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Hazard Predictions

• 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
• Polymerization hazard: Polymerization reaction may become intense and may cause pressurization

Hydrides react spontaneously and irreversibly with proton donors, including carboxylic acids, evolving flammable H2 gas (Rittmeyer, P., U. Wietelmann. 2002. Hydrides. In Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH & Co. KGaA. (Online)).

While powerful hydride reductants (e.g., LiAlH4 or AlH3) are generally needed to reduce carboxylic acids, reactions between carboxylic acids and diborane liberate hydrogen even if insufficient diborane is present to reduce the acid (Eggeman, T. 2001. Hydrides. In Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. (Online); Brown, H.C., W. Korytnyk. 1960. A Study of the Relative Reactivities of Representative Functional Groups towards Diborane. Journal of the American Chemical Society 82:3867).

Fluorinated carboxylic acids and amides can react violently with lithium aluminum hydride, potentially with ignition or gas evolution (Karo, W. 1955. Chemical and Engineering News 33:1368).

Complex metal hydrides can reduce carboxylic acids to aldehydes or alcohols, with evolution of H2 (Kohlpaintner, C., Schulte, M., Falbe, J., Lappe, P. and Weber, J. 2008. Aldehydes, Aliphatic. Ullmann's Encyclopedia of Industrial Chemistry. (Online)).

Sodium hydride reacts with carboxylic acids to form sodium carboxylate salts (Klemm, A., Hartmann, G. and Lange, L. 2000. Sodium and Sodium Alloys. Ullmann's Encyclopedia of Industrial Chemistry. (Online)).

Potential Gas Byproducts

• Alcohols
• Aldehydes
• Hydrogen (H2)