|
HS Code |
503320 |
| Chemical Formula | C7H15NO |
| Molar Mass | 129.20 g/mol |
| Appearance | Colorless to pale yellow liquid |
| Odor | Characteristic odor |
| Density | 0.962 g/cm³ (at 20 °C) |
| Boiling Point | 224 - 226 °C |
| Solubility In Water | Soluble |
| Solubility In Organic Solvents | Soluble in common organic solvents like ethanol, methanol |
| Flash Point | 99 °C (closed cup) |
As an accredited 1-Pyrrolidinepropanol [Also: 1-(3-Hydroxypropyl)Pyrrolidine] factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100 - gram vial packaging for 1 - Pyrrolidinepropanol (1-(3 - Hydroxypropyl)Pyrrolidine). |
| Shipping | 1 - Pyrrolidinepropanol will be shipped in well - sealed, corrosion - resistant containers. Special care is taken to ensure compliance with chemical transportation regulations, with proper labeling for safe and secure transit. |
| Storage | 1 - Pyrrolidinepropanol (1-(3 - Hydroxypropyl)pyrrolidine) should be stored in a cool, dry place away from heat sources and open flames. Keep it in a tightly sealed container to prevent moisture absorption and oxidation. Store separately from incompatible substances, such as strong oxidizing agents, acids, and bases, to avoid potential chemical reactions. |
In flexible slabstock polyurethane manufacturing, incorporation of a pyrrolidine-bearing polyol directly into the polymer backbone addresses volatile organic compound (VOC) emission mandates without sacrificing catalysis. The molecule’s tertiary amine centre drives the water-isocyanate reaction during foam rise, while the primary hydroxyl group grafts onto the polymeric network through urethane bond formation. Typical use levels fall between 0.25 and 0.70 pphp (parts per hundred polyol), blended into the polyol phase prior to mixing with toluene diisocyanate (TDI) or methylene diphenyl diisocyanate (MDI). Pre-drying of the polyol stream to a moisture content below 0.05 % is mandatory; bulk storage at 30–35 °C under dry nitrogen prevents hygroscopic uptake. The compound exhibits a delayed cream time relative to conventional bis(2-dimethylaminoethyl) ether catalysts, a characteristic exploited to widen the processing window in high-resilience seating foams where early gelling causes flow defects. Hydroxyl number of the neat liquid approximates 430–440 mg KOH/g, amine value 430–435 mg KOH/g, and viscosity stays below 12 mPa·s at 25 °C. Emission compliance is verified against VDA 278: thermal desorption at 90 °C for 30 min yields total VOC typically ≤ 80 µg/g in the finished foam, while fogging condensate per DIN 75201-B remains under 1.0 mg. On multi-block production lines a metering accuracy of ± 0.02 pphp is critical because excess amine accelerates post-cure exotherm, risking core scorch in thick blocks. Density of the resultant foam ranges from 28 to 55 kg/m³ with air permeability 50–120 L/min according to ASTM D3574-17. Migration kinetics have been monitored by HPLC-UV in leachate studies; no free amine was detected after 72 hours of Soxhlet extraction with methanol, confirming full covalent anchoring. An operational boundary strictly excludes pre-mix exposure to atmospheric humidity beyond 60 % RH as the hydroxypropyl chain rapidly hydrates, promoting urea segregation at the polymer-polyol interface.What reaction pathways exploit the dual hydroxy-tertiary amine structure in API synthesis?The bifunctional scaffold enters pharmaceutical syntheses chiefly through ether linkage or alkylation leveraging the terminal hydroxyl, while the pyrrolidine nitrogen serves as a protonation site or a handle for further quaternization. One established route involves activation of 1-pyrrolidinepropanol with methanesulfonyl chloride at 0–5 °C in anhydrous dichloromethane, forming the mesylate intermediate that is immediately treated with a sodium phenolate of the target heterocycle. The coupling step proceeds at 35–40 °C over 8–12 hours under argon, yielding the ether-linked intermediate at conversions exceeding 88 % when monitored by in-process HPLC with a C18 column and UV detection at 254 nm. Residual palladium, if present from prior steps, must be limited to ≤ 10 ppm per ICH Q3D Elemental Impurity guidelines, which mandates an activated carbon Darco G-60 treatment before the final recrystallization from isopropanol-water (7:3 v/v). The free amine pKa of ~10.3 enables acid addition salt formation with HCl gas in ethyl acetate, delivering a crystalline hydrochloride melting at 138–141 °C. When the intermediate is destined for atypical antipsychotic precursors, enantiomeric purity of the final drug substance is assayed via chiral HPLC using Chiralpak IA column; the synthetic step involving the pyrrolidine propanol moiety is rarely a source of racemization owing to the absence of acidic α-hydrogens. Production-scale reactors compliant with ICH Q7 GMP operate with jacket temperature control at ± 1 °C during the exothermic mesylation step; batch records document holding times after quench do not exceed 30 minutes to prevent by-product N-oxide formation. Residual solvent limits (dichloromethane ≤ 600 ppm) are enforced per USP General Chapter <467>. A limitation arises with moisture-sensitive organometallic reagents: the hydroxyl group must be transiently protected with trimethylsilyl chloride if a Grignard coupling is planned, otherwise protonolysis reduces yield below 30 %.Quaternary Ammonium Conditioners Derived from N-(3-Hydroxypropyl)PyrrolidineQuaternization of 1-pyrrolidinepropanol with stearyl bromide or cetyl bromide in a pressurized reactor at 85–95 °C under 2.5–3.0 bar nitrogen produces a series of cationic surfactants whose hydrophilic-lipophilic balance (HLB) shifts with the alkyl chain length. The reaction mass is held at reflux in isopropanol for 18–24 hours; conversion is tracked by amine value titration until the number drops below 3 mg KOH/g. The resulting alkylpyrrolidinium propanol bromide crystallizes upon cooling and is purified by acetone trituration to achieve a quaternary content ≥ 97 % by potentiometric titration with sodium dodecyl sulfate. In prototype hair conditioning formulations, the ingredient replaces up to 50 wt% of the benchmark cetrimonium chloride without compromising wet combability. A composition of 2.0 wt% pyrrolidinium quat combined with 0.5 wt% cetearyl alcohol and 0.1 wt% guar hydroxypropyltrimonium chloride yields a lamellar gel network after homogenization at 15,000 min⁻¹ for 3 minutes. Reduction in combing force, measured on a Dia-Stron MTT175 at 25 °C and 65 % RH on bleached Asian hair tresses, averages 72–78 % relative to untreated tresses, meeting the internal criterion of > 70 %. The formulation remains stable for 12 months at 40 °C as per ASEAN Cosmetic Directive stability testing, provided pH is buffered to 4.0–4.8 with citric acid; alkaline drift triggers base-catalysed Hoffmann elimination, releasing volatile amine degradation products detectable by headspace GC-MS at ≥ 0.8 ppm. Toxicological screening per EC Regulation 1223/2009 Annex I must cover residual 1-bromoalkanes, capped at ≤ 10 ppm based on TTC Cramer Class III assessment. Used as a preservative booster, the quaternary structure retains bactericidal activity against Staphylococcus aureus ATCC 6538 with a log reduction of 3.2 at 500 ppm active in a suspension test method OECD TG 106.Corrosion Inhibition Mechanism in Hot HCl Pickling: An Electrochemical ViewThe pyrrolidine ring and pendant hydroxypropyl arm adsorb simultaneously onto low-carbon steel (SAE 1010) in 15 % hydrochloric acid at 60–70 °C, functioning as a mixed-type inhibitor. Electrochemical polarization scans executed with a three-electrode jacketed cell (Ag/AgCl reference, Pt counter, PAR VersaSTAT 3 potentiostat) at a sweep rate of 0.5 mV/s reveal a shift in corrosion potential Ecorr below 35 mV versus the uninhibited blank, qualifying the molecule as predominantly cathodic in character under these conditions. Optimum inhibition efficiency, calculated from potentiodynamic polarization Tafel slopes per ASTM G59-97, reaches 93 % at 0.12 wt% concentration with an immersion time of 6 hours. Weight loss coupons (ASTM G31-72, 50 mm × 25 mm × 2 mm, 600-grit finish) corroborate the electrochemical data, returning corrosion rates of ∼0.6 mm/year in the inhibited bath versus ∼8.7 mm/year for the uninhibited control. The protective film, characterized by X-ray photoelectron spectroscopy (XPS) C1s and N1s spectra, consists of chemisorbed ammonium species and a weak Fe ··· OH coordination complex; film thickness does not exceed 2–3 nm. Industrial pickling lines dosing the inhibitor via a positive displacement pump must maintain bath concentration within 0.08–0.15 wt%. A sharp decrease in inhibition performance occurs when bath temperature surpasses 85 °C, attributable to thermally induced desorption and partial hydrolysis of the hydroxypropyl group, quantified as an increase in iron content in the acid from 200 ppm to over 800 ppm within 4 hours. The chemical is incompatible with oxidizing corrosion inhibitors such as nitrites or inorganic peroxides, which oxidize the tertiary amine to the N-oxide, abolishing adsorption affinity. Foaming in vigorously agitated acid baths is managed by co-addition of 5–10 ppm of a silicone antifoam emulsion. Compliance with the EU Biocidal Products Regulation (BPR) for use in acid cleaners covering industrial descaling requires a pre-authorization dossier with volatilization half-life data (Henry’s law constant determined via OECD TG 111).Anhydride-cured epoxy systems formulated for electrical potting applications undergo acceleration when a hydroxy-functional tertiary amine is introduced at low stoichiometric ratios. Mixing 1-pyrrolidinepropanol into the anhydride component (methylhexahydrophthalic anhydride, MHHPA) at 1.5–3.0 phr in a heated planetary mixer at 40 °C reduces the peak exotherm temperature of the subsequent curing reaction by 12–18 °C and shortens the gel time at 100 °C from 45 to 18–22 minutes as registered by a GELNORM gel timer. The dual acceleration mechanism involves nucleophilic ring-opening of the anhydride by the free hydroxyl, generating a hemi-ester that converts the tertiary amine into a carboxylate-ammonium ion pair, itself catalytically active toward epoxy homopolymerisation. An interlock condition applies: if the equivalent weight ratio of the hydroxyl to the epoxy is allowed to exceed 0.08, the crosslink density measured via dynamic mechanical analysis (DMA) at 1 Hz and 3 °C/min ramp declines by more than 15 %, attributed to chain transfer and insertion of flexible oxypropylene segments. Formulators therefore pre-react the amine with a portion of the anhydride in a separate vessel at 90 °C for 60 minutes before combining with the epoxy resin (bisphenol A diglycidyl ether, epoxide equivalent weight 182–192 g/eq). Cured castings conditioned at 23 °C and 50 % RH for 24 hours exhibit tensile strength of 58–62 MPa by ISO 527-2:2012 type 1A specimens and glass transition temperature (Tg) by DSC at 127–133 °C. Dielectric breakdown strength tested per ASTM D149-20 on 2 mm sheets exceeds 18 kV/mm. Manufacturing batches must exclude any accidental contamination with primary amines or Lewis acids, which deactivate the accelerator by forming stable quaternary salts; this is monitored by FTIR tracking the anhydride carbonyl band at 1860 cm⁻¹. Published data on long-term thermal aging (UL 1557, 180 °C/500 h) for this specific promoter configuration is limited to internal company technical bulletins.Esterquat Precursor for Biodegradable Textile SoftenersEsterification of 1-pyrrolidinepropanol with stearic acid (1.05:1 molar excess of acid) catalyzed by 0.1 wt% stannous octoate at 180 °C under reduced pressure (50 mbar) furnishes a tertiary amino ester that becomes the backbone of an esterquat surfactant. The reaction water is removed through a Dean-Stark trap charged with xylene; endpoint is determined by acid value falling to ≤ 5 mg KOH/g. Subsequent quaternization with dimethyl sulfate in an anhydrous isopropanol medium at 60–65 °C produces the methyl sulfate salt. The crude esterquat is bleached with 1.5 % hydrogen peroxide (35 % active) at 70 °C to improve color to Gardner < 2. When dispersed at 5 wt% in an aqueous laundry softener base (pH 3.5), the compound deposits on cotton terry fabric during the rinse cycle at a dosage of 0.8 g/kg dry fabric, reducing the coefficient of friction measured by a fabric-feel analyzer (KES FB-4) by ∼38 % compared to untreated cloth. OECD 301B ready biodegradability testing returns a > 60 % ThCO2 evolution within 28 days at 20 °C, meeting the criteria for EU Ecolabel for laundry detergents (Decision (EU) 2017/1218). A processing bottleneck emerges when the esterification is scaled beyond 5-ton reactors: the molten ester product exhibits increased electrical conductivity due to trace ionic catalysts, which interferes with electrostatic discharge safety in subsequent flaking operations unless the product is passed through a microfilter of 0.5 µm absolute rating. Stability in commercial softener formulations extended to 12 weeks at 45 °C is achievable only if the headspace oxygen is displaced with nitrogen, otherwise pyrrolidine ring oxidation generates discoloration and a slight fishy odor noticeable by an odor panel at a threshold of 2 ppm volatile nitrogen species. Co-formulation with aldehydic fragrance components should be avoided, as Schiff base formation between the pyrrolidine nitrogen and aldehyde moieties progressively reduces perfume intensity (GC headspace analysis shows a ≥ 25 % drop after 4 weeks at ambient).An alternative reaction manifold exploits the nucleophilic displacement of benzyl chloride groups on a Merrifield resin, anchoring 1-pyrrolidinepropanol as a solid-supported phase-transfer catalyst for the O-alkylation of hindered phenols. The hydroxyl group is first tosylated at 0 °C in pyridine, then displaced with polymer-bound amine, yielding a quaternary ammonium site that facilitates the transport of phenolate anions from an aqueous KOH phase (25 wt%) into a toluene organic layer. Batch turnover exceeds 15 cycles before catalytic activity drops below 50 % of the initial rate, determined by monitoring the consumption of 1-bromodecane via GC at intervals. Regeneration of the resin with 1 M NaOH in methanol at 50 °C restores 85–90 % of the original activity. This immobilized form circumvents the acute aquatic toxicity concern associated with dissolved small-molecule ammonium chlorides (conventional phase-transfer agents exhibit EC50 values below 10 mg/L in Daphnia magna OECD 202 tests), placing the process within a lower emission band. The synthesis of pharmaceutical aroma ethers, notably 2-phenoxyethanol derivatives with pyrrolidine appendages, has been demonstrated on a 100 L fixed-bed column, though the space-time yield remains economically marginal unless the catalyst cost is amortized over 30+ production campaigns. Adherence to ATEX directives for handling combustible organic dust from the resin beads during loading is mandatory. |
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| Parameter | Technical Grade | Synthesis Grade | Test Method |
|---|---|---|---|
| Purity (GC area%) | ≥98.5 | ≥99.5 | IN-HOUSE GC-01 |
| Water content | ≤0.2% | ≤0.05% | ASTM E203 |
| Density at 20°C | 0.974–0.978 g/cm³ | 0.975–0.977 g/cm³ | ASTM D4052 |
| Refractive index n20/D | 1.471–1.474 | 1.4715–1.4730 | ASTM D1218 |
| APHA color (Hazen) | ≤50 | ≤20 | ASTM D1209 |
| Residue on ignition | ≤0.05% | ≤0.02% | ASTM D482 |
| Compound | pKa (conj. acid, 25°C) | Hydroxyl Reactivity | Typical Application |
|---|---|---|---|
| 1-Pyrrolidinepropanol | 9.8 | Primary –OH, bonds into PU | Low-VOC catalyst, pharma intermediate |
| 1-(2-Hydroxyethyl)pyrrolidine | 9.2 | Primary –OH, chelate-forming | Fugitive catalyst (higher emission) |
| N-Methylpyrrolidine | 10.1 | None | Strong blow catalyst, not REACH-compliant for some grades |
| 1-(3-Aminopropyl)pyrrolidine | ∼10.5 (primary amine) | –NH₂, not –OH | Epoxy curative, gel acceleration |