Acryloyl chloride

90.51

90.51

635744

212-399-0

8K23O56TG5

93770

2924

DTXSID1061150

Liquid|Light yellow liquid

29161980

17.1

1.4

Acrylyl chloride appears as a liquid. Boiling point 75°C. Used to make plastics. Polymerization in a closed container can cause pressurization and explosive rupture. (EPA, 1998)

1.1136 g/cm³ @ Temp: 20 °C

76 °C @ Solvent: Diisopropyl ether

75 °C

61 °F

n20/D 1.435(lit.)

Miscible with water.Very soluble in chloroform

2-8°C

1.93 psi ( 20 °C)

>1 (vs air)

Inhalation-rat LCL0: 25 PPM/4 hours; inhalation-mouse LC50: 92 mg/m3/2 hours

Flammable; decomposes by heating to release toxic chloride fumes

Vapors may form explosive mixture with air.

Hydrolyzed by water|Acyl halides react readily (some violently) with water to yield the parent acid and hydrogen halide. For example, acetyl chloride hydrolyzes to yield acetic acid and hydrochloric acid. Hydrolysis half-lives are less than 10 minutes (or faster). Half-life at 25 °C: acetyl chloride 0.8 seconds; benzoyl chloride: 16 seconds.|When heated to decomposition, it emits toxic fumes of Cl(-).|Hydroxyl radical reaction rate constant = 9.21X10-12 cu cm/molec-sec at 25 °C (est)|Ozone reaction rate constant = 1.7X10-16 cu cm/molec-sec at 25 °C (est)

Polymerizes readily upon exposure to oxygen in the air. Reacts exothermically with water to give hydrochloric acid and acrylic acid.

Acyl Halides, Sulfonyl Halides, and Chloroformates

Polymerizable

ACRYLYL CHLORIDE is incompatible with strong oxidizing agents, alcohols, amines, alkali. Polymerizes readily upon exposure to oxygen. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Corrosive to metals

II

3

UN 3383 6.1/PG 1

3

11-14-26-34

16-26-28-36/37/39-45-7/9

AT7350000

F,T+

Warehouse ventilated, low temperature and dry

Stable, but reacts violently with water. Incompatible with alcohols, oxidizing agents, strong bases. Light-sensitive. Highly flammable.

P210, P233, P240, P241, P242, P243, P260, P271, P280, P284, P303+P361+P353, P304+P340, P310, P320, P370+P378, P403+P233, P403+P235, P405, P501

H225

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Contact a licensed professional waste disposal service to dispose of this material. Offer surplus and non-recyclable solutions to a licensed disposal company. Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Contaminated packaging: Dispose of as unused product.

Incompatible materials: Strong bases|Reacts violently with water, forming acrylic acid. Keep away from strong oxidizers.|A 500 mL bottle of the acid chloride stabilized with 0.5% of phenothiazine was shipped to a hot climate without refrigeration, and was stored on arrival in a fume cupboard for 2 days at temperatures approaching 50 °C. The material polymerized, bursting the bottle and forming a solid foam.

When heated to decomposition, it emits toxic fumes of chlorides. Decomposes in water. (EPA, 1998)|Flammable - 3rd degree, Reactive - 1st degree

|Danger|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P280, P284, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P320, P321, P330, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 50 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P234, P240, P241, P242, P243, P260, P264, P270, P271, P280, P284, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P363, P370+P378, P390, P403+P233, P403+P235, P404, P405, and P501|P210, P233, P240, P241, P242, P243, P260, P271, P280, P284, P303+P361+P353, P304+P340, P310, P320, 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)

Avoid inhalation. (EPA, 1998)

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)|Eye/face protection: Tightly fitting safety goggles. Faceshield (8-inch minimum). Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166 (EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. Flame retardant antistatic protective clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Flammable liquid.

Suitable extinguishing media: Dry powder, dry sand|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.|Use water spray to cool unopened containers.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Contain spillage, and then collect with non-combustible absorbent material, (e.g. sand, earth, diatomaceous earth, vermiculite) and place in container for disposal according to local/national regulations.|For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure-demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Use explosion-proof equipment. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.|Appropriate engineering controls: Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./

Acrylyl chloride /inhalation toxicity/ 100 ppm (D): ... 4F rats: 1 x 4-hr exposure: eye irritation ... 4F rats: 5 x 5-hr exposures: eye irritation ...

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Acrylyl chloride is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 lbs.

highly toxic

IDENTIFICATION AND USE: Acrylyl chloride is a liquid. It is used as a monomer and chemical intermediate. HUMAN STUDIES: Three university students were exposed to toxic vapors (acryloyl chloride 96% and methacrylic anhydride 94%) in a laboratory accident. They all gave a history of minimal exposure and presented with mild symptoms. One patient died on the same day. The other two cases were uneventful. ANIMAL STUDIES: Inhalation exposure to 100 ppm acrylyl chloride for 2 hr produced in rats lethargy and respiratory difficulty, during autopsy lung edema was noted.

LC50 Mouse inhalation 92 mg/cu m/2 hr|LD50 Mouse iv 180 mg/kg

Acrylyl chloride's production and use as a chemical intermediate(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: As a class, acyl halides react readily with water to yield the parent acid and hydrogen halide(1-2). As a result, adsorption, volatilization and biodegradation are not expected to be important fate processes in moist soil(SRC). Acrylyl chloride is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 115 mm Hg at 25 °C(SRC), determined from a fragment constant method(3).|AQUATIC FATE: As a class, acyl halides react readily with water to yield the parent acid and hydrogen halide(1-2). As a result, adsorption to suspended solids and sediment, bioconcentration, volatilization, and biodegradation are not expected to be important fate processes in aquatic systems(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acrylyl chloride, which has an estimated vapor pressure of 115 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 acrylyl chloride is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone(SRC); the half-lives for these reactions in air are estimated to be 1.7 and 6.6 days(SRC), calculated from respective rate constants of 9.2X10-12 and 1.7X10-16 cu cm/molecule-sec at 25 °C(SRC), that were derived using a structure estimation method(2). Acrylyl chloride contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of acrylyl chloride with photochemically-produced hydroxyl radicals has been estimated as 9.2X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.7 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of acrylyl chloride with ozone has been estimated as 1.7X10-16 cu cm/molecule-sec at 25 °C(SRC), that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6.6 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). As a class, acyl halides react readily with water to yield the parent acid and hydrogen halide(3-4). Therefore, acrylyl chloride is expected to undergo rapid hydrolysis in the environment(SRC). Acrylyl chloride contains chromophores that absorb at wavelengths >290 nm(5) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

As a class, acyl halides react readily with water to yield the parent acid and hydrogen halide(1-2). Analogous acetyl chloride and chloroacetyl chloride hydrolyze rapidly to yield acetic acid and hydrochloric acid(1), and chloroacetic acid and hydrochloric acid(2), respectively. Therefore, bioconcentration is not expected to be an important environmental fate process(SRC).

As a class, acyl halides react readily with water to yield the parent acid and hydrogen halide(1-2). Analogous acetyl chloride and chloroacetyl chloride hydrolyze rapidly to yield acetic acid and hydrochloric acid(1), and chloroacetic acid and hydrochloric acid(2), respectively. Therefore, adsorption to soil and mobility are not expected to be important environmental fate processes(SRC).

As a class, acyl halides react readily with water to yield the parent acid and hydrogen halide(1-2). Analogous acetyl chloride and chloroacetyl chloride hydrolyze rapidly to yield acetic acid and hydrochloric acid(1), and chloroacetic acid and hydrochloric acid(2), respectively. Therefore, volatilization of acrylyl chloride from water or moist soil surfaces is not expected to be an important environmental fate process(SRC). Acrylyl chloride is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 115 mm Hg(SRC), determined from a fragment constant method(3).

According to the 2012 TSCA Inventory Update Reporting data, 1 reporting facility estimated the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of acrylyl chloride in the United States may be as low as <10 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|Occupational exposure to acrylyl chloride may occur through inhalation and dermal contact with this compound at workplaces where acrylyl chloride is produced or used. (SRC)

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. (ERG, 2016)

Signs and Symptoms of Acrylyl Chloride Exposure: Acrylyl chloride may be very irritating to the skin, eyes, mucous membranes, and respiratory tract. Lacrimation (tearing) is common. Coughing and difficulty in breathing may be noted along with pulmonary edema in more severe exposures. Other signs and symptoms of acute exposure may include headache, dizziness, and weakness. Gastrointestinal effects may include nausea, vomiting, and diarrhea. Emergency Life-Support Procedures: Acute exposure to acrylyl chloride exposure may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. Inhalation Exposure: 1. Move victims to fresh air. Emergency personnel should avoid self-exposure to acrylyl chloride. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support. 3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 4. Transport to a health care facility. Dermal/Eye Exposure: 1. Remove victims from exposure. Emergency personnel should avoid self-exposure to acrylyl chloride. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support. 3. Remove contaminated clothing as soon as possible. 4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 5. Wash exposed skin areas THOROUGHLY with soap and water. 6. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 7. Transport to a health care facility. Ingestion Exposure: 1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support. 2. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 3. Give the victims water or milk: children up to 1 year old, 125 mL (4 oz or 1/2 cup); children 1 to 12 years old, 200 mL (6 oz or 3/4 cup); adults, 250 mL (8 oz or 1 cup). Water or milk should be given only if victims are conscious and alert. 4. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water. 5. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 50 to 100 g (1-3/4 to 3- 1/2 oz) is recommended for adults. 6. Transport to a health care facility. (EPA, 1998)

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Irritating materials/|Basic Treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Encourage patient to take deep breaths. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . /Irritating materials/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Early intubation at the first sign of upper airway obstruction may be necessary. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... Use proparacaine hydrochloride to assist eye irrigation ... . /Irritating materials/|Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|For more Antidote and Emergency Treatment (Complete) data for Acrylyl chloride (6 total), please visit the HSDB record page.

/CASE REPORTS/ Three university students were exposed to toxic vapors (acryloyl chloride 96% and methacrylic anhydride 94%) in a laboratory accident. They all gave a history of minimal exposure and presented with mild symptoms. One patient died on the same day. The other two cases were uneventful. This paper reports on these three cases, followed by a discussion on irritant gas intoxication. /Mixture/

acryloyl chloride

Stabilized with 200 ppm phenothiazine and 100 ppm hydroquinone.

2-Propenoyl chloride: ACTIVE|... Reactions of the heptafluoroisopropyoxy anion prepared from hexafluoroacetone and potassium fluoride with acrylyl chloride and glycidyl bromide have led to the preparation of polymerizable acrylates and epoxides.|Vinyl isocyanate... is prepared by heating acryloyl chloride with sodium azide|Acrylic acid ... can be easily converted to ... acryloyl chloride, by reaction with phosphorous oxychloride, or benzoyl or thionyl chloride.|... Fluorocarbons have a much broader resistance to physical and chemical attack than acrylic polymers, but lack the advantages of acrylic polymers. It is an objective of the present invention to substantially increase the fluorocarbon content in acrylic resins, without interfering with the acrylate properties. Another object of this invention is to vary the fluorine content of fluroacrylic resins over wide ranges through the placement of perfluoroalkyl pendant groups of different lengths. These and other objects are achieved by reacting a fluoroaromatic diol and acryloyl chloride in a highly fluorinated solvent with an acid acceptor to form a fluorinated diacrylate ester monomer and purifying the monomer by forming a solution, adding decolorizing carbon to the solution and percolating the solution through activated alumina.|For more General Manufacturing Information (Complete) data for Acrylyl chloride (7 total), please visit the HSDB record page.

Fire Hazards -> Flammable - 3rd degree, Reactive - 1st degree