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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 42
実験および物理化学的性質
Polymers
Plastics & Rubber -> Other Monomers
Plastics & Rubber -> Other Monomers
LogP
log Kow= 2.44
log Kow= 2.44
1.5 (estimated)
2.44
Density
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
Colorless liquid
Colorless liquid
Solubility
SOL IN ALL PROP IN ALC, ETHER, ACETONE, BENZENE, HEPTANE, & CARBON TETRACHLORIDE
MISCIBLE WITH ALCOHOL, ETHER, ACETONE, BENZENE
Water solubility of >341 mg/l at room temperature.
Solubility in water, g/100ml: 0.069 (very poor)
Flash Point
-20 °F (USCG, 1999)
-29 °C (CLOSED CUP)
-28 °C c.c.
Boiling Point
109 °F at 760 mmHg (NFPA, 2010)
42 °C
42 °C
Melting Point
-222 °F (USCG, 1999)
-87.5 °C
-87 °C
Vapor Density
2.35 (AIR= 1)
Relative vapor density (air = 1): 2.35
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.)
- 闪点
- 30 °F · <−30 °F
- 貯蔵温度
- 2 · 2-8°C
- 外見
- clear liquid
- 色
- Colorless to Almost colorless
- 比重
- 0.6764 · 0.6764
- BRN
- 1523659 · 1523659
- Henry's Law Constant
- 1 · 1.0×10-4 mol/(m3Pa) at 25℃, Yaws (2003)
- Dielectric constant
- 2.32 · 2.3199999999999998
- 安定性
- 安定。とても燃えやすい。空気と爆発性混合物を容易に形成します。低い引火点に注意してください。強力な酸化剤とは相容れない。
- InChI
- 1S/C5H8/c1-3-5-4-2/h3-5H,1H2,2H3/b5-4+
- InChIKey
- PMJHHCWVYXUKFD-SNAWJCMRSA-N
- SMILES
- C\C=C\C=C
- CAS データベース
- 2004 · 2004-70-8(CAS DataBase Reference)
- EPAの化学物質情報
- 1 · 1,3-Pentadiene, (3E)- (2004-70-8)
安全と法規制
GHS分類
GHS Classification
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
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.
Fire Hazards
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
HIGHLY FLAMMABLE, DANGEROUS FIRE RISK.
A very dangerous fire and explosion hazard when exposed to heat or flame; can react vigorously with oxidizing materials.
Hazards Summary
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]
RCRA Requirements
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).
Reactivity Profile
1,3-PENTADIENE 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. May undergo autoxidation upon exposure to the air to form explosive peroxides. Violent explosions at low temperatures in ammonia synthesis units have been traced to the addition products of dienes and nitrogen dioxide [Bretherick, 5th Ed., 1995].
安全と保護具
Fire Fighting
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
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.
Disposal Methods
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U186, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.
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.
Spillage Disposal
Remove all ignition sources. Evacuate danger area! Consult an expert! Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Collect leaking liquid in covered containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer.
毒性情報
Environmental Fate
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
Neurotoxin - Acute solvent syndrome
Neurotoxin - Acute solvent syndrome
Signs and Symptoms
Redness.
Redness.
Nausea. Vomiting. Aspiration hazard!
Effluent Concentrations
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
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).
Natural Pollution Sources
1,3-Pentadiene may be released to the atmosphere during the combustion of biomass during fires caused by lightning, volcanoes, or other natural phenomena(1).
trans-1,3-Pentadiene may be released to the atmosphere during the combustion of biomass during fires caused by lightning, volcanoes, or other natural phenomena(1).
Artificial Pollution Sources
1,3-Pentadiene's production and use as a co-monomer in the manufacture of polymers, maleic anhydride and as a chemical intermediate(1) may result in its release to the environment through various waste streams(SRC). It may also be released to the environment from waste incinerators and in the exhaust of motor vehicles(2,3).
trans-1,3-Pentadiene's production and use in polymers, maleic anhydride adducts, and as an intermediate(1) may result in its release to the environment through various waste streams(SRC). trans-1,3-Pentadiene may also be released to the atmosphere in the exhaust of motor vehicles(2).
Environmental Biodegradation
No biodegradation data regarding 1,3-pentadiene were located(SRC), however data on a similar compound, 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 will be 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 1,3-pentadiene will also undergo biodegradation under similar conditions(SRC).
Environmental Bioconcentration
An estimated BCF of 15 was calculated for 1,3-pentadiene(SRC), using a log Kow of 2.44(1) 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).
An estimated BCF of 15 was calculated for trans-1,3-pentadiene(SRC), using a log Kow of 2.44(1) 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).
Volatilization from Water/Soil
The Henry's Law constant for 1,3-pentadiene is estimated as 0.069 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1,3-pentadiene is expected to volatilize rapidly from water surfaces(2). 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)(2) is estimated as 1 hour(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 78 hours(SRC). 1,3-Pentadiene's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of 1,3-pentadiene from dry soil surfaces exists based upon a vapor pressure of 405 mm Hg(3).
The Henry's Law constant for trans-1,3-pentadiene is estimated as 0.12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that trans-1,3-pentadiene is expected to volatilize rapidly from water surfaces(2). 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)(2) is estimated as 51 min(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 3.3 days(SRC). trans-1,3-Pentadiene's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of trans-1,3-pentadiene from dry soil surfaces may exist based upon a vapor pressure of 411 mm Hg(3).
法規制情報
RCRA Requirements
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
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)
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
- risk_code
- 11-65-36/37/38
- 化審法
- (2)-20
- 消防法
- 危-4-1-II
- hazard_code
- F,Xn
- safety_code
- 16-23-26-36-62
- hazard_class
- 3.1
- packing_group
- I
- Hazard Classifications
- Asp. Tox. 1Eye Irrit. 2Flam. Liq. 2Skin Irrit. 2STOT SE 3
- ストレージクラス
- 3 - Flammable liquids
- 有毒物質データの
- 2004-70-8(Hazardous Substances Data)
化学と産業
用途と製造
Uses
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
U.S. Production
2023: 2,500,000 - <4,000,000 lb
2023: 54,196,074 lb
(1988) 123 million lb
Consumer Uses
Not Known or Reasonably Ascertainable
Other
Industry Uses
Fuel
Other
Methods of Manufacturing
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.
General Manufacturing Information
Petrochemical Manufacturing
Plastics Material and Resin Manufacturing
1,3-Pentadiene: ACTIVE
1,3-Pentadiene, (3E)-: ACTIVE
Mixture of cis + trans isomers
応用分野
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.]
上流・下流製品情報
上流原料
下流製品
サプライヤー41 社
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
関連ノート
読み込み中…