1,2-부타디엔

1,2-Butadiene

HCID 11535CAS 590-19-2

기본 정보

표준 SMILES
C=C=CC
InChIKey
QNRMTGGDHLBXQZ-UHFFFAOYSA-N
분자식
C4H6
평균 분자량
54.09 g/mol
단동위원소 질량
54.04695019

이름 및 식별자

우선 이름
1,2-Butadiene
IUPAC
buta-1,2-diene
현지명
1,2-부타디엔
영어명
1,2-BUTADIENE
분자식
C4H6
분자량
54.09

이름 및 동의어

1,2-BUTADIENEbuta-1,2-dieneAllene, methyl-MethylajoeneHSDB 5705UNII-2AZI943A8R2AZI943A8REINECS 209-674-2CH2=C=CHCH31,2-BUTADIENE [HSDB]DTXSID5027225CHEBI:39480
이름 더 보기
1,2-부타디엔methyl-allen1,2-Butadien1,2-BUTADIENE, PRESSURE TIN1,2-butadiene (Methyl allene)1,2-BUTADIENE 90+% PRESSURE TIN
EC 209-674-21MethylalleneAllene, methylRefChem:71747DTXCID707225InChI=1/C4H6/c1-3-4-2/h4H,1H2,2HQNRMTGGDHLBXQZ-UHFFFAOYSA-NMethylallene

데이터베이스 식별자

CAS
590-19-2
PubChem CID
11535
DTXSID
DTXSID5027225
ChEBI
CHEBI:39480
UNII
2AZI943A8R
EC Number
209-674-2
Nikkaji
J2.683B

물성

구조 계산 물성

XLogP
1
극성 표면적
0 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
0
회전 가능 결합 수
0
무거운 원자 수
4

실험 및 물리화학적 성질

Density0.676 @ 0 °C/4 °C
Color/FormVolatile, clear, colorless liquid or vapor.
SolubilityInsol in water; very sol in benzene; miscible in alcohol and ether
Boiling Point10.9 °C
Decomposition · 2건

1,2-Butadiene decomposes to complex product mixtures when irradiated at short (147 nm) and intermediate (220-260 nm) wavelength light. Photodecomposition products for the 220-260 nm include: methylacetylene, 1-butyne, and allene. Similar products were found after photolysis 147 nm along with an unidentified polymer.

When heated to decomposition it emits acrid smoke and fumes.

Melting Point-136.2 °C

물리화학적 성질

녹는점
-136.2 °C · -136.2°C
끓는 점
10.8 °C · 10.8 °C(lit.)
밀도
0.646 · 0.6460
굴절률
1.4205 · 1.4205
저장 조건
Freezer
물리적 상태
gas

안전 및 규제

GHS 분류

GHS Classification · 5건

Danger

H220 (89.3%): Extremely flammable gas [Danger Flammable gases];H224 (10.7%): Extremely flammable liquid and vapor [Danger Flammable liquids];H280 (100%): Contains gas under pressure; may explode if heated [Warning Gases under pressure];H411 (10.7%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P203, P210, P222, P233, P240, P241, P242, P243, P273, P280, P303+P361+P353, P370+P378, P377, P381, P391, P403, P403+P235, P410+P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 346 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

유해성 정보

Regulatory Information · 3건

Chemical: 1,2-Butadiene

1,2-Butadiene is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Butadiene 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: 12-08-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/1919

Fire PotentialA dangerous fire hazard.
Hazards SummaryPressurized liquid may cause frostbite. See health effects of 1,3-Butadiene, which causes CNS depression in high-dose animal studies. [HSDB] May cause irritation; [MSDSonline] See 1,3-Butadiene.
Special ReportsITC/USEPA; Information Review #479 (Draft) 1,2-Butadiene (1985)
Flammable Limits2%-12%
Hazard Classes and CategoriesFlam. Gas 1 (89.3%);Flam. Liq. 1 (10.7%);Press. Gas (Comp.) (100%);Aquatic Chronic 2 (10.7%)

안전 및 보호

Disposal Methods · 1건

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.

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 24(SRC), determined from a structure estimation method(2), indicates that 1,2-butadiene is expected to have very high mobility in soil(SRC). Volatilization of 1,2-butadiene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.097 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of 1,2-butadiene from dry soil surfaces may exist(SRC) based upon a vapor pressure of 1,260 mm Hg(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 24(SRC), determined from an estimation method(2), indicates that 1,2-butadiene 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 0.097 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1 and 70 hours, respectively(SRC). According to a classification scheme(5), an estimated BCF of 8(SRC), from an estimated log Kow of 2.06(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). No biodegradation data were located for 1,2-butadiene(SRC), but the biodegradation half-life of 1,3-butadiene in aerobic waters has been reported as 7 days and the half-life in anaerobic waters was reported as 28 days(8). These data suggest that 1,2-butadiene will also be biodegraded in aquatic systems(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2-butadiene, which has a vapor pressure of 1,260 mm Hg at 25 °C(2), is expected to exist solely as a gas in the ambient atmosphere. Gas-phase 1,2-butadiene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone molecules(SRC). The half-life for the reaction in air with hydroxyl radicals is estimated to be 15 hours(SRC), calculated from its rate constant of 2.6X10-11 cu cm/molecule-sec(3). The half-life for the reaction in air with ozone is estimated to be 12 days(SRC), calculated from its rate constant of 9.75X10-19 cu cm/molecule-sec(SRC), estimated with a structure estimation method(4). The gas phase reaction of 1,2-butadiene with nitrate radicals may be an important atmospheric removal process in urban areas at night(5), but the rate of this reaction is not known.

Adverse EffectsNeurotoxin - Acute solvent syndrome
Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 1,2-butadiene can be estimated to be 24(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,2-butadiene is expected to have very high mobility in soil(SRC).

Artificial Pollution Sources · 1건

1,2-Butadiene is a minor byproduct in the production of 1,3-butadiene. Consequently, the production and use of 1,3-butadiene in the manufacture of polymers such as synthetic rubber, plastics and resins may result in the release of 1,2-butadiene to the environment through various waste streams(1). There are no current commercial interests in 1,2-butadiene; however, there are a number of patents and publications regarding its recovery and application particularly in the specialty polymer area and as a gel inhibitor(1).

Environmental Biodegradation · 1건

No biodegradation data regarding 1,2-butadiene were located, however data on its structural isomer, 1,3-butadiene are available(1-4). Laboratory studies employing pure bacterial cultures isolated from lake and soil samples were shown to degrade 1,3-butadiene to 1,2-epoxybutene, however it is not clear what the rate of degradation is under environmental conditions(1-3). The biodegradation half-life of 1,3-butadiene in aerobic waters has been reported as 7 days and the half-life in anaerobic waters was reported as 28 days(4). These data suggest that 1,2-butadiene will also undergo biodegradation under similar conditions(SRC).

Environmental Bioconcentration · 1건

An estimated BCF of 8 was calculated for 1,2-butadiene(SRC), using an estimated log Kow of 2.06(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 (SRC).

규제 정보

Regulatory Information · 3건

Chemical: 1,2-Butadiene

1,2-Butadiene is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Butadiene 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: 12-08-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/1919

안전 데이터

wgk
1
tsca
TSCA listed
ridadr
UN 2037 2.1
risk_code
12
hazard_code
F+
safety_code
16-23-24/25

화학 및 산업

용도 및 제조

Uses · 5건

Used as a gel inhibitor in olefin polymerization, the primary feedstock for polybutadiene homopolymer, and a small by-product of 1,3-butadiene production; Occupational exposure may occur where 1,3-butadiene is produced or used. [HSDB]

Plastic Composites Manufacturing [Category: Industry]

Gel inhibitor in olefin polymerization.

1,2-Butadiene is the primary feedstock for polybutadiene homopolymer.

1,2-Butadiene is a small by-product in the production of 1,3-butadiene and has no significant current commercial interest. However, there are a number of publications and patents on its recovery and applications, particularly in the specialty polymer area and as a gel inhibitor.

U.S. Imports(1977): 1,000 to 11,000 lb
U.S. Production · 2건

2023: 850,000 - <1,000,000 lb;2022: 550,000 - <700,000 lb;2021: 10,000,000 - <50,000,000 lb;2020: 250,000 - <400,000 lb

One manufacturer in 1977 produced between 1 million to 10 million lb.

Consumer UsesIntermediate;Monomers
Industry UsesPolymerization promoter;Monomers;Intermediate
Methods of Manufacturing · 3건

1,2-Butadiene is prepared by vapor-phase isomerization of 2-butyne.

Eberly KC; Process for Preparing 1,2-Butadiene. Firestone Tire and Rubber Co. U.S. Patent No. 3,567,794 (1985). ... Dehydrochlorination of 2,3-dichloro-2-butene or 1,2-dichloro-2-butene or a mixture of both.

1,2-Butadiene is ... produced ... as a byproduct or an unisolated isomer in 1,3-butadiene production.

관련 반응

2건

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