Chloroprene

HCID 31369CAS 126-99-8

Basic information

Standard SMILES
C=CC(=C)Cl
InChIKey
YACLQRRMGMJLJV-UHFFFAOYSA-N
Molecular formula
C4H5Cl
Average molar mass
88.53 g/mol
Monoisotopic mass
88.0079779

Names & identifiers

Preferred name
Chloroprene
IUPAC
2-chlorobuta-1,3-diene
English name
2-chloro-1,3-butadiene
Molecular formula
C4H5Cl
Molecular weight
88.54

Names & synonyms

CHLOROPRENE2-Chlorobuta-1,3-diene2-Chloro-1,3-butadiene126-99-8Chlorobutadiene2-Chlorobutadiene1,3-Butadiene, 2-chloro-ChloropreenCloroprenebeta-Chloroprene2-Chlor-1,3-butadienChloropren
Show more names
CHLOROPENEBaypren M1Neoprene AHBaypren 110
2-Cloro-1,3-butadiene2-Chloor-1,3-butadieen42L93DWV3ADTXSID5020316NSC-18589CHEBI:39481NSC18589RefChem:125490

Database identifiers

CAS
126-99-8
PubChem CID
31369
DTXSID
DTXSID5020316
ChEMBL
CHEMBL555660
ChEBI
CHEBI:39481
UNII
42L93DWV3A
EC Number
204-818-0
Nikkaji
J384K

Properties

Computed structural properties

XLogP
2.3
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
1
Heavy atoms
5

Experimental & physicochemical properties

LogP2.2 (calculated)
OdorPungent, ether-like odor
Density · 6 items

0.9583 at 68 °F (USCG, 1999) - Less dense than water; will float

0.956 @ 20 °C/4 °C

Density of saturated air: 1.57 (air= 1)

Relative density (water = 1): 0.96

0.96

.956 @ 20°C

Color/FormColorless liquid
Solubility · 5 items

Slightly soluble (NTP, 1992)

Miscible in ethyl ether, acetone, and benzene; slightly soluble in water.

Soluble in alcohol, diethyl ether

Solubility in water, g/100ml at 20 °C: 0.03 (very poor)

Slight

Flash Point · 6 items

-4 °F (NTP, 1992)

-4 °F

-20 °C (OPEN CUP)

-20 °C c.c.

-4 °F

-4 °F

Physicochemical properties

Melting point
-130 °C · -130°C
Boiling point
59.45 °C · 59.45°C
Density
0 · 0,958 g/cm3
vapor pressure
118 at · 118 at 10 °C, 200 at 20 °C, 275 at 30 °C (quoted, Verschueren, 1983)
refractive index
1.4583 · 1.4583
Flash point
11 °C · 11 °C

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids];H302: Harmful if swallowed [Warning Acute toxicity, oral];H315: Causes skin irritation [Warning Skin corrosion/irritation];H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation];H332: Harmful if inhaled [Warning Acute toxicity, inhalation];H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H350: May cause cancer [Danger Carcinogenicity];H373 **: May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

P203, P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

Hazard information

Regulatory Information · 6 items

Chemical: 1,3-Butadiene, 2-chloro-

Hazard Traits - Carcinogenicity; Cardiovascular Toxicity; Hepatotoxicity and Digestive System Toxicity; Neurotoxicity; Respiratory Toxicity;Authoritative List - CA TACs; EC Annex VI CMRs - Cat. 1B; IARC Carcinogens - 2B; IRIS Carcinogens - Likely Carcin.; NTP RoC - reasonable; Prop 65;Report - regardless of intended function of ingredient in the product

1,3-Butadiene, 2-chloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Butadiene, 2-chloro- 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: 07-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15226

1,3-Butadiene, 2-chloro-: HSNO Approval: HSR001109 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - 1,3-Butadiene, 2-chloro-: Human health tier I assessment;IMAP assessments - 1,3-Butadiene, 2-chloro-: Environment tier I assessment
DOT LabelFlammable Liquid Poison
Fire Hazards · 3 items

Special Hazards of Combustion Products: Decomposes yielding toxic fumes;Behavior in Fire: Dangerous when exposed to heat or flame (USCG, 1999)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.;CAUTION: Methanol (UN1230) will burn with an invisible flame. Use an alternate method of detection (thermal camera, broom handle, etc.);· Vapors may form explosive mixtures with air.;· Vapors may travel to source of ignition and flash back.;· Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.).;· Vapor explosion and poison hazard indoors, outdoors or in sewers.;· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.;· Runoff to sewer may create fire or explosion hazard.;· Containers may explode when heated.;· Many liquids will float on water.

Highly flammable. Many reactions may cause fire or explosion. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.

Fire PotentialA very dangerous fire hazard when exposed to heat or flame.
Health Hazards · 2 items

INHALATION: Fatigue, psychic changes, irritability, oppression in chest, occasionally substernal pain, tachycardia upon exertion. EYES: Can cause conjunctivitis, corneal necrosis and edema of eyelids. SKIN: May cause dermatitis and temporary loss of hair. Rapidly absorbed by skin. (USCG, 1999)

· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.;· Inhalation or contact with some of these materials will irritate or burn skin and eyes.;· Methyl chloroacetate (UN2295) is an eye irritant/lachrymator (causes flow of tears).;· Fire will produce irritating, corrosive and/or toxic gases.;· Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas.;· Runoff from fire control or dilution water may cause environmental contamination.

Safety & protection

Fire Fighting · 2 items

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic; polymerization hazard]:;CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient. CAUTION: Methanol (UN1230) will burn with an invisible flame. Use an alternate method of detection (thermal camera, broom handle, etc.).;SMALL FIRE: Dry chemical, CO2, water spray or alcohol-resistant foam.;LARGE FIRE: Water spray, fog or alcohol-resistant foam. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal. Avoid aiming straight or solid streams directly onto the product.;FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2024)

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

First Aid Measures · 4 items

Fresh air, rest. Half-upright position. Refer immediately for medical attention.

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

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

Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.

Accidental Release Measures · 2 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.;· Keep unauthorized personnel away.;· Stay upwind, uphill and/or upstream.;· Ventilate closed spaces before entering, but only if properly trained and equipped.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from 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.;Small Spill;· Absorb with earth, sand or other non-combustible material and transfer to containers for later disposal.;· 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.

First Aid · 3 items

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. Volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

General First Aid:;· Call 911 or emergency medical service.;· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.;· Move victim to fresh air if it can be done safely.;· Administer oxygen if breathing is difficult.;· If victim is not breathing:;-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingested or inhaled the substance.;-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).;-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.;· Remove and isolate contaminated clothing and shoes.;· For minor skin contact, avoid spreading material on unaffected skin.;· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.;· For severe burns, immediate medical attention is required.;· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.;· Keep victim calm and warm.;· Keep victim under observation.;· For further assistance, contact your local Poison Control Center.;· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.;Specific First Aid:;· Wash skin with soap and water.

(General first aid procedures);Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: Soap wash immediately - If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly.;Breathing: Respiratory support;Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

Safe StorageFireproof. Separated from food and feedstuffs and incompatible materials. See Chemical Dangers. Cool. Keep in the dark. Well closed. Store only if stabilized. Store in an area without drain or sewer access.
Exposure Control and Personal Protection · 1 item

· Wear positive pressure self-contained breathing apparatus (SCBA).;· Wear chemical protective clothing that is specifically recommended by the manufacturer when there is NO RISK OF FIRE.;· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection.

Toxicology

Cancer Sites · 2 items

Dermal;Gastrointestinal;Hepatic;Ocular;Reproductive;Respiratory

[lung & skin cancer]

Interactions · 2 items

PRETREATMENT WITH AROCLOR PREVENTED LIVER INJURY FOLLOWING EXPOSURE TO 100 & 300 PPM OF CHLOROPRENE. LUNG NONPROTEIN SULFHYDRYL CONCN WAS NOT DECR BY CHLOROPRENE EXPOSURE OF POLYCHLORINATED BIPHENYL PRETREATED RATS.

The brain ATP levels in rats were decreased at 7-30 days after the ip injection of chloroprene (600 umol/100 g body weight). However, the simultaneous administration of alpha-tocopherol acetate (0.1 mg/100 g body weight) counteracted this effect of chloroprene. The toxicity of chloroprene depletes the endogenous alpha-tocopherol supply. Administration of exogenous alpha-tocopherol can then counteract this toxic effect of chloroprene.

Target Organs · 2 items

Immune;Nervous;Respiratory

Eyes, skin, respiratory system, reproductive system

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 68(SRC), determined from a structure estimation method(2), indicates that 2-chloro-1,3-butadiene is expected to have high mobility in soil(SRC). Volatilization of 2-chloro-1,3-butadiene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.056 atm-cu m/mole (SRC), using a fragment constant estimation method(3). The potential for volatilization of 2-chloro-1,3-butadiene from dry soil surfaces may exist(SRC) based upon a vapor pressure of 215 mm Hg(4). 2-Chloro-1,3-butadiene will not be susceptible to chemical hydrolysis(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 68(SRC), determined from a structure estimation method(2), indicates that 2-chloro-1,3-butadiene 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 0.056 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 3 hours and 4 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 18(SRC), from an estimated log Kow of 2.53(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. 2-Chloro-1,3-butadiene is not expected to undergo chemical hydrolysis(SRC) because of the lack of hydrolyzable functional groups(3).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-chloro-1,3-butadiene, which has a vapor pressure of 2.15X10+2 mm Hg at 25 °C, is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-chloro-1,3-butadiene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals, ozone molecules and nitrate radicals(SRC). The half-life for the reaction in air with hydroxyl radicals is estimated to be 18 hours(SRC), calculated from its rate constant of 22X10-12 cu cm/molecule-sec at 25 °C(SRC), determined using a structure estimation method(2). The rate constant for the vapor-phase reaction of 2-chloro-1,3-butadiene with ozone has been estimated as 0.12X10-17 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(2). This corresponds to an atmospheric half-life of about 10 days(SRC) at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(3). The gas phase reaction of 2-chloro-1,3-butadiene with nitrate radicals may be an important atmospheric removal process in urban areas at night(4), but the rate of this reaction is not known.

Adverse Effects · 1 item

Neurotoxin - Other CNS neurotoxin;Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.;Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.;Dermatotoxin - Skin burns.;Lacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.;IARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.;NTP Carcinogen - Reasonably anticipated to be a human carcinogen.;ACGIH Carcinogen - Suspected Human.

Exposure Routes · 2 items

The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Regulatory information

Regulatory Information · 6 items

Chemical: 1,3-Butadiene, 2-chloro-

Hazard Traits - Carcinogenicity; Cardiovascular Toxicity; Hepatotoxicity and Digestive System Toxicity; Neurotoxicity; Respiratory Toxicity;Authoritative List - CA TACs; EC Annex VI CMRs - Cat. 1B; IARC Carcinogens - 2B; IRIS Carcinogens - Likely Carcin.; NTP RoC - reasonable; Prop 65;Report - regardless of intended function of ingredient in the product

1,3-Butadiene, 2-chloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Butadiene, 2-chloro- 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: 07-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15226

1,3-Butadiene, 2-chloro-: HSNO Approval: HSR001109 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

FDA RequirementsChloroprene is an indirect food additive for use only as a component of adhesives.
TSCA Requirements · 2 items

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Chloroprene is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble of the 51 FR 41329.

Atmospheric Standards · 3 items

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Chloroprene is produced, as an intermediate or a final product, by process units covered under this subpart.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 2-Chloro-1,3-butadiene is included on this list.

... Substances for which a Federal Register notice has been published that included consideration of the serious health effects, including cancer, from ambient air exposure to the substance. Chloroprene is included on this list.

CERCLA Reportable Quantities · 1 item

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).

Safety data

OEL
Ceiling: 1 ppm (3.6 mg/m3) [15-minute]
wgk
3
IDLA
300 ppm
tsca
TSCA listed
ridadr
UN 1991 (CHLOROPRENE, STABILIZED)
Toxicity
Acute oral LD50 for mice 260 mg/kg, rats 900 mg/kg (quoted, RTECS, 1985).

Chemistry & industry

Pharmacology

Biological Half-LifeNo reports found; [TDR, p. 334]
Metabolism/MetabolitesWHEN MIXT OF CHLOROPRENE IN AIR WAS PASSED THROUGH A MOUSE LIVER MICROSOMAL PREPN, A VOLATILE ALKYLATING METABOLITE WAS FORMED, AS DEMONSTRATED BY TRAPPING WITH 4-(4-NITROBENZYL)PYRIDINE.
Absorption, Distribution and Excretion... RAPIDLY ABSORBED BY SKIN ... .

Uses & manufacturing

Uses · 5 items

Chloroprene is a flammable liquid with a pungent odor. It is used primarily in the manufacture of polychloroprene (Neoprene TM, duprene) which is a polychloroprene elastomer that is used to make diverse products including adhesives, automotive and industrial parts (e.g., belts and hoses), wire and cable covers, adhesives, caulks, flame-resistant cushioning and other applications requiring chemical, oil, and/or weather resistance.

Used to manufacture synthetic rubber (neoprene and polychloroprene latex); [ACGIH]

... Used as a chemical intermediate in the manufacture of artificial rubber.

... AS COMPONENT OF ADHESIVES THAT ARE INTENDED FOR USE IN FOOD PACKAGING.

Manufacture of neoprene.

ImpuritiesINHIBITORS SUCH AS HYDROQUINONE OR PHENOTHIAZINE ARE GENERALLY ADDED WHEN IT IS TO BE STORED.
U.S. Production2023: 25,000,000 - <75,000,000 lb;2022: 25,000,000 - <75,000,000 lb;2021: 25,000,000 - <75,000,000 lb;2020: 25,000,000 - <75,000,000 lb
Consumption PatternsESSENTIALLY 100% AS A MONOMER FOR NEOPRENE ELASTOMERS.
Industry UsesIntermediate;Monomers
Methods of ManufacturingAddition of cold hydrochloric acid to vinylacetylene; chlorination of butadiene.
Applications · 5 items

DescriptionChloroprene, 2-chloro-1,3-butadiene, is a colorless, volatile synthetic liquid that has a pungent ether-like odor. Synthesis of chloroprene was first reported by chemists of the E. I. du Pont de Nemours Company in 1931 following studies of acetylene polymerization with the objective of producing synthetic rubber. The chloroprene monomer differs from isoprene, the fundamental monomer of natural rubber, only by substitution of chlorine for the methyl group of isoprene. Chloroprene was observed to polymerize much more quickly than did isoprene. In industrial processes prior to 1960, chloroprene was produced in relatively high yields by reacting vinyl acetylene with hydrogen chloride. Today, chloroprene is produced more efficiently by chlorination of 1,3-butadiene. When compared with natural rubber the chloroprene synthetic polymer, polychloroprene, was noted to be much denser, more resistant to water and hydrocarbon solvents, less permeable to many gases, and was more resistant to degradation by oxygen, ozone, hydrogen chloride, hydrogen fluoride, and other chemicals. Due to desirable physical and chemical properties, polychloroprene and its latex polymers are produced in quantities exceeding 200 000 metric tons at a limited number of facilities around the world. Chloroprene production is closely tied to demand for polychloroprene.

UsesThe only commercial use identified for chloroprene is as a monomer in the production of the elastomer polychloroprene (neoprene), a synthetic rubber used in the production of automotive and mechanical rubber goods, adhesives, caulks, flame-resistant cushioning,construction materials, fabric coatings, fiber binding, and footwear. Other uses of this polymer include applications requiring chemical, oil, or weather resistance or high gum strength. The U.S. Food and Drug Administration permits the use of chloroprene as a component of adhesives used in food packaging and also permits the use of polychloroprene in products intended for use with food (IARC 1979, 1999, NTP 1998).

UsesAlmost all the chloroprene produced is used for the manufacture of these polychloroprene rubbers. Chloroprene is a volatile, toxic, flammable liquid and is especially susceptible to oxidation and polymerization.

UsesManufacture of neoprene.

General DescriptionA clear colorless liquid. Flash point -4°F. May polymerize exothermically if heated or contaminated. If polymerization takes place inside a container, the container may rupture violently. Less dense than water. Vapors heavier than air. Used to make neoprene rubber.

Preparation methods · 1 item

PreparationPreparation of chloroprene from butadiene In this method, the following route is used:In the first step, butadiene is chlorinated in the vapour phase at 330-420 and atmospheric pressure. The main products are 3,4-dichloro-l-butene and 1,4-dichloro-2-butene in approximately equal amounts. The latter material is then isomerized to the former by heating with a copper catalyst such as cuprous chloride. The 3,4-dichloro-l-butene is dehydrochlorinated by treatment with 10% aqueous sodium hydroxide at 85. Chloroprene is isolated by distillation under reduced pressure in the presence of polymerization inhibitors.

Additional notes

DefinitionA colorless liquid derivative of butadiene used in the manufacture of neoprene rubber.

Related reactions

18 records

Linked notes

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