STEARONITRILE

Stearonitrile is a saturated long-chain fatty nitrile derived from stearic acid and ammonia.
Stearonitrile is primarily used as a chemical intermediate for manufacturing octadecylamine, secondary fatty amines, tertiary fatty amines, and related surface-active derivatives.
Stearonitrile combines a reactive nitrile group with a hydrophobic C18 carbon chain, making purity, chain-length distribution, residual fatty acid, amide content, and degree of unsaturation important purchasing parameters.

CHEMICAL IDENTITY AND COMMON NAMES

Stearonitrile is the common oleochemical name for octadecanenitrile, a straight-chain aliphatic nitrile containing eighteen carbon atoms.
The nitrile carbon is included in the eighteen-carbon chain represented by the systematic name octadecanenitrile.

The historical name heptadecyl cyanide describes the same covalent organic nitrile structure.
Stearonitrile is not an inorganic cyanide salt and differs chemically from sodium cyanide, potassium cyanide, and other compounds containing free cyanide ions.

Synonyms and Common Names: Stearonitrile, Octadecanenitrile, Octadecanonitrile, n-Octadecanenitrile, n-Octadecanonitrile, 1-Cyanoheptadecane, Heptadecyl cyanide, n-Heptadecyl cyanide, Stearic acid nitrile, Stearic nitrile, Stearyl nitrile, Octadecyl nitrile, Octadecane nitrile, Octadecanoic acid nitrile, Octadecanoic acid, nitrile, Stearinsäurenitril, Stearinsaeurenitril, Oktadekannitril, Nitril kyseliny stearove, Stéaronitrile, NSC 5541

TECHNICAL IDENTIFICATION

CAS Number: 638-65-3
EC / EINECS Number: 211-345-3
Systematic Name: Octadecanenitrile
Molecular Formula: C18H35N
Linear Formula: CH3(CH2)16CN
Molar Mass: 265.48 g/mol
InChIKey: RHSBIGNQEIPSCT-UHFFFAOYSA-N
Canonical SMILES: CCCCCCCCCCCCCCCCCC#N

PHYSICAL AND CHEMICAL PROPERTIES

Appearance: White to almost white powder, crystals, or waxy solid
Physical State at 20 °C: Solid
Melting Point: 38–42 °C
Reduced-Pressure Boiling Point: 274 °C at 13.3 kPa
Density: 0.818 g/cm³ at 25 °C
Flash Point: Approximately 113 °C
Water Solubility: Insoluble
Solubility in Organic Solvents: Soluble in alcohol and very soluble in ether
Enthalpy of Fusion: 56.5 kJ/mol at 315.5 K
Volatility: Low at ambient temperature
Combustibility: Combustible solid
Chemical Stability: Stable under normal storage conditions
Thermal Decomposition Products: Carbon oxides, nitrogen oxides, and toxic nitrile-containing fumes

FUNCTIONAL CHARACTERISTICS

The carbon–nitrogen triple bond provides the principal reactive site in Stearonitrile.
Catalytic hydrogenation converts this nitrile group into a primary amine group while retaining the linear C18 hydrocarbon chain.

The long saturated alkyl chain dominates the solubility and interfacial behavior of Stearonitrile.
This structure produces strong hydrophobicity, negligible water solubility, affinity for nonaqueous organic media, and low ambient volatility.

The nitrile nitrogen acts as a hydrogen-bond acceptor, although the effect of the nitrile group on bulk solubility is outweighed by the seventeen-carbon alkyl segment.
Stearonitrile therefore behaves more like a waxy oleochemical intermediate than a conventional low-molecular-weight nitrile solvent.

Hydrolysis under sufficiently strong acidic or alkaline conditions converts Stearonitrile through stearamide toward stearic acid or its salts.
Controlled reduction produces octadecylamine, while reductive amination conditions can direct the reaction toward secondary or tertiary long-chain amines.

The melting range near 40 °C permits Stearonitrile to be processed either as a crystalline solid or as a low-temperature melt.
This phase behavior is useful for heated transfer, filtration, blending, and catalytic conversion.

PRODUCTION AND COMMERCIAL FORM

Stearonitrile is conventionally produced by reacting stearic acid with ammonia at elevated temperature.
The reaction proceeds through ammonium stearate and stearamide intermediates before dehydration forms the nitrile.

C17H35COOH + NH3 → C17H35CN + 2 H2O

Industrial fatty-nitrile production commonly operates at approximately 300–380 °C with continuous removal of reaction water.
Alumina and selected metal oxides can facilitate dehydration and improve conversion of intermediate fatty amides into nitriles.

Efficient water removal drives the equilibrium toward nitrile formation and limits hydrolysis back to stearamide or stearic acid.
Reduced-pressure distillation can remove residual acid, amide, low-boiling material, and heavy reaction products.

Purified stearic acid produces a C18-rich Stearonitrile grade.
Natural fatty-acid streams can produce mixtures containing palmitonitrile, oleonitrile, and other chain-length homologues alongside Stearonitrile.

Commercial reagent and technical materials are commonly supplied as white to almost white powder or crystals with minimum gas-chromatographic assays around 90–92%.
Higher-purity and narrowly defined C18 grades support selective synthesis, physical-property research, and production of high-purity octadecylamine.

APPLICATIONS AND INDUSTRIES

FATTY AMINE PRODUCTION

Stearonitrile serves primarily as the direct precursor to octadecylamine, also known as stearylamine.
Catalytic hydrogenation converts the –C≡N group into –CH2NH2 without shortening the hydrocarbon chain.

Ammonia-containing hydrogenation conditions favor formation of the primary fatty amine by suppressing condensation reactions that generate secondary amines.
Catalyst selection, hydrogen pressure, temperature, ammonia concentration, water content, and feed purity influence conversion and product selectivity.

Octadecylamine produced from Stearonitrile is an important intermediate for cationic surfactants, emulsifiers, flotation collectors, corrosion inhibitors, antistatic agents, lubricant additives, and surface-treatment chemicals.
The C18 chain provides strong adsorption to hydrophobic surfaces and contributes to persistent interfacial films in downstream amine products.

SECONDARY AND TERTIARY FATTY AMINES

Stearonitrile supports the controlled manufacture of secondary and tertiary long-chain amines through hydrogenation and reductive amination chemistry.
Reaction conditions can be adjusted to promote coupling with primary or secondary amines rather than exclusive formation of octadecylamine.

The resulting fatty amines can be converted into quaternary ammonium compounds used in fabric softeners, hair-conditioning ingredients, antistatic formulations, and industrial surface modifiers.
These applications belong to the amine and quaternary derivatives produced from Stearonitrile rather than to direct addition of the nitrile itself.

SURFACTANTS AND PROCESS CHEMICALS

Stearonitrile contributes indirectly to surfactant production by providing the hydrophobic C18 segment of fatty amine derivatives.
After conversion into an amine, amine salt, amine oxide, or quaternary ammonium compound, the molecule acquires the polar or ionic head group needed for surface activity.

These derivatives are incorporated into mineral-flotation systems, bitumen and asphalt emulsions, textile-treatment products, metal-protection formulations, lubricants, fuel additives, and industrial cleaning systems.
Chain-length purity affects adsorption strength, melting behavior, solubility, and formulation temperature in these downstream products.

ORGANIC SYNTHESIS

High-purity Stearonitrile functions as a long-chain building block in organic synthesis.
The nitrile group can be reduced, hydrolyzed, or subjected to carbon–carbon bond-forming reactions while the saturated C18 chain supplies a defined hydrophobic segment.

Stearonitrile is particularly useful in research involving long-chain amines, lipophilic intermediates, molecular assemblies, and surface-active derivatives.
A narrow homologue profile is important when the physical behavior of the final product depends on a precise alkyl-chain length.

SURFACE AND MONOLAYER RESEARCH

Stearonitrile is used as a model long-chain nitrile in studies of molecular packing, monolayers, phase separation, and interfacial organization.
Its behavior has been examined in mixtures with stearic acid and phospholipids at air–water interfaces.

The saturated hydrocarbon chain supports ordered molecular packing, while the compact nitrile group provides a polar terminus without ionization under neutral conditions.
This combination makes Stearonitrile useful for comparing the packing effects of nitrile, carboxylic acid, alcohol, and phospholipid head groups.

PHASE-TRANSITION RESEARCH

The melting range near 40 °C and the measurable enthalpy of fusion support research into Stearonitrile-containing phase-transition systems.
Mixtures with other long-chain compounds can display composition-dependent solid–liquid behavior and altered melting transitions.

This use is principally associated with thermal analysis, phase-equilibrium research, and specialized material development.
Fatty-amine manufacture remains the main established industrial role of Stearonitrile.

GRADE SELECTION AND PRODUCT SUITABILITY

Technical-grade Stearonitrile is suitable for process development and fatty-amine production when the downstream operation can accommodate a defined amount of related fatty nitriles and reaction intermediates.
Gas-chromatographic assay, total C18 content, homologue distribution, acid value, amide content, iodine value, moisture, and color provide meaningful measures of technical-grade quality.

High-C18 Stearonitrile supports production of octadecylamine with a narrow alkyl-chain distribution.
A broader fatty-nitrile composition produces a corresponding mixture of fatty amines with different melting points, solubilities, and surface properties.

Research-grade Stearonitrile is selected for structural analysis, monolayer studies, thermal characterization, and reactions requiring a defined molecular species.
A sharp melting range, confirmed molecular structure, low color, and high chromatographic purity are especially useful for these applications.

Residual stearic acid is measured through acid value and can affect catalyst consumption, corrosion, reaction pH, and downstream amine purification.
Residual stearamide indicates incomplete dehydration and can remain unconverted during nitrile hydrogenation.

Iodine value measures unsaturation arising from oleonitrile or other unsaturated homologues.
A low iodine value supports oxidative stability and a predominantly saturated fatty-nitrile composition.

Moisture control is important for catalytic hydrogenation and other moisture-sensitive transformations.
Metal impurities, catalyst residues, and inorganic solids require tighter control when Stearonitrile is used with selective hydrogenation catalysts.

FORMULATION AND PROCESS CONSIDERATIONS

Stearonitrile can be melted slightly above its 38–42 °C melting range for pumping, filtration, and reactor charging.
Maintaining the transfer temperature only as high as needed for dependable flow limits unnecessary thermal exposure.

Heated vessels, insulated lines, and temperature-controlled valves help prevent crystallization during molten transfer.
Cooling within unheated transfer equipment can cause solidification, blockage, and uneven charging.

Solid Stearonitrile can cake or fuse when stored above its melting range.
Cool storage and packaging that protects the crystalline form support easier weighing, sampling, and batch addition.

Water is undesirable during high-temperature nitrile formation because water shifts the reaction sequence toward fatty acid, ammonium soap, and amide intermediates.
Moisture can also affect the activity and selectivity of catalysts used in downstream hydrogenation.

Stearonitrile is insoluble in water and therefore requires a compatible organic medium when solution processing is necessary.
Ether, warmed alcohol, and other validated nonaqueous solvents can support laboratory dissolution and reaction handling.

Hydrogenation conditions determine whether Stearonitrile forms predominantly octadecylamine or a mixture containing secondary and tertiary amines.
Ammonia commonly increases selectivity toward the primary amine, while catalyst surface properties also influence condensation and hydrogenation rates.

QUALITY, SPECIFICATIONS AND DOCUMENTATION

Gas chromatography provides the principal assay for Stearonitrile and separates Stearonitrile from related fatty nitrile homologues.
Chromatographic composition is especially important when chain-length distribution controls the identity and performance of the resulting fatty amine.

Infrared spectroscopy identifies the characteristic nitrile functionality, while nuclear magnetic resonance confirms the linear saturated structure.
Mass spectrometry can support identity testing and investigation of related homologues or organic impurities.

Melting-range analysis provides a rapid indication of composition and purity.
Unsaturated homologues, shorter-chain nitriles, residual acid, and residual amide can broaden or shift the melting interval.

Useful purchasing parameters include appearance, assay, C18 content, fatty-nitrile distribution, melting range, acid value, amide content, iodine value, moisture, color, and residual metals.
Production of high-purity octadecylamine benefits from particularly close control of acid, amide, water, and unsaturated components.

The Certificate of Analysis should state the lot number, assay method, chromatographic purity, appearance, and agreed application-specific parameters.
The Technical Data Sheet defines product characteristics and processing information, while the Safety Data Sheet provides hazard, handling, storage, transport, and emergency-response information for the supplied grade.

SAFETY AND REGULATORY CONSIDERATIONS

Stearonitrile can be harmful through inhalation and skin contact and can irritate the eyes and respiratory tract.
Dust, aerosols, vapors from heated material, and direct contact with molten Stearonitrile should be controlled.

Stearonitrile is a combustible organic solid with a flash point of approximately 113 °C.
Keep Stearonitrile away from flames, sparks, hot surfaces, and other ignition sources.

Thermal decomposition and combustion can produce toxic carbon oxides, nitrogen oxides, and nitrile-containing fumes.
Firefighters require full protective equipment and self-contained breathing apparatus.

Safety goggles, chemical-resistant gloves, protective clothing, and suitable respiratory protection provide the principal personal controls.
Local exhaust ventilation is appropriate for powder handling, heated transfer, sampling, and reactor charging.

Spilled solid should be collected without generating dust and placed in a closed compatible container.
Molten releases can be contained with inert material, and all releases should be prevented from entering drains, soil, and surface water.

FIRST AID

Inhalation: Move the affected person to fresh air, keep the person at rest, and obtain medical attention if breathing difficulty, coughing, or irritation occurs.
Skin Contact: Remove contaminated clothing and wash the skin thoroughly with soap and water.
Skin Contact with Molten Material: Cool the affected area immediately with running water and obtain medical attention without pulling solidified material from the skin.
Eye Contact: Rinse cautiously with clean water for at least 15 minutes, remove contact lenses when easy to do, and obtain medical attention if irritation continues.
Ingestion: Rinse the mouth, do not induce vomiting, and contact a physician or poison center promptly.
Note to Physicians: Provide supportive and symptomatic treatment with attention to respiratory irritation, dermal exposure, thermal burns, and inhalation of decomposition products.

HANDLING AND STORAGE

Handling: Avoid breathing dust or heated vapors and prevent contact with the eyes, skin, and clothing.
Ventilation: Use effective general ventilation and local exhaust at charging, melting, sampling, and transfer points.
Storage: Store Stearonitrile in a tightly closed container in a cool, dry, dark, and well-ventilated area below its melting range.
Incompatibilities: Keep Stearonitrile separate from strong oxidizing agents, excessive heat, flames, sparks, and other ignition sources.
Molten Handling: Use temperature-controlled equipment and prevent solidification inside pumps, valves, filters, and transfer lines.
Hygiene: Wash thoroughly after handling and keep Stearonitrile away from food, beverages, and animal feed.
Packaging: Use clean, dry, tightly sealed, chemically compatible packaging that protects Stearonitrile from moisture, contamination, heat, and physical damage.

PACKAGING AND PROCUREMENT CONSIDERATIONS

Stearonitrile can be supplied in packages selected for research, pilot, or industrial consumption.
Package design should account for the low melting range because exposure to elevated transport or warehouse temperatures can fuse crystals into a solid mass.

Procurement requests should state the required assay, C18 content, homologue profile, melting range, acid value, amide content, iodine value, moisture limit, color requirement, package size, and intended conversion process.
Buyers producing octadecylamine should place particular emphasis on saturated C18 content, catalyst-sensitive impurities, and primary-amine selectivity requirements.

For technical information, grade selection, specifications, documentation, packaging, or supply requirements concerning Stearonitrile, contact Ataman Kimya at +90 216 577 10 10 or info@atamankimya.com.