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ChemicalBook--->CAS DataBase List--->85-42-7

85-42-7

85-42-7 Structure

85-42-7 Structure
IdentificationMore
[Name]

Hexahydrophthalic anhydride
[CAS]

85-42-7
[Synonyms]

1,2-CYCLOHEXANEDICARBOXYLIC ANHYDRIDE
cyclohexane-1,2-dicarboxylic anhydride
HEXAHYDROPHTHALIC ANHYDRIDE
HHPA
1,2-Cyclohexanedicarboxylic Acid anhydride
1,3-Isobenzofurandione, hexahydro-
3-Isobenzofurandione,hexahydro-1
Araldite HT 907
hexahydro-3-isobenzofurandione
Lekutherm Hardener H
NT 907
Hexahydrophthalic Anhydride (HHPA)
Hexahydro benzoicanhydride
1,2-CYCLOHEXANEDICARBOXYLIC ANHYDRIDE, 9 5%
1,2-cyclohexanedicarboxylic anhydride, mixed isomers
1,2-cyclohexanedicarboxylic anhydride, predominantly cis
Hexahydro-1,3-isobenzofurandione.
CYCLOHEXANEDICARBOXYLIC ANHYDRIDE: HHPA
HEXAHYDROPHTALICACIDANHYDRIDE
Hexahydrophthalsureanhydrid
[EINECS(EC#)]

201-604-9
[Molecular Formula]

C8H10O3
[MDL Number]

MFCD00064863
[Molecular Weight]

154.16
[MOL File]

85-42-7.mol
Chemical PropertiesBack Directory
[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
[Exposure limits]

ACGIH: Ceiling 0.005 mg/m3
[Stability:]

Moisture Sensitive
[Uses]

Intermediate for alkyds, plasticizers, insect repellents, and rust inhibitors; hardener in epoxy resins.
[CAS DataBase Reference]

85-42-7(CAS DataBase Reference)
[NIST Chemistry Reference]

1,2-Cyclohexane dicarboxylic anhydride(85-42-7)
[EPA Substance Registry System]

85-42-7(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R41:Risk of serious damage to eyes.
R42/43:May cause sensitization by inhalation and skin contact .
[Safety Statements ]

S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24:Avoid contact with skin .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
[RIDADR ]

3335
[WGK Germany ]

1
[TSCA ]

Yes
[HS Code ]

29172090
[Hazardous Substances Data]

85-42-7(Hazardous Substances Data)
Raw materials And Preparation ProductsBack Directory
[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
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Cyclohexane-1,2-dicarboxylic anhydride(85-42-7).msds
Hazard InformationBack Directory
[Hazard]

Toxic by inhalation, strong irritant to eyes and skin.
[Chemical Properties]

White crystalline powder
[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.
[Flammability and Explosibility]

Nonflammable
[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.
Synthesis_85-42-7
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.]
Questions And AnswerBack Directory
[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
Spectrum DetailBack Directory
[Spectrum Detail]

Hexahydrophthalic anhydride(85-42-7)1HNMR
Hexahydrophthalic anhydride(85-42-7)IR
Hexahydrophthalic anhydride(85-42-7)Raman
Hexahydrophthalic anhydride(85-42-7)FT-IR
Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

1,2-Cyclohexanedicarboxylic anhydride, cis + trans, 97%(85-42-7)
[Sigma Aldrich]

85-42-7(sigmaaldrich)
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