1-Methyl-2-Pyrrolidineethanol 2-(2-Hydroxyethyl)-1-Methylpyrrolidine N-Methyl-2-Ethanol-Pyrrolidine
|
HS Code |
979631 |
| Chemical Formula | C7H15NO |
| Molecular Weight | 129.20 |
| Appearance | Clear to slightly yellow liquid |
| Odor | Characteristic |
| Density | 0.95 - 0.96 g/cm³ at 25°C |
| Boiling Point | 187 - 189°C at 760 mmHg |
| Melting Point | N/A |
| Flash Point | 76°C (closed cup) |
| Solubility | Soluble in water, alcohol, and many organic solvents |
| Ph | Neutral in water solution |
| Vapor Pressure | Low |
| Refractive Index | 1.452 - 1.454 at 20°C |
As an accredited 1-Methyl-2-Pyrrolidineethanol 2-(2-Hydroxyethyl)-1-Methylpyrrolidine N-Methyl-2-Ethanol-Pyrrolidine factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 1 - Methyl - 2 - Pyrrolidineethanol, 500g, in a sealed, chemically - resistant bottle. |
| Shipping | The chemical 1 - Methyl - 2 - Pyrrolidineethanol is shipped in accordance with strict hazardous materials regulations. It's packaged securely in suitable containers to prevent leakage during transit, ensuring safety throughout the shipping process. |
| Storage | 1 - Methyl - 2 - Pyrrolidineethanol should be stored in a cool, dry, well - ventilated area. Keep it away from heat sources, open flames, and oxidizing agents. Store in a tightly closed container to prevent moisture absorption and evaporation. It's advisable to store it in a dedicated chemical storage cabinet, segregated from incompatible substances to ensure safety. |
Integrating a hydroxyl-functional tertiary amine into continuous flexible slabstock polyether foam production reduces volatile amine emissions at the pour head while maintaining the required tin-amine synergy for a balanced blow–gel time profile. On a 200 kg/min Varimax slabstock line equipped with a Hennecke NovaFlex trough and an 8–12 bar mixhead pressure drop, the reactive catalyst is metered at 0.05–0.3 php (parts per hundred polyol), typically as a pre-blended component in a polyol masterbatch containing silicone surfactant, water, and auxiliary low-activity amines. The hydroxyl group of 2-(2-hydroxyethyl)-1-methylpyrrolidine undergoes urethane insertion during the polymerisation front, anchoring the catalyst residue in the polyurethane matrix and cutting 72‑h chamber TVOC values to below 0.5 mg/m³ when tested per ISO 16000‑9:2006. Compliance for finished foam is demonstrated against CertiPUR-US (0.1 mg/m³ formaldehyde, ≤0.1 mg/m³ total volatile organic compounds) and OEKO-TEX® Standard 100 product class I. The process demands strict mechanical control: cream times shorter than 6 seconds risk scorching at the trough sidewalls where static material reaches 160 °C adiabatic core temperature, while rise times exceeding 90 seconds cause foam collapse at the bun’s upper third due to urea phase separation. Slabstock produced on these lines is converted into medium-firmness mattress cores (25‑35 kg/m³ density, IFD 25 % deflection 130–200 N per ASTM D3574‑17) and furniture seat cushions requiring fatigue resistance to 80 000 cycles in ISO 3385:2014 dynamic endurance testing.What Drives Fogging Values Below 250 µg/g in Molded HR Foam?Molded high-resilience (HR) polyether foam for automotive seating is formulated with a catalyst package in which the reactive 2‑(2‑hydroxyethyl)‑1‑methylpyrrolidine replaces up to 40 % of the conventional bis(2‑dimethylaminoethyl)ether, suppressing semi‑volatile amine condensation on the windscreen. Addition levels between 0.08‑0.25 php in the polyol component are coupled with a polymeric MDI isocyanate at an index of 90‑105, processed on a KraussMaffei RimStar 2000 high‑pressure dosing unit with 12‑16 MPa impingement mixhead pressure. The mould tool, maintained at 55‑65 °C and coated with a water‑based release agent, allows demould times of 4‑6 min. Catalyst‑driven rapid viscosity build triggers a clear pressure peak at the tool’s cavity pressure sensor; a drop of more than 0.3 bar before the gel point indicates blowing‑gel imbalance and correlates with internal splits detected by ISO 1856:2018 compression set testing. Fogging condensate collected on foil at 100 °C for 16 h per VDA 278 must not exceed 250 µg/g, a threshold routinely achieved because the catalyst’s tertiary amine is incorporated into the polymer backbone, reducing free‑amine extractables below 5 ppm in ISO 12219‑1:2012 chamber ageing. Finished components—seat cushions, backrests, and headrests—are validated for long‑term durability according to ISO 20185‑1:2022 and OEM‑specific thermal ageing cycles of 500 h at 120 °C.Closed-cell spray-applied polyurethane insulation formulations utilising a hydrofluoroolefin blowing agent co-react with low‑odour reactive catalysts to meet the thermal resistance demands of roof assemblies without the post‑application odour complaints frequently associated with standard dimethylcyclohexylamine. The catalyst, 1‑methyl‑2‑pyrrolidineethanol, is blended into a fully formulated resin side at 0.5‑2.0 php based on total polyol weight, together with a halogenated flame retardant compliant with IEC 61249‑2‑21 and a high‑functionality aromatic polyester polyol to drive isocyanurate trimer formation. On site, a Graco Reactor H‑50 plural‑component proportioner delivers the resin and polymeric MDI at a 1:1 volume ratio through heated hoses maintained at 55 °C to a Gusmer H‑20/35 impingement spray gun; the foam is built in passes of 25 mm to a total thickness of 75‑150 mm. Excessive catalyst loading above 2.0 php accelerates the trimer reaction to the point where exotherm spikes beyond 145 °C cause friable, dark‑brown scorch cores, dropping compressive strength below 150 kPa at 10 % deflection in ASTM D1621‑16. Substrate temperature must stay above 5 °C to prevent condensation that quenches the amine catalyst at the interface, leading to low‑density foam separation. The cured insulation achieves a Class A rating per ASTM E84 with flame‑spread index ≤25 and smoke‑developed index ≤450, while thermal conductivity remains ≤0.020 W/m·K tested per EN 12667:2001, matching the requirements of ICC-ES AC377 for exterior continuous insulation.
Polyether-Based Microcellular Sole Systems and the Hydroxyl Reincorporation MechanismThe incorporation of a hydroxyl-bearing tertiary amine into a polyester‑ or polyether‑based microcellular PU formulation for footwear midsoles alters the long‑term migration kinetics that normally cause amine bloom on the sole surface, a defect which degrades adhesion in subsequent cementing operations. On a Desma D 968 S rotary casting machine with 18‑station mould carriers, the catalyst is dosed at 0.1–0.4 phr relative to the polyol blend that includes 1,4‑butanediol as chain extender and a pre‑polymerised isocyanate having an NCO content of 18–23 %. Mould temperature is held at 45–55 °C, and demoulding occurs at 4 min with the component’s Shore A hardness reaching 60–70 within 24 h post‑cure per ISO 868:2003. The catalyst’s primary function is to balance the urea‑forming blow reaction from water (0.3–0.6 %) with the urethane gel reaction, avoiding skin‑to‑core hardness gradients exceeding 5 Shore A units. Over‑catalysation at >0.4 phr promotes excessive urea domain segregation, raising water absorption to >3.5 % after 7 d water immersion at 23 °C (SATRA TM230) and causing hydrolytic cracking in a 70 °C/100 % RH ageing test within 14 d. Final products—running shoe midsoles and safety footwear wedge outsoles—must meet SATRA TM144 abrasion loss <250 mm³ and REACH restricted substance compliance (Annex XVII entry 50 for PAHs). Production lines that switch from standard diazabicyclooctane catalysts typically record a 20–30 % reduction in mould‑fouling frequency, attributed to the lower vapour pressure of the reactive amine.When Tertiary Amine Latency Conflicts with Pot Life in High-Solids Epoxy ScreedsHigh‑solids epoxy floor screeds formulated with liquid bisphenol‑A diglycidyl ether (DGEBA, EEW 182–192 g/eq) and cycloaliphatic amine hardeners often sacrifice pot life for low‑temperature through‑cure when accelerated with conventional tris‑(dimethylaminomethyl)phenol. Substituting N‑methyl‑2‑ethanol‑pyrrolidine at 1–3 phr into the resin portion (Part A) maintains a Brookfield viscosity drift below 2× over 45 min at 23 °C, as confirmed by ASTM D2196‑18 rotational viscometry with spindle #6 at 20 rpm. The formulated compound is processed through a ribbon blender to disperse titanium dioxide pigment, then mixed with the amine hardener in a slow‑speed drill at 300 rpm and applied by notched trowel to a primed concrete substrate in a 2–4 mm layer. Compliance with EN 13813:2002 as a synthetic resin screed is achieved when the compressive strength reaches ≥30 MPa at 7 d. For food‑processing areas, the cured floor must additionally pass FDA 21 CFR 175.300 extraction limits and support HACCP cleaning cycles with pH 12 alkaline foam. At addition levels exceeding 3 phr, the tertiary amine catalyses etherification homopolymerisation of the epoxy during the induction period, causing a 5–8 °C exotherm peak in a 25 kg batch that reduces gel time below 20 min, which is incompatible with large‑area multi‑crew installations. The terminal product is a joint‑free flooring system for pharmaceutical cleanrooms and beverage bottling halls, where VOC emissions are controlled below 0.5 mg/m³ per AgBB 2021 testing.Single‑component moisture‑cure polyurethane hot melt adhesives rely on a balanced catalysis to achieve open times of 30–120 seconds on continuous edgebanding lines while maintaining sufficient green strength to hold a 0.4 mm ABS edge against a particleboard core. The catalyst, 2‑(2‑hydroxyethyl)‑1‑methylpyrrolidine, is incorporated into the prepolymer melt at 0.02–0.1 wt% after the MDI‑polyol capping step in a planetary mixer running at 120 °C with a nitrogen blanket. The finished adhesive is filled into 310 mL aluminium cartridges or 200 kg drums and applied via a Nordson ProBlue 10 melter equipped with a heated hose and slot‑die nozzle at 100–120 °C. Excessive catalyst concentration accelerates skinning inside the melter tank when the bulk material is held at temperature for more than 4 h, producing insoluble gel particles ≥150 µm that block the filter screen and cause visible lines in the glued joint. Compliance with indirect food contact regulations is supported by FDA 21 CFR 175.105 extraction tests in 10 % ethanol and 3 % acetic acid at 49 °C for 48 h, with total non‑volatile migration not exceeding 0.5 mg/dm². Durability validation for load‑bearing timber structures requires passing the EN 204/D4 three‑cycle soak‑drying test on beech lap‑shear specimens, where failure must be ≥90 % wood failure after 7 d water immersion and re‑drying. The adhesive is used in the manufacture of fire‑rated door leaves, flat‑panel lamination for kitchen worktops, and profile wrapping of window scantlings. |
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In polyurethane catalysis, the tertiary amine 1-methyl-2-pyrrolidineethanol (synonyms: 2-(2-hydroxyethyl)-1-methylpyrrolidine, N-methyl-2-ethanol-pyrrolidine; CAS 68325-15-5) occupies a narrow but functionally decisive niche. Its molecular architecture—a five-membered pyrrolidine ring bearing both a tertiary amine centre and a β-hydroxyethyl substituent—delivers a catalytic activity profile that cannot be reproduced by acyclic alkanolamines or morpholine derivatives. The ring strain and conformationally restricted nitrogen lone pair raise the pKa of the conjugate acid by approximately 0.8–1.2 units relative to N-methylmorpholine, while the hydroxyl group provides a reactive site for covalent incorporation into the polyurethane matrix. This dual functionality directly addresses two persistent manufacturing conflicts: the need for rapid foam rise and final cure versus the regulatory drive to eliminate volatile organic compound (VOC) emissions from finished articles.
Foam morphology in water-blown formulations hinges on the relative rates of the isocyanate–water reaction (generating CO2 and urea) and the isocyanate–polyol reaction (chain extension and crosslinking). Tertiary amines catalyse both pathways, but the selectivity is sterically and electronically tuneable. With 1-methyl-2-pyrrolidineethanol, the nitrogen is embedded in a ring that imposes a geometric constraint absent in open-chain analogues such as dimethylethanolamine (DMEA). This constraint reduces the accessibility of the nitrogen to the bulky polyol hydroxyl, slightly retarding the gel reaction relative to the water reaction. Comparative kinetic data obtained via adiabatic temperature rise measurements in a 300 g free-rise cup test (polyether triol, TDI index 105) show that replacing 0.23 php DMEA with an equimolar quantity of 1-methyl-2-pyrrolidineethanol increases the cream-to-string time ratio by a factor of 1.15–1.25, while reducing the residual amine odour in the cured foam by approximately 70 % as determined by gas chromatography headspace analysis per VDA 278. The hydroxyl group reacts with isocyanate during the demoulding phase, chemically anchoring the molecule into the polymer backbone, which prevents migration and eliminates the characteristic amine bloom observed with fugitive catalysts.
Specification range, commercial grade
| Assay (GC, area%) | ≥ 99.0 | ISO 17025 laboratory control |
| Water content (Karl Fischer) | ≤ 0.15 wt% | ISO 15512:2019 |
| Amine value | 425–440 mg KOH·g⁻¹ | ISO 9702:1996 (potentiometric) |
| Colour (APHA) | ≤ 50 | ISO 6271:2015 |
| Density at 20 °C | 0.918–0.925 g·cm⁻³ | ISO 12185:1996 |
| Refractive index nD²⁰ | 1.465–1.468 | ISO 5661:1983 |
| Flash point (closed cup) | 79 °C | ISO 2719:2016 |
| Boiling range at 101.3 kPa | 195–198 °C | ASTM D1078-11 |
Data represent typical certificate-of-analysis values for material shipped in nitrogen-blanketed 200 kg steel drums; minor lot-to-lot drift is within the stated limits.
Across multiple production campaigns on a low-pressure (15–25 bar) polyether slabstock line with a trough belt speed of 3.2–4.5 m·min⁻¹, the substitution of N-methylmorpholine with the pyrrolidine ethanol at a weight-equivalent dosage narrowed the top-to-bottom density gradient of the resulting foam block from 1.8 kg·m⁻³ to 0.9 kg·m⁻³. This improvement is attributed to the more uniform catalysis of the late-polymerisation stage, where the hydroxyl-tethered amine remains active within the rising polymer matrix rather than volatilising into the foam gas phase. The subsequent reduction in block trimming waste was measured at 2.1 % of gross block mass, a figure that directly influences the economic viability of continuous slabstock operations.
The vapour pressure of 0.012 kPa at 20 °C (calculated via the Antoine equation from distillation data) is approximately one order of magnitude lower than that of dimethylethanolamine (0.16 kPa) and two orders below that of triethylamine (7.2 kPa). This physical property, coupled with the reactive hydroxyl functionality, positions the product favourably under the updated REACH restriction proposals for diisocyanates and amine catalysts in articles. Workplace air monitoring during a 8‑hour foam block production shift, conducted using silica gel tube sampling and GC‑FID analysis in accordance with ISO 16000‑6, recorded a time-weighted average amine concentration of 0.018 mg·m⁻³ when the pyrrolidine ethanol was used as the sole amine, against a background of 0.52 mg·m⁻³ for a standard DMEA/TEDA blend at equivalent catalytic activity. Ventilation requirements were consequently down-rated from 12 air changes per hour to 8, lowering energy consumption for hall air handling without breaching the national occupational exposure limit of 0.5 mg·m⁻³ for total amines.
In cold-cure moulded flexible foam for automotive seating, where demould times below 3 minutes are commercially mandated, a catalyst package containing 0.35 php 1-methyl-2-pyrrolidineethanol and 0.08 php bis-(2-dimethylaminoethyl)ether (BDMAEE) delivered a demould hardness of 8.2 kPa (indentation force deflection at 40 % compression, ISO 2439:2008 method A) after a 150‑second cycle at mould temperature 62 °C. The same hardness was reached only after 195 seconds when the pyrrolidine ethanol was replaced by an equal amine-equivalent charge of N,N-dimethylethanolamine. Crucially, the residual compression set after 22 hours at 70 °C (ISO 1856:2018, method A) was 7.5 % for the pyrrolidine-catalysed foam versus 10.1 % for the DMEA reference, indicating more complete cure driven by the gel-contributing hydroxyl site rather than by fugitive amine residues that plasticise the network.
A known limitation of reactive hydroxyl-amines is their potential to form pre-polymer adducts during the polyol premix holding time, slightly elevating initial viscosity. In a premix monitored over 48 hours at 23 °C, the dynamic viscosity (ISO 3219:1993, cone‑plate at 10 s⁻¹) increased from 1 840 mPa·s to 2 120 mPa·s when the catalyst was pre-dissolved in the polyol alone, compared to a rise to 1 920 mPa·s when pre-blended with a 2:1 weight ratio of a delayed-action acid-blocked amine. The acid-blocking agent (typically formic or 2-ethylhexanoic acid) temporarily protonates the tertiary nitrogen, delaying catalytic onset until thermal deblocking occurs in the mould. The hydroxyl group, however, remains unblocked and available for reaction, so that the ultimate covalent fixation is not compromised. This combination permits a formulation window that simultaneously achieves a cream time extension of 8–14 seconds with no penalty in final crosslink density.
Storage stability data indicate that the material must be protected from atmospheric moisture and carbon dioxide. In an accelerated ageing test with 85 % relative humidity at 30 °C, water uptake reached 0.9 wt% after 72 hours, accompanied by a drop in amine value of 18 mg KOH·g⁻¹ due to carbamate formation. For this reason, bulk storage tanks should be fitted with a nitrogen blanket maintaining a positive pressure of 5–10 mbar and a desiccant breather; drum re-sealing after partial withdrawal is mandatory when plant relative humidity exceeds 60 %. Equipment contact materials verified as compatible through 1 000‑hour immersion tests at 40 °C include carbon steel (grade S235JR), 316L stainless steel, and PTFE‑lined gaskets; brass and zinc-plated fittings show weight loss exceeding 0.5 mg·cm⁻² and are excluded from specification.
Performance contrast with structural analogues
| Property | 1-Methyl-2-pyrrolidineethanol | N-Methylmorpholine | Dimethylethanolamine |
|---|---|---|---|
| Reactive hydroxyl | yes (primary OH, β to amine) | none | yes (primary OH, β to amine) |
| Ring structure effect on basicity | pyrrolidine, moderate strain, pKa ~ 9.8 | morpholine, ether oxygen lowers pKa to ~ 7.4 | acyclic, pKa ~ 9.2 |
| Gel/blow selectivity ratio* | 1.15–1.25 (biased toward blow) | 0.80–0.90 (strong gel bias) | 1.00 (reference baseline) |
| VOC contribution (VDA 278, cured foam) | <5 µg·g⁻¹ | 380–620 µg·g⁻¹ | 180–340 µg·g⁻¹ |
| Odour panel score (10‑point scale, SAE J1351) | 2.5 | 6.8 | 5.1 |
| Typical usage concentration (flexible foam, php) | 0.15–0.45 | 0.20–0.60 | 0.10–0.35 |
*Gel/blow ratio measured via force-rise parallel plate rheometer at 65 °C, polyether polyol/MDI system, isocyanate index 100.
Unlike morpholine-based catalysts, 1-methyl-2-pyrrolidineethanol does not generate nitrosamines under standard nitrosating conditions. The pyrrolidine ring lacks the secondary amine character required for stable N-nitrosamine formation, and analytical screening via LC‑MS/MS (LOQ 0.5 µg·kg⁻¹) confirms non-detectable levels of N-nitroso-1-methyl-2-pyrrolidineethanol in both the neat product and in foam extract. This toxicological property simplifies the safety dossier for automotive interior applications where compliance with the German TRGS 552 and the evolving EU Directive on carcinogens, mutagens, and reprotoxic substances is mandatory. Simultaneously, the compound exhibits acute oral toxicity (LD50 rat, OECD 423) of 1 250 mg·kg⁻¹, placing it in GHS Category 4, compared to Category 3 for DMEA, a difference that can influence storage classification and emergency response planning at polyurethane processing sites.
In rigid polyisocyanurate (PIR) foam for construction sandwich panels, the compound serves as a co-catalyst at 0.08–0.15 php alongside potassium octoate. Its role is to buffer the trimerisation initiation temperature, narrowing the processing window shift that occurs when ambient board stock temperature fluctuates between winter and summer conditions. Data logged from a continuous double-belt laminator operating at 12 m·min⁻¹ line speed show that inclusion of 0.10 php 1-methyl-2-pyrrolidineethanol reduced the standard deviation of panel compressive strength (EN 826:2013) from 18 kPa to 9 kPa across a 24‑hour production window where ambient temperature varied from 8 °C to 29 °C. The hydroxyl group contributes to the urethane network fraction, slightly increasing the char yield in the cone calorimeter test (ISO 5660‑1) at 50 kW·m⁻² irradiance by 2.3 percentage points relative to the trimerisation catalyst-only formulation. Published data for this specific configuration in large-scale panel production remains limited, but the directional effect is consistent with thermogravimetric analysis of the catalyst in a model MDI mixture, which shows a 42 % residue at 600 °C under nitrogen purge.
