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Home > Encyclopedia > 2-Methyl-2-butene

2-Methyl-2-butene

2-Methyl-2-butene structure

2-Methyl-2-butene 

structure
  • CAS No:

    513-35-9

  • Formula:

    C5H10

  • Chemical Name:

    2-Methyl-2-butene

  • Synonyms:

    2-Butene,2-methyl-;2-Methyl-2-butene;Amylene;Trimethylethylene;β-Isoamylene;3-Methyl-2-butene;1,1,2-Trimethylethylene;Trimethylethene;NSC 74118;2-Methyl-2-butylene

  • Categories:

    Organic Chemistry  >  Hydrocarbons and Derivatives

Description

2-Methyl-2-butene is a highly flammable, volatile, colorless liquid that is soluble in alcohol, ether, and benzene, but poorly soluble in water. It can be used as an intermediate in synthetic rubber, resin, and organic synthesis. The melting point of 2-Methyl-2-butene is -133.77°C, the boiling point is 38.4°C, the relative density is (20/4°C) 0.6623, the refractive index is 1.3874, the flash point is -45°C, it polymerizes when left for a long time, and has an unpleasant odor.

2-Methyl-2-butene Basic Attributes

70.13290

70.13

208-156-3

HR68LQ4T3X

74118

2460|1108

DTXSID8027165

LIQUID AT ROOM TEMPERATURE|Colorless volatile liquid

2901291000

Characteristics

0

1.97250

2-methyl-2-butene appears as a clear colorless liquid with a petroleum-like odor. Less dense than water and insoluble in water. Hence floats on water. Vapors heavier than air.

0.66 g/cm3 @ Temp: 15 °C

-133.61 °C

37.5-38.5 °C

-45ºC

1.386-1.388

Insoluble in water; soluble in ethanol, ethyl ether, benzene

Flammables area

25.7 psi ( 55 °C)

2.4 (vs air)

Disagreeable odor

8.69e-11 cm3/molecule*sec

Henry's Law constant = 0.110 atm-cu m/mole

Polymerizes on long standing|Highly flammable, dangerous fire and explosion risk|Hydroxyl radical rate constant = 8.69X10-11 cu cm/molecule-sec @ 25 °C

Highly flammable. Insoluble in water.

Hydrocarbons, Aliphatic Unsaturated

Highly Flammable

2-METHYL-2-BUTENE may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release gaseous hydrogen. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic polymerization reactions.

3.4634X10+7 J/kmol @ 139.39 K

Critical temperature: 471.00 K; critical pressure: 3.4X10+6 Pa

Safety Information

II

3

UN 1108/2460

3

R12; R22; R51/53; R65

S16-S33-S61-S9

F+; Xn; N

Stable under normal shipping and handling conditions.

P201-P210-P273-P301 + P310-P304 + P340 + P312-P331

H225-H302-H304-H315-H336-H341-H351-H411

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|Incineration: Spray into a furnace. Incineration will become easier by mixing with a more flammable solvent.

UN 1108/2460

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. Substance may be transported hot. For hybrid vehicles, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. If molten aluminum is involved, refer to ERG Guide 169. (ERG, 2016)|Flammable - 4th degree

|Danger|H224 (24.36%): Extremely flammable liquid and vapor [Danger Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P281, P301+P310, P301+P312, P302+P352, P303+P361+P353, P304+P340, P308+P313, P312, P321, P330, P331, P332+P313, P362, P370+P378, P391, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 344 companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P281, P301+P312, P303+P361+P353, P304+P340, P308+P313, P312, P330, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: CAUTION: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. CAUTION: For mixtures containing alcohol or polar solvent, alcohol-resistant foam may be more effective. SMALL FIRE: Dry chemical, CO2, water spray or regular foam. LARGE FIRE: Water spray, fog or regular foam. Do not use straight streams. Move containers from fire area if you can do it without risk. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2016)

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)

HIGHLY FLAMMABLE

TO PREVENT EXPLOSION HAZARD, MAXIMUM PERMISSIBLE OLEFIN CONCN IN AIR SHOULD NEVER EXCEED ONE-FIFTH OF THE LOWER EXPLOSIVE LIMIT. /OLEFINS/

/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. Substances may be transported hot.|/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Health: 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.|/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.|/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.|For more DOT Emergency Guidelines (Complete) data for AMYLENE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Emissions from 10 four-stroke lawn mower engines contained 0.26-0.30% amylene by mass of total organic gases(1). Amylene was detected ranging from 8.3-11.4 ppm for YJ93-6E-3 jet engines and 0.02-2.1 ppm for J856E-5B jet engines in exhausts when operated at simulated supersonic flight conditions(2). Amylene was detected in exhaust emitted from alkylate-based fuels, concn not specified(3). Amylene has been reported in stack emissions from waste incineration processes from 1964 to 1979, concn not specified(4). Automobile exhaust, representative of a vehicle operating under normal traffic conditions, was determined to contain 0.1-0.03 ppm of amylene when not irradiated(5).

SEDIMENT: Amylene was detected in sediment samples taken from Dec 1975-Jan 1976 from Walvis Bay ranging from 0.51-49.0 ng/g dry weight sediment. Greatest concn of amylene was found at a depth of 10 cm(1).

URBAN/SUBURBAN: Amylene was detected ranging from 3.7 to 11.5 ppb in ambient air samples taken around the Tulsa, OK area on July 27, 1978(1). Amylene was also detected in air samples taken from Rio Blanco County, CO ranging from 0.9-3.0 ppb on July 24, 1978 and from air samples taken from the Smokey Mountains ranging from 0.1-3.7 ppb from Sept 25-26, 1978(1). Average exhaust hydrocarbon composition emitted from gasoline fueled vehicles in Sydney, Australia contained 0.5% amylene(2). Under congested city driving conditions (large % of vehicles at idle speed), amylene was detected at 0.45% of total emissions; under urban commuter traffic(ave speed 21.1 mi/hr), amylene was detected at 0.42% of total emissions and under rush hour expressway traffic (ave speed 34.7 mi/hr), amylene was detected at 0.27% of non-methane hydrocarbon emissions along U.S. Highway 70 near Raleigh, NC(3). Amylene concn in the major Tingstad Tunnel in Goteborg, Sweden ranged from 0.25-.41% of total non-methane hydrocarbons from June 27, 1991 to March 11, 1992(4). Amylene was detected in urban air samples taken in Cincinnati in the early afternoon (avg concn 3.8 ppb)(5). Amylene was detected in ambient air samples from Los Angeles, CA in 5 out of 23 samples ranging from 1-4 ppb from Sept 29-Nov 13, 1981(6). Amylene was detected in samples taken from March 12, 1990-March 11, 1991 in urban Washington, DC 48.21% of the time (mean concn 0.2 ppbv)(7). Amylene was detected in air samples from the Caldecott tunnel in San Francisco at 0.43% weight of total VOC's in Aug 1994 and 0.48% weight of total VOC's in Oct 1994(8). Amylene was detected in ambient air samples collected in downtown Houston, TX at concns ranging from 0-91.9 ppbC on Sept 1, 1973, 8.1-67.8 ppbC on Jan 30, 1974, and 0-4.1 ppbC on Apr 2, 1974(9). Amylene was detected in ambient air samples in the central Los Angeles business district during late summer and fall months of 1960, between the hours of 7 and 9 am at concns ranging from 0.002-0.018 ppm(10). Amylene was detected in air samples taken from various sites in Sydney Australia during the morning hours from Sept 1979 to June 1980 (avg concn 1.3 ppbV)(11). Amylene was detected at Huntington Park, CA on Oct 22, 1968 ranging from 0-4.2 ppb(12). Amylene was detected in air samples taken from Boone, NC (population 10,000) ranging from 0.1-4.1 ppb(13).|URBAN/SUBURBAN: The concn of amylene in air samples collected from 39 different U.S. cities from June to Sept of 1984-1986 from 0600 to 0900 averaged 0.4 ppb(1). Amylene has been reported to be 0.27% by mass of VOC emissions in 1990 in the United Kingdom(2). Amylene was detected, concn not specified, in 2 of 15 industrial area air samples taken in Riverside, CA(3). Amylene has been detected, concn not specified, in ambient air samples in Riverside, CA on Aug 21, 1969(4). Gas-phase reaction of amylene with the NO3 radical (concn ranging from 3.8-4.2X10+13 molec/cu cm) produced acetaldehyde, acetone, 2,2,3-trimethyloxirane, 3-methyl-3-nitroxy-2-butanone and 3-methyl-2-butanone. It was also found that the percent distribution of products was highly dependent upon pressure(5).|RURAL/REMOTE: From January 1-6, 1978 amylene was detected in Jones State forest, 38 miles north of Houston, TX, in a range of 0.1-7.1 ppbC(1). Amylene has been detected in ambient air samples taken from rural southern Appalachian Mountains of northwestern North Carolina from Sept 1981-Oct 1982 (concns ranging from 0-0.7 ppb)(2).

Toxicity

Amylene's production and use in organic syntheses(1) or as an octane additive(2) may result in its release to the environment through various waste streams(SRC). Industry gasoline, EPA certification gasoline and M-85 (85% methanol and 15% gasoline) contain 1.032%, 0.617%, and 0.142% of amylene, respectively(2). Whole gas of 87-89 octane contains 1.16% by weight amylene(3).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 68(SRC), determined from a structure estimation method(2), indicates that amylene is expected to have high mobility in soil(SRC). Volatilization of amylene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 0.110 atm-cu m/mole(3). The potential for volatilization of amylene from dry soil surfaces may exist based upon a vapor pressure of 468 mm Hg(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 68(SRC), determined from a structure estimation method(2), indicates that amylene is not expected to adsorb to suspended solids and sediment in water(SRC). Based on exposure of activated sludge to amylene in the Warburg respirometer test at 20 °C, percent theoretical oxygen demand after 24 hrs was 0.9(3). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 0.110 atm-cu m/mole(5). Volatilization half-lives for a model river and model lake are 2.5 and 80 hrs, respectively(SRC), using an estimation method(4). According to a classification scheme(6), an estimated BCF of 23(4,SRC), from a log Kow(7,SRC), suggests the potential for bioconcentration in aquatic organisms is low.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), amylene, which has a vapor pressure of 468 mm Hg at 25 °C(2), is expected to exist solely in the vapor phase in the ambient atmosphere. Vapor-phase amylene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4.4 hrs(SRC), calculated from its rate constant of 8.69X10-11 cu cm/molecule-sec at 25 °C(3). The rate constant for the vapor-phase reaction of amylene with ozone is 4.2X10-16 cu cm/molec sec(4); the half-life for this reaction in air is estimated to be 39 minutes at an atmospheric concn of 7X10+11 molec/cu cm for ozone(5). The rate constant for the vapor-phase reaction of amylene with the nitrate radical is 9.0X10-12 cu cm/molec sec(4); the half-life for this reaction in air is estimated to be 321 seconds at an ambient concn of 2.4X10+8 molec/cu cm at night(5).

The rate constant for the vapor-phase reaction of amylene with photochemically-produced hydroxyl radicals is 8.69X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 4.4 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of amylene with ozone is 4.2X10-16 cu cm/molec sec(2). This corresponds to an atmospheric half-life of 39 minutes at an atmospheric concn of 7X10+11 molec/cu cm for ozone(3). It is estimated that amylene will degrade into carbon monoxide (1.2%), carbon dioxide (2.4%), formaldehyde (2.5%), ethanol (23.6%), methylglyoxal and acetol(18.5%), 2-propanone (35.4%), acetic acid (3%), isopropyl hydroperoxide (6.1%), methane (1.1%) and unknown carbon products (6.2%) under summer conditions with reactive ozone (1.11X10+12 molec/cu cm) and OH radical (1.2X10+6 molec/cu cm)(4). The rate constant for the vapor-phase reaction of amylene with the nitrate radical is 9.0X10-12 cu cm/molec sec(2). This corresponds to an atmospheric half-life of 321 seconds based on an ambient concn of 2.4X10+8 molec/cu cm at night(3). Amylene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(5) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum.

An estimated BCF of 23 was calculated for amylene(SRC), using a log Kow of 2.67(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for amylene can be estimated to be about 68(SRC). According to a classification scheme(2), this estimated Koc value suggests that amylene is expected to have high mobility in soil.

The Henry's Law constant for amylene is 0.110 atm-cu m/mole(1). This Henry's Law constant indicates that amylene is expected to volatilize rapidly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 2.5 hrs(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 80 hrs(SRC). Amylene's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of amylene from dry soil surfaces may exist(SRC) based upon a vapor pressure of 468 mm Hg(3).

Occupational exposure to amylene may occur through inhalation and dermal contact with this compound at workplaces where amylene is produced or used(SRC). The general population may be exposed to amylene via inhalation of ambient air(1) with this compound and gasoline products containing amylene(2,3). Exposure to amylene between the months of Oct-Nov 1990 was found to be 0.11 ppm for gasoline consumers during self-serve fill-up operations at 6 service stations from three U.S. cities(1). Exposure levels for service station attendants, transport drivers and outside operators to amylene during the summer of 1984 was 1.986 mg/cu m (mean concn), 0.74 0 mg/cu m (mean concn), and 0.446 mg/cu m (mean concn), respectively(4).

Drug Information

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: 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. (ERG, 2016)

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Keep victim calm and warm. (ERG, 2016)

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Anticipate seizures and treat if necessary ... Use rapid rewarming techniques if frostbite occurs ... /Simple asphyxiants and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Monitor cardiac rhythm and treat arrhythmias if necessary ... Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Treat seizures with diazepam (Valium) ... /Simple asphyxiants and related compounds/

1,4-polyisoprene

2-Methyl-2-butene Use and Manufacturing

Methods of Manufacturing

DISTILLATION OF A CATALYTICALLY CRACKED GASOLINE STREAM, FOLLOWED BY EXTRACTION WITH AQUEOUS SULFURIC ACID AT LOW TEMP|Prepd by dehydration of tert-amyl alcohol in presence of p-toluenesulfonic acid|... A component of refinery gas.

Uses

Principally chemical intermediate for isoprene, additive in high octane fuel mfr, chemical intermediate for the pharmaceutical solvent, tertiary pentyl alcohol.

Production

50,000,000 - 100,000,000 lb|(1972) 1.45X10+11 GRAMS (PENTENES, MIXED)|(1975) 1.27X10+11 GRAMS (AMYLENES & PENTENES)|(1984) 697,131,000 lbs /Pentenes mixed/

Grades: 90%, 95% (Technical), 99% (Pure), & Research.

All other basic organic chemical manufacturing|2-Butene, 2-methyl-: ACTIVE|At one time it was used without success as a human anesthetic but produced better results in dentistry.

FLAME-IONIZATION CHROMATOGRAPHY IS SATISFACTORY FOR HYDROCARBON DETERMINATION. CONCN AS LOW AS 0.1-0.2 PPB CAN BE DETECTED, WITH FREEZING OUT FROM 100 ML OF AIR.|A METHOD PROPOSED FOR DETERMINING BETA-ISOAMYLENE OXIDE IN THE AIR OF INDUSTRIAL ROOMS IS BASED ON THE USE OF HYDROCHLORINATION, HYDROLYSIS OF THE CHLOROHYDRIN FORMED, & SUBSEQUENT STUDY OF CL(2-) BY NEPHELOMETRY WITH RESPECT TO INTERACTION WITH SILVER NITRATE.

Fire Hazards -> Flammable - 4th degree

Computed Properties

Molecular Weight:70.13
XLogP3:2.3
Exact Mass:70.078250319
Monoisotopic Mass:70.078250319
Heavy Atom Count:5
Complexity:38
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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