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Chloroacetone

Chloroacetone structure

Chloroacetone 

structure
  • CAS No:

    78-95-5

  • Formula:

    C3H5ClO

  • Chemical Name:

    Chloroacetone

  • Synonyms:

    2-Propanone,1-chloro-;2-Propanone,chloro-;1-Chloro-2-propanone;Acetonyl chloride;Chloroacetone;Chloropropanone;Monochloroacetone;α-Chloroacetone;1-Chloroacetone;Chloromethyl methyl ketone;Chloro-2-propanone;Methyl chloromethyl ketone;NSC 30673

  • Categories:

    Organic Chemistry  >  Ketones

Description

colourless to dark yellow liquid


Chloroacetone is a chemical compound with the formula CH3COCH2Cl. At STP it is a colourless liquid with a pungent odour. On exposure to light, it turns to a dark yellow-amber colour. It was used as a tear gas in World War I.


Chloroacetone, stabilized appears as a yellow-colored liquid with an irritating pungent odor. Light sensitive, but stabilized with the addition of small amounts of water and/or calcium carbonate. Slightly soluble in water and denser than water. Vapors much heavier than air. Irritates skin and eyes. Very toxic by ingestion or inhalation. Used to make other chemicals. A lachrymator.|COLOURLESS LIQUID WITH PUNGENT ODOUR. TURNS DARK ON EXPOSURE TO LIGHT.|A yellow-colored liquid with an irritating pungent odor.


Chloroacetone, stabilized appears as a yellow-colored liquid with an irritating pungent odor. Light sensitive, but stabilized with the addition of small amounts of water and/or calcium carbonate. Slightly soluble in water and denser than water. Vapors much heavier than air. Irritates skin and eyes. Very toxic by ingestion or inhalation. Used to make other chemicals. A lachrymator.|Chloroacetone is an alpha-chloroketone. It derives from an acetone.

Chloroacetone Basic Attributes

92.52

92.52

605369

201-161-1

60ZTR74268

0760

30673

1695

DTXSID0021547

Liquid

29147000

Characteristics

17.1

0.28

Clear yellow to yellow-brown Liquid

1.123 g/cm3 @ Temp: 25 °C

-44.5 °C

119.7 °C

82 °F

1.397

Solubility in water, g/100ml at 20°C: 10

2-8°C

Vapour pressure, kPa at 25°C: 1.5

Relative vapour density (air = 1): 3.2

Oral-rat LD50: 100 mg/kg; Oral-Mouse LD50: 127 mg/kg

In case of heat, open flame, oxidant is combustible; in heat, it decomposes toxic phosgene; in sunlight, it decomposes toxic chloride gas

vol% in air: 3.4

Pungent odor

1.65e-05 atm-m3/mole|Henry's Law constant = 1.65X10-5 atm-cu m/mole at 25 °C

Dipole moment: 2.36 debyes in hexane|Specific gravity: 1.123 at 25 °C/4 °C; 1.135 at 15 °C/4 °C|Hydroxyl radical reaction rate constant = 3.7X10-13 cu cm/molec-sec at 25 °C (est)

Highly flammable. Water soluble.

Halogenated Organic Compounds

Highly Flammable

CHLOROACETONE turns dark and resinifies on prolonged exposure to light [Merck]. This occurred in a bottle during storage for two years on a shelf in diffused light. A few days after the bottle was moved, it exploded [Ind. Eng. News 9: 184(1931)]. Is stabilized by addition of 0.1% water or 0.1% CaCO3.

610 °C

Safety Information

I

6.1

UN 1695 6.1/PG 1

3

10-24/25-26-36/37/38-50/53

16-23-36/37/39-45-60-61-38-28A-26

UC0700000

T+,N,T,F,Xi

Treasury is ventilated, low temperature and dry; anti-open flame, anti-high temperature, stored and transported separately from food materials and oxidants

Irritant/Flammable/Toxic/Lachrymatory

Explosive after storage for a long time

Stable. Incompatible with strong oxidizing agents, strong bases. May discolour on exposure to light. STENCH.

P260-P273-P280-P284-P301 + P310-P302 + P350

H226-H301-H310 + H330-H315-H319-H335-H410

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. 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 soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

UN 1695

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. 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 ground and collect in low or confined areas (sewers, basements, tanks). 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 are lighter than water. (ERG, 2016)|Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 35 °C explosive vapour/air mixtures may be formed.|Flammable - 3rd degree

|Danger|H226 (65.94%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 367 companies from 13 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, P240, P241, P242, P243, P260, P262, P264, P270, P271, P280, P284, P301+P310, P301+P330+P331, P302+P350, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P310, P320, P321, P322, P330, P361, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. SPILL: See ERG Table 1 - Initial Isolation and Protective Action Distances on the UN/NA 1695 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 131 [Flammable Liquids - Toxic]: 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. 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. (ERG, 2016)

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)|It is recommended that direct contact with liquid and vapor be prevented through strict engineering controls and that air concentrations be kept below 1 ppm as a ceiling concentration.

Flammable when exposed to heat or flame, or oxidizers.

LEL: 3.4%; UEL: ?|Above 35 °C explosive vapor/air mixtures may be formed.|Old material can explode.|Explosive limits , vol% in air: 3.4-?

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources. /Chloroacetone, stabilized/|Wear positive pressure self contained breathing apparatus. Wear appropriate chemical protective gloves, boots and goggles. /Chloroacetone, stabilized/

Environmental considerations - land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Chloroacetone, stabilized/|Environmental considerations - water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Chloroacetone, stabilized/|Environmental considerations - air spill: Apply water spray to knock down vapors. /Chloroacetone, stabilized/

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. Do not use water. /Chloroacetone, stabilized/|Personnel protection: Avoid breathing vapors. Keep upwind ... Avoid bodily contact with the material ... Do not handle broken packages unless wearing appropriate personal protective equipment. /Chloroacetone, stabilized/|Evacuation: if material leaking (not on fire) consider evacuation from downwind area based on amount of material spilled, location, and weather conditions. /Chloroacetone, stabilized/|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.

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.|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Health: 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. 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. /Chloroacetone, stabilized/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. 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 ground and collect in low or confined areas (sewers, basements, tanks). 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 are lighter than water. /Chloroacetone, stabilized/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Chloroacetone, stabilized/|For more DOT Emergency Guidelines (Complete) data for 1-Chloro-2-propanone (9 total), please visit the HSDB record page.

Intensely irritating to eyes, skin, mucous membranes.

Remove all ignition sources. Evacuate danger area! Consult an expert! Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Collect leaking liquid in covered containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Store only if stabilized. Fireproof. Separated from strong oxidants and food and feedstuffs. Keep in the dark.

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

Lachrymation. The substance is severely irritating to the eyes, skin and respiratory tract.

NO open flames, NO sparks and NO smoking. Above 35 °C use a closed system, ventilation and explosion-proof electrical equipment.

STRICT HYGIENE!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

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

The major hazards encountered in the use and handling of 1-chloro-2-propanone stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal contact), exposure to this colorless, pungent-smelling liquid may occur from its use in the syntheses of chlorofluoroacetones, perfumes, antioxidants, drugs, insecticides, and vinyl compounds. Effects from exposure may include contact burns to the skin and eyes, nausea, bronchospasm, delayed pulmonary edema, and death. The ACGIH recommends a Ceiling limit of 1 ppm for this compounds. Adequate ventilation to control airborne levels is necessary. However, in activities or situations where over-exposure may occur, wear a self-contained breathing apparatus, and full chemical protective clothing specifically recommended by the shipper or producer. If contact should occur, immediately flush affected skin or eyes with running water for at least 15 minutes, and remove contaminated clothing and shoes at the site. While 1-chloro-2-propanone does not ignite easily, it may explode in the heat of a fire. Also, its thermal degradation may give rise to fumes of phosgene. Fires involving 1-chloro-2-propanone may be extinguished with dry chemical, CO2, Halon, water spray, standard or alcohol foam, and water spray or fog. Prolonged unstabilized storage of this substance may lead to an explosive decomposition product. 1-Chloro-2-propanone should be stored in cool, dark areas, away from sources of ignition and oxidizing materials. Small spills of 1-chloro-2-propanone may be taken up with sand or other noncombustible absorbent and placed into containers for later disposal. Large spills should be diked far ahead of the spill area to prevent 1-chloro-2-propanone from entering water sources and sewers. Before implementing land disposal of waste 1-chloro-2-propanone, consult with environmental regulatory agencies for guidance.

1-Chloro-2-propanone was identified in the spent chlorination liquor from bleaching of sulphite pulp at high lignin content and in bleaching of sulphite pulp at normal lignin content after oxygen treatment at 0.1 g/ton pulp(1).

RURAL/REMOTE: 1-Chloro-2-propanone in the ambient air of Jones State Forest, TX at a concentration of 1.0-2.6 ppb(1).

Toxicity

highly toxic

LD50 Rat oral 100 mg/kg|LD50 Rat ip 80 mg/kg|LC50 Rat inhalation 262 ppm/1 hr|LD50 Rat oral 127 mg/kg|For more Non-Human Toxicity Values (Complete) data for 1-Chloro-2-propanone (6 total), please visit the HSDB record page.

1-Chloro-2-propanone's production and use in the manufacturing of couplers for color photography, as an enzyme inactivator, intermediary in the manufacture of perfumes, antioxidants, drugs, insecticide formulations, as a selective solvent for separating diolefins, and as a proposed catalyst in tetraethyllead production(1) may result in its release to the environment through various waste streams(SRC). Its designation as a proposed tear gas for military and police use(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5(SRC), determined from a structure estimation method(2), indicates that 1-chloro-2-propanone is expected to have very high mobility in soil(SRC). Volatilization of 1-chloro-2-propanone from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.65X10-5 atm-cu m/mole(3). 1-Chloro-2-propanone is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 12 mm Hg at 25 °C(4). 1-Chloro-2-propanone will hydrolyze in moist soil, releasing hydrochloric acid which is related to its irritation as a lachrymator(5). Biodegradation data in soil were not available(SRC, 2010).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5(SRC), determined from a structure estimation method(2), indicates that 1-chloro-2-propanone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.65X10-5 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 and 19 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 0.02(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 1-Chloro-2-propanone will hydrolyze, releasing hydrochloric acid which is related to its irritation as a lachrymator(8). Hydrolysis rate constants at 25, 30 and 37 °C are 8X10-6, 2X10-5 and 6X10-5 /hr, respectively(9). Biodegradation data in water were not available(SRC, 2010).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-chloro-2-propanone, which has a vapor pressure of 12 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-chloro-2-propanone 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 44 days(SRC), calculated from its rate constant of 3.7X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1-Chloro-2-propanone 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 1-chloro-2-propanone with photochemically-produced hydroxyl radicals has been estimated as 3.7X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 44 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1-Chloro-2-propanone will hydrolyze releasing hydrochloric acid which is related to its irritation as a lachrymator(2). Hydrolysis rate constants at 25, 30 and 37 °C are 8X10-6, 2X10-5 and 6X10-5 /hr, respectively(3). 1-Chloro-2-propanone contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for 1-chloro-2-propanone(SRC), using an estimated log Kow of 0.02(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 a structure estimation method based on molecular connectivity indices(1), the Koc of 1-chloro-2-propanone can be estimated to be 5(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1-chloro-2-propanone is expected to have very high mobility in soil.

The Henry's Law constant for 1-chloro-2-propanone is 1.65X10-5 atm-cu m/mole(1). This Henry's Law constant indicates that 1-chloro-2-propanone 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 days(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 19 days(SRC). 1-Chloro-2-propanone's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 1-Chloro-2-propanone is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 12 mm Hg(3).

According to the 2006 TSCA Inventory Update Report, the number of workers reasonably likely to be exposed in the industrial manufacturing, processing, and use of 1-chloro-2-propanone is 1-99 persons; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 4354 workers (729 of these were female) were potentially exposed to 1-chloro-2-propanone in the US(1). Occupational exposure to 1-chloro-2-propanone may occur through inhalation and dermal contact with this compound at workplaces where 1-chloro-2-propanone is produced or used. Monitoring and use data indicate that the general population may be exposed to 1-chloro-2-propanone via inhalation of ambient air and contact with products containing 1-chloro-2-propanone(SRC).

Drug Information

Exptl Therapy: Antitumor agent against Walker 256 carcinoma in rats. Also antitumor agent against p388 lymphocytic leukemia and B-16 melanoma in mice.

... There is experimental animal evidence that chloroacetone is absorbed through the skin ....

Forms binary azeotropes with many organic liquids. Reacts with aryl Grignard reagents to form stilbenes.

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: 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. 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)

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)


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


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


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

/SRP:/ 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. /Ketones and related compounds/|/SRP:/ 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 ... . For 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. Administer activated charcoal ... . /Ketones and related compounds/|/SRP:/ 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 ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . 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. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ketones and related compounds/

/HUMAN EXPOSURE STUDIES/ Chloroacetone was extremely effective as a war gas ... A concn of 2.3 mg/L (605 ppm) was found to be lethal after 10 min and 0.1 mg/L (26 ppm) is intolerable after one min of exposure.|/SIGNS AND SYMPTOMS/ The first effect /is/ lacrimation (at approximately 5 ppm) followed by irritation of the upper resp tract and a burning sensation on exposed skin. ... More serious effects, such as pulmonary edema, do not occur at these low irritating concn. Even small amt in the eyes may result in permanent damage.|/CASE REPORTS/ An employee that received direct exposure to hot chloroacetone required hospitalization; the vapors were immediately irritating to the eyes and upper resp tract, and the hot liq was immediately irritating to the skin. The immediate erythema appeared to subside; however, about 8 hr after exposure, the exposed areas began to blister, and 24 hr post exposure the exposed area had blistered completely. All signs and symptoms disappeared within 7 days, and there was no evidence of pulmonary edema despite irritation to the upper resp tract.|/CASE REPORTS/ Of 25 individuals who reported to health services as a result of exposure to chloroacetone, 8 showed evidence of eye irritation, 7 had localized dermal irritation, 1 showed contact dermatitis, and 9 did not present any clinical sign of exposure.|/BIOMONITORING/ Blood and urine samples were collected in 1990 from 10 people working in four dry cleaning shops in Croatia, where trichloroethylene was used as the cleaning solvent. The concentration of trichloroethylene in the air was 25-40 ppm [134-215 mg/cu m]. The mean blood levels of trichloroethylene were 0.38 umol/L (50 ug/L) on Monday morning (range, 0.15- 3.58 umol/L) [20-70 ug/L] and 3.39 umol/L [445 ug/L] on Wednesday afternoon (range, 0.46- 12.71 umol/L [60-1670 ug/L].

1-chloropropanone

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

Sore throat. Cough. Burning sensation. Shortness of breath.


MAY BE ABSORBED! Redness. Pain. Blisters.


Redness. Watering of the eyes. Pain. Burns.

Chloroacetone Use and Manufacturing

Methods of Manufacturing

There are many synthetic methods for chloroacetone. The acetone chlorination method is currently one of the main methods used in domestic production. Chloroacetone is obtained by chlorination of acetone in the presence of acid binding agent calcium carbonate. Reaction equation: CH3COCH3[Cl2→[H2O, CaCO3]CH3COCH2Cl according to a certain feeding ratio, add acetone and calcium carbonate into the reactor, stir into a slurry, and heat to reflux. After stopping heating, let in chlorine gas for about 3 to 4 hours, and add water to dissolve the calcium chloride produced. The oil layer is collected, washed, dehydrated, and rectified to obtain the chloroacetone product.

Uses

Used as an intermediate in organic synthesis, used in the production of dyes, pesticides, drugs, fragrances, antioxidants, desiccants, vinyl photosensitive resins, color film coupling agents, etc.

Production

(1977) AT LEAST 4.54X10+7 G|(1982) PROBABLY GREATER THAN 4.54X10+6 G|2-Propanone, 1-chloro- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#2802]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 2-Propanone, 1-chloro-. Aggregated National Production Volume: < 500,000 lbs.

ESSENTIALLY 100 % AS A CHEMICAL INTERMEDIATE

5% CaCO3 added as a stabilizer. May contain ca. 5% 1,1-dichloroacetone and/or mesityl oxide.

2-Propanone, 1-chloro-: ACTIVE|Reactions of chlorine with ethylene, propylene, acrolein or paraffin under simulated atmospheric conditions, including UV irradition, gave a large number of products, some more toxic than the initial compounds, for example 1-chloro-2-propanone.

1-Chloro-2-propanone was detected in spent chlorination liquor following clean-up on XAD-4 resin followed by GC-MS analysis in the electron impact mode.

Fire Hazards -> Flammable - 3rd degree

Computed Properties

Molecular Weight:92.52
XLogP3:0.6
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:92.0028925
Monoisotopic Mass:92.0028925
Topological Polar Surface Area:17.1
Heavy Atom Count:5
Complexity:42.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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