PRODUCTS

N-OLEYL SARCOSINE

CAS: 110-25-8
IUPAC Name: 2-[methyl-[(E)-octadec-9-enoyl]amino]acetic acid

Molecular Formula: C21H39NO3
Molecular Weight: 353.5

Functions: Oil soluble corrosion inhibitor
Product Applications: Compressor oil, Engine Oils, Gear Oils, Grease, Hydraulic fluids, Metal working fluids, Turbine oils
Product Classes: Additive Component, Corrosion Inhibitor - Oil Soluble, Lubricants, Metalworking & Grease

N-Oleoylsarcosine (Sarkosyl O) is an amphiphilic oleic acid derivative having a sarcosine head group (N-methylglycine) which is used as a water-in-oil emulsifier and corrosion inhibitor.

N-Oleoyl Sarcosine is a condensation product of oleic acid with N-methylglycine.

Sarkosyl O is a Liquid N-oleyl sarcosine and is a recommended product to formulate lubricants for environmentally sensitive areas.
N-Oleoyl Sarcosine is readily biodegradable according to the OEDC 301X methods, indicating ≥70% dissolved organic carbon or ≥60% O2 depletion / CO2 generation.

INDUSTRY: Cosmetic, Industrial, Water Treatment, Textiles, Plastics, Detergent, Cleaners

PRODUCT PROPERTIES
Boiling Point: 499.4°C
Melting Point: 16.1-17.0ºC
Density: 0.961g/cm3
Refractive Index: 1.481
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.

Uses
– corrosion inhibitor in metal-working fluids at recommended concentrations up to 1 %
– additive in washing powder
– antistatic treatment of fibres

Properties
N-Oleoylsarcosine is a clear, yellow to brown, viscous liquid, which is sparsely soluble in water and acts acidic.
As long-chain N-acylamino acid, the surfactant is soluble in many organic solvents and in mineral oil.
In the alkaline N-Oleoyl Sarcosine dissolves well in water.
Because of its carboxamide structure, Sarkosyl O is chemically stable even at high pH values and strongly foaming as an anionic surfactant.
N-oleyl sarcosine is only slightly toxic and easily biodegradable.

Density: 1.0±0.1 g/cm3
Boiling Point: 499.4±38.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.7 mmHg at 25°C
Enthalpy of Vaporization: 84.1±6.0 kJ/mol
Flash Point: 255.9±26.8 °C
Index of Refraction: 1.481
Molar Refractivity: 104.7±0.3 cm3

Applications
N-Oleoylsarcosine is a mild surfactant which irritates skin and eyes comparatively little and is therefore used in personal care products such as skin cleansing agents because of its antimicrobial and virucidal properties.

The sarcosine head group of the long-chain amphiphilic N-acylamino acid is responsible for the formation of chelate-like structures in the adsorption on polar and charged surfaces, e.g. on metals.

N-Oleoylsarcosine possesses already at low concentrations very good rust protection properties (in particularly in combination with the imidazoline derivative 2-(2-heptadec-8-enyl-2-imidazolin-1-yl)ethanol which also acts emulsifying and anticorrosive), also against non-ferrous metals such as aluminum and copper.
Therefore, N-oleoylsarcosine is added as a corrosion inhibitor and emulsifier to rust protection fluids and lubricating greases, fuels and lubricants and refrigerating lubricants such as drilling and cutting oils.

Production
A standard method for the preparation of N-acylamino acids is the Schotten-Baumann reaction, in which oleoyl chloride (from oleic acid and, e.g. phosphorus trichloride) is added to an aqueous solution of N-methylglycine at pH 10 (kept constant by the addition of sodium hydroxide solution).

Fatty acid-free N-oleoylsarcosine is obtained as an oil.
The method is not suitable for industrial surfactant synthesis because of the relatively expensive production of the carboxylic acid chlorides and the expensive disposal of the phosphonic acid obtained as a byproduct.

N-Oleoylsarcosine can be obtained in the reaction of oleic acid, N-methylglycine and its sodium salt at 170 °C for 8 to 10 hours upon elimination of water.

More gentle conditions (120 °C) and shorter reaction times (3.5 hours) can be used when methyl oleate is reacted with sodium N-methylglycinate upon the addition of equimolar amounts of sodium methoxide in methanol.
After absorption in water, acidification with concentrated sulfuric acid and extraction with butanone, N-Oleoylsarcosine is obtained in 92.5% yield.

Oleoyl sarcosine uses and applications include:

-Corrosion inhibitor, detergent, wetting agent, foam boosterstabilizer, emulsifier for cosmetics, householdindustrial cleaners, biotechnology, agriculture, textiles, petroleum products, metalworking fluids, surfactant coatings, emulsion polymerization;
-surfactant for carpet shampoos, fabric detergents, dishwash, cosmetics, toiletries, toothpaste;
-water treatment;
-mold release agent for RIM;
-stabilizer for polyols;
-antistat in cosmetics;
-antifog and antistat in plastics and food packaging;
-corrosion inhibitor in lubricants for incidental food-contact use;
-antistat in cosmetics

CLASS: Water Treatment

Laboratory studies indicate that N-oleoyl sarcosine is an effective oil soluble rust inhibitor in solution in gasoline, mineral oil and silicone lubricants.

Rusting tests used included: Turbine Oil Rusting Test (ASTM D665-54), a Static Immersion Test, Humidity Cabinet Test (JAN H-792), Static Water Drop Test (MIL-L-17353 Bu. Ord.).
In addition, a number of auxiliary tests were run to indicate the effect of on other properties of the test liquid.

Hydrocarbon solutions of N-oleoyl sarcosine are particularly effective in preventing rusting in the presence of synthetic sea water and in resisting water extraction of the inhibitor.

FUNCTIONS:
-Surfactant
-Emulsifier
-Acid
-Stabilizer
-Metalworking Fluids
-Lubricant

SYNONYMS:

N-Oleoylsarcosine
Sarkosyl O
Oleic sarcosine
Hamposyl O
Maprosyl O
2-[methyl-[(E)-octadec-9-enoyl]amino]acetic acid
Oleyl N-methylglycine
Oleyl methylaminoethanoic acid
N-OLEOYL SARCOSINE
Medialanic acid
NSC-96995
N-Methyl-N-(1-oxo-9-octadecenyl)glycine
Glycine, (Z)-
SCHEMBL220435
SCHEMBL2557574
DTXSID60859192
NSC96995
ZINC59207670
N-Methyl-N-[(9E)-octadec-9-enoyl]glycine
(E)-2-(N-methyloctadec-9-enamido)acetic acid