1,4-Dichloro-2-butene

125

125.00

203-779-7

2920

DTXSID9027310

Colorless liquid

0 Ų

1.97

1,4-dichloro-2-butene appears as a clear colorless liquid. Burns, though may be difficult to ignite. Corrosive to tissue. Denser than water and insoluble in water. Vapors heavier than air. Used to make other chemicals.

1.1858 g/cm³

3.5 °C

158 °C

129 °F

1.459

Miscible with benzene, alc, carbon tetrachloride; immiscible with ethylene glycol and glycerol.

2-8°C

10 mm Hg ( 20 °C)

Oral-Rat LD50: 89 mg/kg; Oral-Mouse LD50: 190 mg/kg

Inflammable in case of fire, high temperature and oxidant; decomposes toxic chloride gas with high heat

Sweet, pungent

Heat of combustion: -17,500 Btu/lb = -9,720 cal/g = -407x10+5 J/kg /Dichlorobutene/|Heat of vaporization: 130 Btu = 73 cal/g = 3.1x10+5 J/kg /Dichlorobutene/

Highly flammable. Reacts slowly with water to form hydrochloric acid. Insoluble in water.

Halogenated Organic Compounds

Highly Flammable

Halogenated unsaturated aliphatic compounds, such as 1,4-DICHLORO-2-BUTENE, are moderately or very reactive. Halogenated organics generally become less reactive as more of their hydrogen atoms are replaced with halogen atoms. Low molecular weight haloalkanes are highly flammable and can react with some metals to form dangerous products. Materials in this group are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.

1.5-4.0% /Dichlorobutene/

Corrodes metal when wet. /Dichlorobutene/

II

6.1(a)

UN 3390 6.1/PG 1

3

10-21-25-26-34-50/53-24/25-45

53-23-26-36/37/39-45-61-60-99

EM4903000

T+,N

The warehouse is ventilated, low temperature and dry; stored separately from oxidants and acids

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U074, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

/Dichlorobutene/ reacts slowly with water to form hydrochloric acid. /Dichlorobutene/

A REVIEW WITH 17 REFERENCES ON ACUTE TOXICITY OF CHLOROPRENE, 1,3-DICHLORO-2-BUTENE, & 1,4-DICHLORO-2-BUTENE. DATA INCL MUTAGENIC, SKIN, EYE & INHALATION TESTING, LETHAL, & TERATOGENIC DOSE VALUES.[CLARY JJ; ENVIRON HEALTH PERSPECT 21: 269-74 (1977)]

Special Hazards of Combustion Products: Decomposition vapors contain phosgene and hydrogen chloride gases; both are toxic and irritating. (USCG, 1999)

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P264, P270, P271, P273, P280, P281, P284, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|H226 (34.23%): Flammable liquid and vapor [Warning Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P273, P280, P281, P284, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P320, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 111 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H226: Flammable liquid and vapor [Warning Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P281, P284, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P312, P314, P320, P321, P322, P330, P361, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: Fully encapsulating, vapor-protective clothing should be worn for spills and leaks with no fire. ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb with earth, sand or other non-combustible material and transfer to containers (except for Hydrazine). Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Rubber gloves; chemical splash goggles; rubber boots and apron; barrier cream; organic canister mask. (USCG, 1999)|Rubber gloves; chemical splash goggles; rubber boots & apron; barrier cream; organic canister mask. /Dichlorobutene/|Penetration rate for neoprene, or PVC on cotton, ranged between 27-38 ug/min x sq cm. While the rate for NBR rubber was 156 ug/min x sq cm.|Chemical protective clothing composed of polyvinyl alcohol (PVA), Viton (a proprietary fluoroelastomer), or Saranex (a multilayer laminate greater than 0.15 cm in thickness of polyethylene and Saran) is highly recommended, having break through times greater than one hour. Butyl rubber or polyethylene may be used but data suggests break through times of approximately an hour or more. Protective clothing composed of natural rubber, nitrile, chlorinated polyethylene, or polyvinyl chloride (material less than 0.015 cm thick) is not recommended since break through times were found to be significantly less than one hour.|Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. /Dichlorobutene/

Vapor may explode if ignited in an enclosed area. /Dichlorobutene/

When fighting fires wear goggles and self-contained breathing apparatus. Extinguish with water, dry chemicals, foam, or carbon dioxide. /Dichlorobutene/|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/

If fire becomes uncontrollable or container is exposed to direct flame- evacuate for a radius of 1500 ft. If material leaking (not on fire), downwind evacuation must be considered. /Dichlorobutene, flammable liquid, corrosive/

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/

... BOTH LIQ AND VAPOR ARE HIGHLY DANGEROUS TO THE SKIN, EYES, LUNG, & INTERNAL ORGANS.|Inhalation of vapor irritates nose and throat. Contact with eyes causes intense irritation.

U074; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.

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 1 lb or .454 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).

U074; As stipulated in 40 CFR 261.33, when 1,4-dichloro-2-butene, 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).

highly toxic

LC50 Rat Inhalation 86 ppm/4 hr.|LD50 Rat oral 89 mg/kg|LD50 Mouse oral 190 mg/kg|LD50 Mouse iv 56 mg/kg|LD50 Rabbit skin 620 mg/kg

1,4-Dichloro-2-butene's production and use as a starting material in the manufacture of adiponitrile, butane-1,4-diol and tetrahydrofuran(1) may result in its release to the environment through various waste streams (SRC). It also occurs as an intermediate in the production of chloroprene(1).

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 215(2) indicates that 1,4-dichloro-2-butene is expected to have moderate mobility in soil(SRC). Volatilization of 1,4-dichloro-2-butene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.8X10-4 atm-cu m/mole(SRC), based upon its vapor pressure, 3 mm Hg(3), and water solubility, 580 mg/l(3). The potential for volatilization of 1,4-dichloro-2-butene from dry soil surfaces may exist(SRC) based upon its vapor pressure(3). In a soil degradation study, approximately 5-15% of initially added 1,4-dichloro-2-butene was recovered in gas-traps after a 7-day period indicating soil volatilization had occurred(2). Soil degradation studies conducted over a week incubation period in a sandy loam and silt loam soils found degradation half-lives of 1.8 to 2.5 days in both sterile and non-sterile soils(2); degradation rates in non-sterile soils were not significantly faster than in sterile soils indicating that abiotic or evaporative processes were more important than biological processes for 1,4-dichloro-2-butene (cis-isomer)(2,4). The hydrolysis half-life of 1,4-dichloro-2-butene was measured as 3.2 days under neutral conditions(5), suggesting hydrolysis may be an important fate process in moist soils.|AQUATIC FATE: Based on a classification scheme(1), a Koc value of 215(SRC), indicates that 1,4-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 5.8X10-4 atm-cu m/mole(SRC), based upon its vapor pressure, 3 mm Hg(4), and water solubility, 580 mg/l(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 hours and 5 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 14(SRC), from its water solubility(4) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low. The hydrolysis half-life of 1,4-dichloro-2-butene was measured as 3.2 days under neutral conditions(6). Limited soil data suggest that biodegradation will not be an important fate process in water since volatilization and hydrolysis are expected to occur rapidly(2,7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,4-dichloro-2-butene, which has a vapor pressure of 3 mm Hg at 25 °C(1) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,4-dichloro-2-butene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone molecules(SRC). The half-life for the reaction in air is estimated to be 12 hours for the cis isomer and about 10 hours for the trans isomer(SRC), calculated from its rate constants of 3.3X10-11 cu cm/molecule-sec and 3.7X10-11 cu cm/molecule-sec at 25 °C(SRC) for the cis and trans isomers, respectively, using a structure estimation method(3). The half-life for the reaction with ozone is estimated to be 16 days for the cis isomer and about 8 days for the trans isomer(SRC), calculated from its rate constants of 7.1X10-19 cu cm/molecule-sec and 1.4X10-18 cu cm/molecule-sec at 25 °C(SRC) for the cis and trans isomers, respectively, using a structure estimation method(3).

The rate constant for the vapor-phase reaction of 1,4-dichloro-2-butene with photochemically-produced hydroxyl radicals has been estimated as 3.3X10-11 cu cm/molecule-sec and 3.7X10-11 cu cm/molecule-sec at 25 °C(SRC) for the cis and trans isomers, respectively, using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12 hours for the cis isomer and about 10 hours for the trans isomer at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 1,4-dichloro-2-butene with ozone has been estimated as 7.1X10-19 cu cm/molecule-sec and 1.4X10-18 cu cm/molecule-sec at 25 °C(SRC) for the cis and trans isomers, respectively, using a structure estimation method(1). This corresponds to an atmospheric half-life of about 16 days for the cis isomer and about 8 days for the trans isomer at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). The neutral hydrolysis rate constant of 1,4-dichloro-2-butene (cis- and trans-isomers) have been experimentally determined to be 0.009 to 0.0091/hr at 25 °C which corresponds to a half-life of 3.2 days(3).

An estimated BCF of 17 was calculated for 1,4-dichloro-2-butene(SRC), using a water solubility of 580 mg/l(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).

Using sandy loam and silt loam soils, the Koc of 1,4-dichloro-2-butene (cis-isomer) was experimental determined to be 215(1). According to a classification scheme(2), this Koc value suggests that 1,4-dichloro-2-butene has moderate mobility in soil(SRC).

The Henry's Law constant for 1,4-dichloro-2-butene is estimated as 5.8X10-4 atm-cu m/mole(SRC) based upon its vapor pressure, 3 mm Hg(1), and water solubility, 580 mg/l(1). This Henry's Law constant indicates that 1,4-dichloro-2-butene is expected to volatilize 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 2 hours(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 5 days(SRC). 1,4-Dichloro-2-butene's estimated Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of 1,4-dichloro-2-butene from dry soil surfaces may exist(SRC) based upon the vapor pressure of this compound(1). In a soil degradation study, approximately 5-15% of initially added 1,4-dichloro-2-butene (cis-isomer) was recovered in gas-traps after a 7-day period indicating soil volatilization(3).

Occupational exposure to 1,4-dichloro-2-butene may occur through inhalation and dermal contact with this compound at workplaces where 1,4-dichloro-2-butene is produced or used. (SRC)

AN OXIDATION OF THE DOUBLE BOND IN CERTAIN HALO-OLEFINS, WHICH IS DEPENDENT ON MICROSOMAL MONO-OXYGENASES PROBABLY IS A COMMON PATHWAY IN THE FORMATION OF BIOLOGICALLY REACTIVE INTERMEDIATES.

Inhalation of vapor irritates nose and throat. Contact with eyes causes intense irritation and tears. Contact of liquid with skin causes severe blistering and dermatitis. Ingestion causes severe irritation of mouth and stomach. (USCG, 1999)

INHALATION: remove from exposure; provide low-pressure oxygen if required; keep under observation until edema is ruled out. EYES: irrigate immediately for 15 min.; call physician. SKIN: wash immediately and thoroughly with soap and water; treat as a chemical burn. INGESTION: induce vomiting; call physician. (USCG, 1999)

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/

PROTRACTED CONTACT WITH SKIN CAUSES DERMATITIS AND BLISTERING. HIGH CONCN OF VAPOR APPARENTLY HAVE DELAYED TOXIC EFFECT ON EYES, CAUSING ONSET OF IRRITATION AND LACRIMATION SEVERAL HR AFTER THE EXPOSURE, SEEMING SIMILAR TO DIMETHYL SULFATE AND OTHER ALKYLATING AGENTS IN MODE OF ACTION.|IRRITANT TO SKIN ... CAUSES BLISTERS.|HIGH CONCN OF VAPOR APPARENTLY HAVE DELAYED TOXIC EFFECT ON EYES, CAUSING ONSET OF IRRITATION & LACRIMATION SEVERAL HOURS AFTER EXPOSURE ...|... BOTH LIQ AND VAPOR ARE HIGHLY /IRRITATING AND TOXIC/ TO THE SKIN, EYES, LUNG, & INTERNAL ORGANS.|For more Human Toxicity Excerpts (Complete) data for 1,4-DICHLORO-2-BUTENE (6 total), please visit the HSDB record page.

1,4-dichloro-2-butene

ESSENTIALLY 100% AS A CHEM INT FOR 3,4-DICHLORO-1-BUTENE & ADIPONITRILE

1,4-DICHLOROBUTENE AVAILABLE IN USA CONTAINS 95-98% TRANS ... & 2-5% CIS ISOMER.|1,4-Dichlorobutene, technical grade, 85%, is a mixture of both cis- and trans- isomers.

Synthetic rubber manufacturing|2-Butene, 1,4-dichloro-: ACTIVE|In the presence of catalyst (at 100 °C), a liquid mixture of dichlorobutenes equilibrates to a composition of 21% 3,4-dichloro-1-butene, and 7% cis-1,4-, and 72% trans-1,4-dichloro-2-butene. The vapor phase above the liquid contains 52, 6, and 42%, respectively, of the isomers.

DICHLOROBUTENE IN WASTEWATER DETERMINED BY GAS CHROMATOGRAPHY. /DICHLOROBUTENE/|Gas chromatography has been used to determine the products ... resulting from the addition of chlorine to butadiene in acetic acid: Heasley VL et al; J Org Chem 37: 2228-31 (1972).|OSW Method 8240B-W. Determination of Volatile Organics Compounds by Gas Chromatography/Mass Spectrometry (GC/MS). Estimated quantitation limit = 100 ug/l.|OSW Method 8010B. Determination of Halogenated Volatile Organics by Gas Chromatography. Estimated quantitation limit = 100 ug/kg.