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CAS NUMBER: 1643-20-5
An amine oxide, also known as an amine N-oxide and N-oxide, is a chemical compound that contains the functional group R3N+−O−, an N−O coordinate covalent bond with three additional hydrogen and/or hydrocarbon side chains attached to N.
Sometimes Amine oxide is written as R3N→O or, wrongly, as R3N=O.
In the strict sense, the term amine oxide applies only to oxides of tertiary amines.
Sometimes Amine oxide is also used for the analogous derivatives of primary and secondary amines.
Examples of amine oxides include pyridine N-oxide, a water-soluble crystalline solid with melting point 62–67 °C, and N-methylmorpholine N-oxide, which is an oxidant.
Many of these products rely on a class of organic compounds known as amine oxides.
Amine oxides are vital to both the cleaning and cosmetic industries.
To understand their importance, we must first understand their general formula and structure.
Once we know this, we can use this information to explain their common uses and applications.
Amine Oxides are surfactants with a high capacity to reduce surface tension, HLB-suitable for the application, and low eye/skin irritability.
An amine oxide is a chemical compound that contains the functional group R3N+−O−, an N−O with three additional hydrogen and/or hydrocarbon side chains attached to N.
An amine oxides acts as a non-ionic surfactant in neutral and alkaline pH and cationic in acidic conditions, and is compatible with most other surfactants.
Amine oxide can be used for numerous applications such as an emulsifier, emulsion stabilizer, and anti-static agent.
In shampoo formulations, Amine oxide is used as a foam booster and thickener, and can be used in conjunction with or instead of alkanolamides.
In neutral or alkaline solutions, Amine oxide exhibits a nonionic character and is therefore compatible with anionics.
In acid solutions, it exhibits mild quaternary properties which enable it to impart substantivity on skin and hair.
Amine oxide is recommended for use in body washes, hand soaps and shampoos.
Amine oxides are amine-based surfactants, represent one of the smaller classes of surfactants as compared to alcohol ethoxylates and sulfonated and sulfated anionic surfactants.
Amine Oxides are an Amphoteric class of surfactants that are excellent detergents, foam boosters and foam stabilizers.
Amine Oxides are used in detergent formulations to provide grease emulsification and soil suspension.
As an amphoteric, Amine Oxides act as nonionic surfactant in neutral and alkaline pH formulations.
Amine Oxide is tightly honed manufacturing process involving ozonation, reverse osmosis and UV filtration ensures that Amine Oxides are microbiologically pure, free from bacteria and other contaminants.
Amine oxides exhibit synergistic effects when combined with anionic and other non-ionic surfactants.
For example, when Amine Oxide is used in combination with anionic sodium lauryl ether sulphate (SLES) Amine oxide increases Amine Oxide’s detergency effect.
Amine Oxide has a low residual hydrogen peroxide, less than 800ppm, whilst the industry norm is 1500ppm.
The finished product has a crystal clear ‘water white’ appearance, ensuring no need for additional colorant in the finished formulation.
USES OF AMINE OXIDE:
Amine oxide can be applied to cleaning products, they perform as excellent detergents, as well as providing excellent foam boosting and foam stabilising properties.
Amine oxides are often used to provide viscosity and strong cleaning powers (grease emulsification and soil suspension) and are extensively used with both sodium hypochlorite and hydrogen peroxide to produce bleach based products.
The series produces a dense, stable foam which can used in the formulation of high alkalinity cleaning compounds.
Amine oxide is used in industrial cleaning, once the product is sprayed on to contaminated equipment the amine oxide allows for excellent adhesion to the surface, providing an extended dwell time as required.
Amine oxide can also be applied in personal care products, (shampoos, bath care and showers gels), as the product provides excellent thickening, emollient and emulsifying properties.
As we mentioned at the start of this lesson, the cleaning and cosmetic industries rely heavily on amine oxides.
Within these industries, amine oxides often play a role as a surfactant.
A surfactant serves to lower the surface tension of a liquid or liquids.
Amine Oxide is this property that the cleaning and cosmetic industries rely on for creating detergents.
Amine Oxide can be applied to cleaning products, they perform as excellent detergents, as well as providing excellent foam boosting and foam stabilising properties.
Amine Oxides are often used to provide viscosity and strong cleaning powers (grease emulsification and soil suspension) and are extensively used with both sodium hypochlorite and hydrogen peroxide to produce bleach based products.
Amine Oxide is stable foam which can used in the formulation of high alkalinity cleaning compounds.
Amine Oxide is used in industrial cleaning, once the product is sprayed on to contaminated equipment the amine oxide allows for excellent adhesion to the surface, providing an extended dwell time as required.
Amine Oxides can also be applied in personal care products, (shampoos, bath care and showers gels), as the product provides excellent thickening, emollient and emulsifying properties.
Amine Oxide can be used for numerous applications such as an emulsifier, emulsion stabilizer, and anti-static agent.
In shampoo formulations, Amine Oxide is used as a foam booster and thickener, and can be used in conjunction with or instead of alkanolamides.
In neutral or alkaline solutions, Amine Oxide exhibits a nonionic character and is therefore compatible with anionics.
In acid solutions, Amine Oxide exhibits mild quaternary properties which enable Amine Oxide to impart substantivity on skin and hair.
Amine Oxide is recommended for use in body washes, hand soaps and shampoos.
APPLICATION OF AMINE OXIDE:
Amine oxides are surfactants commonly used in consumer products such as shampoos, conditioners, detergents, and hard surface cleaners.
Amine oxide is the most commercially used amine oxide.
Amine oxides are considered a high production volume class of compounds in more than one member country of the Organisation for Economic Co-operation and Development (OECD); with annual production over 26,000, 16,000 and 6,800 tonnes (28,700, 17,600 and 7,500 short tons) in the US, Europe, and Japan, respectively.
Amine oxides serve as stabilizers, thickeners, emollients, emulsifiers, and conditioners with active concentrations in the range of 0.1–10%.
The remainder (< 5%) is used in personal care, institutional, commercial products and for unique patented uses such as photography.
Amine oxides are surfactants commonly used in consumer products such as shampoos, conditioners, detergents, and hard surface cleaners.
-Bubble baths
-Hair conditioners & shampoos
-Laundry detergents
-All purpose cleaning agents
-Liquid Bleach products
-Foam stabilisers in rubber and polymer industries
-High or low foaming capabilities
FUNCTION OF AMINE OXIDE:
-Cleansing
-Emulsifier
-Sensory Modifier
-Thickener
PROPERTIES OF AMINE OXIDE:
Amine oxides are used as protecting group for amines and as chemical intermediates.
Long-chain amine oxides are used as amphoteric surfactants and foam stabilizers.
Amine oxides are highly polar molecules and have a polarity close to that of quaternary ammonium salts.
Small amine oxides are very hydrophilic and have an excellent water solubility and a very poor solubility in most organic solvents.
Amine oxides exhibit wetting, emulsifying, cleaning, foam stabilizing and thickening properties in various formulations.
Most amine oxides undergo thermal decomposition between 90 and 200°C.
Amine oxides have some pharmaceutical importance, do not demonstrate surface-acting properties and are more resistant than aliphatic amine oxides to reduction.
Amine oxides are the source of the largest volume of aliphatic amine oxides.
Fatty alcohols are also used to produce amine oxides.
Amine oxides used in industry are prepared by oxidation of tertiary amines with hydrogen peroxide solution.
Amine oxides are used in the detergent, organic synthesis, textile, and pharmaceutical industries.
SYNTHESIS OF AMINE OXIDE:
Almost all amine oxides are prepared by the oxidation of either tertiary aliphatic amines or aromatic N-heterocycles.
Amine oxide is the most common reagent both industrially and in academia, however peracids are also important.
More specialised oxidising agents can see niche use, for instance Caro's acid or mCPBA.
Spontaneous or catalysed reactions using molecular oxygen are rare.
Certain other reactions will also produce amine oxides, such as the retro-Cope elimination, however they are rarely employed.
REACTIONS OF AMINE OXIDE:
Amine oxides exhibit many kinds of reactions.
Amine oxides, when heated to 150–200 °C eliminate a hydroxylamine, resulting in an alkene.
This pyrolytic syn-elimination reaction is known under the name Cope reaction.
The mechanism is similar to that of the Hofmann elimination.
Amine oxides are readily converted to the parent amine by common reduction reagents including lithium aluminium hydride, sodium borohydride, catalytic reduction, zinc / acetic acid, and iron / acetic acid.
Amine oxides can be deoxygenated by phosphorus oxychloride
Oxidants can be regenerated by reduction of N-oxides, as in the case of regeneration of osmium tetroxide by N-methylmorpholine N-oxide.
Amine oxides react with alkyl halides to the O-alkylated product
Amine oxide derivatives adsorbed on silver surfaces are discussed to react with oxygen to bis-ter-pyridine N-oxide.
This reaction can be followed by video-scanning tunneling microscopy with sub-molecular resolution.
SYNONYM:
1-decanamine, N,N-dimethyl-, N-oxide
decyl dimethyl amine oxide
decyl(dimethyl)amine oxide
N,N-dimethyl decyl amine N-oxide
N,N-dimethyl-1-decanamine-N-oxide
N,N-dimethyldecan-1-amine oxide
N,N-dimethyldecylamine N-oxide
N,N-dimethyldecylamine oxide
N,N-dimethyldecylamine-N-oxide
N,N-dimethyldecylamine-N-oxide solution
31820-06-1 [RN]
Amine oxide, ethyl(dimethyl)- [ACD/Index Name]
Ethanamine, N,N-dimethyl-, N-oxide
Ethyl(dimethyl)amine oxide [ACD/IUPAC Name]
Ethyl(dimethyl)aminoxid [German] [ACD/IUPAC Name]
N,N-Dimethylethanamine N-oxide
