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Hexahydrophthalic anhydride

CAS No.
85-42-7
Chemical Name:
Hexahydrophthalic anhydride
Synonyms
HHPA;cyclohexane-1,2-dicarboxylic anhydride;1,2-CYCLOHEXANEDICARBOXYLIC ANHYDRIDE;Hexahydro-isobenzofuran-1,3-dione;1,3-Isobenzofurandione, hexahydro-;Hexahydrophthalic Anhydride (HHPA);NT 907;C6H10(CO)2O;Araldite HT 907;RRSYY(Selfotel)-1
CBNumber:
CB7468504
Molecular Formula:
C8H10O3
Molecular Weight:
154.16
MDL Number:
MFCD00064863
MOL File:
85-42-7.mol
MSDS File:
SDS
Last updated:2024-04-02 17:31:45

Hexahydrophthalic anhydride Properties

Melting point 32-34 °C(lit.)
Boiling point 158 °C17 mm Hg(lit.)
Density 1.18
vapor pressure 0.31Pa at 25℃
RTECS NP6895168
refractive index 1.4620 (estimate)
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)
EWG's Food Scores 2-3
FDA UNII B52Z7TNV87
NIST Chemistry Reference 1,2-Cyclohexane dicarboxylic anhydride(85-42-7)
EPA Substance Registry System Hexahydrophthalic anhydride (85-42-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS05,GHS08
Signal word  Danger
Hazard statements  H317-H318-H334
Precautionary statements  P261-P280-P280-P284-P304+P340-P305+P351+P338+P310
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
NFPA 704
1
2 0

Hexahydrophthalic anhydride price More Price(13)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 123463 1,2-Cyclohexanedicarboxylic anhydride, predominantly cis 95% 85-42-7 100g $47 2024-03-01 Buy
Sigma-Aldrich 123463 1,2-Cyclohexanedicarboxylic anhydride, predominantly cis 95% 85-42-7 500g $82.8 2024-03-01 Buy
Alfa Aesar L20001 1,2-Cyclohexanedicarboxylic anhydride, cis + trans, 97% 85-42-7 100g $33.8 2024-03-01 Buy
Alfa Aesar L20001 1,2-Cyclohexanedicarboxylic anhydride, cis + trans, 97% 85-42-7 500g $60.9 2024-03-01 Buy
TRC H294020 Hexahydro-1,3-isobenzofurandione 85-42-7 2.5g $135 2021-12-16 Buy
Product number Packaging Price Buy
123463 100g $47 Buy
123463 500g $82.8 Buy
L20001 100g $33.8 Buy
L20001 500g $60.9 Buy
H294020 2.5g $135 Buy

Hexahydrophthalic anhydride Chemical Properties,Uses,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

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.

Uses

Intermediate for alkyds, plasticizers, insect repellents, and rust inhibitors; hardener in epoxy resins.

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.
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.]

38765-78-5
85-42-7
Synthesis of Hexahydrophthalic anhydride from 2-Cyclohexene-1,2-dicarboxylic acid
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Hexahydrophthalic anhydride pictures 2024-04-26 Hexahydrophthalic anhydride
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US $0.00 / Kg/Drum 1KG 99% 1000mt Jinan Finer Chemical Co., Ltd
Hexahydrophthalic anhydride pictures 2024-04-02 Hexahydrophthalic anhydride
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Hexahydrophthalic Anhydride pictures 2023-11-09 Hexahydrophthalic Anhydride
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US $0.00-0.00 / kg 1kg ≥99.0% 71000tons Puyang Huicheng Electronic Materials Co., Ltd.
1,2-Cyclohexanedicarboxylic Acid anhydride 3-Isobenzofurandione,hexahydro-1 Araldite HT 907 hexahydro-3-isobenzofurandione Lekutherm Hardener H NT 907 CALCIUM 2-NAPTHYLPHOSPHATE 3a,4,5,6,7,7a-Hexahydro-2-benzofuran-1,3-dione 3a,4,5,6,7,7a-Hexahydro-1,3-isobenzofurandione 8-Oxabicyclo[4.3.0]nonane-7,9-dione 1,2-Cyclohexanedicarboxylic anhydride, cis and trans mixture,98% C6H10(CO)2O 3a,4,5,6,7,7a-hexahydroisobenzofuran-1,3-quinone Hexahydrophthalic an 1,2-Cyclohexanedicarboxylic anhydride, Mixture of cis and trans, trans≤2% Hexahydrophthalic anhydride, 99%, 99% 1,2-Cyclohexanedicarboxylic anhydride, cis and trans, 97% 1,2-Cyclohexanedicarboxylic anhydride, predoMinantly cis 95% HEXAHYDROPHTHALIC ANHYDRIDE 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 1,2-Cyclohexanedicarboxylic anhydride, cis + trans, 97% 1,2-Cyclohexanedicarboxylic anhydride, 99%, mixture of cis and trans, trans≤2% Methylhexahydrophthalic anhydride Manufacturer / In stock factory HEXAHYDROPHTHALIC ANHYDRIDE(AMH-330) 1,3-Isobenzofurandione, hexahydro- Hexahydro-isobenzofuran-1,3-dione 1,2-CYCLOHEXANEDICARBOXYLIC ANHYDRIDE HHPA cyclohexane-1,2-dicarboxylic anhydride Hexahydrophthalic Anhydride (HHPA) Hexaphthalic anhydride RRSYY(Selfotel)-1 85-42-7 ANHYDRIDE Organics Diels-Alder Adducts