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| Product Name: | Hexahydrophthalic anhydride | | Synonyms: | 1,2-Cyclohexanedicarboxylic Acid anhydride;1,3-Isobenzofurandione, hexahydro-;3-Isobenzofurandione,hexahydro-1;Araldite HT 907;hexahydro-3-isobenzofurandione;Lekutherm Hardener H;NT 907;CALCIUM 2-NAPTHYLPHOSPHATE | | CAS: | 85-42-7 | | MF: | C8H10O3 | | MW: | 154.16 | | EINECS: | 201-604-9 | | Product Categories: | Organics;Diels-Alder Adducts | | Mol File: | 85-42-7.mol |  |
| | Hexahydrophthalic anhydride Chemical Properties |
| Melting point | 32-34 °C(lit.) | | Boiling point | 158 °C17 mm Hg(lit.) | | density | 1.18 | | vapor pressure | 0.31Pa at 25℃ | | refractive index | 1.4620 (estimate) | | RTECS | NP6895168 | | Fp | >230 °F | | storage temp. | Store below +30°C. | | solubility | Chloroform, Methanol (Slightly) | | form | Solid | | pka | 4.14[at 20 ℃] | | color | White to Off-White | | Water Solubility | 4.2g/L at 20℃ | | Sensitive | Moisture Sensitive | | BRN | 83213 | | Henry's Law Constant | 4.7×10-1 mol/(m3Pa) at 25℃, HSDB (2015) | | Exposure limits | ACGIH: Ceiling 0.005 mg/m3 | | Stability: | Moisture Sensitive | | InChI | 1S/C8H10O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h5-6H,1-4H2/t5-,6+ | | InChIKey | MUTGBJKUEZFXGO-OLQVQODUSA-N | | SMILES | O=C1OC(=O)[C@H]2CCCC[C@@H]12 | | LogP | -4.14 at 20℃ | | CAS DataBase Reference | 85-42-7(CAS DataBase Reference) | | NIST Chemistry Reference | 1,2-Cyclohexane dicarboxylic anhydride(85-42-7) | | EPA Substance Registry System | Hexahydrophthalic anhydride (85-42-7) |
| Hazard Codes | Xn | | Risk Statements | 41-42/43 | | Safety Statements | 23-24-26-37/39 | | RIDADR | 3335 | | WGK Germany | 1 | | Autoignition Temperature | 395°C (DIN 51794) | | TSCA | TSCA listed | | HS Code | 29172090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Dam. 1
Resp. Sens. 1
Skin Sens. 1 | | Hazardous Substances Data | 85-42-7(Hazardous Substances Data) |
| | Hexahydrophthalic anhydride Usage And Synthesis |
| Description | Hexahydrophthalic anhydride (HHPA) is widely used for electronics applications, e.g. HHPA cured epoxy resins have excellent dielectric properties, high-temperature stability, and high glass transition temperatures. HHPA is used as a curing agent in adhesive coatings and sealant materials, e.g. for the second-generation two-part epoxy adhesive synthesis. Hexahydrophthalic anhydride is also used in the manufacture of alkyd and polyester resins, insecticides, and rust preventives.
| | References | [1] Guy Rabilloud, High Performance Polymers. Vol. 1 Conductive Adhesives, 1997
[2] John Burke Sullivan and Gary R. Krieger, Clinical Environmental Health and Toxic Exposures, 2001
[3] B. A. G. Jönsson, H. Welinder, C. Hansson and B. Ståhlbom, Occupational exposure to hexahydrophthalic anhydride: air analysis, percutaneous absorption, and biological monitoring, International Archives of Occupational and Environmental Health 1993, vol. 65, 43-47
| | Chemical Properties | White crystalline powder | | Uses | Intermediate for alkyds, plasticizers, insect repellents, and rust inhibitors; hardener in epoxy resins. | | Uses | 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. | | 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.] |
| | Hexahydrophthalic anhydride Preparation Products And Raw materials |
| Raw materials | Tetrachlorophthalic anhydride-->2-Cyclohexene-1,2-dicarboxylic acid-->3,4,5,6-tetrahydrophthalic acid-->cis-Hexahydrophthalic acid-->3,4,5,6-Tetrahydrophthalic anhydride-->1,2,3,6-Tetrahydrophthalic anhydride | | Preparation Products | 1(3H)-Isobenzofuranone,hexahydro--->1,2-Bis(7-Methyloctyl)cyclohexyl-1,2-dicarboxylate |
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