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3-Methyl-1-butene

3-Methyl-1-butene structure

3-Methyl-1-butene 

structure
  • CAS No:

    563-45-1

  • Formula:

    C5H10

  • Chemical Name:

    3-Methyl-1-butene

  • Synonyms:

    1-Butene,3-methyl-;3-Methyl-1-butene;α-Isoamylene;2-Methyl-3-butene;Isopropylethylene;Isopropylethene;3,3-Dimethylpropene

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Colorless, extremely volatile liquid or gas; disagreeable odor.Soluble in alcohol; insoluble in water.


3-methyl-1-butene appears as a colorless volatile liquid with a disagreeable odor. Insoluble in water and less dense than water. Vapors heavier than air. Used to make other chemicals.|GasVapor; Liquid


3-methyl-1-butene appears as a colorless volatile liquid with a disagreeable odor. Insoluble in water and less dense than water. Vapors heavier than air. Used to make other chemicals.|3-methylbut-1-ene is an alkene that is but-1-ene carrying a methyl substituent at position 3.

3-Methyl-1-butene Basic Attributes

70.13

70.13

209-249-1

I08ZWX8BKL

2561

DTXSID7060336

... gas

Characteristics

0

2.72

3-methyl-1-butene appears as a colorless volatile liquid with a disagreeable odor. Insoluble in water and less dense than water. Vapors heavier than air. Used to make other chemicals.

0.6213 g/cm3 @ Temp: 25 °C

-168.5 °C

20.1 °C

-57 °C

1.384

In water, 130 mg/l @ 25 deg C.

−20°C

14.97 psi ( 20 °C)

Inflammable in case of open flame, high temperature, oxidant; burning produces irritating smoke

Explosive in the form of vapor when exposed to heat or flame.

Disagreeable odor

3.18e-11 cm3/molecule*sec

Hydroxyl radical rate constant= 3.18X10-11 cu cm/molecule-sec @ 25 °C

Highly flammable. Insoluble in water.

Hydrocarbons, Aliphatic Unsaturated

Highly Flammable

3-METHYL-1-BUTENE may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions.

689 °F (365 °C)

Lower flammable limit: 1.5% by volume; Upper flammable limit: 9.1% by volume

Safety Information

I

3.1

UN 2561 3/PG 1

3

12-36/37/38-65

16-26-62

F+,Xn

Storehouse ventilated at low temperature and dry; stored separately from oxidants and acids; not easy to store for a long time to prevent polymerization

Explosive when mixed with air

P210-P261-P301 + P310-P305 + P351 + P338-P331

H224-H304-H315-H319-H335

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.

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 (100%): Extremely flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P331, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 155 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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, DANGEROUS FIRE ... RISK|Very dangerous fire hazard when exposed to heat, flame, or oxidizers.

EXPLOSIVE LIMITS: 1.6 TO 9.1%|LEL: 1.5%; UEL: 9.1%|Explosive in the form of vapor when exposed to heat or flame.

To fight fire, use alcohol foam, mist, spray, dry chemical, carbon dioxide.

/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 3-METHYL-1-BUTENE (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 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.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 4 - Materials that rapidly or completely vaporize at atmospheric pressure and normal ambient temperature or that are readily dispersed in air and burn readily.| 0 - Materials that in themselves are normally stable, even under fire conditions.

3-Methyl-1-butene is one of the alkenes formed during the combustion of fuel by various engines. The amount of 3-methyl-1-butene detected or its absence from the exhaust emissions is dependent upon the type of fuel used. 3-Methyl-1-butene was identified, not quantified, among the alkenes detected in the exhaust of an afterburning turbojet engine J85-GE-5B(1). The fuel used by the jet engines was kerosene JP5 (85.9% paraffins, 13.4% aromatics and 0.7% olefins). The exhaust emissions of two- (moped) and four-stroke (lawn mower) engines were tested for no-methane hydrocarbons using alkylate- and reformate-based fuels(2). 3-Methyl-1-butene constituted 0.09 weight percent of the emitted hydrocarbons even though it was not present in the alkylate-based fuel. It constituted 0.05 and 0.06 weight percent of reformate-based fuel and its exhaust, respectively. Amounts of C2-C6 hydrocarbons in the exhaust emissions of diesel-burning ferries was compared in Skagerak-Kattegatt-Oresund region of Sweden (3). The amount of 3-methyl-1-butene ranged from <0.03 to 0.05 mg/cu nm during both the crossing and the low-speed maneuvering of the ferries. 3-Methyl-1-butene was also detected in the stack emissions of waste incineration plants(4).

SOURCE DOMINATED: 3-Methyl-1-butene was detected in an air samples from Atlanta collected between Aug 23-27, 1990 during the morning rush hour. The average concentration detected was 0.1583 +/- 0.0091 ppbC%(1). In air samples collected on Aug 27, 1990 from Atlanta's Hartsfield International Airport, an average concentration of 3-methyl-1-butene was monitored to be 0.090 +/- 0.022 ppbC%. 3-Methyl-1-butene was also detected in Tingstad Tunnel in Gotesborg, Sweden(2) in samples collected on Jun 6, 1991, Jan 15, Feb 10 and 19, 1992. The percent concentration ranged form 0.06 - 0.11% of the non-methane volatile hydrocarbons.|URBAN/SUBURBAN: A small amount of 3-methyl-1-butene, in the range of 0-2 ppbV, was identified in the Los Angeles air during Septr 29-Nov 13, 1981(1). A mean concentration of 0.9 mg/cu m of 3-methyl-1-butene was measured in the ambient air samples collected during March 20, 1996 to April 16, 1997 in Porto Alegre, Brazil(2). 3-Methyl-1-butene was detected in the ambient atmosphere in city of Lancaster, Northwest England during May-July 1983 with a mean concentration of 38.3 ppbC(3).|RURAL/REMOTE: 3-Methyl-1-butene was a minor component of C2-C6 hydrocarbons measured in rural Northwest England during May-July 1983(1). Mean concentration of 3-methyl-1-butene detected was <0.5 ppbC.

Toxicity

3-Methyl-1-butene's production and use as an intermediate in the manufacture of high-octane fuel and petroleum resins may result in its release to the environment through various waste streams(1). It is emitted in vehicular exhaust from both gasoline and diesel engines(2,3).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 68(SRC), determined from a structure estimation method(2), indicates that 3-methyl-1-butene is expected to have high mobility in soil(SRC). Volatilization of 3-methyl-1-butene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.54 atm-cu m/mole(SRC), determined using the vapor pressure of 903 mm Hg(4), and its water solublity value of 130 mg/l(5). The potential for volatilization of 3-methyl-1-butene from dry soil surfaces may exist(SRC) based upon its vapor pressure(4). 3-Methyl-1-butene's linear, relatively low molecular weight, hydrocarbon structure suggests that biodegradation in soil is expected to be an important fate process(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 68(SRC), determined from a structure estimation method(2), indicates that 3-methyl-1-butene is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 0.54 atm-cu m/mole(SRC), determined using its vapor pressure of 903 mm Hg(7), and its water solublity value of 130 mg/l(8). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 0.855 hr and 79.56 hr, respectively(SRC). 3-Methyl-1-butene's linear, relatively low molecular weight, hydrocarbon structure suggests that biodegradation in water is expected to be an important fate process(10). According to a classification scheme(5), an estimated BCF of 20(SRC), from an estimated log Kow of 2.6(6) and a regression-derived equation(9), 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), 3-methyl-1-butene, which has a vapor pressure of 903 mm Hg at 25 °C(2), is expected to exist solely as a gas in the ambient atmosphere. Gas-phase 3-methyl-1-butene 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 0.5 days(SRC), calculated from its estimated rate constant of 3.18X10-11 cu cm/molecule-sec at 25 °C(3). The rate constant for the gas-phase reaction of 3-methyl-1-butene with ozone has been measured as 9.50X10-18 cu cm/molecule-sec at 25 °C(4). This corresponds to an atmospheric half-life of about 1 hr at an atmospheric concentration of 7X10+11 ozone molecules per cu m(4).

The rate constant for the vapor-phase reaction of 3-methyl-1-butene with photochemically-produced hydroxyl radicals has been estimated as 2.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 0.5 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the gas-phase reaction of 3-methyl-1-butene with ozone has been measured as 9.50X10-18 cu cm/molecule-sec at 25 °C(4). This corresponds to an atmospheric half-life of about 1 hr at an atmospheric concentration of 7X10+11 ozone molecules per cu m(3). 3-Methyl-1-butene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum.

An estimated BCF of 20 was calculated for 3-methyl-1-butene(SRC), using an estimated log Kow of 2.6(1,SRC) 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 3-methyl-1-butene can be estimated to be about 68(SRC). According to a classification scheme(2), this estimated Koc value suggests that 3-methyl-1-butene is expected to have high mobility in soil.

The Henry's Law constant for 3-methyl-1-butene is estimated as 0.54 atm-cu m/mole(SRC) from its vapor pressure, 903 mm Hg(1), and water solubility, 130 mg/l(2). This Henry's Law constant indicates that 3-methyl-1-butene is expected to volatilize rapidly from water surfaces(3). 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)(3) is estimated as 0.85 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 3.3 days(SRC). 3-Methyl-1-butene's estimated Henry's Law constant(SRC) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of 3-methyl-1-butene from dry soil surfaces may exist(SRC) based upon a vapor pressure of 903 mm Hg(1).

Occupational exposure to 3-methyl-1-butene may occur through inhalation and dermal contact with this compound at workplaces where 3-methyl-1-butene is produced or used. The general population may be exposed to 3-methyl-1-butene from contact with fuels, consumer products containing this compound, and inhalation of diesel and gasoline engine exhaust. (SRC)

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. Monitor for pulmonary edema and treat if necessary ... Anticipate seizures and treat as necessary ... For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... Treat frostbite with rapid rewarming techniques ... /Aliphatic hydrocarbons and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... Treat seizures with diazepam (Valium) ... Use proparacaine hydrochloride to assist eye irrigation ... /Aliphatic hydrocarbons and related compounds/

3-Methyl-1-butene Use and Manufacturing

Methods of Manufacturing

Cracking of petroleum, a component of refinery gas.|CATALYTIC CRACKING OR STEAM CRACKING OF PETROLEUM FOLLOWED BY ISOLATION OF C5 FRACTION AND EXTRACTION WITH COLD AQUEOUS SULFURIC ACID

Uses

Organic synthesis, high-octane fuel manufacture.


Fuels and fuel additives


Fuels and related products

Production

10,000,000 - 50,000,000 lb|(1977) AT LEAST 4.54X10+8 GRAMS|(1981) 7.43X10+10 G (TOTAL, MIXED PENTENES)

Grades: Research, 99% min, technical, 95% min.

Petroleum refineries|1-Butene, 3-methyl-: ACTIVE

Fire Hazards -> Flammable - 4th degree

Computed Properties

Molecular Weight:70.13
XLogP3:2.2
Rotatable Bond Count:1
Exact Mass:70.078250319
Monoisotopic Mass:70.078250319
Heavy Atom Count:5
Complexity:27
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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