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

Flash point:

>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

Exposure limits

ACGIH: Ceiling 0.005 mg/m3

Stability:

Moisture Sensitive

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)

Safety Information

Hazard Codes 

Xn

Risk Statements 

41-42/43

Safety Statements 

23-24-26-37/39

RIDADR 

3335

WGK Germany 

1

TSCA 

Yes

HS Code 

29172090

Hazardous Substances Data

85-42-7(Hazardous Substances Data)

MSDS

• Language:English Provider:Cyclohexane-1,2-dicarboxylic anhydride
• Language:English Provider:ALFA

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.

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.

Definition

ChEBI: A cyclic dicarboxylic anhydride that is the cyclic anhydride of hexahydrophthalic acid.

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 (85-42-7)Related Product Information

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