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Hazard Predictions

• Corrosive: Reaction products may be corrosive
• Flammable: Reaction products may be flammable
• Generates gas: Reaction liberates gaseous products and may cause pressurization
• Intense or explosive reaction: Reaction may be particularly intense, violent, or explosive
• Toxic: Reaction products may be toxic

Acetals, hemiacetals and ketals contain both alcohol- and ether-like functional groups, and so are expected to react similarly to both alcohols and ethers. Alcohols and ethers are incompatible with acid halides, forming flammable esters in some cases as well as HX gases, as documented below:

Acetyl chloride reacts with alcohols to form esters, releasing toxic HCl gas as a byproduct (Wagner, F.S., Jr. 2005. Acetyl Chloride. In Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. (Online)).

Acetyl bromide reacts violently with water, methanol, or ethanol, evolving toxic HBr gas (The Merck Index, Rahway (NJ), Merck and Co. Inc., 9th ed., 1976, pp. 11).

Phosgene reacts with alcohols, releasing toxic HCl gas as a byproduct (Dunlap, K.L. 2005. Phosgene. In Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. (Online)).

Reactions between acetyl chloride and ethanol may accelerate to explosion (Lewis, R.J., Sr. 1992. Sax's Dangerous Properties of Industrial Materials, 8th Edition. New York: Van Nostrand Reinhold. pp. 41).

Cyanuric chloride reacts violently with methanol (Association of British Chemical Manufacturers. 1961. Quarterly Safety Summary 31:40).

Alcohols react with SOCl2 to form toxic SO2 gas (Carey, F. A. Organic Chemistry, 5th Ed. New York, NY: McGraw Hill, Inc, 2003).

Alcohols react with acid halides to liberate toxic HX gases (Smith, P. A. S., Open-Chain Nitrogen Compounds, Vol. I. New York: W. A. Benjamin, Inc., 1965, pp. 264).

Sulfonyl chloride violently decomposes in diethyl ether, evolving toxic HCl gas (Dustan, I. et al. 1966. Chemistry and Industry 73).

Reactions between acyl halides and ethers are exothermic and may cause pressurization. Secondary and tertiary ethers are most likely to spontaneously react, particularly if catalyzed by a metal chloride (Koenst, W.M.B. 1981. Journal of Hazardous Materials 4:291-298).

Potential Gas Byproducts

• Hydrogen Halide (HX)
• Acid Fumes