catalyst than [C4Py] [HSO4] during the desulfurization process. The sulfur removal of dibenzothiophene (DBT) in n-octane was 99.6% in 90 min under the conditions of Vmodel oil/VIL = 2:1 and H2O2/DBT molar ratio at 5 (O/S = 5), at room temperature. The sulfur removal of four sulfur compounds by extraction and catalytic oxidation process followed the order of DBT > benzothiophene (BT) > thiophene (TS) > 4,6-dimethyldibenzothiophene (4,6-DMDBT). Moreover, the [BMIM][HSO4] can be recycled for at least 6 times with a little decrease in the desulfurization activity. The sulfur removal of diesel fuel containing sulfur content of 97 ppm is 85.5%, which was much better than desulfurization performance by simple extraction with IL (11.0%). In this extraction and oxidative desulfurization process, DBT was oxidized to corresponding sulfone by H2O2 with Bronsted acidic IL [BMIM][HSO 4] which served as not only extractant but also catalyst. The Royal Society of Chemistry 2010.

Oxidation of sulfides to sulfoxides and sulfones with 30% hydrogen peroxide under organic solvent- and halogen-free conditions

Sato, Kazuhiko,Hyodo, Mamoru,Aoki, Masao,Zheng, Xiao-Qi,Noyori, Ryoji

, p. 2469 - 2476 (2001)

Aromatic and aliphatic sulfides are oxidized to sulfoxides or sulfones in high yield with 30% hydrogen peroxide under organic solvent- and halogen-free conditions. Dialkyl and alkyl aryl sulfides are cleanly oxidized to sulfoxides using aqueous hydrogen peroxide without catalysts. The best catalyst for the sulfone synthesis consists of sodium tungstate, phenylphosphonic acid, and methyltrioctylammonium hydrogensulfate. Co-existing primary or secondary alcohol or olefinic moieties are unaffected under such conditions.

Selective sulfoxidation with hydrogen peroxide catalysed by a titanium catalyst

Postigo, Lorena,Ventura, Maria,Cuenca, Toms,Jimnez, Gerardo,Royo, Beatriz

, p. 320 - 324 (2015)

A moisture-tolerant cyclopentadienyl-silsesquioxane titanium complex efficiently catalyses the selective oxidation of various types of sulfides to either sulfoxides (TOFs up to 32 530 h-1) or sulfones with H2O2 (30% in water) under mild conditions.

-

LaCount,Friedman

, p. 2751,2753 (1977)

-

Oxidative Desulfurization of Dibenzothiophene Using Cobalt (II) Complexes with Substituted Salen-Type Ligands as Catalysts in Model Fuel Oil

Tripathi, Deependra,Singh, Raj K.

, p. 713 - 719 (2021)

Three cobalt(II)-salen complexes (CoL1, CoL2 and CoL3) were synthesized via the reaction of the three tetradentate ligands as N,N′-ethylenebis(salicylimine) L1, N,N′-ethylenebis(3-tert-butylsalicylimine) L2 and N,N′-ethylenebis(3,5-di-tert-butylsalicylimine) L3, with a stoichiometric amount of cobalt(II) acetate tetrahydrate, respectively. All the three complexes were studied as oxidative desulfurization catalyst on dibenzothiophene taken in model fuel oil n-dodecane. The acetonitrile used as an extracting solvent and H2O2 as an oxidant. Comparatively CoL3 proved to be the best catalyst which showed the 76% DBT removal at the optimized conditions. The nth-order kinetic model is the best way to represent oxidation kinetics of complexes. Graphic Abstract: [Figure not available: see fulltext.]This cobalt(II) Schiffs base complexes were studied as catalyst for oxidative desulfurization of dibenzothiphene (DBT) taken as model sulphur compounds in fuel model oil (n-dodecane) using H2O2 as oxidant and acetonitrile as extracting solvent for DBT sulfone in a batch experiment.

Novel yellow phosphorescent iridium complexes with dibenzothiophene-S,S-dioxide-based cyclometalated ligand for white polymer light-emitting diodes

Liang, Aihui,Luo, Ming,Liu, Yusheng,Wang, Han,Wang, Zhiping,Zheng, Xiaoyan,Cao, Tian,Liu, Dewang,Zhang, Yong,Huang, Fei

, p. 637 - 645 (2018)

We have designed and synthesized two novel yellow phosphorescent iridium complexes using dibenzothiophene-S,S-dioxide-based cyclometalated ligand for the first time, which are capable of producing highly efficient yellow and white polymer light-emitting devices (PLEDs). The resulted iridium complexes display good thermal stability and high photoluminescence quantum yields. Both yellow and white PLEDs are fabricated with an identical single-emission-layer configuration of ITO/PEDOT:PSS/emission layer (EML)/CsF/Al. For the yellow phosphorescent PLEDs based on (p-CzFSOPy)2IrPic, the best device performances with a peak luminous efficiency (LE) of 13.3 cd/A and a peak external quantum efficiency (EQE) of 5.3% are achieved. More importantly, the two-element WPLEDs containing iridium (III)bis (2-(4,6-difluorophenyl)-pyridinato-N,C2′) picolinate (FIrpic) as blue and (p-CzFSOPy)2IrPic as yellow phosphors doped into a PVK:OXD-7 matrix at an appropriate ratio exhibited a maximum LE of 19.2 cd/A, a maximum EQE of 9.6%, an extremely high luminance of 18717 cd/m2 and Commission Internationale de L'Eclairage (CIE) coordinate of (0.317, 0.448). Moreover, at a luminance for practical application of 1000 cd/m2, the LE still remains as high as 19.0 cd/A, with a very slight decrease.

-

Tilak

, p. 76,87 (1960)

-

-

Ledlie,Howell

, p. 785 (1976)

-

An efficient method for the oxidation of organic sulfides to sulfones

Balicki, Roman

, p. 184 - 185 (1999)

Mild and safe oxidation of dialkyl-, diaryl- and alkyl-aryl sulfides (1a-m) to the corresponding sulfones (2a-m)by using urea-hydrogen peroxide/formic acid system is reported. Wiley-VCH Verlag GmbH, 1999.

Efficient mesoporous silica-titania catalysts from colloidal self-assembly

Sachse, Alexander,Hulea, Vasile,Marcotte, Nathalie,Boltoeva, Maria Yu,Belamie, Emmanuel,Alonso, Bruno,Kostov, Krassimir L.

, p. 10648 - 10650,3 (2012)

Mesoporous silica-titania materials of tunable composition and texture, which present a high catalytic activity in the mild oxidation of sulfur compounds, have been obtained by combining the spray-drying process with the colloidal self-assembly of α-chitin nanorods (biopolymer acting as a template) and organometallic oligomers.

The adsorptive extraction of oxidized sulfur-containing compounds from fuels by using molecularly imprinted chitosan materials

Ogunlaja, Adeniyi S.,Coombes, Matthew J.,Torto, Nelson,Tshentu, Zenixole R.

, p. 61 - 76 (2014)

An innovative approach for desulfurisation of fuels is proposed. It relies on the formation of recognition sites, complementary to oxidized sulfur-containing compounds, on cross-linked chitosan microspheres and electrospun chitosan nanofibers using the molecularly imprinted polymer technique. Benzothiophene sulfone (BTO2), dibenzothiophene sulfone (DBTO2) and 4,6-dimethyldibenzothiophene sulfone (4,6-DMDBTO 2) were used as templates for the preparation of molecularly imprinted polymers (MIPs). The possible molecular interactions between imprinted chitosan adsorbent and oxidized sulfur-containing compounds were investigated by molecular modeling using density functional theory (DFT) and results indicated that interactions took place via hydrogen bonding. The molecularly imprinted polymer adsorbents (cross-linked microspheres and electrospun nanofibers) gave better selectivity for the target sulfonated compounds and the adsorption isothermal studies followed the Freundlich model. Maximum adsorption capacities of 8.5 ± 0.6 mg/g, 7.0 ± 0.5 mg/g and 6.6 ± 0.7 mg/g were observed for model BTO2, DBTO2 and 4,6-DMDBTO2 respectively at 1 mL/h when imprinted nanofibers were employed, and the imprinted microspheres gave maximum adsorption capacity of 4.9 ± 0.5 mg/g, 4.2 ± 0.7 mg/g and 3.9 ± 0.6 mg/g for BTO 2, DBTO2 and 4,6-DMDBTO2 respectively. Application of the nanofibers to oxidized hydro-treated fuel under continuous flow adsorption system at 1 mL/h indicated that 84% of sulfur was adsorbed, with adsorption capacity of 2.2 ± 0.2 mg/g.

Deep oxidative desulfurization with task-specific ionic liquids: An experimental and computational study

Gui, Jianzhou,Liu, Dan,Sun, Zhaolin,Liu, Daosheng,Min, Dayoung,Song, Busub,Peng, Xilai

, p. 64 - 70 (2010)

A series of task-specific acidic ionic liquids (TSILs), immiscible with oil, halogen-free and containing -COOH group in the cations, were used for oxidative desulfurization as both the catalyst and extractant. The removal of dibenzothiophene (DBT) and 4,6-dimethyldibenzothiophene (4,6-DMDBT) from model diesel at 298 K could reach 96.7% and 95.1%, respectively. The TSIL could be recycled 5 times without any apparent loss of the catalytic activity. Meanwhile, the structures, acidities and interactions between the cation and the anion of TSILs have been investigated by density functional theory (DFT) method, and found that catalytic properties of TSILs are close related to the structures, acidities and extraction capabilities. Furthermore, an oxidative desulfurization mechanism has been proposed.

Oxidation of organic sulfur compounds with hydrogen peroxide in the presence of crown ethers

Anisimov,Tarakanova,Tkhai, Fat Vin,Kulikov,Seleznev

, p. 225 - 225 (2007)

It was first shown that crown ethers catalyze the oxidation of organic sulfur compounds (methyl phenyl sulfide to sulfoxide and sulfone, benzothiophene and dibenzothiophene to sulfones) with hydrogen peroxide. Nauka/Interperiodica 2007.

Anchorage of a ruthenium complex into modified MOF: Synergistic effects for selective oxidation of aromatic and heteroaromatic compounds

Tabatabaeian, Khalil,Zanjanchi, Mohammad Ali,Mahmoodi, Nosrat. O.,Eftekhari, Tooraj

, p. 101013 - 101022 (2015)

The structure of IRMOF-3 was modified with pyridine-2-aldehyde and then the Schiff base moieties were used to anchor ruthenium complex to this metal-organic framework. The prepared catalyst was characterized by X-ray powder diffraction (XRD), diffuse reflectance spectroscopy (DRS), scanning electron microscopy (SEM), transmission electron microscopy (TEM) and FTIR methods. The results show that the prepared catalyst acquires a high potential for selective oxidation of aromatic and heteroaromatic compounds under mild conditions and easy workups.

Metal and solvent free selective oxidation of sulfides to sulfone using bifunctional ionic liquid [pmim]IO4

Ahammed, Sabir,Kundu, Debasish,Siddiqui, Mohammad Nahid,Ranu, Brindaban C.

, p. 335 - 337 (2015)

The oxidation of organo-sulfides to sulfones has been accomplished using an easily accessible bifunctional ionic liquid, [pmim]IO4 in the absence of any other oxidants, metal and organic solvent at ambient temperature. A variety of sulfides including dialkyl, aryl-alkyl, diaryl, and aryl-hetero aryl have been oxidized to the corresponding functionalized sulfones in high yields by this procedure.

Substrate specificity and ionization potential in chloroperoxidase- catalyzed oxidation of diesel fuel

Ayala, Marcela,Robledo, Norma R.,Lopez-Munguia, Agustin,Vazquez-Duhalt, Rafael

, p. 2804 - 2809 (2000)

Straight-run diesel fuel containing 1.6% of sulfur was enzymatically oxidized with chloroperoxidase from Caldariomyces rumago. Most organosulfides and thiophenes were transformed to form sulfoxides and sulfones. The oxidized organosulfur compounds can be effectively removed by distillation. The resulting fraction after distillation contained only 0.27% sulfur, while the untreated straight-run diesel fuel after the same distillation process still showed 1.27% sulfur. To know the chemical nature of the products, nine organosulfur compounds and 12 polycyclic aromatic compounds (PACs) were transformed by chloroperoxidase in the presence of chloride and hydrogen peroxide. Organosulfur compounds were only oxidized to form sulfoxides and sulfones, and no chlorinated derivatives were detected, except for bithiophene. In contrast, PACs were exclusively chlorinated, and no oxidized derivatives could be found. No enzymatic activity was detected on PACs with an ionization potential higher than 8.52 eV, while in the lower region it was found that the higher the ionization potential of the PAC the lower the specific activity. On the other hand, the substrate ionization potential did not seem to influence chloroperoxidase activity in the oxidation of organosulfur compounds. All organosulfur compounds tested were oxidized by chloroperoxidase. From double-substrate experiments, it appears that organosulfur compounds are oxidized by both compound I and compound X enzyme intermediates, while PACs react only with the halogenating intermediate, compound X. Straight-run diesel fuel containing 1.6% of sulfur was enzymatically oxidized with chloroperoxidase from Caldariomyces fumago. Most organosulfides and thiophenes were transformed to form sulfoxides and sulfones. The oxidized organosulfur compounds can be effectively removed by distillation. The resulting fraction after distillation contained only 0.27% sulfur, while the untreated straight-run diesel fuel after the same distillation process still showed 1.27% sulfur. To know the chemical nature of the products, nine organosulfur compounds and 12 polycyclic aromatic compounds (PACs) were transformed by chloroperoxidase in the presence of chloride and hydrogen peroxide. Organosulfur compounds were only oxidized to form sulfoxides and sulfones, and no chlorinated derivatives were detected, except for bithiophene. In contrast, PACs were exclusively chlorinated, and no oxidized derivatives could be found. No enzymatic activity was detected on PACs with an ionization potential higher than 8.52 eV, while in the lower region it was found that the higher the ionization potential of the PAC the lower the specific activity. On the other hand, the substrate ionization potential did not seem to influence chloroperoxidase activity in the oxidation of organosulfur compounds. All organosulfur compounds tested were oxidized by chloroperoxidase. From double-substrate experiments, it appears that organosulfur compounds are oxidized by both compound I and compound X enzyme intermediates, while PACs react only with the halogenating intermediate, compound X.

Synthesis and non-parametric evaluation studies on high performance of catalytic oxidation-extraction desulfurization of gasoline using the novel TBAPW11Zn?TiO2?PAni nanocomposite

Khanmohammadi Khorrami, Mohammad Reza,Shokri Aghbolagh, Zahra

, (2020)

In this work, the new catalyst (assigned as TBAPW11Zn?TiO2?PAni) was successfully designed and synthesized on the basis of quaternary ammonium salt of zinc monosubstituted phosphotungstate [(n-C4H9)4N][PW11ZnO39] (TBAPW11Zn), titanium dioxide (TiO2), and polyaniline (PAni). This study reports the catalytic oxidation-extraction desulfurization (ECODS) of sulfur-containing molecules from real and the simulated (Th, BT, and DBT) gasoline using new organic–inorganic hybrid catalyst (TBAPW11Zn?TiO2?PAni). The ECODS results were shown that the concentration of sulfur compounds (SCs) of real gasoline was lowered from 0.4992 to 0.0122 wt.% with 97% efficiency at 35 °C after 1 h. Furthermore, the synthesized heterogeneous nanocatalyst showed high stability and reusability after five times without significant loss of activity. The high performance of TBAPW11Zn?TiO2?PAni/H2O2/CH3CO2H system can be a promising route with a superb potential in the generation of ultra-low-sulfur gasoline. Also the Mann–Whitney U-test results show that there is not a significant difference between the mean of sulfur percentage for DBT & BT, BT & Th and DBT & Th in the presence of the catalyst. Based on the Kruskal–Wallis test results, we can conclude that the temperature, time and amount of catalyst have a significant effect on ECODS efficiency of TBAPW11Zn?TiO2?PAni nanocomposite.

The development of catalytic oxovanadium(IV)-containing microspheres for the oxidation of various organosulfur compounds

Ogunlaja, Adeniyi S.,Khene, Samson,Antunes, Edith,Nyokong, Tebello,Torto, Nelson,Tshentu, Zenixole R.

, p. 157 - 167 (2013)

The development of poly[allylSB-co-EGDMA] beads containing a tetradentate ligand was achieved via suspension polymerization. The catalyst poly[allylSB-co-EGDMA]-VO was synthesized by reacting VIVOSO 4 with poly[allylSB-co-EGDMA]. XPS

Visible-light-promoted aerobic oxidation of sulfides and sulfoxides in ketone solvents

Li, Xiaotong,Wang, Yu,Xie, Xiaomin,Yang, Liqun,Zhang, Zhaoguo

, (2022/03/09)

Simple and readily available ketones have been identified to promote the visible-light-promoted aerobic oxidation of sulfides and sulfoxides to sulfones. We report a simple and environmental-friendly oxidation protocol of sulfides to sulfones. Various sulfides were efficiently oxidized into sulfones with O2 as sustainable terminate oxidant, readily available thioxanthone as the photocatalyst and 3-pentanone (DEK) as the solvent. The protocol tolerates diverse functional groups, including halogens, ketone, ester, cyano, heterocycle and even cyclopropyl groups. The detection of the aerobic oxidation reaction in DEK by GC and HRMS disclosed that the key active intermediates were generated.

Synergistic cooperative effect of CF3SO2Na and bis(2-butoxyethyl)ether towards selective oxygenation of sulfides with molecular oxygen under visible-light irradiation

Liu, Kai-Jian,Wang, Zheng,Lu, Ling-Hui,Chen, Jin-Yang,Zeng, Fei,Lin, Ying-Wu,Cao, Zhong,Yu, Xianyong,He, Wei-Min

supporting information, p. 496 - 500 (2021/01/28)

A safe, practical and eco-friendly method for the switchable synthesis of sulfoxides and sulfones through visible-light-initiated oxygenation of sulfides at ambient temperature under transition-metal-, additives-free and minimal solvent conditions. The synergistic catalytic efforts between CF3SO2Na and 2-butoxyethyl ether represents the key promoting factor for the reaction. This journal is

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