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Chemical Structure | Tetrahydrophthalic Anhydride (THPA) is a cyclic dicarboxylic anhydride with a chemical structure derived from tetrahydrophthalic acid. |
Physical Properties |
THPA appears as a white crystalline powder. It is insoluble in water and denser than water. This compound is very irritating to the skin and eyes. |
Definition |
ChEBI: 1,2,3,6-tetrahydrophthalic anhydride is a cyclic dicarboxylic anhydride that is 1,3,3a,4,7,7a-hexahydro-2-benzofuran carrying oxo groups at positions 1 and 3. It is a cyclic dicarboxylic anhydride and a tetrahydrofurandione. |
Applications | THPA is versatile and serves as an intermediate for various products. It is used in the production of polyesters, plasticizers, adhesives, and pesticides. Additionally, it functions as a hardener for resins. |
Toxicity and Corrosiveness | THPA is highly toxic and corrosive. It can cause irritation to the skin, eyes, and mucous membranes. It is also corrosive to both the skin and metals. |
Storage and Handling | THPA must be stored away from open flames or potential ignition sources. It is sensitive to moisture, and crystallization can occur in contact with humid air. |
Canonical SMILES | C1C=CCC2C1C(=O)OC2=O |
XLogP3-AA | 0.8 |
Complexity | 218 |
Precursors to Other Compounds |
THPA is a precursor to other compounds, including tetrahydrophthalic acid and tetrahydrophthalimide. Tetrahydrophthalimide is further used in the synthesis of the fungicide Captan. |
Hazard |
Strong irritant to eyes and skin. |
Health Hazard |
TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. |
Fire Hazard |
Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. |
Flammability and Explosibility |
Nonflammable |
Safety Profile |
Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. A corrosive irritant to skin, eyes, and mucous membranes. Combustible when exposed to heat or flame. Will react with water or steam to produce heat; can react with oxidizing materials. To fight fre, use water, foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ANHYDRIDES. |
InChI:InChI=1/C8H8O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1,3,5-6H,2,4H2
Electron Paramagnetic Resonance (EPR) analysis of gamma-irradiated tetrahydrophthalic anhydride (C8H8O3) single crystals was performed at 120 K. The single crystals were exposed to 60Co-gamma source at room temperature. The EPR spectra of gamma-irradiated single crystals of tetrahydrophthalic anhydride (THPA) were recorded at 10-degree intervals for different orientations of crystals in a magnetic field.
Herein, we focus on improving these properties. A (maleic anhydride/cis-1,2,3,6-tetrahydrophthalic anhydride) (MA/THPA) oligomer containing several cyclocarboxylic anhydride groups, which can copolymerize with PO, has been readily synthesized and used as the third comonomer to prepare PPC with cross-linked networks.
o-xylene
dimethyl cyclohex-4-ene-1,2-dicarboxylate
3,4-dimethoxycarbonylcyclohexyl-3′,4′-dimethylbenzene
1,2,3,6-Tetrahydrophthalic anhydride
Conditions | Yield |
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With Tridecane; In methanol; at 180 ℃; for 2h; Reagent/catalyst; Concentration; Inert atmosphere;
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92.2% |
maleic anhydride
buta-1,3-diene
1,2,3,6-Tetrahydrophthalic anhydride
Conditions | Yield |
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at 80 - 110 ℃; for 4h; Temperature; Large scale;
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98.1% |
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80% |
With benzene; at 100 ℃;
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With benzene; at 115 - 145 ℃;
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With benzene; at 20 ℃;
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In 1,4-dioxane; at 30 ℃; Yield given;
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In 1,4-dioxane; at 30 ℃; Rate constant; Kinetics;
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In neat (no solvent); at 30 ℃; for 2h; Green chemistry;
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95.6 %Chromat. |
maleic anhydride
2,3-dimethylbutene
buta-1,3-diene
3-Sulfolene
trimethylsilyl cis-2-isocyanato-4-cyclohex-1-ene carboxylate
5,10-Dihydro-4-ethyl-2-phenylpyrazolo<1,5-a><1,3>-7-cyclohexendiazepin-5,10-dione
(Z)-10-Nitro-8-phenyl-1,4,4a,6,13,14a-hexahydro-6,7,13-triaza-dibenzo[a,f]cyclodecene-5,14-dione
C34H36O12
CAS:120-74-1
Molecular Formula:C<sub>8</sub>H<sub>10</sub>O<sub>2</sub>
Molecular Weight:138.16
CAS:13716-12-6
Molecular Formula:C<sub>12</sub>H<sub>27</sub>P
Molecular Weight:202.32