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Ethers mixed with
Metal Hydrides, Metal Alkyls, Metal Aryls, and Silanes

Hazard Predictions

• Corrosive: Reaction products may be corrosive
• Explosive: Reaction products may be explosive or sensitive to shock or friction
• Flammable: Reaction products may be flammable
• 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

Butyllithium reacts with ethers to produce flammable low molecular weight hydrocarbon gases and water soluble lithium alkoxides (Kamienski, C.W. et al. 2001. Lithium and Lithium Compounds. In Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. (Online)).

Solutions of borane in THF build up pressure over time above 0 C, possibly due to the formation of H2 gas from interaction with NaBH4 stabilizer (Gaines, D.F. et al. 1963. Inorganic Chemistry 2:526).

Mixture of THF and CaH2 may explode if heated (Halonbrenner, R. et al. 1978. Chemical and Engineering News 56(6):3).

Distillation of dioxane and LiAlH4 may result in explosion and fire (Urben, P.G. 1995. Bretherick's Handbook of Reactive Chemical Hazards, 5th Edition. Oxford: Butterworth-Heinemann. pp. 47).

THF can react explosively with NaAlH4 if the solution is not properly stirred (i.e. the mixture gets too concentrated) (Del Giudia, F.P. et al. 1961. Chemical and Engineering News E9(40):57).

Lithium aluminum hydride may ignite on contact with 1,2-dimethoxyethane (MCA Case History No. 1182, Case Histories of Accidents in the Chemical Industry, Manufacturing Chemists' Association, Washington).

Dimethyl ether reacts violently with hydrides (Lewis, R.J., Sr. 1992. Sax's Dangerous Properties of Industrial Materials, 8th Edition. New York: Van Nostrand Reinhold. pp. 2317).

Dioxane forms solids with triethynyl aluminum that are explosive when dry (Chini, P. et al. 1962. Chim. e Ind. (Milan) 44:1220).

Diethyl ether reacts vigorously with both triethynyl aluminum and trimethyl aluminum (Methoden der Organischen Chemie; Muller, E. (Ed.); Stuttgart, Thieme, 1970, Vol. 13.4, p. 159; Lewis, R.J., Sr. 1992. Sax's Dangerous Properties of Industrial Materials, 8th Edition. New York: Van Nostrand Reinhold. pp. 1614).

Lithium alkyls react exothermically with ethyl ether to give saturated and unsaturated hydrocarbons and lithium alkoxide (Dickinson, F. 1961. Mellor's Comprehensive Treatise on Inorganic and Theoretical Chemistry. Vol. 2, Supplement 2, p. 91. Longmans, Green and Co Ltd.; MCA Safety Data Sheet 91, Manufacturing Chemists' Association, Washington, 1966).

The mixture of trimethylthallium and diethyl ether explodes at 0C (Leleu, J., Cahiers de Notes Documentaires, 1977, (88), 371).

Triphenylchromium tetrahydrofuranate (Ph3Cr * 3C4H8O) reacts with diethylether to form a black pyrophoric material (Bailar, J. C., Emeleus, H. J., Nyholm, R. S., Trotman-Dickenson, A. F., (Eds.). 1973. Comprehensive Inorganic Chemistry. Oxford, Pergamon. Vol. 4, 974).

Ethylmagnesium iodide reacts violently with ethoxyacetylene if the reaction mixture is not adequately diluted (Jordan, C. F., Chem. Eng. News, 1966, 44(8), 40).

3-Trifluoromethylphenylmagnesium bromide in diethylether decomposes violently if heated above 75C ('Benzotrifluorides Catalog 6/15' West Chester (Pa)., Marshallton Res. Labs., 1971).

Potential Gas Byproducts

• Hydrogen (H2)
• Hydrocarbons