1,3-Pentadiene

HCID 62204CAS 2004-70-8

基本情報

標準SMILES
C=C/C=C/C
InChIKey
PMJHHCWVYXUKFD-SNAWJCMRSA-N
分子式
C5H8
平均分子量
68.12 g/mol
単同位体質量
68.06260026

概要

1,3-pentadiene appears as a clear colorless liquid with an acrid odor. A dangerous fire risk. Vapors are irritating to the eyes and respiratory system. Subject to polymerization if heated or contaminated. If the polymerization takes place inside a container, the container may violently rupture. Insoluble in water. Used to make intermediates and polymers.

名称と識別子

優先名称
1,3-Pentadiene
IUPAC
(3E)-penta-1,3-diene
現地名
trans-1,3-ペンタジエン
英語名
trans-1,3-Pentadiene
分子式
C5H8
分子量
68.12

名称と別名

1,3-PENTADIENEPiperylene504-60-91-MethylbutadieneFW963NF88B1-methyl-1,3-butadieneDTXSID3027160RefChem:906913DTXCID00809454207-995-2trans-1,3-Pentadienetrans-Piperylene
名称をさらに表示
trans-1,3-ペンタジエン(E)-1,3-ペンタジエンtrans-ピペリレン(3E)-1,3-ペンタジエン1,3t-ペンタジエンtrans1,3ペンタジエンtrans-1.3-ペンタジエン(e)-3-pentadiene(E)-CH2=CHCH=CHCH31,trans-3-Pentadiene
2004-70-8(3E)-penta-1,3-diene(E)-1,3-Pentadiene1,3-Pentadiene, (3E)-trans-1-Methylbutadiene(3E)-1,3-Pentadienetrans-Penta-1,3-dieneRCRA waste number U186

データベース識別子

CAS
2004-70-8、41050-31-1、504-60-9、68308-15-6
PubChem CID
62204
DTXSID
DTXSID50858710
ChEBI
CHEBI:74165
UNII
00OA1GPF8R
EC Number
207-995-2、217-909-5
Nikkaji
J43.494I、J6.219G

物性

構造計算による物性

XLogP
2.4
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
1
重原子数
5

実験および物理化学的性質

Chemical ClassesFlammable agents - 3rd degree
Polymers · 2 件

Plastics & Rubber -> Other Monomers

Plastics & Rubber -> Other Monomers

SpringerMaterials PropertiesBoiling point
LogP · 4 件

log Kow= 2.44

log Kow= 2.44

1.5 (estimated)

2.44

Density · 5 件

0.6834 at 68 °F (average value for cis and trans isomers) (USCG, 1999) - Less dense than water; will float

0.6760 @ 20 °C/4 °C

0.6710 g/ml @ 25 °C

0.7 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.7

Color/Form · 2 件

Colorless liquid

Colorless liquid

物理化学的性質

融点
-87 °C · -87 °C (lit.)
沸点
42 °C · 42 °C (lit.)
比重(密度)
0.678 g/mL · 0.678 g/mL at 20 °C 0.683 g/mL at 25 °C (lit.)
蒸気密度
2.4 · 2.4 (vs air)
蒸気圧
6.56 psi · 6.56 psi ( 20 °C)
屈折率
20 · n20/D 1.433(lit.)

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 5.1% (13 of 256) of reports.

Danger

H225 (94.9%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P280, P301+P316, P303+P361+P353, P331, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 256 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

危険有害性情報

Regulatory Information · 6 件

Chemical: 1,3-Pentadiene

Chemical: 1,3-Pentadiene, (E)-

1,3-Pentadiene is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Pentadiene 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)

1,3-Pentadiene, (3E)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Pentadiene, (3E)- 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: No longer Valid Update: 30-10-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/1772

1,3-Pentadiene: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

DOT LabelFlammable Liquid
Fire Hazards · 2 件

Special Hazards of Combustion Products: Fire produces irritating and poisonous gases.

Highly flammable. Vapour/air mixtures are explosive. Heating will cause rise in pressure with risk of bursting.

Fire Potential · 2 件

HIGHLY FLAMMABLE, DANGEROUS FIRE RISK.

A very dangerous fire and explosion hazard when exposed to heat or flame; can react vigorously with oxidizing materials.

Health HazardsVapors may cause dizziness or suffocation; contact may irritate skin and eyes. (USCG, 1999)
Hazards Summary · 2 件

A skin and eye irritant; Inhaled at high concentrations, it may act as a simple asphyxiant; [NJ-HSFS] Causes somnolence and ataxia in lethal-dose inhalation studies of rodents; [RTECS] See trans-1,3-Pentadiene.

In lethal concentration studies, rats have somnolence, ataxia, and dyspnea; [RTECS] May cause moderate skin irritation on prolonged contact, based on animal studies; [CHEMINFO] An irritant; [MSDSonline]

安全と保護具

Fire Fighting · 2 件

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

Use water spray, foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

Fresh air, rest. Seek medical attention if you feel unwell.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention if skin irritation occurs.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth. Do NOT induce vomiting. Seek medical attention if you feel unwell.

First AidINHALATION: Move victim to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Safe StorageSeparated from strong oxidants. Fireproof. Store in an area without drain or sewer access. Ventilation along the floor.
Fire Fighting ProceduresWATER MAY BE EFFECTIVE.
Nonfire Spill ResponseExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

毒性情報

Environmental Fate · 6 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 500(SRC), determined from a log Kow of 2.44(2) and a regression-derived equation(3), indicates that 1,3-pentadiene is expected to have low mobility in soil(SRC). Volatilization of 1,3-pentadiene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.069 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of 1,3-pentadiene from dry soil surfaces may exist based upon a vapor pressure of 405 mm Hg(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 500(SRC), determined from a log Kow of 2.44(2) and a regression-derived equation(3), indicates that 1,3-pentadiene is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected to be an important fate process(3) based upon an estimated Henry's Law constant of 0.069 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 78 hrs, respectively(SRC). According to a classification scheme(5), an estimated BCF of 15(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low. No biodegradation data were located for 1,3-pentadiene(SRC), but the biodegradation half-life of 1,3-butadiene has been reported as 7 days in aerobic water and 28 days in anaerobic water(7). These data suggest that 1,3-pentadiene 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), 1,3-pentadiene, which has a vapor pressure of 405 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,3-pentadiene 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 3.7 hours(SRC), calculated from its rate constant of 1.01X10-10 cu cm/molecule-sec at 24 °C(3). The half-life for the reaction in air with ozone is estimated to be 5 hours(SRC), calculated from its rate constant of 5.26X10-17 cu cm/molecule-sec(SRC), estimated with a structure estimation method(4). The vapor phase reaction of 1,3-pentadiene 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.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 500(SRC), determined from a measured log Kow of 2.44(2) and a regression-derived equation(3), indicates that trans-1,3-pentadiene is expected to have low mobility in soil(SRC). Volatilization of trans-1,3-pentadiene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.12 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of trans-1,3-pentadiene from dry soil surfaces may exist(SRC) based upon a vapor pressure of 411 mm Hg(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 500(SRC), determined from a measured log Kow of 2.44(2) and a regression-derived equation(3), indicates that trans-1,3-pentadiene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 0.12 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 51 min and 78 hours, respectively(SRC). According to a classification scheme(5), an estimated BCF of 15(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trans-1,3-pentadiene, which has a vapor pressure of 411 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase trans-1,3-pentadiene 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 3.7 hours(SRC), calculated from its rate constant of 1.05X10-10 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Vapor-phase trans-1,3-pentadiene is also degraded in the atmosphere by reaction with photochemically-produced ozone(SRC); the half-life for this reaction in air is estimated to be 5.2 hours(SRC), calculated from its rate constant of 5.26X10-17 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). In general, the night time degradation of conjugated diolefins by the gas-phase reaction with nitrate radicals may be important in urban areas or in heavily polluted atmospheres(4), and this may be an important removal process for trans-1,3-pentadiene(SRC).

Adverse Effects · 2 件

Neurotoxin - Acute solvent syndrome

Neurotoxin - Acute solvent syndrome

Exposure RoutesThe substance can be absorbed into the body by inhalation.
Signs and Symptoms · 3 件

Redness.

Redness.

Nausea. Vomiting. Aspiration hazard!

Effluent Concentrations · 2 件

1,3-Pentadiene was identified, not quantified, as a stack emission from waste incinerators(1). 1,3-Pentadiene has been identified, not quantified, in the exhaust of gasoline and diesel engines(2). 1,3-Pentadiene was detected in the exhaust of a single component fuel at a concn of 0.66 ppm(3). 1,3-Pentadiene was identified, not quantified, in the volatile emissions of garden waste(4).

trans-1,3-Pentadiene has been qualitatively detected in the exhaust of gasoline and diesel engines(1).

Soil Adsorption/Mobility · 2 件

The Koc of 1,3-pentadiene is estimated as 500(SRC), using a log Kow of 2.44(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1,3-pentadiene is expected to have low mobility in soil(SRC).

The Koc of trans-1,3-pentadiene is estimated as 500(SRC), using a measured log Kow of 2.44(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that trans-1,3-pentadiene is expected to have low mobility in soil(SRC).

法規制情報

RCRA Requirements · 1 件

U186; As stipulated in 40 CFR 261.33, when 1,3-pentadiene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

CERCLA Reportable Quantities · 1 件

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

DHS Chemicals of Interest (COI) · 4 件

1,3-Pentadiene

1

10000

Flammable chemical that can be released at a facility.

安全データ

wgk
3
tsca
TSCA listed
rtecs
RZ2465000
ridadr
UN 3295 3/PG 2
毒性
LD50 ivn-mus: 18 mg/kg CSLNX* NX#04179
hs_code
2901.29.5000

化学と産業

用途と製造

Uses · 4 件

Used as an intermediate and co-monomer in production of polymers and other organic chemicals; [Hawley]

A product of combustion; Used to make polymers and other chemicals; [HSDB]

/co-monomer in production of/ polymers, maleic anhydride adducts; intermediate.

Polymers, maleic anhydride adducts; intermediate

ImpuritiesCyclopentene
U.S. Production · 3 件

2023: 2,500,000 - <4,000,000 lb

2023: 54,196,074 lb

(1988) 123 million lb

Consumer Uses · 2 件

Not Known or Reasonably Ascertainable

Other

Industry Uses · 2 件

Fuel

Other

Methods of Manufacturing · 2 件

The methylation of butadiene with dimethyl sulfoxide in the presence of a base, such as potassium t-butoxide, produces 1,3-pentadiene (80% trans, 20% cis)

The methylation of butadiene with dimethyl sulfoxide in the presence of a base such as potassium t-butoxide.

応用分野 · 1 件

一般的な説明Trans-1,3-Pentadiene spectra is recorded in the 5000-17500 cm(-1) region with conventional and intracavity laser photoacoustic spectroscopy. It can be determined by the spectrophotometric method based on the Diels-Alder reaction. In this reaction, cisoid 1,3-dienes and tetracyanoethylene (TCNE) react with an aromatic-TCNE pi-complex.

調製方法

純化方法Distil the diene from NaBH4. Purify it also by preparative gas chromatography. [Reimann et al. J Am Chem Soc 108 5527 1986, Beilstein 1 IV 994.]

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補足説明

定義ChEBI: An alkadiene consisting of pentane with the two double bonds located at positions 1 and 3.

関連反応

6 件

関連ノート

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