METHYL OLEATE

METHYL OLEATE

cas no : 112-62-9

SYNONYM : METHYL OLEATE; 112-62-9; Methyl cis-9-octadecenoate; Oleic acid methyl ester; Edenor MeTiO5; Methyl (Z)-9-octadecenoate; Oleic acid, methyl ester; methyl-cis-oleate; Exceparl M-OL; Emery, oleic acid ester; Esterol 112; Priolube 1403; Witconol 2301; Emery oleic acid ester 2301; Emery 2301; Edenor Me 90/95V; cis-9-Octyldecenoic acid, methyl ester; Methyl 9-octadecenoate; Oleic acid, methyl ester, cis-; 61788-34-9; Methyl oleate, technical; Methyl 9-(Z)-octadecenoate; Methyl cis-9-octadecenoate.; cis-oleic acid methyl ester; methyloleate; methyl oleoate; methyl (Z)-octadec-9-enoate; methyl oleat; Oleic acid, cis-; INECS 262-969-8; Methyl oleate, 99%; Oleic acid-methyl ester; Methyl Z-9-octadecenoate; Methyl oleate, tech grade; 9-Octadecenoic acid (9Z)-, methyl ester, sulfurized, copper-treated; (Z)-9-Methyl octadecenoate; Methyl 9-octadecenoate, cis-; Methyl (9Z)-9-octadecenoate; Methyl oleate, analytical standard; 9-Octadecenoic acid (Z)-, methyl ester, sulfurized, copper-treated; Methyl oleate, technical grade, 70%; cis-9-Octadecenoic acid, methyl ester; 9-octadecenoic acid, methyl ester (Z); Methyl cis-9-octadecenoate, Oleic acid methyl ester; Oleic acid, methyl ester; Emery oleic acid ester 2301; Methyl cis-9-octadecenoate; Methyl oleate; Emery; Emery, oleic acid ester; Methyl 9-octadecenoate; Oleic acid, methyl ester, cis-; Emerest 2301; Emerest 2801; Kemester 105; Kemester 115; Kemester 205; Kemester 213; Methyl (Z)-9-octadecenoate; Emery 2219; Emery 2301; Kemester 104; Methyl cis-9-octadecanoate; Priolube 1400; Witconol 2301; Methyl (9Z)-9-octadecenoate; C18:1 (oleate); C18:1 n9 cis; C18:1 n9

Experimental Properties    
Physical Description    
Oleic acid methyl ester is a clear to amber liquid. Insoluble in water. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
CAMEO Chemicals
Liquid

EPA Chemicals under the TSCA
Color/Form    
Colorless to amber clear liquid

Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 775
Hazardous Substances Data Bank (HSDB)
Odor    
Faint fatty odor

Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 775
Hazardous Substances Data Bank (HSDB)
Boiling Point    
425.3 °F at 20 mm Hg (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
CAMEO Chemicals
218.5 °C @ 20 mm Hg

Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 76th ed. Boca Raton, FL: CRC Press Inc., 1995-1996., p. 3-228
Hazardous Substances Data Bank (HSDB)

Melting Point    
-3.8 °F (NTP, 1992)
-19.9 °C

Solubility    
Insoluble (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
CAMEO Chemicals
Insol in water; miscible with ethyl alcohol, ether; sol in chloroform

Density    HelpNew Window
0.8739 (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
CAMEO Chemicals
0.8739 @ 20 °C

Vapor Pressure    HelpNew Window
6.29e-06 mmHg

EPA DSSTox
6.29X10-6 at 25 °C

Decomposition
When heated to decomposition it emits acrid smoke and irritating fumes.

Viscosity    
Viscosity coefficients = 4.88, 2.62, and 1.64 cP at 30, 60, and 90 °C, respectively

Heat of Combustion    
At constant volume, delta Ec = -2837.3 kcal/mol at 25 °C
Heat of Vaporization
20.17 kcal/mol at 1 torr
Surface Tension    
31.3 dyne/cm at 25 °C; 25.4 dyne/cm at 100 °C; 19.1 dyne/cm at 180 °C
Other Experimental Properties    
Boiling point - 217 °C at 16 torr (decomposes)
Riddick, J.A., W.B. Bunger, Sakano T.K. Techniques of Chemistry 4th ed., Volume II. Organic Solvents. New York, NY: John Wiley and Sons., 1985., p. 424
Hazardous Substances Data Bank (HSDB)
Standard heat of formation = -173.91 kcal/mol at 25 °C

Use Classification    
EPA Safer Chemical Functional Use Classes -> Solvents

EPA Safer Choice
Safer Chemical Classes -> Yellow triangle Yellow triangle - The chemical has met Safer Choice Criteria for its functional ingredient-class, but has some hazard profile issues

EPA Safer Choice
Food additives -> Flavoring Agents

EU Food Improvement Agents
Fatty Acyls [FA] -> Fatty esters [FA07] -> Wax monoesters [FA0701]

LIPID MAPS
Cosmetics -> Emollient; Skin conditioning

S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118
NORMAN Suspect List Exchange

Category
Category Description
Categorization Type
Agricultural    Relating to agricultural, including the raising and farming of animals and growing of crops    CPCat Cassette
Consumer_use    Term applied when the only information the source indicates is 'consumer' or 'consumer product' ; also applied to terms that the source indicates are f     CPCat Cassette
Fluid_property_modulator    Includes antifoaming agents, coagulating agents, dispersion agents, emulsifiers, flotation agents, foaming agents, viscosity adjustors, etc    CPCat Cassette
Food_additive, flavor    General flavoring agents used in foods, including condiments and seasonings    CPCat Cassette
Food_contact    Includes food packaging, paper plates, cutlery, small appliances such as roasters, etc.; does not include facilities that manufacture food    CPCat Cassette
Fragrance, consumer_use    Term applied when the only information the source indicates is 'consumer' or 'consumer product' ; also applied to terms that the source indicates are for consumer use, yet the descriptor term is ambivalent about usage (e.g., cleaning_washing products may be for industrial or consumer use, when the source indicates consumer use, the consumer_use term is also applied) - see appendix for full list of unambiguous consumer related terms plus ambiguous consumer related terms which if indicated are labeled with 'consumer_use'     CPCat Cassette
Industrial_manufacturing        CPCat Cassette
Inert        CPCat Cassette
Ink, colorant    Term used for colorants, dyes, or pigments; includes colorants for drugs, textiles, personal care products (cosmetics, tatoo inks, hair dye), food colorants, and inks for printing; modifiers included when application is known     CPCat Cassette
Lubricant    Generic lubricants, lubricants for engines, brake fluids, oils, etc (does not include personal care lubricants)    CPCat Cassette
Manufacturing, agrochemical    Agricultural chemicals used on a variety of crops    CPCat Cassette
Manufacturing, chemical    General term used only when the only information known from the source is 'chemical,' typically related to manufacturing of chemicals, or laboratory chemicals     CPCat Cassette
Manufacturing, export    Related to manufacturing for export (additional information unknown)    CPCat Cassette
Manufacturing, fertilizer    Fertilizer for consumer or industrial use, and manufacturing of fertilizers    CPCat Cassette
Manufacturing, machines    Manufacturing of or related to machinery, for production of cement or food, air/spacescraft machinery, electrical machinery, etc    CPCat Cassette
Manufacturing, metals    Related to metals - manufacturing of metals, casting of metals, production of metals, surface treatment of metals, etc    CPCat Cassette
Manufacturing, oil    Crude oil, crude petroleum, refined oil products, fuel oils, drilling oils    CPCat Cassette
Manufacturing, pesticide    Substances used for preventing, destroying or mitigating pests    CPCat Cassette
Manufacturing, raw_material    Raw materials used in a variety of products and industries (e.g. in cosmetics, chemical manufacturing, production of metals, etc); modifiers included when known to indicate what the raw materials are used for     CPCat Cassette
Manufacturing, soap    Soaps, includes personal care products for cleansing the hands or body, and soaps/detergents for cleaning products, homes, etc    CPCat Cassette
Personal_care, paper, detected    Chemicals detected in substances or products (note that these chemicals may be absent from an 'ingredient list' for the product and thus unexpected, but have been detected in product testing studies)     CPCat Cassette
Pesticide    Substances used for preventing, destroying or mitigating pests    CPCat Cassette
Pesticide, active_ingredient    Active ingredients in a product (often active ingredients in pesticide, if so also tagged with 'pesticide')    CPCat Cassette
Pesticide, food_additive    Includes spices, extracts, colorings, flavors, etc added to food for human consumption    CPCat Cassette
Pesticide, inert_ingredient    Inert ingredients in a pesticide    CPCat Cassette
Printing    Related to the process of printing (newspapers, books media, etc), printing inks, toners, etc    CPCat Cassette
Solvent    Paint removers, graffiti removers, or general solvents    CPCat Cassette
Water_treatment    Includes water softeners, lime removers, and the products used in the process of the collection, purification, and distribution of water    CPCat Cassette

Intermediate for detergents, emulsifiers, wetting agents, stabilizers, textiles treatment, plasticizers for duplicating inks, rubbers, waxes, chromatographic reference standard

Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 775
Hazardous Substances Data Bank (HSDB)
CHEM INT-EG, FOR ALKANOLAMIDES, FATTY ALCOHOLS & ACIDS

SRI
Hazardous Substances Data Bank (HSDB)
EMULSIFIER/EMOLLIENT FOR COSMETICS

SRI
Hazardous Substances Data Bank (HSDB)
LUBRICANT FOR LEATHER

SRI
Hazardous Substances Data Bank (HSDB)
PLASTICIZER & SOFTENER FOR NATURAL & SYNTHETIC RUBBERS

SRI
Hazardous Substances Data Bank (HSDB)
The C19 dicarboxylic acids are obtained from oleic acid and/or methyl oleate by three routes ... .

Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V7 625
Hazardous Substances Data Bank (HSDB)
Intermediate in the production of drying oils

Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V8 140
Hazardous Substances Data Bank (HSDB)
In the production of oleonitrile

Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V9 317
Hazardous Substances Data Bank (HSDB)
Used in the epoxidation of fatty oils and esters in the Repeated- resin process

Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V9 260
Hazardous Substances Data Bank (HSDB)
... In synthesis of cephalosporinS

Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V3 56
Hazardous Substances Data Bank (HSDB)

Industry Uses    
Agricultural chemicals (non-pesticidal)
Functional fluids (open systems)
Intermediates
Lubricants and lubricant additives
Sold to re-sellers for petroleum fuel and petrochemical industry
Solvents (which become part of product formulation or mixture)

Consumer Uses    
Agricultural products (non-pesticidal)
Ink, toner, and colorant products
Lubricants and greases
Personal care products
Sold to re-sellers for petroleum fuel and petrochemical industry
Water treatment products

Methods of Manufacturing    HelpNew Window
Esterification of oleic acid; vacuum fractional distillation; solvent crystallization.

Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 775
Hazardous Substances Data Bank (HSDB)
REACTION OF TRIGLYCERIDES, EG, OLIVE OIL, WITH EXCESS METHANOL AND A CATALYST FOLLOWED BY FRACTIONAL DISTILLATION; REACTION OF OLEIC ACID WITH METHANOL IN THE PRESENCE OF SULFURIC ACID

General Manufacturing Information    HelpNew Window
Industry Processing Sectors
All other basic organic chemical manufacturing
All other chemical product and preparation manufacturing
Pesticide, fertilizer, and other agricultural chemical manufacturing
Petrochemical manufacturing
Petroleum lubricating oil and grease manufacturing
Printing and related support activities
Soap, cleaning compound, and toilet preparation manufacturing

Analytic Laboratory Methods    
DETERMINATION OF METHYL OLEATE IN FATS & OILS BY GAS CHROMATOGRAPHY.

EPA Safer Chemical    
Chemical: Methyl oleate
Yellow triangle Yellow triangle - The chemical has met Safer Choice Criteria for its functional ingredient-class, but has some hazard profile issues. Specifically, a chemical with this code is not associated with a low level of hazard concern for all human health and environmental endpoints. (See Safer Choice Criteria). While it is a best-in-class chemical and among the safest available for a particular function, the function fulfilled by the chemical should be considered an area for safer chemistry innovation.

Health Hazards    
SYMPTOMS: May cause mild irritation on contact with skin or mucous membranes. ACUTE/CHRONIC HAZARDS: Toxic. May cause mild irritation on contact with skin or mucous membrane. Experimental carcinogen. (NTP, 1992)

Fire Hazards    
Combustible (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

First Aid    
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Disposal Methods    
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Nonfire Spill Response    
SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should keep this material in a tightly-closed container under an inert atmosphere, and store it at refrigerated temperatures. (NTP, 1992)

Allowable Tolerances    
Methyl oleate is exempted from the requirement of a tolerance when used as a surfacant in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only.

Personal Protective Equipment (PPE)    HelpNew Window
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. RECOMMENDED GLOVE MATERIALS: Permeation data indicate that neoprene gloves may provide protection to contact with this compound. Neoprene over latex gloves is recommended. However, if this chemical makes direct contact with your gloves, or if a tear, puncture or hole develops, remove them at once. (NTP, 1992)

Air and Water Reactions    
Insoluble in water.
Reactive Group    
Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Hydrocarbons, Aliphatic Unsaturated
Reactivity Profile    
Esters, such as OLEIC ACID METHYL ESTER, react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides

FIFRA Requirements    
Methyl oleate is exempted from the requirement of a tolerance when used as a surfacant in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only.
FDA Requirements    
Methyl oleate is an indirect food additive for use only as a component of adhesives.

Non-Human Toxicity Excerpts    HelpNew Window
0.05 ML OF 10% EMULSION OF OLEIC ACID IN NACL SOLN OR 0.05 ML OF 10% SOLN OF SODIUM OLEATE ADJUSTED WITH HCL TO PH 7.2 INJECTED INTO CORNEAS OF RABBITS CAUSED EYES TO BECOME INFLAMED WITHIN FEW HR & TO DEVELOP CORNEAL ABSCESS WITHIN FEW DAYS. ... METHYL OLEATE ALSO PRODUCED NECROSIS & LIPOGENESIS WHEN TESTED IN SAME WAY.
METHYL OLEATE WAS TESTED FOR CARCINOGENICITY BY ORAL & SC ADMIN IN ST/A MICE OF BOTH SEXES, BUT A POSITIVE EFFECT COULD NOT BE ASSESSED.
METHYL OLEATE PROMOTED SKIN TUMOR FORMATION IN MICE. THE RELATION OF MOLECULAR CONFIGURATION & CARCINOGENICITY OF FATTY ACIDS IS DISCUSSED.
GROWTH OF THE CRICKET, CRYLLODES SIGILLATUS, WAS SHOWN TO BE INHIBITED BY FATTY ACIDS & SOME FATTY ACID METHYL ESTERS. THE ROUTE OF ENTRY APPEARED TO BE THROUGH THE CUTICLE OF THE TARSI. METHYL OLEATE SIGNIFICANTLY RETARDED GROWTH, & RESULTED IN LOWER SURVIVAL.
Methyl oleate was found to be negative when tested for mutagenicity using the Salmonella/microsome preincubation assay, using the standard protocol approved by the National Toxicology Program (NTP). Methyl oleate was tested in as many as 5 Salmonella typhimurium strains (TA1535, TA1537, TA97, TA98, and TA100) in the presence and absence of rat and hamster liver S-9, at doses of 0.100, 0.333, 1.000, 3.333, and 10.000 mg/plate. The highest negative dose tested in any S. typhimurium strain was 10.000 mg/plate. Slight clearing of the background bacterial lawn occurred at the high dose in cultures without activation.

Environmental Fate/Exposure Summary    
Methyl oleate's production and use as a synthetic intermediate may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 6.3X10-6 mm Hg at 25 °C indicates methyl oleate will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase methyl oleate will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 7.5 hours. Vapor-phase methyl oleate will also be degraded in the atmosphere by reaction with ozone; the half-life for this reaction is estimated to be 2.1 hours. Particulate-phase methyl oleate will be removed from the atmosphere by wet and dry deposition. If released to soil, methyl oleate is expected to have no mobility based upon an estimated Koc of 62,000. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 0.014 atm-cu m/mole. However, adsorption to soil is expected to attenuate volatilization. Methyl oleate is expected to rapidly biodegrade in aerobic soils as suggested by the rapid biodegradation of structurally similar long-chain fatty acid esters. If released into water, methyl oleate is expected to adsorb to suspended solids and sediment in the water column based upon the estimated Koc. Methyl oleate is expected to rapidly biodegrade in aerobic waters as suggested by the rapid biodegradation of structurally similar long-chain fatty acid esters. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 5 hours and 7 days, respectively. However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The volatilization half-life from a model pond is estimated to be about 61 hours ignoring adsorption; when considering maximum adsorption the volatilization half-life increases to 18 months. An estimated BCF of 490 suggests the potential for bioconcentration in aquatic organisms is moderate. An estimated base-catalyzed second-order hydrolysis rate constant of 0.011 L/mole-sec corresponds to half-lives of 2 years and 74 days at pH values of 7 and 8, respectively. Occupational exposure to methyl oleate may occur through inhalation and dermal contact with this compound at workplaces where methyl oleate is produced or used. (SRC)
Methyl oleate's production and use as a synthetic intermediate(1) may result in its release to the environment through various waste streams.

Environmental Fate    
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 62,000(SRC), determined from a structure estimation method(2), indicates that methyl oleate is expected to be immobile in soil(SRC). Volatilization of methyl oleate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.014 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Methyl oleate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 6.3X10-6 mm Hg(4). Methyl oleate is expected to rapidly biodegrade in aerobic soils as suggested by the rapid biodegradation of structurally similar long-chain fatty acid esters(5-7).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 62,000(SRC), determined from a structure estimation method(2), indicates that methyl oleate is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 0.014 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Volatilization half-lives for a model river and model lake are 5 hours and 7 days, respectively(SRC), using an estimation method(3). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The volatilization half-life from a model pond is estimated to be about 61 hours ignoring adsorption; when considering maximum adsorption the volatilization half-life increases to 18 months(5). According to a classification scheme(6), an estimated BCF of 490 from its log Kow of 7.45(12) and a regression-derived equation suggests the potential for bioconcentration in aquatic organisms is moderate. Methyl oleate is expected to rapidly biodegrade in aerobic soils as suggested by the rapid biodegradation of structurally similar long-chain fatty acid esters(8-10). An estimated base-catalyzed second-order hydrolysis rate constant of 0.011 L/mole-sec(9,SRC) corresponds to half-lives of 2 years and 70 days at pH values of 7 and 8, respectively(11).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl oleate, which has a vapor pressure of 6.3X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase methyl oleate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 7.5 hours(SRC) from its estimated rate constant of 7.4X10-11 cu cm/molecule-sec at 25 °C(3). Vapor-phase methyl oleate is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 2.1 hours(SRC) from its estimated rate constant of 1.3X10-16 cu cm/molecule-sec at 25 °C(3). Particulate-phase methyl oleate may be removed from the air by wet and dry deposition(SRC).

Environmental Biodegradation    HelpNew Window
AEROBIC: By analogy to chemically similar long chain fatty acid esters that were rapidly degraded by mixed sewage sludge(1-3), methyl oleate is expected to rapidly biodegrade under aerobic conditions(SRC).
The rate constant for the vapor-phase reaction of methyl oleate with photochemically-produced hydroxyl radicals has been estimated as 7.4E-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of methyl oleate with ozone has been estimated as 1.3X10-16 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). A base-catalyzed second-order hydrolysis rate constant of 0.11 L/mole-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 2 years and 70 days at pH values of 7 and 8, respectively(3). The predicted near-surface half-life for the photosensitized oxidation of methyl oleate in near suface waters in the Southern US is 1100 hrs(4). Methyl oleate is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum(5).
An estimated BCF of 490 was calculated for methyl oleate(SRC) using a log Kow of 7.45(1) and a regression-derived equation(2). According to a classification scheme(3), the estimated BCF suggests the potential for bioconcentration in aquatic organisms is moderate.
Using a structure estimation method based on molecular connectivity indices(1), the Koc for methyl oleate can be estimated to be about 62,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that methyl oleate is expected to be immobile in soil.
The Henry's Law constant for methyl oleate is estimated as 0.014 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that methyl oleate is expected to volatilize rapidly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as approximately 5 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as approximately 7 days(SRC). The volatilization half-life from a model pond 2 m deep is estimated to be about 61 hours ignoring adsorption; when considering maximum adsorption the volatilization half-life increases to 18 months(3). Methyl oleate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). Methyl oleate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 6.3X10-6 mm Hg(4).
SURFACE WATER: Methyl oleate was detected in trace quantities in samples from the River Lee, in the UK(1).
Methyl oleate was identified in 3 of 3 New Jersey POTW effluents, date not provided, at a estimated concentration of 0.3-18 ppb(1). It was detected in 13 of 13 effluents samples from an olive oil production plant, Spain, at 520-77721 ug/l(2). It was qualitatively detected in the effluent of a pulp and paper mill in Finland(3).
SOIL: Methyl oleate was qualitatively detected in soil samples from Southern Alberta, Canada, in strata associated with the Mazama volcano eruption which occurred approximately 7000 years ago(1).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 35,946 workers (1,256 of these are female) are potentially exposed to methyl oleate in the US(1). Occupational exposure to methyl oleate may occur through inhalation and dermal contact with this compound at workplaces where methyl oleate is produced or used(SRC).

Methyl oleate produces small amounts of allylic keto-oleates (with CO on carbons 8-, 9-, 10- and 11), epoxy-stearate or epoxy-oleates (8,9-, 9,10- and 10,11-epoxy), dihydroxy-oleates (8,9-, 9,10-, and 10,11-diOH) and dihydroxystearates (between carbon-9 and carbon-11).
Methyl oleate produces small amounts of allylic keto-oleates (with CO on carbons 8-, 9-, 10- and 11), epoxy-stearate or epoxy-oleates (8,9-, 9,10- and 10,11-epoxy), dihydroxy-oleates (8,9-, 9,10-, and 10,11-diOH) and dihydroxystearates (between carbon-9 and carbon-11). The allylic keto-oleates may be derived by dehydration of the corresponding hydroperoxides. 9,10-Epoxystearate may be produced by the reaction of oleate and the hydroperoxides. The other epoxy products can be formed by cyclization of an alkoxy radical formed from the corresponding hydroperoxides of oleate (Figure 4.1). Accordingly, the 11-hydroperoxide forms the 10,11-epoxy ester, the 8-hydroperoxide forms the 8,9-epoxy ester, and the 9- and 10-hydroperoxides form the 9,10-epoxy ester. The 1,2- and 1,4-dihydroxy esters may be formed from a similar alkoxyl radical that undergoes hydroxyl and hydrogen radical substitution via an allylic hydroxy ester radical (Figure 4.1).
Acrylated methyl oleate (AMO) was synthesized using methods reported by Bunker and Wool [4]. The monomer synthesis requires two steps. First, the unsaturated bond in oleic methyl ester (OME) must be epoxidized by a peroxy acid. The epoxidized fatty acid methyl ester is then acrylated using acrylic acid. The acrylate groups are able to participate in free-radical polymerization. A schematic of the monomer synthesis is shown in Fig. 12.2. The OME can also be derived as a by-product from biodiesel, assuming that we have an efficient fatty acid separation process. The separation process was explored by Bunker and Wool and potentially can be done economically at large scale. This would circumvent the need for the development of specialty high-oleic oils and provide additional utilization of biodiesel plants currently being constructed in Delaware and elsewhere. From a green engineering perspective, the biodiesel is perhaps more valuable as a chemical feedstock rather than a combustible fuel feedstock and can attain this value when the current generation of internal combustion engines is replaced in the future by their fuel-cell equivalents.

METHYL OLEATE
WILMARIN ME1898
Wilmarin methyl esters are derived from vegetable oils via transesterification process. Depending on customer requirements, they are available as broad cuts or purer methyl esters by simple or fractional distillation. Common applications for methyl esters include biofuels, lubricants, coatings, food and agriculture and metal working fluids. Chemicals such as fatty alcohol, methyl ester sulfonate and chlorinated methyl ester can be manufactured from methyl esters. Depending on the grade / type of methyl esters, they are available in drums, IBCs, flexibags and bulk shipments.

Specification    Typical Values
Acid Value (mg KOH/g)    1 Max
Saponification Value (mg KOH/g)    180-200
Iodine Value (% I2absorbed)    75 Min
Color (APHA)    100 Max
Moisture Content (%)    0.2 Max
Composition (%)    
C6    1.5 Max
C8
C10
C12
C14
C16
C18:0    97 Min
C18:1
C18:2
C20 & Others    2 Max
Product Form    Liquid

Applications
Methyl oleate is used as a chromatographic reference standard in biochemical research. It is also used as an intermediate for detergents, emulsifiers, wetting agents, stabilizers, textile treatments, plasticizers, for duplicating ink, rubber and wax. It finds application as lubricant and lubricant additive.
Solubility
Miscible with alcohol, ether and chloroform. Immiscible with water.
Notes
Air and light sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.
Description
Methyl oleate is an intermediate for detergents, emulsifiers, wetting agents, stabilizers, textile treatments, plasticizers for duplicating inks, rubbers, waxes etc. It is also used in biochemical research as a chromatographic reference standard.

Molecular Weight    296.49
Formula    C19H36O2
Density    0.874 g/mL at 20 °C
CAS No.    112-62-9
Storage    2 years -20°C liquid
Synonyms    oleic acid methyl ester, Methyl cis-9-Octadecenoate
Smiles    CCCCCCCCC=CCCCCCCCC(=O)OC

Product Description
Oleic acid methyl ester is an esterified version of the free acid which is less water soluble but more amenable for the formulation of oleate-containing diets and dietary supplements. Oleic acid (Item No. 90260) is a monounsaturated fatty acid and is one of the major components of membrane phospholipids. Oleic acid contributes about 17% of the total fatty acids esterified to phosphatidylcholine, the major phospholipid class in porcine platelets.1

WARNING This product is not for human or veterinary use.

Category
Emulsifiers/Surfactants
Description
Clear colorless to amber liquid; [Hawley] Colorless or pale yellow liquid; [MSDSonline]
Sources/Uses
Used to make detergents, emulsifiers, wetting agents, stabilizers, textile treatments, plasticizers for duplicating inks, rubbers, waxes, oleonitrile, drying oils, cephalosporin S, alkanolamides, and fatty alcohols and acids; Used as emulsifier and emollient for cosmetics, lubricant for leather, plasticizer for natural and synthetic rubbers, and chromatographic reference standard; [HSDB]