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| verifiedrevid = 372951397 |
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|ImageFile=Chlorendic acid.png |
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| verifiedrevid = 433354134 |
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|ImageSize=200px |
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| ImageFile=Chlorendic acid.png |
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|IUPACName=1,4,5,6,7,7-hexachlorobicyclo-hept-5-ene-2,3-dicarboxylic acid |
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| ImageSize=200px |
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|OtherNames=Chlorendic acid, HET acid, hexachloroentomethylenetetrahydrophthalic acid |
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| IUPACName=1,4,5,6,7,7-hexachlorobicyclo-hept-5-ene-2,3-dicarboxylic acid |
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|Section1= {{Chembox Identifiers |
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| OtherNames=Chlorendic acid, HET acid, hexachloroendomethylenetetrahydrophthalic acid |
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| CASNo=115-28-6 |
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|Section1={{Chembox Identifiers |
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| PubChem=8266 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=115-28-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = IAC1H0N39L |
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| PubChem=8266 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C19204 |
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| KEGG = C19204 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| SMILES=C1(C(C2(C(=C(C1(C2(Cl)Cl)Cl)Cl)Cl)Cl)C(=O)O)C(=O)O |
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| ChEBI = 76603 |
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| SMILES=C1(C(C2(C(=C(C1(C2(Cl)Cl)Cl)Cl)Cl)Cl)C(=O)O)C(=O)O |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 7968 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C9H4Cl6O4/c10-3-4(11)8(13)2(6(18)19)1(5(16)17)7(3,12)9(8,14)15/h1-2H,(H,16,17)(H,18,19) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = DJKGDNKYTKCJKD-UHFFFAOYSA-N |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>9</sub>H<sub>4</sub>Cl<sub>6</sub>O<sub>4</sub> |
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| Formula=C<sub>9</sub>H<sub>4</sub>Cl<sub>6</sub>O<sub>4</sub> |
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| MolarMass=388.84366 |
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| MolarMass=388.84366 |
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| MeltingPtC= 232 |
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|Section3= {{Chembox Hazards |
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'''Chlorendic acid''', or '''1,4,5,6,7,7-hexachlorobicyclo-hept-5-ene-2,3-dicarboxylic acid''', is a ] ] used in the synthesis of some ] and ]s.<ref name=":0">{{Cite web |last=PubChem |title=Chlorendic acid |url=https://pubchem.ncbi.nlm.nih.gov/compound/8266 |access-date=2022-11-25 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> It is a common breakdown product of several ] ]. |
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'''Chlorendic acid''', or '''1,4,5,6,7,7-hexachlorobicyclo-hept-5-ene-2,3-dicarboxylic acid''', is a ] used in the synthesis of some ] and ]s. It is a common breakdown product of several ] ]. |
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==Properties and identification== |
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==Properties and identification== |
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Chlorendic acid is a white crystalline material with chemical formula {{Carbon}}<sub>9</sub>{{Hydrogen}}<sub>4</sub>{{Chlorine}}<sub>6</sub>{{Oxygen}}<sub>4</sub>. It is also called HET acid, Hetron 92, Hetron 92C, hexachloro-''endo''-methylenetetrahydronaphthalic acid, 1,4,5,6,7,7-hexachloro-5-norbornene-2,3-dicarboxylic acid, and 1,4,5,6,7,7-hexachlorobicyclo-5-heptene-2,3-dicarboxylic acid. |
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Chlorendic acid is a white crystalline material with chemical formula {{chem2|C9H4Cl6O4}}. 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-5-heptene-2,3-dicarboxylic acid.<ref name=":0" /> |
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It is produced both as acid and as its ]. The anhydride has CAS number {{CASREF|CAS=115-27-5}}. |
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It is produced both as acid and as its ]. The anhydride has CAS number {{CASREF|CAS=115-27-5}}. |
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Chlorendic acid is slightly soluble in water and nonpolar organic solvents (eg. ], ], ]). It is easily soluble in slightly polar organic solvents (], ], ]). When heated, it loses water at 200 °C, forming an anhydride with melting point of 230-235 °C. When subject to ], it decomposes to hydrochloric acid and various chlorinated compounds. It is resistant to hydrolytic dechlorination. It readily forms salts with metals, and esters. |
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Chlorendic acid is slightly soluble in water and nonpolar organic solvents (e.g. ], ], ]). It is easily soluble in slightly polar organic solvents (], ], ]). When heated, it loses water at 200 °C, forming an anhydride with melting point of 230–235 °C. When subject to ], it decomposes to hydrochloric acid and various chlorinated compounds. It is resistant to hydrolytic dechlorination. It readily forms salts with metals, and esters. |
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==Chemistry and uses== |
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==Chemistry and uses== |
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Chlorendic acid is industrially produced in high volumes by ]. It is used as an intermediate in synthesis of unsaturated flame-retardant ] ]s and ]s, and as a finishing flame-retardant treatment for ]. A major use is in production of ]-reinforced resins for chemical industry equipment. It can be used to make ]s for use in special ]s and ]s. It is used as a hardening agent in ]s used in manufacture of ]s. When reacted with nonhalogenated ]s, it forms halogenated ]s used as ]s in ] ]s. it is also used for production of ] and ], which are used as reactive flame retardants in ]s. In limited amounts, it is used as an additive in ] ]. |
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Chlorendic acid is industrially produced in high volumes by the ]. It is used as an intermediate in synthesis of unsaturated flame-retardant ] ]s and ]s, and as a finishing flame-retardant treatment for ]. A major use is in the production of ]-reinforced resins for chemical-industry equipment. It can be used to make ]s for use in special ]s and ]s. It is used as a hardening agent in ]s used in the manufacture of ]s. When reacted with nonhalogenated ]s, it forms halogenated ]s that can be used as ]s in ]s. It is also used for producing ] and ], which are used as reactive flame retardants in ]s. In limited amounts, it is used as an additive in ] ]. |
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Esters and amine salts of chlorendic acid are used as ]s in synthetic ]s. |
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Esters and amine salts of chlorendic acid are used as ]s in synthetic ]s. |
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When used in polymers, whether as a curing agent or as a flame retardant, it bonds covalently to the polymer matrix, which reduces its ] to the environment. It may, however, be released when such materials are subjected to hydrolysis, and can be formed by oxidation of chlorinated cyclodiene insecticides (eg. ], ], ], ], ], ], and ]). Its half-life in ] is 140-280 days. |
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When used in polymers, whether as a curing agent or as a flame retardant, it bonds covalently to the polymer matrix, which reduces its ] to the environment. It may, however, be released when such materials are subjected to hydrolysis, and it can be formed by oxidation of chlorinated cyclodiene insecticides (e.g. ], ], ], ], ], ], and ]). Its half-life in ] is 140–280 days. |
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In Europe, 80% of chlorendic acid is used in production of flame-resistant composites for building and transportation, the rest is used in materials for corrosion-resistant fluid storage equipment. In the USA, Latin America, and Asia, 20-30% is used in flame retardant applications and the rest is used in corrosion-resistant plastics. |
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In Europe, 80% of chlorendic acid is used in the production of flame-resistant composites for building and transportation, while the rest is used in materials for corrosion-resistant fluid-storage equipment. In the USA, Latin America, and Asia, 20-30% is used in flame-retardant applications and the rest is used in corrosion-resistant plastics. |
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==References== |
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{{reflist}} |
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==External links== |
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