Hexahydrophthalic anhydride

Chemical properties

White crystalline powder

The Uses of Hexahydrophthalic anhydride

Intermediate for alkyds, plasticizers, insect repellents, and rust inhibitors; hardener in epoxy resins.

The Uses of Hexahydrophthalic anhydride

HPPA, in combination with triethaylamine (TEA), can be used as a polymerization initiator in the preparation of polyester based resins. It can also be used as a hardener to cure 1,4-butanediol diglycidyl ether which can be used as an epoxy based system for electronic devices.

Definition

ChEBI: A cyclic dicarboxylic anhydride that is the cyclic anhydride of hexahydrophthalic acid.

What are the applications of Application

Predominantly cis 1,2-cyclohexanedicarboxylic anhydride (HHPA) is a cyclic anhydride that can be used for a variety of applications such as: plasticizer, rust inhibitor, and a curing agent for epoxy based resins.
HPPA, in combination with triethaylamine (TEA), can be used as a polymerization initiator in the preparation of polyester based resins. It can also be used as a hardener to cure 1,4-butanediol diglycidyl ether which can be used as an epoxy based system for electronic devices.

General Description

Predominantly cis 1,2-cyclohexanedicarboxylic anhydride (HHPA) is a cyclic anhydride that can be used for a variety of applications such as: plasticizer, rust inhibitor, and a curing agent for epoxy based resins.

Hazard

Toxic by inhalation, strong irritant to eyes and skin.

Flammability and Explosibility

Non flammable

Synthesis

Hexahydrophthalic anhydride is obtained by reacting ciscyclohexane-1, 2-dicarboxylic acid with oxalyl chloride.Combine ciscyclohexane-1, 2-dicarboxylic acid (1 mmol, 172 mg) and oxalyl chloride (1.2 mmol, 152 mg, 0.103 ml) in dry toluene (5 mL) and add a drop of freshly distilled DMF. Purge the reaction vessel with argon and heat the reaction under stirring for 3 h. Stop the stirring, decant the toluene solution and filter. Evaporate the volatiles. Transform into crystalline form by trituration with diethyl ether. 1H NMR (400 MHz, CDCl3) |? 3.18 - 3.12 (m, 2H 2CH) 1.96 - 1.83 (m, 4H 2CH2) 1.57 - 1.49 (m, 4H 2CH2). HRMS (ESI), calcd for C8H10NaO3 [M+Na]+ 175.0522, found 175.0527; calcd for C9H14NaO4 [M+CH3 OH+Na]+ 209.0784, found 209.0788.

Fig The synthetic method of Hexahydrophthalic anhydride.

Purification Methods

It has been obtained by heating the trans-acid or anhydride at 200o. Crystallise it from *C6H6/Et2O or distil it. [Kohler & Jansen J Am Chem Soc 60 2145 1938, Abell J Org Chem 22 769 1957, Beilstein 17 II 452, 17 III/IV 5931.]