1,4,5,6,7,7-hexachloro-5-norbornene-2,3-dicarboxylic acid

Structural formula
General
Surname	1,4,5,6,7,7-hexachloro-5-norbornene-2,3-dicarboxylic acid
other names	Chlorenedioic acid; Hexachloro-endomethylenetetrahydrophthalic acid; HET acid;
Molecular formula	C 9 H 4 Cl 6 O 4
Brief description	white solid
External identifiers / databases
EC number	204-078-9
ECHA InfoCard	100.003.708
PubChem	8266
Wikidata	Q1854296
properties
Molar mass	388.84 g mol −1
Physical state	firmly
Melting point	239-242 ° C
solubility	poorly soluble in water (0.35 g l −1 at 25 ° C); poorly soluble in non-polar organic solvents (e.g. benzene ); readily soluble in methanol , ethanol and acetone ;
safety instructions
H and P phrases	H: 318-351
	P: 280-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,4,5,6,7,7-hexachloro-5-norbornene-2,3-dicarboxylic acid is a chemical compound from the group of carboxylic acids and hexachloronorbornenes. The anhydride of the compound is 1,4,5,6,7,7-hexachloro-8,9,10-trinorborn-5-ene-2,3-dicarboxylic anhydride and structurally with chlorinated cyclodiene insecticides such as aldrin , dieldrin , endrin , isodrin , Endosulfan , chlordane and heptachlor related.

Extraction and presentation

1,4,5,6,7,7-hexachloro-5-norbornene-2,3-dicarboxylic acid can be obtained by a Diels-Alder reaction of hexachlorocyclopentadiene with maleic anhydride and subsequent hydrolysis of the anhydride formed.

properties

1,4,5,6,7,7-hexachloro-5-norbornene-2,3-dicarboxylic acid is a white crystalline solid which, when heated, begins to decompose to anhydride before the melting point is reached. The compound is very resistant to hydrolytic dechlorination, easily forms salts with a wide variety of metals. It forms esters when heated with or without azeotropic solvents (e.g. chlorobenzene ) and easily forms alkyl-type polyester resins by reaction with glycols and other polyols .

use

1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic acid is used as an intermediate for the production of polyester resins and as a flame retardant .

Individual evidence

↑ ^a ^b ^c ^d ^e Environmental Health Criteria (EHC) for Chlorendic acid and anhydride , accessed June 20, 2018.
↑ ^a ^b ^c ^d ^e data sheet 1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic acid, 99% from Sigma-Aldrich , accessed on June 20, 2018 ( PDF ).
↑ ^a ^b ^c ^d ^e Entry on chlorendic acid in the Hazardous Substances Data Bank , accessed on June 12, 2018.

[inchem.org-1] Environmental Health Criteria (EHC) for Chlorendic acid and anhydride , accessed June 20, 2018.

[Sigma-2] ↑ ^a ^b ^c ^d ^e data sheet 1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic acid, 99% from Sigma-Aldrich , accessed on June 20, 2018 ( PDF ).

[HSDB-3] Entry on chlorendic acid in the Hazardous Substances Data Bank , accessed on June 12, 2018.