PRODUCTS

OLEONITRILE

Oleonitrile is used in the production of biofuel and biochar by thermal pyrolysis of linseed seed.
Oleonitrile is also used as a fatty nitrile solvent for agricultural formulations.
Oleonitrile is widely used in the manufacture of oleylamine, surfactants, corrosion inhibitors, lubricants, textile auxiliaries, flotation agents, and other specialty chemicals.

CAS Number:3688-25-7
EC Number: 222-995-8
Molecular Formula: C₁₈H₃₃N
Molecular Weight: 263.46 g/mol

SYNONYMS:
Oleonitrile, (Z)-octadec-9-enenitrile, 112-91-4, Oleoylnitrile, Oleylonitrile, Oleic acid nitrile, Oleic nitrile, 9-Octadecenenitrile, (9Z)-, Oleyl nitrile, (Z)-9-OCTADECENENITRILE, 9-Octadecenenitrile, (Z)-, Olsaeurenitril, (9Z)-octadec-9-enenitrile, Olsaeurenitril [German], HSDB 5580, EINECS 204-016-0, BRN 1102081, 9-Octadecenoic acid (cis), nitrile (cis), cis-9-octadecenenitrile, 59F4912BUE, DTXSID3026934, CHEBI:133637, EC 204-016-0, 4-02-00-01668 (Beilstein Handbook Reference), (Z)-9-OCTADECENENITRILE [HSDB], (Z)9Octadecenenitrile, RefChem:408679, 9Octadecenenitrile, (Z), DTXCID906934, 9Octadecenoic acid (cis), nitrile (cis), 9-OCTADECENOIC ACID(CIS), NITRILE(CIS), 204-016-0, Oleanitrile, olenitrile, UNII-59F4912BUE, C18H33N, cis-octadec-9-enenitrile, SCHEMBL1958159, MFCD01711190, DB-255881, NS00009749, 9-Octadecenenitrile (1mg/mL in Acetonitrile), 9-Octadecenenitrile (1 mg/mL in Acetonitrile), Q27261698, oleonitrile, Oleyl nitrile, Oleylonitrile, Oleoylnitrile, (Z)-9-Octadecenenitrile, 9-Octadecenenitrile, (9Z)-, 9-Octadecenenitrile (1 mg/mL in Acetonitrile), Oleic acid nitrile, Oleic nitrile, Oleyl nitrile, Oleoylnitrile, Oleonitrile, (Z)-9-Octadecenenitrile, 4-02-00-01668 (Beilstein Handbook Reference), 9-Octadecenenitrile, (Z)-, 9-Octadecenoic acid (cis), nitrile (cis), BRN 1102081, HSDB 5580, Oleic acid nitrile, Oleic nitrile, Oleonitrile, Oleoylnitrile, Oleyl nitrile, Oleylonitrile, Olsaeurenitril, Olsaeurenitril [German], 9-Octadecenenitrile, (9Z)-, (9Z)-octadec-9-enenitrile, 9-Octadecenenitrile,(9Z)-, Oleonitrile, 9-Octadecenenitrile,(Z)-, (9Z)-9-Octadecenenitrile, Oleic acid nitrile, Oleylonitrile, Oleoylnitrile, Oleic nitrile, Oleyl nitrile, Arneel O, oleonitrile, Oleyl nitrile, 9-Octadecenenitrile, (9Z)-, (Z)-9-Octadecenenitrile, Oleoylnitrile, Oleylonitrile, 9-Octadecenenitrile (1 mg/mL in Acetonitrile), (9Z)- octadec-9-enenitrile, (Z)- octadec-9-enenitrile, (Z)-9- octadecenenitrile, 9- octadecenenitrile, (9Z)-, 9- octadecenenitrile, (Z)-, oleanitrile, oleic acid nitrile, oleic nitrile, oleonitrile, oleoylnitrile, oleyl nitrile, oleylonitrile, (Z)-9-OCTADECENENITRILE [HSDB], 9-OCTADECENENITRILE, (9Z)-, 9-OCTADECENENITRILE, (Z)-, OLEIC ACID NITRILE, OLEIC NITRILE, OLEONITRILE, OLEOYLNITRILE, Oleonitrile, (Z)-octadec-9-enenitrile, 112-91-4, 9-Octadecenenitrile, (9Z)-, Oleic acid nitrile, Oleoylnitrile, Oleic nitrile, Oleylonitrile, Oleyl nitrile, (Z)-9-OCTADECENENITRILE, 9-Octadecenenitrile, (Z)-, Olsaeurenitril, Olsaeurenitril [German], (9Z)-octadec-9-enenitrile, HSDB 5580, EINECS 204-016-0, BRN 1102081, UNII-59F4912BUE, 9-Octadecenoic acid (cis), nitrile (cis), 59F4912BUE, EC 204-016-0, 4-02-00-01668 (Beilstein Handbook Reference), olenitrile, Oleanitrile, cis-9-octadecenenitrile, cis-octadec-9-enenitrile, SCHEMBL1958159, DTXSID3026934, C18H33N, CHEBI:133637, C18-H33-N, (Z)-9-OCTADECENENITRILE [HSDB], LS-97739, Q27261698, Oleonitrile, Oleic Acid Nitrile, Oleic Nitrile, Oleyl Nitrile, Oleoylnitrile, cis-9-Octadecenenitrile, (Z)-Octadec-9-enenitrile, Octadec-9-enenenitrile

Oleonitrile is a long-chain unsaturated aliphatic nitrile derived from oleic acid, one of the most abundant naturally occurring fatty acids found in vegetable oils such as rapeseed, sunflower, soybean, and olive oil, as well as in animal fats.
Its IUPAC name is (Z)-Octadec-9-enenitrile, and Oleonitrile consists of an 18-carbon hydrocarbon chain containing one naturally occurring cis (Z) double bond and a terminal nitrile (-C≡N) functional group.

At room temperature, Oleonitrile appears as a colorless to pale yellow oily liquid with a mild fatty odor.
Oleonitrile combines the hydrophobic character of a long fatty chain with the chemical reactivity of a nitrile group, making it an important industrial intermediate.
Oleonitrile is a long-chain unsaturated aliphatic nitrile derived from oleic acid, one of the most abundant naturally occurring fatty acids found in vegetable oils and animal fats.

Oleonitrile's IUPAC name is (9Z)-Octadec-9-enenitrile, and it consists of an 18-carbon chain containing one cis double bond and a terminal nitrile (-C≡N) functional group.
At room temperature, Oleonitrile appears as a pale yellow to colorless oily liquid with a mild characteristic odor.
Oleonitrile is an important industrial intermediate used in the production of fatty amines, surfactants, lubricants, corrosion inhibitors, textile chemicals, flotation agents, and specialty chemical formulations.

Its combination of a hydrophobic hydrocarbon chain and a reactive nitrile group makes Oleonitrile valuable for further chemical transformations, particularly hydrogenation to primary fatty amines.
Oleonitrile is a fatty nitrile obtained by formal condensation of oleic acid with ammonia.
Oleonitrile has a role as a plant metabolite.

Oleonitrile is a fatty nitrile and an olefinic compound.
Oleonitrile is functionally related to an oleic acid.
Oleonitrile, also known as 9-octadecenitrile, is a long-chain aliphatic nitrile with the chemical formula C18H35N.

Oleonitrile is characterized by its linear structure, featuring a long hydrocarbon chain with a nitrile functional group (-C≡N) at one end.
Oleonitrile is typically a colorless to pale yellow liquid at room temperature and has a relatively high boiling point due to its long carbon chain.
Oleonitrile is insoluble in water but soluble in organic solvents, making it useful in various applications, including as a lubricant and in the synthesis of other organic compounds.

The presence of the nitrile group imparts unique chemical reactivity, allowing oleonitrile to participate in reactions such as hydrolysis and reduction.
Additionally, oleonitrile is of interest in the field of materials science and can be used in the production of polymers and surfactants.
Oleonitrile (CAS 112-91-4, (Z)-9-Octadecenenitrile) is an unsaturated C18 fatty nitrile derived from the formal condensation of oleic acid with ammonia.

As a member of the long-chain fatty nitrile class, Oleonitrile features a cis-configured carbon-carbon double bond at the C9 position within an 18-carbon backbone terminated by a nitrile (-CN) functional group.
Oleonitrile (9Z-octadecenenitrile, CAS 112-91-4) is a long-chain, unsaturated aliphatic fatty nitrile derived from oleic acid.

Characterized by a cis-double bond at the C9 position, Oleonitrile is a liquid at standard room temperature, exhibiting a melting point of approximately -1 °C and a density of 0.842–0.848 g/cm³.
In industrial procurement, oleonitrile is primarily sourced as a liquid-state, non-acidic, aprotic polar intermediate for the synthesis of oleylamine, specialized low-foam nonionic surfactants, and low-temperature lubricant additives .

USES and APPLICATIONS of OLEONITRILE:
Oleonitrile is used in the production of biofuel and biochar by thermal pyrolysis of linseed seed.
Oleonitrile is also used as a fatty nitrile solvent for agricultural formulations.
Mining Industry: Derivatives of Oleonitrile are used as flotation reagents during mineral processing, where they improve selective separation of valuable ores from gangue materials.

Organic Chemical Synthesis: Oleonitrile is widely used as a synthetic intermediate for manufacturing long-chain amines, quaternary ammonium compounds, specialty surfactants, industrial additives, and fine chemical products.
Oleonitrile is widely used in the manufacture of oleylamine, surfactants, corrosion inhibitors, lubricants, textile auxiliaries, flotation agents, and other specialty chemicals.

Because it is produced primarily from renewable fatty acid feedstocks, Oleonitrile is also considered an important bio-based chemical intermediate.
Oleonitrile is used in the production of biofuel and biochar by thermal pyrolysis of linseed seed.
Oleonitrile is also used as a fatty nitrile solvent for agricultural formulations.

-Fatty Amine Production uses of Oleonitrile:
The largest commercial application of Oleonitrile is the production of Oleylamine through catalytic hydrogenation.
Oleylamine is widely used in numerous industrial sectors because it serves as a versatile intermediate for surfactants, emulsifiers, flotation agents, corrosion inhibitors, and lubricant additives.
This conversion represents one of the most economically important uses of Oleonitrile.

-Surfactant Manufacturing uses of Oleonitrile:
Oleonitrile serves as an intermediate in manufacturing specialty surfactants that provide excellent emulsifying, wetting, dispersing, and antistatic properties.
These surfactants are incorporated into detergents, industrial cleaners, textile auxiliaries, agricultural formulations, and personal care ingredients.

-Corrosion Inhibitors uses of Oleonitrile:
Long-chain nitrile derivatives are valuable components of corrosion protection systems because they form hydrophobic films that reduce moisture and corrosive agent contact with metal surfaces.
They are used in oilfield chemicals, pipelines, industrial equipment, cooling systems, and metalworking fluids.

-Lubricants and Metalworking uses of Oleonitrile:
Oleonitrile contributes excellent lubricating performance because its long hydrocarbon chain adsorbs effectively onto metal surfaces.
Oleonitrile is used in specialty lubricants, friction modifiers, anti-wear additives, and industrial metal-processing formulations.

-Textile Industry uses of Oleonitrile:
Oleonitrile functions as an intermediate for textile finishing chemicals that improve fiber processing and fabric performance.
Applications of Oleonitrile include antistatic treatments, fiber lubrication, textile softening, and specialty finishing formulations.

BENEFITS of OLEONITRILE:
Oleonitrile offers numerous advantages across industrial applications.
Oleonitrile's long hydrocarbon chain provides excellent lubricating properties and strong compatibility with hydrocarbon-based formulations, while the nitrile group enables efficient chemical conversion into higher-value products.
The cis double bond improves fluidity, making handling and processing easier than with fully saturated long-chain nitriles.

Additional benefits of Oleonitrile include:
renewable raw material origin,
excellent precursor for Oleylamine production,
low volatility,
high thermal stability,
strong hydrophobic character,
compatibility with numerous organic solvents,
versatility in chemical synthesis,
suitability for large-scale manufacturing.

CHEMICAL BEHAVIOR of OLEONITRILE:
The nitrile group is the principal reactive site of Oleonitrile, while the long unsaturated hydrocarbon chain contributes flexibility, lubricity, and hydrophobicity.
Oleonitrile is chemically stable under ordinary storage conditions but reacts readily under catalytic or strongly reactive conditions.

Oleonitrile undergoes several important chemical reactions:
*catalytic hydrogenation to produce Oleylamine, one of its most important commercial derivatives,
*reduction to long-chain primary amines,
*hydrolysis under strongly acidic or alkaline conditions to form corresponding fatty acid derivatives,
*reactions at the carbon-carbon double bond such as hydrogenation, epoxidation, and oxidation,
*oxidation under aggressive oxidizing conditions affecting both the double bond and the nitrile functionality.
Unlike many low-molecular-weight nitriles, Oleonitrile is relatively stable because of its long carbon chain and low volatility.

CHARACTERISTICS of OLEONITRILE:
Oleonitrile possesses several distinctive characteristics that make it valuable in industrial manufacturing.
Oleonitrile is:

derived from renewable fatty acid feedstocks,
highly hydrophobic,
chemically versatile,
low-volatility,
thermally stable,
lubricating,
flexible because of its cis double bond,
an efficient precursor for specialty amines,
suitable for large-scale industrial processing.
The naturally occurring cis double bond prevents tight molecular packing, giving Oleonitrile greater fluidity than saturated C18 nitriles.

PHYSICAL and CHEMICAL PROPERTIES of OLEONITRILE:
Molecular Weight: 263.5 g/mol
XLogP3: 7.1
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 14
Exact Mass: 263.261300057 Da
Monoisotopic Mass: 263.261300057 Da
Topological Polar Surface Area: 23.8 Å²
Heavy Atom Count: 19
Formal Charge: 0
Complexity: 233
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0

Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
CBNumber: CB3885123
Molecular Formula: C18H33N
Molecular Weight: 263.46
MDL Number:
MOL File: 112-91-4.mol
Melting point: -1°C
Boiling point: 401.7°C (estimate)

Density: 0.8470
vapor pressure: 1.8Pa at 20℃
refractive index: 1.4566
solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
form: Oil
color: Colourless to Pale Yellow
Stability: Light Sensitive
LogP: 5.08 at 21℃
FDA UNII: 59F4912BUE
EPA Substance Registry System: 9-Octadecenenitrile, (9Z)- (112-91-4)
Density: 0.842g/cm3
Boiling point: 385.6°C at 760 mmHg

Refractive index: 1.458
Flash point: 191.1°C
Vapour Pressur: 3.76E-06mmHg at 25°C
Molecular Weight: 263.469
Exact Mass: 263.46
EC Number: 204-016-0
PSA: 23.8
XLogP3: 7.1
Appearance: Liquid
Density: 0.848 g/cm3 @ Temp: 17 °C
Melting Point: -1 °C
Boiling Point: 330-335 °C
Refractive Index: 1.4566
Water Solubility: INsoluble IN WATER; soluble IN ALCOHOL

CAS No. 112-91-4
Molecular Formula C18H33N
Molecular Weight 263.5 g/mol
IUPAC Name (Z)-octadec-9-enenitrile
Standard InChI InChI=1S/C18H33N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h9-10H,2-8,11-17H2,1H3/b10-9-
Standard InChI Key UIAMCVSNZQYIQS-KTKRTIGZSA-N
Isomeric SMILES CCCCCCCC/C=C\CCCCCCCC#N
SMILES CCCCCCCCC=CCCCCCCCC#N
Canonical SMILES CCCCCCCCC=CCCCCCCCC#N
Melting Point -1.0 °C -1 °C
Density 0.842g/cm3
Boiling Point 385.6ºC at 760mmHg

Melting Point -1ºC
Molecular Formula C18H33N
Molecular Weight 263.46100
Flash Point 191.1ºC
Exact Mass 263.26100
PSA 23.79000
LogP 6.54748
Vapour Pressure 3.76E-06mmHg at 25°C
Index of Refraction 1.458
InChIKey UIAMCVSNZQYIQS-KTKRTIGZSA-N
SMILES CCCCCCCCC=CCCCCCCCC#N
ECHA EINECS - REACH Pre-Reg: 204-016-0
FDA UNII: 59F4912BUE
Nikkaji Web: J193.607G

Beilstein Number: 1102081
XlogP3: 7.10 (est)
Molecular Weight: 263.46801000
Formula: C18 H33 N
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: -1.00 °C. @ 760.00 mm Hg
Boiling Point: 385.61 °C. @ 760.00 mm Hg (est)
Flash Point: 376.00 °F. TCC ( 191.10 °C. ) (est)
logP (o/w): 7.409 (est)
Soluble in:
water, 0.004277 mg/L @ 25 °C (est)

Appearance: Colorless to pale yellow oily liquid.
Odor: Mild fatty characteristic odor.
Physical State: Liquid at room temperature.
Molecular Formula: C₁₈H₃₃N.
Molecular Weight: 263.46 g/mol.
CAS Number: 112-91-4.
EC Number: 204-016-0.
Density: 0.842–0.847 g/cm³ at 20°C.
Melting Point: Approximately −1°C.
Boiling Point: Approximately 385.6°C at 760 mmHg.
Flash Point: Approximately 191°C.

Autoignition Temperature: Not consistently reported in major databases.
Vapor Pressure: Approximately 1.8 Pa at 20°C (very low).
Refractive Index: 1.4566 at 20°C.
Color: Water-white to pale yellow.
Viscosity: Moderately viscous.
Volatility: Very low under ambient conditions.
Chemical Class: Long-chain unsaturated aliphatic nitrile.
Functional Group: Nitrile (-C≡N).
Carbon Chain Length: 18 carbon atoms.
Double Bond Position: Carbon 9.

Double Bond Configuration: cis (Z).
Saturation: Monounsaturated.
Polarity: Predominantly nonpolar with a polar nitrile group.
Water Solubility: Practically insoluble.
Solubility: Soluble in ethanol, acetone, ether, benzene, toluene, and many organic solvents.
LogP (Octanol/Water Partition): High, indicating strong lipophilicity.
Hydrogen Bond Donor Count: 0.
Hydrogen Bond Acceptor Count: 1.
Rotatable Bond Count: 15.
Topological Polar Surface Area: Approximately 23.8 Å².
Exact Mass: 263.261 Da.
Heavy Atom Count: 19.
Formal Charge: 0.

FIRST AID MEASURES of OLEONITRILE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of OLEONITRILE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.

FIRE FIGHTING MEASURES of OLEONITRILE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of OLEONITRILE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of OLEONITRILE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.

STABILITY and REACTIVITY of OLEONITRILE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available

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