trans-2-ブテン

trans-2-BUTENE

HCID 62695CAS 107-01-7

基本情報

標準SMILES
C/C=C/C
InChIKey
IAQRGUVFOMOMEM-ONEGZZNKSA-N
分子式
C4H8
平均分子量
56.11 g/mol
単同位体質量
56.06260026

概要

2-butene appears as a colorless liquefied petroleum gas. Asphyxiate gas. Flammability limits in air 1.8-9.7% by volume.

名称と識別子

優先名称
trans-2-BUTENE
IUPAC
(E)-but-2-ene
現地名
trans-2-ブテン
英語名
trans-2-butene
分子式
C4H8
分子量
56.11

名称と別名

trans-2-Butene(E)-But-2-ene624-64-6trans-Butenetrans-but-2-ene2-BUTENE, (E)-2-trans-Butenebeta-trans-ButyleneLow-boiling butene-2trans-1,2-Dimethylethylenee-but-2-ene017NGL487F
名称をさらに表示
trans-2-ブテンcis-ブテンtrans-ブテンsym-ジメチルエチレンtrans-β-ブチレンβ-ブチレン(E)-2-ブテン(2E)-2-ブテン2-ブテン(トランス)2ブテン(トランス)(E)-ブタ-2-エン(2E)-ブタ-2-エンTR-2-BUTENE(E)-2-C4H8t-butene-22-BUTYLENE2-Butene,(E)-
CHEBI:48365RefChem:933259210-855-3618-356-62-BUTENEPseudobutylenebeta-Butylene(E)-2-Butene

データベース識別子

CAS
107-01-7、624-64-6、68956-54-7、9003-17-2
PubChem CID
62695
DTXSID
DTXSID7027255
ChEBI
CHEBI:48363
UNII
017NGL487F
EC Number
203-452-9、210-855-3、618-356-6
Nikkaji
J1.677B、J144.989C、J2.447.817C

物性

構造計算による物性

XLogP
2.3
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
0
重原子数
4

実験および物理化学的性質

Chemical Classes · 2 件

Flammable agents - 4th degree

Flammable agents - 4th degree

SpringerMaterials PropertiesSchoenflies notation
LogP · 4 件

log Kow = 1.85 (mixture of 70% cis- and 30% trans-2-Butene)

log Kow = 2.31

2.31

2.31

OdorSlightly aromatic odor
Density · 4 件

0.6042 g/cu cm at 20/4 °C

Density of liquid: 10.69 mol/l @ 25 °C; critical volume 0.238 l/mol

Density (at the boiling point of the liquid): 0.6 kg/l

0.599 @25 °C

Viscosity0.00763 mPa

物理化学的性質

融点
140 °C · −140 °C(lit.)
沸点
1 °C · 1 °C(lit.)
比重(密度)
0.599 · 0.5990
蒸気密度
2 · 2 (vs air)
蒸気圧
2575 mm · 2575 mm Hg ( 37.7 °C)
屈折率
1.3932 · 1.3932
化学的性質 · 2 件

化学的特性2-Butene, C4H8, can occur in trans or cis conformation; the former is the more stable form. It is a colorless, extremely flammable gas. 2-Butene occurs in coal gas and has been detected in diesel exhaust. The more highly reactive trans-2-butene occurs at much lower concentrations in the atmosphere than other comparable hydrocarbons.

化学性质熱分解温度: 0.9℃, 接触分解温度: 4.93℃

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H220: Extremely flammable gas [Danger Flammable gases]

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

Danger

H220 (100%): Extremely flammable gas [Danger Flammable gases]

P203, P210, P222, P280, P377, P381, P403, and P410+P403 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 6 件

Chemical: 2-Butene

Chemical: 2-Butene, (E)-

2-Butene, (2E)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Butene, (2E)- 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: 10-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/13346

2-Butene: HSNO Approval: HSR005566 Approved with controls

trans-2-Butene: HSNO Approval: HSR005568 Approved with controls

Other Safety Information · 2 件

IMAP assessments - 2-Butene, (E)-: Human health tier I assessment

IMAP assessments - 2-Butene: Human health tier I assessment

DOT LabelFlammable Gas
Fire Hazards · 2 件

Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:

Extremely flammable. Gas/air mixtures are explosive.

Fire PotentialFlammable gas.
Health HazardsExcerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:

Shut off supply; if not possible and no risk to surroundings, let the fire burn itself out. In other cases extinguish with water spray, dry powder, alcohol-resistant foam. In case of fire: keep cylinder cool by spraying with water. Combat fire from a sheltered position.

First Aid Measures · 3 件

Fresh air, rest. Artificial respiration may be needed. Refer immediately for medical attention.

ON FROSTBITE: rinse with plenty of water, do NOT remove clothes. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

First AidExcerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:
Safe StorageFireproof. Store outside or in a separate well-ventilated building.
Firefighting HazardsSpecial hazards arising from the substance or mixture: Carbon oxides
Fire Fighting Procedures · 5 件

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.

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.

Use water spray to cool unopened containers.

Very dangerous fire hazard when exposed to heat or flame ... To fight fire, stop flow of gas.

毒性情報

Body Burden · 2 件

2-Butene has been detected in exhaled air. In the majority of subjects, concentrations of the cis- form were greater than those for the trans- isomer(1). Of 18 personal air samples from attendants at a high volume gasoline service station in PA, 1983, 2-butene was detected but not quantified in 17 samples and measured in one sample at a concentration of 0.1 ppm(2). Workers in the petroleum field are likely to be exposed to 2-butene by inhalation of gasoline fumes during the production, transport or dispensing of motor fuels; personal air samples taken for workers in the petroleum industry indicated that 14 of 56 outside operators, 48 of 49 transport drivers and 48 of 49 service attendants were exposed to 2-butene(3).

2-Butene has been detected in exhaled air; in the majority of subjects, concentrations of the cis form were greater than those for the trans isomer(1). trans-2-Butene was detected in the expired air of 6 out of 10 air samples taken from 8 smoking and non-smoking male volunteers from Texas, at concentrations ranging from 0.054 to 80.0 ug/h, averaging 14.2 ug/h for the positive samples(2).

Environmental Fate · 6 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 40(SRC), determined from a log Kow of 1.85(2) and a regression-derived equation(3), indicates that 2-butene is expected to have very high mobility in soil(SRC). Volatilization of 2-butene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.54X10-1 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 2-Butene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1600 mm Hg at 25 °C(5). Biodegradation data in soil were not available(SRC, 2018). However, based on pure culture studies resulting in oxidation of cis- and trans-2-butene and subsequent accumulation of the metabolite(6), primary biodegradation may be an important environmental fate process under certain conditions in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 40(SRC), determined from a log Kow of 1.85(2) and a regression-derived equation(3), indicates that 2-butene is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 1.54X10-1 atm-cu m/mole(SRC), developed using a fragment constant estimation method(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 8(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2018). However, based on pure culture studies resulting in oxidation of cis- and trans-2-butene and subsequent accumulation of the metabolite(7), primary biodegradation may be an important environmental fate process under certain conditions in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-butene, which has a vapor pressure of 1600 mm Hg at 25 °C(2), is expected to exist solely as a gas in the ambient atmosphere. Gas-phase 2-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 6.4 hours(SRC), calculated from its rate constant of 6.00X10-11 cu cm/molecule-sec at 25 °C(3). The rate constant for the vapor-phase reaction of 2-butene with ozone has been measured in the range of 5.98X10-17 to 4.32X10-16 cu cm/molecule-sec at 25 °C(4). This corresponds to an atmospheric half-life of about 0.64 to 4.6 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4). The rate constant for the gas-phase nighttime reaction of 2-butene with nitrate radicals has been measured in the range of 1.89X10-13 to 2.11X10-13 cu cm/molecule-sec at 25 °C(5). This corresponds to an atmospheric half-life of about 0.5 hours at an atmospheric concentration of 2X10+9 nitrate radicals per cu cm(5). 2-Butene does not contain chromophores that absorb at wavelengths >290 nm(6) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 100(SRC), determined from a log Kow of 2.31(2) and a regression-derived equation(3), indicates that trans-2-butene is expected to have high mobility in soil. Volatilization of trans-2-butene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 0.224 atm-cu m/mole(4). trans-2-Butene may volatilize from dry soil surfaces based upon a vapor pressure of 1750 mm Hg at 25 °C(5). Biodegradation data in soil were not available(SRC, 2018). However, based on pure culture studies resulting in oxidation of trans-2-butene and subsequent accumulation of the metabolite(6), primary biodegradation may be an important environmental fate process under certain conditions in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 100(SRC), determined from a log Kow of 2.31(2) and a regression-derived equation(3), indicates that trans-2-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 0.224 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 16(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2018). However, based on pure culture studies resulting in oxidation of trans-2-butene and subsequent accumulation of the metabolite(7), primary biodegradation may be an important environmental fate process under certain conditions in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trans-2-butene, which has a vapor pressure of 1750 mm Hg at 25 °C(2), is expected to exist solely as a gas in the ambient atmosphere. Gas-phase trans-2-butene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals, ozone molecules, and nitrate radicals(SRC). The half-life for the reaction with hydroxyl radicals is estimated to be 6 hours(SRC) calculated from its rate constant of 6.4X10-11 cu cm/molecule-sec at 25 °C(3). The half-life for the reaction with ozone molecules is estimated to be 0.64 to 4.6 hours(SRC) calculated from rate constants in the range of 5.98X10-17 to 4.32X10-16 cu cm/molecule-sec at 25 °C(4). The half-life for the nighttime reaction with nitrate radicals is estimated to be 0.5 hours(SRC) calculated from its rate constant of 2.11X10-13 cu cm/molecule-sec at 25 °C(5). trans-2-Butene does not contain chromophores that absorb at wavelengths >290 nm(6) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Exposure RoutesExposure mainly occurs via inhalation.
Toxicity Summary · 2 件

IDENTIFICATION AND USE: 2-Butene is a colorless gas. It is used as a solvent and a cross-linking agent. It is also used to polymerize gasoline, and for butadiene synthesis, as well as the synthesis of derivatives. HUMAN STUDIES: 2-Butene is an asphyxiant gas. Rapid evaporation of liquid 2-butene may cause frostbite. it may cause effects on the CNS. Exposure may result in unconsciousness. ANIMAL STUDIES: Rats were exposed for 4 hr to 2-butene at a nominal concentration of 10,000 ppm (22,948 mg/cu m). No clinical signs were seen and normal growth occurred over the 14 d observation period. 2-Butene is a cardiac sensitizer in dogs. In developmental studies in rats, there were no effects on mating behavior, fertility and gestation indices, the number of implantation sites and corpora lutea per dam, numbers of pups delivered, viability of pups at and after birth and the pup sex ratio when compared to the control group. There were no treatment-related effects on the development of pups. Male and female rats were exposed to 2-butene at target concentrations of 2500 or 5000 ppm (5737 or 11,474 mg/cu m) for two weeks prior to breeding, during breeding (1 week) and until day 19 of gestation (39-46 days of exposure). No significant systemic toxicity occurred in either sex, or in pregnant female rats. 2-Butene is a CNS depressant. About 13 to 13.5% (300 or 400 mg/L) causes deep CNS depression, and in mice about 19% (120 to 420 mg/L) is fatal. It is a mild mucous membrane irritant. A chromosome aberration study was conducted with 2-butene in rat lymphocytes in vito. No significant increases were seen in the frequency of chromosome aberrations either in the presence or absence of a metabolic activation. 2-Butene was not mutagenic to S. typhimurium TA98, TA100, TA1535, TA 1537 and E.coli WP2uvrA, with or without metabolic activation.

IDENTIFICATION AND USE: trans-2-Butene is a colorless gas. It is used as a solvent, as a cross-linking agent, in the polymerization of gasoline, and in butadiene synthesis. It is also used in the synthesis of C4 and C5 derivatives. HUMAN STUDIES: trans-2-Butene is a simple asphyxiant. Rapid evaporation of liquid 2-butene (in its cis or trans form, or as a mixture of both) may cause frostbite. The substance may cause effects on the central nervous system. Exposure may result in unconsciousness. ANIMAL STUDIES: There are no data available.

Average Daily Intake · 1 件

Intake: 11.5 mg/m cu: EHE max (maximum estimated human exposure) = 5 ppm or 11.5 mg/m cu equivalent to the peak concentration at working place(1). <0.23 mg/m cu TWA (time-weighted average) at working place or EHE mean <0.1ppm, (calculated)(1).

Signs and Symptoms · 3 件

Dizziness. Unconsciousness. Suffocation.

ON CONTACT WITH LIQUID: FROSTBITE.

See Skin.

法規制情報

DHS Chemicals of Interest (COI) · 6 件

2-Butene

1

10000

Flammable chemical that can be released at a facility.

2-Butene-trans

1

安全データ

wgk
3
tsca
TSCA listed
rtecs
EM2932000
ridadr
UN 1012 2.1
hs_code
2901230000
risk_code
12-11

化学と産業

薬理情報

Metabolism/MetabolitesIn rat liver cytosol meso-2,3-dibromobutane was converted, almost exclusively, into trans-2-butene while racemic-2,3-dibromobutane gave rise to cis-2-butene.
Absorption, Distribution and Excretion · 2 件

2-Butene has been detected in exhaled air. In the majority of subjects, concentrations of the cis form were greater than those for the trans isomer.

2-Butene has been detected in exhaled air. In the majority of subjects, concentrations of the cis form were greater than those for the trans isomer.

用途と製造

Uses · 6 件

INT FOR BUTADIENE, HEPTENES, SEC-BUTYL ALC, BUTYLENE OXIDE; PRODN OF HIGH-DENSITY POLYETHYLENE & POLYMER GASOLINES

Solvent, cross-linking agent, polymerization of gasoline, butadiene synthesis; synthesis of C4 and C5 derivatives.

CHEM INT FOR GASOLINE ALKYLATE & POLYGAS (BUTYLENES).

REFINERY FUEL (MIXT OF BUTYLENES).

CHEM INT, EG, FOR BUTADIENE & SEC-BUTANOL (AS MIXT).

For more Uses (Complete) data for trans-2-Butene (6 total), please visit the HSDB record page.

U.S. Production · 5 件

2023: 100,000,000 - <500,000,000 lb

(1984) 3.56X10+11 g /1-Butene and 2-Butene mixed/

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 2-Butene:

(1982) 5X10+11 G (EST; IN MIXT OF BUTYLENES)

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: trans-2-Butene:

Consumer UsesIntermediate
Industry UsesIntermediate
Methods of Manufacturing · 6 件

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/

1-Butene and isobutylene cannot be economically separated into pure components by conventional distillation because they are close boiling isomers. 2-Butene can be separated from the other two isomers by simple distillation. There are four types of separation methods available: (1) selective removal of isobutylene by polymerization and separation of 1-butene; (2) use of addition reactions with alcohol, acids, or water to selectively produce pure isobutylene and 1-butene; (3) selective extraction of isobutylene with a liquid solvent, usually an acid; and (4) physical separation of isobutylene from 1-butene by absorbents.

Disproportionation or the metathesis reaction offers an opportunity to convert surplus olefins to other desirable olefins. Phillips Petroleum and Institut Francais du Petrole have pioneered this technology for the dimerization of light olefins. The original metathesis reaction of Phillips Petroleum was intended to convert propylene to 2-butene and ethylene. The reverse reaction that converts 2-butene in the presence of excess ethylene to propylene has also been demonstrated. In this process, ethylene is first dimerized to 2-butene followed by metathesis to yield propylene. Since this is a two-stage process, 2-butene can be produced from the first stage, if needed. In the dimerization step, about 95% purity of 2-butene is achieved at 90% ethylene conversion.

... /A/ process has emerged that consists of catalytically hydroisomerizing 1-butene to 2-butenes. In this process, trace quantities of butadienes are also hydrogenated to yield feedstocks rich in isobutylene which can then be easily separated from 2-butenes by simple distillation. /2-Butenes/

For more Methods of Manufacturing (Complete) data for 2-Butene (6 total), please visit the HSDB record page.

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/

Formulations/PreparationsGrade: Technical, 95%; CP 99.0%; Research 99.9%.
応用分野 · 3 件

用途ポリブテン?SEC-ブタノール原料、カセットコンロ?ライター燃料 (化学工業日報社)

使用trans-2-Butene can be used as a monomer unit to produce high molecular weight polyolefins with well-defined microstructures by nickle-catalyzed polymerization reaction. It is also used as a reactant in the isomerization reaction to produce the corresponding isomer using acid-activated catalysts.

一般的な説明A colorless liquefied petroleum gas. An asphyxiant. Flammability limits of 1.8-9% by volume.

調製方法

2-Butene has been recovered from refining gases or produced by petroleum cracking. It is a component in the production of gasolines, butadiene, and a variety of other chemicals.

純化方法The gas is dried with CaH2 and purified by gas chromatography. [Beilstein 1 H 205, 1 II 176, 1 III 730, 1 IV 781.] HIGHLY FLAMMABLE.

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関連反応

12 件

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