Description
It was firstly produced by nitric acid oxidation of cork (Latin suber) material and then from castor oil. The oxidation of ricinoleic acid produces, by splitting at the level of the double bond and at the level of the OH group, at the same time, suberic acid (octanedioic acid) and the next homologue azelaic acid. Suberic acid was used in the manufacture of alkyd resins and in the synthesis of polyamides leading to nylon.
Chemical Properties
off-white crystalline powder
Uses
In the plastics industry.
Uses
Suberic Acid is used in the preparation of reduction-sensitive micelles affecting their cellular uptake. This has potential application in delivery of anticancer drugs. It is also used in the fluorescent detection of amidinium-carboxylate and amidinium formation.
Definition
ChEBI: An alpha,omega-dicarboxylic acid that is the 1,6-dicarboxy derivative of hexane.
Reactions
Suberic acid is an essential chemical widespread in softwood trees' trunk. Can there be reactions such as esterification, carboxylic acid halides, amidation and reduction in suberic acid, generation pyrolysis is heated. Its main application is to react with dibasic alcohol and diamine, produce polyester and polymeric amide, and also for organic synthesis.
Synthesis Reference(s)
Journal of the American Chemical Society, 81, p. 3677, 1959
DOI: 10.1021/ja01523a046
Synthesis
Industrial is to be obtained by Viscotrol C or ricinolic acid or cyclooctane oxidation, conventionally using 50% sulfuric acid to carry out catalysis. Suberic acid also can be oxidized and obtained by cyclooctene. A method for preparing suberic acid through cyclooctene oxidation comprises the following steps: mixing tetra-allkylammonium perrhenate and alkyl-imidazolim disulfate ionic liquid in a certain proportion to form a composite phase transfer catalyst and meanwhile carrying out catalytic oxidation reaction on cyclooctene in the presence of alkyl-imidazolim disulfate ionic liquid serving as a reaction solvent and a hydrogen peroxide solution serving as an oxidizing agent, wherein the reaction temperature is 40-70 DEG C, the pressure is normal, and the reaction time is 0.5-4 hours. After the reaction, the gas chromatography detection shows that the conversion rate of the cyclooctene is above 90%, and the cyclooctene yield is above 60%.
Purification Methods
Crystallise it from acetone. It sublimes at 300o without decomposition. [Beilstein 2 IV 2028.]
