Chlorendic anhydride is used in the synthesis of polymers, used in production of fiberglass-reinforced resins for chemical industry equipment.
Chlorendic anhydride can be used to make alkyd resins for use in special inks and paints.
Chlorendic anhydride is used as a hardening agent in epoxy resins used in manufacture of printed circuit boards
CAS Number: 115-27-5
EC Number: 204-077-3
Molecular Formula: C₉H₂Cl₆O₃
Molecular Weight: 370.83 g/mol
SYNONYMS:
Chlorendic Anhydride, HET Anhydride, Chloran 542, 1,4,5,6,7,7-Hexachloro-8,9,10-trinorborn-5-ene-2,3-dicarboxylic anhydride, Hexachloroendomethylenetetrahydrophthalic Anhydride, 4,7-Methanoisobenzofuran-1,3-dione, 4,5,6,7,8,8-hexachloro-3a,4,7,7a-tetrahydro-, 5-Norbornene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-hexachloro-, Chloran 542, Hexachloro-5-norbornene-2,3-dicarboxylic anhydride, Hexachloroendomethylene tetrahydrophthalic anhydride, HET Anhydride, 1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-Hexachlorobicyclo [2.2.1]hept-5-ene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]-5-heptene-2,3-dicarboxylic acid anhydride, Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-hexachloro-, NSC 22229, 1,4,5,6,7,7-hexachloro-8,9,10-trinorborn-5-ene-2,3-dicarboxylic anhydride, HET anhydride, Chloran 542, 1,4,5,6,7,7-hexachloro-8,9,10-trinorborn-5-ene-2,3-dicarboxylic anhydride, MFCD00080438, C9H2Cl6O3, (1S,7R)-1,7,8,9,10,10-hexachloro-4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione, Chloroendic anhydride, SCHEMBL29492244, AKOS037622046, NS00132702, Chlorendic anhydride, 95%, may cont. up to 3% chlorendic acid, 1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic anhydride, 97%, CHLORENDIC ANHYDRIDE, 115-27-5, HET anhydride, 1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic anhydride, Chloran 542, 4,5,6,7,8,8-Hexachloro-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione, Chlorendic anhydride (VAN), NSC 22229, DTXSID2026941, HSDB 2920, Hexachloro-5-norbornene-2,3-dicarboxylic anhydride, Hexachloroendomethylene tetrahydrophthalic anhydride, EINECS 204-077-3, 4,7-Methanoisobenzofuran-1,3-dione, 4,5,6,7,8,8-hexachloro-3a,4,7,7a-tetrahydro-, BRN 0092693, 5-Norbornene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-hexachloro-, DTXCID006941, EC 204-077-3, 4-17-00-06070 (Beilstein Handbook Reference), 1,4,5,6,7,7-Hexachlorobicyclo(2.2.1)-5-heptene-2,3-dicarboxylic acid anhydride, NSC-22229, 1,4,5,6,7,7-Hexachloro-endo-5-norbornene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-Hexachloro-8,9,10-trinorborn-5-ene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-Hexachloro-endo-bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]-5-heptene-2,3-dicarboxylic acid anhydride, Bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-hexachloro-, RefChem:575603, Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-hexachloro-, Hexachloro-endo-methylene tetrahydrophthalic anhydride, 1,4,5,6,7,7-hexachlorobicyclo-(2,2,1)-5-heptene-2,3-dicarboxylic anhydride, 4,5,6,7,8,8-hexachloro-3a,4,,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione, 204-077-3, 1,4,5,6,7,7-HEXACHLORO-5-BICYCLO(2.2.1)HEPTENE-2,3-DICARBOXYLIC ANHYDRIDE, 2,3-Dicarboxy-1,4,5,6,7,7-hexachlorobicyclo(2.2.1)hept-5-ene anhydride, 3,4,5,6,7,7-Hexachloro-1,2,3,6-tetrahydro-3,6-endo-methylenephthalic anhydride, 4,7-METHANOISOBENZOFURAN-1,3-DIONE, 4,5,6,7,8,8-HEXACHLORO-3A,4,7,7A-TETRAHYDRO-, (3AR,4S,7R,7AS)-REL-, 7365-74-4, Bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylic acid, 1,4,5,6,7,7-hexachloro-, anhydride, Chlorendic anhydride [HSDB], Chlorendic anhydride [MI], ENDO-1,4,5,6,7,7-HEXACHLORO-1,2,3,4-TETRAHYDRO-5-NORBORNENE-2,3-DICARBOXYLIC ACID ANHYDRIDE, Hexachloro endomethylene tetrahydrophthalic anhydride, V92ZON9773, 1,7,8,9,10,10-hexachloro-4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione, C9H2Cl6O3, 4,5,6,7,8,8-hexachloro-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione, 1,7,8,9,10,10-hexachloro-4-oxatricyclo[5.2.1.0<2,6>]dec-8-ene-3,5-dione, SCHEMBL108694, CHEMBL3183752, FLBJFXNAEMSXGL-UHFFFAOYSA-, NSC22229, Tox21_200439, SBB056758, STL573382, 1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride, AKOS008967309, 1,4,5,6,7,7-Hexachlorobicyclo [2.2.1]hept-5-ene-2,3-dicarboxylic anhydride, NCGC00248616-01, NCGC00257993-01, BS-42226, CAS-115-27-5, DB-060714, CS-0377987, H0349, NS00007305, ST50981589, F71249, F237166, 1,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic anhydride, 4,3-dione, 4,5,6,7,8,8-hexachloro-3a,4,7,7a-tetrahydro-, 1,7,8,9,10,10-hexachloro-4-oxatricyclo[5.2.1.0,dec-8-ene-3,5-dione, 1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic anhydride treated BSA, 1,7,8,9,10,10-hexachloro-4-oxatricyclo[5.2.1.0(2),]dec-8-ene-3,5-dione, InChI=1/C9H2Cl6O3/c10-3-4(11)8(13)2-1(5(16)18-6(2)17)7(3,12)9(8,14)15/h1-2H, 4,7-Methanoisobenzofuran-1,3-dione, 4,5,6,7,8,8-hexachloro-3a,4,7,7a-tetrahydro-, 5-Norbornene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-hexachloro-, Chloran 542, Hexachloro-5-norbornene-2,3-dicarboxylic anhydride, Hexachloroendomethylene tetrahydrophthalic anhydride, HET Anhydride, 1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-Hexachlorobicyclo [2.2.1]hept-5-ene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]-5-heptene-2,3-dicarboxylic acid anhydride, Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-hexachloro-, NSC 22229, 1,4,5,6,7,7-hexachloro-8,9,10-trinorborn-5-ene-2,3-dicarboxylic anhydride, chloran542, Chloran 542, HET ANHYDRIDE, HetAnhydride>CHLORENDIC ANHYDRIDE, Chloroendic anhydride, LABOTEST-BB LT00053116, Chlorendic anhydride 99%, Chlorocrotonic anhydride, Bridge anhydride chloride, 1,4,5,6,7,7-hexachloro-5-norbornene-2,3-dicarboxylic anhydride, hexachloroendomethylenetetrahydrophthalic anhydride, 4,7-methanoisobenzofuran-1,3-dione, 4,5,6,7,8,8-hexachloro-3a,4,7,7a-tetrahydro-, 5-norbornene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-hexachloro-, 4,5,6,7,8,8-Hexachloro-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione,1,4,5,6,7,7-Hexachloro-5-bicyclo[2.2.1]heptene-2,3-dicarboxylic Anhydride,1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic Anhydride,1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]-5-heptene-2,3-dicarboxylic Acid Anhydride,1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic Anhydride,2,3-Dicarboxy-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene Anhydride,3,4,5,6,7,7-Hexachloro-1,2,3,6-tetrahydro-3,6-endo-methylenephthalic Anhydride, Chlorendic acid, hexachloroentomethylenetetrahydrophthalic acid, HET acid, 4,5,6,7,8,8-Hexachloro-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione,1,4,5,6,7,7-Hexachloro-5-bicyclo[2.2.1]heptene-2,3-dicarboxylic Anhydride,1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic Anhydride,1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]-5-heptene-2,3-dicarboxylic Acid Anhydride,1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic Anhydride,2,3-Dicarboxy-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene Anhydride,3,4,5,6,7,7-Hexachloro-1,2,3,6-tetrahydro-3,6-endo-methylenephthalic Anhydride, Chloran 542, Chlorendic Anhydride, HET Anhydride, Hexachloro-5-norbornene-2,3-dicarboxylic Anhydride, Hexachloroendomethylene Tetrahydrophthalic Anhydride, Kayahard CLA, NSC 22229, endo-1,4,5,6,7,7-Hexachloro-1,2,3,4-tetrahydro-5-norbornene-2,3-dicarboxylic Acid Anhydride, 4,7-Methanoisobenzofuran-1,3-dione,4,5,6,7,8,8-hexachloro-3a,4,7,7a-tetrahydro-,5-Norbornene-2,3-dicarboxylic anhydride,1,4,5,6,7,7-hexachloro-,Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride,1,4,5,6,7,7-hexachloro-,4,5,6,7,8,8-Hexachloro-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione,Chlorendic anhydride,2,3-Dicarboxy-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene anhydride,HET Anhydride,1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]-5-heptene-2,3-dicarboxylic acid anhydride,1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride,endo-1,4,5,6,7,7-Hexachloro-1,2,3,4-tetrahydro-5-norbornene-2,3-dicarboxylic acid anhydride,3,4,5,6,7,7-Hexachloro-1,2,3,6-tetrahydro-3,6-endo-methylenephthalic anhydride,Hexachloroendomethylene tetrahydrophthalic anhydride,1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic anhydride,Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid,1,4,5,6,7,7-hexachloro-,anhydride,Hexachloro-5-norbornene-2,3-dicarboxylic anhydride,1,4,5,6,7,7-Hexachloro-5-bicyclo[2.2.1]heptene-2,3-dicarboxylic anhydride,Chloran 542,Kayahard CLA,NSC 22229,122485-51-2, PERCHLOROBICYCLO (2.2.1)-5-HEPTENE-2,3-DICARBOXYLIC ANHYDRIDE,PERCHLOROBICYCLO[2.2.1]HEPT-5-ENE-2,3-DICARBOXYLIC ANHYDRIDE,1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]-5-heptene-2,3-dicarboxylicacidanhydride,1,4,5,6,7,7-hexachloro-endo-5-norbornene-2,3-dicarboxylicanhydride,1,4,5,6,7,7-hexachloro-endo-bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylicanhydride,1,4,5,6,7,7-HEXACHLORO-5-NORBORNENE-2,3-DICARBOXYLIC ANHYDRIDE,4,7-Methanoisobenzofuran-1,3-dione, 4,5,6,7,8,8-hexachloro-3a,4,7,7a-tetrahydro-,4,7-Methanoisobenzofuran-1,3-dione,4,5,6,7,8,8-hexachloro-3a,4,7,7a-t
Chlorendic Anhydride is a solid, reactive flame retardant.
An acid anhydride with a chlorine content of 54.5%, Chlorendic anhydride imparts permanent flame retardance, high heat distortion, and excellent corrosion and abrasion resistance to resins such as unsaturated polyesters and alkyds.
Chlorendic anhydride is 1,4,5,6,7,7-hexachloro-8,9,10-trinorborn-5-ene-2,3-dicarboxylic anhydride.
Chlorendic anhydride has a stable chlorinated bicyclic structure and offers improved color.
Chlorendic anhydride imparts permanent flame retardance, high heat distortion and excellent corrosion-, chemical- & abrasion- resistance.
Chlorendic Anhydride is a solid, reactive flame retardant with an unusually stable chlorinated bicyclic structure.
Chlorendic Anhydride is a chlorinated hydrocarbon used in the synthesis of unsaturated polyester resins.
Chlorendic anhydride is also an environmental pollutant.
Chlorendic anhydride is a chlorinated Reactive flame retardant Intermediate
Chlorendic Anhydride is a solid, reactive acid anhydride flame retardent.
Chlorendic Anhydride is a highly chlorinated cyclic dicarboxylic acid anhydride belonging to the organochlorine compound family.
Chlorendic anhydride is the anhydride form of chlorendic acid and has historically been produced in large industrial volumes as a reactive intermediate for flame-retardant polymers, epoxy curing agents, polyester resins, and corrosion-resistant composite materials.
Unlike additive flame retardants that can migrate out of plastics, Chlorendic Anhydride becomes chemically bonded into polymer networks, making it a reactive flame-retardant intermediate with long-term stability in finished products
Chlorendic Anhydride is a white crystalline solid with a rigid bicyclic molecular structure containing six chlorine atoms and a cyclic acid anhydride functional group.
Chlorendic anhydride is insoluble in water.
The high chlorine content contributes significantly to its flame-retardant properties, while the anhydride group makes Chlorendic anhydride highly reactive toward alcohols, glycols, amines, and epoxy systems.
Chlorendic anhydride has extremely low vapor pressure, meaning that inhalation exposure under ordinary conditions is much less significant than exposure to airborne dust particles generated during industrial handling.
USES and APPLICATIONS of CHLORENDIC ANHYDRIDE:
Chlorendic anhydride is mainly used in the synthesis of polymers and in metal working.
Key applications of Chlorendic anhydride: Metal working, UV stabilizer, Corrosion resistance.
Chlorendic anhydride is used as a reactive flame retardant for unsaturated polyester, polyurethane and epoxy resins, and is used as epoxy curing agents.
The epoxy products resistance is good of the heat distortion temperature about 180 ℃.
Chlorendic anhydride is used in the synthesis of polymers, used in production of fiberglass-reinforced resins for chemical industry equipment.
Chlorendic anhydride can be used to make alkyd resins for use in special inks and paints.
Chlorendic anhydride is used as a hardening agent in epoxy resins used in manufacture of printed circuit boards
Chlorendic anhydride is used in preparation of polyester resins.
Chlorendic Anhydride is also used as a cross-linking agent in epoxy resins as a low-smoke component in polyols for rigid polyurethane foams and in UV curable inks and coatings for its adhesion to metal.
Resin systems containing Chlorendic Anhydride can be formulated to meet ASTM E84 (Underwriter’s Tunnel Test) UL-94 and ASTM E 162-78 (Surface Flammability Test) as well as to meet specifications for flame retardant, corrosion-resistant coatings.
Epoxy resin applications of Chlorendic anhydride: Epoxy resins from Chlorendic Anhydride can be used as laminates for electrical uses, potting and encapsulation, adhesives requiring flame resistance, and high-heat distortion and protective coatings where permanent flame retardance, heat resistance, corrosion resistance and abrasion resistance are required.
Chlorendic anhydride acts as a flame retardant.
Chlorendic anhydride provides good adhesion to plastics, flexibility and high gloss.
Chlorendic Anhydride is used in adhesives.
Chlorendic anhydride is used to impart permanent flame retardance, high heat distortion, and exceptional corrosion and abrasion resistance to resins such as unsaturated polyesters and alkyds.
Commonly applied in the production of composites for boats, construction panels, and electrical applications, Chlorendic anhydride is also utilized in epoxy resins, metal adhesive coatings, and UV curable inks and coatings, particularly for enhancing metal adhesion.
Additionally, Chlorendic Anhydride serves as a crosslinking agent in epoxy resins and a low-smoke component in polyols for rigid polyurethane foams.
Resin systems containing, Chlorendic anhydride can be formulated to meet flame retardancy and surface flammability standards such as ASTM E84, UL-94, ASTM E 162-78, and U.S. military specifications.
Chlorendic anhydride is used in the synthesis of polymers, used in production of fiberglass-reinforced resins for chemical industry equipment.
Chlorendic anhydride can be used to make alkyd resins for use in special inks and paints.
Chlorendic anhydride is used as a hardening agent in epoxy resins used in manufacture of printed circuit boards
Uses of Chlorendic anhydride: Epoxy Resins, Inks, Coatings, Crosslinker, Epoxy Resin Hardener, Flame Retardant, Marine Coatings, Paint & Coatings, Polyurethane Foam, Unsaturated Polyester Resins, UV Curable Inks
Chlorendic anhydride has been widely used in fiberglass-reinforced composites, printed circuit board materials, chemical storage equipment, specialty coatings, and industrial resins where both flame resistance and chemical durability are required.
Due to its high chlorine content, Chlorendic anhydride provides excellent flame-retardant performance, although its environmental persistence and potential health hazards have led to increased regulatory attention.
Chlorendic Anhydride has been used primarily as a reactive flame-retardant intermediate rather than as a simple additive.
Instead of merely mixing into plastics, Chlorendic anhydride chemically reacts during polymer production and becomes part of the finished polymer structure.
One of Chlorendic anhydride's largest applications has been the manufacture of unsaturated polyester resins used for fiberglass-reinforced composites.
These composites are widely used in chemical processing equipment, industrial tanks, pipes, ducts, and corrosion-resistant structures.
Chlorendic anhydride has also been extensively used as a curing agent for epoxy resins, particularly in applications requiring high chemical resistance and improved fire performance.
Printed circuit boards have historically used epoxy systems based on chlorendic chemistry.
Another important application of Chlorendic anhydride is the production of halogenated polyols through reactions with glycols.
These polyols are incorporated into polyurethane foams where improved flame resistance is required.
Chlorendic Anhydride has also been used in: Fiberglass-reinforced plastics, Corrosion-resistant laminates, Industrial coatings, Alkyd resins, Specialty paints, Printing inks, Reactive flame-retardant plasticizers, ABS polymer formulations (limited use), Chemical storage equipment, Industrial construction materials.
-Unsaturated polyester resin applications of Chlorendic anhydride:
Unsaturated polyesters resins made from Chlorendic Anhydride are used in flame-retardant, glass-reinforced polyester composites for boats, construction panels, electrical applications and machine housings.
In polyester corrosion-resistant applications, Chlorendic Anhydride is used in piping and in tanks and scrubbers for the chemical, fertilizer and pulp industries.
-Flame Retardant Applications of Chlorendic anhydride:
Chlorendic anhydride serves as a reactive flame retardant suitable for several polymer systems, including: Unsaturated polyester resins, Polyurethane formulations, and Epoxy resin systems.
The high chlorine content (approximately 61% by weight) contributes to its effectiveness as a flame retardant by releasing chlorine radicals during combustion, which interfere with the radical chain reactions that propagate flames.
-Curing Agent for Epoxy Resins uses of Chlorendic anhydride:
Chlorendic anhydride functions as a hardening agent in epoxy resin systems, particularly those used in the manufacture of printed circuit boards .
Its anhydride functionality allows Chlorendic anhydride to react with epoxide groups to form crosslinked networks with desirable thermal and electrical properties.
-Additional Industrial Applications of Chlorendic anhydride:
Beyond its primary uses, chlorendic anhydride finds application as: A dye intermediate in the chemical industry, an insecticide component, A flame retardant treatment for fabrics and textiles, and a component in the production of fiberglass-reinforced resins for chemical industry equipment.
-Alkyd coating applications of Chlorendic anhydride:
Alkyd coatings from Chlorendic Anhydride-based alkyds are used extensively for industrial and marine coatings applications.
They are used in approved coating formulas, meeting military specifications Mil-R-21417 for Navy ships and in industrial environments requiring chemical resistance combined with flame retardance.
-UV curable ink and coating applications of Chlorendic anhydride:
UV curable ink and coatings from Chlorendic Anhydride are used in polyester-based coatings and inks to provide good adhesion to metal, fast curing and hardness.
In heat-fusible polyester and alkyd inks, Chlorendic anhydride provides good adhesion to plastics, flexibility and high gloss.
BENEFITS AND ADVANTAGES of CHLORENDIC ANHYDRIDE:
Chlorendic anhydride became commercially valuable because it combines several desirable industrial properties.
Its greatest advantage is that Chlorendic anhydride functions as a reactive flame retardant.
Because Chlorendic anhydride becomes chemically bonded into polymers, it is generally less likely to migrate or leach out compared with many additive flame retardants.
Other important advantages include:
*Excellent flame-retardant performance
*High chlorine content for fire inhibition
*Outstanding chemical resistance
*Good thermal stability
*Strong compatibility with polyester systems
*Effective epoxy curing behavior
*Long-term durability
*Excellent corrosion resistance in composites
*Low volatility
*High processing stability
These characteristics made Chlorendic anhydride particularly valuable for industrial equipment exposed to aggressive chemicals.
INDUSTRIAL CHARACTERISTICS of CHLORENDIC ANHYDRIDE:
Industrial production of Chlorendic anhydride is based on a Diels-Alder reaction that produces the characteristic chlorinated bicyclic structure.
Commercial material often contains small amounts of chlorendic acid resulting from partial hydrolysis.
Chlorendic anhydride has historically been produced in relatively high industrial volumes because of demand from:
Construction materials
Transportation composites
Chemical industry equipment
Electrical materials
Specialty polymer manufacturing
European markets have historically used a large proportion of chlorendic chemistry for flame-resistant composites in construction and transportation sectors, while other markets have emphasized corrosion-resistant industrial plastics.
CHARACTERISTICS of CHLORENDIC ANHYDRIDE:
Chlorendic Anhydride is a white crystalline, highly chlorinated reactive anhydride that combines excellent thermal stability with strong chemical reactivity during polymer manufacture.
Chlorendic anhydride's six chlorine atoms provide outstanding flame-retardant performance, while its anhydride functionality allows permanent incorporation into polyester, epoxy, and polyurethane systems.
Chlorendic anhydride's greatest industrial strengths are flame resistance, corrosion resistance, low volatility, high thermal stability, and durable polymer integration.
CHEMICAL PROPERTIES of CHLORENDIC ANHYDRIDE:
Chlorendic Anhydride possesses a highly chlorinated bicyclic norbornene structure that provides exceptional chemical stability under normal storage conditions.
However, the cyclic anhydride functional group remains chemically reactive.
Chlorendic anhydride rapidly hydrolyzes in the presence of water, converting into chlorendic acid.
This hydrolysis occurs readily in aqueous environments and is one of the most important chemical characteristics of the substance.
Chlorendic anhydride reacts with alcohols to produce ester derivatives and reacts with glycols to form halogenated polyols that are widely used in polyurethane foam formulations.
Chlorendic anhydride ring readily opens during reactions with amines and epoxy resins, making the compound an effective reactive curing agent.
Unlike many chlorinated organic compounds, Chlorendic Anhydride is relatively resistant to hydrolytic dechlorination because the chlorine atoms are tightly bound within the rigid bicyclic framework.
At elevated temperatures or during pyrolysis, decomposition produces hydrogen chloride gas and various chlorinated decomposition products.
MOLECULAR STRUCTURE AND CHARACTERISTICS of CHLORENDIC ANHYDRIDE:
Chlorendic anhydride contains a rigid bridged bicyclic norbornene skeleton with six chlorine atoms attached to the carbon framework.
The cyclic anhydride ring provides two carbonyl groups that participate in polymer-forming reactions.
This combination of a chemically stable chlorinated skeleton and a reactive anhydride group gives Chlorendic anhydride an unusual balance between stability during storage and high reactivity during polymer manufacturing.
Important structural characteristics include:
Highly chlorinated bicyclic framework
Cyclic acid anhydride functionality
High halogen content
Reactive carbonyl groups
Rigid molecular geometry
Strong carbon-chlorine bonds
Excellent thermal stability
Covalent incorporation into polymer networks
THERMAL CHARACTERISTICS of CHLORENDIC ANHYDRIDE:
One of the reasons Chlorendic Anhydride became commercially important is its excellent thermal behavior.
Chlorendic anhydride remains stable during many industrial processing operations involving elevated temperatures.
Its high melting point allows Chlorendic anhydride to withstand resin-processing conditions without premature decomposition.
When incorporated into polymer systems, the chlorine atoms contribute to flame inhibition during combustion by interfering with free-radical chain reactions in flames.
Under severe heating or fire conditions, however, decomposition may produce:
Hydrogen chloride (HCl)
Chlorinated organic fragments
Carbon oxides
SOLUBILITY BEHAVIOR of CHLORENDIC ANHYDRIDE:
Chlorendic Anhydride has unusual solubility characteristics.
Chlorendic anhydride is practically insoluble in water.
Chlorendic anhydride dissolves much more readily in polar organic solvents including:
Acetone
Methanol
Ethanol
Chlorendic anhydride exhibits poor solubility in nonpolar solvents such as:
Benzene
Hexane
Carbon tetrachloride
These solubility properties of Chlorendic anhydride are important during resin formulation and industrial processing.
CHEMICAL IDENTITY AND STRUCTURE of CHLORENDIC ANHYDRIDE:
Chlorendic anhydride, identified by CAS number 115-27-5 and EINECS number 204-077-3, has the molecular formula C9H2Cl6O3 and a molecular weight of 370.83 g/mol .
Chlorendic anhydride is structurally defined as 1,4,5,6,7,7-hexachlorobicyclo[2.2.1]-hept-5-ene-2,3-dicarboxylic anhydride, representing the dehydrated form of chlorendic acid .
Chlorendic anhydride features a rigid norbornene framework with six chlorine substituents and an anhydride group spanning two adjacent carbon atoms.
This unique structure contributes to Chlorendic anhydride's chemical stability and reactivity profile.
In particular, the presence of the anhydride functional group makes Chlorendic anhydride reactive toward nucleophiles, especially those containing hydroxyl or amine groups, which is fundamental to its applications as a curing agent and reactive modifier .
RELATIONSHIP TO CHLORENDIC ACID:
Chlorendic anhydride is closely related to chlorendic acid (CAS: 115-28-6), as the anhydride readily hydrolyzes to form the acid when exposed to water .
This relationship is important in understanding the environmental fate and metabolic processing of the compound, as biological systems typically transform the anhydride into the acid form
PHYSICAL CHARACTERISTICS of CHLORENDIC ANHYDRIDE:
Chlorendic anhydride appears as white crystalline material with a density of 1.73 g/ml at 20°C .
Chlorendic anhydride has distinguishing thermal properties, forming an anhydride with a melting point of 230-235°C .
SOLUBILITY PROFILE of CHLORENDIC ANHYDRIDE:
The solubility characteristics of chlorendic anhydride are important for its processing and applications.
Chlorendic anhydride is:
Chlorendic anhydride is soluble in benzene, hexane, acetone, and carbon tetrachloride
Slightly soluble in water, where Chlorendic anhydride undergoes hydrolysis to form chlorendic acid
CHEMICAL REACTIVITY of CHLORENDIC ANHYDRIDE:
When exposed to water, chlorendic anhydride undergoes hydrolysis to form chlorendic acid .
This reaction is significant in both environmental and biological contexts.
When subjected to pyrolysis, the related compound chlorendic acid decomposes to hydrochloric acid and various chlorinated compounds, suggesting similar decomposition pathways for the anhydride form under high-temperature conditions .
NOTES of CHLORENDIC ANHYDRIDE:
Chlorendic anhydride is moisture Sensitive.
Keep Chlorendic anhydride container tightly closed.
Store Chlorendic anhydride in cool, dry conditions in well sealed containers.
PRODUCTION AND INDUSTRIAL SYNTHESIS of CHLORENDIC ANHYDRIDE:
Chlorendic anhydride is commercially produced through a Diels-Alder reaction between hexachlorocyclopentadiene and maleic anhydride in a solvent system .
This synthesis represents a classic example of cycloaddition chemistry applied to industrial-scale production.
The commercial production typically involves a closed system to manage the reactivity and toxicity of the reagents.
Technical-grade chlorendic anhydride typically contains 1-3% chlorendic acid as an impurity .
Other common impurities may include residual maleic anhydride (maximum 0.25%) and hexachlorocyclopentadiene (maximum 50 ppm) from the manufacturing process .
PURIFICATION METHODS of CHLORENDIC ANHYDRIDE:
Steam distil the anhydride or recrystallise Chlorendic anhydride from H2O to yield pure diacid.
The pure diacid yields the anhydride with Ac2O.
PHYSICAL and CHEMICAL PROPERTIES of CHLORENDIC ANHYDRIDE:
Chemical Name: Chlorendic Anhydride
IUPAC Name: 1,4,5,6,7,7-Hexachloro-8,9,10-trinorborn-5-ene-2,3-dicarboxylic anhydride
CAS Number: 115-27-5
EC Number: 204-077-3
Molecular Formula: C₉H₂Cl₆O₃
Molecular Weight: 370.83 g/mol
PubChem CID: 8265
Chemical Class: Organochlorine compound, Cyclic acid anhydride, Reactive flame-retardant intermediate
Appearance: White crystalline powder or crystals
Physical State: Solid
Flammability: Combustible solid under certain conditions
Water Sensitivity: Moisture sensitive; hydrolyzes to chlorendic acid
Physical State: Solid
Appearance: White crystalline powder or crystals
Color: White to almost white
Odor: Slight or practically odorless
Molecular Formula: C₉H₂Cl₆O₃
Molecular Weight: 370.83 g/mol
Melting Point: 230–239°C
Boiling Point: Approximately 486.6°C (estimated)
Density: Approximately 1.73 g/cm³
Vapor Density: Approximately 13 (air = 1)
Vapor Pressure: 0–0.003 Pa (20–25°C)
Refractive Index: Approximately 1.555
Water Solubility: Insoluble
Moisture Sensitivity: Moisture sensitive
Henry's Law Constant: Approximately 1.1 × 10² mol/(m³·Pa)
Log P: Approximately 2.2
CAS: 115-27-5
IUPAC Name: 1,7,8,9,10,10-hexachloro-4-oxatricyclo[5.2.1.0²,⁶]dec-8-ene-3,5-dione
Molecular Formula: C9H2Cl6O3
InChI Key: FLBJFXNAEMSXGL-UHFFFAOYNA-N
SMILES: ClC1=C(Cl)C2(Cl)C3C(C(=O)OC3=O)C1(Cl)C2(Cl)Cl
Molecular Weight (g/mol): 370.81
Synonym: chlorendic anhydride
Appearance (Color): White
Form: Powder and/or Lumps
Assay (Titration ex Anhydride): >94.0 to <106.0%
Molecular Weight: 370.8 g/mol
XLogP3-AA: 2.4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 0
Exact Mass: 369.810560 Da
Monoisotopic Mass: 367.813510 Da
Topological Polar Surface Area: 43.4 Ų
Heavy Atom Count: 18
Formal Charge: 0
Complexity: 498
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 2
Undefined Atom Stereocenter Count: 2
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
CBNumber: CB3264515
Molecular Formula: C9H2Cl6O3
Molecular Weight: 370.83
MDL Number: MFCD00080438
MOL File: 115-27-5.mol
Melting Point: 235-239 °C(lit.)
Boiling Point: 486.58°C (rough estimate)
Density: 1,73 g/cm3
Vapor Density: 13 (vs air)
Vapor Pressure: 0-0.003Pa at 20-24.85℃
Refractive Index: 1.5550 (estimate)
Form: powder to crystal
Color: White to Almost white
Water Solubility: insoluble
Sensitive: Moisture Sensitive
Merck: 14,2086
BRN: 92693
Henry's Law Constant: 1.1×102 mol/(m3Pa) at 25℃, Zhang et al. (2010)
InChI: 1S/C9H2Cl6O3/c10-3-4(11)8(13)2-1(5(16)18-6(2)17)7(3,12)9(8,14)15/h1-2H/t1,2,7-,8+
InChIKey: FLBJFXNAEMSXGL-UHFFFAOYSA-N
SMILES: ClC1=C(Cl)[C@@]2(Cl)C3C(C(=O)OC3=O)[C@]1(Cl)C2(Cl)Cl
LogP: -1.59-1.39 at 20-25℃
CAS Database Reference: 115-27-5(CAS Database Reference)
EWG's Food Scores: 1
FDA UNII: V92ZON9773
NIST Chemistry Reference: Chlorendic anhydride(115-27-5)
EPA Substance Registry System: Chlorendic anhydride (115-27-5)
UNSPSC Code: 12162002
NACRES: NA.23
Other (deleted CASRN): 122485-51-2
ECHA EINECS - REACH Pre-Reg: 204-077-3
FDA UNII: Search
Nikkaji Web: J5.265E
Beilstein Number: 0092693
MDL: MFCD00080438
XlogP3-AA: 2.40 (est)
Molecular Weight: 370.82454000
Formula: C9 H2 Cl6 O3
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in: water, 0.8637 mg/L @ 25 °C (est)
Product Name: Chlorendic anhydride
CAS No.: 115-27-5
Molecular Formula: C9H2Cl6O3
InChIKeys: InChIKey=FLBJFXNAEMSXGL-UHFFFAOYSA-N
Molecular Weight: 370.83
Exact Mass: 370.83
BRN: 92693
EC Number: 204-077-3
ICSC Number: 1373
NSC Number: 22229
DSSTox ID: DTXSID2026941
Color/Form: Fine white crystals
HScode: 29172090
Categories: Organic Reagents
Melting point :235-239 °C(lit.)
Boiling point :486.58°C (rough estimate)
Density :1,73 g/cm3
vapor density :13 (vs air)
vapor pressure :0-0.003Pa at 20-24.85℃
refractive index :1.5550 (estimate)
form :powder to crystal
color :White to Almost white
Water Solubility :insoluble
Sensitive :Moisture Sensitive
Merck :14,2086
BRN :92693
Henry's Law Constant :1.1×102 mol/(m3Pa) at 25℃, Zhang et al. (2010)
InChI :1S/C9H2Cl6O3/c10-3-4(11)8(13)2-1(5(16)18-6(2)17)7(3,12)9(8,14)15/h1-2H/t1,2,7-,8+
InChIKey :FLBJFXNAEMSXGL-UHFFFAOYSA-N
SMILES :ClC1=C(Cl)[C@@]2(Cl)C3C(C(=O)OC3=O)[C@]1(Cl)C2(Cl)Cl
LogP :-1.59-1.39 at 20-25℃
CAS DataBase Reference :115-27-5(CAS DataBase Reference)
NIST Chemistry Reference :Chlorendic anhydride(115-27-5)
EPA Substance Registry System :Chlorendic anhydride (115-27-5)
FIRST AID MEASURES of CHLORENDIC ANHYDRIDE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available
ACCIDENTAL RELEASE MEASURES of CHLORENDIC ANHYDRIDE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.
FIRE FIGHTING MEASURES of CHLORENDIC ANHYDRIDE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
EXPOSURE CONTROLS/PERSONAL PROTECTION of CHLORENDIC ANHYDRIDE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.
HANDLING and STORAGE of CHLORENDIC ANHYDRIDE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.
STABILITY and REACTIVITY of CHLORENDIC ANHYDRIDE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available
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