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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
• 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

Heat of reaction between LiAlH4 and undiluted ethyl acetate may cause an explosion (Yardley, J.T., Chemistry and Industry, 1957, 433).

Carboxylic acid esters can be reduced to aldehydes or alcohols, depending on conditions, by complex hydrides such as LiAlH4, LiBH4, NaAlH4, or DIBAL (diisobutylaluminum hydride) (Kammermeier, B. 2000. Reduction. Ullmann's Encyclopedia of Industrial Chemistry. (Online)).

The reduction of esters to aldehydes is carried out with hydrides such as NaAlH4, LiAlH4, (C2H5)2NH, NaH2Al(OCH2CH2OCH3)2, or (i-C4H9)2AlH (Sakamuri, R. 2003. Esters, Organic. Kirk-Othmer Encyclopedia of Chemical Technology. (Online)).

The use of BH3 or LiAlH4BF3路O(C2H5)2 as a reducing agent converts esters to ethers (Sakamuri, R. 2003. Esters, Organic. Kirk-Othmer Encyclopedia of Chemical Technology. (Online)).

Esters can be reduced to alcohols with complex metal hydrides, especially lithium aluminum hydride (Riemenschneider, W. and Bolt, H. M. 2005. Esters, Organic. Ullmann's Encyclopedia of Industrial Chemistry (Online)).

Phosphonous diesters can be reduced to toxic, and potentially gaseous, phosphine derivatives with LiAlH4 (Corbridge, D.E.C. 1995. Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology, 5th Edition. Amsterdam: Elsevier).

Phosphate, phosphonic, and phosphinic esters can be reduced to phosphines with lithium aluminum hydride (Fee, D. C., Gard, D. R. and Yang, C.-H. 2006. Phosphorus Compounds. Kirk-Othmer Encyclopedia of Chemical Technology. (Online)).

Complex metal hydrides can reduce esters to aldehydes (Kohlpaintner, C., Schulte, M., Falbe, J., Lappe, P. and Weber, J. 2008. Aldehydes, Aliphatic. Ullmann's Encyclopedia of Industrial Chemistry. (Online)).

Some alkylzinc bromide compounds react violently with esters (Manual of Hazardous Chemical Reactions, NFPA 491M, Quincy (MA), National Fire Protection Association, 5th ed., 1975, p. 167).

NaH causes violent exothermic polymerization of ethyl 2,2,3-trifluoropropionate, possibly with production of toxic HF gas (Urben, P.G. 1995. Bretherick's Handbook of Reactive Chemical Hazards, 5th Edition. Oxford: Butterworth-Heinemann. pp. 1501).

Potential Gas Byproducts

• Alcohols
• Aldehydes
• Phosphine (PH3)