Chlorendic acid, or 1,4,5,6,7,7-hexachlorobicyclo
.2.1hept-5-ene-2,3-dicarboxylic acid, is a
chlorinated hydrocarbon
An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalently bonded atom of chlorine. The chloroalkane class (alkanes with one or more hydrogens substituted by chlo ...
used in the synthesis of some
flame retardants
The term flame retardants subsumes a diverse group of chemicals that are added to manufactured materials, such as plastics and textiles, and surface finishes and coatings. Flame retardants are activated by the presence of an ignition source a ...
and
polymer
A polymer (; Greek '' poly-'', "many" + ''-mer'', "part")
is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...
s.
It is a common breakdown product of several
organochlorine
An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalent bond, covalently bonded atom of chlorine. The chloroalkane class (alkanes with one or more hydrogens subst ...
insecticides
Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed to b ...
.
Properties and identification
Chlorendic acid is a white crystalline material with chemical formula . It is also called HET acid, hexachloroendomethylenetetrahydrophthalic acid, 1,4,5,6,7,7-hexachloro-5-norbornene-2,3-dicarboxylic acid, and 1,4,5,6,7,7 hexachlorobicyclo
.2.15-heptene-2,3-dicarboxylic acid.
It is produced both as acid and as its
anhydride
An organic acid anhydride is an acid anhydride that is an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the pa ...
. The anhydride has CAS number .
Chlorendic acid is slightly soluble in water and nonpolar organic solvents (e.g.
benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
,
hexane
Hexane () is an organic compound, a straight-chain alkane with six carbon atoms and has the molecular formula C6H14.
It is a colorless liquid, odorless when pure, and with boiling points approximately . It is widely used as a cheap, relatively ...
,
carbon tetrachloride
Carbon tetrachloride, also known by many other names (such as tetrachloromethane, also IUPAC nomenclature of inorganic chemistry, recognised by the IUPAC, carbon tet in the cleaning industry, Halon-104 in firefighting, and Refrigerant-10 in HVAC ...
). It is easily soluble in slightly polar organic solvents (
ethanol,
methanol
Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...
,
acetone). When heated, it loses water at 200 °C, forming an anhydride with melting point of 230–235 °C. When subject to
pyrolysis, it decomposes to hydrochloric acid and various chlorinated compounds. It is resistant to hydrolytic dechlorination. It readily forms salts with metals, and esters.
Chemistry and uses
Chlorendic acid is industrially produced in high volumes by the
Diels-Alder reaction. It is used as an intermediate in synthesis of unsaturated flame-retardant
polyester
Polyester is a category of polymers that contain the ester functional group in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include natural ...
resins and
plasticizers, and as a finishing flame-retardant treatment for
wool. A major use is in the production of
fiberglass-reinforced resins for chemical-industry equipment. It can be used to make
alkyd resins for use in special
ink
Ink is a gel, sol, or solution that contains at least one colorant, such as a dye or pigment, and is used to color a surface to produce an image, text, or design. Ink is used for drawing or writing with a pen, brush, reed pen, or quill. Thi ...
s and
paint
Paint is any pigmented liquid, liquefiable, or solid mastic composition that, after application to a substrate in a thin layer, converts to a solid film. It is most commonly used to protect, color, or provide texture. Paint can be made in many ...
s. It is used as a hardening agent in
epoxy resin
Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also coll ...
s used in the manufacture of
printed circuit board
A printed circuit board (PCB; also printed wiring board or PWB) is a medium used in Electrical engineering, electrical and electronic engineering to connect electronic components to one another in a controlled manner. It takes the form of a L ...
s. When reacted with nonhalogenated
glycols, it forms halogenated
polyols that can be used as
flame retardants in
polyurethane foams. It is also used for producing