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110-54-3

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110-54-3 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 110-54-3 differently. You can refer to the following data:
1. n-Hexane is a highly flammable liquid, usually isolated from crude oil, and has extensive industrial applications as a solvent in adhesive bandage factories and other industries. It is highly toxic, triggering several adverse health effects, i.e., nausea, skin irritation, dizziness, numbness of limbs, CNS depression, vertigo, and respiratory tract irritation to animals and humans. Occupational exposure of industrial workers has demonstrated motor polyneuropathy. Workers associated with long-term glue sniffi ng showed adverse effects in the form of degeneration of axons and nerve terminals.
2. n-Hexane is a highly flammable, colorless, volatile liquid with a gasoline-like odor. The water/odor threshold is 0.0064 mg/L and the air/odor threshold is 230 875 milligram per cubic meter.

Physical properties

Clear, colorless, very flammable liquid with a faint, gasoline-like odor. An odor threshold concentration of 1.5 ppmv was reported by Nagata and Takeuchi (1990).

Uses

Different sources of media describe the Uses of 110-54-3 differently. You can refer to the following data:
1. Determining refractive index of minerals; filling for thermometers instead of mercury, usually with a blue or red dye; extraction solvent for oilseed processing.
2. Suitable for HPLC, spectrophotometry, environmental testing
3. n-Hexane is a chief constituent of petroleumether, gasoline, and rubber solvent. It is usedas a solvent for adhesives, vegetable oils,and in organic analysis, and for denaturingalcohol.

Definition

ChEBI: An unbranched alkane containing six carbon atoms.

General Description

Clear colorless liquids with a petroleum-like odor. Flash points -9°F. Less dense than water and insoluble in water. Vapors heavier than air. Used as a solvent, paint thinner, and chemical reaction medium.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

HEXANE may be sensitive to light. Hexane may also be sensitive to prolonged exposure to heat. Hexane can react vigorously with oxidizing materials. This would include compounds such as liquid chlorine, concentrated O2, sodium hypochlorite and calcium hypochlorite. Hexane is also incompatible with dinitrogen tetraoxide. Hexane will attack some forms of plastics, rubber and coatings. .

Hazard

Flammable, dangerous fire risk.

Health Hazard

n-Hexane is a respiratory tract irritant andat high concentrations a narcotic. Its acutetoxicity is greater than that of n-pentane.Exposure to a concentration of 40,000 ppmfor an hour caused convulsions and death inmice. In humans a 10-minute exposure toabout 5000 ppm may produce hallucination,distorted vision, headache, dizziness, nausea,and irritation of eyes and throat. Chronicexposure to n-hexane may cause polyneuritis.The metabolites of n-hexane injected inguinea pigs were reported as 2,5- hexanedioneand 5-hydroxy-2-hexanone, which arealso metabolites of methyl butyl ketone(DiVincenzo et al. 1976). Thus methyl butylketone and n- hexane should have similartoxicities. The neurotoxic metabolite, 2,5-hexanedione, however, is produced considerablyless in n-hexane. However, in the caseof hexane, the neurotoxic metabolite 2,5-hexanedione is produced to a much lesserextent. Continuous exposure to 250 ppmn-hexane produced neurotoxic effects in animals. Occupational exposure to 500 ppmmay cause polyneuropathy (ACGIH 1986).Inhalation of n-hexane vapors have shownreproductive effects in rats and mice.

Flammability and Explosibility

Hexane is extremely flammable (NFPA rating = 3), and its vapor can travel a considerable distance to an ignition source and "flash back." Hexane vapor forms explosive mixtures with air at concentrations of 1.1 to 7.5 % (by volume). Hydrocarbons of significantly higher molecular weight have correspondingly higher vapor pressures and therefore present a reduced flammability hazard. Carbon dioxide or dry chemical extinguishers should be used for hexane fires.

Chemical Reactivity

Reactivity with Water: No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Potential Exposure

n-Hexane is industrial chemical, emul sifier, in manufacture of plastics, resins; as a solvent, par ticularly in the extraction of edible fats and oils; as a laboratory reagent; and as the liquid in low temperature thermometers. Technical and commercial grades consist of 45 85% hexane, as well as cyclopentanes, isohexane, and 1% to 6% benzene.

Carcinogenicity

Male rabbits exposed to 3000 ppm hexane (8 h/day, 6 days/week for 24 weeks) developed papillary proliferation of nonciliated bronchiolar cells. No tumors were found in mice painted with hexane and croton oil as cocarcinogen, presumably for the lifetime of each animal. Hexane is inactive as a tumorpromoting agent.

Source

In diesel engine exhaust at a concentration of 1.2% of emitted hydrocarbons (quoted, Verschueren, 1983). A constituent in gasoline. Harley et al. (2000) analyzed the headspace vapors of three grades of unleaded gasoline where ethanol was added to replace methyl tert-butyl ether. The gasoline vapor concentrations of hexane in the headspace were 4.31 wt % for regular grade, 3.74.8 wt % for midgrade, and 2.3 wt % for premium grade. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 1.82 and 268 mg/km, respectively (Schauer et al., 2002).

Environmental fate

Biological. Hexane may biodegrade in two ways. The first is the formation of hexyl hydroperoxide, which decomposes to 1-hexanol followed by oxidation to hexanoic acid. The other pathway involves dehydrogenation to 1-hexene, which may react with water giving 1-hexanol (Dugan, 1972). Microorganisms can oxidize alkanes under aerobic conditions (Singer and Finnerty, 1984). The most common degradative pathway involves the oxidation of the terminal methyl group forming 1-hexanol. The alcohol may undergo a series of dehydrogenation steps forming a hexanal followed by oxidation to form hexanoic acid. The fatty acid may then be metabolized by β-oxidation to form the mineralization products, carbon dioxide and water (Singer and Finnerty, 1984). Photolytic. An aqueous solution irradiated by UV light at 50 °C for 1 d resulted in a 50.51% yield of carbon dioxide (Knoevenagel and Himmelreich, 1976). Synthetic air containing gaseous nitrous acid and exposed to artificial sunlight (λ = 300–450 nm) photooxidized hexane into two isomers of hexyl nitrate and peroxyacetal nitrate (Cox et al., 1980). Chemical/Physical. Complete combustion in air yields carbon dioxide and water vapor.

storage

hexane should be used only in areas free of ignition sources, and quantities greater than 1 liter should be stored in tightly sealed metal containers in areas separate from oxidizers.

Shipping

UN1208 Hexanes, Hazard Class: 3; Labels: 3-Flammable liquid.

Purification Methods

Purify as for n-heptane. Modifications include the use of chlorosulfonic acid or 35% fuming H2SO4 instead of conc H2SO4 in washing the alkane, and final drying and distilling from sodium hydride. Unsaturated impurities can be removed by shaking the hexane with nitrating acid (58% H2SO4, 25% conc HNO3, 17% water, or 50% HNO3, 50% H2SO4), then washing the hydrocarbon layer with conc H2SO4, followed by H2O, drying, and distilling over sodium or n-butyl lithium. It can also be purified by distillation under nitrogen from sodium benzophenone ketyl solubilised with tetraglyme. Also purify it by passage through a silica gel column followed by distillation [Kajii et al. J Phys Chem 91 2791 1987]. It is a FLAMMABLE liquid and a possible nerve toxin. [Beilstein 1 IV 338.] Rapid purification: Distil, discarding the first forerun and stored over 4A molecular sieves.

Toxicity evaluation

Identification of 2,5-hexanedione as the major neurotoxic metabolite of n-hexane proceeded rapidly after its discovery as a urinary metabolite. 2,5-Hexanedione has been found to produce a polyneuropathy indistinguishable from n-hexane. 2,5-Hexanedione is many times more potent than n-hexane, the parent compound, in causing neurotoxicity in experimental animals. It appears that the neurotoxicity of 2,5-hexanedione resides in its γ-diketone structure since 2,3-, 2,4-hexanedione and 2,6-heptanedione are not neurotoxic, while 2,5-heptanedione and 3,6-octanedione and other g-diketones are neurotoxic.

Incompatibilities

May form explosive mixture with air. Contact with strong oxidizers may cause fire and explo sions. Contact with dinitrogen tetraoxide may explode @ 28℃.Attacks some plastics, rubber and coatings. May accumulate static electrical charges, and may cause ignition of its vapors.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinera tor equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

Check Digit Verification of cas no

The CAS Registry Mumber 110-54-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 110-54:
(5*1)+(4*1)+(3*0)+(2*5)+(1*4)=23
23 % 10 = 3
So 110-54-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H14/c1-3-5-6-4-2/h3-6H2,1-2H3

110-54-3 Well-known Company Product Price

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  • Alfa Aesar

  • (43263)  n-Hexane, anhydrous   

  • 110-54-3

  • 250ml

  • 354.0CNY

  • Detail
  • Alfa Aesar

  • (43263)  n-Hexane, anhydrous   

  • 110-54-3

  • 1L

  • 773.0CNY

  • Detail
  • Alfa Aesar

  • (43263)  n-Hexane, anhydrous   

  • 110-54-3

  • 4L

  • 1804.0CNY

  • Detail
  • Alfa Aesar

  • (47104)  n-Hexane, anhydrous, over molecular sieves, packaged under argon in resealable ChemSeal? bottles   

  • 110-54-3

  • 250ml

  • 483.0CNY

  • Detail
  • Alfa Aesar

  • (47104)  n-Hexane, anhydrous, over molecular sieves, packaged under argon in resealable ChemSeal? bottles   

  • 110-54-3

  • 1L

  • 937.0CNY

  • Detail
  • Alfa Aesar

  • (42100)  n-Hexane, Environmental Grade, 95+%   

  • 110-54-3

  • 1L

  • 354.0CNY

  • Detail
  • Alfa Aesar

  • (42100)  n-Hexane, Environmental Grade, 95+%   

  • 110-54-3

  • 4L

  • 1162.0CNY

  • Detail
  • Alfa Aesar

  • (42100)  n-Hexane, Environmental Grade, 95+%   

  • 110-54-3

  • *4x1L

  • 1264.0CNY

  • Detail
  • Alfa Aesar

  • (42100)  n-Hexane, Environmental Grade, 95+%   

  • 110-54-3

  • *4x4L

  • 4646.0CNY

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  • Alfa Aesar

  • (39199)  n-Hexane, HPLC Grade, 95% min   

  • 110-54-3

  • 1L

  • 419.0CNY

  • Detail
  • Alfa Aesar

  • (39199)  n-Hexane, HPLC Grade, 95% min   

  • 110-54-3

  • 2500ml

  • 864.0CNY

  • Detail
  • Alfa Aesar

  • (39199)  n-Hexane, HPLC Grade, 95% min   

  • 110-54-3

  • 4L

  • 1172.0CNY

  • Detail

110-54-3SDS

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 Hexane

1.2 Other means of identification

Product number -
Other names n-Hexane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Hydrocarbons (contain hydrogen and carbon atoms), Volatile organic compounds
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:110-54-3 SDS

110-54-3Synthetic route

1-hexene
592-41-6

1-hexene

hexane
110-54-3

hexane

Conditions
ConditionsYield
With hydrogen; In tetrahydrofuran at 90℃; under 5250.4 Torr; for 0.166667h; Product distribution; other olefins, other catalysts; var. temp., solv., press., and time;100%
With hydrogen; (iPrPDI)Fe(N2)2 at 20℃; under 3040 Torr; for 19h;100%
With Wilkinson's catalyst; hydrogen In dichloromethane-d2 at 45℃; under 3000.3 Torr; for 6h; Concentration; Reagent/catalyst; Solvent; Temperature; Time; Sealed tube; Inert atmosphere;100%
1-hexene
592-41-6

1-hexene

hydrogen
1333-74-0

hydrogen

hexane
110-54-3

hexane

Conditions
ConditionsYield
With C61H98ClN3P2Ru In dichloromethane-d2 at 50℃; under 3040.2 Torr; for 4h; Reagent/catalyst; Time;100%
With triethylsilane; ReH(NO)2(P(CH(CH3)2)3)2; tris(pentafluorophenyl)borate at 100℃; under 30003 Torr; for 1h; Catalytic behavior; Autoclave;
With triethylsilane; [ReH(NO)2(P(C6H11)3)2]; tris(pentafluorophenyl)borate at 100℃; under 30003 Torr; for 1h; Catalytic behavior; Autoclave;
C26H30CoN4(1+)*ClO4(1-)

C26H30CoN4(1+)*ClO4(1-)

hexane
110-54-3

hexane

Conditions
ConditionsYield
With sulfuric acid; oxygen at 60℃; under 3750.38 Torr; for 12h; Catalytic behavior; Reagent/catalyst;100%
1-hexene
592-41-6

1-hexene

A

trans-2-hexene
4050-45-7

trans-2-hexene

B

hexane
110-54-3

hexane

Conditions
ConditionsYield
With Rh complex with phosphoryl-terminated carbosilane dendrimer; hydrogen In acetone at 25℃; under 7500.75 Torr; for 2h; Product distribution; Further Variations:; Reagents;A 0.5%
B 99.5%
With hydrogen; poly-1,2,3-triazolyl ferrocenyl dendrimer-Pd nanoparticle In methanol; chloroform at 25℃; under 760.051 Torr;A 57%
B 43%
With hydrogen; Pd(salen) encapsuled in zeolite X at 25℃; under 400 Torr; for 24h; Product distribution; var. catalysts; cyclohexene;
hex-3-yne
928-49-4

hex-3-yne

A

cis-3-hexene
7642-09-3

cis-3-hexene

B

hexane
110-54-3

hexane

Conditions
ConditionsYield
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760 Torr; Kinetics;A 99.5%
B n/a
With bis(pentamethylcyclopentadienyl)titanium(III) hydride; hydrogen In (2)H8-toluene for 0.25h; Sealed tube;A 80%
B 20%
With silica-supported frustrated Lewis pair 3a (HBC6F5)2; (4-hydroxyphenyl)biphenylphosphine; [(SiO)2AliBuEt2O)]) In pentane at 80℃; under 30003 Torr; for 4h; Reagent/catalyst; stereoselective reaction;
1-hexene
592-41-6

1-hexene

cyclohexa-1,4-diene
1165952-92-0

cyclohexa-1,4-diene

A

hexane
110-54-3

hexane

B

cyclohexene
110-83-8

cyclohexene

Conditions
ConditionsYield
With C24H72Ba2N4Si8 In (2)H8-toluene at 120℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube;A 99%
B n/a
oenanthic acid
111-14-8

oenanthic acid

hexane
110-54-3

hexane

Conditions
ConditionsYield
With hydrogen; silica gel; palladium at 330℃; Ni/Al2O3, 180 deg C;98%
With 10-phenyl-9-(2,4,6-trimethylphenyl)acridinium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; diphenyldisulfane In 2,2,2-trifluoroethanol; ethyl acetate at 20℃; for 48h; Irradiation;40%
With barytes
Multi-step reaction with 3 steps
1: borane-d3-tetrahydrofuran / tetrahydrofuran
2: pyridinium dichlorochromate / dichloromethane
3: aldehyde deformylating oxygenase / glycerol / 0.08 h / pH 7.5
View Scheme
2-Hexyne
764-35-2

2-Hexyne

A

3-hexene
592-47-2

3-hexene

B

trans-2-hexene
4050-45-7

trans-2-hexene

C

hexane
110-54-3

hexane

Conditions
ConditionsYield
With hydrogen; palladium In ethanol at 30℃; under 15200 Torr; Product distribution;A 0.8%
B 98%
C 1.2%
n-hexan-2-one
591-78-6

n-hexan-2-one

hexane
110-54-3

hexane

Conditions
ConditionsYield
With hydrogen; K-10 montmorillonite; platinum In diethylene glycol dimethyl ether under 37503 Torr; for 20h; Reduction;98%
With hydrogen; aluminum oxide; nickel at 190℃;88%
With hydrogen at 100℃; under 750.075 Torr; for 3h;
Multi-step reaction with 2 steps
1: hydrogen / cyclohexane / 120 °C / 45004.5 Torr
2: hydrogen / cyclohexane / 120 °C / 45004.5 Torr
View Scheme
2,5-hexanedione
110-13-4

2,5-hexanedione

hexane
110-54-3

hexane

Conditions
ConditionsYield
With hydrogen; K-10 montmorillonite; platinum In diethylene glycol dimethyl ether under 37503 Torr; for 20h; Reduction;98%
Stage #1: 2,5-hexanedione With hydrogen at 120℃; under 20702.1 Torr; for 0.5h;
Stage #2: at 200℃; under 20702.1 Torr; for 5h; Reagent/catalyst;
Multi-step reaction with 2 steps
1: palladium/alumina; hydrogen / 0.5 h / 200 °C / 20702.1 Torr
2: palladium/alumina; hydrogen / 4 h / 200 °C / 20702.1 Torr
View Scheme
1-Iodohexane
638-45-9

1-Iodohexane

η3-allylbis(cyclopentadienyl)titanium(III)

η3-allylbis(cyclopentadienyl)titanium(III)

hexane
110-54-3

hexane

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; Product distribution;97%
2-Hexyne
764-35-2

2-Hexyne

A

cis-2-hexene
7688-21-3

cis-2-hexene

B

hexane
110-54-3

hexane

Conditions
ConditionsYield
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760 Torr; Kinetics;A 97%
B n/a
potassium carbonate
584-08-7

potassium carbonate

1-Bromo-2-butyne
3355-28-0

1-Bromo-2-butyne

hexane
110-54-3

hexane

Conditions
ConditionsYield
In ethyl acetate; N,N-dimethyl-formamide96.2%
1-bromo-hexane
111-25-1

1-bromo-hexane

hexane
110-54-3

hexane

Conditions
ConditionsYield
With ammonium chloride; zinc In tetrahydrofuran; water at 20℃; for 3h;95%
With lithium aluminium tetrahydride; 15-crown-5 In benzene at 80℃; for 6h;83%
Stage #1: 1-bromo-hexane With magnesium In diethyl ether
Stage #2: With ammonium chloride In water Further stages.;
37%
With tris-(trimethylsilyl)silane; oxygen at 60℃; for 6h; in sealed vial;81 % Chromat.
Conditions
ConditionsYield
With Bu3Sn4; 2,4,5,7-tetraiodo-6-hydroxy-3-fluorone Mechanism; Product distribution; Irradiation; also other halides;95%
With borohydride exchange resin; nickel diacetate In methanol for 3h; Ambient temperature;98 % Chromat.
1-hexene
592-41-6

1-hexene

benzyl alcohol
100-51-6

benzyl alcohol

A

hexane
110-54-3

hexane

B

Heptanophenone
1671-75-6

Heptanophenone

Conditions
ConditionsYield
With 5-hexyl-2,4,6-triaminopyrimidine; 5-[4-(Ph2P)benzyl]-5-ethyl-2,4,6-(1H,3H,5H)-pyrimidinetrione; substituted barbituric acid aminopyridine-containing reagent; [Rh(coe)2Cl]2; cyclohexylamine In 1,4-dioxane; phenol at 150℃; for 2h;A n/a
B 95%
5-Hydroxymethyl-5'-formyl-2,2'-bithiophene
170110-95-9

5-Hydroxymethyl-5'-formyl-2,2'-bithiophene

A

5-acetoxymethyl-5'-formyl-2,2'-bithiophene

5-acetoxymethyl-5'-formyl-2,2'-bithiophene

B

hexane
110-54-3

hexane

Conditions
ConditionsYield
With pyridine; acetic anhydride In water; ethyl acetateA n/a
B 95%
With pyridine; acetic anhydride In water; ethyl acetateA n/a
B 95%
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;
n-hexan-2-ol
626-93-7

n-hexan-2-ol

hexane
110-54-3

hexane

Conditions
ConditionsYield
With hydrogen; aluminum oxide; nickel at 180℃;91%
With hydrogen In n-heptane at 119.84℃; under 51005.1 Torr; for 1h; Kinetics; Autoclave; Inert atmosphere;
With hydrogen In cyclohexane at 120℃; under 45004.5 Torr; Catalytic behavior; Reagent/catalyst;
hex-1-yne
693-02-7

hex-1-yne

A

1-hexene
592-41-6

1-hexene

B

hexane
110-54-3

hexane

Conditions
ConditionsYield
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760 Torr; Kinetics;A 91%
B n/a
With hydrogen; platinum In ethanol at 30℃; under 15200 Torr; Product distribution; 80 atm;A 41.7%
B 57.3%
With hydrogen; Ni(C17H35COO)2; triethylaluminum In toluene at 40℃; Kinetics; Object of study: selectivity;
3-chloropropyl dichloromethylsilane

3-chloropropyl dichloromethylsilane

vinylmagnesium chloride
3536-96-7

vinylmagnesium chloride

hexane
110-54-3

hexane

Conditions
ConditionsYield
In tetrahydrofuran91%
hex-1-yne
693-02-7

hex-1-yne

A

cis-2-hexene
7688-21-3

cis-2-hexene

B

trans-2-hexene
4050-45-7

trans-2-hexene

C

hexane
110-54-3

hexane

Conditions
ConditionsYield
With hydrogen; palladium In ethanol at 30℃; under 15200 Torr; Product distribution;A 3.8%
B 90.2%
C 6%
p-aminomethylbenzoic acid
56-91-7

p-aminomethylbenzoic acid

2,2-diphenyl ethanol
1883-32-5

2,2-diphenyl ethanol

A

4-[2,2-(diphenyl)ethoxycarbamoyl-methyl]benzoic acid

4-[2,2-(diphenyl)ethoxycarbamoyl-methyl]benzoic acid

B

hexane
110-54-3

hexane

Conditions
ConditionsYield
With CDI In tetrahydrofuran; sodium hydroxideA 90%
B n/a
pyrrolidine
123-75-1

pyrrolidine

3,3-dimethyl-D-cysteine
52-67-5

3,3-dimethyl-D-cysteine

A

4-carboxy-2,5,5-trimethylthiazolidine-2-acetopyrrolidide

4-carboxy-2,5,5-trimethylthiazolidine-2-acetopyrrolidide

B

hexane
110-54-3

hexane

Conditions
ConditionsYield
In benzeneA 90%
B n/a
1-hexene
592-41-6

1-hexene

A

hexane
110-54-3

hexane

B

2-hexene
592-43-8

2-hexene

Conditions
ConditionsYield
With RuHCl(PPh3)((CH3OCH2CH2)2Im)(SIMes2); hydrogen at 100℃; under 3000.3 Torr; for 4h; Concentration; Reagent/catalyst; Solvent; Temperature; Time; Sealed tube; Inert atmosphere;A 13%
B 87%
With hydrogen; Polymer-bound Ni2-catalyst at 100℃; under 51714.8 Torr; for 3h; Product distribution; Other catalyst;A 77%
B 11%
With hydrogen In ethanol; toluene at 40℃; under 2625.26 Torr; for 2h; Catalytic behavior; Inert atmosphere;A 72%
B 28%
1-hexene
592-41-6

1-hexene

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

A

hexane
110-54-3

hexane

B

1-(4-methoxyphenyl)-1-heptanone
69287-13-4

1-(4-methoxyphenyl)-1-heptanone

Conditions
ConditionsYield
With 5-hexyl-2,4,6-triaminopyrimidine; substituted barbituric acid aminopyridine-containing reagent; triphenylphosphine; [Rh(coe)2Cl]2; cyclohexylamine In 1,4-dioxane at 150℃;A n/a
B 87%
1-hexene
592-41-6

1-hexene

4-(trifluoromethyl)benzylic alcohol
349-95-1

4-(trifluoromethyl)benzylic alcohol

A

hexane
110-54-3

hexane

B

1-[4-(trifluoromethyl)phenyl]heptan-1-one

1-[4-(trifluoromethyl)phenyl]heptan-1-one

Conditions
ConditionsYield
With 5-hexyl-2,4,6-triaminopyrimidine; substituted barbituric acid aminopyridine-containing reagent; triphenylphosphine; [Rh(coe)2Cl]2; cyclohexylamine In 1,4-dioxane at 150℃;A n/a
B 86%
aqua{o,o'-bis((dimethylamino)methyl)phenyl}nickel(II) tetrafluoroborate

aqua{o,o'-bis((dimethylamino)methyl)phenyl}nickel(II) tetrafluoroborate

hexane
110-54-3

hexane

Ni(((CH3)2NCH2)2C6H3)(H2O)(1+)*BF4(1-)*0.167C6H14 = [Ni(C6H3(CH2N(CH3)2)2)(H2O)][BF4]*0.167C6H14

Ni(((CH3)2NCH2)2C6H3)(H2O)(1+)*BF4(1-)*0.167C6H14 = [Ni(C6H3(CH2N(CH3)2)2)(H2O)][BF4]*0.167C6H14

Conditions
ConditionsYield
In hexane; dichloromethane (N2); n-hexane added dropwise to CH2Cl2 soln. of Ni compd.; (N2); cryst. material obtained; elem. anal.;100%
hexane
110-54-3

hexane

[methyl(hydridotris(3,5-dimethylpyrazolyl)borate)(trimethylphosphine)iridium(III)(N2)][B(3,5-C6H3(CF3)2)4]*(dichloromethane)

[methyl(hydridotris(3,5-dimethylpyrazolyl)borate)(trimethylphosphine)iridium(III)(N2)][B(3,5-C6H3(CF3)2)4]*(dichloromethane)

triphenyl-arsane
603-32-7

triphenyl-arsane

[methyl(hydridotris(3,5-dimethylpyrazolyl)borate)(trimethylphosphine)iridium(III)(AsPh3)][B(3,5-C6H3(CF3)2)4]*(hexane)

[methyl(hydridotris(3,5-dimethylpyrazolyl)borate)(trimethylphosphine)iridium(III)(AsPh3)][B(3,5-C6H3(CF3)2)4]*(hexane)

Conditions
ConditionsYield
In dichloromethane byproducts: N2; CH2Cl2 soln. of AsPh3 (1 equiv.) added to CH2Cl2 soln. of Ir complex at -40°C; stirred for 12 h; filtered through glass fiber filter paper; solvent removed under reducedpressure; hexane diffused into concd. ether soln. at 22°C; elem. anal.;100%
hexane
110-54-3

hexane

(BrC6H4C3HO2H)2C2H2O2C(CH3)2

(BrC6H4C3HO2H)2C2H2O2C(CH3)2

iron(III) chloride
7705-08-0

iron(III) chloride

[(BrC6H4C3HO2)2C2H2O2C(CH3)2]3Fe2*C6H14

[(BrC6H4C3HO2)2C2H2O2C(CH3)2]3Fe2*C6H14

Conditions
ConditionsYield
In methanol in methanol; crystd.(hexane), elem. anal.;100%
hexane
110-54-3

hexane

[(cod)Ir(3-(diphenylphosphino)methyl-5-pyridylpyrazolato)Ir(cod)]BF4
881493-73-8

[(cod)Ir(3-(diphenylphosphino)methyl-5-pyridylpyrazolato)Ir(cod)]BF4

carbon monoxide
201230-82-2

carbon monoxide

[(CO)2Ir(3-(diphenylphosphino)methyl-5-pyridylpyrazolato)Ir(CO)2]BF4*0.4hexane

[(CO)2Ir(3-(diphenylphosphino)methyl-5-pyridylpyrazolato)Ir(CO)2]BF4*0.4hexane

Conditions
ConditionsYield
In dichloromethane soln. Ir-Ir complex in CH2Cl2 was stirred under CO atm. (1 atm.) for 3 hat room temp.; hexane was added, ppt. was washed with ether and dried in vacuo; elem. anal.;100%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

hexane
110-54-3

hexane

[C6H4-1,2-{NC(t-Bu)N(2,6-Me2C6H3)}2]Yb(THF)
1541157-10-1

[C6H4-1,2-{NC(t-Bu)N(2,6-Me2C6H3)}2]Yb(THF)

triphenyltin chloride
639-58-7

triphenyltin chloride

0.5C4H8O*0.25C6H14*C36H50ClN4O2Yb

0.5C4H8O*0.25C6H14*C36H50ClN4O2Yb

B

hexaphenylditin
1064-10-4

hexaphenylditin

Conditions
ConditionsYield
Stage #1: [C6H4-1,2-{NC(t-Bu)N(2,6-Me2C6H3)}2]Yb(THF); triphenyltin chloride In tetrahydrofuran for 12h; Schlenk technique;
Stage #2: 1,2-dimethoxyethane; hexane Schlenk technique;
A 75%
B 100%
hexane
110-54-3

hexane

C20H21FeN2Na*0.4C4H8O

C20H21FeN2Na*0.4C4H8O

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

C76H72Fe2N4Na2O2P2*0.5C6H14

C76H72Fe2N4Na2O2P2*0.5C6H14

Conditions
ConditionsYield
Stage #1: C20H21FeN2Na*0.4C4H8O; Triphenylphosphine oxide In toluene at 20℃; Inert atmosphere; Schlenk technique;
Stage #2: hexane In toluene at -30 - 20℃; for 24h; Inert atmosphere; Schlenk technique;
100%
hexane
110-54-3

hexane

N2SO4

N2SO4

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

2-chloro-ethanol
107-07-3

2-chloro-ethanol

1-(4-(2-hydroxyethoxy)phenyl)ethanone
31769-45-6

1-(4-(2-hydroxyethoxy)phenyl)ethanone

Conditions
ConditionsYield
With potassium carbonate In water; ethyl acetate; N,N-dimethyl-formamide99.4%
hexane
110-54-3

hexane

([PhP(CH2SiMe2NPh)2]Ta)2(μ–η1:η2-N2)(μ-H)2

([PhP(CH2SiMe2NPh)2]Ta)2(μ–η1:η2-N2)(μ-H)2

phenylsilane
694-53-1

phenylsilane

([PhNSiMe2CH2)2PPh]TaH)(μ-H)2(μ-η1:η2-NNSiH2Ph)(Ta[PhNSiMe2CH2)2PPh])*0.5(hexane)

([PhNSiMe2CH2)2PPh]TaH)(μ-H)2(μ-η1:η2-NNSiH2Ph)(Ta[PhNSiMe2CH2)2PPh])*0.5(hexane)

Conditions
ConditionsYield
In toluene under N2; to a stirred soln. of Ta-contg. compd. (0.350 mmol) in toluenewas added phenylsilane (0.350 mmol) in the same solvent; stirring for 2 4 h at -40°C; solvent was removed under vac.; the residue was triturated under hexanesand left overnight; the ppt. was recovered on a glass frit; elem. anal.;99%
di(rhodium)tetracarbonyl dichloride

di(rhodium)tetracarbonyl dichloride

hexane
110-54-3

hexane

C4H2N(C(C6F5)(C4HNHO)C(C6F5)(C4H2NH))2C(C6F5)

C4H2N(C(C6F5)(C4HNHO)C(C6F5)(C4H2NH))2C(C6F5)

(Rh(CO)2)C4H2N(C(C6F5)(C4HNO)C(C6F5)(C4H2NH))(C(C6F5)(C4HNHO)C(C6F5)(C4H2NH))C(C6F5)*1.5C6H14

(Rh(CO)2)C4H2N(C(C6F5)(C4HNO)C(C6F5)(C4H2NH))(C(C6F5)(C4HNHO)C(C6F5)(C4H2NH))C(C6F5)*1.5C6H14

Conditions
ConditionsYield
With CH3COONa In dichloromethane Rh complex and anhydrous sodium acetate added to soln. of dioxopentaphyrin in CH2Cl2, stirred under reflux for 3 h; chromy, (silica gel, CH2Cl2/hexane (4/6)), removal of solvent;99%
chloromethyl(1,5-cyclooctadiene)palladium(II)

chloromethyl(1,5-cyclooctadiene)palladium(II)

hexane
110-54-3

hexane

sodium 2,6-di((2,6-diisopropylphenyl)iminomethyl)-4-methylphenolate

sodium 2,6-di((2,6-diisopropylphenyl)iminomethyl)-4-methylphenolate

[Pd2(/mu.-Cl)Me2(2,6-di((2,6-diisopropylphenyl)iminomethyl)-4-methylphenolate)]*hexane
1156486-95-1

[Pd2(/mu.-Cl)Me2(2,6-di((2,6-diisopropylphenyl)iminomethyl)-4-methylphenolate)]*hexane

Conditions
ConditionsYield
In toluene byproducts: NaCl; (Ar, Schlenk technique); addn. of toluene soln. of 2 equiv. of palladiumcompd. to toluene soln. of phenol deriv., stirring at room temp. for 12 h; evapn., washing with hexane, elem. anal.;99%
hexane
110-54-3

hexane

dichloromethane
75-09-2

dichloromethane

[(pentamethylcyclopentadienyl)2ZrMe(2-(di-tert-butylphosphino)phenoxide)]
1309604-37-2

[(pentamethylcyclopentadienyl)2ZrMe(2-(di-tert-butylphosphino)phenoxide)]

2,6-di-tert-butylpyridininum tetrakis(pentafluorophenyl)borate
1309604-77-0

2,6-di-tert-butylpyridininum tetrakis(pentafluorophenyl)borate

(C5(CH3)5)2ZrClOC6H4P(C(CH3)3)2CH2Cl(1+)*B(C6F5)4(1-)*CH2Cl2*CH3(CH2)4CH3=ZrC35H54Cl2OPB(C6F5)4*CH2Cl2*C6H14

(C5(CH3)5)2ZrClOC6H4P(C(CH3)3)2CH2Cl(1+)*B(C6F5)4(1-)*CH2Cl2*CH3(CH2)4CH3=ZrC35H54Cl2OPB(C6F5)4*CH2Cl2*C6H14

Conditions
ConditionsYield
In dichloromethane (Ar); mixing a solns. of Zr complex and pyridinium salt in CH2Cl2, standing overnight; pouring in hexane, filtration, washing with hexanes, drying in vac., layering a soln. in CH2Cl2 with hexane; elem. anal.;99%
pyridine
110-86-1

pyridine

hexane
110-54-3

hexane

2,6-bis((S)-1-cyclohexyl-4-isopropyl-4,5-dihydro-1H-imidazol-2-yl)phenylchloroplatinum(II)

2,6-bis((S)-1-cyclohexyl-4-isopropyl-4,5-dihydro-1H-imidazol-2-yl)phenylchloroplatinum(II)

silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

[(2,6-bis((S)-1-cyclohexyl-4-isopropyl-4,5-dihydro-1H-imidazol-2-yl)phenyl)Pt(pyridine)][OTf]*0.4C6H14

[(2,6-bis((S)-1-cyclohexyl-4-isopropyl-4,5-dihydro-1H-imidazol-2-yl)phenyl)Pt(pyridine)][OTf]*0.4C6H14

Conditions
ConditionsYield
In pyridine; dichloromethane byproducts: AgCl; Pt complex was reacted with Ag salt (1 equiv.) in presence of pyridine (1 equiv.) in CH2Cl2 at room temp. for 24 h; filtered through Celite; evapd.; chromd. (silica gel plates, CH2Cl2/MeOH, 10/1); elem. anal.;99%
hexane
110-54-3

hexane

C56H52N4Pd
109533-33-7

C56H52N4Pd

Nitrogen dioxide
10102-44-0

Nitrogen dioxide

2-nitro-meso-tetramesitylporphyrinatopalladium(II) hexane 1.25-solvate

2-nitro-meso-tetramesitylporphyrinatopalladium(II) hexane 1.25-solvate

Conditions
ConditionsYield
Stage #1: C56H52N4Pd; Nitrogen dioxide In dichloromethane
Stage #2: hexane In dichloromethane
99%
bis(triphenylphosphine)(carbonyl)rhodium chloride
13938-94-8, 15318-33-9, 16353-77-8

bis(triphenylphosphine)(carbonyl)rhodium chloride

hexane
110-54-3

hexane

N,N-bis((diphenylphosphino)methyl)benzenamine
129880-59-7

N,N-bis((diphenylphosphino)methyl)benzenamine

[RhCl(CO){PhN(CH2PPh2)2}2]*0.5C6H14

[RhCl(CO){PhN(CH2PPh2)2}2]*0.5C6H14

Conditions
ConditionsYield
Stage #1: bis(triphenylphosphine)(carbonyl)rhodium chloride; N,N-bis((diphenylphosphino)methyl)benzenamine In toluene at 20 - 80℃; Inert atmosphere;
Stage #2: hexane Inert atmosphere;
99%
hexane
110-54-3

hexane

cis-[PtCl2(COD)]
12080-32-9

cis-[PtCl2(COD)]

bis(2-isocyanophenyl) phenylphosphonate
1486481-56-4

bis(2-isocyanophenyl) phenylphosphonate

C20H13Cl2N2O3PPt*0.25C6H14

C20H13Cl2N2O3PPt*0.25C6H14

Conditions
ConditionsYield
In dichloromethane for 2h; Schlenk technique; Inert atmosphere;99%
chlorobis(cyclooctene)-iridium(I) dimer

chlorobis(cyclooctene)-iridium(I) dimer

hexane
110-54-3

hexane

C40H34N2P2

C40H34N2P2

C80H68Cl2Ir2N4P4*0.15C6H14

C80H68Cl2Ir2N4P4*0.15C6H14

Conditions
ConditionsYield
Stage #1: chlorobis(cyclooctene)-iridium(I) dimer; C40H34N2P2 In benzene for 72h; Glovebox; Schlenk technique;
Stage #2: hexane Glovebox; Schlenk technique;
99%
hexane
110-54-3

hexane

(2S)-2-(2-propenyl)octanoic acid
213914-70-6

(2S)-2-(2-propenyl)octanoic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium chloride In ethyl acetate98%
hexane
110-54-3

hexane

2-fluorobenzonitrile
394-47-8

2-fluorobenzonitrile

imidazolyl sodium
5587-42-8

imidazolyl sodium

2-imidazol-1-yl-benzonitrile
25373-49-3

2-imidazol-1-yl-benzonitrile

Conditions
ConditionsYield
In chloroform; acetonitrile98%
(tri(p-fluorophenyl)phosphine)3RhCl
25478-56-2

(tri(p-fluorophenyl)phosphine)3RhCl

hexane
110-54-3

hexane

[1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene
141556-42-5

[1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene

[(CN(C6H2(CH3)3)CHCHN(C6H2(CH3)3))Rh(P(C6H4F)3)2Cl]*0.5C6H14

[(CN(C6H2(CH3)3)CHCHN(C6H2(CH3)3))Rh(P(C6H4F)3)2Cl]*0.5C6H14

Conditions
ConditionsYield
In toluene byproducts: P(p-F-Ph)3; (Ar); std. Schlenk technique; ligand (1 equiv.) was added to Rh complex;toluene was added; soln. was stirred for 16 h; concd.; hexane added; cooled at -20°C for 2 h; filtered; residue washed (hexane); dried in vac. overnight;98%
hexane
110-54-3

hexane

2-mercapto-N-methylbenzamide
20054-45-9

2-mercapto-N-methylbenzamide

mercury dichloride

mercury dichloride

Hg(SC6H4CONHCH3)2*0.25C6H14

Hg(SC6H4CONHCH3)2*0.25C6H14

Conditions
ConditionsYield
In methanol (Ar); addn. of HgCl2 to a soln. of ligand in methanol at room temp., stirring for 2 h; concn., addn. of satd. aq. NaCl, filtration, washing ppt. with satd. aq.NaCl, water, recrystn. (methanol); elem. anal.;98%

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110-54-3Relevant articles and documents

-

Brown,Brown

, p. 2827 (1962)

-

Regio- and Chemoselective Hydrogenation of Dienes to Monoenes Governed by a Well-Structured Bimetallic Surface

Miyazaki, Masayoshi,Furukawa, Shinya,Komatsu, Takayuki

, p. 18231 - 18239 (2017)

Unprecedented surface chemistry, governed by specific atomic arrangements and the steric effect of ordered alloys, is reported. Rh-based ordered alloys supported on SiO2 (RhxMy/SiO2, M = Bi, Cu, Fe, Ga, In, Pb, Sn, and Zn) were prepared and tested as catalysts for selective hydrogenation of trans-1,4-hexadiene to trans-2-hexene. RhBi/SiO2 exhibited excellent regioselectivity for the terminal C=C bond and chemoselective hydrogenation to the monoene, not to the overhydrogenated alkane, resulting in a high trans-2-hexene yield. Various asymmetric dienes, including terpenoids, were converted into the corresponding inner monoenes in high yields. This is the first example of a regio- and chemoselective hydrogenation of dienes using heterogeneous catalysts. Kinetic studies and density functional theory calculations revealed the origin of the high selectivity: (1) one-dimensionally aligned Rh arrays geometrically limit hydrogen diffusion and attack to alkenyl carbons from one direction and (2) adsorption of the inner C=C moiety to Rh is inhibited by steric repulsion from the large Bi atoms. The combination of these effects preferentially hydrogenates the terminal C=C bond and prevents overhydrogenation to the alkane.

Direct Reduction of 1-Bromo-6-chlorohexane and 1-Chloro-6-iodohexane at Silver Cathodes in Dimethylformamide

Rose, John A.,McGuire, Caitlyn M.,Hansen, Angela M.,Karty, Jonathan A.,Mubarak, Mohammad S.,Peters, Dennis G.

, p. 311 - 317 (2016)

Cyclic voltammetry and controlled-potential (bulk) electrolyses have been employed to probe the electrochemical reductions of 1-bromo-6-chlorohexane and 1‐chloro-6-iodohexane at silver cathodes in dimethylformamide (DMF) containing 0.050?M tetra-n-butylammonium tetrafluoroborate (TBABF4). A cyclic voltammogram for reduction of 1-bromo-6-chlorohexane shows a single major irreversible cathodic peak, whereas reduction of 1-chloro-6-iodohexane gives rise to a pair of irreversible cathodic peaks. Controlled-potential (bulk) electrolyses of 1-bromo-6-chlorohexane at a silver gauze cathode reveal that the process involves a two-electron cleavage of the carbon–bromine bond to afford 1-chlorohexane as the major product, along with 6-chloro-1-hexene, n‐hexane, 1‐hexene, and 1,5-hexadiene as minor species. In contrast, bulk electrolyses of 1-chloro-6-iodohexane indicate that the first voltammetric peak corresponds to a one-electron process, leading to production of a dimer (1,12-dichlorododecane) together with 1-chlorohexane and 6-chloro-1-hexene as well as 1‐hexene and 1,5-hexadiene in trace amounts. At potentials corresponding to the second cathodic peak, reduction of 1-chloro-6-iodohexane is a mixture of one- and two-electron steps that yields the same set of products, but in different proportions. Mechanistic schemes are proposed to explain the electrochemical behavior of both 1‐bromo-6-chlorohexane and 1-chloro-6-iodohexane.

Calcium Hydride Cation [CaH]+ Stabilized by an NNNN-type Macrocyclic Ligand: A Selective Catalyst for Olefin Hydrogenation

Schuhknecht, Danny,Lhotzky, Carolin,Spaniol, Thomas P.,Maron, Laurent,Okuda, Jun

, p. 12367 - 12371 (2017)

Reaction of dibenzyl calcium complex [Ca(Me4TACD)(CH2Ph)2], containing the neutral NNNN-type macrocyclic ligand Me4TACD (Me4TACD=1,4,7,10-tetramethyl-1,4,7,10-tetraazacyclododecane), with triphenylsilane gave the cationic dinuclear calcium hydride [Ca2H2(Me4TACD)2](PhCHSiPh3)2 which was characterized by NMR spectroscopy and single-crystal X-ray diffraction. The cation can be regarded as the ligand-stabilized dimeric form of hypothetical [CaH]+. Hydrogenolysis of benzyl calcium cation [Ca(Me4TACD)(CH2Ph)(thf)]+ gave dicationic calcium hydrides [Ca2H2(Me4TACD)2][BAr4]2 (Ar=C6H4-4-tBu; C6H3-3,5-Me2) containing weakly coordinating anions. In THF, they catalyzed the isotope exchange of H2 and D2 to give HD and the hydrogenation of unactivated 1-alkenes.

Biphasic hydroformylation of 1-hexene with carbon dioxide catalyzed by ruthenium complex in ionic liquids

Tominaga, Ken-Ichi,Sasaki, Yoshiyuki

, p. 14 - 15 (2004)

Hydroformylation of 1-hexene using carbon dioxide as carbonyl carbon source attained high yield and good chemoselectivity in heptanols when a ruthenium complex was used in biphasic ionic liquid-toluene system.

Cationic pyridyl(benzoazole) ruthenium(II) complexes: Efficient and recyclable catalysts in biphasic hydrogenation of alkenes and alkynes

Ogweno, Aloice O.,Ojwach, Stephen O.,Akerman, Matthew P.

, p. 250 - 258 (2014)

The synthesis, structural characterization of cationic 2-(2-pyridyl)benzoazole)ruthenium(II) complexes and their applications in biphasic hydrogenations of alkenes is reported. Reactions of 2-(2-pyridyl)benzoimidazole (L1), 2-(2-pyridyl)benzothiazole (L2) and 2-(2-pyridyl)benzoxazole (L3) with [η6-(2-phenoxyethanol)RuCl2]2produced the corresponding cationic complexes [η6-(2-phenoxyethanol)RuCl(L1)]Cl (1), [η6-(2-phenoxyethanol)RuCl(L2)]Cl (2) and [η6-(2-phenoxyethanol)RuCl(L3)]Cl (3) in good yields. Solid state structures of 1-3 confirmed the bidentate coordination modes of L1-L3 and formation of cationic species through displacement of one chloride ligand from Ru(II) coordination sphere. Complexes 1-3 produced active catalysts for high pressure hydrogenation of alkenes both in methanol and biphasic conditions. Relatively lower activities were observed in the hydrogenation of terminal alkynes giving a mixture of alkane and alkene products. Complexes 1-3 were recyclable under biphasic conditions and retained significant catalytic activities in six cycles. Reaction parameters such as substrate/catalyst ratio, temperature, and aqueous/organic ratio affected the catalytic trends.

-

Greenfield et al.

, p. 1258 (1954)

-

Pd Nanocubes@ZIF-8: Integration of Plasmon-Driven Photothermal Conversion with a Metal-Organic Framework for Efficient and Selective Catalysis

Yang, Qihao,Xu, Qiang,Yu, Shu-Hong,Jiang, Hai-Long

, p. 3685 - 3689 (2016)

Composite nanomaterials usually possess synergetic properties resulting from the respective components and can be used for a wide range of applications. In this work, a Pd nanocubes@ZIF-8 composite material has been rationally fabricated by encapsulation of the Pd nanocubes in ZIF-8, a common metal-organic framework (MOF). This composite was used for the efficient and selective catalytic hydrogenation of olefins at room temperature under 1 atm H2 and light irradiation, and benefits from plasmonic photothermal effects of the Pd nanocube cores while the ZIF-8 shell plays multiple roles; it accelerates the reaction by H2 enrichment, acts as a "molecular sieve" for olefins with specific sizes, and stabilizes the Pd cores. Remarkably, the catalytic efficiency of a reaction under 60 mW cm-2 full-spectrum or 100 mW cm-2 visible-light irradiation at room temperature turned out to be comparable to that of a process driven by heating at 50 °C. Furthermore, the catalyst remained stable and could be easily recycled. To the best of our knowledge, this work represents the first combination of the photothermal effects of metal nanocrystals with the favorable properties of MOFs for efficient and selective catalysis.

TRANSFORMATIONS OF n-HEXANE AND 1-HEXENE ON ALUMINUM, GALLIUM, AND INDIUM OXIDES

Bryukhanov, V. G.,Rozengart, M. I.,Isagulyants, G. V.

, p. 613 - 616 (1980)

-

Further studies of the PtII/SnCl2 catalyzed hydroformylation

Scrivanti, A.,Paganelli, S.,Matteoli, U.,Botteghi, C.

, p. 439 - 446 (1990)

A convenient synthesis of the complexes trans- and trans- is described, and their NMR spectra in the presence of SnCl2 are discussed.These complexes have been examined as catalysts in 1-hexene hydroformylation in the presence of an excess of SnCl2.Their catalytic behaviour is compared with that of the systems based on complexes trans-, trans-, trans-, and cis-.

Heterolytic H2 activation on a carbene-ligated rhodathiaborane promoted by isonido-nido cage opening

Calvo, Beatriz,Macias, Ramon,Polo, Victor,Artigas, Maria Jose,Lahoz, Fernando J.,Oro, Luis A.

, p. 9863 - 9865 (2013)

A new mechanism of H2 activation is reported to occur on a carbene-ligated rhodathiaborane that features metal-thiaborane bifunctional synergistic effects. The key is the creation of vacant coordination sites by an isonido-nido structural transformation leading to the heterolytic H-H bond splitting.

Development of silica-supported frustrated Lewis pairs: Highly active transition metal-free catalysts for the Z-selective reduction of alkynes

Szeto, Kai C.,Sahyoun, Wissam,Merle, Nicolas,Castelbou, Jessica Llop,Popoff, Nicolas,Lefebvre, Frédéric,Raynaud, Jean,Godard, Cyril,Claver, Carmen,Delevoye, Laurent,Gauvin, Régis M.,Taoufik, Mostafa

, p. 882 - 889 (2016)

Supported Lewis acid/base systems based on a triphenyl phosphine fragment and Piers' reagent (HB(C6F5)2) or BArF have been prepared and characterized. Both materials show unprecedented catalytic activity in the Z-selective hydrogenation of 3-hexyne to Z-3-hexene with a selectivity up to 87%. Other alkynes can also be hydrogenated Z-selectively, albeit with moderate yields. The activity of the supported phosphine/HB(C6F5)2 adduct is similar to the only homogeneous example reported thus far based on bridged B/N frustrated Lewis pairs under high hydrogen pressure. Importantly, this transition metal-free supported catalyst was recycled five times in the challenging selective hydrogenation of a non-polar unactivated alkyne.

Investigation of a system of protecting layer for the process of hydrorefining oily distillates of Uzbekistan's petroleum

Yunusov,Molodozhenyuk,Ergashev,Dzhalalova,Gashenko,Saidulaev

, p. 1207 - 1212 (2007)

Complex investigation is conducted, directed to development of contacting materials (forcontacts) and catalysts for the protecting layer in the process of hydrorefining petroleum distillates taking into account their specificity and extensively attracting local raw materials. Forcontact FZS-7 is developed which, besides the function of uniform distribution of crude material over the reactor section, diminishes tarring and performs, owing to low nickel content, mild hydrogenation of unsaturated compounds. The proposed kaolin-bset catalyst of the protecting layer with low content of molybdenum oxide works reliably with the residual crude material with high content of iron and displays high enough demetallization activity.

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Habeeb,Tuch

, p. 696 (1976)

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Brown,Murray

, p. 4108 (1959)

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STUDY OF THE CATALYTIC ACTIVITY OF METAL COMPLEXES FIXED ON SOLID SUPPORTS. 7. SYNTHESIS OF Pd-Sn COMPLEXES ATTACHED TO MACROPOROUS ANION EXCHANGERS AND STUDY OF THEIR ACTIVITY IN THE HYDROGENATION OF 1-HEXENE

Sharf, V. Z.,Panfilova, L. D.,Borunova, N. V.,Antseva, N. V.,Karapetyan, L. P.,et al.

, p. 695 - 698 (1989)

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Electrochemical Reduction of 1,6-Dihalohexanes at Carbon Cathodes in Dimethylformamide

Mubarak, Mohammad S.,Peters, Dennis G.

, p. 681 - 685 (1995)

Cyclic voltammograms for the reduction of 1,6-dibromo-, 1,6-diiodo-, 1-bromo-6-chloro-, and 1-chloro-6-iodohexane at glassy carbon electrodes in dimethylformamide containing tetramethylammonium perchlorate exhibit single irreversible waves that correspond to the reductive cleavage of carbon-bromine or carbon-iodine bonds.When large-scale controlled-potential electrolyses of either 1,6-dibromo- or 1,6-diiodohexane are performed at reticulated vitreous carbon, the principal products are n-hexane (30-45percent), 1-hexene (28-34percent), 1,5-hexadiene (6-16percent), and cyclohexane (7percent), with n-dodecane being another significant species obtained from 1,6-diiodohexane.Because a carbon-chlorine bond is not directly reducible, 1-bromo-6-chloro- and 1-chloro-5-iodohexane give rise mainly to 1-chlorohexane (47-64percent), 6-chloro-1-hexene (20-33percent), and 1,12-dichlorododecane (2-25percent).From these product distributions, and with the aid of experiments done in the presence of deuterium-labeled reagents, we conclude that the electrolytic reduction of 1,6-diiodo- and 1-chloro-6-iodohexane involves both radical and carbanion intermediates, whereas only carbanionic pathways are important for electrolyses of 1,6-dibromo- and 1-bromo-6-chlorohexane.

Decarboxylation and further transformation of oleic acid over bifunctional, Pt/SAPO-11 catalyst and Pt/chloride Al2O3 catalysts

Ahmadi, Masoudeh,Macias, Eugenia E.,Jasinski, Jacek B.,Ratnasamy, Paul,Carreon, Moises A.

, p. 14 - 19 (2014)

Catalytic decarboxylation and further conversion of oleic acid to branched and aromatic hydrocarbons in a single process step, over Pt-SAPO-11 and Pt/chloride Al2O3 is presented. An increase of both reaction time and temperature increase the selectivity to heptadecane. Higher selectivity to heptadecane was observed in the presence of hydrogen. Decarboxylation of oleic acid was as high as ~98 wt% (selectivity for heptadecane >30%) at 325 C in the presence of hydrogen. Branched isomers, alkyl aromatics, like dodecyl benzene and cracked (17) paraffins were the other products.

Effects of Catalyst Site Accessibility on Catalysis by Rhodium(I) Complexes of Amphiphilic Ligands (1+) (n = 2,3,6,or 10) tethered to a Cation-exchange Resin

Renaud, Eric,Baird, Michael C.

, p. 2905 - 2906 (1992)

The effects of catalyst site accessibility on the activities of supported olefin hydrogenation catalysts have been assessed utilizing the complexes 3 4-norbornadiene; L = Ph2P(CH2)nPMe3(1+); n = 2, 3, 6 or 10> tethered to a cation-exchange resin via the tetraalkylphosphonium moieties of the co-ordinated ligands; the most active catalysts are those containing the longer-chain ligands, where the catalyst sites are farthest removed from steric hindrance by the resin surface.

Cryosynthesis of catalysts for propylene oligomerization based on titanium tetrachloride and magnesium

Tarkhanova,Smirnov,Tsvetkova,Tjurina

, p. 891 - 894 (1999)

A highly dispersed catalyst for oligo- and polymerization of propylene was synthesized by the interaction of TiCl4 with magnesium in the cocondensates of their vapor with benzene and pentane. The catalyst contains MgCl2 and organotitanium and organomagnesium cluster derivatives. The transformations of propylene and hex-1-ene over the catalysts were studied. The direction of catalytic reactions and activity of the catalyst depend on the TiCl4 : Mg molar ratio and the hydrocarbon used. Systems with an equimolar ratio of the reactants obtained in a benzene matrix exhibit the highest activity. Propylene oligomers containing a considerable fraction of unsaturated bonds are formed in the presence of the catalysts at room temperature and a pressure of 300 Torr.

Artificial metalloenzymes via encapsulation of hydrophobic transition-metal catalysts in surface-crosslinked micelles (SCMs)

Zhang, Shiyong,Zhao, Yan

, p. 9998 - 10000 (2012)

Encapsulation of a hydrophobic rhodium catalyst in crosslinked micelles allowed nonpolar substrates to react in water with unusual selectivity. This journal is The Royal Society of Chemistry 2012.

Hydrogenation of unsaturated hydrocarbons catalyzed by homogeneous and supported Rh, Rh-Co, and Pd, Pd-Ni complexes with oligomeric allene ligands

Khar'kova,Rozantseva,Frolov

, p. 214 - 219 (2010)

Mono-and bimetallic Rh and Rh-Co complexes containing oligoallene ligands were synthesized. Their catalytic activity was examined in the hydrogenation of unsaturated compounds, such as isoprene, hexene-1, and toluene. The catalytic activity of Rh(DMA)ol and Rh-Co(DMA)ol was shown to be 16 800 and 23000 mol/(mol h) in the hydrogenation of hexene-1 and 72 and 90 mol/(mol h) in the hydrogenation of toluene, respectively. Isoprene is hydrogenated completely: the rate curves exhibit two portions corresponding to hydrogenation of both double bonds. The catalytic activity of palladium oligodimethylallene complexes deposited on an inorganic support (γ-Al 2O3) in isoprene hydrogenation depends on the support preparation procedure, the particle size, and the metal loading on the surface. Heterogenization of the homogeneous mono-and bimetallic Rh and Pd complexes somewhat enhances the catalytic activity in hydrogenation of the given substrates. Pleiades Publishing, Ltd., 2010.

Ruthenium carbonyl carboxylates with nitrogen containing ligands: IV. Catalytic activity in the hydroformylation of olefins in homogeneous phase 1

Frediani, Piero,Bianchi, Mario,Salvini, Antonella,Carluccio, Luciano C.,Rosi, Luca

, p. 35 - 40 (1997)

Ruthenium carbonyl acetato complexes containing bipyridines or phenantrolines ligands are tested as catalysts in the hydroformylation of hex-1-ene in homogeneous phase. These catalysts are active also in solutions containing water and the selectivity to aldehyde is high. Only a moderate hydrogenation of the alkene occurs. The regioselectivity to the linear aldehyde reaches 85.7% when using the mononuclear complex containing 4,7-dmphen as ligand. In the course of the reaction the starting olefm is largely isomerized.

The catalytic activity of alkali metal alkoxides and titanium alkoxides in the hydrosilylation of unfunctionalized olefins

Yang, Xiaoling,Bai, Ying,Li, Jiayun,Liu, Yu,Peng, Jiajian,Li, Tianbo,Lang, Rui,Qiao, Botao

, p. 83 - 86 (2019)

The catalytic activities of titanium alkoxides and alkali metal alkoxides for hydrosilylation of unfunctionalized olefins have been studied. Titanium(IV) alkoxides showed excellent catalytic activity, while alkali metal alkoxides have low catalytic activity for the hydrosilylation of olefins. However, by using titanocene dichloride as an additive, alkali metal alkoxides showed also excellent catalytic property for hydrosilylation. In comparison with titanium alkoxides, no α-adduct was obtained by using alkali metal alkoxides/Cp2TiCl2 as catalysts.

KINETICS OF HYDROGENATION OF 1-HEXENE IN THE PRESENCE OF AROMATIC HYDROCARBONS ON PALLADIUM SULFIDE CATALYST

Matveeva, T. M.,Nekrasov, N. V.,Kostyukovskii, M. M.,Navalikhina, M. D.,Krichko, A. A.,Kiperman, S. L.

, p. 1104 - 1110 (1982)

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Fabricating nickel phyllosilicate-like nanosheets to prepare a defect-rich catalyst for the one-pot conversion of lignin into hydrocarbons under mild conditions

Cao, Meifang,Chen, Bo,He, Chengzhi,Ouyang, Xinping,Qian, Yong,Qiu, Xueqing

supporting information, p. 846 - 857 (2022/02/09)

The one-pot conversion of lignin biomass into high-grade hydrocarbon biofuels via catalytic hydrodeoxygenation (HDO) holds significant promise for renewable energy. A great challenge for this route involves developing efficient non-noble metal catalysts to obtain a high yield of hydrocarbons under relatively mild conditions. Herein, a high-performance catalyst has been prepared via the in situ reduction of Ni phyllosilicate-like nanosheets (Ni-PS) synthesized by a reduction-oxidation strategy at room temperature. The Ni-PS precursors are partly converted into Ni0 nanoparticles by in situ reduction and the rest remain as supports. The Si-containing supports are found to have strong interactions with the nickel species, hindering the aggregation of Ni0 particles and minimizing the Ni0 particle size. The catalyst contains abundant surface defects, weak Lewis acid sites and highly dispersed Ni0 particles. The catalyst exhibits excellent catalytic activity towards the depolymerization and HDO of the lignin model compound, 2-phenylethyl phenyl ether (PPE), and the enzymatic hydrolysis of lignin under mild conditions, with 98.3% cycloalkane yield for the HDO of PPE under 3 MPa H2 pressure at 160 °C and 40.4% hydrocarbon yield for that of lignin under 3 MPa H2 pressure at 240 °C, and its catalytic activity can compete with reported noble metal catalysts.

Conversion of Phenol and Lignin as Components of Renewable Raw Materials on Pt and Ru-Supported Catalysts

Bobrova, Nataliia A.,Bogdan, Tatiana V.,Bogdan, Viktor I.,Koklin, Aleksey E.,Mishanin, Igor I.

, (2022/03/01)

Hydrogenation of phenol in aqueous solutions on Pt-Ni/SiO2, Pt-Ni-Cr/Al2 O3, Pt/C, and Ru/C catalysts was studied at temperatures of 150–250? C and pressures of 40–80 bar. The possibility of hydrogenation of hydrolysis lignin in an aqueous medium in the presence of a Ru/C catalyst is shown. The conversion of hydrolysis lignin and water-soluble sodium lignosulfonate occurs with the formation of a complex mixture of monomeric products: a number of phenols, products of their catalytic hydrogenation (cyclohexanol and cyclohexanone), and hydrogenolysis products (cyclic and aliphatic C2 –C7 hydrocarbons).

Room temperature iron catalyzed transfer hydrogenation usingn-butanol and poly(methylhydrosiloxane)

Coles, Nathan T.,Linford-Wood, Thomas G.,Webster, Ruth L.

supporting information, p. 2703 - 2709 (2021/04/21)

Reduction of carbon-carbon double bonds is reported using a three-coordinate iron(ii) β-diketiminate pre-catalyst. The reaction is believed to proceedviaa formal transfer hydrogenation using poly(methylhydrosiloxane), PMHS, as the hydride donor and a bio-alcohol as the proton source. The reaction proceeds well usingn-butanol and ethanol, withn-butanol being used for substrate scoping studies. Allyl arene substrates, styrenes and aliphatic substrates all undergo reduction at room temperature. Unfortunately, clean transfer of a deuterium atom usingd-alcohol does not take place, indicating a complex catalytic mechanism. However, changing the deuterium source tod-aniline gives close to complete regioselectivity for mono-deuteration of the terminal position of the double bond. Finally, we demonstrate that efficient dehydrocoupling of alcohol and PMHS can be undertaken using the same pre-catalyst, giving high yields of H2within 30 minutes at room temperature.

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