124-18-5

Basic information

• Product Name: Decane
• Synonyms: decanenormal;n-C10H22;N-DECANE;n-Decyl hydride;Decyl hydride;DECANE;'LGC' (2033);Decane, pure, 99+%
• CAS NO: 124-18-5
• Molecular Formula: C₁₀H₂₂
• Molecular Weight: 142.28
• EINECS: 204-686-4
• Product Categories: Anhydrous Solvents;Carthamus tinctorius (Safflower oil);Nutrition Research;Phytochemicals by Plant (Food/Spice/Herb);Solvent Bottles;Solvent by Application;Solvent Packaging Options;Sure/Seal Bottles;ACS and Reagent Grade Solvents;Amber Glass Bottles;ReagentPlus;ReagentPlus Solvent Grade Products;Pharmaceutical Intermediates;Analytical Chemistry;n-Paraffins (GC Standard);Standard Materials for GC;Anhydrous Grade SolventsSolvents;Solvent Bottles;Solvents;Sure/Seal? Bottles;Alpha Sort;D;DA - DH;DAlphabetic;Volatiles/ Semivolatiles;Amber Glass Bottles;ReagentPlus(R) Solvent Grade Products;ReagentPlus(R)Solvents;Alphabetic;DA - DHChemical Class;Hydrocarbons;Neats
• Mol File: 124-18-5.mol

Chemical Properties

• Melting Point: -30 °C
• Boiling Point: 174 °C(lit.)
• Flash Point: 115 °F
• Appearance: Colorless/Liquid
• Density: 0.735
• Vapor Density: 4.9 (vs air)
• Vapor Pressure: 1 mm Hg ( 16.5 °C)
• Refractive Index: n20/D 1.411(lit.)
• Storage Temp.: Flammables area
• Solubility: 0.00005g/l
• Explosive Limit: 0.7-5.4%(V)
• Water Solubility: INSOLUBLE
• Stability: Stable. Incompatible with oxidizing agents. Flammable.
• BRN: 1696981
• CAS DataBase Reference: Decane(CAS DataBase Reference)
• NIST Chemistry Reference: Decane(124-18-5)
• EPA Substance Registry System: Decane(124-18-5)

Safety Data

• Hazard Codes: Xn,N,F
• Statements: 10-65-66-67-62-51/53-48/20-38-11
• Safety Statements: 62-23-16-61-36/37-33-29-9
• RIDADR: UN 2247 3/PG 3
• WGK Germany: 3
• RTECS: HD6550000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 124-18-5(Hazardous Substances Data)

Usage

Uses

Decane is used in various applications across different industries due to its unique properties. Here are some of its uses:
1. Used in the Gasoline Industry:
Decane is a component of engine fuel and is used in organic synthesis, as a solvent, as a standardized hydrocarbon, and in jet fuel research.
2. Used in the Petroleum Industry:
Decane is a constituent in the paraffin fraction of petroleum and is used as a solvent in organic synthesis reactions, as a hydrocarbon standard in the manufacture of petroleum products, and as a constituent in polyolefin manufacturing wastes.
3. Used in the Rubber Industry:
Decane is utilized as a solvent in the rubber industry, where it plays a crucial role in the production process.
4. Used in the Paper Processing Industry:
Decane is employed as a solvent in the paper processing industry, contributing to the manufacturing of various paper products.
5. Used in the Plastics Industry:
Decane is released to the environment through the manufacture, use, and disposal of products associated with the plastics industry.
6. Used as an Internal Standard in Gas Chromatography (GC) Analysis:
Decane is used as an internal standard in the GC analysis of oxalic, malonic, and succinic acids in biological materials, ensuring accurate and reliable results.

Reactions

The Combustion Reaction of Decane is as follows:Like all hydrocarbons, decane undergoes hydrocarbon combustion when used as a fuel. The balanced chemical equation for the complete combustion of decane is:?2 C10H22 + 31 O2 → 20 CO2 + 22 H2O + Heat Energy (Enthalpy)?The hydrocarbon combustion reaction releases heat energy and is an example of an exothermic reaction. The reaction also has a negative enthalpy change (ΔH) value.

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 2259, 1978 DOI: 10.1021/jo00405a036Tetrahedron Letters, 34, p. 3745, 1993 DOI: 10.1016/S0040-4039(00)79216-1

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

DECANE is incompatible with oxidizing agents.

Health Hazard

Contact with eyes may produce mild irritation. Contact with skin may cause defatting, redness, scaling, and hair loss. Ingestion may cause diarrhea, slight central nervous system depression, difficulty in breathing and fatigue. Inhalation of high concentrations may cause rapid breathing, fatigue, headache, dizziness, and other CNS effects.

Fire Hazard

Special Hazards of Combustion Products: May produce toxic fumes, including carbon monoxide.

Flammability and Explosibility

Flammable

Biochem/physiol Actions

Decane-1,2-diol derivative might prevent cancer development.

Safety Profile

Questionable carcinogen with experimental tumorigenic data. A simple asphyxiant. Narcotic in high concentrations, Flammable liquid when exposed to heat or flame. Can react with oxidizing materials. Moderately explosive in its vapor form. To fight fire, use foam, CO2, dry chemical. Emitted from modern buildtng materials (CENEAR 69,22,91). See also ARGON for discussion of asphyxiants.

Carcinogenicity

Mice treated with decane developed tumors on the backs, after exposure to ultraviolet radiation at wavelengths longer than 350 nm, generally considered noncarcinogenic. A series of 21 tobacco smoke components and related compounds were applied to mouse skin (50 female ICR/Ha Swiss mice/group) three times weekly with 5 mug/application of benzo[a]pyrene (B[a]P). The test compounds were of five classes: aliphatic hydrocarbons, aromatic hydrocarbons, phenols, and longchain acids and alcohols. Decane was among the compounds that enhanced remarkably the carcinogenicity of B[a]P. and also acted as tumor promoter in two-stage carcinogenesis.

Source

Major constituent in paraffin (quoted, Verschueren, 1983). Identified as one of 140 volatile constituents in used soybean oils collected from a processing plant that fried various beef, chicken, and veal products (Takeoka et al., 1996). California Phase II reformulated gasoline contained decane at a concentration of 1,120 mg/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 300 and 42,600 μg/km, respectively (Schauer et al., 2002).

Environmental fate

Biological. Decane may biodegrade in two ways. The first is the formation of decyl hydroperoxide, which decomposes to 1-decanol, followed by oxidation to decanoic acid. The other pathway involves dehydrogenation to 1-decene, which may react with water giving 1-decanol (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 the corresponding alcohol (1-decanol). The alcohol may undergo a series of dehydrogenation steps, forming decanal, followed by oxidation forming decanoic acid. The fatty acid may then be metabolized by β-oxidation to form the mineralization products, carbon dioxide and water (Singer and Finnerty, 1984). Hou (1982) reported 1-decanol and 1,10-decanediol as degradation products by the microorganism Corynebacterium.Photolytic. A photooxidation reaction rate constant of 1.16 x 10-11 cm3/molecule?sec was reported for the reaction of decane with OH in the atmosphere (Atkinson, 1990). Chemical/Physical. Complete combustion in air yields carbon dioxide and water vapor. Decane will not hydrolyze because it has no hydrolyzable functional group.

Purification Methods

It can be purified by shaking with conc H2SO4, washing with water, aqueous NaHCO3, and more water, then drying with MgSO4, refluxing with Na and distilling. Also purify through a column of silica gel or alumina. It has been purified by azeotropic distillation with 2-butoxyethanol, the alcohol being washed out of the distillate, using water, the decane is next dried and redistilled. It can be stored with NaH. Further purification can be achieved by preparative gas chromatography on a column packed with 30% SE-30 (General Electric methyl-silicone rubber) on 42/60 Chromosorb P at 150o and 40psig, using helium [Chu J Chem Phys 41 226 1964]. It is soluble in EtOH and Et2O. [Beilstein 1 IV 484.]

Toxicity evaluation

If released to air, n-decane will exist solely as a vapor in the ambient atmosphere. Vapor-phase n-decane will be degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals, the half-life for this reaction in air is approximately 11.5 h.Based on n-decane’s vapor pressure, it may volatilize from dry soil surfaces. In biodegradation studies in soil, hydrocarbons with molecular weights equivalent to or lower than decane disappeared from the soil in both active and sterile treatments by the first sampling time (5 days), indicating that evaporation was a major removal process. Decane is expected to have low to no mobility in soil based on estimated organic carbon partition coefficient (Koc) values in the range of 1700– 43 000. Volatilization from moist soil surfaces is expected to be an important fate process based on a Henry’s law constant of 5.2 atm m3 mol-1, which is calculated from n-decane’s vapor pressure and water solubility. Adsorption to soil, however, would be expected to attenuate due to volatilization.

InChI:InChI=1/C10H22/c1-3-5-7-9-10-8-6-4-2/h3-10H2,1-2H3

Synthetic route

1-Decene (872-05-9) → decane (124-18-5)

Conditions	Yield
With {(η6-C6H6)Ru(NCCH3)3}{BF4}2; water; hydrogen In benzene at 90℃; under 30400 Torr; for 4h;	100%
With hydrogen; Rh on carbon at 75℃; under 3040.2 Torr; for 0.35h;	100%
With hydrazine hydrate In ethanol for 24h; Reflux;	100%

(1-methyl-nonyloxy)-diphenyl-silane → decane (124-18-5)

Conditions	Yield
With indium(III) chloride In dichloromethane-d2 at 20℃;	100%

pentane (109-66-0) → decane (124-18-5)

Conditions	Yield
With di-tert-butyl peroxide; iodine	100%

1-decyne (764-93-2) → decane (124-18-5)

Conditions	Yield
With hydrogen In methanol at 20℃; for 18h;	98%
With hydrogen In ethanol at 100℃; under 30003 Torr; Flow reactor; Green chemistry; chemoselective reaction;	67%
With hydrogen In methanol at 20℃; under 5171.62 Torr; for 24h;	98 %Chromat.

1-decyne (764-93-2) → decane (124-18-5) + 1-Decene (872-05-9)

Conditions	Yield
With hydrogen In hexane at 40℃; under 760.051 Torr; for 5h;	A 3% B 97%
With hydrogen; Ni-Gr2 In methanol at 30℃; under 22800 Torr; for 6h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogen; ethylenediamine In tetrahydrofuran at 25℃; under 760 Torr;	A 13 % Chromat. B 75 % Chromat.

Iododecane (2050-77-3) → decane (124-18-5) + icosane (112-95-8)

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide Electrochemical reaction; Inert atmosphere;	A 1% B 97%
With sodium polystyrylanthracene Product distribution;	A 25% B 4%

Iododecane (2050-77-3) → decane (124-18-5)

Conditions	Yield
With Li(1+)*C12H28AlO3(1-) In tetrahydrofuran; hexane for 0.0333333h; Ambient temperature;	96%
With LiPyrrBH3 In tetrahydrofuran at 0℃;	92%
With sodium tetrahydroborate In various solvent(s) at 70℃; for 3h;	82%

1-bromo dodecane (112-29-8) → decane (124-18-5)

Conditions	Yield
With Li(1+)*C12H28AlO3(1-) In tetrahydrofuran; hexane for 0.166667h; Ambient temperature;	95%
With [2-(di-tert-butylphosphinomethyl)-6-(diethylaminomethyl)pyridine]ruthenium(II) chlorocarbonyl hydride; isopropyl alcohol; sodium t-butanolate at 100℃; for 18h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube; Green chemistry;	93%
With sodium tetrahydroborate In various solvent(s) at 70℃; for 12h;	82%

hexanoic acid (142-62-1) → decane (124-18-5)

Conditions	Yield
With sodium methylate In methanol Kolbe Electrolysis; Electrochemical reaction;	95%
With sodium hydroxide at 19.84℃; pH=6.1; Kolbe reaction; Electrochemical reaction;	45 % Spectr.
With sodium methylate In methanol at 40 - 60℃; Electrolysis;

1,10-dibromodecane (4101-68-2) → decane (124-18-5)

Conditions	Yield
With sodium tetrahydroborate; cetyltributylphosphonium bromide In water; toluene at 18℃; for 5h; Product distribution;	94%
With diethyl ether; sodium
With iron(III) chloride; phenylsilane; sodium methylate In tetrahydrofuran for 6h; Schlenk technique; Inert atmosphere;	61 %Chromat.

Iododecane (2050-77-3) → decane (124-18-5) + 1-Decanol (112-30-1)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tributyltin chloride; oxygen; sodium cyanoborohydride In tert-butyl alcohol at 60℃; for 14h; Yields of byproduct given;	A n/a B 93%

1,10-diiododecane (16355-92-3) → decane (124-18-5)

Conditions	Yield
With nickel In tetrahydrofuran at 20℃; for 6h;	92%
With diethyl ether; magnesium und Zers. des Reaktionsproduktes mit Wasser;

N-Phenoxyundecanamide (351464-82-9) → decane (124-18-5)

Conditions	Yield
With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran for 2h; Heating;	92%

5-decyne (1942-46-7) → decane (124-18-5)

Conditions	Yield
With Triethoxysilane; water; propynoic acid methyl ester; palladium diacetate In tetrahydrofuran for 24h; Ambient temperature;	90%
With methanol; nickel Hydrogenation;
With hydrogen In glycerol at 80℃; under 750.075 Torr; for 2h;	90 %Chromat.
With C5H14NO(1+)*C10H12NO4S(1-)*Pd; hydrogen In glycerol at 80℃; under 2250.23 Torr; for 2h; Inert atmosphere; Schlenk technique;	96 %Chromat.

Iododecane (2050-77-3) + tri-n-butyl-tin hydride (688-73-3) → decane (124-18-5)

Conditions	Yield
In toluene Sonication; ultrasound irradiation of a mixt. of Bu2SnH and 1-iododecane in toluene, 0-6 °C, 1h;;	90%
In toluene react. of a mixt. of Bu3SnH and 1-iododecane in toluene, 0 °C, 1h;;	5%

decyl chloride (1002-69-3) → decane (124-18-5)

Conditions	Yield
With hydrogen; NiCl2-Li-[poly(2-vinyl-naphthalene)-co-(divinylbenzene)] In tetrahydrofuran at 20℃; under 760.051 Torr; for 2.5h;	89%
With sodium tetrahydroborate In various solvent(s) at 70℃; for 16h;	78%
With naphthalene; hydrogen; lithium; nickel dichloride In tetrahydrofuran at 20℃; under 760.051 Torr; for 2h;	68%

1-decanoic acid (334-48-5) → decane (124-18-5)

Conditions	Yield
With hydrogen In neat (no solvent) at 180℃; under 6000.6 Torr; for 24h; Catalytic behavior; Autoclave; High pressure;	88%
With hydrogen In hexane at 160℃; under 22502.3 Torr; for 18h; Molecular sieve; chemoselective reaction;	87%
With phosphorus; hydrogen iodide at 210 - 240℃;

N-Methoxyundecanamide (351464-79-4) → decane (124-18-5)

Conditions	Yield
With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran for 2h; Heating;	87%

4-methylbenzenesulfonic acid 6-chlorohexyl ester (71042-21-2) + ethylmagnesium bromide (925-90-6) → decane (124-18-5) + 1-Chlorooctane (111-85-3)

Conditions	Yield
With buta-1,3-diene; nickel dichloride In tetrahydrofuran at 20℃; for 3h;	A 13% B 87%

n-decyl magnesium bromide (17049-50-2) + benzophenone N-methyl-N,N-pentane-1,5-diylhydrazonium iodide (13134-23-1) → N-methylcyclohexylamine (626-67-5) + Benzophenone imine (1013-88-3) + decane (124-18-5) + icosane (112-95-8) + 1-Decene (872-05-9)

Conditions	Yield
In diethyl ether Product distribution; Mechanism; Heating; other quaternary hydrazonium salts, other alkylmagnesium halides;	A 85% B 84% C 51% D 21% E 25%

2-decyl N-trimethylsilylmethylthionocarbamate → decane (124-18-5) + decan-2-ol (1120-06-5)

Conditions	Yield
With triethylsilane; di-tert-butyl peroxide In benzene at 140℃; Mechanism; Product distribution; or with benzoyl peroxide, or with n-Bu3SnH, other temperature, other thionocarbamates;	A 85% B 3%

octylmagnesium bromide (17049-49-9) + (Z)-1,2-bis(ethylseleno)ethene (175538-67-7) → decane (124-18-5) + octadeca-9Z-ene (1779-13-1) + Hexadecane (544-76-3)

Conditions	Yield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In diethyl ether at 20℃; for 9h;	A 56 mg B 85% C 115 mg

N-Benzyloxyundecanamide (105249-97-6) → decane (124-18-5)

Conditions	Yield
With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran for 2h; Heating;	83%

1-Decene (872-05-9) + carbon monoxide (201230-82-2) → decane (124-18-5) + undecyl alcohol (112-42-5) + 2-methyldecan-1-ol (18675-24-6) + 2-methyldecanal (19009-56-4) + undecylaldehyde (112-44-7)

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium; 2-(dicyclohexylphosphino)-1-methyl-1H-imidazole; water; hydrogen; lithium chloride In 1-methyl-pyrrolidin-2-one at 130℃; under 60 Torr; for 20h; Autoclave; regioselective reaction;	A 6 %Chromat. B 83% C n/a D n/a E n/a

1-methoxydecane (7289-52-3) → decane (124-18-5)

Conditions	Yield
With chloro-trimethyl-silane; acetic acid; sodium iodide; zinc In acetonitrile Product distribution; 1.) 70 - 75 deg C, 1.5 h; 2.) 75 - 85 deg C, 4.5 h; various ethers;	82%

decyl p-toluenesulfonate (5509-08-0) → decane (124-18-5)

Conditions	Yield
With sodium tetrahydroborate In various solvent(s) at 70℃; for 3h;	82%
With tri-n-butyl-tin hydride; sodium iodide In 1,2-dimethoxyethane at 80℃; for 1h; Heating;	73%

1-bromo-octane (111-83-1) + ethylmagnesium chloride (2386-64-3) → decane (124-18-5)

Conditions	Yield
With buta-1,3-diene; copper dichloride In tetrahydrofuran at 50℃; for 12h;	82%
With N,N,N,N,-tetramethylethylenediamine; C34H46Cl4N10Ni2O2 In tetrahydrofuran at 20℃; for 1h; Solvent; Concentration; Inert atmosphere; Schlenk technique;	72 %Chromat.

hexanoic acid (142-62-1) → decane (124-18-5) + 1-penten (109-67-1) + pentane (109-66-0) + 2-pentene (109-68-2)

Conditions	Yield
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%

1-Decene (872-05-9) → decane (124-18-5) + decan-2-ol (1120-06-5) + Decan-2-one (693-54-9)

Conditions	Yield
With oxygen; isopropyl alcohol; bis(trifluoroacetylacetonato)cobalt(II) at 75℃; for 15h;	A 2% B 81% C 13%
With oxygen; isopropyl alcohol; bis(trifluoroacetylacetonato)cobalt(II) at 75℃; for 15h; Product distribution; comparison of yields for oxidation-reduction hydration, catalyzed by variuos Co(II)complexes;	A 2% B 81% C 13%
With oxygen; isopropyl alcohol; bis(dibenzoylmethanato)cobalt(II) at 75℃; for 2h;	A 32% B 52% C 12%
With oxygen; cobalt acetylacetonate In isopropyl alcohol at 75℃; for 1h;	A 22 % Chromat. B 45 % Chromat. C 7 % Chromat.
With oxygen; cobalt acetylacetonate In isopropyl alcohol at 75℃; for 1h; Product distribution;	A 22 % Chromat. B 45 % Chromat. C 7 % Chromat.

1-Decanol (112-30-1) → decane (124-18-5)

Conditions	Yield
With chloro-trimethyl-silane; acetic acid; sodium iodide; zinc In acetonitrile Product distribution; 1.) 30 - 35 deg C, 1.0 h; 2.) 75 - 85 deg C, 6.0 h; various alcohols;	80%
With hydrogen; vanadium(V) oxide; iron at 326.9℃; 1.5E5 Pa; Yield given;
With tetraethylammonium bromide; triphenylphosphine In acetonitrile constant current electrolysis, 25 mA;	94 % Chromat.

p,p'-dicofol + decane (124-18-5) + Dicofol (115-32-2) + dimethyl sulfoxide (67-68-5) → p,p'-DDT (50-29-3)

Conditions	Yield
In water; chlorobenzene	93.3%
In water; chlorobenzene	92.1%

Tri-n-octylamine (1116-76-3) + 2-tert-butyl-5-bromo-5-methyl-1,3-dioxolan-4-one + decane (124-18-5) → 2-(1,1-dimethylethyl)-5-methylene-1,3-dioxolan-4-one (163921-31-1)

Conditions	Yield
In cyclohexane	93%

Upstream product

• 74-96-4 ethyl bromide 
• 2875-36-7 octyl sodium 
• 111-24-0 1,5-dibromo-pentane 
• 628-76-2 1,5-dichloropentane 
• 16355-92-3 1,10-diiododecane 
• 334-48-5 1-decanoic acid 
• 2400-59-1 dihexanoyl peroxide 
• 764-93-2 1-decyne 
• 763-29-1 2-Methyl-1-pentene 
• 13002-08-9 1,1-dipentyloxyethane 
• 41780-50-1 decanal tosylhydrazone 
• 1726-66-5 tri-decylaluminum 
• 74-86-2 acetylene 
• 543-59-9 1-Chloropentane 

Downstream Products

• 100-42-5 styrene 
• 91-20-3 naphthalene 
• 447-53-0 1,2-Dihydronaphthalene 
• 2177-47-1 2-Methylindene 
• 767-60-2 3-Methylindene 
• 95-13-6 1-indene 
• 71-43-2 benzene 
• 98-83-9 isopropenylbenzene 
• 112-95-8 icosane 
• 62369-67-9 n-eicosane-d₄₂ 
• 124-11-8 non-1-ene 
• 998-62-9 2-butyl-heptanal 
• 19009-56-4 2-methyldecanal 
• 112-44-7 undecylaldehyde 

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(Matrix presented) A cheap and efficient iodination of hydrocarbons can be achieved by generating tert-butyl hypoiodite from iodine and sodium tert-butoxide. The alkane is reactant and solvent, and this metal-free process provides a clean solution for their direct iodination.

Fischer-Tropsch synthesis: effect of ammonia on product selectivities for a Pt promoted Co/alumina catalyst

The effects of co-fed ammonia in synthesis gas on the activity and product selectivities of a typical cobalt catalyst (0.5% Pt-25% Co/Al2O3) were investigated during the Fischer-Tropsch synthesis using a continuously stirred tank reactor (CSTR). The product selectivities were compared at a similar CO conversion level for various concentrations (10-1000 ppmv) of ammonia, as well as clean (un-poisoned) conditions. The addition of 10-1000 ppmv ammonia (concentration of ammonia with respect to the syngas feed) significantly decreased activity; the percentage of deactivation was similar (～40%) for the various concentrations of ammonia used. At similar CO conversions, the addition of ammonia caused an increase in olefin selectivity and the corresponding paraffin and alcohol selectivities were decreased compared to the ammonia free synthesis conditions. Olefin selectivity increased with increasing concentration of ammonia, and the paraffin and alcohol selectivities were decreased with increasing ammonia concentration. At similar CO conversions, ammonia addition exhibited a positive effect on hydrocarbon selectivity (i.e., lower light gas products and higher C5+) and also light gas product selectivities (C1-C4) were decreased and C5+ selectivity increased with increasing concentration of ammonia compared to ammonia free conditions.

Mechanistic studies of ethylene and α-olefin co-oligomerization catalyzed by chromium-PNP complexes

To explore the possibility of producing a narrow distribution of mid- to long-chain hydrocarbons from ethylene as a chemical feedstock, co-oligomerization of ethylene and linear α-olefins (LAOs) was investigated, using a previously reported chromium complex, [CrCl 3(PNPOMe)] (1, where PNPOMe = N,N-bis(bis(o-methoxyphenyl)phosphino)methylamine). Activation of 1 by treatment with modified methylaluminoxane (MMAO) in the presence of ethylene and 1-hexene afforded mostly C6 and C10 alkene products. The identities of the C10 isomers, assigned by detailed gas chromatographic and mass spectrometric analyses, strongly support a mechanism that involves five- and seven-membered metallacyclic intermediates comprised of ethylene and LAO units. Using 1-heptene as a mechanistic probe, it was established that 1-hexene formation from ethylene is competitive with formation of ethylene/LAO cotrimers and that cotrimers derived from one ethylene and two LAO molecules are also generated. Complex 1/MMAO is also capable of converting 1-hexene to C12 dimers and C18 trimers, albeit with poor efficiency. The mechanistic implications of these studies are discussed and compared to previous reports of olefin cotrimerization.

Bioinspired Hollow Nanoreactor: Catalysts that Carry Gaseous Hydrogen for Enhanced Gas-Liquid-Solid Three-Phase Hydrogenation Reactions

For conventional gas-liquid-solid three-phase heterogeneous hydrogenation reactions, hydrogen must be dissolved into the solvent to be a participating reactant, restricting the reaction rates. In this study, we demonstrate that gaseous hydrogen could be directly involved in gas-liquid-solid hydrogenation reactions through a bioinspired hollow nanoreactor with superaerophilic surface to enhance the reaction rates. We produce Pd@meso-SiO2 hollow nanoreactor, whose external surface is modified with perfluorodecyltriethoxysilane (PFDTS). In aqueous solutions, H2 gas could be spread quickly on the surface and stored in the cavity of hollow spheres, and participated in hydrogenation reactions, thereby enhancing H2 concentration around Pd nanoparticles. In hydrogenation of olefin reactions, such three-phase interface allows rapid and direct transportation of H2 bubbles to the surface of Pd nanoparticles rather than through diffusion of dissolved H2 in liquid phase, leading to an enhanced catalytic rate. This strategy is expected to be useful for designing and developing new catalytic systems of gas-liquid-solid three-phase reaction.