In organic chemistry, acidic hydrolysis is a hydrolysis process in which a protic acid is used to catalyze the cleavage of a chemical bond via a nucleophilic substitution reaction, with the addition of the elements of water (H2O).[1] For example, in the conversion of cellulose or starch to glucose.[2][3] For the case of ester hydrolysis and amides, it can be defined as an acid catalyzed nucleophilic acyl substitution reaction.[4] Carboxylic acids can be produced from acid hydrolysis of esters.[5]

The term is also applied to certain nucleophilic addition reactions, such as in the acid catalyzed hydrolysis of nitriles to amides. Acid hydrolysis does not usually refer to the acid catalyzed addition of the elements of water to double or triple bonds by electrophilic addition as may originate from a hydration reaction.

Acid hydrolysis is used to prepare monosaccharide with the help of acids, such as:[6]

Acid hydrolysis can be utilized in the pretreatment of cellulosic material, so as to cut the interchain linkages in hemicellulose and cellulose.[7]

See also

References

  1. ↑ Speight, James G. (2 November 2016). Hydrolysis. pp. 143–144. ISBN 9780128006689. in Speight, James G. (2017). "Industrial Organic Chemistry". Environmental Organic Chemistry for Engineers. pp. 87–151. doi:10.1016/B978-0-12-804492-6.00003-4. ISBN 978-0-12-804492-6.
  2. ↑ Goldstein, Irving S. (1983). "Hydrolysis of Cellulose by Acids". Biomass Utilization. pp. 559–566. doi:10.1007/978-1-4757-0833-2_30. ISBN 978-1-4757-0835-6.
  3. ↑ US 5726046, Farone, William A. & Cuzens, John E., "Method of producing sugars using strong acid hydrolysis", published 1998-03-10, assigned to Arkenol Inc.
  4. ↑ Vaughn, H. L.; Robbins, M. D. (April 1975). "Rapid procedure for the hydrolysis of amides to acids". The Journal of Organic Chemistry. 40 (8): 1187–1189. doi:10.1021/jo00896a050.
  5. ↑ "5.4: Hydrolysis Reactions". Chemistry LibreTexts. 2021-08-04. Retrieved 2023-10-07.
  6. ↑ Chen, Hongzheng (2015). Lignocellulose Biorefinery Engineering. Woodhead Publishing. ISBN 978-0-08-100135-6.
  7. ↑ Pandey; Larroche; Ricke; Dussap; Gnansounou (2011). Biofuels: Alternaative Feedstocks and Conversion Processes. Academic press. ISBN 978-0-12-385099-7.
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