540-84-1

Usage

Uses

Used in Analytical Chemistry:
2,2,4-Trimethylpentane is used as a mobile phase in High Performance Liquid Chromatography (HPLC) and Liquid Chromatography coupled with Mass Spectrometry (LC-MS) for various analytical purposes.
Used in Petroleum Industry:
Isooctane is used as the standard in determining the octane numbers of fuels, with its antiknock octane number being 100. It helps rate the antiknock quality of gasoline, which is related to engine performance.
Used in Chemical Analysis:
2,2,4-Trimethylpentane serves as a solvent in chemical analysis and is also utilized in spectrophotometric analysis.
Used in the Environment:
It is released to the environment by the petroleum industries, automotive exhausts and emissions, hazardous-waste sites, landfills, and emissions from wood combustion.

Production Methods

Isooctane is produced from the fractional distillation of petroleum fractions and naphthas. It is also produced from the alkylation of 2-methylpropene with isobutane.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Saturated aliphatic hydrocarbons, such as 2,2,4-Trimethylpentane, may be incompatible with strong oxidizing agents like nitric acid. Charring of the hydrocarbon may occur followed by ignition of unreacted hydrocarbon and other nearby combustibles. In other settings, aliphatic saturated hydrocarbons are mostly unreactive. They are not affected by aqueous solutions of acids, alkalis, most oxidizing agents, and most reducing agents.

Hazard

Intermediate, azeotropic distillation entrainer.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Health Hazard

The acute toxicity of isooctane is very lowand is similar to n-octane. Exposure tohigh concentrations may produce irritationof respiratory tract. Exposure to 30,000 ppmfor an hour may be lethal to mice. There isno report of any other adverse effects fromexposure to isooctane.

Fire Hazard

Highly flammable liquid; flash point (closed cup) －12.2°C (10°F); autoignition temperature 418°C (784°F) (NFPA 1997); fireextinguishing agent: dry chemical, foam, or CO2; use a water spray to keep fire-exposed containers cool. Isooctane forms explosive mixtures with air within the range 1–4.6% by volume of air.

Flammability and Explosibility

Flammable

Safety Profile

Mutation data reported. High concentrations can cause narcosis. A very dangerous fire hazard when exposed to heat, flame, oxidmers. Can react vigorously with reducing materials. Explosive in the form of vapor when exposed to heat or flame. To fight fire, use CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALKANES.

Potential Exposure

Octane is used as a solvent; as a fuel; as an intermediate in organic synthesis; and in azeotropicdistillations.

Carcinogenicity

Male and female rats were initiated with 170 ppm N-ethyl-N-hydroxyethylnitrosamine for 2 weeks and subsequently exposed to isooctane for 61 weeks. An increase in atypical cell foci (a preneoplastic lesion) was observed in male but not female rats promoted with the high dose.

Source

Schauer et al. (1999) reported 2,2,4-trimethylpentane in a diesel-powered medium-duty truck exhaust at an emission rate of 1,240 μg/km. 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 2,2,4-trimethylpentane in the headspace were 2.7 wt % for regular grade, 2.8 wt % for mid-grade, and 3.3 wt % for premium grade. California Phase II reformulated gasoline contained 2,2,4-trimethylpentane at a concentration of 34.6 g/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 8.20 and 1,080 mg/km, respectively (Schauer et al., 2002).

Environmental fate

Surface Water. Mackay and Wolkoff (1973) estimated an evaporation half-life of 4.1 sec from a surface water body that is 25 °C and 1 m deep. Photolytic. The following rate constants were reported for the reaction of 2,2,4-trimethylpentane and OH radicals in the atmosphere: 2.3 x 10-12 cm3/molecule?sec at 300 K (Hendry and Kenley, 1979); 2.83 x 10-12 cm3/molecule?sec at 298 K (Greiner, 1970); 3.73 x 10-12 cm3/molecule?sec at 298–305 K (Darnall et al., 1978); 3.7 x 10-12 cm3/molecule?sec (Atkinson et al., 1979); 3.90 x 10-12 cm3/molecule?sec at 298 K (Atkinson, 1985). Based on a photooxidation rate constant of 3.68 x 10-12 cm3/molecule?sec for the reaction of 2,2,4-trimethylpentane and OH radicals in summer sunlight, the lifetime is 16 h (Altshuller, 1991). Products identified from the reaction of 2,2,4-trimethylpentane with OH radicals in the presence of nitric oxide included acetone, 2-methypropanal, 4-hydroxy-4-methyl-2-pentanone, and hydroxy nitrates (Tuazon et al., 2002). Chemical/Physical. Complete combustion in air produces carbon dioxide and water vapor. 2,2,4-Trimethylpentane will not hydrolyze in water.

Shipping

UN1262 Octanes, Hazard Class: 3; Labels: 3-Flammable liquid.

Purification Methods

Distil isooctane from sodium, pass it through a column of silica gel or activated alumina (to remove traces of olefins), and again distilled from sodium. Extract repeatedly with conc H2SO4, then agitate it with aqueous KMnO4, wash it with water, dry (CaSO4) and distil it. Purify it also by azeotropic distillation with EtOH, which is subsequently washed out with water, and the trimethylpentane is dried and fractionally distilled. [Forziati et al. J Res Nat Bur Stand 36 126 1946.] [Beilstein 1 IV 439.]

Incompatibilities

Reacts with strong oxidizers, causing fire and explosion hazard. Attacks some forms of plastics, rubber and coatings.

Waste Disposal

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

InChI:InChI=1/C8H18/c1-7(2)6-8(3,4)5/h7H,6H2,1-5H3

Synthetic route

tert-Octylamine (107-45-9) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
With tin hydride resin; 2,2'-azobis(isobutyronitrile) In benzene at 80℃; for 47h; deamination of other tertiary and secondary amines and dehydroxylation of secondary alcohols;	89%

2,2,4-trimethyl-4-nitro-pentane (5342-78-9) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
With 2,2-azobisbutyronitrile; tri-n-butyl-tin hydride In benzene for 2h; Heating;	75%
With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) In various solvent(s) at 80℃; for 1h; Product distribution; denitrohydrogenation of tertiary nitroalkanes with various methods;	75%

4-tetrahydrofuran-2-yl-butan-2-ol (3208-43-3, 4527-76-8) → 2-butanyltetrahydrofuran (1004-29-1) + 2-propyltetrahydropyran (3857-17-8, 113611-56-6) + octane (111-65-9) + 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
In tetrahydrofuran at 175℃; under 18751.9 Torr;	A n/a B n/a C 41% D n/a

1,1,4,4-tetrakis[bis(trimethylsilyl)metllyl]-1,4-diisopropyltetrasila-2-yne + 1,1,3,3-tetramethylbutane isonitrile (14542-93-9) → 2,4,4-trimethyl-1-pentene (107-39-1) + 2,2,4-trimethylpentane (540-84-1) + meso-1,1,4,4-tetrakis[bis(trimethylsilyl)methyl]-2,3-dicyano-l,4-diisopropyltetrasilane (1088162-71-3) + (E)-1,1,4,4-tetrakis[bis(trimethylsilyl)methyl]-2,3-dicyano-1,4-diisopropyltetrasila-2-ene (1357062-57-7) + C36H92N2Si12

Conditions	Yield
In (2)H8-toluene at 20℃; for 5h;	A 68 %Spectr. B 29 %Spectr. C 20 %Spectr. D 24% E 16 %Spectr.

trans-azocyclopropane (80201-75-8) → tetramethyl-2,2,3,3 butane (594-82-1) + 2,2,4-trimethylpentane (540-84-1) + ethane (74-84-0) + ethene (74-85-1) + cyclopropane (75-19-4) + isobutene (115-11-7)

Conditions	Yield
In various solvent(s) at 45 - 50℃; under 700 Torr; for 8h; Product distribution; Mechanism; Quantum yield; Irradiation; var. wavelengts, other solvents;	A 4.6% B 1% C 2.1% D 11% E 9.2% F 12.5%

Isobutane (75-28-5) + ethene (74-85-1) → 2,3,3-Trimethyl-pentane (560-21-4) + 2,3,4-trimethylpentane (565-75-3) + 2,2,4-trimethylpentane (540-84-1) + methylbutane (78-78-4) + 2-Methylpentane (107-83-5) + 2,3-dimethylbutane (79-29-8)

Conditions	Yield
aluminium trichloride-diethyl ether (1/1) at 30℃; under 1520 Torr; for 0.5h; Product distribution;	A n/a B 3.6% C 9.4% D 5.2% E n/a F n/a

Isobutane (75-28-5) + ethene (74-85-1) → 2,2,4-trimethylpentane (540-84-1) + methylbutane (78-78-4) + 2-Methylpentane (107-83-5) + 2,3-dimethylbutane (79-29-8)

Conditions	Yield
aluminium trichloride-diethyl ether (1/1) at 30℃; under 1520 Torr; for 0.5h; Further byproducts given;	A 9.4% B 5.2% C n/a D n/a
aluminium trichloride-diethyl ether (1/1) at 30℃; under 1520 Torr; for 0.5h; Further byproducts given. Yields of byproduct given;	A 9.4% B 5.2% C n/a D n/a
aluminium trichloride-diethyl ether (1/1) at 30℃; under 1520 Torr; for 0.5h; Further byproducts given;	A 7.9% B 3.8% C n/a D n/a

1-butylene (106-98-9) + butene-2 (107-01-7) + Isobutane (75-28-5) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
With hydrogen fluoride at 20 - 25℃;
With hydrogenchloride; aluminium trichloride at -35℃;
durch katalytische Alkylierung; als Ausgangsmaterial dienen die Butan-Buten-Fraktionen der Crackgase oder Crackbenzine;
durch katalytische Alkylierung; als Ausgangsmaterial dienen die Butan-Buten-Fraktionen der Crackgase oder Crackbenzine;
With hydrogen fluoride at 20 - 25℃;

1-butylene (106-98-9) + Isobutane (75-28-5) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
With hydrogen fluoride at 20 - 25℃;
With hydrogenchloride; aluminium trichloride at -35℃;
With hydrogen fluoride at 20 - 25℃;

2,4,4-trimethyl-1-pentene (107-39-1) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
With nickel(II) sulfide; tungsten trisulfide at 215℃; under 183877 Torr; Hydrogenation;
With methanol; copper oxide-chromium oxide barium oxide at 300℃; under 86054.4 Torr;
With platinum Hydrogenation.unter Verwendung von durch elektrische Entladungen aktiviertem Wasserstoff;

propene (187737-37-7) + Isobutane (75-28-5) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
With 2-propylfluoride; hydrogen fluoride at 40℃;

butene-2 (107-01-7) + Isobutane (75-28-5) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
With hydrogenchloride; aluminium trichloride at -35℃;
With hydrogenchloride; AlCl3 monomethanolate at 28℃;
With hydrogen fluoride at 20 - 25℃;

2,4,4-trimethylpent-2-ene (107-40-4) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
With platinum on activated charcoal Hydrogenation;
With sodium tetrahydroborate; Octanoic acid; boron trifluoride diethyl etherate 1.) triglyme, 1 h, RT; 2.) triglyme, 210 deg C, 1 h; Yield given. Multistep reaction;
With hydrogen; platinum on silica at 50 - 250℃; gas chromatograph - hydrogenation microreactor - mass spectrometer;

Isobutane (75-28-5) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
durch katalytiche Alkylierung;
With 2-propylfluoride; boron trifluoride at -80 - 25℃;
With hydrogen fluoride; cyclopropane at 40℃; under 5884.06 Torr;

methylbutane (78-78-4) + ethene (74-85-1) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
With BF3*H4O7P2

ethene (74-85-1) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
durch katalytische Polymerisation und folgende Hydrierung;

3-tert-Butyl-2,4,4-trimethyl-pent-2-ene (2437-52-7) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
Hydrogenation;

2-methyl-but-2-ene (513-35-9) + isobutene (115-11-7) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
With aluminum oxide; silica gel at 110℃; unter Druck und Hydrierung des Reaktionsprodukts an Nickel bei 100grad;

Isobutane (75-28-5) + isobutene (115-11-7) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
With hydrogen fluoride at -11℃;
With hydrogen fluoride
With sulfuric acid

isobutene (115-11-7) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
With nickel(II) oxide; iron; magnesium chloride at 250 - 300℃; under 58840.6 Torr; Hydrogenation.Reagens 4: ZnCl2;
With nickel(II) oxide; iron; magnesium chloride at 250 - 300℃; under 58840.6 Torr; Hydrogenation.Reagens 4: AlCl3;
With nickel(II) oxide; iron; magnesium chloride at 250 - 300℃; under 58840.6 Torr; Hydrogenation.Reagens 4: H3PO4-Kieselgur;
Stage #1: isobutene In water at 200℃; under 123762 Torr; Autoclave; Stage #2: With water; iron; nickel at 250℃; under 30003 Torr; for 48h; Temperature; Pressure; Autoclave;

propene (187737-37-7) + Isobutane (75-28-5) → 2,4-dimethylpentane (108-08-7) + 2,2,4-trimethylpentane (540-84-1) + 2,3-dimethyl pentane (565-59-3) + methylbutane (78-78-4) + 2-Methylpentane (107-83-5) + 2,3-dimethylbutane (79-29-8)

Conditions	Yield
With zeolite YCe at 70 - 80℃; under 7600 Torr; for 6h; Mechanism;

trans-2-Butene (624-64-6) + Isobutane (75-28-5) → 2,3,3-Trimethyl-pentane (560-21-4) + 2,2,3-trimethylpentane (564-02-3) + 2,3,4-trimethylpentane (565-75-3) + 2,2,4-trimethylpentane (540-84-1) + 2,5-dimethylhexane (592-13-2) + 2,4-dimethylhexane (589-43-5)

Conditions	Yield
With ultrastable Y zeolite with unit cell size 2.450 nm (USY-1); silica gel at 50℃; for 0.0166667h; Product distribution; other ultrastable Y zeolites (USY) with var. unit sell sizes; the effect of the strength distribution of Broensted acid sites, the concentration of reactants in the pores, and the extent of hydrogen transfer reactions;

Isobutane (75-28-5) → 2,4-dimethylpentane (108-08-7) + tetramethyl-2,2,3,3 butane (594-82-1) + 2,2,4-trimethylpentane (540-84-1) + 2,5-dimethylhexane (592-13-2) + triptane (464-06-2) + 4,4-dimethylpent-1-ene (762-62-9)

Conditions	Yield
at -78.1℃; Product distribution; Irradiation; gamma radiolysis at different irradiation doses, liquid and solid state;

3,5,5-trimethyl hexanal (5435-64-3) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
With Wilkinson's catalyst; diphenyl-phosphinic acid In tetrahydrofuran-d8 at 25℃; for 46h;	97 % Spectr.

2,2,4,4,5,5,7,7-octamethyloctane (5171-85-7) → 2,4,4-trimethyl-1-pentene (107-39-1) + 2,2,4-trimethylpentane (540-84-1) + 2,4,4-trimethylpent-2-ene (107-40-4)

Conditions	Yield
In tetralin at 279.1℃; Product distribution; Thermodynamic data; Rate constant; thermolysis, ΔG(excit.), ΔH(excit.), ΔS(excit.);

N,N'-bis(1,1,3,3-tetramethylbutyl)diazene (39198-34-0) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
In benzene at 200℃; for 0.25h;	85 % Chromat.
In benzene at 200℃; for 0.25h; Mechanism; Thermodynamic data; ΔG(excit.), ΔH(excit.), ΔS(excit.); the solvent containts 20 percent thiophenol;	85 % Chromat.

1,1,3,3-tetramethylcyclobutane (24642-79-3) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
With hydrogen; molybdenum at 191.9℃; Kinetics; Product distribution;

1,1,3,3-tetramethylcyclobutane (24642-79-3) → 2,2,4-trimethylpentane (540-84-1) + methane (34557-54-5) + ethane (74-84-0) + propane (74-98-6) + 1,1,3-trimethylcyclopentane (4516-69-2) + isobutene (115-11-7)

Conditions	Yield
With hydrogen; palladium at 201.9℃; Kinetics; Product distribution; on sintered platinum-metal films;	A 73 % Chromat. B n/a C n/a D n/a E 3 % Chromat. F n/a
With hydrogen; platinum at 173.9℃; Kinetics; Product distribution; Mechanism; on sintered platinum-metal films;	A 46 % Chromat. B n/a C n/a D n/a E 19 % Chromat. F n/a
With hydrogen; platinized copper at 281.9℃; Kinetics; Product distribution; on sintered platinum-metal films;	A n/a B n/a C n/a D n/a E 38 % Chromat. F n/a

1,1,3,3-tetramethylbutane isonitrile (14542-93-9) → 2,2,4-trimethylpentane (540-84-1)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene Heating;	85 % Chromat.
With 2,2'-azobis(isobutyronitrile); 1,1,1,2,3,3,3-heptamethyltrisilane In toluene at 348 - 363℃;	75 % Chromat.

2,3-bis(tert-butylazo)-2,3-dimethylbutane (145729-01-7) → 2,4,4-trimethyl-1-pentene (107-39-1) + 2,3-Dimethyl-2-butene (563-79-1) + tetramethyl-2,2,3,3 butane (594-82-1) + 2,2,4-trimethylpentane (540-84-1) + 2,3,3,4,4-pentamethyl-1-pentene (5846-39-9) + 2,3-dimethyl-2-(tert-butylazo)butane (145729-05-1)

Conditions	Yield
In benzene-d6 at 161℃; Rate constant; Product distribution; Kinetics; energy data: ΔH(excit.), ΔS(excit.), ΔG(excit.); var. temperatures, other solvents, also in the presence of thiophenol and irradiation;

2,2,4-trimethylpentane (540-84-1) → 2-bromo-2,4,4-trimethylpentane (62574-65-6)

Conditions	Yield
With manganese(IV) oxide; bromine at 10℃; for 1.5h;	100%
With bromine In water at 20℃; for 0.0316667h; Flow reactor; UV-irradiation;	58 %Chromat.

2-(5-amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetic acid + 2,2,4-trimethylpentane (540-84-1) + di-isopropyl ether (108-20-3) → 2-(5-amino-1,2,4-thiazol-3-yl)-2-fluoromethoxyiminoacetyl chloride. hydrochloride

Conditions	Yield
With phosphorus pentachloride In dichloromethane; water	89.6%

2,2,4-trimethylpentane (540-84-1) → hydrogen (1333-74-0)

Conditions	Yield
With air; 11 wtpercent nickel nanoparticles supported on silica at 750℃; under 760.051 Torr; for 12h; Reagent/catalyst;	84%

2,2,4-trimethylpentane (540-84-1) → 2-azido-2,4,4-trimethylpentane (35426-97-2)

Conditions	Yield
With Perbenzoic acid; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 1,1'-azobis(1-cyanocyclohexanenitrile) In 1,2-dichloro-ethane for 3h; Heating;	76%

2,2,4-trimethylpentane (540-84-1) → 2,4,4-trimethyl-2-pentanol (690-37-9)

Conditions	Yield
With chromium(VI) oxide; tetrabutylammonium periodite In dichloromethane; acetonitrile at -40℃; for 0.166667h;	68%
With (TPP)FeF; tetrabutyl ammonium fluoride; tetrabutylammonium perchlorate In dichloromethane for 1h; electrolysis: platinum-basket working eleectrode, silver wires counter electrode, 10 mA;
With dihydrogen peroxide; oxalic acid; triphenylphosphine; [Mn2(1,4,7-trimethyl-1,4,7-triazacyclononane)O3][PF6]2 In acetonitrile Product distribution; Further Variations:; Solvents;

2,2,4-trimethylpentane (540-84-1) + Benzylidenemalononitrile (2700-22-3) → C18H24N2

Conditions	Yield
With uranyl nirate hexahydrate In acetone at 20℃; for 24h; Irradiation;	68%

2,2,4-trimethylpentane (540-84-1) + α-(bromomethyl)acrylonitrile (17200-53-2) → 4,4,6,6-tetramethyl-2-methyleneheptanenitrile

Conditions	Yield
With di-tert-butyl peroxide; potassium carbonate at 130℃; for 8h; Sealed tube; Inert atmosphere;	64%

2,2,4-trimethylpentane (540-84-1) + [(3-bromoprop-1-en-2-yl)sulfonyl]benzene (110426-92-1) → [(4,4,6,6-tetramethylhept-1-en-2-yl)sulfonyl]benzene

Conditions	Yield
With di-tert-butyl peroxide; potassium carbonate at 130℃; for 8h; Sealed tube; Inert atmosphere;	57%

2,2,4-trimethylpentane (540-84-1) + benzene (71-43-2) → tert-butylbenzene (253185-03-4, 253185-04-5)

Conditions	Yield
With aluminium trichloride; tertiary butyl chloride for 4h; Product distribution; Ambient temperature;	55%

2,2,4-trimethylpentane (540-84-1) + ethyl 2-bromomethyl-2-propenoate (17435-72-2) → ethyl 4,4,6,6-tetramethyl-2-methyleneheptanoate + ethyl (Z)-2,4,4,6,6-pentamethylhept-2-enoate

Conditions	Yield
With di-tert-butyl peroxide; potassium carbonate at 130℃; for 8h; Time; Sealed tube; Inert atmosphere;	A 55% B 5%

2,2,4-trimethylpentane (540-84-1) → isobutyraldehyde (78-84-2) + acetone (67-64-1)

Conditions	Yield
With hydroxide; nitrogen(II) oxide at 24.85℃; under 740 Torr; Kinetics;	A 26% B 54%

2,2,4-trimethylpentane (540-84-1) + benzene (71-43-2) → tert-butylbenzene (253185-03-4, 253185-04-5) + 1,4-di-tert-butylbenzene (1012-72-2) + 1,3-di-tert-butylbenzene (1014-60-4)

Conditions	Yield
trifluorormethanesulfonic acid; antimony pentafluoride at 23℃; for 2h; Product distribution; ultra sound; effect of use of var. cat., var. temp., and var. times;	A 49% B n/a C n/a

2,2,4-trimethylpentane (540-84-1) + benzoyl azide (582-61-6) → N-(2,4,4-trimethylpentyl)benzamide + C15H23NO

Conditions	Yield
With [IPr2*NN]Cu(η2-C6H6) In fluorobenzene at 20℃; Inert atmosphere; Glovebox; Sealed tube;	A 49% B n/a

2,2,4-trimethylpentane (540-84-1) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(2,4,4-trimethylpentyl)-1,3,2-dioxaborolane (1643393-54-7)

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin; potassium tert-butylate at 110℃; for 20h; Reagent/catalyst; Glovebox; Inert atmosphere; Sealed tube;	42%

2,2,4-trimethylpentane (540-84-1) + acetic anhydride (108-24-7) → 2,4,4-Trimethyl-3-nitro-2-pentanol nitrate (233765-95-2) + 2,4,4-Trimethyl-3-nitro-2-pentanol acetate

Conditions	Yield
With nitric acid at 14 - 16℃; for 2h; Oxidation;	A 40% B 20%

2,2,4-trimethylpentane (540-84-1) + 3-bromo-2-phenylprop-1-ene (3360-54-1) → (4,4,6,6-tetramethylhept-1-en-2-yl)benzene

Conditions	Yield
With di-tert-butyl peroxide; potassium carbonate at 130℃; for 8h; Sealed tube; Inert atmosphere;	37%

2,2,4-trimethylpentane (540-84-1) → 1-chloro-2,2,4-trimethyl pentane (2371-06-4)

Conditions	Yield
With sulfuryl dichloride; (5,10,15,20-tetrakis(p-methoxyphenyl)-21H,23H-porphyrinate)cobalt(II) In benzene at 85℃;	20%

2,2,4-trimethylpentane (540-84-1) + 4-(1,1-dimethylethyl)benzoic acid (98-73-7) → C19H30O2

Conditions	Yield
With pentanonitrile; Selectfluor; copper(ll) bromide In nitromethane at 60℃; for 4h; Inert atmosphere;	17%

biphenyl (92-52-4) + 2,2,4-trimethylpentane (540-84-1) → 4-tert-butylbiphenyl (1625-92-9)

Conditions	Yield
With hydrogenchloride; aluminium trichloride
With hydrogenchloride; aluminium trichloride

2,2,4-trimethylpentane (540-84-1) + 4-heptanone (123-19-3) → ethene (74-85-1) + 2-Pentanone (107-87-9)

Conditions	Yield
at 25℃; erfolgt die Rekombination der Radikale.Photolysis;

Upstream product

• 106-98-9 1-butylene 
• 107-01-7 butene-2 
• 75-28-5 Isobutane 
• 107-39-1 2,4,4-trimethyl-1-pentene 
• 187737-37-7 propene 
• 107-40-4 2,4,4-trimethylpent-2-ene 
• 78-78-4 methylbutane 
• 74-85-1 ethene 
• 115-11-7 isobutene 
• 5342-78-9 2,2,4-trimethyl-4-nitro-pentane 
• 624-64-6 trans-2-Butene 
• 107-45-9 tert-Octylamine 
• 5435-64-3 3,5,5-trimethyl hexanal 
• 5171-85-7 2,2,4,4,5,5,7,7-octamethyloctane 

Downstream Products

• 1625-92-9 4-tert-butylbiphenyl 
• 74-85-1 ethene 
• 107-87-9 2-Pentanone 
• 74-98-6 propane 
• 123-72-8 butyraldehyde 
• 625-29-6 2-methyl-1-chlorobutane 
• 109-68-2 2-pentene 
• 592-41-6 1-hexene 
• 100705-11-1 2-butyl-1-methyl-cyclobutanol 
• 67-64-1 acetone 
• 1839-63-0 1,3,5-trimethylcyclohexane 
• 79042-54-9 1,2,3,4-tetramethylcyclopentane 
• 3726-36-1 1,2,3,5-tetramethyl-cyclohexane 
• 1520-42-9 1,1,2-triphenylethane 

Relevant academic research and scientific papers

Isobutane/2-Butene Alkylation on Ultrastable Y Zeolites: Influence of Zeolite Unite Cell Size

The alkylation reaction of isobutane with trans-2-butene has been carried out on a series of steam-dealuminated Y zeolites with unit cell sizes ranging from 2.450 to 2.426 nm.A fixed-bed reactor connected to an automatized multiloop sampling system allowed us to make differential product analysis from very short (1 min or less) to longer times on stream.A maximum in the initial 2-butene conversion was found on samples with unit cell sizes between 2.435 and 2.450 nm.However, the TMP/DMH ratio, i.e., the alkylation-to-oligomerization ratio, continuously increased withzeolite unit cell size.The concentration of reactants in the pores, the strength distribution of Broensted acid sites, and the extent of hydrogen transfer reactions, which in turn depend on the framework Si/Al ratio of a given zeolite, were seen to affect activity and product distribution of the catalysts.Finally, the influence of these factors on the aging characteristics of the samples was also discussed.

Formation of trimethylpentanes from isobutane and 1-butene catalyzed by sulfated metal oxides

The gas-phase alkylation of 1-butene with isobutane was carried out over superacids of sulfated metal oxides, SO4/Fe2O3, SO4/Al2O3, SO4/TiO2, SO4/SnO2, and SO4/ZrO2, at 0 °C; SO4/SnO2 gave the highest yield of trimethylpentane (TMP). It was proved from relationship between the catalyst acidities and the yields of C8 paraffins that the first intermediate species was a t-butyl cation formed on the superacidic Lewis site by abstraction of H- followed by the alkylation with butenes to form TMP.

Hybrid Catalysts Based on Sulfated Zirconium Dioxide and H-beta Zeolite for Alkylation of Isobutane with Isobutylene

Physicochemical properties of new hybrid catalysts based on sulfated zirconium oxide supported by zeolite of the Beta structural type were investigated. The acid-base characteristics of the catalysts were determined by the amount of the supported component, the maximum concentration of Br?nsted acid centers (277 Μmol/g) was achieved upon deposition of 1.7 wt.% sulfated zirconium oxide. The texture characteristics of the final catalyst were determined by the starting support. Tests of the catalysts in the reaction of isobutane alkylation with isobutylene demonstrated their advantage in selectivity and stability over the classical bulk sulfated zirconium oxide. The variation of the surface acidity is correlated with the amount of the deposited sulfated zirconium dioxide and has an extremum point at around 4 wt.%. Hybrid catalysts based on H-Beta zeolite with supported sulfated zirconium dioxide are more stable and exhibited a higher selectivity with respect to C8 hydrocarbons and trimethylpentanes, compared with bulk sulfated zirconium dioxide.

Identification of acidic species in chloroaluminate ionic liquid catalysts

Chloroaluminate ionic liquids (ILs), especially composite ionic liquids (CILs) which are ILs modified with copper(I) chloride, are highly active and selective catalysts for the alkylation of 2-butene with isobutane. The Lewis and Bronsted acidic species of these ILs were investigated by NMR spectroscopy. Pyridine is found to be a suitable indicator. Lewis acidity arises mainly from Al2Cl7- having a chemical shift at 102 ppm in the 27Al NMR spectrum, while Bronsted acidity arises from Al2Cl6OH- (chemical shift at 97 ppm). The peak at 94 ppm in the 27Al NMR spectrum is related to Al2Cl5O-. These new insights have improved our understanding of the structure of the active species in chloroaluminate ionic liquid alkylation catalysts.

In Situ Formation of Al(Fe)/Cl Metal Chloride Complexes and Evaluation of Their Catalytic Properties in the Reaction of Ethylene Oligomerization

The reactivity of the Al/Fe alloy with respect to organochlorine compounds for producing in situ catalytic (Fe-, Al/Cl) complexes from the systems Al/Fe/ tert-butyl chloride (TBC) and Al/Fe/TBC in n-hexane was investigated, together with their catalytic p

MxOy/SO42--/dealuminated zeolite β (M=Ti, Fe) as novel catalysts for alkylation of isobutane with 1-butene

A new kind of MxOy/SO42--/H-form dealuminated β (DHβ) catalysts prepared here were applied to alkylation of isobutane with 1-butene. The group of MxCy/SO42-/DHβ (M = Ti, Fe) catalysts has a lower rate of deactivation and higher selectivity of this alkylation than other group of Hβ and DHβ. It is proposed that the strong acid sites corresponding to the active sites for this alkylation can be formed by the interaction among DHβ, MxOy, and SO42-.

Stages of aging and deactivation of zeolite LaX in isobutane/2-butene alkylation

The formation of carbonaceous deposits and their effect on aging and deactivation of zeolite LaX during isobutane/2-butene alkylation at 348 K were investigated by stopping the reaction at different times on stream. Four stages of the reaction were identified: (1) stable alkylation, (2) deposit transformation, (3) slow deactivation, and (4) rapid deactivation. Deposits consist mostly of bicyclic compounds and branched carbenium ions, which are formed already at the beginning of the reaction and block Bronsted acid sites. During the deposit transformation, migration of smaller entities toward the pore mouth occurs. These cyclic compounds are further alkylated and lead to pore mouth plugging. In the final stage of rapid deactivation, the catalyst stops producing alkylate, and butene oligomerization is the main reaction leading to olefin desorption and massive deposit formation at the outside of the zeolite particles.

Ionic liquid-catalyzed alkylation of isobutane with 2-butene

A detailed study of the alkylation of isobutane with 2-butene in ionic liquid media has been conducted using 1-alkyl-3-methylimidazolium halides-aluminum chloride encompassing various alkyl groups (butyl-, hexyl-, and octyl-) and halides (Cl, Br, and I) on its cations and anions, respectively. The emphasis has been to delineate the role of both cations and anions in this reaction. The ionic liquids bearing a larger alkyl group on their cation ([C8mim]) displayed relatively higher activity than a smaller one ([C6 or C4mim]) with the same anionic composition, due to the high solubility of reactants in the former. Among the ionic liquids with different halide groups, bromides ([C8mim]Br-AlCl3) showed outstanding activity, because of the higher inherent acidity relative to others. From the 27Al NMR study, a major peak at ～99.5 ppm corresponding to [AlCl3Br]- (～99.5 ppm) was observed. Moreover, the anion showed a strong acidity based on FT-IR characterization; the largest peak related to acidity (1570 cm-1) was detected. Under various composition conditions, catalytic activity and amount of TMPs increased with concentration of anion. This is mainly attributed to a higher amount of strong acid ions [Al2Cl6Br]- which can react with hydrogen atoms at the 2-position of an imidazolium ion to form Bronsted acid. However, the ionic liquid with strong acidity (X=0.58) deactivated rapidly due to a higher sensitivity to moisture, causing decomposition. Under various reaction temperature conditions, optimum catalytic activity was observed at 80°C. The result is also attributed to the effect of anion composition. The strong acidic anion increased with temperature. However, at higher reaction temperatures (120°C), the ionic liquid showed a lower activity and TMP selectivity, since the solubility and Bronsted acid sites were reduced by decomposition of imidazolium ions. The selected ionic liquid sample ([C8mim]Br-AlCl3) was compared with one of the standard commercial catalysts, sulfuric acid. Under optimum experimental conditions, it was observed that both catalysts showed comparable catalytic behavior. However, ionic liquid showed higher activity, and lower TMP selectivity due to a more acidic nature and a lower amount of Bronsted acid sites, respectively.

A Polymer-Supported Organotin Hydride and Its Multipurpose Application in Radical Organic Synthesis

The multipurpose application of a polystyrene-supported, regenerable organotin hydride for radical organic syntheses is demonstrated using 10 examples taken from dehalogenation of bulky or multifunctional halides, dehydroxylation of secondary alcohols, and deamination of secondary or tertiary amines.

HYDROTHERMAL PRODUCTION OF ALKANES

Synthesizing an alkane includes heating a mixture including an alkene and water at or above the water vapor saturation pressure in the presence of a catalyst and one or both of hydrogen and a reductant, thereby hydrogenating the alkene to yield an alkane and water, and separating the alkane from the water to yield the alkane. The reductant includes a first metal and the catalyst includes a second metal.