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Home > Encyclopedia > (2E)-1,3-Dichloro-2-butene

(2E)-1,3-Dichloro-2-butene

(2E)-1,3-Dichloro-2-butene structure

(2E)-1,3-Dichloro-2-butene 

structure
  • CAS No:

    7415-31-8

  • Formula:

    C4H6Cl2

  • Chemical Name:

    (2E)-1,3-Dichloro-2-butene

  • Synonyms:

    2-Butene,1,3-dichloro-,(2E)-;2-Butene,1,3-dichloro-,(E)-;(2E)-1,3-Dichloro-2-butene;trans-1,3-Dichloro-2-butene;(E)-1,3-Dichloro-2-butene

Description

COLOURLESS-TO-YELLOW LIQUID WITH CHARACTERISTIC ODOUR.


COLOURLESS-TO-YELLOW LIQUID WITH CHARACTERISTIC ODOUR.

(2E)-1,3-Dichloro-2-butene Basic Attributes

124.992

125.00

616-055-4

PWG1E5MRLJ

1761

1993|2920

DTXSID7027338

CLEAR TO STRAW-COLORED LIQUID

Characteristics

0

2.84

COLOURLESS-TO-YELLOW LIQUID WITH CHARACTERISTIC ODOUR.

1.1585 g/cm3 @ Temp: 20 °C

-75°C

131 °C

27°C c.c.

Index of refraction: 1.4692 @ 20 °C/D

Solubility in water: reaction

Vapour pressure, kPa at 25°C: 1.33

Relative vapour density (air = 1): 4.3

vol% in air: 23

Safety Information

III

3

2920

Fireproof. Ventilation along the floor. Well closed. Separated from strong oxidants and food and feedstuffs. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P310, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501

H226

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.

A REVIEW WITH 17 REFERENCES ON TOXICITY OF CHLOROPRENE, 1,3-DICHLORO-2-BUTENE & 1,4-DICHLORO-BUTENE.[CLARY JJ; TOXICITY OF CHLOROPRENE, 1,3-DICHLORO-2-BUTENE, & 1,4-DICHLORO-2-BUTENE; ENVIRON HEALTH PERSPECT 21: 269 (1977)]

Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 27 °C explosive vapour/air mixtures may be formed.|Flammable - 3rd degree, Reactive - 2nd degree

|Danger|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P310, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 44 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. /Dichlorobutene/

FIRE HAZARD: DANGEROUS, WHEN EXPOSED TO HEAT OR FLAME.

Explosive limits , vol% in air: 2-13

FOAM, CARBON DIOXIDE, DRY CHEMICAL...|If material on fire or involved in fire: Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use foam, dry chemical, or carbon dioxide. Use water spray to knock-down vapors. /Dichlorobutene/

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Dichlorobutene/|Personnel protection: Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. If contact with the material anticipated, wear appropriate chemical protective clothing. /Dichlorobutene/

Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Fireproof. Ventilation along the floor. Well closed. Separated from strong oxidants and food and feedstuffs. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.

The vapour is irritating to the respiratory tract and eyes. The substance is severely irritating to the eyes. The substance is corrosive to the skin.

Repeated or prolonged inhalation of high concentrations may cause effects on the lungs.

NO open flames, NO sparks and NO smoking. Above 27 °C use a closed system and ventilation.

STRICT HYGIENE!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Dichlorobutene (isomer not specified) was detected in 1 of 63 industrial effluents (concn of 10-100 ug/L) collected from a wide range of chemical manufacturers across the US(1).

Toxicity

1,3-Dichloro-2-butene's occurrence as a by-product in the production of chloroprene(1) may release the compound to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 125(SRC), determined from a structure estimation method(2), indicates that 1,3-dichloro-2-butene is expected to have high mobility in soil(SRC). Volatilization of 1,3-dichloro-2-butene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.8X10-2 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of 1,3-dichloro-2-butene from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 12.6 mm Hg(SRC), determined from a fragment constant method(4). The neutral hydrolysis half-life of a structurally similar compound, 1,4-dichloro-2-butene has been measured as 3.2 days(5). This suggests that 1,3-dichloro-2-butene may also undergo hydrolysis in moist soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 125(SRC), determined from a structure estimation method(2), indicates that 1,3-dichloro-2-butene is not 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 3.8X10-2 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 hour and 4.4 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 30(SRC), from an estimated log Kow of 2.84(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. The neutral hydrolysis half-life of a structurally similar compound, 1,4-dichloro-2-butene has been measured as 3.2 days(8). This suggests that 1,3-dichloro-2-butene may also undergo hydrolysis in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3-dichloro-2-butene, which has an estimated vapor pressure of 12.6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,3-dichloro-2-butene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone(SRC). The half-life for the reaction in air with hydroxyl radicals is estimated to be 27 hours(SRC), calculated from its rate constant of 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). The half-life for the reaction in air with ozone is estimated to be 8 days(SRC), calculated from its rate constants of 1.4X10-18 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

The rate constant for the vapor-phase reaction of 1,3-dichloro-2-butene with photochemically-produced hydroxyl radicals has been estimated as 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 27 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 1,3-dichloro-2-butene with ozone has been estimated as 1.4X10-18 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 8 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). The neutral hydrolysis half-life of a similar compound, 1,4-dichloro-2-butene has been measured as 3.2 days(3). This suggests that 1,3-dichloro-2-butene may also undergo hydrolysis in the environment(SRC).

An estimated BCF of 30 was calculated for 1,3-dichloro-2-butene(SRC), using an estimated log Kow of 2.84(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.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 1,3-dichloro-2-butene can be estimated to be 125(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,3-dichloro-2-butene is expected to have high mobility in soil.

The Henry's Law constant for 1,3-dichloro-2-butene is estimated as 3.8X10-2 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1,3-dichloro-2-butene 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 4.4 days(SRC). 1,3-Dichloro-2-butene's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of 1,3-dichloro-2-butene from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 12.6 mm Hg(SRC), determined from a fragment constant method(3).

SURFACE WATER: Dichlorobutene (isomer not specified) was qualitatively detected in raw water collected from the Mississippi River in 1970 in LA(1).

Occupational exposure to 1,3-dichloro-2-butene may occur through inhalation and dermal contact with this compound at workplaces where 1,3-dichloro-2-butene is produced or used. (SRC)

Drug Information

Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer immediately for medical attention.


Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.

Stabilization: Treatment is largely supportive. Watch for respiratory depression & arrhythmias. Obtain arterial blood gases. Administer oxygen if there is evidence of altered mental status or dyspnea. Treat hypotension with volume expansion & vasopression. Use lidocaine or beta-blockers for ventricular arrhythmias. Skin: Remove contaminated clothing. Wash affected area with soap & copious amounts or water. Eye: Irrigate the eye for 15-20 min. Obtain a consultation if symptoms persist. Oral: Most of the halogenated solvents ingested in quantities of 1-2 swallows may be partially removed by ipecac-induced emesis if admin within a few hr to a patient who has not lost the gag reflex, is not seizing, is not markedly lethargic, or is not in coma. Observe the patient in the upright position to lessen the possibility of aspiration. Activated charcoal is probably ineffective. Inhalation: Move from the contaminated area. Provide a source of oxygen & prepare for mechanical ventilation. If the patient is unconscious & the pulse is absent, initiate CPR measures. Enhancement of Elimination: Maintain good ventilation. Hemodialysis or hemoperfusion are not likely to be useful because of the high lipophilic properties of these solvents. Antidote: N-acetylcysteine may restore depleted glutathione stores, but no adequate clinical studies are available to validate this possible treatment. Supportive Care: Watch for cardiac dysrhythmias, aspiration pneumonitis, hepatotoxicity, & hypoxic encephalopathy. Monitor for arrhythmia for at least 24 hr & for hepatorenal failure for about 3 days. Obtain a chest x-ray, arterial blood gas, EKG, serum creatinine, & hepatic aminotransferase. Check electrolyte imbalance daily. Treat renal failure with dialysis & hepatic failure with fresh frozen plasma, vitamin K, a low-protein diet, neomycin, & lactulose. Watch fluid & electrolyte balance. /Halogenated hydrocarbons/

Symptomatology: 1A) Inhalation, high vapor concn: gasping, refusal to breathe, coughing, substernal pain, & extreme respiratory distress at vapor concn over 1500 ppm. Irritation of eyes & upper respiratory mucosa appears promptly after exposure to concentrated vapors. Lacrimation & headache are prominent. Coma may occur rapidly. B) Inhalation, low vapor concn: central nervous depression & moderate irritation of respiratory system. Headache is frequent. 2) Dermal: severe skin irritation with marked inflammatory response of epidermis & underlying tissues. 3) Oral: acute gastrointestinal distress with pulmonary congestion & edema. Central nervous depression, perhaps even in the absence of impaired oxygen uptake. 4) By any route, possible late injuries to liver, kidneys & heart. 5) After inhalation exposures, malaise, headache, chest & abdominal discomfort & irritability have been reported to persist for several weeks & perhaps for several years.

1,3-dichloro-2-butene

The substance can be absorbed into the body in hazardous amounts by inhalation of its vapour, through the skin and by ingestion. Serious local effects by all routes of exposure.

Cough. Sore throat.


Redness. Pain. Skin burns.


Redness. Pain.

(2E)-1,3-Dichloro-2-butene Use and Manufacturing

Methods of Manufacturing

Reaction of 2-chloro-1,3-butadiene with HCl in the presence of a copper chloride catalyst.

Uses

Intermediates

Production

1-10 million lbs by DuPont in Louisville, KY (1977)

95%, mixture of cis and trans isomers

All other basic organic chemical manufacturing|2-Butene, 1,3-dichloro-: ACTIVE|Occurs in high boilers and still heels from chloroprene refining

EAD Method 1624. Volatile Organic Coumpounds by Isotope Diltuion GCMS, 1600 Series Wastewater Methods, EPA Engineering and Analysis Div. GC/MS detection limit 50 ug/L /1,4-dichloro-2-butene/

Fire Hazards -> Flammable - 3rd degree, Reactive - 2nd degree

Computed Properties

Molecular Weight:124.99
XLogP3:2.1
Rotatable Bond Count:1
Exact Mass:123.9846556
Monoisotopic Mass:123.9846556
Heavy Atom Count:6
Complexity:56.6
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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