1-Butene

HCID 7844CAS 106-98-9

Basic information

Standard SMILES
C=CCC
InChIKey
VXNZUUAINFGPBY-UHFFFAOYSA-N
Molecular formula
C4H8
Average molar mass
56.11 g/mol
Monoisotopic mass
56.06260026

Overview

1-butene is a colorless gas. (NTP, 1992)

Names & identifiers

Preferred name
1-Butene
IUPAC
but-1-ene
English name
1-BUTENE
Molecular formula
C4H8
Molecular weight
56.11

Names & synonyms

1-BUTENEBut-1-eneEthylethylene106-98-91-Butylenealpha-ButyleneButene-1alpha-ButeneLY001N554LDTXSID1026746CHEBI:48362RefChem:6715
Show more names
N-BUTENE-Butylenen-Buten-11-N-BUTENE
DTXCID606746203-449-2BUTENE1-Butene-1-13C.alpha.-Butene.alpha.-Butylene1-C4H8Isotactic poly(1-butene)

Database identifiers

CAS
106-98-9、25167-67-3、9003-28-5
PubChem CID
7844
DTXSID
DTXSID1026746
ChEMBL
CHEMBL117210
ChEBI
CHEBI:48362
UNII
LY001N554L
EC Number
203-449-2、246-689-3
Nikkaji
J1.899.010E、J4.042H

Properties

Computed structural properties

XLogP
2.4
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
1
Heavy atoms
4

Experimental & physicochemical properties

Chemical ClassesFlammable agents - 4th degree
SpringerMaterials PropertiesCoriolis coupling
LogPlog Kow = 2.40
Odor · 2 items

Slightly aromatic odor

Gassy, slightly aromatic odor

Density · 4 items

0.6255 at 19.9 °F (NTP, 1992) - Less dense than water; will float

0.588 g/cu cm at 25 °C, 1 atm

Density of liquid 10.47 mol/L at 298.15 K; critical volume 0.240 L/mol

0.557 @25 °C

Color/FormColorless gas

Physicochemical properties

Melting point
185 °C · −185 °C(lit.)
Boiling point
6.3 °C · −6.3 °C(lit.)
Density
0.5951 · 0.5951
vapor density
1.93 · 1.93 (vs air)
vapor pressure
1939 mm · 1939 mm Hg ( 21.1 °C)
refractive index
1.3962 · 1.3962

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H220: Extremely flammable gas [Danger Flammable gases]

P203, P210, P222, P280, P377, P381, and P403 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.1% (2 of 1383) of reports.

Danger

H220 (99.6%): Extremely flammable gas [Danger Flammable gases]

Hazard information

Regulatory Information · 6 items

Chemical: 1-Butene

Chemical: Butene

Butene is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butene are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

1-Butene is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Butene are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 17-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15510

Status: Active Update: 06-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14810

Other Safety Information · 2 items

IMAP assessments - Butene: Human health tier I assessment

IMAP assessments - 1-Butene: Human health tier I assessment

DOT LabelFlammable Gas
Fire HazardsThis chemical is flammable. Vapor is heavier than air and may travel long distances to an ignition source and flash back. (NTP, 1992)
Fire PotentialVery dangerous fire hazard when exposed to heat, flame, or oxidizers.
Health HazardsSYMPTOMS: This compound may be an asphyxiant or a slight anesthetic at high concentrations. It may also cause eye irritation.

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. Vapor is heavier than air and may travel long distances to an ignition source and flash back. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Firefighting HazardsSpecial hazards arising from the substance or mixture: Carbon oxides
Fire Fighting Procedures · 2 items

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary. Further information: Use water spray to cool unopened containers.

To fight fire, stop flow of gas.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Contents under pressure. Storage class (TRGS 510): Gases
Cleanup Methods · 1 item

ACCIDENTAL RELEASE MEASURES; Personal precautions, protective equipment and emergency procedures: Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Clean up promptly by sweeping or vacuum.

Toxicology

Body Burden1-Butene has been detected in human expired air(1) at measured concentrations in exhaled breath up to 495 ppb, and an average emission of 36 ppb (140 ug/m cu)(2).
Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a log Kow of 2.40(2) and a regression-derived equation(3), indicates that 1-butene is expected to have high mobility in soil(SRC). Volatilization of 1-butene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.33X10-1 atm-cu m/mole(4). 1-Butene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2250 at 25 °C(5). Utilizing the Japanese MITI test, 3% of the Theoretical BOD was reached in 4 weeks(6) indicating that biodegradation is not an important environmental fate process in soil(SRC). However, alkenes can be utilized by a wide range of microorganisms and are catabolized via several routes, resulting in the unsaturated alcohol, aldehyde and fatty acid or the formation of epoxide, diol compounds and possibly hydroxyacids(7).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a log Kow of 2.40(2) and a regression-derived equation(3), indicates that 1-butene is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 2.33X10-1 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 2 hours and 3 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 18(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 3% of the Theoretical BOD was reached in 4 weeks(7) indicating that biodegradation is not an important environmental fate process in water(SRC). However, alkenes can be utilized by a wide range of microorganisms and are catabolized via several routes, resulting in the unsaturated alcohol, aldehyde and fatty acid or the formation of epoxide, diol compounds and possibly hydroxyacids(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-butene, which has a vapor pressure of 2.25X10+3 mm Hg at 25 °C(2), is expected to exist solely as a gas in the ambient atmosphere. Gas-phase 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 12 hours(SRC), calculated from its rate constant of 3.14X10-11 cu cm/molecule-sec at 25 °C(3). The rate constant for the vapor-phase reaction of 1-butene with ozone has been estimated as 1.2X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(4). This corresponds to an atmospheric half-life of about 23 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(5). Products from this reaction are formic and propionic acid(6). Based on a half-life of 149 hours, from and average rate constant of 5.4X10-15 cu cm/molec-sec(7,8), night-time degradation by the reaction with nitrate radicals is not expected to be a significant removal process. 1-Butene does not contain chromophores that absorb at wavelengths >290 nm(9) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey ValuesThe volatile vapor fraction emitted during the heating of four oils (rapeseed, Canola, peanut and soybean) was analyzed to determine its composition. 1-Butene was detected, concentration not specified, in all four heated oils(1).
Toxicity Summary · 1 item

IDENTIFICATION AND USE: 1-Butene is a colorless gas. It is is used for the production of a wide variety of chemicals in the gasoline and rubber processing areas. Most 1-butene is used as a comonomer for linear low-density polyethylene, which contains up to 10%. However, 1-butene is also used as a comonomer for modifying high-density polyethylene, which contains up to 4%. HUMAN STUDIES: 1-Butene is a simple asphyxiant and may be a CNS depressant in high concentrations. It has a low acute toxicity and is mildly irritating to the eye. On direct eye and skin contact liquid butene can cause burns and frostbite. The treatment of human peripheral blood mononuclear cells (PBMCs) and promyelocytic leukemia cells (HL60) for 24 hr resulted in an increase of DNA damage. HL60 cells were more resistant than PBMCs to the DNA damage. ANIMAL STUDIES: Exposure to 1-butene at target concentrations of 500, 2000, 8000 ppm (approximately 1147, 4589, 18359 mg/cu m) did not induce systemic toxicity in male and female rats exposed for 28 days or in pregnant female rats exposed for 14 days pre-mating, through mating and gestation to day 19. There were no treatment-related effects on the development of pups. As an anesthetic, it is 4.5 times more potent than ethylene. Exposure of mice to concentrations of 15% butene resulted in reversible signs of incoordination, confusion, and hyperexcitability; at 20% deep anesthesia in 8 to 15 min, with subsequent respiratory failure in 2 hr; and at 30% in 2 to 4 min and 40 min, respectively. A concentration of 40% resulted in profound anesthesia in 30 sec, with no CNS symptoms but with death in 10 to 15 min. ECOTOXICITY STUDIES: Tomato: epinasty in petiole: 50,000 ppm, 2 days.

Ecotoxicity Excerpts/PLANTS/ Tomato: epinasty in petiole: 50,000 ppm, 2 days.
Plant Concentrations · 1 item

Experiments were conducted in 1993 to monitor the hydrocarbon emissions from a mixed deciduous forest approximately 80 km northwest of Toronto, Canada(1). 1-Butene was the fourth most abundantly measured hydrocarbon above the Borden forest from April 29-June 3, 1993(1).

Regulatory information

Atmospheric Standards · 1 item

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. 1-Butene is produced, as an intermediate or a final product, by process units covered under this subpart.

DHS Chemicals of Interest (COI) · 6 items

Butene

1

10000

Flammable chemical that can be released at a facility.

1-Butene

1

Safety data

F
4.5-31
wgk
-
tsca
TSCA listed
ridadr
UN 1012
hs_code
2901230000
risk_code
12

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 3 items

Conjugation with glutathione appears to be an important excretion route for butene metabolites.

Butene is metabolized slowly through its 1-hydroxy derivative.

Butene is liberated from tetra- and tributyl-lead or tin during oxidative dealkylation by hepatic microsomes.

Absorption, Distribution and Excretion · 1 item

The absorption, distribution, elimination, hemoglobin adduct formation and DNA adduct formation of individual C2-C8 1-alkenes was studied in the rat after exposure to 300 ppm (688mg/cu m), 12 hr a day for 3 consecutive days. The concentrations of the alkenes were measured in blood, lung, brain, liver, kidney and peri-renal fat immediately after each exposure and 12 hr after the third exposure. DNA adducts were determined by (32)P-postlabeling in liver. Hemoglobin adducts were determined in erythrocytes by GC/MS and GC/MS/MS. Concentrations of 1-alkenes in blood and organs reached a steady-state level after the first 12 hr exposure, and the concentrations 12 hr after the last exposure were generally low, except in fat. Concentrations of 1-alkenes in blood and the different tissues increased with increasing number of carbon atoms. However, DNA adducts and hemoglobin adducts decreased with increasing number of carbon atoms with the most pronounced decrease being from C2 to C3. The decrease in hemoglobin adducts was more pronounced than DNA adducts. All 1-alkenes caused formation of detectable levels of hemoglobin and DNA adducts, although the levels of hemoglobin adducts after C4-C8 exposure were low. These results also indicate that extrapolation within the homologous series is possible. /1-Alkenes/

Uses & manufacturing

Uses · 3 items

/1-Butene/ is used for the production of a wide variety of chemicals in the gasoline and rubber processing industries.

Most high-purity 1-butene is used as a comonomer for linear low-density polyethylene (LLDPE) and for modifying high-density polyethylene (HDPE), which contains up to 4%.

COMONOMER FOR HIGH DENSITY POLYETHYLENE FOR BLOW-MOLDING RESINS; MONOMER FOR POLYBUTENE USED IN PLASTIC PIPE & FILM; INT FOR 1,2-BUTYLENE OXIDE

U.S. Production · 6 items

2023: 1,000,000,000 - <2,500,000,000 lb

2023: 1,000,000,000 - <2,500,000,000 lb

(1984) 1.20X10+11 g

(1991) 7.30x10+8 lb

(1986) 441,473 lbs

(1987) 461,831 lbs

Consumption Patterns · 5 items

Polyethylene comonomer, 45%; (96% linear low-density polyethylene (LLDPE), 4% HDPE); exports (for LLDPE and HDPE), 35%; valeraldehyde, 9%; polybutene-1, 8%; butylene oxide, 1%; other (including mercaptans, sec-butylphenols and solvents), 2%.

CHEMICAL PROFILE: Butene-1. Demand: 1987: 470 million lb; 1988: 490 million lb; 1992 /projected/: 600 million lb (Includes exports; imports are negligible).

Polyethylene comonomer, 65%; (90% LLDPE, 10% HDPE); valeraldehyde, 10%; polybutene-1, 14%; butylene oxide, 5%; other (including mercaptans, sec-butylphenols and solvents), 6%.

Demand: 1996: 460 million lb; 1997: 475 million lb; 2001: 550 million lb (does not include exports; imports currently negligible)

For more Consumption Patterns (Complete) data for 1-Butene (6 total), please visit the HSDB record page.

Consumer Uses · 2 items

Not Known or Reasonably Ascertainable

Fuel

Industry Uses · 2 items

Fuel

Intermediate

Methods of Manufacturing · 4 items

There are two important sources for the commercial production of butylenes: catalytic or thermal cracking, and steam cracking. In these two processes, butylenes are always produced as by-products. /Butylenes/

In the Institut Francais du Petrole process, ethylene is dimerized into polymer-grade 1-butene (99.5% purity) suitable for the manufacture of linear low density polyethylene. It uses a homogeneous catalyst system that eliminates some of the drawbacks of heterogeneous catalysts. It also inhibits the isomerization of 1-butene to 2-butene, thus eliminating the need for superfractionation of the product. The process also uses low operating temperatures, 50-608 °C, and pressures.

Alphabutol Process (1-Butene). ... ethylene is selectively dimerized to 1-butene by employing a homogeneous titanium catalyst at 50-60 °C and 2.3-2.7 MPa ethylene pressure. ... the proposed mechanism does not involve metal hydrides but a titanium(IV) cyclopentane species that decomposes via beta-hydrogen elimination to 1-butene.

Obtained by cracking of petroleum oils and by thermal decomposition of butane or pentane or isopentane. ... From butyl alcohol by treatment with concentrated H2SO4 ... .

Applications · 3 items

Description1-Butene is a colourless, stable but polymerises exothermically, extremely flammable liquefied gas with an aromatic odour. It is insoluble in water and is one of the isomers of butane. 1-Butene readily forms explosive mixtures with air. It is incompatible with strong oxidising agents, halogens, halogen acids, metal salts, boron trifluoride, fluorine, and nitrogen oxides. 1-Butene of high purity is made by cracking naphtha and separating it from other products by an extra-high-purity distillation column. It is an important organic compound in the production of several industrial materials – for instance, linear low-density polyethylene (LLDPE), a more flexible and resilient polyethylene, and a range of polypropylene resins – and in the production of polybutene, butylene oxide, and the C4 solvents secondary butyl alcohol (SBA) and MEK. The vapour of 1-butene is heavier than air and may travel long distances to an ignition source and flash back.

UsesButenes are used extensively in gasoline production to produce high-octane gasoline compounds.Another large use of normal butenes in the petrochemical industry is in the production of 1,3-butadiene. Butene is used in the plastics industry to make both homopolymers and copolymers. Another use of 1-butene is in the production of solvents containing four carbons such as secondary butyl alcohol and methyl ethyl ketone (MEK).

General DescriptionColorless gas.

Additional notes

DefinitionChEBI: A butene with unsaturation at position 1.

Related reactions

114 records

Linked notes

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