Hexahydrophthalic anhydride Property

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

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)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H317May cause an allergic skin reaction

H318Causes serious eye damage

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

Hexahydrophthalic anhydride Chemical Properties,Usage,Production

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.]