106-97-8

Basic information

• Product Name: N-BUTANE
• Synonyms: A-17;Bu-Gas;butane(liquefiedgas);butane(non-specificname);Butanen;Butani;butylhydride;Freon 600
• CAS NO: 106-97-8
• Molecular Formula: C₄H₁₀
• Molecular Weight: 58.12
• EINECS: 203-448-7
• Product Categories: refrigerants;Organics;Gas Cylinders;Hydrocarbons (Low Boiling point);Synthetic Organic Chemistry;Chemical Synthesis;Compressed and Liquefied Gases;Synthetic Reagents
• Mol File: 106-97-8.mol
• Article Data: 694

Chemical Properties

• Melting Point: −138 °C(lit.)
• Boiling Point: −0.5 °C(lit.)
• Flash Point: 45
• Appearance: /gas
• Density: 0.579 g/mL at 20 °C(lit.)
• Vapor Density: 2.11 (vs air)
• Vapor Pressure: 1920mmHg at 25°C
• Refractive Index: 1.3326
• Water Solubility: 73.24mg/L(25 oC)
• Stability: Stable. Extremely flammable. Readily forms explosive mixtures with air. Note low flash point. Incompatible with strong oxidizing
• Merck: 1515
• BRN: 969129
• CAS DataBase Reference: N-BUTANE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BUTANE(106-97-8)
• EPA Substance Registry System: N-BUTANE(106-97-8)

Safety Data

• Hazard Codes: F+,F,T
• Statements: 12-46-45
• Safety Statements: 9-16-45-53
• RIDADR: UN 2037 2.1
• RTECS: EJ4200000
• F: 4.5-31
• HazardClass: 2.1
• Hazardous Substances Data: 106-97-8(Hazardous Substances Data)

Usage

Overview

N-Butane [C4H10] is a colorless gas with a faint petroleum-like odor. The main sources of butane are the refinery of crude oil and the processing of natural gas. It is commonly blended into motor vehicle gasoline to increase the fuel’s volatility and to make engine starting easier. Butane contains mixtures of methane, ethane, propane, isobutane, and n-butane and is a colourless aliphatic hydrocarbon gas with a gasoline-like odour. Butane is a component of liquefied petroleum gas (LPG) and as such is used in a wide variety of fuel applications for both recreational and leisure use, including heating and air conditioning, refrigeration, cooking, and lighters. Butane is commonly used alone or in mixtures as a propellant in aerosol consumer products, such as hairsprays, deodorants and antiperspirants, shaving creams, edible oil and dairy products, cleaners, pesticides, and coatings (e.g. automobile or household spray paint). Butane is used as a chemical intermediate in the production of maleic anhydride, ethylene, methyl tert-butyl ether (MTBE), synthetic rubber, and acetic acid and its by-products. Butane is a simple asphyxiant with explosive and flammable potential. It is also a widely used substance of abuse. The main target organs are in the CNS and cardiovascular system. Improper use and handling cause poisoning. Exposure to high levels of butane vapors can result in asphyxia. The symptoms of butane poisoning include but not limited to, rapid breathing and pulse rate, headache, dizziness, visual disturbances, mental confusion, incoordination, mood changes, muscular weakness, tremors, cyanosis, narcosis and numbness of the extremities, and unconsciousness leading to central nervous system injury. Figure 1 Chemical structure of n-butane.

Production

Butane is extremely abundant in many parts of the world, being relatively inexpensive to produce and mine. It is a fossil fuel, which has been created over the course of millions of years by a complex process deep inside the earth from the remains of plants, animals, and numerous microorganisms[4]. Different types of machinery that require butane to operate seemed quite magical when they were developed long ago, but there really is little magic involved in butane production. Its production demands human ingenuity, hard work, repeatable production processes, and following safety procedures every step of the way[4]. General its production includes the following steps: removal of oil and condensate; remove the water; glycol dehydration.

Applications

n-Butane can be used in the production of ethylene and 1,3-butadiene. It can also be used as a chemical feedstock for special chemicals in the solvent, rubber, and plastics industries, in the blending of gasoline or motor fuel, as a constituent in liquefied petroleum gas [LPG], and as an extraction solvent in deasphalting processes[5, 6]. N-Butane can be used for the manufacture of ethylene and butadiene, a key ingredient of synthetic rubber[7]. N-butane [R600] is a kind of ozone depletion neutral refrigerant, being a potential refrigerant for household appliances. N-butane has a slightly higher Ranking COP level compared to isobutane and a much higher COP than R134a of which the latter is still used in household appliances around the world[8].

Warning and Risk

Inhaling of butane can cause various central nerve system effects including drowsiness, narcosis, asphyxia, headache, cardiac arrhythmia and frostbite, which can result in instant death from Asphyxiation, Acute toxicity and ventricular fibrillation. Skin and eyes contact may cause burn or frostbite[9, 10]. Butane is the most commonly misused volatile solvent in the UK, and was the cause of 52% of solvent related deaths in 2000[9].

References

http://www.thermopedia.com/content/607/ https://pubchem.ncbi.nlm.nih.gov/compound/butane#section=Top https://www.tceq.texas.gov/assets/public/implementation/tox/dsd/final/butanes.pdf https://butanesource.com/blog/79-how-butane-is-made https://www.tceq.texas.gov/assets/public/implementation/tox/dsd/final/butanes.pdf https://www.boconline.co.uk/en/products-and-supply/speciality-gas/pure-gases/n-butane/n-butane.html https://w3.siemens.com/mcms/sensor-systems/CaseStudies/CS_Butyl_Rubber_2013-01_en_Web.pdf https://docs.lib.purdue.edu/cgi/viewcontent.cgi?article=2791&context=icec http://bennettgroup.ca/SDS/data/Gas%20Products/Butane%20-%20w221.pdf https://www.worldofmolecules.com/fuels/butane.htm

Description

Different sources of media describe the Description of 106-97-8 differently. You can refer to the following data:
1. Butane Residual Solvent Standard (Item No. 25932) is a certified reference material standard for butane, a solvent that has been used in the extraction of cannabinoids from Cannabis and has been identified as a contaminant in butane hash oil and Δ9-THC concentrates. It is designed for use as a reference standard for butane by GC- or LC-MS. This product is intended for research and forensic applications.
2. Butane is a flammable, colorless gas that follows propane in the alkane series. Butane is also called n-butane, with the “n” designating it as normal butane, the straight chain isomer. Butane’s other isomer is isobutane. The chemical name of isobutane is 2-methylpropane. Isomers are different compounds that have the same molecular formula. Normal butane and isobutane are two different compounds, and the name butane is used collectively to denote both n-butane and isobutane; the names n-butane and isobutane are used to distinguish properties and chemical characteristics unique to each compound. Butane, along with propane, is a major component of liquefied petroleum gas . It exists as a liquid under moderate pressure or below 0℃ at atmospheric pressure, which makes it ideal for storage and transportation in liquid form.

Chemical Properties

The main sources of butane are crude oil refi ning and natural gas processing. It is usually blended into motor vehicle gasoline to increase the fuel’s volatility and to make engine starting easier. Butane contains mixtures of methane, ethane, propane, iso-butane, and n-butane and is a colorless aliphatic hydrocarbon gas with a gasoline-like odor. Butane is a component of liquefi ed petroleum gas (LPG) and as such is used in a wide variety of fuel applications for both recreational and leisure use, including heating and air-conditioning, refrigeration, cooking, and in lighters. Butane is commonly used alone or in mixtures as a propellant in aerosol consumer products, such as hair sprays, deodorants and antiperspirants, shaving creams, edible oil and dairy products, cleaners, pesticides and coatings (e.g., automobile or household spray paint). Butane is used as a chemical intermediate in the production of maleic anhydride, ethylene, methyl tert-butyl ether (MTBE), synthetic rubber, and acetic acid and its by-products. Butane is a simple asphyxiant with explosive and flammable potential. It is also widely used as a substance of abuse. The main target organs are in the central nervous and cardio vascular systems. Butane is found in aerosols, lighter fuel and refi lls, small blow torches, and camping stoves. Pure grades of butane are used in calibrating instruments and as a food additive. It is widely available. Misuse and adulteration of butane is a common com mercial practice.

Physical properties

Colorless, flammable gas with a faint, disagreeable, natural gas or gasoline-like odor. Odor threshold concentration in air is 1,200 ppmv (Nagata and Takeuchi, 1990). Detected in water at a concentration of 6.2 mg/L (Bingham et al., 2001).

History

Butane is extracted from natural gas and is also obtained during petroleum refining. Butane can be obtained from natural gas by compression, adsorption, or absorption. All three processes were used in the early days of the LPG industry, but compression and adsorption were generally phased out during the 20th century. Most butane now is obtained from absorption and separation from oil.

Uses

Different sources of media describe the Uses of 106-97-8 differently. You can refer to the following data:
1. Butane is the common fuel used in cigarette lighters and also as an aerosol propellant, a calibration gas, a refrigerant, a fuel additive, and a chemical feedstock in the petrochemical industry.
2. n-Butane can be obtained from natural gas and from refinery hydro cracker streams. Most of the n-butane goes into fuel additive uses. The major chemical use is as a feedstock for ethylene production by cracking . The other important chemical uses for butane are in oxidation to acetic acid and in the production of maleic anhydride. In the past, butane also was the main feedstock for the production of butadiene by dehydrogenation, but it has been replaced by coproduct butadiene obtained from ethylene production. Ethylene. The largest potential chemical market for n-butane is in steam cracking to ethylene and coproducts. n-Butane is a supplemental feedstock for olefin plants and has accounted for 1-4 percent of total ethylene production for most years since 1970. It can be used at up to 10-15 percent ofthe total feed in ethane/propane crackers with no major modifications . n-Butane can also be used as a supplemental feed at as high as 20-30 percent in heavy naphtha crackers. The consumption of C4S has fluctuated considerably from year to year since 1970, depending on the relative price ofbutane and other feedstocks. The yield of ethylene is only 36-40 percent, with the other products including methane, propylene, ethane, and butadiene, acetylene, and butylenes. About 2-3 billion Ib of butane are consumed annually to produce ethylene.
3. As producer gas; raw material for motor fuels, in the manufacture of synthetic rubbers.
4. n-Butane occurs in petroleum, natural gas,and in refinery cracking products. It isused as a liquid fuel, often called liquefiedpetroleum gas, in a mixture with propane. Itis also used as a propellant for aerosols, a rawmaterial for motor fuels, in the production ofsynthetic rubber, and in organic synthesis.

Definition

A gaseous hydrocarbon,C4H10; d. 0.58 g cm–3; m.p. –138°C;b.p. 0°C. Butane is obtained frompetroleum (from refinery gas orby cracking higher hydrocarbons).The fourth member of the alkaneseries, it has a straight chain ofcarbon atoms and is isomeric with2-methylpropane (CH3CH(CH3)CH3,formerly called isobutane). It can easilybe liquefied under pressure and issupplied in cylinders for use as a fuelgas. It is also a raw material for makingbuta-1,3-diene (for synthetic rubber).

General Description

N-BUTANE is a colorless gas with a faint petroleum-like odor. For transportation N-BUTANE may be stenched. N-BUTANE is shipped as a liquefied gas under its vapor pressure. Contact with the liquid can cause frostbite. N-BUTANE is easily ignited. Its vapors are heavier than air. Any leak can be either liquid or vapor. Under prolonged exposure to fire or intense heat the containers may rupture violently and rocket. N-BUTANE is used as a fuel, an aerosol propellant, in cigarette lighters, and to make other chemicals.

Air & Water Reactions

Highly flammable.

Reactivity Profile

N-BUTANE can explode when exposed to flame or when mixed with (nickel carbonyl + oxygen). N-BUTANE can also react with oxidizers. Strong acids and alkalis should be avoided. .

Hazard

Highly flammable, dangerous fire and explosion risk. Explosive limits in air 1.9–8.5%. Narcotic in high concentration. Central nervous sys- tem impairment.

Health Hazard

Different sources of media describe the Health Hazard of 106-97-8 differently. You can refer to the following data:
1. n-Butane is a nontoxic gas. Exposure toits atmosphere can result in asphyxia. Athigh concentrations it produces narcosis.Exposure to 1% concentration in air for10 minutes may cause drowsiness. Its odoris detectable at a concentration of 5000 ppm.
2. Exposures to butane cause excitation, blurred vision, slurred speech, nausea, vomiting, coughing, sneezing, and increased salivation. With increased periods of exposure to high concentrations of butane, the signs and symptoms of toxicity become more severe. For instance, the exposed worker demonstrates confusion, perceptual distortion, hallucina tions (ecstatic or terrifying), delusions, behavioral changes, tinnitus, and ataxia. Workers exposed to larger doses of butane suffer from nystagmus, dysarthria, tachycardia, central depression of the CNS, drowsiness, coma, and sudden death. It has been reported that poisoned individuals show anoxia, vagal inhibition of the heart, respiratory depression, cardiac arrhythmias, and trauma.

Fire Hazard

EXTREMELY FLAMMABLE. Will be easily ignited by heat, sparks or flames. Will form explosive mixtures with air. Vapors from liquefied gas are initially heavier than air and spread along ground. CAUTION: Hydrogen (UN1049), Deuterium (UN1957), Hydrogen, refrigerated liquid (UN1966) and Methane (UN1971) are lighter than air and will rise. Hydrogen and Deuterium fires are difficult to detect since they burn with an invisible flame. Use an alternate method of detection (thermal camera, broom handle, etc.) Vapors may travel to source of ignition and flash back. Cylinders exposed to fire may vent and release flammable gas through pressure relief devices. Containers may explode when heated. Ruptured cylinders may rocket.

Flammability and Explosibility

Extremelyflammable

Safety Profile

Mildly toxic by inhalation. Causes drowsiness. An asphyxlant. Very dangerous fire hazard when exposed to heat, flame, or oxidizers. Highly explosive when exposed to flame, or when mixed with [Ni(CO)4 + O2]. To fight fire, stop flow of gas. When heated to decomposition it emits acrid smoke and fumes.

Source

Present in gasoline ranging from 4.31 to 5.02 vol % (quoted, Verschueren, 1983). 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 butane in the headspace were 7.4 wt % for regular grade, 6.9 wt % for mid-grade, and 6.3 wt % for premium grade. Schauer et al. (1999) reported butane in a diesel-powered medium-duty truck exhaust at an emission rate of 3,830 μg/km. Schauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle-phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission rate of butane was 25.9 mg/kg of pine burned. Emission rates of butane were not measured during the combustion of oak and eucalyptus. California Phase II reformulated gasoline contained butane at a concentration of 7,620 mg/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 1,620 and 191,000 μg/km, respectively (Schauer et al., 2002). Reported as an impurity (0.4 wt %) in 99.4 wt % trans-2-butene (Chevron Phillips, 2004).

Environmental fate

Biological. In the presence of methane, Pseudomonas methanica degraded butane to 1-butanol, methyl ethyl ether, butyric acid, and 2-butanone (Leadbetter and Foster, 1959). 2-Butanone was also reported as a degradation product of butane by the microorganism Mycobacterium smegmatis (Riser-Roberts, 1992). Butane may biodegrade in two ways. The first is the formation of butyl hydroperoxide which decomposes to 1-butanol followed by oxidation to butyric acid. The other pathway involves dehydrogenation yielding 1-butene, which may react with water forming 1- butanol (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-butanol). The alcohol may undergo a series of dehydrogenation steps forming butanal followed by oxidation forming butyric 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. Major products reported from the photooxidation of butane with nitrogen oxides under atmospheric conditions were acetaldehyde, formaldehyde, and 2-butanone. Minor products included peroxyacyl nitrates and methyl, ethyl and propyl nitrates, carbon monoxide, and carbon dioxide. Biacetyl, tert-butyl nitrate, ethanol, and acetone were reported as trace products (Altshuller, 1983; Bufalini et al., 1971). The amount of sec-butyl nitrate formed was about twice that of n-butyl nitrate. 2-Butanone was the major photooxidation product with a yield of 37% (Evmorfopoulos and Glavas, 1998). Irradiation of butane in the presence of chlorine yielded carbon monoxide, carbon dioxide, hydroperoxides, peroxyacid, and other carbonyl compounds (Hanst and Gay, 1983). Nitrous acid vapor and butane in a “smog chamber” were irradiated with UV light. Major oxidation products identified included 2-butanone, acetaldehyde, and butanal. Minor products included peroxyacetyl nitrate, methyl nitrate, and unidentified compounds (Cox et al., 1981). The rate constant for the reaction of butane and OH radicals in the atmosphere at 300 K is 1.6 x 10-12 cm3/molecule?sec (Hendry and Kenley, 1979). Based upon a photooxidation rate constant of 2.54 x 10-12 cm3/molecule?sec with OH radicals in summer daylight, the atmospheric lifetime is 54 h (Altshuller, 1991). At atmospheric pressure and 298 K, Darnall et al. (1978) reported a rate constant of 2.35–4.22 x 10-12 cm3/molecule?sec for the same reaction. A rate constant of 1.28 x 10-11 L/molecule?sec was reported for the reaction of butane with OH radicals in air at 298 K, respectively (Greiner, 1970). At 296 K, a rate constant of 6.5 x 10-17 cm3/molecule?sec was reported for the reaction of butane with NO3 (Atkinson, 1990). Chemical/Physical. Complete combustion in air produces carbon dioxide and water. Butane will not hydrolyze because it has no hydrolyzable functional group.

Solubility in organics

At 17 °C (mL/L): chloroform (25,000), ether (30,000) (Windholz et al., 1983). At 10 °C (mole fraction): acetone (0.2276), aniline (0.04886), benzene (0.5904), 2-butanone (0.3885), cyclohexane (0.6712), ethanol (0.1647), methanol (0.04457), 1-propanol (0.2346), 1-butanol (0.2817). At 25 °C (mole fraction): acetone (0.1108), aniline (0.03241), benzene (0.2851), 2- butanone (0.1824), cyclohexane (0.3962), ethanol (0.07825), methanol (0.03763), 1-propanol (0.1138), 1-butanol (0.1401) (Miyano and Hayduk, 1986). Mole fraction solubility in 1-butanol: 0.140, 0.0692, and 0.0397 at 25, 30, and 70 °C, respectively; in chlorobenzene: 0.274, 0.129, and 0.0800 at 25, 30, and 70 °C, respectively, and in octane: 0.423, 0.233, and 0.152 at 25, 30, and 70 °C, respectively (Hayduk et al., 1988). Mole fraction solubility in 1-butanol: 0.139 and 0.0725 at 25 and 70 °C, respectively; in chlorobenzene: 0.269 and 0.131 at 25 and 70 °C, respectively; and in carbon tetrachloride: 0.167 at 70 °C (Blais and Hayduk, 1983).

Purification Methods

Dry by passing over anhydrous Mg(ClO4)2 and molecular sieves type 4A. Air is removed by prolonged and frequent degassing at -107o. [Beilstein 1 IV 236.]

InChI:InChI=1/C4H10/c1-3-4-2/h3-4H2,1-2H3

Synthetic route

levulinic acid (123-76-2) → n-butane (106-97-8)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In hexane; water at 100℃; under 20686.5 Torr; for 24h; Temperature; Pressure; Solvent; Reagent/catalyst; Sealed tube;	99%

butanone (78-93-3) → n-butane (106-97-8)

Conditions	Yield
Photolysis;
With hydrogen; platinum
With Pt/γ-Al2O3; hydrogen at 160℃; Temperature; Gas phase;
With hydrogen at 100℃; under 750.075 Torr; for 3h;

buta-1,3-diene (106-99-0) → 1-butylene (106-98-9) + butene-2 (107-01-7) + n-butane (106-97-8)

Conditions	Yield
With 0.3 wt. % palladium on alumina; hydrogen at 50℃; under 760.051 Torr; Fixed-bed flow reactor;
With hydrogen; calcium oxide at 130℃; under 760.051 Torr; Reagent/catalyst; Temperature;
With hydrogen In n-heptane at 17℃; under 7500.75 Torr; Autoclave;

meso-erythritol (909878-64-4) → n-butane (106-97-8)

Conditions	Yield
With tris(triphenylphosphine)ruthenium(II) chloride; hydrogen bromide; hydrogen; tetrabutyl phosphonium bromide In dodecane at 200℃; under 30003 Torr; for 4h;	32%
With hydrogen In water at 119.84℃; under 60006 Torr; for 144h; Autoclave;

meso-erythritol (909878-64-4) → cis-1,4-anhydroerythritol (4358-64-9) + n-butane (106-97-8)

Conditions	Yield
With ruthenium (III) bromide; hydrogen bromide; hydrogen; tetra-n-butylphosphonium chloride In dodecane at 200℃; under 30003 Torr; for 4h;	A 51% B 8%

1-butylene (106-98-9) + carbon monoxide (201230-82-2) → methane (34557-54-5) + propane (74-98-6) + Isobutane (75-28-5) + n-butane (106-97-8)

Conditions	Yield
With hydrogen; dodecacarbonyltetrairidium In various solvent(s) at 175℃; under 760 Torr; Further byproducts given;	A 0.5% B 16% C 59% D 11%

propene (187737-37-7) + carbon monoxide (201230-82-2) → methane (34557-54-5) + propane (74-98-6) + Isobutane (75-28-5) + n-butane (106-97-8)

Conditions	Yield
With hydrogen; dodecacarbonyltetrairidium In various solvent(s) at 175℃; under 760 Torr; Further byproducts given;	A 1% B 17% C 56% D 11%

butanone (78-93-3) → iso-butanol (78-92-2, 15892-23-6) + n-butane (106-97-8)

Conditions	Yield
With Pt/γ-Al2O3; hydrogen at 100℃; Temperature; Gas phase;
With hydrogen at 60℃; under 750.075 Torr; for 3h;
With platinum on silica gel; hydrogen at 400℃; under 760.051 Torr;	A 19 %Chromat. B 11 %Chromat.

(phen)2Fe(CH2)4 → 1-butylene (106-98-9) + butene-2 (107-01-7) + ethane (74-84-0) + n-butane (106-97-8)

Conditions	Yield
With ethene; mercury In benzene-d6; water at -196 - 60℃; under 3040.2 Torr; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique;	A 38% B 24% C 20% D 15%

methylbutane (78-78-4) → Isobutane (75-28-5) + n-butane (106-97-8) + pentane (109-66-0)

Conditions	Yield
With tertiary butyl chloride; tributylhexylphosphonium bromohexachloroaluminate at 95℃; under 8533.17 Torr; for 4.6h; Time; Autoclave; Inert atmosphere;
With tertiary butyl chloride; tributylhexylphosphonium bromohexachloroaluminate at 95℃; under 8533.17 Torr; for 4.6h; Time; Autoclave; Inert atmosphere;
With tertiary butyl chloride; tributylhexylphosphonium bromohexachloroaluminate at 95℃; under 8533.17 Torr; for 4.6h; Time; Autoclave; Inert atmosphere;

buta-1,3-diene (106-99-0) → 1-butylene (106-98-9) + (Z)-2-Butene (590-18-1) + trans-2-Butene (624-64-6) + n-butane (106-97-8)

Conditions	Yield
With hydrogen; palladium In various solvent(s) at 40℃; under 3040 Torr; Kinetics; Product distribution; Further Variations:; Solvents; solvent-free;	A 72% B n/a C n/a D n/a
With hydrogen; palladium dichloride In N,N-dimethyl-formamide under 18751.5 Torr; for 0.383333h; Product distribution; Ambient temperature; various time;	A 50% B 2.5% C 23% D 1%
With hydrogen; LaPd3 at -38.1 - -0.1℃; Product distribution; Thermodynamic data; other catalyst; Ea;

acetic acid (64-19-7) → n-butane (106-97-8)

Conditions	Yield
With hydrogen; H-ZSM-5 (Si/Al 280) at 410℃; under 760.051 Torr;

meso-erythritol (909878-64-4) → furan (110-00-9) + butanone (78-93-3) + n-butane (106-97-8)

Conditions	Yield
With ruthenium (III) bromide; hydrogen bromide; hydrogen; tetrabutyl phosphonium bromide In dodecane at 200℃; under 30003 Torr; for 2h; Reagent/catalyst;	A 6% B 14% C 6%

iso-butanol (78-92-2, 15892-23-6) → n-butane (106-97-8)

Conditions	Yield
With sulfuric acid; hydrogen In water at 99.84℃; under 60006 Torr; for 4h;
With hydrogen at 60 - 140℃; under 750.075 Torr;
Stage #1: iso-butanol Acidic conditions; Stage #2: With hydrogen at 60℃; under 750.075 Torr;

(phen)2Fe(CH2)4 → 1-butylene (106-98-9) + cyclobutane (287-23-0) + n-butane (106-97-8)

Conditions	Yield
With isoprene In benzene-d6 at 60℃; Inert atmosphere; Glovebox; Sealed tube;	A 55% B 11% C 34%

butene-2 (107-01-7) → n-butane (106-97-8)

Conditions	Yield
With palladium on activated charcoal; hydrogen at 180℃; under 37503.8 Torr; for 2h; Temperature; Pressure; Autoclave;	99%
With pumice stone; nickel at 150 - 200℃; Hydrogenation;
With hydrogen; nickel at 180 - 200℃;
With C28H36Cl2Fe2O2P2; hydrogen In benzene-d6 at -195.16℃; under 3040.2 Torr; for 24h; Inert atmosphere;
With zeolite-acid

D-sorbitol (50-70-4) → methane (34557-54-5) + ethane (74-84-0) + propane (74-98-6) + n-butane (106-97-8) + n-pentanen-hexane

Conditions	Yield
Pt/Al2O3 In water at 264.85℃; under 43128.4 Torr;
With hydrogenchloride; Pt/Al2O3 In water at 264.85℃; under 43128.4 Torr; pH=2;

dichloromethane (75-09-2) + ethylmagnesium chloride (2386-64-3) → propene (187737-37-7) + n-butane (106-97-8) + pentane (109-66-0)

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

butan-1-ol (71-36-3) → butyraldehyde (123-72-8) + n-butane (106-97-8)

Conditions	Yield
With ZnO-CeO2 mixed oxide at 399.84℃; under 760.051 Torr; for 1h; Temperature; Inert atmosphere;

1-butylene (106-98-9) → n-butane (106-97-8)

Conditions	Yield
With palladium on activated charcoal; hydrogen at 180℃; under 37503.8 Torr; for 2h; Temperature; Pressure; Autoclave;	99%
With pumice stone; nickel at 150 - 200℃; Hydrogenation;
With hydrogen; tetrahydrofuran; samarium at 20.9℃; under 135 Torr;

buta-1,3-diene (106-99-0) → n-butane (106-97-8)

Conditions	Yield
With helium; propene; hydrogen at 225℃; under 760.051 Torr; Catalytic behavior; Reagent/catalyst; Flow reactor;	99.9%
With hydrogen; aluminum oxide; sulfided Mo at 4℃; under 30 Torr; for 0.333333h; variation of reaction temperature; the reaction time was studied;
With hydrogen; Fe-Zr alloy Kinetics;

thiophene (188290-36-0) → n-butane (106-97-8)

Conditions	Yield
With hydrogen; aluminum oxide; cobalt; molybdenum at 400℃; Rate constant; gas phase; flow circulation apparatus;
With hydrogen; oceanic polymetallic nodules at 380 - 460℃; under 60004.8 - 82506.6 Torr; Kinetics; catalytic acivity, comparison with industrial catalysts;
With hydrogen; aluminum oxide; molybdenum at 420℃; under 760 Torr; for 24h; catalytic activities; different Mo contents and reaction times; effect of O2 or CO uptake to the rate of hydrogenolysis at 60 deg C or 0 deg C;

D-sorbitol (50-70-4) → ethane (74-84-0) + propane (74-98-6) + n-butane (106-97-8) + pentane (109-66-0) + methanen-hexane

Conditions	Yield
With hydrogenchloride; Pt/Al2O3 In water at 264.85℃; under 43128.4 Torr; pH=3;

D-sorbitol (50-70-4) → ethane (74-84-0) + propane (74-98-6) + hexane (110-54-3) + n-butane (106-97-8) + n-pentanemethane

Conditions	Yield
With hydrogen; aluminum oxide; silica gel; palladium In water at 264.85℃; under 43653.5 Torr; pH=2;

ethanol (64-17-5) → diethyl ether (60-29-7) + acetaldehyde (75-07-0) + n-butane (106-97-8) + butan-1-ol (71-36-3)

Conditions	Yield
With hydrogen In water at 235℃; under 220.415 Torr; Reagent/catalyst; Guerbet Reaction; Flow reactor;

butan-1-ol (71-36-3) → n-butane (106-97-8)

Conditions	Yield
With aluminium oxide vanadium(V)-oxide catalyst at 380 - 400℃; under 29420.3 Torr; Hydrogenation;
With titanic acid at 430℃;
With hydrogen; vanadium(V) oxide; iron at 326.9℃; 1.5E5 Pa; Yield given;
With sulfuric acid; hydrogen In water at 99.84℃; under 60006 Torr; for 4h;

Butane-1,4-diol (110-63-4) → n-butane (106-97-8) + butan-1-ol (71-36-3)

Conditions	Yield
With sulfuric acid; hydrogen In water at 99.84℃; under 60006 Torr; for 4h;
With hydrogen In 1,4-dioxane at 139.84℃; under 60006 Torr; for 4h; Autoclave;

carbon monoxide (201230-82-2) → ethane (74-84-0) + propane (74-98-6) + carbon dioxide (124-38-9) + n-butane (106-97-8)

Conditions	Yield
With hydrogen at 300℃; under 7500.75 Torr; for 10h; Reagent/catalyst; Temperature;

pentane (109-66-0) → Isobutane (75-28-5) + methylbutane (78-78-4) + n-butane (106-97-8)

Conditions	Yield
phosphotungstic acid; Al2O3-F; platinum at 310℃; Product distribution; Further Variations:; Catalysts; Temperatures;	A 0.6% B 62.1% C 0.6%
With tertiary butyl chloride; C9H20N(1+)*Al2Cl7(1-) at 95℃; under 13446.2 Torr; for 4.4h; Time; Reagent/catalyst; Inert atmosphere;	A 30.79% B 21.33% C 8.72%
aluminum tri-bromide; copper dichloride at 28℃; for 2h; Yield given;

Butadiyne (460-12-8) → n-butane (106-97-8)

Conditions	Yield
With hydrogen; palladium/alumina In 1-methyl-pyrrolidin-2-one at 40℃; under 15001.5 Torr; Product distribution / selectivity;

n-butane (106-97-8) → maleic anhydride (108-31-6)

Conditions	Yield
With oxygen; vanadyl pyrophosphate at 420℃;	100%
With oxygen; vanadyl pyrophosphate at 420℃; Product distribution; other catalysts with different P/V atomic ratios and their catalityc activities investigated;	100%
With oxygen; vanadium-phosphorus oxidation catalyst at 396 - 491℃; Product distribution / selectivity; Gas phase;	77%

n-butane (106-97-8) → 2-nitrobutane (600-24-8, 116783-22-3)

Conditions	Yield
With N-hydroxyphthalimide; air; Nitrogen dioxide In various solvent(s) at 100℃; under 1520.1 Torr; for 14h;	65%
With nitric acid at 420℃; 2-nitro-butane, inactive form;
With nitric acid at 205℃;
With nitric acid at 400 - 450℃;

carbon monoxide (201230-82-2) + n-butane (106-97-8) → 2-Methylbutanoic acid (116-53-0, 600-07-7)

Conditions	Yield
With dipotassium peroxodisulfate; BF4(1-)*C24H51BCu3N3O16(1+)*2H2O; water In acetonitrile at 60℃; for 6h; Autoclave;	26.7%
With dipotassium peroxodisulfate; C26H38Cu3N4O16; water In acetonitrile at 60℃; for 6h; Reagent/catalyst; Autoclave; Green chemistry;	25.4%
With 2-pyrazylcarboxylic acid; dipotassium peroxodisulfate; ferrocene In water; acetonitrile at 60℃; under 7600.51 Torr; for 4h; Autoclave;	19%

methyl isoquinoline-3-carboxylate (27104-73-0) + n-butane (106-97-8) → methyl 1-(sec-butyl)isoquinoline-3-carboxylate

Conditions	Yield
With tris(2,2'-bipyridyl)ruthenium dichloride; 4,5,6,7-tetrafluoro-1-hydroxybenzo[d][1,2]iodaoxol-3(1H)-one In dichloromethane at 30℃; under 760.051 Torr; Minisci Aromatic Substitution; Inert atmosphere; Irradiation; chemoselective reaction;	78%

n-butane (106-97-8) → butyraldehyde (123-72-8) + butanone (78-93-3) + iso-butanol (78-92-2, 15892-23-6) + butyric acid (107-92-6) + butan-1-ol (71-36-3)

Conditions	Yield
With 2-pyrazylcarboxylic acid; ferrocene; dihydrogen peroxide; triphenylphosphine In acetonitrile at 50℃; for 4h; Autoclave; Overall yield = 58 %;
Stage #1: n-butane With 2-pyrazylcarboxylic acid; [{VO(EtO)(EtOH)}2(1κ2O,κN:2κ2O,κN-bis(2-hydroxybenzylidene)oxalohydrazonic acid)]·2H2O; dihydrogen peroxide In water; acetonitrile at 50℃; for 4h; Stage #2: With triphenylphosphine under 760.051 Torr; Autoclave; Overall yield = 45.3 %Chromat.;

(E)-1,3-diphenyl-2-propen-1-ol (62668-02-4) + n-butane (106-97-8) → (E)-butyl(1,3-diphenylallyl)sulfane

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; sodium thiosulfate In water at 80℃; for 5h; Sealed tube;	72%

n-butane (106-97-8) → buta-1,3-diene (106-99-0)

Conditions	Yield
magnesium-molybdenum	98%
With water; oxygen at 25 - 550℃; under 1800.18 - 11251.1 Torr;	95%
With water; hydrogen; oxygen at 25 - 555℃; under 1800.18 - 15001.5 Torr; Product distribution / selectivity;	95%

n-butane (106-97-8) → benzene (71-43-2)

Conditions	Yield
With carbon dioxide at 540℃; Gas phase; Flow reactor;	31%
at 850℃;
at 800 - 850℃;
With gallium nitride at 450℃; under 0.00750075 Torr;

n-butane (106-97-8) → tetrahydrofuran (109-99-9)

Conditions	Yield
Stage #1: n-butane With oxygen at 403℃; under 2175.22 Torr; Stage #2: With hydrogen In Phthalic acid dibutyl ester Product distribution / selectivity;	99.5%

n-butane (106-97-8) → Isobutane (75-28-5)

Conditions	Yield
With hydrogen at 380℃; under 2250.23 Torr; Temperature;	62%
With hydrogen; Pt-η-Al2O3-Cl at 200℃; under 15001.2 - 22501.8 Torr; Product distribution; test chlorinated catalysts for the isomerization of C4-C6 alkanes; also other alkanes (n-pentane, hexane fraction and their mixtures);	53.83%
With Ga(3+)-modified sulfated zirconia at 190℃; under 760.051 Torr; Reagent/catalyst; Flow reactor;	30%

n-butane (106-97-8) → methyl vinyl ketone (78-94-4) + butanone (78-93-3)

Conditions	Yield
With oxygen; 12percentMo1Cs1Na0.04Pr0.01On/SiO2 at 475℃; under 760.051 Torr;

n-butane (106-97-8) → butanone (78-93-3)

Conditions	Yield
With C56H52ClFeN4O(1+) at 0℃; Kinetics;	23%
With hydrogen bromide; oxygen at 180℃;
With 2-pyrazylcarboxylic acid; dihydrogen peroxide; [n-Bu4N]VO3 In acetonitrile at 75℃; under 2280 Torr; for 2.5h; Product distribution;

Upstream product

• 71-23-8 propan-1-ol 
• 10467-10-4 ethylmagnesium iodide 
• 5954-46-1 diethyl ether ; compound with bromine 
• 74-96-4 ethyl bromide 
• 109-72-8 n-butyllithium 
• 60-29-7 diethyl ether 
• 628-28-4 butyl methyl ether 
• 34557-54-5 methane 
• 287-23-0 cyclobutane 
• 4984-20-7 ethyltitanium trichloride 
• 106-99-0 buta-1,3-diene 
• 78-93-3 butanone 
• 927-80-0 1-ethoxyacetylene 
• 71-43-2 benzene 

Downstream Products

• 126-99-8 chloroprene 
• 78-93-3 butanone 
• 115-11-7 isobutene 
• 106-98-9 1-butylene 
• 74-86-2 acetylene 
• 689-97-4 3-buten-1-yne 
• 460-12-8 Butadiyne 
• 107-00-6 but-1-yne 
• 187737-37-7 propene 
• 74-85-1 ethene 
• 67-56-1 methanol 
• 71-23-8 propan-1-ol 
• 64-17-5 ethanol 
• 71-36-3 butan-1-ol 

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Quantitative determination of N-BUTANE (cas 106-97-8) metabolites in three cases of butane sniffing death08/22/2019

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Experimental and kinetic modeling investigation on pyrolysis and combustion of N-BUTANE (cas 106-97-8) and i-butane at various pressures08/20/2019

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Relevant articles and documents

Reductive dehydration of butanone to butane over Pt/γ-Al 2O3 and HZSM-5

We show that butanone can be reacted to form n-butane in an isothermal reactor containing a 1 wt.% Pt/γ-Al2O3 and an HZSM-5 catalyst (total mass of 12-400 mg, Si/Al = 11.5) below 160 C with up to 99% selectivity and 67% yield. The catalyst loading (12-400 mg) and temperature (100-250 C) were varied to obtain primary products whose selectivities decreased with conversion and secondary/tertiary products whose selectivities increased with conversion. As conversion increased, the selectivities of butanol and butene decreased, showing the formation of butane from butanone through a series reaction pathway: butanone → 2-butanol → butene → butane. Butane selectivity increased as the temperature was increased from 100 to 200 C when compared at similar conversions due to higher dehydration rates over the zeolite. Processing ketones at low temperatures over bifunctional catalysts may be an efficient means of obtaining high yields of stable paraffins from reactive oxygenates.

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Cobalt-Iron-Manganese Catalysts for the Conversion of End-of-Life-Tire-Derived Syngas into Light Terminal Olefins

Co-Fe-Mn/γ-Al2O3 Fischer–Tropsch synthesis (FTS) catalysts were synthesized, characterized and tested for CO hydrogenation, mimicking end-of-life-tire (ELT)-derived syngas. It was found that an increase of C2-C4 olefin selectivities to 49 % could be reached for 5 wt % Co, 5 wt % Fe, 2.5 wt % Mn/γ-Al2O3 with Na at ambient pressure. Furthermore, by using a 5 wt % Co, 5 wt % Fe, 2.5 wt % Mn, 1.2 wt % Na, 0.03 wt % S/γ-Al2O3 catalyst the selectivity towards the fractions of C5+ and CH4 could be reduced, whereas the selectivity towards the fraction of C4 olefins could be improved to 12.6 % at 10 bar. Moreover, the Na/S ratio influences the ratio of terminal to internal olefins observed as products, that is, a high Na loading prevents the isomerization of primary olefins, which is unwanted if 1,3-butadiene is the target product. Thus, by fine-tuning the addition of promoter elements the volume of waste streams that need to be recycled, treated or upgraded during ELT syngas processing could be reduced. The most promising catalyst (5 wt % Co, 5 wt % Fe, 2.5 wt % Mn, 1.2 wt % Na, 0.03 wt % S/γ-Al2O3) has been investigated using operando transmission X-ray microscopy (TXM) and X-ray diffraction (XRD). It was found that a cobalt-iron alloy was formed, whereas manganese remained in its oxidic phase.

Role of Ga3+promoter in the direct synthesis of iso-butanolviasyngas over a K-ZnO/ZnCr2O4catalyst

The direct synthesis of iso-butanol is an important reaction in syngas (composed of CO and H2) conversion. K-ZnO/ZnCr2O4(K-ZnCr) is a commonly used catalyst. Here, Ga3+is used as an effective promoter to boost the efficiency of the catalyst and retard the production of CO2. X-ray diffraction, X-ray photoelectron spectroscopy, ultraviolet-visible diffuse reflection spectroscopy and electron microscopy were used to characterize the structural variations with different amounts of Ga3+, the results showed that the particle size of the catalyst decreases with the addition of Ga3+. The temperature-programmed desorption of NH3and CO2, and diffuse reflectance infrared Fourier-transform spectroscopy (DRIFTs) analysis of the CO adsorption revealed that the acidity and basicity were altered owing to the different forms of Ga3+adoption. X-ray photoelectron spectroscopy and density functional theory (DFT) calculations revealed that the formation of Ga clusters that are coordinated on the exposed surfaces of ZnCr2O4, and undergo a tetra-coordinated Ga3+exchange with one of the Zn in ZnCr2O4(ZG) and ZnGa2O4, probably depends on the amount of Ga added. The structural evolution of the Ga3+promoted K-ZnO/ZnCr2O4catalysts can be described as follows: (i) the main forms are ZG and Ga coordinated ZnCr2O4, in which the amount of Ga3+is below 1.10 wt%; and (ii) the Ga3+containing compound is gradually changed from ZG to ZnGa2O4and the amount of gallium clusters increased when the amount of Ga3+was higher than 1.10 wt%. The catalytic performance evaluation results show that K-Ga1.10ZnCr exhibits the highest space time yield and selectivity of alcohols, in which the three compounds play different roles in syngas conversion: ZG is the main active site that boosts the efficiency of the catalysts, owing to the intensified CO adsorption and decreased activation energy of CHO formation through CO hydrogenation; ZnGa2O4only modifies the surface basicity and acidity on the catalyst, thereby impacting the carbon chain growth after the CO is adsorbed. The effects of Ga coordinated with ZnCr2O4shows little impact on the CO adsorption owing to the weak electron donating effects of Ga.

Enzymatic Electrosynthesis of Alkanes by Bioelectrocatalytic Decarbonylation of Fatty Aldehydes

An enzymatic electrosynthesis system was created by combining an aldehyde deformylating oxygenase (ADO) from cyanobacteria that catalyzes the decarbonylation of fatty aldehydes to alkanes and formic acid with an electrochemical interface. This system is able to produce a range of alkanes (octane to propane) from aldehydes and alcohols. The combination of this bioelectrochemical system with a hydrogenase bioanode yields a H2/heptanal enzymatic fuel cell (EFC) able to simultaneously generate electrical energy with a maximum current density of 25 μA cm?2 at 0.6 V and produce hexane with a faradaic efficiency of 24 %.

Skeletal Rearrangement of Alkanes over Ir/Al2O3. Transformation of n-Pentane, 2-Methylbutane and 2,2-Dimethylbutane

Transformation of n-pentane, 2-methylbutane and 2,2-dimethylbutane has been investigated as a function of the H2/hydrocarbon ratio over a 10 wtpercent Ir/Al2O3 catalyst of 14 percent dispersion.The selectivity of isomer formation has been observed to decrease with the increase of the H2/hydrocarbon ratio and follow the sequence n-pentane > 2-methylbutane >> 2,2-dimethylbutane.The effect of the experimental conditions on the product selectivity has been interpreted considering the actual surface state of the working catalyst.

Catalytic behavior of graphite nanofiber supported nickel particles. 3. The effect of chemical blocking on the performance of the system

Graphite nanofibers are a newly developed type of material produced by the catalytic decomposition of carbon containing gases at high temperatures. The individual components of these conformations, small-sized graphite crystallites, are arranged in such a manner that only the edge regions are exposed. The carbon atoms at these sites that are arranged in two conformations, `armchair' or `zigzag', act as templates for the nucleation of metal crystallites. Treatment of graphite with certain phosphorus compounds is a process that is known to result in preferential blocking of the `armchair' faces, whereas boron oxide selectively substitutes into the `zigzag' faces. In the current investigation pretreatment in phosphorus oxide was found to exert little or no effect on the subsequent catalytic performance of graphite nanofiber supported nickel with respect to hydrogenation of ethylene and 1-butene. In contrast, incorporation of boron into the carbonaceous support, which resulted in blockage of the `zigzag' sites of the graphite nanofibers rendered the supported metal system virtually inactive toward hydrogenation of either of the olefins. These results suggest that the active state of nickel is one where the particles are preferentially located on the `zigzag' faces of the nanofiber structures. Under these conditions the metal particles adopt a crystallographic arrangement that is favorable toward reaction with both reactant molecules. It is evident that one can control the catalytic behavior of a given metal by careful tailoring the support structure at the atomic level.

A robust platinum carbonyl cluster anion [Pt3(CO)6]52- encapsulated in an ordered mesoporous channel of FSM-16: FTIR/EXAFS/TEM characterization and catalytic performance in the hydrogenation of ethene and 1,3-butadiene

A robust trigonal prismatic cluster anion [Pt3(CO)6]52- (vCO = 2078, 1878 cm-1; ??max = 405 and 702 nm; R1(Pt - Pt) = 2.68 Aì? (CN = 2.0); R2(Pt - Pt) = 3.08 Aì? (CN = 1.5)) is selectively synthesized in the ordered hexagonal channel of FSM-16 by the reductive carbonylation of H2PtCl6TNR4+/FSM-16 under a CO + H2O atmosphere at 323 K. The Pt cluster anion extracted in THF solution by cation metathesis was identified as [Pt3(CO)6]52- by FTIR and UV - vis spectroscopic data. TEM observation showed that [Pt3(CO)6]52- was uniformly dispersed and aligned in the mesoporous channels of FSM-16. The Pt15 cluster anions formed in FSM-16 were relatively stabilized by the coimpregnated quaternary alkylammonium cations as NR4+ in the following order for the alkyl groups: butyl > ethyl > methyl, methyl viologen (MV) > hexyl a?? no countercations. The EXAFS and FTIR studies demonstrated that [Pt3(CO)6]52- in FSM-16 was transformed by the controlled removal of CO at 300-343 K into the partially decarbonylated Pt15 cluster (R1(Pt - Pt) = 2.69 Aì?, CN = 2.2; R2(Pt - Pt) = 3.10 Aì?, CN = 1.4). This sample showed IR spectra indicating a linear CO (vCO = 2062 cm-1) without a bridged one. The Pt carbonyl cluster was eventually converted by thermal evacuation exceeding 463 K to naked Pt particles (15 Aì? diameter; R(Pt - Pt) = 2.76 Aì?, CN = 7.8). The controlled removal of CO from [Pt3(CO)6-x]52- in FSM-16 by thermal evacuation at 300-423 K yields samples with marked catalaytic activities for hydrogenation of ethene and 1,3-butadiene at 300 K. 1,3-Butadiene is selectively hydrogenated to 1-butene on the partially decarbonylated Pt carbonyl clusters in FSM-16, whereas it is preferentially converted to n-butane on the naked Pt particles in FSM-16.

Selective hydrogenation of 1,3-butadiene on PdNi bimetallic catalyst: From model surfaces to supported catalysts

The selective hydrogenation of 1,3-butadiene serves as a means to purify the butene stream generated from cracking naphtha or gas oil. To identify selective hydrogenation catalysts, 1,3-butadiene was studied on single crystal Ni/Pd(1 1 1) bimetallic surfaces, utilizing density functional theory (DFT) calculations and temperature-programmed desorption (TPD). DFT calculations predicted that the Pd-terminated bimetallic surface should be more active and selective to produce 1-butene, which were verified experimentally using TPD. The promising results on model surfaces were extended to γ-Al 2O3-supported catalysts using both batch and flow reactors. Extended X-ray absorption fine structure (EXAFS) and transmission electron microscopy (TEM) confirmed the formation of bimetallic nanoparticles. The PdNi bimetallic catalyst showed higher hydrogenation activity and 1-butene selectivity than the monometallic catalysts. The excellent correlation between model surfaces and supported catalysts demonstrates the feasibility of designing effective bimetallic catalysts for selective hydrogenation reactions.

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A low temperature reaction sequence for methane conversion

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Quantitative determination of volatile products formed in electrolyses of organic compounds

A straightforward and accurate procedure has been developed for the quantitation of volatile products that are formed from electrolyses of organic compounds. This methodology, which eliminates the need for external cold traps, utilizes an internal standard that is present in both the solution and gas phases of a gas-tight electrochemical cell. By sampling the gas and solution phases of the cell at the end of an electrolysis and by using gas chromatography to determine the quantities of the various volatile products in each phase with respect to the internal standard, one can ascertain the absolute yield of each product derived from the electrolysis of the starting material. In this paper, we present the theoretical background for this technique, including the formulation and use of experimentally measured gas chromatographic response factors, and we demonstrate the applicability of the approach for the quantitation of seven volatile products that are formed by the electrolytic reduction of 1,4-dibromobutane at a reticulated vitreous carbon cathode in dimethylformamide containing tetramethylammonium perchlorate. This method can be readily adapted to any compound whose electrolysis gives rise to volatile products.

SPIROANNELATION VIA GEM-DIHALOCYCLOPROPANE SUBSTRATES AND A CYCLOCUPRATE SPECIES

The dialkylation of gem-dibromocyclopropanes with a new 'cyclocuprate' species to yield spiro compounds is possible if the reaction is performed in the presence of a lithium acetylide.

Catalytic Properties of Low-valent Lanthanide Species introduced into Y-Zeolite

Low-valent ytterbium or europium species were introduced into Y-zeolites by impregnation from ytterbium or europium metal dissolved in liquid ammonia.The zeolites thus loaded with ytterbium or europium have a high catalytic activity for the isomerization of but-1-ene at 273 K, when they were heated under vacuum at ca. 500 K.Their catalytic activities are strongly influenced by the alkali-metal cations present in the Y-zeolite.The isomerization proceeds via an allylic carbanion-type intermediate.On the other hand, the zeolites heated under vacuum around 900 K areactive for the hydrogenation of ethene at 273 K, and buta-1,3-diene at 323 K.The photoluminescence of europium supported on zeolites and temperature-programmed desorption spectra of gases desorbed from zeolites loaded with europium or ytterbium suggest that metal imides such as EuNH, and metal-like species may be formed by the zeolites under vacuum at ca. 500 and 900 K, respectively.

Bimetallic Au-Pd alloy nanoparticles supported on MIL-101(Cr) as highly efficient catalysts for selective hydrogenation of 1,3-butadiene

Gold-palladium (Au-Pd) bimetallic nanoparticle (NP) catalysts supported on MIL-101(Cr) with Au : Pd mole ratios ranging from 1 : 3 to 3 : 1 were prepared through coimpregnation and H2reduction. Au-Pd NPs were homogeneously distributed on the MIL-101(Cr) with mean particle sizes of 5.6 nm. EDS and XPS analyses showed that bimetallic Au-Pd alloys were formed in the Au(2)Pd(1)/MIL-101(Cr). The catalytic performance of the catalysts was explored in the selective 1,3-butadiene hydrogenation at 30-80 °C on a continuous fixed bed flow quartz reactor. The bimetallic Au-Pd alloy particles stabilized by MIL-101(Cr) presented improved catalytic performance. The as-synthesized bimetallic Au(2)Pd(1)/MIL-101(Cr) with 2 : 1 Au : Pd mole ratio showed the best balance between the activity and butene selectivity in the selective 1,3-butadiene hydrogenation. The Au-Pd bimetallic-supported catalysts can be reused in at least three runs. The work affords a reference on the utilization of a MOF and alloy nanoparticles to develop high-efficiency catalysts.

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Evidence for Surface Phosphinidene Intermediates Mg> in the Heterogeneous Dechlorination of Alkyldichlorophosphanes RPCl2 by Mg Metal

The heterogeneous dechlorination of alkyldichlorophosphanes by Mg metal at 600 K yields chemisorbed products which include penta-alkylcyclopentaphosphanes (RP)5, in addition to RnPH(3-n), R2P-PR2, P4, RH, and R-R, and thus provides evidence for surface phosphinidene intermediates Mg>.

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Catalytic reduction of iodoethane and 2-iodopropane at carbon electrodes coated with anodically polymerized films of nickel(II) salen

In acetonitrile containing tetramethylammonium tetrafluoroborate, nickel(II) salen undergoes anodic polymerization onto a carbon electrode. Nickel(II) in the polymer film exhibits reversible one-electron reduction to form nickel(I), which can catalytically reduce iodoethane or 2-iodopropane to form an ethyl or 2-propyl radical, respectively, and to regenerate nickel-(II). Kinetics studies with the aid of hydrodynamic voltammetry indicate that the catalytic reduction of iodoethane belongs to the ER regime of Saveant and co-workers, whereas catalytic reduction of 2-iodopropane is of the S classification. Controlled-potential electrolyses of iodoethane and 2-iodopropane at nickel-(II) salen-coated reticulated vitreous carbon cathodes give product distributions in accord with the relative importance of radical coupling and disproportionation. Direct reduction of iodoethane at a bare cathode generates products via a carbanion mechanism. Products obtained from direct reduction of 2-iodopropane depend on the potential employed; at a potential corresponding to the first voltammetric wave, product distributions are nearly identical with those obtained from the catalytic reduction, whereas at a potential after the second voltammetric wave, the products are derived from the 2-propyl carbanion.

ATP-independent substrate reduction by nitrogenase P-cluster variant

The P-cluster of nitrogenase is largely known for its function to mediate electron transfer to the active cofactor site during catalysis. Here, we show that a P-cluster variant (designated P*-cluster), which consists of paired [Fe4S4]-like clusters, can catalyze ATP-independent substrate reduction in the presence of a strong reductant, europium (II) diethylenetriaminepentaacetate [Eu(II)-DTPA]. The observation of a decrease of activity in the rank ΔnifH, ΔnifBΔnifZ, and ΔnifB MoFe protein, which corresponds to a decrease of the amount of P*-clusters in these cofactor-deficient proteins, firmly establishes P*-cluster as a catalytically active metal center in Eu(II)-DTPA-driven reactions. More excitingly, the fact that P*-cluster is not only capable of catalyzing the two-electron reduction of proton, acetylene, ethylene, and hydrazine, but also capable of reducing cyanide, carbon monoxide, and carbon dioxide to alkanes and alkenes, points to a possibility of developing biomimetic catalysts for hydrocarbon production under ambient conditions.

Selective Lanthanide-catalysed Reactions. Catalytic Properties of Sm and Yb Metal Vapour Deposition Products

The characteristics of lanthanide catalysts obtained when Sm and Yb were vaporized into a frozen organic (tetrahydrofuran, benzene and methylcyclohexane) matrix (77 K) were investigated.These low-valent, highly dispersed lanthanide particles (indicated as Sm/THF, Sm/benzene, Yb/THF, Yb/benzene etc.) were catalytically active and selective for hydrogenation and isomerization.Samarium usually showed a greater activity than ytterbium.Olefin hydrogenation obeyed the rate law v=kPH, suggesting that the reaction is controlled by catalytic activation of hydrogen.The molecular isotopic identity of hydrogen was conserved during the hydrogenation.Yb/THF and Yb/benzene were active for partial hydrogenation of benzene to cyclohexene.For the hydrogenation of olefins and acetylenes the substrate specificity was high; thus C-C double bonds were more readily reduced than triple bonds.The samarium and ytterbium catalysts discriminate between terminal and internal C-C triple bonds, only internal CC bonds (but-2-yne and pent-2-yne) being reduced very selectively in contrast to acetylene, methylacetylene and but-1-yne.Solid base character of the lanthanide provides a cause for these differences in catalytic properties.

Tuning crystal phase of molybdenum carbide catalyst to induce the different selective hydrogenation performance

α-MoC, β-Mo2C, and MoC-Mo2C were synthesized and investigated in the selective hydrogenation of 1,3-butadiene to understand the effect of crystal phases. The catalysts were characterized by XRD, N2-physisorption, SEM, TEM, XPS and chemisorptions. The adsorption properties and electronic properties over MoC(001) and Mo2C(001) were investigated by DFT calculations. The catalysts were evaluated at low and high temperatures in a fixed-bed reactor. β-Mo2C exhibits high activity and low butenes selectivity, due to the high concentration of hydrogen at each active site as well as the stronger adsorption and higher capacity of alkene; MoC-Mo2C shows better stability due to synergetic effect. At high temperature, the reaction rate is more dependent on the PH2 than PC4H6. Increasing PH2 could promote the activity and reduce oligomers formation. β-Mo2C exhibits the best performance at high temperatures concerning its high activity and the inhibition of oligomerization. This work is valuable for the non-precious metal catalyst development.

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

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).

A selective and stable Fe/TiO2catalyst for selective hydrogenation of butadiene in alkene-rich stream

The replacement of precious metals by more abundant and therefore much less expensive metals remains a very important challenge in catalysis. A Fe/TiO2catalyst prepared by deposition-precipitation with urea showed very high selectivity to alkenes (>99%), even at high conversion (>90%), in selective hydrogenation of butadiene in an excess of propene. Its activity is very stable at 175 °C whereas the catalyst deactivates at 50 °C, although it is also initially very active. The presence of metallic iron seems to be necessary to ensure these excellent performances.