Sebacoyl dichloride

Preparation of Polyamide-6,10 from Hexamethylenediamine and Sebacoyl Dichloride in Soiution and by Interfacial Polycondensation... 

Sebacoyl dichloride is obtained as follows 20 g of sebacoic acid and 50 g of thionyl chloride are refluxed on a water bath for 2 h.The excess thionyl chloride is then distilled off and the sebacoyl dichloride fractionated in vacuum (bp 142 °C/2 torr). 

A solution of 3 ml (14 mmol) of freshly distilled sebacoyl dichloride (for preparation see above) in 100 ml of carbon tetrachloride is placed in a 250 ml beaker. A solution of 4.4 g (38 mmol) of hexamethylenediamine in 50 ml of water is carefully run on to the top of this solution, using a pipette. (The aqueous solution can be made more readily visible by coloring it with a few drops of phenolphthalein solution.) A polyamide film is immediately formed at the interface and can be pulled out from the center with tweezers or clamps and laid over some glass rods it can now be pulled out continuously in the form of a hollow thread and wound up on to a spool driven by a slow-running motor. The polycondensation comes rapidly to a standstill if the motor is stopped, but immediately recommences, even after some hours, when the motor is restarted. 

The bifunctional reagent sebacoyl dichloride has been used to convert alcohols to acid chlorides, which, at pH 8.5, react readily with proteins. This procedure was used by Bailey and Butler to prepare a cholesterol-protein conjugate. 

Table 17-6. Dependence of the Intrinsic Viscosity [ry] on the Partition Coefficients PC of Hexamethylene Diamine in the Interfacial Poly condensation with Sebacoyl Dichloride...

In 1997, Taki et al. prepared two in-chain polymers by reacting a mixture of Ca) bisphenol (5) with an equimolar amount of dibasic acid dichloride (sebacoyl dichloride or a 1 1 mixture of isophthaloyl chloride/terephthaloyl chloride) at room temperature to afford linear main chain-polyesters 7a, b, which are soluble in DMF (Scheme 2.3) [12]. 

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