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109-66-0

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109-66-0 Usage

Safety Profile

Moderately toxic by inhalation and intravenous routes. Narcotic in high concentration. The liquid can cause blisters oncontact. Flammable liquid. Highly dangerous fire hazard when exposed to heat, flame, or oxidizers. Severe explosion hazard when exposed

Check Digit Verification of cas no

The CAS Registry Mumber 109-66-0 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 9 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 109-66:
(5*1)+(4*0)+(3*9)+(2*6)+(1*6)=50
50 % 10 = 0
So 109-66-0 is a valid CAS Registry Number.
InChI:InChI=1/C5H12/c1-3-5-4-2/h3-5H2,1-2H3

109-66-0 Well-known Company Product Price

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  • Alfa Aesar

  • (47115)  n-Pentane, anhydrous, 99.8+%, over molecular sieves, packaged under Argon in resealable ChemSeal? bottles   

  • 109-66-0

  • 250ml

  • 328.0CNY

  • Detail
  • Alfa Aesar

  • (47115)  n-Pentane, anhydrous, 99.8+%, over molecular sieves, packaged under Argon in resealable ChemSeal? bottles   

  • 109-66-0

  • 1L

  • 780.0CNY

  • Detail
  • Alfa Aesar

  • (40981)  n-Pentane, Environmental Grade, 98+%   

  • 109-66-0

  • 1L

  • 273.0CNY

  • Detail
  • Alfa Aesar

  • (40981)  n-Pentane, Environmental Grade, 98+%   

  • 109-66-0

  • 4L

  • 802.0CNY

  • Detail
  • Alfa Aesar

  • (40981)  n-Pentane, Environmental Grade, 98+%   

  • 109-66-0

  • *4x1L

  • 1029.0CNY

  • Detail
  • Alfa Aesar

  • (40981)  n-Pentane, Environmental Grade, 98+%   

  • 109-66-0

  • *4x4L

  • 2760.0CNY

  • Detail
  • Alfa Aesar

  • (22907)  n-Pentane, HPLC Grade, 99% min   

  • 109-66-0

  • 1L

  • 476.0CNY

  • Detail
  • Alfa Aesar

  • (22907)  n-Pentane, HPLC Grade, 99% min   

  • 109-66-0

  • 4L

  • 1372.0CNY

  • Detail
  • Alfa Aesar

  • (22907)  n-Pentane, HPLC Grade, 99% min   

  • 109-66-0

  • *4x1L

  • 1574.0CNY

  • Detail
  • Alfa Aesar

  • (22907)  n-Pentane, HPLC Grade, 99% min   

  • 109-66-0

  • *4x4L

  • 4322.0CNY

  • Detail
  • Alfa Aesar

  • (H27427)  Pentane, HPLC Grade, 99+% (n-Pentane, 95% min)   

  • 109-66-0

  • 1000ml

  • 609.0CNY

  • Detail
  • Alfa Aesar

  • (H27427)  Pentane, HPLC Grade, 99+% (n-Pentane, 95% min)   

  • 109-66-0

  • 2500ml

  • 1127.0CNY

  • Detail

109-66-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name pentane

1.2 Other means of identification

Product number -
Other names PENTANE,(MIXEDISOMERS)

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fuels and fuel additives,Intermediates,Paint additives and coating additives not described by other categories,Plasticizers,Processing aids, not otherwise listed,Processing aids, specific to petroleum production,Propellants and blowing agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

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

More Details:109-66-0 SDS

109-66-0Synthetic route

1-penten
109-67-1

1-penten

pentane
109-66-0

pentane

Conditions
ConditionsYield
With H3Ni4(C5H5)4; hydrogen at 40℃; under 760 Torr; other olefins; var. times;100%
With hydrogen In N,N-dimethyl-formamide at 25℃; under 760.051 Torr; for 10h;87%
With C14H15NZr In toluene at 25℃; Reagent/catalyst;11%
2-Pentyne
627-21-4

2-Pentyne

A

(Z)-pent-2-ene
627-20-3

(Z)-pent-2-ene

B

pentane
109-66-0

pentane

Conditions
ConditionsYield
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760 Torr; Kinetics;A 99.5%
B n/a
triethylsilane
617-86-7

triethylsilane

1-fluoropentane
592-50-7

1-fluoropentane

A

triethylsilyl fluoride
358-43-0

triethylsilyl fluoride

B

pentane
109-66-0

pentane

Conditions
ConditionsYield
With C21H16N3P(2+) In dichloromethane at 25℃; for 1.5h; Reagent/catalyst;A 97%
B n/a
With [(SIMes)PFMe2][B(C6F5)4]2 In dichloromethane-d2 for 1h; Catalytic behavior; Inert atmosphere;
2-Pentyne
627-21-4

2-Pentyne

A

(Z)-pent-2-ene
627-20-3

(Z)-pent-2-ene

B

(E)-pent-2-ene
646-04-8

(E)-pent-2-ene

C

pentane
109-66-0

pentane

Conditions
ConditionsYield
With hydrogen; (3-ClMe2SiPr)P(Ph)CH2C4H7O2 on silicagel In propan-1-ol at 20℃; under 750.06 Torr; for 0.333333h; Product distribution; var. catalyst;A 96%
B 3%
C 1%
With hydrogen; palladium dichloride In N,N-dimethyl-formamide under 18751.5 Torr; for 0.216667h; Product distribution; Ambient temperature; various time;A 1.7%
B 82.7%
C 1.4%
With hydrogen In hexane at 24.84 - 59.84℃; Kinetics; Autoclave; Inert atmosphere;
1-fluoropentane
592-50-7

1-fluoropentane

pentane
109-66-0

pentane

Conditions
ConditionsYield
With triethylsilane; C24BF20(1-)*C30H32BF5P(1+) at 100℃; for 48h; Reagent/catalyst;95%
With triethylsilane; 2C24BF20(1-)*C18H17FNP(2+) at 25℃; for 1h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique; Glovebox;92%
With trityl tetrakis(pentafluorophenyl)borate In 1,2-dichloro-benzene at 22℃; for 24h; Product distribution; Further Variations:; Reagents; Solvents;
hexan-1-ol
111-27-3

hexan-1-ol

A

hexane
110-54-3

hexane

B

pentane
109-66-0

pentane

Conditions
ConditionsYield
With hydrogen; aluminum oxide; nickel at 120℃;A 5%
B 94%
With hydrogen In n-heptane at 199.84℃; under 22502.3 Torr; Kinetics; Autoclave;
Cyclopentane
287-92-3

Cyclopentane

pentane
109-66-0

pentane

Conditions
ConditionsYield
With hydrogen; osmium(VIII) oxide at 120℃; under 37503 Torr; for 15h; or 100 to 180 deg C, different Os-catalysts and -concentrations; Further byproducts given;90%
With hydrogen; osmium(VIII) oxide at 120℃; under 37503 Torr; for 15h; Product distribution; different Os-catalysts and concentration; reaction temperatures; other alkanes, cycloalkanes, benzene, toluene;90%
With platinum on activated charcoal at 300℃; Hydrogenation;
TETRAHYDROPYRANE
142-68-7

TETRAHYDROPYRANE

pentane
109-66-0

pentane

Conditions
ConditionsYield
With triethylsilane; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 20h; Reduction;88%
With triethylsilane; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 20h; Reduction;97 % Spectr.
hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

pentane
109-66-0

pentane

Conditions
ConditionsYield
With hydrogen; silica gel; palladium at 330℃;85%
1-penten
109-67-1

1-penten

A

pentane
109-66-0

pentane

B

2-pentene
109-68-2

2-pentene

Conditions
ConditionsYield
With hydrogen; 1-n-butyl-3-methylimidazolium hexafluoroantimonate; [Rh(I)(norbornadiene)(PPh3)2]PF6 In acetone at 30℃; under 750.06 Torr; for 2h;A 83%
B 13%
With hydrogen; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; [Rh(I)(norbornadiene)(PPh3)2]PF6 In acetone at 30℃; under 750.06 Torr;A 25%
B 74%
With C28H25ClNPTi In toluene at 25℃; Reagent/catalyst;A 7%
B 19%
With (iPr4antraphos)Ir(C2H4) at 180℃; for 130h; Inert atmosphere;A 45.5 %Chromat.
B 27.9 %Chromat.
hexanoic acid
142-62-1

hexanoic acid

A

decane
124-18-5

decane

B

1-penten
109-67-1

1-penten

C

pentane
109-66-0

pentane

D

2-pentene
109-68-2

2-pentene

Conditions
ConditionsYield
With potassium hydroxide In water pH=5.4 - 9.4; Concentration; pH-value; Kolbe Electrolysis; Electrochemical reaction;A 82%
B 44%
C 30%
D 26%
With potassium hydroxide In water pH=5.8 - 9; Kolbe Electrolysis; Electrochemical reaction;A 39%
B 14%
C 5%
D 7%
penta-1,3-diene
504-60-9

penta-1,3-diene

pentane
109-66-0

pentane

Conditions
ConditionsYield
With hydrogen; nickel(II) oxide; aluminum oxide at 500℃;80.5%
With hydrogen; nickel(II) oxide; aluminum oxide at 500℃; other catalyst; other temp.;80.5%
With ethanol; nickel at 29 - 35℃; under 25742.8 Torr; Hydrogenation;
With dihydrogen hexachloroplatinate; ethanol; H2PtCl6-(C9H19)3N-(i-C4H9)2AlH-C2H5OH; hydrogen; diisobutylaluminium hydride In toluene at 20℃; under 300.02 Torr; further reagents;
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

1-methoxy-2,4,6-trinitrobenzene
606-35-9

1-methoxy-2,4,6-trinitrobenzene

A

lithium picrate
18390-55-1

lithium picrate

B

pentane
109-66-0

pentane

Conditions
ConditionsYield
In tetrahydrofuran Product distribution; Mechanism; formation of intermediate ς-complex, NMR spectrum of the ς-complex;A 80%
B n/a
1-Pentyne
627-19-0

1-Pentyne

A

(Z)-pent-2-ene
627-20-3

(Z)-pent-2-ene

B

(E)-pent-2-ene
646-04-8

(E)-pent-2-ene

C

1-penten
109-67-1

1-penten

D

pentane
109-66-0

pentane

Conditions
ConditionsYield
With hydrogen; palladium dichloride In N,N-dimethyl-formamide under 18751.5 Torr; for 0.3h; Product distribution; Ambient temperature; various time;A n/a
B n/a
C 78.5%
D 2.4%
With [Ru4(μ-H)4(CO)12] In benzene at 25℃; for 23h; Irradiation;A 10%
B 13%
C 73%
D 4%
With [Ru4(μ-H)4(CO)12]; hydrogen In benzene at 25℃; under 517.1 Torr; for 24h; Irradiation;A 13%
B 10%
C 66%
D 11%
chloroform
67-66-3

chloroform

ethylmagnesium chloride
2386-64-3

ethylmagnesium chloride

A

propane
74-98-6

propane

B

3-ethylpentane
617-78-7

3-ethylpentane

C

pentane
109-66-0

pentane

Conditions
ConditionsYield
With C31H37ClN3NiO2(1-)*Li(1+) In tetrahydrofuran at 25℃; for 0.333333h; Inert atmosphere; Overall yield = 93.4 %;A 6%
B 9.4%
C 78%
With C31H37ClFeN3O2 In tetrahydrofuran at 25℃; for 0.0833333h; Inert atmosphere;
2-Pentyne
627-21-4

2-Pentyne

A

(Z)-pent-2-ene
627-20-3

(Z)-pent-2-ene

B

(E)-pent-2-ene
646-04-8

(E)-pent-2-ene

C

1-penten
109-67-1

1-penten

D

pentane
109-66-0

pentane

Conditions
ConditionsYield
With [Ru4(μ-H)4(CO)12] In benzene at 25℃; for 23h; Irradiation;A 75%
B 1%
C 24%
D n/a
With [Ru4(μ-H)4(CO)12]; hydrogen In benzene at 25℃; under 517.1 Torr; for 24h; Irradiation;A 19%
B 73%
C 2%
D 6%
With [Ru4(μ-H)4(CO)12]; hydrogen In benzene at 25℃; for 24h; Irradiation;A 19%
B 73%
C 2%
D 6%
With hydrogen; dodecacarbonyltetrarhodium(0) at 80℃; under 760 Torr; for 3h; Product distribution; other alkynes, other carbonyl-rhodium catalyst system;A 64 % Chromat.
B 17 % Chromat.
C 2 % Chromat.
D 12 % Chromat.
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

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

A

1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

B

pentan-1-ol
71-41-0

pentan-1-ol

C

pentane
109-66-0

pentane

Conditions
ConditionsYield
With hydrogen; (acetylacetonato)dicarbonylrhodium (l); molybdenum hexacarbonyl In 1,4-dioxane at 150℃; under 75007.5 Torr; for 3h;A 75%
B 19%
C 6%
pentan-1-ol
71-41-0

pentan-1-ol

A

methylbutane
78-78-4

methylbutane

B

pentane
109-66-0

pentane

Conditions
ConditionsYield
With aluminium trichloride; polyethoxysilane (silicone GKZh-94) In nitromethane Product distribution;A 72%
B 23%
(Z)-pent-2-ene
627-20-3

(Z)-pent-2-ene

A

(E)-pent-2-ene
646-04-8

(E)-pent-2-ene

B

pentane
109-66-0

pentane

Conditions
ConditionsYield
With lithium aluminium tetrahydride; water; uranium(IV) chloride 1.) diglyme, 2.) diglyme, 6 h;A 30%
B 70%
C13H21N3

C13H21N3

buta-1,3-diene
106-99-0

buta-1,3-diene

A

C12H15N3

C12H15N3

B

pentane
109-66-0

pentane

Conditions
ConditionsYield
With (2-(4-methoxyphenyl)ethene-1,1-diyl)bis(diphenylphosphane); bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate In 1,4-dioxane; toluene at 160℃; for 72h; Molecular sieve; Glovebox; Sealed tube; regioselective reaction;A 70%
B n/a
1-penten
109-67-1

1-penten

A

(Z)-pent-2-ene
627-20-3

(Z)-pent-2-ene

B

(E)-pent-2-ene
646-04-8

(E)-pent-2-ene

C

pentane
109-66-0

pentane

Conditions
ConditionsYield
With H2Ru4(CO)12 In benzene at 25℃; for 7h; Product distribution; Quantum yield; Irradiation; further pentenes, other periods of time;A n/a
B n/a
C 69%
With hydrogen; palladium; platinum Mechanism; Product distribution; dependence of product distribution on kind of catalyst;
With hydrogen; (CO)12> In dichloromethane at 35℃; under 760 Torr; for 24h; Product distribution; other ruthenium catalysts, other temp., other pressure of H2, various partial pressure of CO, also in the presence of PPh3;
With hydrogen; bis(benzonitrile)palladium(II) dichloride In toluene at 25℃; Product distribution; Kinetics;
With iron pentacarbonyl; hydrogen Product distribution; Irradiation; var. times;
sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

1-Bromopentane
110-53-2

1-Bromopentane

tetramethlyammonium chloride
75-57-0

tetramethlyammonium chloride

A

{(CH3)4N}(1+)*{B11H14}(1-)={(CH3)4N}{B11H14}

{(CH3)4N}(1+)*{B11H14}(1-)={(CH3)4N}{B11H14}

B

pentane
109-66-0

pentane

Conditions
ConditionsYield
In water; diethylene glycol byproducts: NaBr, H2; NaBH4 in diglyme heated to 105°C, n-amyl bromide added to stirred suspn. over 5 h, suspn. allowed to cool, filtered, solids washed with Et2O, combined solns. evapd. residue dissolved in water and Me4NCl added; ppt. filtered and recrystd. from acetone/water;A 67%
B n/a
1-methylbuta-1,3-diene
2004-70-8

1-methylbuta-1,3-diene

A

(Z)-pent-2-ene
627-20-3

(Z)-pent-2-ene

B

(E)-pent-2-ene
646-04-8

(E)-pent-2-ene

C

1-penten
109-67-1

1-penten

D

pentane
109-66-0

pentane

Conditions
ConditionsYield
With hydrogen; palladium dichloride In N,N-dimethyl-formamide under 18751.5 Torr; for 0.116667h; Product distribution; Ambient temperature; various time;A 11.7%
B 62.1%
C 15.3%
D 1.2%
With hydrogen; complex 1 under 684 Torr; for 6h; Product distribution; Variation of complex catalysts, time.;
With hydrogen; Pd-containing polymer In methanol at 20℃; Product distribution; catalytic properties of palladium fixed on poly(m- and p-)hydroxyphenylbenzoxazoleterephthalamides, hydrogenation and isomerization of olefins;
With hydrogen; <2> In dichloromethane for 5h; Product distribution; other alkene;
2-bromopentane
107-81-3

2-bromopentane

octylmagnesium bromide
17049-49-9

octylmagnesium bromide

A

4-methyldodecane
6117-97-1

4-methyldodecane

B

pentane
109-66-0

pentane

C

2-pentene
109-68-2

2-pentene

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; cobalt(II) chloride; lithium iodide In tetrahydrofuran at 10℃; for 1h; Inert atmosphere; chemoselective reaction;A 62%
B n/a
C n/a
propane
74-98-6

propane

A

ethane
74-84-0

ethane

B

Isobutane
75-28-5

Isobutane

C

n-butane
106-97-8

n-butane

D

pentane
109-66-0

pentane

Conditions
ConditionsYield
silica/alumina-supp. -O-W[(C-tBu)(-CH2-tBu)2] at 150℃; under 600 Torr; for 120h; Product distribution; Further Variations:; Catalysts;A 61.7%
B 3.4%
C 25.7%
D 5.5%
tetrachloromethane
56-23-5

tetrachloromethane

ethylmagnesium chloride
2386-64-3

ethylmagnesium chloride

A

3-ethylpentane
617-78-7

3-ethylpentane

B

pentane
109-66-0

pentane

Conditions
ConditionsYield
With C31H37ClN3NiO2(1-)*Li(1+) In tetrahydrofuran at 25℃; for 0.333333h; Inert atmosphere; Overall yield = 100 %;A 42.8%
B 57.2%
dichloromethane
75-09-2

dichloromethane

ethylmagnesium chloride
2386-64-3

ethylmagnesium chloride

A

propene
187737-37-7

propene

B

n-butane
106-97-8

n-butane

C

pentane
109-66-0

pentane

Conditions
ConditionsYield
With C31H37ClN3NiO2(1-)*Li(1+) In tetrahydrofuran at 25℃; for 0.333333h; Inert atmosphere; Overall yield = 91 %;A 14%
B 20%
C 57%
pentane
109-66-0

pentane

decane
124-18-5

decane

Conditions
ConditionsYield
With di-tert-butyl peroxide; iodine100%
HOC6H3ClCH2N(CH3)C2H4N(CH3)CH2C6H2(C(CH3)3)2OH
1129682-90-1

HOC6H3ClCH2N(CH3)C2H4N(CH3)CH2C6H2(C(CH3)3)2OH

zirconium(IV) tert-butoxide

zirconium(IV) tert-butoxide

pentane
109-66-0

pentane

[(OC6H3ClCH2N(CH3)C2H4N(CH3)CH2C6H2(C(CH3)3)2O)Zr(OC(CH3)3)2]*0.5C5H12

[(OC6H3ClCH2N(CH3)C2H4N(CH3)CH2C6H2(C(CH3)3)2O)Zr(OC(CH3)3)2]*0.5C5H12

Conditions
ConditionsYield
In diethyl ether byproducts: (CH3)3COH; (N2); glovebox; soln. of ligand in ether was added to soln. of Zr complex in ether; stirred at room temp. for 2 h; solvent removed (vac.); washed (pentane); solvent removed (vac.); elem. anal.;100%
HOC6H2Cl2CH2N(CH3)C2H4N(CH3)CH2C6H2(C10H15)(CH3)OH
1129682-97-8

HOC6H2Cl2CH2N(CH3)C2H4N(CH3)CH2C6H2(C10H15)(CH3)OH

zirconium(IV) tert-butoxide

zirconium(IV) tert-butoxide

pentane
109-66-0

pentane

[(OC6H2Cl2CH2N(CH3)C2H4N(CH3)CH2C6H2(C10H15)(CH3)O)Zr(OC(CH3)3)2]*C5H12

[(OC6H2Cl2CH2N(CH3)C2H4N(CH3)CH2C6H2(C10H15)(CH3)O)Zr(OC(CH3)3)2]*C5H12

Conditions
ConditionsYield
In diethyl ether byproducts: (CH3)3COH; (N2); glovebox; soln. of ligand in ether was added to soln. of Zr complex in ether; stirred at room temp. for 2 h; solvent removed (vac.); washed (pentane); solvent removed (vac.); elem. anal.;100%
N,N-bis(3,4-dimethyl-2-hydroxybenzyl)-N',N'-dimethylethylenediamine
244005-01-4

N,N-bis(3,4-dimethyl-2-hydroxybenzyl)-N',N'-dimethylethylenediamine

C14H6(C4H9)4H2NC3H7O2Ti(OC3H7)2
359902-97-9

C14H6(C4H9)4H2NC3H7O2Ti(OC3H7)2

pentane
109-66-0

pentane

(C14H6(CH3)4H2NC2H4N(CH3)2O2)(C14H6(C4H9)4H2NC3H7O2)Ti*C5H12

(C14H6(CH3)4H2NC2H4N(CH3)2O2)(C14H6(C4H9)4H2NC3H7O2)Ti*C5H12

Conditions
ConditionsYield
In diethyl ether the mixt. in ether was stirred for 2 h at room temp. under N2; volatiles were removed under reduced pressure; elem. anal.;99%
HOC6H2Br2CH2N(CH3)C2H4N(CH3)CH2C6H2(C(CH3)3)2OH
1129682-92-3

HOC6H2Br2CH2N(CH3)C2H4N(CH3)CH2C6H2(C(CH3)3)2OH

zirconium(IV) tert-butoxide

zirconium(IV) tert-butoxide

pentane
109-66-0

pentane

[(OC6H2Br2CH2N(CH3)C2H4N(CH3)CH2C6H2(C(CH3)3)2O)Zr(OC(CH3)3)2]*C5H12

[(OC6H2Br2CH2N(CH3)C2H4N(CH3)CH2C6H2(C(CH3)3)2O)Zr(OC(CH3)3)2]*C5H12

Conditions
ConditionsYield
In diethyl ether byproducts: (CH3)3COH; (N2); glovebox; soln. of ligand in ether was added to soln. of Zr complex in ether; stirred at room temp. for 2 h; solvent removed (vac.); washed (pentane); solvent removed (vac.); elem. anal.;99%
HOC6H2I2CH2N(CH3)C2H4N(CH3)CH2C6H2(C10H15)(CH3)OH
1129683-02-8

HOC6H2I2CH2N(CH3)C2H4N(CH3)CH2C6H2(C10H15)(CH3)OH

zirconium(IV) tert-butoxide

zirconium(IV) tert-butoxide

pentane
109-66-0

pentane

[(OC6H2I2CH2N(CH3)C2H4N(CH3)CH2C6H2(C10H15)(CH3)O)Zr(OC(CH3)3)2]*C5H12

[(OC6H2I2CH2N(CH3)C2H4N(CH3)CH2C6H2(C10H15)(CH3)O)Zr(OC(CH3)3)2]*C5H12

Conditions
ConditionsYield
In diethyl ether byproducts: (CH3)3COH; (N2); glovebox; soln. of ligand in ether was added to soln. of Zr complex in ether; stirred at room temp. for 2 h; solvent removed (vac.); washed (pentane); solvent removed (vac.); elem. anal.;99%
[(dimethyl-bis(4-tert-butyl-2-pyridyl)borate)Pt(CH3)2]Na
1198747-49-7

[(dimethyl-bis(4-tert-butyl-2-pyridyl)borate)Pt(CH3)2]Na

water
7732-18-5

water

pentane
109-66-0

pentane

[(dimethyl-bis(4-tert-butyl-2-pyridyl)borate)PtH(1-pentene)]
1198747-51-1

[(dimethyl-bis(4-tert-butyl-2-pyridyl)borate)PtH(1-pentene)]

Conditions
ConditionsYield
In not given byproducts: NaOH; 3 equiv. H2O, room temp., 5 min;99%
4,4'-bis(P-((S,S)-[2,6-bis(4'-isopropyl-2'-oxazolinyl)phenyl]gold(I))(diphenylphosphino))biphenyl*(benzene)

4,4'-bis(P-((S,S)-[2,6-bis(4'-isopropyl-2'-oxazolinyl)phenyl]gold(I))(diphenylphosphino))biphenyl*(benzene)

niobium pentachloride
10026-12-7

niobium pentachloride

pentane
109-66-0

pentane

benzene
71-43-2

benzene

A

4,4'-bis[P-(chlorogold(I))diphenylphosphino]biphenyl
528522-58-9

4,4'-bis[P-(chlorogold(I))diphenylphosphino]biphenyl

B

(S,S)-[2,6-bis(4'-isopropyl-2'-oxazolinyl)phenyl]niobium(V) dichloride oxide dimer*(benzene)*(pentane)

(S,S)-[2,6-bis(4'-isopropyl-2'-oxazolinyl)phenyl]niobium(V) dichloride oxide dimer*(benzene)*(pentane)

Conditions
ConditionsYield
In tetrahydrofuran under N2; soln. of Au complex in THF added to solid NbCl5; stirred at room temp. overnight; volatiles removed in vac.; dissolved in benzene; centrifuged; decanted; concd. in vac.; crystd. from benzene-pentane; elem. anal.;A 99%
B 76%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

[[Li(THF)2][(CO)3CrGe9[Si(SiMe3)3)3]]2

[[Li(THF)2][(CO)3CrGe9[Si(SiMe3)3)3]]2

pentane
109-66-0

pentane

[(TMEDA)2Li][(CO)3CrGe9[Si(SiMe3)3)3]*0.5(pentane)

[(TMEDA)2Li][(CO)3CrGe9[Si(SiMe3)3)3]*0.5(pentane)

Conditions
ConditionsYield
In pentane (N2) to soln. Cr-Ge complex in pentane TMEDA was added at room temp., stored at 6°C overnight;99%
N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

[(THF)3Li][(CO)3CrGe9[Si(SiMe3)3)3]*pentane

[(THF)3Li][(CO)3CrGe9[Si(SiMe3)3)3]*pentane

pentane
109-66-0

pentane

[(TMEDA)2Li][(CO)3MoGe9[Si(SiMe3)3)3]*0.5(pentane)

[(TMEDA)2Li][(CO)3MoGe9[Si(SiMe3)3)3]*0.5(pentane)

Conditions
ConditionsYield
In pentane (N2) to soln. Mo-Ge complex in pentane TMEDA was added at room temp., stored at 6°C overnight;99%
(Rsi)-cyclohexyldimethoxy[(2S)-2-(methoxymethyl)-1-pyrrolidinyl]silane

(Rsi)-cyclohexyldimethoxy[(2S)-2-(methoxymethyl)-1-pyrrolidinyl]silane

tert.-butyl lithium
594-19-4

tert.-butyl lithium

pentane
109-66-0

pentane

C34H72Li2N2O4Si4*C5H12

C34H72Li2N2O4Si4*C5H12

Conditions
ConditionsYield
at -80 - -30℃; for 72h; Inert atmosphere; Schlenk technique;99%
2,2,2-trichloroethyl 2-(4-bromophenyl)-2-diazoacetate
1641528-26-8

2,2,2-trichloroethyl 2-(4-bromophenyl)-2-diazoacetate

pentane
109-66-0

pentane

2,2,2-trichloroethyl (2S,3R)-2-(4-bromophenyl)-3-methylhexanoate

2,2,2-trichloroethyl (2S,3R)-2-(4-bromophenyl)-3-methylhexanoate

Conditions
ConditionsYield
With Rh2[R-3,5-di(p-tBuC6H4)-triphenylcyclopropanecarboxylate]4 Reagent/catalyst; Reflux; stereoselective reaction;99%
perfluorophenyl azide
1423-15-0

perfluorophenyl azide

trityl tetrafluoroborate
341-02-6

trityl tetrafluoroborate

tris-(o-tolyl)phosphine
6163-58-2

tris-(o-tolyl)phosphine

pentane
109-66-0

pentane

C46H36F5N3P(1+)*C24BF20(1-)*0.5C5H12

C46H36F5N3P(1+)*C24BF20(1-)*0.5C5H12

Conditions
ConditionsYield
Stage #1: perfluorophenyl azide; trityl tetrafluoroborate; tris-(o-tolyl)phosphine In dichloromethane at 20℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox;
Stage #2: pentane
99%
pentane
109-66-0

pentane

methylbutane
78-78-4

methylbutane

Conditions
ConditionsYield
With hydrogen under 15001.5 Torr; Catalytic behavior; Reagent/catalyst; Temperature; chemoselective reaction;98.5%
With hydrogen at 250℃; under 760.051 Torr; Reagent/catalyst; Temperature;73.2%
With hydrogen; Pd3(PW12O40)2 at 179.9℃;39.5%
15-crown-5
33100-27-5

15-crown-5

Na[U(N(SiMe3)2)(OC(=CH2)SiMe2NSiMe3)2(N3)]
1331740-29-4

Na[U(N(SiMe3)2)(OC(=CH2)SiMe2NSiMe3)2(N3)]

pentane
109-66-0

pentane

Na(C10H20O5)[U(N3)(NSi2C6H18)(COCH2Si(CH3)2N(Si(CH3)3))2]*0.5C5H12

Na(C10H20O5)[U(N3)(NSi2C6H18)(COCH2Si(CH3)2N(Si(CH3)3))2]*0.5C5H12

Conditions
ConditionsYield
In pentane Ar; U compd. and ligand (1:1 molar ratio), stirred for 12 at 20°C; filtered, evapd., elem. anal.;98%
bis[2-(trifluoromethyl)propyl]-2,2'-bipyridine-3,3'-dicarboxylate

bis[2-(trifluoromethyl)propyl]-2,2'-bipyridine-3,3'-dicarboxylate

C18H8Cl2F12N2O4Pd

C18H8Cl2F12N2O4Pd

sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate
79060-88-1

sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate

pentane
109-66-0

pentane

C36H16F24N4O8Pd(2+)*2C32H12BF24(1-)*3C5H12

C36H16F24N4O8Pd(2+)*2C32H12BF24(1-)*3C5H12

Conditions
ConditionsYield
Stage #1: bis[2-(trifluoromethyl)propyl]-2,2'-bipyridine-3,3'-dicarboxylate; C18H8Cl2F12N2O4Pd; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In dichloromethane at 45℃; for 3h;
Stage #2: pentane
98%
tetrahydrofuran
109-99-9

tetrahydrofuran

[Ph(pyrazol-1-yl)B(μ-NH(Me))(μ-pyrazol-1-yl)B(pyrazol-1-yl)Ph]

[Ph(pyrazol-1-yl)B(μ-NH(Me))(μ-pyrazol-1-yl)B(pyrazol-1-yl)Ph]

methylmagnesium chloride
676-58-4

methylmagnesium chloride

pentane
109-66-0

pentane

A

MgCl(tetrahydrofuran)(x)[Ph(pyrazol-1-yl)B(μ-N(Me))(μ-pyrazol-1-yl)B(pyrazol-1-yl)Ph]

MgCl(tetrahydrofuran)(x)[Ph(pyrazol-1-yl)B(μ-N(Me))(μ-pyrazol-1-yl)B(pyrazol-1-yl)Ph]

Mg2(μ-Cl)2(tetrahydrofuran)[Ph(pyrazol-1-yl)B(μ-N(Me))(μ-pyrazol-1-yl)B(pyrazol-1-yl)Ph]2*pentane
1220508-55-3

Mg2(μ-Cl)2(tetrahydrofuran)[Ph(pyrazol-1-yl)B(μ-N(Me))(μ-pyrazol-1-yl)B(pyrazol-1-yl)Ph]2*pentane

Conditions
ConditionsYield
In tetrahydrofuran under N2 atm. using Schlenk techniques; stirred soln. of borate ligand in THF was treated at -78°C with soln. of MeMgCl in THF; mixt. allowed to warm to room temp.; stirred overnight; soln. concd. (vac.); layered with pentane; crystals are formed; mother liq. decanted; dried (vac.);A 97%
B n/a
(2-methylallyl)palladium-chloride dimer

(2-methylallyl)palladium-chloride dimer

1-diphenylphosphino-1'-(N-[(methoxycarbonyl)methyl]carbamoyl)ferrocene
1160484-10-5

1-diphenylphosphino-1'-(N-[(methoxycarbonyl)methyl]carbamoyl)ferrocene

pentane
109-66-0

pentane

[(η3-C3H4Me)PdCl((Ph2PC5H4)Fe(C5H4C(O)NHCH2CO2Me)-κP)2]ClO4*0.5C5H12

[(η3-C3H4Me)PdCl((Ph2PC5H4)Fe(C5H4C(O)NHCH2CO2Me)-κP)2]ClO4*0.5C5H12

Conditions
ConditionsYield
In chloroform byproducts: CH3CN; (Ar); exclusion of direct daylight; soln. of Fe complex (2 equiv.) in CHCl3 was added to Pd complex (1 equiv.); stirred at room temp. for 1 h; poured into pentane; kept at -18°C overnight; filtered; washed (pentane); dried (vac.); elem. anal.;97%
N,N'-bis(2-hydroxy-3,5-di tertiarybutylbenzyl)homopiperazine
527672-96-4

N,N'-bis(2-hydroxy-3,5-di tertiarybutylbenzyl)homopiperazine

pentane
109-66-0

pentane

C82H132Li4N4O7

C82H132Li4N4O7

Conditions
ConditionsYield
Stage #1: N,N'-bis(2-hydroxy-3,5-di tertiarybutylbenzyl)homopiperazine With n-butyllithium In tetrahydrofuran at 20℃; for 72h; Inert atmosphere; Schlenk technique;
Stage #2: pentane Inert atmosphere; Schlenk technique;
97%
1,4-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-1,4-diazacycloheptane
503540-53-2

1,4-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-1,4-diazacycloheptane

pentane
109-66-0

pentane

C70H108Li4N4O7

C70H108Li4N4O7

Conditions
ConditionsYield
Stage #1: 1,4-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-1,4-diazacycloheptane With n-butyllithium In tetrahydrofuran at 20℃; for 72h; Inert atmosphere; Schlenk technique;
Stage #2: pentane Inert atmosphere; Schlenk technique;
97%
C84H84CeLi3O12

C84H84CeLi3O12

pentane
109-66-0

pentane

pentane

pentane

Conditions
ConditionsYield
Stage #1: C84H84CeLi3O12 With trityl chloride In tetrahydrofuran at 20℃; for 2h;
Stage #2: pentane
97%
2-(3-bromopropyl)isoindole-1,3-dione
5460-29-7

2-(3-bromopropyl)isoindole-1,3-dione

1-lithio-2-tert-butyldimethylsilyl-1,2-dicarba-closo-dodecaborane(12)
361544-93-6

1-lithio-2-tert-butyldimethylsilyl-1,2-dicarba-closo-dodecaborane(12)

pentane
109-66-0

pentane

2-(3'-tert-butyldimethylsiloxy-1'-oxo-1',3'-dihydroisoindol-3'-yl)-1,2'-propano-1,2-dicarba-closo-dodecaborane*0.5(pentane)

2-(3'-tert-butyldimethylsiloxy-1'-oxo-1',3'-dihydroisoindol-3'-yl)-1,2'-propano-1,2-dicarba-closo-dodecaborane*0.5(pentane)

Conditions
ConditionsYield
In diethyl ether; benzene cooled soln. (0°C) of B compd. in benzene-Et2O treated dropwise with benzene-Et2O soln. of C6H4(CO)2N(CH2)3Br (molar ratio 1:1.08); warmed to room temp.; gradually brought to reflux; refluxed for 2 d; solvent removed on rotary evaporator; treated with MeOH; cooled (-10°C) overnight; filtered; solid washed with chilled MeOH; dried in vac.; purified by slow evapn. of pentane-Et2O soln.; elem. anal.;95%
n-propylamino-N,N-bis(2-methylene-4,6-di-tert-butylphenol)
267428-18-2

n-propylamino-N,N-bis(2-methylene-4,6-di-tert-butylphenol)

[Ti(OCH(CH3)2)2N(CH3)2C2H4N(OC6H2(CH3)2CH2)2]
244005-02-5

[Ti(OCH(CH3)2)2N(CH3)2C2H4N(OC6H2(CH3)2CH2)2]

pentane
109-66-0

pentane

(C14H6(CH3)4H2NC2H4N(CH3)2O2)(C14H6(C4H9)4H2NC3H7O2)Ti*C5H12

(C14H6(CH3)4H2NC2H4N(CH3)2O2)(C14H6(C4H9)4H2NC3H7O2)Ti*C5H12

Conditions
ConditionsYield
In toluene 2 h at 110°C in toluene in a sealed tube;95%
chloroform
67-66-3

chloroform

trans-RuCl2(PPh3)(κ3-L(3))*(chloroform)*(diethyl ether)

trans-RuCl2(PPh3)(κ3-L(3))*(chloroform)*(diethyl ether)

pentane
109-66-0

pentane

trans-RuCl2(PPh3)(κ3-L(4))*(chloroform)*(pentane)

trans-RuCl2(PPh3)(κ3-L(4))*(chloroform)*(pentane)

Conditions
ConditionsYield
With H2O2 In chloroform under N2 or in vac.; a soln. of H2O2 (0.238 mmol) was added dropwise to a soln. of Ru-contg. compd. (0.198 mmol) in chloroform; the mixt. was stirred at room temp. for 12 h before it was filtered; the filtrate was evapd. to dryness in vac.; the residue was washed with diethyl ether and crystd. in a chloroform-pentane mixt.; elem. anal.; (31)P NMR spectra monitoring;95%

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109-66-0Relevant articles and documents

Synthesis of a Highly Active Superacid of Platinum-supported Zirconia for Reaction of Butane

Hino, Makoto,Arata, Kazushi

, p. 789 - 790 (1995)

A highly active superacid of 8 masspercent Pt-supported ZrO2 for the skeletal isomerization of butane to isobutane is obtained by impregnating zirconia gel with 0.5 mol dm-3 H2SO4 followed by drying, impregnating the sulfated gel with a solution of H2PtCl6, and finally calcining in air at 600 deg C.

Kurras,Otto

, p. 479 (1965)

LE COMPLEXE 2> CATALYSEUR HOMOGENE D'HYDROGENATION ET D'HYDROSILYLATION D'OLEFINES ET D'ALDEHYDES ET CETONES α,β-INSATURES

Rumin, R.

, p. 351 - 356 (1983)

The chloro-bridged platinum(II) complex dichlorobis(2,4,6-trimethylpyridine)platinum was found to be an active catalyst for homogeneous hydrogenation and hydrosilylation of olefins and α,β-unsaturated aldehydes and ketones at room temperature and under atmospheric pressure.Hydrosilylation of terminal olefins can be achieved with dimethylphenylsilane and a catalyst/reactant ratio of 10-6/1.This complex is the first example of a platinum(II) compound containing pyridine ligands having good catalytic activity possibilities.

Some Diels-Alder reactions of trimethoxysilylpropylcyclopentadiene and the synthesis of a silica-supported 4,5-dicyanonorbornenepalladium complex

Adeleke, J. A.,Booth, B. L.

, p. 223 - 230 (1988)

Trimethoxysilylpropylcyclopentadiene reacts with the electron-deficient acetylenes, RO2CC2CO2R (R=Me, Et) and olefins R1CH=CHR2 (R1=H, R2=SOPh; R1=R2=P(O)Ph2, R1=R2=CN) to give the corresponding Diels-Alder adducts.The compounds CHCl=CHCl and E-Ph2P(S)CH=CHP(S)Ph2 failed to react under similar conditions.The adduct from fumarodinitrile has been used to synthesise a silica-anchored bis-nitrile palladium chloride complex, which catalyses the isomerisation of pent-1-ene.

Understanding ketone hydrodeoxygenation for the production of fuels and feedstocks from biomass

King, Amanda E.,Brooks, Ty J.,Tian, Yong-Hui,Batista, Enrique R.,Sutton, Andrew D.

, p. 1223 - 1226 (2015)

Although we can efficiently convert bioderived furans into linear alkanes, the most energy-intensive step in this approach is the hydrodeoxygenation of the intermediate polyketone. To fully understand this process, we have examined the hydrodeoxygenation of a model compound, 3-pentanone, which allows us to follow this process stepwise using Pd/C, H2 (200 psi), and La(OTf)3 in acetic acid to remove the oxygen atom at temperatures between 25 and 200 C. We have found that ketone reduction to an alcohol is followed by acetoxylation, which provides a more facile route to C-O bond cleavage relative to the parent alcohol. (Chemical Presented).

Oligomerisation of alkenes by radical initiation

Cowley, Michele

, p. 286 - 288 (2007)

The use of di-tert-butyl peroxide (DTBP) as initiator for the radical oligomerisation of 1-octene and pentene, typical Fischer-Tropsch-derived products, was studied in the temperature range 100-200°C. Using this approach, the favourable product distributi

Laser photocatalytic isomerization and hydrogenation of olefins in the gas phase

Whetten, Robert L.,Fu, Ke-Jian,Grant, Edward R.

, p. 3769 - 3770 (1982)

-

Rare-earth metal allyl and hydrido complexes supported by an (NNNN)-type macrocyclic ligand: Synthesis, structure, and reactivity toward biomass-derived furanics

Abinet, Elise,Martin, Daniel,Standfuss, Sabine,Kulinna, Heiko,Spaniol, Thomas P.,Okuda, Jun

, p. 15014 - 15026 (2011)

The preparation and characterization of a series of neutral rare-earth metal complexes [Ln(Me3TACD)(η3-C3H 5)2] (Ln=Y, La, Ce, Pr, Nd, Sm) supported by the 1,4,7-trimethyl-1,4,7,10-tetraazacyclododecane anion (Me3TACD -) are reported. Upon treatment of the neutral allyl complexes [Ln(Me3TACD)(η3-C3H5) 2] with Bronsted acids, monocationic allyl complexes [Ln(Me3TACD)(η3-C3H5)(thf) 2][B(C6X5)4] (Ln=La, Ce, Nd, X=H, F) were isolated and characterized. Hydrogenolysis gave the hydride complexes [Ln(Me3TACD)H2]n (Ln=Y, n=3; La, n=4; Sm). X-ray crystallography showed the lanthanum hydride to be tetranuclear. Reactivity studies of [Ln(Me3TACD)R2]n (R=η3-C3H5, n=0; R=H, n=3,4) towards furan derivatives includes hydrosilylation and deoxygenation under ring-opening conditions.

Catalytic consequences of particle size and chloride promotion in the ring-opening of cyclopentane on Pt/Al2O3

Shi, Hui,Gutiérrez, Oliver Y.,Yang, Hao,Browning, Nigel D.,Haller, Gary L.,Lercher, Johannes A.

, p. 328 - 338 (2013)

Ring-opening of cyclopentane on alumina-supported Pt particles was studied as a function of Pt particle size in the presence of different Cl contents. With catalysts prepared from a Cl-free precursor, measured turnover rates increased monotonically with increasing Pt particle size (1-15 nm). On catalysts derived from a Cl-containing precursor, the turnover rates fell into two separate trends with the change of Pt particle size, depending on the extent of Cl removal by increasing thermal treatment temperature. In both cases, catalytic activity increased with increasing particle size in the examined ranges of dispersions (D = 0.7-1.0 and 0-0.6) and for both series of catalysts, the apparent activation energies were higher on large Pt particles than on small ones, with only small differences in the reaction orders for H2 and cyclopentane on particles of widely varying average sizes. Therefore, the effect of particle size on the turnover rates stems mainly from intrinsic rate constants, rather than from coverage effects. The relative adsorption coefficients of toluene and benzene indicated lower electron densities at the surface Pt atoms in the catalysts prepared from the Cl-containing precursor than in those from the Cl-free precursor. This subtle electron deficiency, which seems not to stem from the local Cl enrichment near Pt, affects both the concentration of chemisorbed hydrogen under reaction conditions and the barrier for C-C bond cleavage. The Cl postintroduced to the catalyst, in contrast, does not induce a similarly positive effect.

Activation of alkyl C-F Bonds by B(C6F5)3: Stoichiometric and catalytic transformations

Caputo, Christopher B.,Stephan, Douglas W.

, p. 27 - 30 (2012)

The Lewis acid B(C6F5)3 is shown to activate a series of alkyl fluorides. In stoichiometric reactions, treatment of sterically demanding phosphines with B(C6F5) 3/alkyl fluorides gives phosphonium fluoroborate salts while treatment of B(C6F5)3/alkyl fluorides with the salts [tBu3PX][XB(C6F5)3] (X = H, PhS) gives the alkane and the salt byproduct [tBu3PX][FB(C 6F5)3]. These fluoroalkanes are also catalytically converted to the corresponding alkanes by reaction of the fluoroalkane and Et3SiH using B(C6F5)3 as the catalyst.

Direct Observation of Ion-Pair Dynamics

Masnovi, J. M.,Kochi, J. K.

, p. 7880 - 7893 (1985)

The intimate ion pair is spontaneously generated by the change-transfer excitation of the electron donor-acceptor complex of anthracene donors (A) and tetranitromethane (TNO2) with a 25-ps laser pulse.The kinetics of the subsequent ion-pair decay to the adduct (i.e., -> AT) is followed spectroscopically over the separate picosecond, nanosecond, and microsecond time domains, each with a different laser-flash system.Three distinctive rate profiles are observed: (a) the picosecond decay following first-order kinetics (kI), the nanosecond decay also following first-order but slower kinetics (kII), and the microsecond decay following second-order kinetics (kIII).The experimental rate constants kI, kII, and kIII are associated with the relaxation of the intimate or tight ion pair , the solvent-separated or loose ion pair , and the free ions , respectively, as originally formulated by Winstein and co-workers for solvolysis mechanisms.These kinetics data together with the measurements of the fractional partitioning of ion pairs allow all the microscopic rate constsnts relevant to ion pair dynamics to be separately evaluated.The Winstein ion-pair formulation is substantiated by the observation and quantitative treatment of the "common-ion" and "special" salt effects.The role of solvent is underscored by the unique kinetics responses of reactive and persistent cations derived from various 9-substituted and 9,10-disubstituted anthracenes, respectively, with changes in the polarity of the medium from benzene and dichloromethane to acetonitrile.The overall importance of charge annihilation and separation in the microdynamics of transient ion pairs is underscored by a comparison with the bimolecular kinetics of radical-radical interaction measured under comparable conditions.

Push-pull mechanism of hydrodenitrogenation over silica-supported MoP, WP, and MoS2 hydroprocessing catalysts

Clark,Wang,Deck,Oyama

, p. 116 - 126 (2002)

The mechanism of liquid-phase catalytic hydrodenitrogenation at 3.1 MPa on silica-supported molybdenum phosphide, MoP/SiO2, and tungsten phosphide, WP/SiO2, was studied using a series of pentylamines of different structures. The reactivity pattern suggested that removal of nitrogen occurred primarily by an E2 elimination mechanism involving acidic and base sites on the catalyst surfaces in a push-pull process. Infrared spectroscopy and temperature-programmed reaction studies of ethylamine indicated that alkyl ammonium species formed on Bronsted acid sites were intermediates in the reaction. Similar results were obtained with a reference MoS2/SiO2 sample tested at the same conditions. This suggested that sulfur was probably present on the active surface and assisted in the removal of sulfur.

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Craig

, p. 1006,1011 (1943)

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Correlating heat of adsorption of CO to reaction selectivity: Geometric effects vs electronic effects in neopentane isomerization over Pt and Pd catalysts

Childers, David,Saha, Arindom,Schweitzer, Neil,Rioux, Robert M.,Miller, Jeffrey T.,Meyer, Randall J.

, p. 2487 - 2496 (2013)

Silica-supported Pt and Pd nanoparticles from 1 to 10 nm in diameter were evaluated for neopentane conversion (hydrogenolysis and isomerization). Characterization of the catalysts was conducted utilizing scanning transmission electron microscopy (STEM), diffuse reflectance infrared Fourier transform spectroscopy (DRIFTS) of adsorbed CO, X-ray absorption spectroscopy (XAS), and isothermal calorimetry of CO adsorption to determine how geometric or electronic structure effects can explain changes in reactivity. Isomerization selectivity of Pt was much higher than Pd for all particle sizes. There is a pronounced effect of particle size on selectivity, with the highest isomerization selectivity achieved over catalysts containing the largest particle size for both Pt (57%) and Pd (26%) catalysts. For both Pd and Pt catalysts, DRIFTS showed a decrease in the ratio of linear-to-bridge bonded CO with particle size, while isothermal calorimetry of CO adsorption shows that both Pt and Pd enthalpies of adsorption decrease with increasing particle size. The isomerization selectivity was found to correlate inversely with the strength of CO adsorption for all catalysts suggesting that the chemisorption energy and not the particle size, coordination geometry, or ensemble size is the most important factor for increasing the isomerization selectivity.

Kinetic and FTIR studies of 2-methyltetrahydrofuran hydrodeoxygenation on Ni2P/SiO2

Cho, Ara,Kim, Hosoo,Iino, Ayako,Takagaki, Atsushi,Ted Oyama

, p. 151 - 161 (2014)

The hydrodeoxygenation of 2-methyltetrahydrofuran (2-MTHF) at a medium pressure of 0.5 MPa is studied over a Ni2P/SiO2 catalyst. Contact time studies show the formation of n-pentanal, 1-pentanol, 2-pentanone, 2-pentanol, and 2-pentene, as reaction intermediates and the production of pentane and butane as major products. The results are consistent with adsorption of 2-MTHF followed by rate-determining ring-opening to form either 1-pentoxide or 2-pentoxide alkoxide intermediates. Subsequent hydrogen-transfer steps produce the various intermediates, a decarbonylation step of the pentanal forms n-butane and CO, and further hydrodeoxygenation steps result in n-pentane. Fitting of the results using a rake mechanism that considers adsorbed intermediates gives excellent agreement with experimental data, and agrees with a simulation with a simpler first-order model. The more detailed rake analysis indicates that the surface species from the 1-pentoxide intermediate are ten-fold more plentiful than those produced from the 2-pentoxide intermediate. In situ infrared measurements support this reaction mechanism.

The hydrogenation of 1,3-pentadiene over an alumina-supported palladium catalyst: An FTIR study

Opara, Elaine,Lundie, David T.,Lear, Timothy,Sutherland, Iain W.,Parker, Stewart F.,Lennon, David

, p. 5588 - 5595 (2004)

The hydrogenation of a mixture of cis- and trans-1,3-pentadiene over a 1% Pd/Al2O3 catalyst at 303 K has been studied using infrared spectroscopy to monitor the changes in the composition of the gas phase over the catalyst as a function of time. The reaction is seen to occur as a consecutive process, with the terminal double bond hydrogenated in advance of the internal double bond. Vibrational assignments have been confirmed through ancillary calculations for a number of C5 molecules. The reaction profile is consistent with the catalyst presenting two distinct reaction sites: hydrogenation of the terminal double bond occurs at Site α, whilst Site β is responsible for hydrogenation of the internal double bond. Trans-pent-2-ene is identified as the only reaction intermediate. From comparative studies of the hydrogenation of pentenes over the catalyst, the absence of any cis-pent-2-ene in the reaction mixture is tentatively attributed to cis-1,3-pentadiene isomerising at Site α to form trans-1,3-pentadiene. The effect of toluene-d8 to act as a chemical modifier was also investigated and shown to selectively poison Site β Site α being unperturbed.

HYDROGENATION OF PENTYNES AND OF PENTADIENES CATALYSED BY Ru3(CO)12, Fe3(CO)12 AND MIXED METAL Ru-Fe DODECACARBONYLS SUPPORTED ON γ-Al2O3

Lausarot, P. Michelin,Vaglio, G. A.,Valle, M.

, p. 233 - 238 (1984)

Hydrogenation under mild conditions of 1- and 2-pentyne and of 1,3-cis- and 1,3-trans-pentadiene catalysed by Ru3(CO)12, FeRu2(CO)12, Fe2Ru(CO)12 and Fe3(CO)12 in toluene solutions or anchored on γ-Al2O3 has been studied.For all the systems examined, catalytic activity was highest for Ru3(CO)12-containing catalysts and lowest for Fe3(CO)12-containing ones.For mixed metal catalysts, activity decreased with increasing number of Fe atoms in the dodecacarbonyls.Anchorage of the clusters to γ-Al2O3 produced catalysts which were less active towards hydrogenation of 1- and 2-pentyne and more active towards hydrogenation of 1,3-cis- and 1,3-trans-pentadiene, but had no effect on product distribution.

Using modifiers to specify stereochemistry and enhance selectivity and activity in palladium-catalysed, liquid phase hydrogenation of alkynes

Garcia, Paloma E.,Lynch, Ailsa S.,Monaghan, Andy,Jackson, S. David

, p. 548 - 551 (2011)

Enhancing selectivity is a key parameter in green chemistry. In this study, we have examined the liquid phase hydrogenation of alkynes over a palladium catalyst and used modifiers to enhance selectivity and activity. The reactions studied were the hydrogenation of 1-pentyne and 2-pentyne. Five modifiers were used, pentane nitrile and its respective amine, pentyl amine, 3-phenyl propionitrile and its respective amine, 3-phenyl propylamine and trans-cinnamonitrile. These modifiers were not hydrogenated under reaction conditions. It was possible to obtain high (>90%) selectivities to 1-pentene and cis-2-pentene at high conversion. The effect on rate was dependent upon the modifier and the alkyne. The effect of the modifier was the same whether added with or before the reactants. Competitive reactions confirmed that terminal alkynes and internal alkynes are hydrogenated on separate sites and do not interfere and that the modifier influences each separately.

Preparation of the Ru/HZSM-5 catalyst and its catalytic performance for the 2-pentanone hydrodeoxygenation reaction

An, Hualiang,Wang, Yanji,Xi, Xi,Yang, Ye,Zhao, Xinqiang

, p. 17692 - 17698 (2021)

Levulinic acid is an ideal model compound for complex oxygenated components in bio-oil. To assist the understanding of its hydrodeoxygenation (HDO) performance, it is necessary to investigate separately the HDO property of the ketonic carbonyl group and carboxyl group. Herein, 2-pentanone was selected as a model to study the HDO property of the ketonic carbonyl group. The Ru/HZSM-5 catalyst was prepared by an excessive impregnation method and its structure and acidity were characterized by H2-TPR, NH3-TPD, HRTEM, SEAD, Py-IR, TG-DSC, and ICP analyses. The effect of preparation conditions on the catalytic performance of Ru/HZSM-5 was studied; the suitable preparation conditions were determined as follows: a calcination temperature of 450 °C, a calcination time of 3 h, a reduction temperature of 350 °C, and a reduction time of 4 h. The catalytic performance of Ru/HZSM-5 for the 2-pentanone HDO reaction was evaluated; pentane selectivity of 77.7% at a 2-pentanone conversion of 91.8% was achieved under the conditions of a reaction pressure of 5 MPa, a reaction temperature of 190 °C, a catalyst amount of 6 wt% and a reaction time of 6 h. 2-Pentanone HDO follows the reaction path of 2-pentanone hydrogenation to 2-pentanol and then 2-pentanol dehydration and hydrogenation to the target product pentane. The acidity of the catalyst plays a certain role in influencing its catalytic performance: Lewis acid sites show high activity for activating C-O bonds and Br?nsted acid sites are the key to accelerate the further dehydration of 2-pentanol and hydrogenation to alkanes.

MECHANISMS OF THE FORMATION OF ISOMERS OF ISOAMILENES IN SELECTIVE HYDROGENATION OF ISOPRENE ON A PALLADIUM-LEAD CATALYST

Beisembaeva, Z. T.,Gudkov, B. S.,Kiperman, S. L.

, p. 481 - 485 (1984)

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Dessing et al.

, p. 880 (1972)

Palladium metal nanoparticles stabilized by ionophilic ligands in ionic liquids: Synthesis and application in hydrogenation reactions

Leal, Brbara C.,Consorti, Crestina S.,Machado, Giovanna,Dupont, Jairton

, p. 903 - 909 (2015)

The reduction of [Pd(acac)(COD)]BF4 (acac = acetylacetonate; COD = 1,5-cyclooctadiene), dissolved in BMI·BF4, in the presence of P- or N-containing ionophilic ligands by H2 yields "soluble" and stable [Pd(0)]n nanoparticles (NPs). These ionic liquid soluble NPs are active and selective catalysts for the hydrogenation of 1,3-dienes and alkynes under mild reaction conditions. Selectivities up to 87% to cis-2-pentene and 95% conversion were obtained using Pd NPs modified with 1-(3-(diphenylphosphino)propyl)-2,3-dimethyl-1H-imidazol-3-ium N-bis(trifluoromethylsulfonyl)imide in 1-n-butyl-3-methylimidazolium tetrafluoroborate.

Hydrogen storage using heterocyclic compounds: The hydrogenation of 2-methylthiophene

Zhao,Oyama,Naeemi

, p. 172 - 184 (2010)

Alkyl substituted thiophenes are promising candidates for hydrogen carriers, as their dehydrogenation reactions are known to occur under mild conditions. Four types of catalysts, including supported noble metals, bimetallic noble metals, transition metal

Radical reactions in the radiolysis of cyclopentane

Wojnarovits,LaVerne

, p. 3168 - 3172 (1995)

The end products produced in the γ-radiolysis of cyclopentane have been measured at very low total doses (25-50 krad). Iodine scavenging techniques in solutions of 0.1-30 mM were used to elucidate radical yields and reaction mechanisms. The yields of the main radical species were found to be as follows: cyclopentyl, 4.9; 1-pentyl, 0.2; 3-cyclopentenyl, 0.07; H atom, 1.3 radical/100 eV. The change in yields from neat cyclopentane to 0.1 mM iodine solution suggests that about 79% of the cyclopentyl radicals escape the spur and react in the bulk medium with a disproportionation to combination ratio of 0.97. Radical precursors account for about 50% of the total end product yield, which is much smaller than found in the radiolysis of cyclohexane or cyclooctane. The radiolysis mechanism for cyclopentane is discussed and compared to those for cyclohexane and cyclooctane.

-

Vogel

, (1948)

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Mechanisms of Methylenecyclobutane Hydrogenation over Supported Metal Catalysts Studied by Parahydrogen-Induced Polarization Technique

Salnikov, Oleg G.,Burueva, Dudari B.,Kovtunova, Larisa M.,Bukhtiyarov, Valerii I.,Kovtunov, Kirill V.,Koptyug, Igor V.

, (2022/03/15)

In this work the mechanism of methylenecyclobutane hydrogenation over titania-supported Rh, Pt and Pd catalysts was investigated using parahydrogen-induced polarization (PHIP) technique. It was found that methylenecyclobutane hydrogenation leads to formation of a mixture of reaction products including cyclic (1-methylcyclobutene, methylcyclobutane), linear (1-pentene, cis-2-pentene, trans-2-pentene, pentane) and branched (isoprene, 2-methyl-1-butene, 2-methyl-2-butene, isopentane) compounds. Generally, at lower temperatures (150–350 °C) the major reaction product was methylcyclobutane while higher temperature of 450 °C favors the formation of branched products isoprene, 2-methyl-1-butene and 2-methyl-2-butene. PHIP effects were detected for all reaction products except methylenecyclobutane isomers 1-methylcyclobutene and isoprene implying that the corresponding compounds can incorporate two atoms from the same parahydrogen molecule in a pairwise manner in the course of the reaction in particular positions. The mechanisms were proposed for the formation of these products based on PHIP results.

Mechanism change of (+)-nonlinear effect in a phase separation system in a CuII-catalyzed asymmetric friedel-crafts reaction using a C2-chiral dioxolane-containing-bisamidine ligand, Naph-diPIM-dioxo-iPr

Kitamura, Masato,Le, Thien Phuc,Tanaka, Shinji,Yoshimura, Masahiro

supporting information, p. 1319 - 1333 (2020/11/30)

A CuII complex of bisamidine ligand LS, chirally modified naphtho[1,2-b:7,8-b′]dipyrroloimidazole (Naph-diPIM), catalyzes the enantioselective Friedel-Crafts (FC) reaction of indole (1a) with ethyl trifluoropyruvate (2) to give quantitatively the FC adduct 3a with a 98:2 S/R enantiomer ratio (er). The reaction shows no nonlinear effect (NLE) under the standard conditions of [1a] = [2] = 100mM; [Cu(OTf)2] = [LS + LR] = 0.10 mM; CPME; and 0 °C irrespective of the catalyst aging temperature. A five-fold increase in the catalyst concentration (0.50mM) changes the situation, leading to a strong (+)-NLE with phase separation of a white solid. The NLE is expressed by the Noyori-type mechanism: Aggregate of heterochiral dimer CuLSCuLR is separated from the reaction system (Khetero > 1 > Khomo). Furthermore, a strong (+)-NLE is observed via a purple solid liberation even with [CuII] = 0.10mM after the catalyst aging at 100 °C in the presence of an excess amount of chiral ligand. A mechanistic study has revealed i) that the sterically disfavored homochiral 1:2 complex CuLSLS is more stabilized by an intramolecular n-π? interaction than the sterically favored heterochiral 1:2 complex CuLSLR and ii) that the (+)-NLE originates from the phase separation of heterochirally interacted (CuLSLSCuLRLR).

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