1,6-Hexanediamine polymerization using

Amidation. Heating of the diammonium salt or reaction of the dimethyl ester with concentrated ammonium hydroxide gives adipamide [628-94-4] mp 228°C, which is relatively insoluble in cold water. Substituted amides are readily formed when amines are used. The most industrially significant reaction of adipic acid is its reaction with diamines, specifically 1,6-hexanediamine. A water-soluble polymeric salt is formed initially upon mixing solutions of the two materials then hea ting with removal of water produces the polyamide, nylon-6,6. This reaction has been studied extensively, and the hterature contains hundreds of references to it and to polyamide product properties (31). 

If you react an organic acid with an amine, you split off water and form an amide. If you use an organic acid that contains two acid ends and an amine that has two amine ends (a diamine), then you can polymerize a poiyamide. The polyamide is commonly referred to as nylon. Figure 16-8 shows the reaction between 1,6-hexanediamine and adipic acid to form Nylon 66. (The 66 indicates that there are 6 carbon atoms in both the amine and the organic acid.)... 

The preparation of Nylon-6,10TM, rather than Nylon-6,6, has been chosen to illustrate step-growth polymerization for the present experiment. This polyamide is commercially produced from decanedioic acid (32) and 1,6-hexanediamine (30), as shown in Equation 22.16. To facilitate forming the polyamide under simple laboratory conditions, however, the diacid dichloride of 32 is used because it is more reactive toward diamine 30. Using the diacid dichloride means that the small molecule eliminated in this step-growth polymerization is hydrogen chloride rather than water (Eq. 22.17). Sodium carbonate is added to neutralize the acid formed to prevent consumption of the expensive diamine via an acid-base reaction. If the base were not added, an excess of diamine would be required for complete polymerization. 

Purpose. The polyamide, nylon, is prepared by the step-growth condensation polymerization of adipoyl chloride with 1,6-hexanediamine. An interfacial (emulsion) polymerization technique is used to generate nylon... 

C-DDP was licensed in 1980 under the trade name Platinol and is widely used in conjunction with other anticancer agents. The success of c-DDP initiated the synthesis and characterization of a number of structural analogs for potential anticancer activity. In 1974, Carraher and Scott synthesized numerous polymeric derivatives of form [3] Included in the diamines used was 1, 6-hexanediamine. 

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