Adipyl chloride

Putrescine dihydrochloride has been prepared by the Hofmann degradation of adipamide 3.. s by the Curtius degradation of adipyl hydrazide through the urethane by the Curtius degradation of adipyl azide obtained from adipyl chloride and sodium azide by the Schmidt degradation of adipic acid with hydrogen azide by the reduction of succinonitrile, succinaldoxime, or 7-phthalimidobutyronitrile with sodium and from N-ben-zoyl-7-iodobutylamine ... 

In certain cases the organic dibasic acid is not sufficiently reactive for the purpose of polymerisation, and so it is replaced either with its anhydride or its acid chloride. For example polyamides (nylons) are often prepared by reaction of the acid chloride with the appropriate diamine. In the spectacular laboratory prepatation of nylon 6,6 this is done by interfacial polymerisation. Hexamethylenediamine is dissolved in water and adipyl chloride in a chlorinated solvent such as tetrachloromethane. The two liquids are added to the same beaker where they form two essentially immiscible layers. At the interface, however, there is limited miscibility and nylon 6,6 of good molar mass forms. It can then be continuously removed by pulling out the interface. 

Phenylbiguanide and stearoyl chloride are reported (236) to 5deld 5-phenylformoguanamine, and not 5-phenyl-6-heptadecylformoguana-mine, as would be expected from the general course of this reaction. The product of phenylbiguanide and adipyl chloride has been formulated (237) as the 5-phenyl- rather than the 6-phenyl-ditriazine. 

Diketones have been prepared by the Friedel-Crafts method. Both acyl chloride groups in adipyl chloride react with benzene in the presence of aluminum chloride to form the diketo compound, 1,4-dibenzoylbutane (81%). When diketene is treated with benzene under the conditions of the Friedel-Crafts reaction, benzoylacetone, COCHjCOCH, is formed... 

FIGURE 23.5 Hexamethylenedi-amine is dissolved in water (lower layer), and adipyl chloride, a derivative of adipic acid, is dissolved in hexane (upper layer). At the interface between the layers, nylon forms and is drawn out onto the stirring bar. 

The nylon can be drawn out and wound on a stirring rod. In industry, adipic acid is used in place of adipyl chloride. 

The reaction of BejjO(OCOCH )g with diacid chlorides (4 ) gives low molecular weight polymers. On heating, interchange occurred and BejjO(OCCH-), could be sublimed at 110-l40 C at 10 torr pressure for tne product derived from adipyl chloride. The use of terephthalyl chloride appears to Increase the stability of the product such that a temperature of 340 C was required to obtain sublimed beryllium acetate. Interchange also slowly occurs at room temperature. 

One mole (146 g.) of adipic acid (Coll. Vol. i, 18) previously dried over sulfuric acid in a vacuum is placed in a i-l. round-bottomed flask equipped with a condenser, and 357 g. (217 cc., 3 moles) of thionyl chloride is added at once. The mixture is heated gently on a water bath held at a temperature of 50-60°. After about four hours, solution is complete and evolution of hydrogen chloride has ceased. The flask is now connected to a downward condenser and heated under diminished pressure by a water bath to remove any excess of thionyl chloride. The light yellow residue of adipyl chloride is ready for use. 

A mixture of 300 g. (2.25 moles) of anhydrous aluminum chloride and 1500 cc. (17 moles) of benzene (dried over sodium and distilled) is placed in a 3-I. three-necked flask equipped with a mercury-sealed stirrer, a reflux condenser, and a dropping funnel. The reaction mixture is cooled in an ice bath and, with rapid stirring, the adipyl chloride is added through the dropping furmcl at an esen rate during the course of forty-five minutes (Note i). The reaction mixture darkens slowly but does not become black. After the adipyl chloride has been added, the... 

Dibenzoylbutane has been prepared by the action of aluminum chloride on a mixture of benzene and adipyl chloride or benzene and polymeric adipic anhydride. It has also been obtained as a by-product in the action of zinc and alcohol on a, /3-dibromopropiophenone. The melting points recorded are 102°, 105-106°, and ii2°. ... 

TABLE XIII Polythioesters from Adipyl Chloride and Dithiols"... 

The reaction to form nylon can be carried out at the interface of two immiscible liquid layers in a beaker. The bottom layer contains adipyl chloride,... 

Nylon is formed at the interface where hexamettiylenediamine (in the lower water layer) and adipoyl chloride (a derivative of adipic acid, in the npper hexane layer) react. The nylon can he drawn ont and wonnd on a stirring rod. In indnstiy, adipic acid is nsed in place of adipyl chloride. 

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