Bicarbonate-catalyzed hydrolysis of hexamethylene diisocyanate to 1,6-diaminohexane. 1991

M Berode, and B Testa, and H Savolainen
Institute of Occupational Health Sciences, University of Lausanne, Switzerland.

The hydrolysis of hexamethylene diisocyanate (HDI) in water was tested in a dynamic and stationary system. Without catalysts, the reaction was very slow (less than 1% in 10 min at 30 degrees C) while the addition of simple carboxylic-acid-containing neutral buffers markedly catalyses the formation of 1,6-diaminohexane as the known hydrolysis product. The catalytic efficiency of formic acid, oxalic acid, acetic acid, lactic acid, citric acid and carbonic acid increased in this order while phosphate, glycine and glutamate were inactive even at very high concentrations. A 20 mM bicarbonate buffer was the optimal catalyst, but below this concentration the rate of HDI hydrolysis was drastically reduced. It is suggested that the hydrolysis of inhaled HDI in the lungs may be catalysed by bicarbonate in the blood, giving rise to amines found as urinary metabolites following occupational exposure.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D002021 Buffers A chemical system that functions to control the levels of specific ions in solution. When the level of hydrogen ion in solution is controlled the system is called a pH buffer. Buffer
D002264 Carboxylic Acids Organic compounds containing the carboxy group (-COOH). This group of compounds includes amino acids and fatty acids. Carboxylic acids can be saturated, unsaturated, or aromatic. Carboxylic Acid,Acid, Carboxylic,Acids, Carboxylic
D002951 Citrates Derivatives of CITRIC ACID.
D003485 Cyanates Organic salts of cyanic acid containing the -OCN radical. Cyanate
D003959 Diamines Organic chemicals which have two amino groups in an aliphatic chain. Diamine
D006868 Hydrolysis The process of cleaving a chemical compound by the addition of a molecule of water.
D001639 Bicarbonates Inorganic salts that contain the -HCO3 radical. They are an important factor in determining the pH of the blood and the concentration of bicarbonate ions is regulated by the kidney. Levels in the blood are an index of the alkali reserve or buffering capacity. Bicarbonate,Bicarbonate Ions,Hydrogen Carbonates,Bicarbonate Ion,Carbonic Acid Ions,Hydrogen Carbonate,Carbonate, Hydrogen,Carbonates, Hydrogen,Ion, Bicarbonate,Ions, Bicarbonate,Ions, Carbonic Acid
D017953 Isocyanates Organic compounds that contain the -NCO radical. Isocyanate
D019343 Citric Acid A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability. Citrate,Anhydrous Citric Acid,Citric Acid Monohydrate,Citric Acid, Anhydrous,Uralyt U

Related Publications

M Berode, and B Testa, and H Savolainen
August 2010, The Annals of occupational hygiene,
M Berode, and B Testa, and H Savolainen
January 1995, International archives of occupational and environmental health,
M Berode, and B Testa, and H Savolainen
May 2011, Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals,
M Berode, and B Testa, and H Savolainen
June 2000, Toxicological sciences : an official journal of the Society of Toxicology,
M Berode, and B Testa, and H Savolainen
December 2022, Chemical research in toxicology,
M Berode, and B Testa, and H Savolainen
January 2011, Journal of environmental monitoring : JEM,
M Berode, and B Testa, and H Savolainen
January 1989, The Annals of occupational hygiene,
M Berode, and B Testa, and H Savolainen
August 1982, Analytical chemistry,
M Berode, and B Testa, and H Savolainen
December 1983, Scandinavian journal of work, environment & health,
Copied contents to your clipboard!