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CAS NO:110-25-8
EC NO:203-749-3
Oleoyl 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 oleoyl 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.
Oleoyl 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, Oleoyl sarcosine is obtained in 92.5% yield.
Properties
Oleoyl 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.
Oleyl sarcosine is only slightly toxic and easily biodegradable.
Applications
Oleoyl 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.
Oleoyl 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,
Oleoyl 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.
Properties
Chemical formula C21H39NO3
Molar mass 353.547 g·mol−1
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
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
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
Uses
– corrosion inhibitor in metal-working fluids at recommended
concentrations up to 1 % (Ciba-Geigy, undated)
– additive in washing powder
– antistatic treatment of fibres
Oleoyl sarcosine 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 corrosion inhibitor and leather treatment.
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
Oleoyl sarcosine is classified as :
Antistatic
Cleansing
Hair conditioning
Surfactant
Antistatic: Reduces static electricity by neutralizing electrical charge on a surface
Cleaning Agent: Helps keep a clean surface
Hair conditioner: Leaves hair manageable, supple, soft and shiny and / or confers volume, lightness and shine
Surfactant: Reduces the surface tension of cosmetics and contributes to the uniform distribution of the product during its use
Oleoyl Sarcosine is modified fatty acids. In cosmetics and personal care products, these ingredients are used in the formulation of shampoos, bath, cleansing and shaving products.
Oleoyl Sarcosine 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.
Oleoyl Sarcosine also clean skin and hair by helping water to mix with oil and dirt so that they can be rinsed away.
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).
Physical State :Liquid
Solubility :Insoluble in water.
Storage :Store at room temperature
Melting Point :16-17° C
Boiling Point :499.44° C at 760 mmHg (Predicted)
Density :0.96 g/mL
Refractive Index :n20D 1.48 (Predicted)
Oleoyl 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 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.
Oleoyl sarcosine is used in a wide range of applications as a raw material for daily chemicals, cosmetics, and chemical intermediates.
Oleoyl sarcosine is a corrosion inhibitor with the chemical formula C21H39NO3 and a molecular weight of 353.54.
Oleoyl sarcosine is an oil-soluble surfactant with a variety of groups and has been reported abroad since the 1930s.
Oleoyl 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.
Cosmetic Uses:
antistatic agents
cleansing agents
hair conditioning
surfactants
Description
Oleoyl sarcosine is an anionic detergent used for cell lysis during the extraction of RNA
Also suitable for the solubilization of membrane protein
Oleoyl sarcosine is an anionic detergent that is less denaturing than SDS. Uses include solubilization of membranes and cell lysis for extraction of RNA.
Oleoyl sarcosine is a corrosion inhibitor for lubricating oils, greases and fuels
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
N-Oleoylsarcosine
Oleoylsarcosin
OLEOYLSARCOSINE
Z)-N-methyl-N-(1-oxo-9-octadecenyl)glycine
SYNONYMS:
Glycine, N-methyl-N-[(9E)-1-oxo-9-octadecen-1-yl]- [ACD/Index Name]
N-Methyl-N-[(9E)-9-octadecenoyl]glycin [German] [ACD/IUPAC Name]
N-Methyl-N-[(9E)-9-octadecenoyl]glycine [ACD/IUPAC Name]
N-Méthyl-N-[(9E)-9-octadecenoyl]glycine [French] [ACD/IUPAC Name]
N-Oleoyl Sarcosine
[(9E)-N-METHYLOCTADEC-9-ENAMIDO]ACETIC ACID
16693-85-9 [RN]
2-(N-Methyloleamido)acetic acid
2-[(9E)-N-METHYLOCTADEC-9-ENAMIDO]ACETIC ACID
203-749-3 [EINECS]
3,5-Di-tert-butyl-2-iodobenzoic acid
57368-03-3 [RN]
Glycine, N-methyl-N-(1-oxo-9-octadecenyl)-
Glycine, N-methyl-N-[(9Z)-1-oxo-9-octadecenyl]-
Hamposyl O
http:////www.amadischem.com/proen/587415/
Maprosyl O
Medialanic acid (VAN)
MFCD03936142 [MDL number]
N-Methyl-N-(1-oxo-9-octadecenyl)glycine
Oleoyl N-methylaminoacetic acid
Oleoyl sarcosine
Sarcosine, N-oleoyl-
