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Acyl Halides, Sulfonyl Halides, and Chloroformates mixed with
Water and Aqueous Solutions

Hazard Predictions

• Corrosive: Reaction products may be corrosive
• Generates gas: Reaction liberates gaseous products and may cause pressurization
• Generates heat: Exothermic reaction at ambient temperatures (releases heat)
• Intense or explosive reaction: Reaction may be particularly intense, violent, or explosive
• Toxic: Reaction products may be toxic

BENZENESULFONYL CHLORIDE is insoluble and stable in cold water. It decomposes in hot water to produce corrosive and toxic hydrochloric acid and benzenesulfonic acid. Rate of reaction decreases as temperature decreases (The Merck Index, Rahway (NJ), Merck and Co. Inc., 11th ed. 1989).

2-FLUOROBENZOYL CHLORIDE decomposes in water to form HCl with generation of heat (National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina: NTP).

4-METHOXYBENZOYL CHLORIDE fumes in air and reacts exothermically with water (including moisture in air or soil) to form hydrochloric acid and insoluble anisic acid (The Merck Index, Rahway (NJ), Merck and Co. Inc., 11th ed. 1989).

ACETYL BROMIDE fumes in air and reacts violently with water producing heat and acidic fumes (Hazardous Chemical Data, NFPA 49, Boston, National Fire Protection Association, 1966). Acetyl bromide reacts vigorously with water to generate gaseous HBr (Brown, D. F., et al. (2000) Development of the Table of Initial Isolation and Protective Action Distances for the 2000 Emergency Response Guidebook, ANL/DIS-00-1, Argonne National Laboratory, Argonne IL).

ACETYL CHLORIDE is highly flammable and fumes in air. The compound reacts violently with water producing heat and acidic HCl (The Merck Index, Rahway (NJ), Merck and Co. Inc., 11th ed. 1989). Acetyl chloride reacts vigorously with water to generate gaseous HCl (Brown, D. F., et al. (2000) Development of the Table of Initial Isolation and Protective Action Distances for the 2000 Emergency Response Guidebook, ANL/DIS-00-1, Argonne National Laboratory, Argonne IL).

BENZENE PHOSPHORUS DICHLORIDE reacts with water, including moisture in air or soil, to liberate heat and hydrochloric acid (The Merck Index, Rahway (NJ), Merck and Co. Inc., 11th ed. 1989).

BROMOACETYL BROMIDE fumes in air and reacts violently with water to form hydrobromic acid (HBr) (U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office. http://www.uscg.mil/directives/cim/16000-16999/CIM_16465_12C.pdf).

CHLOROACETYL CHLORIDE reacts with moisture in the air or with water with generation of heat and hydrochloric acid (The Merck Index, Rahway (NJ), Merck and Co. Inc., 11th ed. 1989). In experiments at Argonne National Laboratory, in which it was mixed with water and stirred at room temperature and pressure, about 38 percent of the theoretical yield of HCl evolved as a gas in the first 20 minutes (Brown, D. F., et al. (2000) Development of the Table of Initial Isolation and Protective Action Distances for the 2000 Emergency Response Guidebook, ANL/DIS-00-1, Argonne National Laboratory, Argonne IL).

CHLOROETHYL CHLOROFORMATE decomposed slowly by water forming ethanol, HCl, and CO2; on contact with moist air, it gives off HCl fumes; attacks many metals especially in humid atmosphere (Handling 365bet娱乐 Safely, Dutch Association of Safety Experts, Dutch Chemical Industry Association, Dutch Safety Institute, 1980, p. 47).

CHLOROMETHYL CHLOROFORMATE reacts with water or with moisture in air to generate heat and hydrochloric acid fumes (The Merck Index, Rahway (NJ), Merck and Co. Inc., 11th ed. 1989).

CYCLOBUTYL CHLOROFORMATE reacts with water or with moisture in air to generate heat and hydrochloric acid fumes (The Merck Index, Rahway (NJ), Merck and Co. Inc., 11th ed. 1989).

M-NITROBENZOYL CHLORIDE decomposes in water and alcohol (National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina: NTP).

PHOSPHORUS OXYBROMIDE reacts slowly and exothermically with water to form phosphoric acid and hydrobromic acid (The Merck Index, Rahway (NJ), Merck and Co. Inc., 11th ed. 1989). Decomposes exothermically in water to form toxic fumes of hydrobromic and phosphoric acids (Lewis, R.J., Sr. 2000. Sax's Dangerous Properties of Industrial Materials, 10th Edition. New York: John Wiley & Sons, pp. 2957). In experiments at Argonne National Laboratory, in which it was mixed with water and stirred at room temperature and pressure, about 12 percent of the theoretical yield of HBr evolved as a gas in the first 30 minutes. This rate of gas production was slow enough that essentially all of the gas dissolved in the water as it was released, generating an aqueous hydrobromic acid solution instead of gaseous hydrogen bromide (Brown, D. F., et al. (2005) Development of the Table of Initial Isolation and Protective Action Distances for the 2004 Emergency Response Guidebook, ANL/DIS-05-2, Argonne National Laboratory, Argonne IL).

PHOSPHORUS OXYCHLORIDE fumes in air. The compound reacts exothermically with water to form fumes of phosphoric acid and hydrogen chloride. In experiments at Argonne National Laboratory, in which it was mixed with water and stirred at room temperature and pressure, about 21 percent of the theoretical yield of HCl evolved as a gas in the first 20 minutes (Brown, D. F., et al. (2000) Development of the Table of Initial Isolation and Protective Action Distances for the 2000 Emergency Response Guidebook, ANL/DIS-00-1, Argonne National Laboratory, Argonne IL).

PROPIONYL CHLORIDE vigorously reacts with water to form propionic acid and hydrochloric acid (The Merck Index, Rahway (NJ), Merck and Co. Inc., 11th ed. 1989).

SULFURYL CHLORIDE reacts with moist air to give strongly acidic mists that are heavier than air. It slowly reacts in water to give hydrochloric acid and sulfuric acid (Handling 365bet娱乐 Safely, Dutch Association of Safety Experts, Dutch Chemical Industry Association, Dutch Safety Institute, 1980, p. 881). In experiments at Argonne National Laboratory, in which it was mixed with water and stirred at room temperature and pressure, about 81 percent of the theoretical yield of HCl evolved as a gas in the first 20 minutes (Brown, D. F., et al. (2000) Development of the Table of Initial Isolation and Protective Action Distances for the 2000 Emergency Response Guidebook, ANL/DIS-00-1, Argonne National Laboratory, Argonne IL).

SULFURYL FLUORIDE reacts with moist air to give corrosive acid mists that are heavier than air. The compound decomposes with water forming hydrofluoric acid and sulfuric acid (Handling 365bet娱乐 Safely, Dutch Association of Safety Experts, Dutch Chemical Industry Association, Dutch Safety Institute, 1980, p. 881).

THIONYL CHLORIDE emits dense corrosive fumes in moist air. The compound violently reacts with water to liberate hydrochloric acid and sulfur dioxide (Hazardous Chemical Reactions, NFPA 491M, Quincy (MA), National Fire Protection Association, 10th ed., 1991). In experiments at Argonne National Laboratory, in which it was mixed with water and stirred at room temperature and pressure, the full theoretical yields of both HCl and SO2 gases were produced within the first 5 minutes (Brown, D. F., et al. (2000) Development of the Table of Initial Isolation and Protective Action Distances for the 2000 Emergency Response Guidebook, ANL/DIS-00-1, Argonne National Laboratory, Argonne IL).

VANADIUM OXYTRICHLORIDE fumes in air and reacts with moist air to form vanadic acid and hydrochloric acid fumes. The compound reacts exothermically with water to generate acidic fumes and acidic solutions. It is violently hygroscopic (Fire and Explosion Risks, von Schwartz, E., London, Griffin, 1918, p. 321).

Chlorosulfonic acid reacts exothermically and violently with water producing sulfuric acid, hydrochloric acid, and large quantities of dense white acid fumes. Contact with water and metal produces explosive hydrogen gas (The Merck Index, Rahway (NJ), Merck and Co. Inc., 11th ed. 1989; U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office. Available online at http://www.uscg.mil/directives/cim/16000-16999/CIM_16465_12C.pdf).

Chlorosulfonic acid is a source of very toxic fumes. It decomposes explosively on contact with water to generate gaseous HCl (Brown, D. F., et al. (2000) Development of the Table of Initial Isolation and Protective Action Distances for the 2000 Emergency Response Guidebook, ANL/DIS-00-1, Argonne National Laboratory, Argonne IL).

Chlorosulfonic acid and sulfur trioxide mixture fumes in air. Combines with water with explosive force (heat of dilution 504 cal/g) forming sulfuric acid (The Merck Index, Rahway (NJ), Merck and Co. Inc., 11th ed. 1989).

Potential Gas Byproducts

• Acid Fumes
• Carbon Dioxide (CO2)
• Hydrogen Sulfide (H2S)
• Hydrogen Sulfate (H2SO4)
• Hydrogen Chloride (HCl)
• Hydrogen Fluoride (HF)
• Hydrogen Iodide (HI)
• Hydrogen Halide (HX)
• Sulfur Dioxide (SO2)