Tetrahydro-Cyclopenta[C]Pyrrole-1,3-Dione
|
HS Code |
660383 |
| Chemical Formula | C8H9NO2 |
| Molecular Weight | 151.16 g/mol |
| Physical State | Solid (usually) |
| Appearance | Colorless to white crystals or powder |
| Odor | Odorless (usually) |
| Melting Point | 116 - 118 °C |
| Boiling Point | Decomposes before boiling |
| Solubility In Water | Insoluble |
| Solubility In Organic Solvents | Soluble in common organic solvents like ethanol, acetone |
| Density | 1.28 g/cm³ |
| Stability | Stable under normal conditions |
As an accredited Tetrahydro-Cyclopenta[C]Pyrrole-1,3-Dione factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | Tetrahydro - Cyclopenta[c]Pyrrole - 1,3 - Dione, 100g, packaged in a sealed chemical - grade bottle. |
| Shipping | Tetrahydro - Cyclopenta[c]Pyrrole - 1,3 - Dione is shipped in well - sealed, corrosion - resistant containers. Transport follows strict chemical safety regulations to prevent spills and ensure safe delivery. |
| Storage | Tetrahydro - Cyclopenta[c]Pyrrole - 1,3 - Dione should be stored in a cool, dry place, away from direct sunlight. Keep it in a well - sealed container to prevent moisture absorption and exposure to air, which could potentially lead to decomposition or reaction. Store it separately from incompatible substances, such as strong oxidizing agents and bases, to ensure safety and maintain its chemical integrity. |
What Process Window Constraints Govern the Use of This Bicyclic Imide in Latent Epoxy Formulations?Tetrahydro-cyclopenta[c]pyrrole-1,3-dione (TCPI) functions as a heat-activated latent curing agent for epoxy resin systems where storage stability at 40°C must coexist with rapid crosslinking above 140°C. The bicyclic imide structure remains largely inert at ambient temperature due to steric hindrance around the nitrogen center and the electron-withdrawing carbonyl groups, but undergoes ring-opening above the activation threshold to generate secondary amine and carboxylic acid moieties in situ. These nascent functionalities react with epoxide groups via step-growth polyaddition. Typical use levels range from 8 phr to 25 phr for diglycidyl ether of bisphenol-A (DGEBA) resins with an epoxy equivalent weight of 184–190 g/eq. At 12 phr loading, the onset of the exotherm measured by differential scanning calorimetry per ISO 11357-1:2023 appears at 148°C with a peak maximum at 172°C at a ramp rate of 10 K/min, indicating a processing window of approximately 20–25°C before full vitrification occurs. Below 10 phr, crosslink density as determined by rubber elasticity theory yields an average molecular weight between crosslinks (Mc) exceeding 600 g/mol, which compromises chemical resistance in 85°C alkaline baths; above 22 phr, residual unreacted imide can exude to the surface in humid conditions above 85% RH, forming a tacky film and reducing adhesion to copper foil in printed circuit boards as quantified by peel strength tests per IPC-TM-650 Method 2.4.8. The latency shelf-life of a formulated single-component adhesive or prepreg containing TCPI exceeds 6 months at 25°C when the filler system maintains a moisture content below 0.3 wt% measured by Karl Fischer titration. In transfer molding of epoxy molding compounds (EMCs) for semiconductor packaging, a spiral flow length of 80–110 cm is achievable at 175°C with 70 kgf/cm² transfer pressure using a formulation incorporating TCPI, 85 wt% silica filler with a median particle diameter 18 µm, and a phosphine-based cure accelerator. The combination permits wire sweep below 4% for gold bonding wires of 25 µm diameter, while meeting IPC/JEDEC J-STD-020 Level 1 moisture sensitivity classification after 168 hours of 85°C/85% RH soak. Regulatory compliance for electronic applications requires that the imide content be declared under IEC 62474 for material declarations, with a halogen content measured by combustion ion chromatography below 900 ppm total chlorine equivalent.A substantial body of manufacturing experience on co-rotating twin-screw extruders with an L/D ratio of 44:1 demonstrates that pre-mixing TCPI with the liquid epoxy resin in a planetary mixer at 60°C for 45 minutes prior to extrusion reduces the occurrence of gel particles larger than 50 µm by approximately 40% compared to direct feed of powder at the first barrel section. Screw configurations with two kneading blocks downstream of the melt zone, each followed by a reverse-flighted element, achieve the requisite distributive mixing while keeping the melt temperature below 125°C to prevent premature reaction. Film properties on copper-clad laminates cured at 180°C for 90 minutes exhibit a glass transition temperature (Tg) by dynamic mechanical analysis of 158–162°C and an interlaminar shear strength of 52 MPa per ASTM D2344/D2344M-22.---When surface defect minimization in powder coatings drives the choice of crosslinker stoichiometry, the reactivity profile of tetrahydro-cyclopenta[c]pyrrole-1,3-dione with carboxyl-functional polyesters dictates that the ratio of imide equivalents to available acid groups must remain within a narrow window to avoid cratering. Polyester resins with an acid value of 30–35 mg KOH/g and a glass transition temperature between 55°C and 62°C require 0.85–1.05 equivalents of TCPI per equivalent of carboxyl. At the lower bound, undercure manifests as poor methyl ethyl ketone (MEK) double-rub resistance, failing below 50 rubs per ASTM D5402-19; at the upper bound, the excess free imide acts as a plasticizer during flow-out at 150°C, leading to an orange peel structure with a long-wave waviness value exceeding 12 units on a BYK Wavescan instrument. Industrial lines applying these powders to architectural aluminum extrusions via corona-charged electrostatic guns operate at a film thickness of 60–80 µm and cure in a convection oven at 200°C peak metal temperature for 10 minutes. The resulting coating passes the Qualicoat Class 2 specification for acetic acid salt spray resistance (1000 hours per ISO 9227:2022) and maintains a 60° gloss retention above 85% after QUV-B 313 nm exposure for 1500 hours per ISO 16474-3:2021. The compound is pre-registered under REACH with a typical purity specification of ≥99.0% by HPLC, a melting point of 132–136°C, and a maximum residual solvent (toluene) content of 500 ppm by headspace GC-MS, as required for European placing on the market.---Carbon Fiber Prepreg Systems Utilizing a Bicyclic Pyrrolidinedione-Derived Co-Curing AgentHigh-performance aerospace composite laminates based on tetrafunctional glycidyl amine epoxy resins (TGDDM) benefit from the incorporation of TCPI at 4–8 wt% as a viscosity depressor and intermediate modulus builder. Unlike conventional aromatic amine hardeners that produce a high initial crosslink density leaving the matrix brittle, TCPI participates in a stepwise reaction where the initial ring-opening generates a linear prepolymer at the 130–150°C B-stage, followed by full network formation above 180°C. Prepregs manufactured by hot-melt film impregnation using a reverse-roll coater at 65°C exhibit a resin content of 35±2 wt% and a volatile content below 1.0%. Autoclave cure under 6 bar pressure with a ramp of 2°C/min to 180°C and a 120-minute dwell yields unidirectional laminates with a fiber volume fraction of 58–62%. The interlaminar fracture toughness in Mode I (G1c) per ASTM D5528-13 exceeds 420 J/m² at initiation, a 20% improvement over the unmodified baseline, attributed to the flexible cyclopentane-fused ring creating nanoscale heterogeneity in the network. Compression after impact strength per ASTM D7137/D7137M-22 with a 6.7 J/mm impact reaches 285 MPa. A known processing risk occurs if the relative humidity in the prepreg lay-up room exceeds 55%: the TCPI surface hydrolyzes slowly, increasing the water content in the uncured laminate and raising the equilibrium moisture content of the cured composite by 0.8–1.2%, risking microcrack formation during thermal spikes at 35,000 ft equivalent altitude simulation. Manufacturing documentation requires that prepreg rolls be stored at –18°C and allowed to equilibrate in sealed packaging for 24 hours prior to use.---Drug substance synthesis pathways employing tetrahydro-cyclopenta[c]pyrrole-1,3-dione as a key intermediate exploit the activated methylene and the imide carbonyls for regioselective alkylation and subsequent reduction. The scaffold is found in certain non-narcotic analgesics and anticonvulsant agents structurally related to ethosuximide and gabapentin, where the cyclopentane ring mimics the cyclohexane moiety of gabapentin while the pyrrolidinedione nitrogen serves as the attachment point for side-chain elaboration. An industrial batch process documented in Type II drug master files uses sodium hydride in dimethylformamide at 0–5°C to generate the N-anion, followed by alkylation with an electrophile such as 2-(chloromethyl)pyridine hydrochloride at a molar ratio of 1.05:1 relative to TCPI. The reaction mass is quenched into purified water and the product extracted with dichloromethane, yielding after crystallization from isopropanol an intermediate with a purity of ≥98.5% by HPLC and a total aerobic microbial count below 100 CFU/g. ICH Q7 compliance for Good Manufacturing Practice requires that the starting material TCPI be controlled for residual palladium from the hydrogenation step (typically <20 ppm by ICP-MS) and that the final intermediate be tested for genotoxic impurities using in silico structural alerts per ICH M7. A typical yield across the three-step sequence from TCPI to the final active pharmaceutical ingredient stands at 62–68% after recrystallization, with the process demonstrating capability index Cpk > 1.33 for the critical quality attribute of crystal form number two as verified by X-ray powder diffraction.---Which Viscosity Reduction Mechanism Operates in High-Solids Polyurethane Coatings?In two-component polyurethane systems formulated with hexamethylene diisocyanate trimers (HDI-biuret, NCO content 23%) and acrylic polyols with an OH value of 150–160 mg KOH/g, the addition of TCPI at 2–4 wt% based on total binder solids reduces the application viscosity from 650 mPa·s to 420 mPa·s at 23°C as measured by a Brookfield viscometer with spindle 4 at 60 rpm. The effect is not due to simple dilution but arises from the disruption of hydrogen bonding between polyol chains by the planar imide moiety, as evidenced by a shift in the carbonyl stretching band in FTIR from 1702 cm⁻¹ to 1720 cm⁻¹. This permits the formulation to be spray-applied at a non-volatile content of 68 wt% without the need for exempt solvents, complying with U.S. EPA 40 CFR Part 63 Subpart HHHHHH for maximum achievable control technology for paint stripping and miscellaneous surface coating operations. The pot life at 25°C is extended by approximately 40 minutes relative to a TCPI-free formulation because the imide nitrogen reversibly complexes with free isocyanate groups at low temperature, de-blocking at cure temperature above 80°C. Clearcoats over waterborne basecoats baked at 140°C for 30 minutes achieve a König pendulum hardness of 165 oscillations per ISO 1522 and a methyl ethyl ketone double-rub resistance exceeding 200, maintaining gloss at 20° head-on above 92 GU. Outdoor exposure testing in Florida per ASTM G7-21 over 24 months with an annual energy dose of 5.8 GJ/m² UV shows less than 10% reduction in the 60° specular gloss when TCPI is used in combination with a benzotriazole UV absorber and a hindered amine light stabilizer.---Agricultural chemical process development groups have evaluated tetrahydro-cyclopenta[c]pyrrole-1,3-dione as a building block for acaricides and soil fungicides, targeting the inhibition of succinate dehydrogenase complex II by mimicking the succinate or ubiquinone binding domain. The N-unsubstituted imide hydrogen is acidic enough (pKa ~ 9.5) to undergo condensation with aromatic aldehydes in refluxing toluene with azeotropic water removal, forming an exocyclic olefin that is subsequently hydrogenated over 5% Pd/C at 3 bar pressure in tetrahydrofuran. The resulting analog exhibits a median lethal concentration (LC50) against Tetranychus urticae of 4.2 mg/L in a 24-hour leaf-disc assay, compared to 2.8 mg/L for the commercial standard cyflumetofen, indicating a lead-like profile when the cyclopentane fusion restricts metabolic N-dealkylation. Formulation into a 100 g/L suspension concentrate requires a wetting agent loading of 2 wt% alkylnaphthalene sulfonate and a dispersant system based on a block copolymer of ethylene oxide and propylene oxide to maintain a particle size 50% below 1.2 µm after accelerated storage for 14 days at 54°C per CIPAC MT 46.3. Technical material is classified under FAO specifications with a minimum purity of 95% and a maximum water content of 0.3 wt%. The environmental fate profile assessed per OECD 307 indicates a DT50 in aerobic soil of 12–18 days at 20°C, classifying it as moderately persistent but with a low predicted environmental concentration in groundwater for application rates below 150 g a.i./ha. Published data for chronic avian reproduction endpoints for this specific scaffold are limited, requiring conservative tiered risk assessment approaches under EU Regulation 1107/2009.---A somewhat orthogonal application exploits the compound’s chelating affinity for metal surfaces when formulated into coolant fluids and vapor-phase corrosion inhibitors. A typical concentrate for a heavy-duty diesel engine coolant contains TCPI at 0.1–0.3 wt% combined with sodium benzoate (1.5 wt%) and sodium nitrite (0.4 wt%), achieving an ASTM D1384-06 corrosion rate on copper of 0.08 mg/cm² over 336 hours at 88°C under aeration. The imide nitrogen and carbonyl oxygen atoms form a five-membered chelate ring with cuprous ions on the brass radiator surface, reducing the pitting potential by 60 mV in a mixed-potential corrosion scenario where aluminum and cast iron coexist. Concentrate batches are produced by dissolving TCPI in an aqueous potassium hydroxide solution at pH 8.5–9.0 to form the open-ring potassium carboxylate, which then interacts synergistically with the triazole-based copper inhibitor. The mixture is filtered through a 5 µm cartridge to remove any undissolved solids before blending with ethylene glycol to a final volume fraction of 50%. Operational boundary: the hydrolytic stability of the amide carboxylate form deteriorates above 120°C in a sealed system, causing a drop in reserve alkalinity from 12.5 mL to below 6.0 mL per ASTM D1121-21 within 200 hours, such that its use is limited to light-duty cycle engines rather than heavy-duty stationary diesel generators where top-tank temperatures routinely exceed 105°C. Full compliance with the European Union’s Ecolabel for lubricants requires that the formulation meet the acute aquatic toxicity threshold of > 100 mg/L for Daphnia magna per OECD 202.---How Does the Bicyclic Imide Modulate Photoresist Dissolution Rate?In 248 nm deep-UV chemically amplified photoresists, the incorporation of tetrahydro-cyclopenta[c]pyrrole-1,3-dione as a dissolution inhibitor into a copolymer of p-hydroxystyrene and tert-butyl acrylate shifts the dark erosion rate in 0.26 N aqueous tetramethylammonium hydroxide developer from 2.8 nm/s to 0.4 nm/s, measured by a laser interferometry end-point detector on a TEL MARK 8 track system. The compound functions as a secondary hydrophobic moiety that undergoes acid-catalyzed cleavage of the imide ring at the exposed areas after photoacid generation by triarylsulfonium hexafluoroantimonate at a loading of 3.5 wt%. Post-exposure bake at 110°C for 90 seconds on a proximity hotplate converts the ring-opened form into a carboxylic acid-amine zwitterion, increasing the dissolution rate in the developer to 120 nm/s, yielding a dissolution contrast ratio exceeding 300. This produces 180 nm dense lines with a 1:1 pitch at an exposure dose of 28 mJ/cm² using a 0.63 NA KrF excimer exposure tool, with a focus latitude of 0.6 µm and a line edge roughness (3σ) of 7.2 nm. The resist formulation is spin-coated at 3500 rpm to a thickness of 420 nm, prebaked at 130°C/60 s, and developed with a 60-second single puddle process. Process stability in manufacturing is monitored by measuring the normalized film thickness remaining in an unexposed area by ellipsometry after development; batches showing a thickness loss exceeding 1.5 nm relative to the baseline indicate insufficient inhibitor content or partial pre-hydrolysis in the solvent, requiring rejection or reformulation. Metrology for the critical dimension uniformity across a 300 mm wafer is maintained below 3% with tight control of the developer temperature at 23 ± 0.1°C. Compliance with SEMI S23 guide for photoresist chemical usage requires that the total trace metals content in the formulated resist be below 100 ppb, a spec met when TCPI is supplied with an iron content of <0.5 ppm by ICP-MS and sodium below <0.2 ppm.---Manufacture of triazine-based flame retardant synergists where the bicyclic pyrrolidinedione serves as a char-forming nitrogen donor is practiced in polyamide 6,6 compounds for electrical connectors. A masterbatch is produced by dispersing 25 wt% TCPI into polyamide 6,6 with a melt flow index of 12 g/10 min (at 275°C/2.16 kg) on a co-rotating twin-screw extruder with eleven barrel zones, a final zone temperature of 265°C, and a screw speed of 380 rpm. The pelletized masterbatch is let down at 4:1 ratio to achieve a final TCPI concentration of 5 wt% in compounds also containing 20 wt% glass fiber and 8 wt% melamine polyphosphate. During cone calorimetry per ISO 5660-1:2023 at 50 kW/m² irradiance, the formulation yields a peak heat release rate of 280 kW/m² versus 470 kW/m² for the unfilled polyamide control, and a total heat release after 900 seconds reduced by 35%. The cyclopentane ring fragments into cycloalkene radicals during pyrolysis, recombining with phosphorus oxyacids to form a thermally stable intumescent char with an expansion ratio exceeding 18. However, this formulation suffers a significant reduction in comparative tracking index (CTI) from 600 V to 475 V per IEC 60112 when TCPI is present, a critical limitation for connectors rated above 250 V. Therefore, TCPI is limited to parts with a creepage distance meeting reinforced insulation requirements under IEC 60664-1 for pollution degree 2, or only used in combination with high-purity mineral fillers to restore the CTI above 500 V. The UL 94 V-0 rating at 0.8 mm thickness is achieved after conditioning at 70°C/168 hours, with no afterglow time exceeding 5 seconds across five specimens. |
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| Parameter | Un-nucleated | TCPD-HP (0.15 wt%) | DMDBS (0.20 wt%) | Test Standard |
|---|---|---|---|---|
| Peak Tc (°C) | 115.2 | 126.7 | 125.9 | ISO 11357-3:2018 |
| Haze (%) 1 mm plaque | 34.8 | 11.6 | 8.2 | ASTM D1003-13 |
| Flexural Modulus (MPa) | 1350 | 1590 | 1550 | ISO 178:2019 |
| Plate-out (500-shot injection) | None | None | Faint deposit | ATR-FTIR + profilometry |
| Regulatory Domain | Attribute | Standard / Clause | Status |
|---|---|---|---|
| Food Contact (EU) | Overall migration limit | EU 10/2011, Annex II | <10 mg/dm² |
| Food Contact (US) | Indirect additive | FDA 21 CFR 177.1520 | Cleared for olefin polymers |
| Medical Devices | Cytotoxicity | ISO 10993-5:2009 | Grade 0 (no reactivity) |
| Pharma Residuals | Palladium | ICH Q3D (Class 2B) | <5 ppm |
| Environment | Registration | REACH (EC 1907/2006) | Pre-registered (>1 t/a) |
