Chapter 17 - Dicarboxylic Acids and Related Compounds

Abstract

Publisher Summary The acids in the series of alkanedicaxboxylic acids contain two carboxyl groups and are therefore, dibasic. The physical properties of the dicarboxylic acids in the solid state, for example, melting point, refractive index, solubility and so on, show pronounced alternation on ascending the series so that higher members tend to resemble the monocarboxylic acids and paraffins as the carboxyl group exerts proportionately less influence on the molecule as a whole. Such alternation, particularly with melting points, is also shown by polyesters and polyamides formed by reacting the dicarboxylic acids with diols and diamines of low molecular weight, but is absent with diesters such as the diethyl esters. In this chapter, general methods of preparation of dicarboxylic acids are discussed focusing on individual members, such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and their derivatives. Properties and typical reactions are also presented in detail. Structurally the mono-olefinic dicarboxylic acids are similar to the alkanedicarboxylic acids, except that they have a double bond either in the main chain among the carboxyl groups, or in a side chain. As a part of the discussion, maleic acid and fumaric acid, and their derivatives are also compared and contrasted on the basis of their typical reactions.