| HS Code | 473910 |
| Product Name | N-Octyl Cyanoacetate |
| Cas Number | 15666-97-4 |
| Iupac Name | Octyl 2-cyanoacetate |
| Synonyms | n-Octyl cyanoacetate; Octyl cyanoacetate; Cyanoacetic acid octyl ester |
| Molecular Formula | C11H19NO2 |
| Molecular Weight | 197.27 g/mol |
| Appearance | Clear colorless to pale yellow liquid |
| Purity | ≥98% |
| Density | 0.936 g/cm³ at 25 °C |
| Boiling Point | 155-156 °C at 15 mmHg |
| Refractive Index | 1.443 (n20/D) |
| Flash Point | >110 °C |
| Solubility | Insoluble in water; soluble in common organic solvents |
| Storage Conditions | Store in a cool, dry, well-ventilated area away from ignition sources |
| Hazard Classification | Irritant |
| Chemical Class | Cyanoacetate ester |
| Functional Groups | Ester, nitrile |
As an accredited N-Octyl Cyanoacetate factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | Supplied in 25 kg UN-approved high-density polyethylene drums with inner liners, securely sealed and labeled for chemical transport and handling. |
| Container Loading (20′ FCL) | N-Octyl Cyanoacetate is loaded into a 20′ FCL container in sealed drums, palletized, labeled, and secured for ocean freight. |
| Shipping | N-Octyl Cyanoacetate is typically shipped as a non-regulated liquid in tightly sealed, UN-approved containers. Keep upright and transport in a cool, dry, well-ventilated area away from heat, sparks, oxidizers, acids, and bases. Label with product name and CAS 15666-97-4; follow the SDS and applicable transport regulations. |
| Storage | N-Octyl cyanoacetate should be stored in a cool, dry, well-ventilated area away from heat, sparks, open flames, and direct sunlight. Keep containers tightly closed, labeled, upright, and protected from moisture. Store in a secure, locked cabinet. Segregate from strong oxidizers, acids, and bases. Use secondary containment and follow the manufacturer’s SDS for specific limits. |
| Shelf Life | Typically two years if kept sealed, cool, dry, and protected from light and moisture; avoid heat, acids, bases, and oxidizers. |
The conversion of n-octyl cyanoacetate to 2-octyl cyanoacrylate for medical topical tissue adhesive devices proceeds through a two-stage batch sequence: base-catalysed Knoevenagel condensation with paraformaldehyde at a stoichiometric ratio of 1.02–1.10 mol formaldehyde equivalent per 1.00 mol n-octyl cyanoacetate, followed by thermal depolymerisation of the washed and dried oligomer. The condensation is conducted in a glass-lined reactor with an external reflux condenser and a calibrated Dean-Stark trap; toluene or cyclohexane is charged as the azeotropic water-removal solvent, the reaction mass is heated to 80–110°C, and piperidine at 0.003–0.01 mol per mol ester is metered into the batch to initiate the condensation. Agitation is maintained at a tip speed of 1.5–3.0 m/s to keep the paraformaldehyde slurry suspended, and the water of reaction is removed until the overhead condensate remains clear; the resulting oligomeric poly(2-octyl cyanoacrylate) is acidified with methanesulfonic acid to quench the catalyst, washed with deionised water until the aqueous phase is neutral, and dried to ≤0.05 wt% water under vacuum at 80–100°C. The dried oligomer is blended with 1–5 wt% phosphorus pentoxide and 200–800 ppm hydroquinone, then fed to a wiped-film evaporator or short-path distillation unit operated at 0.5–2.0 kPa absolute and jacket temperatures of 150–190°C; the monomer vapour is condensed into a receiver pre-charged with an additional 50–200 ppm hydroquinone and 5–20 ppm sulfur dioxide. Quality gates typically require gas chromatographic purity of ≥98.5 area%, residual n-octyl cyanoacetate ≤0.5 wt%, residual formaldehyde ≤0.1 wt%, water ≤0.05 wt%, and colour below 50 APHA. For medical topical adhesive applications, polymerised product and monomer starting material are assessed under ISO 10993-5:2009 for cytotoxicity, ISO 10993-10:2010 for irritation and sensitisation, and mechanical performance is measured according to ASTM F2255-05(2015); packaging is specified to maintain a moisture-impermeable barrier, and terminal products are supplied as single-use applicator ampoules of 0.3–1.0 mL for topical wound closure after minor surgical incisions and lacerations. The principal operational boundary is anionic polymerisation: all transfer lines, receivers, and filter housings must be passivated with acidic solutions and dried, because residual alkaline detergent films reduce monomer shelf life to ≤72 h at 25°C. Published data for specific yield optimisation at full production scale for this exact ester is limited; the ranges cited represent industrial practice for homologous alkyl cyanoacetate depolymerisation units rather than a single universal recipe.
| Parameter | Limit | Method / Standard |
|---|---|---|
| 2-Octyl cyanoacrylate purity | ≥98.5 area% | GC-FID with internal standard |
| Residual n-octyl cyanoacetate | ≤0.5 wt% | GC-MS external standard |
| Residual formaldehyde | ≤0.1 wt% | HPLC post-column derivatisation |
| Water | ≤0.05 wt% | Karl Fischer titration |
| Hydroquinone | 50–200 ppm | HPLC-UV |
In low-surface-energy assembly operations, the monomer recovered from the depolymerisation train is compounded rather than used neat. A representative industrial formulation contains 90–99 wt% 2-octyl cyanoacrylate, 2–8 wt% poly(methyl methacrylate) thickener, 1–4 wt% hydrophobic fumed silica for thixotropic recovery, 0–5 wt% acetyl tributyl citrate as a non-reactive flexibiliser, 500–1,000 ppm hydroquinone, and 10–50 ppm sulfur dioxide; the silica is pre-dried at 120–150°C for 4–6 h before incorporation to avoid premature moisture-driven anionic polymerisation. Mixing is carried out in a planetary mixer under dry nitrogen with a dew point of ≤−40°C, and the batch is vacuum-deaerated at ≤20 mbar absolute until entrapped air is removed; the compounded adhesive is then passed through a 10 μm absolute filter into polyethylene bottles. The addition ratio of thickener is adjusted to reach a Brookfield viscosity of 50–250 mPa·s at 25°C using spindle 3 at 30 rpm, because the longer C8 ester chain reduces interchain hydrogen bonding relative to ethyl or methyl cyanoacrylates and requires higher thickener loading to achieve equivalent body. Lap shear strength is measured according to ISO 4587:2003 or ASTM D1002-10(2019) on acid-treated ABS and grit-blasted aluminium; typical bonded assemblies exhibit handling strength in 15–60 s at 23°C and 50% RH. Terminal product types include low-blooming flexible cyanoacrylate adhesives for EPDM gasket attachment, automotive interior trim, plasticised PVC edge banding, and cable jacket strain relief. The main operational incompatibility is with alkaline substrates and high-humidity packaging: exposure to ≥60% RH during filling reduces shelf life below 12 months, and contact with amine-containing primers accelerates cure before bond assembly. Published data for this specific compounded configuration is limited; the ranges above are representative starting points and must be verified by lap shear and accelerated ageing tests on the target substrate.
When n-octyl cyanoacetate is used as a lipophilic active methylene substrate, the C8 ester chain is retained through condensation and cyclocondensation steps, producing heterocyclic intermediates with enhanced solubility in low-polarity process solvents. A representative condensation route charges 1.00 mol aromatic aldehyde, 1.05–1.20 mol n-octyl cyanoacetate, and 0.02–0.05 mol piperidinium acetate in toluene, heating at 85–110°C with azeotropic removal of water through a Dean-Stark trap until gas chromatographic monitoring shows ≤1.0 area% residual aldehyde. The reaction mass is cooled to 20–30°C, washed with 5 wt% citric acid solution and then with water, dried over anhydrous magnesium sulfate, and concentrated; the resulting α-cyanoacrylate intermediate is then treated with hydrazine hydrate at 0.95–1.05 mol in ethanol at 60–78°C to form a 5-amino-1H-pyrazole-4-carboxylate scaffold, which is isolated by crystallisation from n-heptane/toluene at −5 to 5°C. This sequence enables the octyl chain to remain covalently attached, increasing log P and modulating the melting point of the heterocyclic intermediate relative to methyl or ethyl homologues. Compliance for isolated intermediates under REACH is managed through Article 17/18 strictly controlled conditions when the material is not placed on the market as a formulated product; for pharmaceutical intermediate shipments, residual solvent levels are assessed against ICH Q3C, with toluene controlled to ≤890 ppm as the Class 2 limit. If the downstream target is an agrochemical active substance, data packages are aligned with EU Regulation 1107/2009 for active substance purity and impurity profiling. Terminal product types are lipophilic heterocyclic building blocks for pharmaceutical screening libraries and crop protection candidate synthesis. The main operational boundary is hydrolytic sensitivity: the ester is prone to saponification under strong aqueous alkali at elevated temperature, so acidic or neutral workup is preferred, and glass-lined reactors are specified to avoid iron-catalysed colour formation. Published data for specific commercial active ingredients derived from the n-octyl ester is limited; the process conditions above follow general cyanoacetate Knoevenagel and cyclocondensation practice and must be optimised for each electrophile.
Veterinary wound closure devices converted from 2-octyl cyanoacrylate monomer occupy a separate manufacturing envelope from human medical adhesives, because the terminal product is not subject to the same sterility assurance level but must remain compliant with core biocompatibility endpoints. The adhesive is compounded from 100 parts monomer with 80–200 ppm hydroquinone, 5–20 ppm sulfur dioxide, and 0–50 ppm methanesulfonic acid; no poly(methyl methacrylate) thickener is used when a low-viscosity penetrating film is required for difficult-to-approximate wound edges, whereas 2–5 wt% thickener is added for gel-type applicators used on vertical surfaces. Conversion is carried out in a single-stage wiped-film evaporator at 0.5–1.5 kPa absolute and 150–180°C jacket temperature, with monomer vapour condensed into 316L stainless steel receivers that have been passivated with dilute nitric acid and dried with nitrogen. The filling line operates under dry nitrogen with a moisture specification of ≤0.05 wt% in the finished ampoule; terminal sterilisation by gamma irradiation or ethylene oxide is generally avoided because both processes can reduce stabiliser concentration and initiate premature polymerisation. Compliance requirements include ISO 10993-5:2009 for cytotoxicity, ISO 10993-10:2010 for irritation and sensitisation, and ISO 10993-1:2018 as the overall biological evaluation framework; mechanical wound-holding strength is assessed by ASTM F2255-05(2015) on a collagen substrate. Terminal product types include 1.0–3.0 mL low-density polyethylene ampoules for topical veterinary closure of canine and equine surgical incisions, superficial lacerations, and surgical drain sites. The documented boundary is topical application only: the adhesive should not be used in infected wounds or in deep puncture wounds where it may trap exudate, and alcohol-based skin preparation must be completely dried before application to avoid premature polymerisation. Published data for this specific veterinary configuration is limited; process validation should be conducted on the actual ampoule filling line with accelerated ageing at 40°C and 75% RH to establish shelf life.
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N-Octyl cyanoacetate, cyanoacetic acid n-octyl ester, is a clear low-volatility aliphatic ester intermediate with molecular formula C11H19NO2 and molecular weight 197.27 g/mol. The substance is registered under CAS 52688-08-1 and EC 258-117-5. A representative high-purity model designation is NOC-98, where the numeral reflects a minimum GC assay of ≥98.0%. Production typically proceeds by direct acid-catalyzed esterification of cyanoacetic acid with n-octanol, using azeotropic water removal under reduced pressure in a glass-lined batch reactor. The resulting liquid is handled as a hydrolytically reactive intermediate; the nitrile and ester functions are susceptible to hydrolysis under aqueous alkaline conditions, and residual moisture above the release limit can reduce downstream yield in base-sensitive coupling reactions.
For synthesis-grade material, incoming QC is organized around water, acidity, and assay because these variables govern behavior in subsequent Knoevenagel coupling and cyanoacrylate monomer synthesis. The table below lists the typical release ranges used for synthesis-grade material.
| Parameter | Typical Release Range | Test Reference |
|---|---|---|
| Assay by GC-FID | ≥98.0% area | Internal GC-FID method |
| Water content | ≤0.20% | ASTM E203-16 |
| Acid value | ≤0.50 mg KOH/g | ASTM D974-22 |
| Density at 20°C | 0.955–0.970 g/mL | ASTM D4052-22 |
| Refractive index n20/D | 1.440–1.446 | ASTM D1218-21 |
| Color, Pt-Co | ≤50 APHA | ASTM D1209-05(2019) |
At plant scale, the limiting variable in the esterification step is usually azeotropic water removal rather than intrinsic reaction rate. In a 5,000 L glass-lined reactor with a packed distillation column and decanter, cycle time is set by the overhead temperature profile and the rate of water separation from the n-octanol azeotrope; batch-to-batch variation in acid value is more commonly caused by incomplete neutralization or water carryover than by incomplete conversion. Material received with water content above 0.20% should be dried with molecular sieves or redistilled before use in moisture-sensitive condensations, because hydrolysis liberates cyanoacetic acid and n-octanol and raises the acid value above the 0.50 mg KOH/g ceiling.
The release density and refractive index windows also support rapid confirmation of ester chain length and absence of significant alcohol carryover. A density reading below 0.955 g/mL at 20°C can indicate excess n-octanol or incomplete esterification, while a refractive index above 1.446 can indicate higher-boiling impurities or water contamination. These limits are therefore used as supplementary incoming checks alongside GC assay, not as substitutes for chromatographic purity.
Relative to methyl cyanoacetate and ethyl cyanoacetate, the n-octyl ester exhibits a substantially lower saturated vapor pressure at ambient temperature. This difference reduces airborne lacrimatory exposure during drum charging and sampling; lower alkyl cyanoacetates are known to produce sharp, lachrymatory vapor at much lower ambient concentrations. The n-octyl chain also increases the normal boiling point and the boiling point at reduced pressure, which is operationally significant when a less volatile ester is required to remain in the reaction phase during high-vacuum distillation of volatile by-products.
In condensation chemistry, the longer ester chain introduces steric bulk at the oxygen-bearing carbon but does not eliminate the activated methylene reactivity of the cyanoacetate group. The practical consequence is that reactions may require slightly longer residence time or slightly higher catalyst loading than methyl or ethyl cyanoacetate for equivalent conversion, but the isolated condensation product has a higher boiling point and lower water solubility. Published kinetic data for the exact n-octyl/methyl rate ratio in industrial Knoevenagel conditions are limited, and process development laboratories generally establish catalyst loading empirically rather than relying on lower-homolog rate constants.
Compared with the branched 2-ethylhexyl cyanoacetate isomer, the linear n-octyl ester yields downstream condensation products with more ordered chain packing and a narrower melting range; the branched isomer is selected when lower viscosity or reduced crystallinity is required in the final polymeric derivative. Both esters share the same C8H17OCOCH2CN functional structure and similar hydrolytic sensitivity. The n-octyl derivative is also differentiated from n-butyl cyanoacetate by a larger lipophilic fragment, which lowers water solubility further and shifts the distillation window to higher vacuum-cut temperatures.
In the production of n-octyl cyanoacrylate monomer for medical and high-flexibility adhesive applications, N-octyl cyanoacetate is converted through a base-catalyzed Knoevenagel condensation with formaldehyde or paraformaldehyde. The condensed oligomer is then thermally cracked in a wiped-film or thin-film evaporator under absolute pressures below 2.0 kPa; the monomer vapor is drawn into a stabilized receiver containing an anionic polymerization inhibitor, typically sulfur dioxide at 50–500 ppm or methanesulfonic acid at equivalent acid strength. Published data for the exact depolymerization temperature profile of n-octyl cyanoacetate-derived oligomer are limited; typical industrial ranges for alkyl cyanoacrylate depolymerization fall between 150°C and 220°C, with the actual set point adjusted to maintain a steady monomer distillation rate without excessive residue formation.
The principal difference between N-octyl cyanoacetate and lower alkyl cyanoacetates in this application is the volatility window of the resulting monomer. n-Octyl cyanoacrylate monomer has a higher molecular weight and lower vapor pressure than methyl or ethyl cyanoacrylate, which makes high-vacuum distillation more demanding but reduces unwanted vapor exposure and gives the cured adhesive a more flexible, lower glass-transition temperature. The intermediate must therefore be supplied with low water and acid values; if the ester is hydrolyzed to cyanoacetic acid, the Knoevenagel catalyst is partially neutralized, and the yield of linear oligomer falls. Plant-scale experience shows that a moisture excursion above 0.30% in the intermediate can produce a visible haze in the condensation reactor and a measurable reduction in monomer yield after cracking, although the exact yield loss depends on catalyst buffer capacity and residual neutralization stoichiometry.
Downstream of cracking, the crude n-octyl cyanoacrylate monomer is often washed with aqueous sodium chloride and dried with anhydrous sodium sulfate before inhibitor adjustment. The intermediate ester is not present in the final adhesive; its primary role is to provide a stable, high-boiling cyanoacetate platform that can be converted to the monomer without the excessive volatility of methyl or ethyl cyanoacetate.
When a production-scale Knoevenagel condensation is run, the interaction between catalyst basicity, water content, and aldehyde addition rate creates a narrow processing window. The reaction is exothermic and is usually controlled at 60–90°C by staged addition of paraformaldehyde or formalin to a mixture of N-octyl cyanoacetate, solvent, and a catalytic amine such as piperidine or a hindered secondary amine. If the free water content exceeds 0.20%, the acid value rises and the amine catalyst is partially protonated; this slows the condensation and can shift the product distribution toward lower-molecular-weight oligomer. Conversely, excessive catalyst loading above the established range can initiate runaway condensation, producing a high-viscosity prepolymer that fouls the reactor walls and the downstream thin-film evaporator.
Equipment selection for this step is typically a glass-lined agitated reactor with external jacket cooling and an overhead condenser arranged for total reflux. The reaction mass is held under a nitrogen blanket, and the aldehyde source is added through a dip pipe or metering pump. Temperature is monitored at multiple internal points because the exotherm is greatest in the lower impeller zone; batch-to-batch variance in agitator speed can affect localized gel formation. The oligomer is then transferred to a wiped-film evaporator with a heated surface temperature profile that must remain below the residue decomposition threshold. If the film temperature is too high, the residue can crosslink and reduce heat-transfer efficiency; if the temperature is too low, monomer recovery is incomplete. Published data for the absolute threshold of N-octyl cyanoacetate-derived prepolymer are limited, but the practical operating band is established through a thermal mapping run after each significant viscosity change.
The activated methylene carbon of N-octyl cyanoacetate also participates in condensation with substituted benzaldehydes and heteroaryl aldehydes to form 2-cyano-3-aryl acrylates, which are evaluated as UV-absorbing intermediates and in heterocycle synthesis. In such reactions, the n-octyl chain improves solubility in aliphatic and aromatic hydrocarbon solvents and facilitates chromatographic isolation relative to methyl or ethyl esters. Reaction temperatures are commonly held between 60°C and 100°C with a catalytic amount of piperidine or ammonium acetate; published data for specific n-octyl arylidene yields are limited, and the solvent ratio and catalyst loading are optimized per substrate.
At ambient conditions, storage of N-octyl cyanoacetate requires exclusion of free water and avoidance of amine-based additives. The product is typically packaged in phenolic-lined steel or high-density polyethylene drums under a nitrogen headspace, with recommended storage temperatures between 5°C and 35°C. Pre-drying is required when relative humidity exceeds 60% during transfer, and all transfer lines should be purged with dry nitrogen before use. Incompatibilities include strong aqueous bases, primary and secondary amines, and strong oxidizing agents; primary or secondary amines can catalyze side reactions at the activated methylene position and should not be used as neutralization agents upstream of the condensation step. If the material is exposed to moisture in an open drum for more than 24 h, the acid value and water content should be re-verified before use in high-purity monomer synthesis.
For supply-chain documentation, synthesis-grade material is commonly accompanied by a certificate of analysis referencing the methods in the specification table. The GHS classification may vary by supplier and jurisdiction; safety data sheets should be consulted for country-specific exposure controls and disposal requirements. Heated transfers above 80°C should be conducted under local exhaust ventilation because the reduced-vapor-pressure advantage of the long-chain ester diminishes as temperature increases.
