Hexahydrophthalic anhydride

Base Information

• Chemical Name: Hexahydrophthalic anhydride
• CAS No.: 85-42-7
• Deprecated CAS: 102483-85-2,117276-22-9,95327-28-9,109265-67-0,109265-67-0,117276-22-9,95327-28-9
• Molecular Formula: C8H10O3
• Molecular Weight: 154.166
• Hs Code.: H10O3 MOL WT. 154.17
• European Community (EC) Number: 201-604-9,238-009-9,679-655-5
• ICSC Number: 1643
• NSC Number: 8622
• DSSTox Substance ID: DTXSID8026515
• Nikkaji Number: J70.181E
• Wikidata: Q26840977
• ChEMBL ID: CHEMBL273968
• Mol file: 85-42-7.mol

Synonyms:araldite;araldite CY 175 of araldite;araldite CY 179 of araldite;araldite CY 223;araldite D of araldite;araldite HT 907 of araldite;hexahydrophthalic anhydride

Chemical Property of Hexahydrophthalic anhydride

Chemical Property:

• Appearance/Colour: Colorless and clear viscous liquid
• Vapor Pressure: 0.003mmHg at 25°C
• Melting Point: 32-34 °C(lit.)
• Refractive Index: 1.502
• Boiling Point: 283.351 °C at 760 mmHg
• PKA: 4.14[at 20 ℃]
• Flash Point: 143.909 °C
• PSA: 43.37000
• Density: 1.236 g/cm³
• LogP: 0.87620
• Storage Temp.: Store at room temperature.
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform, Methanol (Slightly)
• Water Solubility.: 4.2g/L at 20℃
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 154.062994177
• Heavy Atom Count: 11
• Complexity: 187

Purity/Quality:

Hexahydro-1,3-isobenzofurandione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 41-42/43
• Safety Statements: 23-24-26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Plastics & Rubber -> Acid Anhydrides, Cyclic
• Canonical SMILES: C1CCC2C(C1)C(=O)OC2=O
• Effects of Short Term Exposure: The substance is irritating to the skin. The substance is severely irritating to the eyes.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. Repeated or prolonged inhalation may cause asthma.
• 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.
• Uses: Intermediate for alkyds, plasticizers, insect repellents, and rust inhibitors; hardener in epoxy 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.

Technology Process of Hexahydrophthalic anhydride

There total 19 articles about Hexahydrophthalic anhydride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid (46022-05-3) → trans-1,2-cyclohexanedicarboxylic anhydride (85-42-7,13149-00-3,14166-21-3,31982-85-1,71749-03-6,97233-90-4)

Guidance literature:

With acetyl chloride;

DOI:10.1002/1099-0690(200209)2002:17<2948::AID-EJOC2948>3.0.CO;2-E

Reference yield: 88.0%

3,4,5,6-Tetrahydrophthalic anhydride (2426-02-0) → 1,2-Cyclohexanedicarboxylic acid-anhydride (85-42-7)

Guidance literature:

With hydrogen; nickel; In N,N-dimethyl-formamide; at 95 ℃; for 3h; under 33752.7 Torr; Further Variations:; Catalysts; Pressures; Temperatures; Solvents; Product distribution;

Reference yield: 85.0%

(1S,2S)-cyclohexane-1,2-dicarboxylic acid (610-10-6,1687-30-5,2305-32-0,21963-41-7,46022-05-3,610-09-3) → trans-1,2-cyclohexanedicarboxylic anhydride (85-42-7,13149-00-3,14166-21-3,31982-85-1,71749-03-6,97233-90-4)

Guidance literature:

In acetic anhydride; toluene;

upstream raw materials:

3,4,5,6-Tetrahydrophthalic anhydride

(1R,2S)-cyclohexane-1,2-dicarboxylic acid

cyclohexane-1,2-dicarboxylic acid

phthalic anhydride

Downstream raw materials:

2-(2-diethylamino-ethyl)-(3ar,7ac)-hexahydro-isoindole-1,3-dione

cis-2-allylhexahydroisoindole-1,3-dione

9,10-phenanthrenequinone

(1S,2R)-2-Diisobutylcarbamoyl-cyclohexanecarboxylic acid

Refernces

• 1、 -. "RECYCLABLE POLYMERS BASED ON RING-FUSED GAMMA-BUTYROLACTONES". Page/Page column 34; 39. . Retrieved 2020/02/23.
• 2、 Rovira, Xavier,Harrak, Youssef,Trapero, Ana,Gonzlez-Bulnes, Patricia,Malhaire, Fanny,Pin, Jean-Philippe,Goudet, Cyril,Giraldo, Jesffls,Llebaria, Amadeu. "Exploring the active conformation of cyclohexane carboxylate positive allosteric modulators of the type 4 metabotropic glutamate receptor". . p. 2685 - 2698. Retrieved 2015/02/02.