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EC / List no.: 203-749-3
CAS no.: 110-25-8
Mol. formula: C21H39NO3
Oleyl Sarcosine (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.
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 Oleyl Sarcosine 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.
Oleyl Sarcosine 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, Oleyl Sarcosine is obtained in 92.5% yield.
Properties
Oleyl Sarcosine 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 it 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.
Applications
Oleyl Sarcosine 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.
The molecules form oriented monomolecular films that protect the metal surface from corrosive attack.
Oleyl Sarcosine 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, Oleyl Sarcosine 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.
Industry Uses
Corrosion inhibitors and anti-scaling agents
Finishing agents
Fuels and fuel additives
Lubricants and lubricant additives
Consumer Uses
Fuels and related products
Lubricants and greases
Non-TSCA use
General Manufacturing Information
Industry Processing Sectors
Paint and coating manufacturing
Petrochemical manufacturing
Petroleum lubricating oil and grease manufacturing
Soap, cleaning compound, and toilet preparation manufacturing
Textiles, apparel, and leather manufacturing
Oleyl Sarcosine is light yellow liquid
A powerful anionic surfactant that confers mild detergency, excellent foaming and lathering characteristics.
Displays synergy with other detergents.
Wetting agent.
Enzyme inhibitor in oral care. Corrosion inhibitor.
Oleyl 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
What Is Oleyl Sarcosine?
The acyl sarcosines (Cocoyl Sarcosine, Lauroyl Sarcosine, Myristoyl Sarcosine, Oleoyl Sarcosine, Stearoyl Sarcosine) are modified fatty acids, and acyl sarcosinates (Sodium Cocoyl Sarcosinate, Sodium Lauroyl Sarcosinate, Sodium Myristoyl Sarcosinate, Ammonium Cocoyl Sarcosinate, Ammonium Lauroyl Sarcosinate) are their respective salts.
In cosmetics and personal care products, these ingredients are used in the formulation of shampoos, bath, cleansing and shaving products.
Why is Oleyl Sarcosine used in cosmetics and personal care products?
Acyl sarcosines and sarcosinates enhance the appearance and feel of hair, by increasing hair body, suppleness, or sheen, or by improving the texture of hair that has been damaged physically or by chemical treatment.
Oleyl Sarcosine also clean skin and hair by helping water to mix with oil and dirt so that they can be rinsed away.
Solubility: soluble in organic solvents including paraffin oil and mineral oil, poorly soluble in water (< 0.1 g/l at 23°C) (Ciba-Geigy 1994)
pH: 4 (1 % aqueous suspension) (Ciba-Geigy 1994)
Stability: thermal decomposition at temperatures above 350°C (Ciba-Geigy 1994)
Production: by reaction of oleoyl chloride with sarcosine
Purity: 97 %; for the usual commercially available product a molecular
weight range of 340 to 350 is given (Ciba-Geigy, undated)
Impurities: 2 % free fatty acids (Ciba-Geigy, undated)
Uses of Oleyl Sarcosine:
– corrosion inhibitor in metal-working fluids at recommended
concentrations up to 1 % (Ciba-Geigy, undated)
– additive in washing powder
– antistatic treatment of fibres
Oleyl sarcosine is an amide of oleic acid and sarcosine (N-methylglycine), which is a
normal metabolite in man.
Molecular formula: C21H39NO3
Molecular weight: 353.55
Melting point: 0°C (solidification point)
Boiling point: 397°C
Density at 25°C: 0.95 g/cm3
Vapour pressure at 20°C: 4 × 10–7 hPa
log POW**: > 6
1 ml/m3 (ppm) 14.670 mg/m3: 1 mg/m3 0.682 ml/m3 (pp
ACYL sarcosinates have been known for many years for their good foaming power, skin mildness, and compatibility with many surfactants and conditioning agents.
In particular, oleoyl sarcosine has been widely used as a corrosion inhibitor and leather treatment.
Oleyl sarcosine can also increase emollients deposition on the skin.
Oleyl Sarcosines application in cosmetics (e.g. hair straighteners and depilatory cream) will be described.
Determined safe for use in cosmetics, subject to concentration or use limitations
- Safe for use in cosmetics with some qualifications
Applications:
Separation of Oleyl sarcosine on Newcrom R1 HPLC column
Oleyl sarcosine can be analyzed by this reverse phase (RP) HPLC method with simple conditions.
The mobile phase contains an acetonitrile (MeCN), water, and phosphoric acid.
For Mass-Spec (MS) compatible applications the phosphoric acid needs to be replaced with formic acid. Smaller 3 µm particles columns available for fast UPLC applications.
This liquid chromatography method is scalable and can be used for isolation impurities in preparative separation.
Oleyl sarcosine also suitable for pharmacokinetics.
Oleyl sarcosine is classified as :
Antistatic
Cleansing
Hair conditioning
Surfactant
Category
Foaming Agents
Surfactants / Cleansing Agents
Wetting Agents
Application/Recommended for
Hair care (Shampoos, Conditioners & Styling)
Skin care (Facial care, Facial cleansing, Body care, Baby care)
Toiletries (Shower & Bath, Oral care...) (2)
foam booster
mildness
INCI name: Oleyl sarcosine
EINECS/ELINCS number: 203-749-3
Its functions (INCI)
Antistatic : Reduces static electricity by neutralizing electrical charge on a surface
Cleansing : Helps to keep a clean surface
Hair conditioning : Leaves hair easy to comb, soft, soft and shiny and / or confers volume, lightness and shine
Surfactant : Reduces the surface tension of cosmetics and contributes to the even distribution of the product when it is used
Ecology
Oleyl sarcosine may be hazardous to environment. Water body should be given special attention.
Biodegradability
Oleyl sarcosine is biodegradable.
Characteristics
Oleyl sarcosine is an excellent cleansing, emulsifying, dispersing, solubilizing, foaming, antirust, anticorrosive, wetting, lubricating abilities.
Good compatibility. Resistance to hard water. Easily thickened. Mild surfactant. Suitable for “non-sulfate” formula system.
Note
Oleyl sarcosine Can be used in children cleaning products.
Major Uses
Typical applications
Oleyl sarcosine Use as cleansing agent.
Oleyl sarcosine Use as dispersing agent, emulsifying agent.
Oleyl sarcosine Use as lubricant.
Personal care products
Oleyl sarcosine is a Conditioning agent, antistatic agent, cleansing agent in personal care products.
Oleyl sarcosine has Good compatibility with skin, hair. Suitable for sensitive skin.
Machinery
Oleyl sarcosine Use as cleansing agent, anticorrosive agent, antirust agent.
Oleyl sarcosine has been established that the adsorption of oleyl sarcosinate on zinc is multilayer, which contributes to its best protection under anodic dissolution and in a humid atmosphere with periodic condensation of moisture on the samples.
Treatment of Zn in aqueous solutions of inhibitors increases the time until the appearance of the first corrosion lesions on it under conditions of humid atmosphere 2.5–4.5 times.
Oleoyl Sarcosine may or may not be vegan.
Oleyl sarcosine is a compound of Oleic Acid and Sarcosine, used in cosmetics.
Oleic Acid can have plant or animal sources.
Sarcosine can have plant, animal, or microbiological sources.
The functions of the Oleyl sarcosine
ANTISTATIC : preventing and/or reducing static electricity by neutralising electrical charge on surfaces.
CLEANSING : helping to keep the body surface clean.
HAIR CONDITIONING : enhancing the appearance and feel of hair. leaving the hair easy to comb, supple, soft and shiny and/or imparting volume, lightness, gloss, texture, etc.
SURFACTANT - CLEANSING : wetting body surfaces, emulsifying or solubilizing oils, and suspending soil (generally, such ingredients contribute to the foaming and lathering properties of cleansing products).
"Oleoyl" refers to oleic acid as a component of a compound, "sarcosine" refers to N-methylglycine, an amino acid
Oleyl sarcosine is used in cosmetic formulations.
The mixture of substances acts as an antistatic agent (reduces static charges by neutralizing the electric charge on the surface, e.g. of hair), surfactant (washing-active substance), substance with cleansing effect (cleans the body surface) and as hair conditioning agent (makes the hair easy to comb, smooth, soft and shiny and gives it volume).
Oleyl sarcosine is a corrosion inhibitor with the chemical formula C21H39NO3 and a molecular weight of 353.54.
Oleyl sarcosine is an oil-soluble surfactant with a variety of groups and has been reported abroad since the 1930s.
Oleyl sarcosine was first used in pure form or as a grain of salt in textile washing, toothpaste, shampoo, etc., but has since been introduced into the field of corrosion and rust inhibition.
Appearance & Physical State: light yellow liquid
Density: 0.961g/cm3
Boiling Point: 499.4ºC at 760mmHg
Melting Point: 16.1-17.0ºC
Flash Point: 255.9ºC
Refractive Index: 1.481
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
Vapor Pressure: 2.47E-11mmHg at 25°C
Oleyl sarcosine is obtained by the synthesis of oleoyl chloride from oleic acid and phosphorus trichloride, followed by the Schotten-bannmann condensation with sodium sarcosinate to give sodium N-oleoyl sarcosinate, which is acidified to give N-oleoyl sarcosine.
The factors affecting the reaction are discussed.
Product quality: Acid value 155-165 mg KOH, yield up to 86.76% in terms of oleic acid.
Oleyl Sarcosine is used in a wide range of applications as a raw material for daily chemicals, cosmetics, and chemical intermediates.
The Oleyl Sarcosine, with CAS registry number 110-25-8, has the systematic name of N-methyl-N-[(9Z)-octadec-9-enoyl]glycine.
Oleyl Sarcosine is a kind of light yellow liquid.
And the chemical formula of this chemical is C21H39NO3.
The main use of this chemical is for corrosion inhibitor.
What's more, its EINECS is 203-749-3.The Oleyl Sarcosine irritates to eyes, respiratory system and skin.
When use Oleyl Sarcosine, wear suitable protective clothing, gloves and eye/face protection.
If contact with eyes, rinse immediately with plenty of water and seek medical advice.
IUPAC NAMES:
(Z)-N-Methyl-N-(1-oxo-9-octadecenyl)glycine
(Z)-N-methyl-N-(1-oxo-9-octadecenyl)glycine
(Z)-N-methyl-N-(1-oxo-9-octadencyl)glycine
2-[(9Z)-N-methyloctadec-9-enamido]acetic acid
2-[methyl-[(E)-octadec-9-enoyl]amino]acetic acid
N-methyl-N-oleoylglycine
N-Oleoyl Sarcosine
Oleyl Sarcosine
Oleoylsarcosin
OLEOYLSARCOSINE
Z)-N-methyl-N-(1-oxo-9-octadecenyl)glycine
SYNONYMS:
N-Oleoylsarcosine
110-25-8
Glycine, N-methyl-N-[(9Z)-1-oxo-9-octadecenyl]-
Oleyl sarcosine
16693-85-9
N-Oleyl sarcosine
2-[methyl(octadec-9-enoyl)amino]acetic acid
Glycine, N-methyl-N-[(9Z)-1-oxo-9-octadecen-1-yl]-
ACMC-20995q
DTXSID10892059
ANW-16140
AKOS028108893
VZ36640
DB-040909
FT-0631614
N-Methyl-N-(1-oxo-9-octadecen-1-yl)glycine
Glycine,N-methyl-N-(1-oxo-9-octadecen-1-yl)-
N-Methyloleamidoacetic acid
Glycine, N-methyl-N-(1-oxo-9-octadecenyl)-, (Z)-
Hamposyl o
Maprosyl o
Medialanic acid
Nsc96995
Oleic sarcosine
Oleoyl N-methylaminoacetic acid
221P
Cordesin O
Oleic sarcoside
2-(N-MethyloleaMido)acetic acid
OctadecylaMine N-oleoyl Sarcosinate ----T711 Highly Effective Oil Soluble Corrosion Inhibitor
Glycine,N-Methyl-N-[(9Z)-1-oxo-9-octadecen-1-yl]-
SARKOSYL O
N-OLEOYLSARCOSINATE
N-OLEOYLSARCOSINE
N-OLEYL SARCOSINE
N-CIS-9-OCTADECANOYLSARCOSINE
N-CIS-OCTADECENOYLSARCOSINE
Oleyl sarcosine
2-(N-Methyloleamido)
(z)-glycin
(Z)-N-methyl-N-(1-oxo-9-octadecenyl)glycine
N-Oleyl sarcosine acid
N-(Carboxymethyl)-N-methyloleic amide
N-Methyl-N-[(Z)-1-oxo-9-octadecen-1-yl]aminoacetic acid
N-Methyl-N-[(Z)-1-oxo-9-octadecenyl]glycine
N-Oleoyl-N-methylglycine
[(9-Octadecenoyl)(methyl)amino]acetic acid
Glycine, N-methyl-N-(9Z)-1-oxo-9-octadecenyl-
N-METHYL-N-(1-0X0-9-OCTADECENYL)GLYCINE
N-METHYL-N-(1-OXO-9-OCTADECENYL)GLYCINE
(Z)-N-methyl-N-(1-oxo-9-octadecenyl)glycin
N-methyl-N-(1-oxo-9-octadecenyl)-,(Z)-Glycine
N-Oleoylsarcosine>
N-OLEOYLSARCOSINE USP/EP/BP
