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Formic acid is principally used as a preservative antibacterial agent in livestock feed, in dying textiles, tanning leather and electroplating. In the poultry industry, it is sometimes added with feed to kill E. coli bacteria. It acts as a reducing agent for the catalytic reduction of nitrate in water.
Cleaves trityl groups selectively in the presence of benzylidene acetals or TBDMS ethers: Tetrahedron Lett., 27, 579 (1986).
Instead of the unstable formic anhydride, formylations may be carried out with formic acid and acetic anhydride to generate the mixed acetic formic anhydride in situ. For a review, see: Tetrahedron, 46, 1081 (1990). This reagent has been used for the deoxygenation of tertiary amine oxides: Chem. Lett., 1517 (1985).
Dehydration with sulfuric acid can be used to generate CO in situ. Subsequent reaction with tertiary carbocations gives the corresponding carboxylic acid (the Koch-Haaf carboxylation). For examples, see: Org. Synth. Coll., 5, 20, 739 (1973); improved procedure: Synth. Commun., 19, 1945 (1989). 1,4-Diols in which one alcohol is tertiary give -lactones: Chem. Lett., 1187 (1982).
Used in combination with formaldehyde in the Eschweiler-Clarke reductive methylation of amines, the formic acid acting as a hydride donor. Review: Org. React., 5, 290 (1949). For an example, see: Org. Synth. Coll., 3, 723 (1955).
In the presence of Raney nickel alloy, reduces aromatic nitriles to aldehydes in high yield: J. Chem. Soc., 5775 (1965); for list of examples, see: Org. Synth. Coll., 6, 631 (1988).
Hydrogen donor, in combination with Pd on carbon, in catalytic transfer hydrogenations; see, e.g.: Selective reduction of dinitroarenes to nitroanilines: J. Org. Chem., 45, 4992 (1980). Dehalogenation of aryl halides: Synthesis, 876 (1982). Hydrogenation of aromatic rings: Tetrahedron Lett., 33, 7477 (1992). See also Palladium, A12012, Cyclohexene, A11359, and Ammonium formate, A10699. For a comparative mechanistic study of formic acid and formate salts in hydrogenolysis of aryl chlorides, see: J. Org. Chem., 60, 1347 (1995).
In combination with Selenium(IV) oxide, 12358, improved results have been obtained in the allylic oxidation of sterically-hindered olefins: Synth. Commun., 24, 29213 (1994).
Rhee, Y. W.; Ha, S. Y.; Masel, R. I. Crossover of formic acid through Nafion membranes. J. Power Sources 2003, 117 (1), 35-38.
Jayashree, R. S.; Spendelow, J. S.; Yeom, J.; Rastogi, C.; Shannon, M. A.; Kenis, P. J. A. Characterization and application of electrodeposited Pt, Pt/Pd, and Pd catalyst structures for direct formic acid micro fuel cells. Electrochim. Acta 2005, 50 (24), 4674-4682.
Gefahrenhinweise (EU): H226-H302-H331-H314-H318
Flammable liquid and vapour. Harmful if swallowed. Toxic if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.