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Chloroacetyl chloride

Chloroacetyl chloride structure

Chloroacetyl chloride 

structure
  • CAS No:

    79-04-9

  • Formula:

    C2H2Cl2O

  • Chemical Name:

    Chloroacetyl chloride

  • Synonyms:

    Acetylchloride,chloro-;alpha-Chloroacetyl chloride;CH2ClCOCl;chloracetyl;Chlorid kyseliny chloroctove;chloruredechloracetyle(french);monochloroacetylchloridc;MONO CHLORO ACETYL CHLORIDE

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

Clear colorless liquid Chloroacetyl chloride is a colorless to yellowish liquid with a very pungent, extremely irritating, odor.


Chloroacetyl chloride appears as a colorless to light yellow liquid with a very pungent odor. Very toxic by inhalation. Corrosive to metals and tissue.|Liquid|COLOURLESS-TO-YELLOW LIQUID WITH PUNGENT ODOUR.|Colorless to yellowish liquid with a strong, pungent odor.


Chloroacetyl chloride appears as a colorless to light yellow liquid with a very pungent odor. Very toxic by inhalation. Corrosive to metals and tissue.|Chloroacetyl chloride is an acyl halide.


Chloroacetyl chloride is a colorless to yellowish liquid with a very pungent, extremely irritating, odor.Molecular weight=112.95; Specific gravity (H2O:1) 51.42; Boiling point=105℃; Freezing/Meltingpoint=222℃; Vapor pressure=19 mmHg at 20℃.NFPA 704 M Rating System: Health 3, Flammability 1,Reactivity 1 . Reacts violently with water.


Poison by ingestion and intravenous routes. Mildly toxic by inhalation. Corrosive. A lachrymator. When heated to decomposition it emits toxic fumes of Cl-.

Chloroacetyl chloride Basic Attributes

112.94

112.94

605439

201-171-6

K5UML06YUO

0845

1752

TSCA listed

DTXSID4026472

Clear colorless to slightly yellow

29159000

Characteristics

17.07000

0.99060

Chloroacetyl chloride appears as a colorless to light yellow liquid with a very pungent odor. Very toxic by inhalation. Corrosive to metals and tissue.

1.419 g/mL at 20 °C

−22 °C(lit.)

105-106 °C(lit.)

> 100ºC

n20/D1.453(lit.)

reacts

Store at RT.

60 mm Hg ( 41.5 °C)

3.9 (vs air)

Noncombustible Liquid

strong pungent odor

2.9×10-1mol/(m3Pa) at 25℃, Wang et al. (2017)

Ratio of specific heat of vapor (gas): 1.1191; Heat of solution: -54 Btu/lb = -30 cal/g = -1.3X10+5 J/kg (est)|Critical volume = 0.245 cu m/kmol|Liquid molar volume = 0.080245 cu m/kmol|Heat of formation = -2.4560X10+8 J/kmol|Hydrolyzed by water and alcohol.

Reacts with moisture in the air or with water with generation of heat and hydrochloric acid [Merck, 11th ed., 1989]. Chloroacetyl chloride reacts vigorously with water to generate gaseous HCl. Based on a scenario where the chemical is spilled into an excess of water (at least 5 fold excess of water), half of the maximum theoretical yield of Hydrogen Chloride gas will be created in 1.8 minutes. Experimental details are in the following: "Development of the Table of Initial Isolation and Protective Distances for the 2008 Emergency Response Guidebook", ANL/DIS-09-2, D.F. Brown, H.M. Hartmann, W.A. Freeman, and W.D. Haney, Argonne National Laboratory, Argonne, Illinois, June 2009.

Halogenated Organic Compounds

Water-Reactive

Chloroacetyl chloride reacts rapidly with water. Incompatible with strong oxidizing agents, alcohols, bases (including amines). 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].

-4,000 Btu/lb = -2,000 cal/g = -90X10+5 J/kg (est)

10.30 eV

Noncombustible Liquid

The vapour is heavier than air.

... metals (corrosive)

4.124X10+7 J/Kmol at 251.15 K

Store at RT.

Safety Information

I

6.1

UN 1752

3

T,C,N

9-26-36/37/39-45-61-7/8

AO6475000

C

Chloroacetyl chloride must carry a“CORROSIVE” label. It falls in Hazard Class 8 andPacking Group I.

Stable. Incompatible with strong bases, alcohols, strong oxidizing agents. May react violently on exposure to water or moisture.

P261-P273-P280-P301 + P310-P305 + P351 + P338-P310

Irritant to eyes, corrosive to skin. Upper respiratory tract irritant.

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.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Contaminated packaging: Dispose of as unused product.

Reacts violently with water, steamforming chloroacetic acid and hydrogen chloride gas. Reacts with alcohols, powdered metals; sodium amide; combustibles; and many organics, causing toxic fumes, fire, and explosion hazard. On contact with air it emits corrosive gas. Decomposes when heated forming phosgene gas. Corrosive to metals.

UN 1752

Special Hazards of Combustion Products: Heat of fire can cause decomposition, with evolution of highly toxic and irritating hydrogen chloride and phosgene vapors. Behavior in Fire: Highly irritating (tear gas) vapors released when heated. Hydrogen chloride gas is released if in contact with water. (USCG, 1999)|Not combustible. Gives off irritating or toxic fumes (or gases) in a fire.|Corrosives, Reactive - 1st degree

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P314, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|H290 (31.09%): May be corrosive to metals [Warning Corrosive to Metals]|P234, P260, P261, P262, P264, P270, P271, P273, P280, P301+P310, P301+P330+P331, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P314, P321, P322, P330, P361, P363, P390, P391, P403+P233, P404, P405, and P501|Aggregated GHS information provided by 386 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P264, P270, P271, P280, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P307+P311, P310, P312, P314, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, and P501|P260, P261, P264, P270, P271, P280, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P310, P311, P314, P321, P330, P363, P403+P233, P405, and P501

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: See ERG Table 1 - Initial Isolation and Protective Action Distances on the UN/NA 1752 datasheet. 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 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: 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 damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. A vapor-suppressing foam may be used to reduce vapors. FOR CHLOROSILANES, use AFFF alcohol-resistant medium-expansion foam to reduce vapors. DO NOT GET WATER on spilled substance or inside containers. Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material. Prevent entry into waterways, sewers, basements or confined areas. SMALL SPILL: Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain. Use clean, non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal. (ERG, 2016)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|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 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).|For more Personal Protective Equipment (PPE) (Complete) data for Chloroacetyl chloride (8 total), please visit the HSDB record page.|(See protection codes)

Not combustible, but if involved in a fire decomposes to produce hydrogen chloride.

Suitable extinguishing media: Dry powder, dry sand. Unsuitable extinguishing media: Do NOT use water jet.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.|Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. Use water spray to keep fire-exposed containers cool. Extinguish fire using agent suitable for surrounding fire.|If material involved in fire: Use dry chemical or carbon dioxide. Do not use water on material itself. If large quantities of combustibles are involved, use water in flooding quantities as spray and fog. Use water spray to knock-down vapors. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.|Personnel protection: ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Do not flush with water. Keep in suitable, closed containers for disposal.|Approach release from upwind. Keep water away from release. Stop or control the leak, if this can be done without undue risk. Prompt cleanup and removal is necessary. Control runoff and isolate discharged material for proper disposal.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist.|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.|For more Preventive Measures (Complete) data for Chloroacetyl chloride (10 total), please visit the HSDB record page.

If ... THERE IS NO FIRE, go directly to the Table of Initial Isolation and Protective Action Distances /(see table below)/ ... to obtain initial isolation and protective action distances. IF THERE IS A FIRE, or IF A FIRE IS INVOLVED, go directly to the appropriate guide /(see guide(s) below)/ and use the evacuation information shown under PUBLIC SAFETY.|Table of Water-Reactive Materials Which Produce Toxic Gases.|/GUIDE 156 SUBSTANCES - TOXIC and/or CORROSIVE (Combustible/Water-Sensitive)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.|For more DOT Emergency Guidelines (Complete) data for Chloroacetyl chloride (11 total), please visit the HSDB record page.

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)./|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article. Chloroacetyl chloride is included on the dangerous goods list.|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials. Chloroacetyl chloride is included on the dangerous goods list.

In humans, chloroacetyl chloride is a lacrimator and its vapors are extremely irritating to the eyes and respiratory tract.

Recommended Exposure Limit: 10 Hour Time-Weighted Average: 0.05 ppm (0.2 mg/cu m).

Cover the spilled material with dry sand. Collect leaking and spilled liquid in sealable containers as far as possible. Then store and dispose of according to local regulations. NEVER direct water jet on liquid. Personal protection: complete protective clothing including self-contained breathing apparatus.

Separated from food and feedstuffs. See Chemical Dangers. Dry. Keep in a well-ventilated room.

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

Lachrymation. The substance is corrosive to the skin and respiratory tract. The substance is irritating to the eyes. Corrosive on ingestion. Inhalation of the vapour or aerosol may cause lung oedema. The substance may cause effects on the cardiovascular system. Exposure far above the OEL could cause death. The effects may be delayed. Medical observation is indicated.

Repeated or prolonged contact with skin may cause dermatitis. Repeated or prolonged inhalation may cause effects on the lungs.

AVOID ALL CONTACT! IN ALL CASES CONSULT A DOCTOR!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

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

| 3 - Materials that, under emergency conditions, can cause serious or permanent injury.| 0 - Materials that will not burn under typical fire conditions, including intrinsically noncombustible materials such as concrete, stone, and sand.| 1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.

Toxicity

IDENTIFICATION AND USE: Chloroacetyl chloride is a liquid. It is used in the synthesis of organic compounds. It is also used as a tear gas. HUMAN STUDIES: The effects of acute exposure include: skin erythema and burns, respiratory effects including dyspnea, cyanosis, and cough, and gastrointestinal effects. Painful eye irritation and lacrimation around 1 ppm. Chloroacetyl chloride may promote ventricular arrhythmias. ANIMAL STUDIES: A subchronic inhalation study was conducted in which rats, mice, and hamsters were exposed at averaged vapor concentrations of 0, 0.5, 1, 2.5, or 5 ppm chloroacetyl chloride 6 hours/day, 5 days/week for 4 weeks. Most of the rats inhaling the 5 ppm or 2.5 ppm concentrations died during the first 2 weeks of exposure. Mortality in mice at these two higher concentrations was 15% and 10%, respectively. All animals survived in the other exposure groups, including hamsters at all concentrations. Respiratory and/or eye irritation was observed in all three species at all exposure levels. Chloroacetyl chloride was not mutagenic in five strains of Salmonella, with or without metabolic activation. It did not induce sister chromatid exchange or chromosomal aberrations in Chinese hamster cells when tested both with and without metabolic activation.

LD50 Mouse iv 32 mg/kg|LD50 Rat oral 208 mg/kg|LD50 Mouse oral 220 mg/kg|LC50 Rat inhalation 1000 ppm/4 hr|LC50 Mice inhalation 1300 ppm/2 hr

Chloroacetyl chloride's production and use as a reactive intermediate in the manufacture of adrenalin, diazepam, chloroacetophenone, chloroacetate esters, chloroacetic anhydride, tear gas agents and herbicides, such as alachlor(1,2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Chloroacetyl chloride reacts rapidly with water forming chloroacetic acid and hydrochloric acid(1). As a result, adsorption, volatilization and biodegradation are not expected to be important fate processes in moist soil(SRC). Chloroacetyl chloride is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 25.2 mm Hg at 25 °C(2).|AQUATIC FATE: Chloroacetyl chloride reacts rapidly with water forming chloroacetic acid and hydrochloric acid(1). 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), chloroacetyl chloride, which has a vapor pressure of 25.2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase chloroacetyl chloride 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 670 days(SRC), calculated from its rate constant of 2.4X10-14 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Chloroacetyl chloride contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of chloroacetyl chloride with photochemically-produced hydroxyl radicals has been estimated as 2.4X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 670 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Chloroacetyl chloride contains chromophores that absorb at wavelengths >290 nm(2) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). The half-life of chloroacetyl chloride with respect to homogenous gas-phase hydrolysis in the atmosphere was estimated to be 13,100 years(3). Chloroacetyl chloride reacts rapidly with water forming chloroacetic acid and hydrochloric acid(4).

Chloroacetyl chloride reacts rapidly with water forming chloroacetic acid and hydrochloric acid(1). As a result, bioconcentration is not expected to be an important fate process(SRC).

Chloroacetyl chloride reacts rapidly with water forming chloroacetic acid and hydrochloric acid(1). As a result, adsorption to soil and leaching are not expected to be important fate processes(SRC).

Chloroacetyl chloride reacts rapidly with water forming chloroacetic acid and hydrochloric acid(1). As a result, volatilization from water and moist soil surfaces is not expected to be important fate process(SRC). Chloroacetyl chloride is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 25.2 mm Hg(2).

ACGIH: TWA 0.05 ppm; STEL 0.15 ppm (Skin)NIOSH: IDLH 1.3 ppm; TWA 0.05 ppm(0.2 mg/m3)

Drug Information

Oxidation of the vinyl halide carcinogen and hepatotoxin vinylidene chloride (VDC) by microsomal cytochrome p450 yields 2,2-dichloroacetaldehyde, 2-chloroacetyl chloride, 2-chloroacetic acid, and l,l-dichloroethylene oxide. The roles of these metabolites in covalent modification of proteins and reduced glutathione (GSH) were examined. 2-Chloroacetyl chloride reacted with model thiols at least 10(3)-fold faster than did l,l-dichloroethylene oxide and at least 10(5)-fold faster than did 2,2-dichloroacetaldehyde or 2-chloroacetic acid.

Inhalation causes severe irritation of upper respiratory system. External contact causes severe irritation of eyes and skin. Ingestion causes severe irritation of mouth and stomach.

Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, immediately flush the contaminated skin with water. If this chemical penetrates the clothing, immediately remove the clothing and flush the skin with water. Get medical attention promptly. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)


Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.


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


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

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. /Chlorine and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. 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 ... . 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Chlorine and related compounds/|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. 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 (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Chlorine and related compounds/

/SIGNS AND SYMPTOMS/ Medical reports of the effects of acute exposure include: skin erythema and burns; respiratory effects including dyspnea, cyanosis, and cough; and gastrointestinal effects.|/SIGNS AND SYMPTOMS/ ... No eye irritation at 0.140 ppm but ... painful eye irritation and lacrimation around 1 ppm.|/CASE REPORTS/ A male employee of a pharmaceutical company experienced a large skin area exposure to a mixture of chloroacetyl chloride, xylidine, and benzene. The worker was put under a shower within 5 min of the accident, but shortly thereafter, he began to have respiratory difficulties, collapsed, and experienced an apparent grand mal seizure. At the time of the published account, 2 years after the accident, the patient was still comatose. The relative contribution of the three chemicals to the patient's condition is unknown. However, the authors related information obtained from the chloroacetyl chloride manufacturer that two fatalities had resulted from exposure to chloroacetyl chloride, one of them following massive skin contact followed by cardiorespiratory arrest within a few minutes. According to that manufacturer, other data indicated that chloroacetyl chloride may promote ventricular arrhythmias.

chloroacetyl chloride

The substance can be absorbed into the body by inhalation of its aerosol or vapour, through the skin and by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact

irritation eyes, skin, respiratory system; eye, skin burns; cough, wheezing, dyspnea (breathing difficulty); lacrimation (discharge of tears)


Cough. Laboured breathing. Burning sensation. Blue lips, fingernails and skin. Shortness of breath. Sore throat. Symptoms may be delayed.


MAY BE ABSORBED! Redness. Pain. Serious skin burns. Blisters.


Pain. Redness. Blurred vision. Severe deep burns.

Eyes, skin, respiratory system

Chloroacetyl chloride Use and Manufacturing

Methods of Manufacturing

Chloroacetyl chloride is usually manufactured from chloroacetic acid by reaction with phosphorus trichloride, thionyl chloride, sulfuryl chloride, or phosgene. It is also obtained by chlorination of acetyl chloride in the presence of stronger aliphatic acids, preferably chloroacetic acids, or from sodium chloroacetate and the usual chlorinating agents.|Manufactured by reaction of chloroacetic acid with chlorinating agents such as phosphorus oxychloride, phosphorus trichloride, sulfuryl chloride or phosgene. Various catalysts have been used to promote the reaction. Chloroacetyl chloride is also produced by chlorination of acetyl chloride, the oxidation of 1,1-dichloroethene, and the addition of chlorine to ketene..|Preparation from chloroacetic acid and benzoyl chloride ... ; by chlorination of ketene ... ; Prill, United States patent 2889365 (1959 to Monsanto); from chloroacetic acid and pyrocatechylphosphorus trichloride ... . Manufactured from chloroacetic acid and POCl2: MacKenzie, Morris, United States patent 2848491 (1958 to Dow); from ketene: Prill, United States patent 2889365 (1959 to Monsanto).|(1) Action of chlorine on acetyl chloride in sunlight. (2) Dropping phosphorus trichloride on chloroacetic acid.

Uses

Chloroacetyl chloride is a chlorinated acyl chloride. It is a bifunctional compound, making it a useful building block chemical.


Intermediates


In the synthesis of organic compounds.


Chloroacetyl chloride is an intermediate in the production of alachlor and butachlor. It is used to prepare phenacyl chloride through Friedel-Crafts acylation of benzene.


Intermediate in manufacture of chloroacetophenone and various other chemicals

Production

50,000,000 - 100,000,000 lb|(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1975) GREATER THAN 4.54X10+5 GRAMS|Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Chloroacetylchloride:

Much of the chloroacetyl chloride produced is used captively as a reactive intermediate.|Estimated that the chloroacetyl chloride requirement for the manufacture of alachlor and butachlor was in excess of 45,000 metric tons in 1992. Significant volumes are also used in pharmaceutical manufacture, such as anesthetics of the lidocaine type, and in the production of the tear gas chloroacetophenone.

Pesticide, fertilizer, and other agricultural chemical manufacturing|Acetyl chloride, 2-chloro-: ACTIVE|Chloroacetyl chloride is usually manufactured from chloroacetic acid by reaction with phosphorus trichloride, thionyl chloride, sulfuryl chloride, or phosgene. It is also obtained by chlorination of acetyl chloride in the presence of stronger aliphatic acids, preferably chloroacetic acids, or from sodium chloroacetate and the usual chlorinating agents.

A gas chromatographic procedure has been developed for the trace determination of chloroacetyl chloride (CAC) and two of its impurities: methyl chloroacetate (MCA) and chloroacetic acid (CAA). All three compounds are derivatized using piperidine in dichloroethane prior to their analysis via gas chromatography coupled with a flame ionization detection (GC-FID). Recoveries of each compound were assessed in two different pharmaceutical matrices (intermediate and final active pharmaceutical ingredient) and ranged from 75 to 125%. The limit of quantitation has been determined to be 0.10% wt/wt for CAA and 0.03% wt/wt for CAC and MCA. The linearity ranged from 0.03 to 5.00% wt/wt for CAC and MCA and from 0.10 to 5.00% wt/wt for CAA, with correlation coefficients from 0.9995 to 1.0000. Repeatability was evaluated at LOQ and at 5.00% wt/wt and was found to be between 1.4-3.0%.|A simple and rapid capillary zone electrophoretic method was developed for determining dimethyl sulfate a possible human carcinogen and mutagen and chloroacetyl chloride a potential genotoxic agent at trace levels in pharmaceutical drug substances by indirect photometric detection. A systematic screening of various anionic probes was performed to obtain the best separation conditions and sensitivity. High sensitivities with low quantification and detection levels were achieved for dimethylsulfate and chloroacetyl chloride using a background electrolyte (BGE) containing 5 mM pyridine dicarboxylic acid as the probe ion. The method is specific, precise and accurate for the two genotoxins. The optimized method was validated for specificity, precision, linearity, accuracy and stability in solution. Calibration curves were linear (R>0.999) for both dimethylsulfate and chloroacetyl chloride in the range LOQ - 300% of nominal concentrations. The CE method was effectively implemented for estimating dimethylsulfate and chloroacetyl chloride in two different active pharmaceutical ingredients (APIs).|Determination of chloroacetyl chloride in air by ion chromatography.|Analysis by HPLC using acetonitrile as the mobile phase and UV detection, XAD-7 tube with 1-(2-pyridyl)piperazine; detection limit of 4.8 ug/cu m.

Fire Hazards -> Corrosives, Reactive - 1st degree

Computed Properties

Molecular Weight:112.94
XLogP3:1.4
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:111.9482701
Monoisotopic Mass:111.9482701
Topological Polar Surface Area:17.1
Heavy Atom Count:5
Complexity:42.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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